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Sri Lanka's Southern Expressway authorities appoint two teams to monitor for earth slips
Mon, Nov 12, 2012, 10:55 am SL Time, ColomboPage News Desk, Sri Lanka.
Nov 12, Colombo: Sri Lanka Deputy Minister of Transport Nirmala Kothalawala says that two teams have been assigned by the Southern Expressway authorities to observe the earth mounds lining the road on a daily basis.
They are to monitor the condition of the land by the sides of the Expressway especially during the periods of rainy weather.
Environmentalists have criticized the construction of the Expressway when a 25- feet high earth mound collapsed over the Expressway on November 02, blocking around 200 meter section of the southbound lanes.
However, the vigilance of the expressway staff helped to take preliminary safety measures closing a part of the road for traffic and no damage to life and vehicles occurred.
ColomboPage - Recent 10 Stories
Australian federal court dismisses Sri Lankan Tamil's asylum application, orders to return home-- [18 minutes ago]
Minister not satisfied with progress of flood relief, calls for cash assistance for affected families-- [9 hours ago]
Sri Lanka Bribery Commission inquires distribution of assistance to disaster victims-- [9 hours ago]
Sri Lankan Prime Minister to leave for South Korea tomorrow-- [9 hours ago]
Sri Lanka Tourism celebrates its Golden Jubilee
Sri Lankan government promises to rebuild all the houses damaged in floods and landslides
Sri Lanka's Power Regulator ask licensees for regulatory accounts
Fisheries Ministry to pay compensation to fishermen affected by the extreme weather
Sri Lankan President receives warm welcome from G-7 leaders
China provides US$ 1.5 million for Sri Lanka flood relief


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This Coop is located at 5005 43rd Avenue #4L, Queens, NY. 5005 43rd Ave #4L is in the Sunnyside neighborhood in Queens, NY and in ZIP Code 11377. The average listing price for Sunnyside is $533,408. 5005 43rd Ave #4L has 1 bed, 1 bath, and was built in 1932
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Al Goodman of Ray, Goodman and Brown Died at 67
Soul star Al Goodman has died at the age of 67. The singer, best known as one third of R&B group Ray, Goodman & Brown, passed away on Monday, July 26. No more details about his death were available as WENN went to press, but the news was confirmed by Goodman's close friend, The Chi-lites star Marshall Thompson.
He tells CNN.com, "My good friend of at least 40 years passed away yesterday. There's mourning all over the world - in England, in Germany and in Japan. We're all mourning for Al Goodman."
Goodman rose to fame when he joined soul singers The Moments in the 1960s, and they scored a hit in 1970 with "Love On A Two-Way Street", which found its way back into the charts last year as a sample in Jay-Z's "Empire State of Mind".
After a series of line-up changes, Goodman and his bandmate William 'Billy' Brown were joined by Harry Ray and after 10 years and 27 chart hits they switched record labels and changed their name to Ray, Goodman & Brown. Goodman went on to score more hits with the group, including "Special Lady" and "Inside of You" throughout the 1980s, and he continued to record with them under different line-ups until 2008 - notably providing backing vocals for Alicia Keys' song "You Don't Know My Name" in 2003.
The singer's funeral will take place next week in Englewood, New Jersey.
- Priyanka Chopra Throws Her Hat Into the Ring to Be Female James Bond
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- Elijah Wood Clarifies Comment on Child Sex Abuse in Hollywood, Says It's Misinterpreted
- 'Pretty Little Liars' Boss Confirms Someone's Getting Married in Season 7
- Anne Hathaway Throws Shade at the Kardashians, Says It's Unintentional
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Iyana Hughes, a prototypical top-of-the-order slapper, puts pressure on defenses with her speed.
Before Iyana Hughes' heroic base hit lifted Sierra High's softball team to win a 2-1 Sac-Joaquin Section Division-IV playoff game against Central Catholic, it took a heroic effort from four Manteca Unified groundskeepers to get the school's varsity field in playing shape Wednesday.
In her four years of athletics at East Union High, senior Jillian Goulart had little difficulty shinning on a softball field or on a golf course. Now the graduating Lancer will narrow her responsibilities to just one sport, as she signed a letter of intent to play softball for the Simpson University Red Hawks in Redding.
MODESTO – When Jerrica Hauck quietly slipped onto the scene a year ago in the Sac-Joaquin Section Division III Track and Field Trials at Modesto Junior College she won the meet with a personal best 10-foot vault. This year Hauck was on her own personal stage, leading the crowd like at a concert and winning the meet – with another personal record.
It was as dominant as a 2-0 win could be.
Ripon High's first-round playoff baseball game against Capital Christian of Sacramento was postponed Tuesday morning due to rain.
The East Union girls soccer team was right in the fight, going into the intermission trailing host Vista del Lago 2-1. in Folsom. The Lancers proved unable to match the Eagles the rest of the way, getting outscored 2-0 over the last 40 minutes to end their season with a 4-1 Sac-Joaquin Section Division-IV Soccer Championships loss Tuesday.
RIPON - The Ripon Christian girls soccer squad suffered a tough sudden-death shootout loss Tuesday to visiting Forest Lake Christian in the Sac-Joaquin Section Division VI playoff game.
STOCKTON – Will Brink was locked in a five-man playoff at Monday's Sac-Joaquin Section Masters Tournament at the Reserves at Spanos Park for one qualifying spot at the Northern California Championships
Manteca High's baseball team made it look easy on Monday.
The Valley Oak League's co-champions swept the major awards in the year-end coaches meeting.
Head coach Nick Olmo said the recent barrage of accolades and attention garnered by his Sierra High softball team has not affected the players.
The Sac-Joaquin Section Swimming Championship trials ushered in the close of the 2011 season for all area swimmers after the boys wrapped up their races Friday at Tokay High.
PATTERSON - East Union freshman Isela Rivera was involved in all of the Lancers' scoring plays in a 3-0 win over Patterson High Thursday, but she wasn't the only youngster who shined at Patterson Community Stadium.
The challenges of making it to the Sac-Joaquin Section Swimming Finals is no easy task, and several of the area swimmers gave their best shot at coming away with a championship berth during the first day of trials at Tokay High in Lodi Thursday.
There was a time when Mariah Jeffrey figured her senior season at East Union would be her last as a soccer player.
LATHROP - Sierra is still very much in the hunt for a Sac-Joaquin Section playoff berth.
The Ripon and Ripon Christian girls soccer teams both ended the regular season with blowout victories on the road.
Even as an up-and-coming sophomore, Kevin Rodriguez was a leader by example.
Michael Hatfield could always knock down the 3.
RIPON - Ripon clinched its first Trans-Valley League baseball championship since 2001 Thursday after the Indians sent Riverbank home with an 8-0 loss, but they are ...
The Trans-Valley and Southern League boys singles champions were one and done in the Sac-Joaquin Section Coed Tennis Tournament at Oak Park in Stockton on ...
Ripon - Ripon High has all but secured another Trans-Valley League title following Wednesday's 3-1 victory over visiting Escalon.
Patience paid off for Devi Coglio.
STOCKTON - After giving up six costly errors along with some passed balls and base-running miscues, East Union came through with two runs in the top ...
Sierra completed an unbeaten run in the regular season with a 6-0 win over visiting Weston Ranch on Wednesday but won't have a Valley ...
Leah Manuleleua ended her scoring drought against East Union on Wednesday, but more importantly she helped Manteca put a halt to a decade-long stretch without ...
East Union second baseman Deja Guzman may not stand out as much as her Lancers softball counterparts, but that may be because she makes it ...
RIPON - Ripon Christian finished its second-round match with visiting Colfax with a bang.
PATTERSON - With several of his players not competing in the Valley Oak League Tournament last week, Manteca head coach Frank Fontana was concerned his Buffaloes ...
Contents of this site are © 2016 Manteca Bulletin - All Rights Reserved Privacy policy and Terms of service | Contact Us


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'Bones' Final Season Is Pushed to Midseason. Find Out the Replacement
- 11:07 AM, May 21
2010 Cannes International Film Festival - Day 3 - 'Wall Street 2: Money Never Sleeps' Premiere
Photo credit: / WENN
To fit your screen, we scale this picture smaller than its actual size. The original picture size is 1000x661 pixels and this photo has been viewed 7219 times since May 14, 2010


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Leaders Debate at the National Press Club, Canberra
Will you please put your hands together for the Prime Minister Malcolm Turnbull and the Opposition Leader Bill Shorten. My name is Chris Uhlmann ABC's political editor. I'm joined this evening by some distinguished colleagues from the Press Gallery; Laura Tingle from The Australian Financial Review, Andrew Probyn from the West Australian and Ellen Whinnett from the Herald Sun. Our time keeper is Hannah Porter. Gentlemen the only thing you need to remember is when you hear a bell you have 15 seconds to conclude whatever it is that you are saying. Time is short. We will not waste it. Bill Shorten has won the toss and elected that the Prime Minister should open the batting.


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|Publication number
|Publication type
|Publication date
|Feb 22, 1966
|Filing date
|Dec 3, 1963
|Priority date
|Oct 9, 1961
|Also published as
|Publication number
|Hauptmann Karl Heinz, Stahle Helmut, Zeile Karl
|Original Assignee
|Boehringer Sohn Ingelheim
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3,236,857 Patented Feb. 22, 1966 3,236,857 2-(PHENYL-AMINO)-1,3-DIAZACYCLOPENTENE- (2) SUBSTITUTION PRODUCTS Karl Zeile, Karl Heinz Hanptmann, and Helmut Stahle, Ingelheim am Rhine, Germany, assignors to Boehringer Ingelheim G.m.b.H., Ingelheim am Rhine, Germany, a corporation of Germany No Drawing. Filed Dec. 3, 1963, Ser. No. 327,806 Claims priority, application Germany, Oct. 9, 1961, B 64,319; Oct. 4, 1963, B 73,766 21 Claims. (Cl. 260309.6)
This is a continuation-in-part of copending application Ser. No. 227,527, filed October 1, 1962.
This invention relates to novel substitution products of Z-(phenyl-amino)-1,3-diazacyclopentenes-('2) and their non-toxic, pharmacologically acceptable acid addition salts, as well as to a method of preparing these compounds.
More particularly, the present invention relates to a compound selected from the group consisting of substituted Z-(phenyl-amino-1,3-diazacyclopentenes-(2) wherein R and R which may be identical to or different from each other, are each selected from the group consisting of hydrogen, methyl and ethyl, and is mono-, di or tri-substituted diphenyl selected from the group consisting of trifluoromethyl-phenyl, 2,6-dichloro-phenyl, 2-chloro-6-methyl-phenyl, 2-methyl-4- chloro-phenyl, 2-chloro-4-methyl-phenyl, 2-chloro-4- ethyl-phenyl, 2-chloro-6-ethyl-ephenyl, 2-chloro-4-tert. butyl phenyl, 2,6-dichloro-4-met-hyl phenyl, 2,441ichloro-6-methyl-pheny1, 2,4-dimethyl-6-chloro-phenyl, 2,6-dirnethyl-4-chloro-phenyl, and their non-toxic, pharmacologically acceptable acid addition salts.
The novel compounds embraced by Formula I may be prepared by a variety of diiferent methods, among which the following have proved to be most convenient and eflicient:
Method A.By reacting an isothiouronium salt of the formula wherein Z has the same meanings as in Formula I, R is lower alkyl and X is the anion of an acid, preferably the anion of a hydrohalic acid, with an alkylenediamine of the formula HN-CHCH2-NH2 R R, (III wherein R and R have the same meanings as in For mula I.
The reaction between the isothiouronium salt II and the alkylenediamine III is effected by simply heating a mixture of the reactants to about 100-200 C.
This method leads to satisfactory yields of the desired end product. In principle, the reaction may also be carried out at relatively low temperatures (60-140 C.) in the presence of a suitable inert solvent, preferably one which contains polar groups, such as Water or lower alkanols; however, it was found that under these conditions long reaction periods must be accepted if good yields are to be achieved. In those instances where Z is 2,6-disubstituted phenyl, even prolonged heating in the presence of the particular inert solvent leads only to low yields of the reaction product. Even a variation of the last-mentioned process, namely, at elevated pressures, possibly in an atmosphere of an inert gas, does not bring about an increase in the yield.
The isot'hiouronium salt II required as one of the starting compounds may, for example, be prepared in known fashion by heating a thiourea compound obtained from an analogously substituted anilin and ammonium thiocyanate (Houben-Weyl, vol. 9, page 887) with a methyl compound, such as a methyl halide ordimethyl sulfate, in the presence of .a suitable inert organic solvent, such as a lower alkanol.
Method B.By reacting a primary amine of the formula Z-NH (IV) wherein Z has the same meanings as in Formula I, with a 2-alkyl-mercapto-1,3-diazacyclopentene-(2) of the formula wherein R and R have the meanings previously defined and R is lower alkyl.
This reaction may be performed in the presence or absence of an inert solvent. It is important, however, that .a sufiiciently high reaction temperature range be selected in order to drive off the alkylmercaptan released by the reaction. In general, the temperature range required therefor is 500 C.; however, in individual cases it may be necessary to heat the reaction mixture to about 200 C.
The 2-alkylmercapto-1,3 diazacyclopentenes (2) V used as starting compounds in this method may themselves be prepared by alkylation of the corresponding ethylene-thioureas, as described in Organic Syntheses III, 394.
Method C.-By subjecting an N-phenyl-N-(B-aminoethyl)-thiourea or -11rea compound of the formula wherein R and R have the meanings previously defined, with a primary amine of the Formula IV above in the presence of an inert organic solvent, such as xylene, to a temperature of about -180" C.
The bis-(2-oxo-1-imidazolidinyl)-phosphine chlorides VII required as starting materials for this method may themselves be obtained by reacting a correspondingly substituted imidazolidine-l-one with phosphorus pentachlo ride in the presence of chloroform as an inert solvent at a temperature of about 2040 C., as described in Bull. Soc. Chim., France, 1961, pages 2114 et seq.
2-(2',6'-dichlorophenyl)-amino-1,3-diazacyclopentene- 2) 2-(2'-chloro-4'-methyl-phenyl) -amino-1,3-diazacyclopentene- (2 2- (2'-methyl-4-chlorophenyl) -amino-1 ,3-diazacyclopentene- (2) 2- (2'-chloro-4'-ethyl-phenyl) -amino-1 ,S-diazacyclopentene- (2) 2-(2'-chloro-6-ethyl-phenyl) -amino-1,3-diazacyclopentene- 2) 2- (2'-chloro-4'-tert.butyl-phenyl) -amino-1,'3 -diazacyclopentene- (2) 2-(2-trifiuoro-methyl-phenyl) -amino-1,3 -diazacyclopentene- (2) 1-methy1-2- 2,6-diehlorophenyl) -amino-l ,3-diazacyclopentene- (2 l-methyl-Z- (2'-trifluoro-methyl-phenyl -amino- 1 3- diazacyclopentene- (2 l-methyl-Z-(4-tert.butyl-Z chlorophenyl) -amino-1,3
diazacyclopentene- (2 l-methyl-Z- (2'-chloro-6'-ethyl-phenyl) -amino-1,3 -diazacyclop entene- 2) 1-methyl-2-(2'-ch1oro-4'-methyl-phenyl) -amino-1 ,3-
diazacyclopentene- (2) 2- (2,6-dichlorop henyl) -ami.no-4-methy1-1 ,3-diazacyc1opentene- (2 2- (2'-chloro-4-methyl-phenyl) -amino-4-methyl-1,3 -diazacyclop entene- (2) 2- (2-chloro-6'- ethyl-phenyl) -amino-4-methyl-1,3-diazacyclop entene- (2 2- 2'-chloro-6'-methyl-phenyl) -amino-l ,3-diazacyclopentene- 2) 2-(2',6-dichl0ro-4-methyl-phenyl) -amino- 1,3 -diazacyclpentene- 2) 2- (2',4'-dichloro-6'methyl-phenyl) -amino- 1,3 -diazacyclopentene- 2) 2- 2,4-dimethyl-6'-chlorophenyl) -amino-1,3-diazacyclopentene- (2 2-(2',6'-dimethyl-4'-chlorophenyl) -amino-1,3-diazacyclopentene- (2) The following examples will further illustrate the present invention and enable others skilled in the art to understand it more completely. It should be understood, however, that the invention is not limited to the specific examples given below.
Example 1.-Preparati0n of 2-(2'-chloro-4'-melhyl-phenly)-amin0-1,3-diazacycl0pentene-(2) by Method A 43 gm. of the thiourea compound (M.P. 124 C.) of the formula obtained in known fashion from 2-chloro-4-methyl-anilin and ammonium thiocyanate and 20 cc, of methyl iodide were dissolved in 200 cc. of methanol, and the solution was refluxed for two hours. Thereafter, the solvent was evaporated in vacuo, leaving 73.2 gm. of the isothiouronium hydroiodide of the formula CH3- -HI SCHs as a residue. This isothiouronium salt was admixed with 20 cc. of ethylenediamine, and the mixture was heated for about 30 minutes at ISO- C., accompanied by stirring; methyl mercaptan escaped during that time. Subsequently, the reaction mixture was taken up in hot dilute acetic acid, and the resulting solution was made alkaline with 2 N sodium hydroxide. A precipitate formed, which was separated by vacuum filtration, washed with water and dried. It was identified to be 2-(2-chloro-4-methyl phenyl)-amino1,3-diazacyclopentene-(2) of the formula from the isothiouronium salt of the formula and propylene-1,2-diamine. The hydrochloride of the base had a melting point of 270-271 C.
- (b) 2 (2' methyl 4' chlorophenyl) amino 1,3- diazacyclopentene-(2) of the formula having a melting point of 133 C. from the isothiouronium salt of the formula SCHa and ethylenediamine. The hydrochloride of the base had a melting point of 199-201 C.
(c) 2 (2 chloro 4' ethyl phenyl) amino 1,3- diazacyclopentene-(Z) of the formula having a melting point of 124-425 C. from the isothiouronium salt of the formula and ethylenediamine. The nitrate of the base had a melting point of 126127 C.
Example 2.-Preparati0n of 2-(2,6'-dichlor0phenyl)- amino-I,S-diazacyclopentene-(2) by Method A 16 gm. of the thiourea compound (M.P. 149 C.) of the formula This isothiouronium salt was then admixed with a molar excess (120 mol percent) of ethylenediamine, and the mixture was heated at 1i30-150 C. for about one hour, accompanied by stirring. Methylmercaptan escaped during that time. The reaction mixture was then taken up in hot dilute acetic acid, and the resulting solution was made alkaline with 2 N sodium hydroxide. The precipitate formed thereby was separated by vacuum filtration, washed with water and dried. It was identified to be 2-(2,6'-dichlorophenyl)-amino-1,3-diazacyclopentene-(2) of the formula having a melting point of 130 C. The yield was 4.0 gm.
Its hydrochloride had a melting point of 305 C. Using a procedure analogous to that described above, the following additional substituted phenylamino-LS-diazacyclopentene-(Z) were prepared:
(a) 2 (2 chloro 6' methyl phenyl) amino 1,3- diazacyclopentene-(Z) of the formula but having a melting point of 143145 C. from the isothiouronium salt of the formula and ethylenediamine. The hydrochloride of the base had a melting point of 217-220 C.
(b) 2 (2' chloro 4 tert.butyl phenyl) amino: 1,3-diazacyclopentene-(2) of the formula from the isothiouronium salt of the formula C] CH3 1 NH CH SCHa and ethylenediamine. The free base had a melting point of 156-158 C., and its nitrate had a melting point of 129 C.
(c) 2. (2' chloro 6 ethyl phenyl) amino 1,3- diazacyclopentene-(2)-of the formula from the isothiouronium salt of the formula and ethylenediamine. The hydrochloride of the base had a melting point of 200 C.
Example 3.Preparation of 2-(2-triflu0r0methyI-phenyl)-amin0-1,3-diazacyclopentene-(2) by Method A 20.3 gm. of the thi-ourea compound (M.P. 162163 C.) prepared in known fashion from o-trifluoromethyl-aniiine and ammonium thiocyanate, and 10 cc. of methyliodide were dissolved in 40 cc. of absolute methanol, and the re sulting solution was refluxed for two and a half hours. Thereafter, the methanol was evaporated in vacuo, leaving as a residue 23 gm. of the isothiouronium hydroiodide of the formula CFs The residue was admixed with 8 cc. of ethylenediamine, and themixture was heated for about 30 minutes at C., accompanied by stirring. Methylmercaptan escaped during that time. The reaction mixture was allowed to cool and was then taken up in dilute hydrochloric acid. The resulting solution was made alkaline with 2 N sodium hydroxide. The precipitate formed thereby, which was identified to be 2-(2'-trifluoromethyl-phenyl)-amino- 1,3-diazacyclopentene-(2) of the formula was taken up in chloroform, and the resulting solution was admixed with ethereal hydrochloric acid, whereby a precipitate formed. Precipitation was brought to completion by further addition of ether. 6 gm. of 2-(2'-trifiuoromethyl phenyl)-amino-1,3-diazacyolopentene-(2) hydrochloride (M.P. l96198 C.) were obtained.
Example 4.Preparation of I-methyl-Z-(Z,6'-dichl0r0- phenyl)amino-1,3-diazacyclopentene-(2) by Method A 16 gm. of the thiourea compound (M.P. 149 C.) obtained in known fashion from 2,6-dichloro-aniline and ammonium thiocyanate, and 16 grrn of methyl iodide were dissolved in 150 cc. of methanol, and the solution was refluxed for two and a half hours. Thereafter, the solvent was evaporated in vacuo, leaving as a residue 22 gm. of
7 the isothiouronium hydroiodide (M.P. 170 C.) of the formula having a melting point of 83 C. were obtained.
The nitrate of the base had a melting point of 226 C. and was soluble in water and ethanol.
Using a procedure analogous to that described above, the following additional substituted l-methyl-Z-phenylamino-1,3-diazacyclopentenes-(2) were prepared:
(a) 1 methyl 2-(2'-trifluoromethyl-phenyl)-amino- 1,3-diazacyclopentene-(2) of the formula N-CH3 NHC \NCH2 from the isothiouronium salt of the formula NH -NH- -HI \S CH3 and N-methyl-ethylenediamine. The free base had a melting point of 58-61 C., and its nitrate had a melting point of 182-183 C.
(b) 1 methyl 2-(2'-chloro-4'-methyl-phenyl)-amino- 1,3-diazacyclopentene-(2) of the formula l /NCH3 III-CH2 CH from the isothiouronium salt of the formula I NH CHaNHO\ 111 SCH,
and N-methyl-ethylenediamine.
A mixture of 12.5 gm. of 2,4-dichloro-6-methylaniline (prepared by chlorinating o-toluidine in glacial acetic acid and ferric chloride according to Adams, J.A.C.S., 72, 2454), 170 cc. of water, 37 cc. of concentrated hydrochloric acid and 36.8 gm. of ammonium thiocyanate was refluxed for seven hours. The thiourea compound of the formula 8 thus obtained was isolated in the manner described in the preceding examples and was recrystallized from ether, whereupon it had a melting point of 183184 C. Yield: 18 gm.
All of the thiourea compound thus obtained and 33 gm. of methyliodide were dissolved in 300 cc. of methanol, and the solution was refluxed for about three hours. Thereafter, the solvent was evaporated in vacuo, having as a residue the isothiouronium salt of the formula This residue was admixed with 7 gm. of ethylenediamine, and the resulting mixture was heated for about one hour at C., accompanied by stirring, during which time methylmercaptan escaped. The reaction mixture was then taken up in 2 N hydrochloric acid, the resulting solution was extracted with chloroform, the chloroform extract solution was filtered through charcoal, and the filtrate was made weakly alkaline with ammonia. The alkaline solution was then extracted with chloroform, the extract solution was dried and filtered through charcoal, and the chloroform was distilled in vacuo from the filtrate. The residue was identified to be 2-(2',4-dichloro-6-methylphenyl)-amino-1,3-diazacyclopentene-(2) of the formula The free base was converted into its oxalate by adding an ethanolic solution of oxalic acid, extracting the resulting solution with ether and evaporating the ether from the extract solution. After recrystallization from a mixture of isopropanol and ether the oxalate had a melting point of 261-263 C. Yield: 9.5 gm.
Using a procedure analogous to that described above, the following additional tri-substituted 2-phenyl-amino- 1,3-diazacyclopentenes-(2) were prepared:
(a) 2 (2',6-dichloro-4'-methyl-phenyl)-amino-l,3-diazacyclopentene-(Z), M.P. 156 C., of the formula N-CH: C]
from the isothiouronium salt of the formula and ethylenediamine.
(b) 2 (2,4'-dimethyl-6'-chloro-phenyl)-amino-1,3-diazacyclopentene-(Z) of the formula from the isothiouronium salt of the formula /NH on NHO .nr l son,
and ethylenediamine. The oxalate of the base had a melting point of 210 C.
from the isothiouronium salt of the formula om-Q-mzr-o SCHs CH and ethylenediamine. The oxalate of the base had a melt- 1 ing point of 165 C.
The novel phenylamino-1,3-diazacyclopentene-(2) substitution products according to the present invention, that .is, the compounds embraced by Formula I above and their non-toxic, pharmacologically acceptable acid addition salts, have useful pharmacodynamic properties. More particularly, the compounds of the present invention exhibit highly effective hypotensive and sedative activities, and some of them also have vasoconstrictive properties.
Typical examples of non-toxic, pharmacologically acceptable acid addition salts of the bases of the Formula I are those formed with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, nitric acid, acetic acid, propionic acid, butyric acid, valeric acid, oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, lactic acid, tartaric acid, citric acid, malic acid, benzoic acid, phthalic acid, cinnamic acid, salicylic acid, nicotinic acid, 2-furoic. acid, ascorbic acid, 8-chlorotheophylline and the like.
The compounds according to the present invention were tested on humansubjects and were found to be highly effective hypotensive agents. For instance, in healthy, normal human test subjects a dose of 0.3 mgm. of 2- (2',6'-dichloro-phenyl) -amino-1,3-diazacyclopentene- (2) produced a drop in the systolic blood pressure of up to 35 mm. Hg, which had not completely subsided after 24 hours. Approximately the same reduction in blood pressure over the same period of time was achieved by administration of 0.6 mgm. of 2-(2-chloro-4-methylphenyl)-amino-1,3-diazacyclopentene-(2) or 0.6 mgm. of 2-(2'-ch1oro-6-methyl-phenyl)-amino 1,3 diazacyclopentene-(Z). In this connection it should be emphasized that the compounds of the present invention reduce the blood pressure even in normal, healthy humans with normal blood pressure; this is of particular importance because most therapeutically applied hypotensive agents either produce no such effect in humans having normal blood pressure or reduce normal blood pressure only if administered at extremely high dose rates. Further, we have found that considerably lower dosages of the compounds according to the invention are required for treatment of high blood pressure than of most known hypotensive agents. For instance, in oriented clinical tests on high blood pressure patients it was found that a dose of only 0.15 mgm. of 2-(2,6-dichlorophenyl)-amino-1,3- diazacyclopentene-(Z) produces an average reduction of 45 mm. Hg in the systolic blood pressure.
A further advantage of the compounds according to the present invention is their low toxicity. For instance, the LD of 2-(2',6'-dichlorophenyl)-amino-1,3 diazacyclopentene-(Z) in mice is 390 mgm./kg. per s and 127.5 mgm./kg. s.c.; for 2-(2-chloro-6'-methyl-phenyl)- amino-1,3-diazacycloptene-(2) it is 180 mgm./kg. per 0s and 102 mgm./kg. s.c.; and for 2-(2-chloro-4-methylphenyl)-amino-1,3-diazacyclopentene-(2) it is 320 mgm./ kg. per 0s and 42.5 mgm./kg. s.c. These values indicate an extraordinarily favorable therapeutic ratio which assures the safety of the novel compounds in therapeutic applications.
In addition, the compounds of the present invention exhibit efiective sedative activities which are already detectable at the hypotensive dosages, but become clearly observable at slightly higher dosages. Thus, a dose of 0.2-0.4 mgm. of 2-(2',6'-dichlorophenyl)-amino 1,3- diazacyclopentene-(Z) produced sedation which lasted for six hours, and a dose of 1-2 mgm. produced sedation which persisted for about thirty hours. 0.61 mgm. of 2-(2-chloro-4-methyl-phenyl)-amino 1,3 diazacyclopentene-(2) induced sedation lasting for 5-8 hours, and after administration of 2.4 mgm. of this compound the test subjects slept for about 19 hours. Similar effects were achieved with 2-(2 chloro-6 methyl phenyl)- amino-1,3-diaZacyclopentene-(2) The compounds of the present invention induce a sound and long-lasting sleep from which the patients may, however, be fully awakened at any time. Thus, the novel compounds offer a substantial advantage over customary sleep-inducing sedatives, especially over the barbiturates; for instance, a moderate overdose of such customary sedatives which induces sleep for 20-30 hours invariably leads to unconsciousness almost resembling a state of anesthesia for the first few hours, from which the patient can be awakened into a dazed state for brief periods of time only by strong stimulations.
The compounds of the present invention also possess vasoconstrictive properties, particularly the compounds 2-(2,6-dichlorophenyl)-amino-1,3 diazacyclopentene- (2) and '2-(2-chloro-6'-methyl-phenyl)-amino-1,3-diazacyclopentene-(Z).
For therapeutic application the compounds of the present invention are administered perorally 0r parenterally as active ingredients in dosage unit compositions, that is, in compositions consisting essentially of an inert, physiologically compatible carrier having uniformly distributed therein one dosage unit of the active ingredient. One dosage unit of the compounds of the present invention is from 0.025 to 10 mgm.
The following examples illustrate a few dosage unit compositions comprising a compound of the present invention as the active ingredient. The parts are parts by weight unless otherwise specified.
Example 6 Tablets.The tablet composition is compounded from the following ingredients:
Parts 2 (2',6' dichlorophenyl) amino 1,3 diaza- The individual ingredients are admixed in customary fashion, and the mixture is pressed into tablets weighing mgm. each. An individual tablet then contains 0.1 mgm. of the active ingredient.
Example 7 S0lu1i0n.-The solution is compounded from the fol lowing ingredients:
Parts 2 (2' chloro 4' methyl-phenyl) amino 1,3-
diazacyclopentene-(Z) 0.02 p-Benzoic acid methyl ester 0.07 p-Benzoic acid propyl ester 0.03
Demineralized water, q.s. ad parts by vol.
The various solid ingredients are dissolved in the demineralized water, and the solution is filled into 100 cc. bottles. Twenty drops of the solution (1 cc.) contain 0.2 mgm. of the active ingredient.
1 1 Example 8 Hypodermic slutions.The solution is compounded from the following ingredients:
Parts 2 (2' chloro 6' methyl phenyl) amino 1,3-
diazacyclopentene-(Z) nitrate 0.05 Sodium chloride 18.0
Distilled water, q.s. ad 2000 parts by vol.
The active ingredient and the sodium chloride are dissolved in a portion of the distilled water, and the solution is then diluted with distilled water to the required volume. 'The solution is then filtered until free from fibrous material and is filled into 2 cc. ampules, which are then sterilized and sealed. Each ampule contains 0.05 mgm. of the active ingredient.
Example 9 Rectal suppositories-The suppository composition is compounded from the following ingredients:
Parts 2-(2,6 dichlorophenyl)-amino-1,3 diazacyclopentene-(Z) 0.4 Lactose 244.6 Cocoa butter, q.s. ad 1700 parts by vol.
The cocoa butter is melted, the active ingredient and the lactose are added, the mixture is allowed to cool slightly and is then homogenized. Thereafter, the composition is poured into cooled suppository molds holding 1700 mgm. each. Every individual suppository contains 0.4 mgm. of the active ingredient.
Although the above dosage unit composition examples illustrate only certain specific compounds of the present invention as active ingredients, it should be understood that any of the other compounds embraced by Formula I or their non-toxic acid addition salts may be substituted in the compositions for those specifically illustrated. Similarly, the amount of the active ingredient in the illustrative compositions may be varied within the indicated dosage range to meet particular requirements and depending upon whether only a hypotensive eflect or also a sleep-inducing sedative efliect is to be achieved. In the case of hypodermic solutions the active ingredient is preferably provided in the form of a non-toxic acid addition salt.
While the present invention has been illustrated with the aid of certain specific embodiments thereof, it will be readily apparent to those skilled in the art that the invention is not limited to these embodiments and that various changes and modifications may be made Without departing from the spirit of the invention or the scope of the appended claims.
We claim:
1. A com-pound selected from the group consisting of 2-phenylamino 1,3 diazacyclopentene-(2) substitution products of the formula R and R are each selected from the group consisting of hydrogen, methyl and ethyl, and Z is selected from the group consisting of 2,6-dichlorophenyl, Z-trifiuoromethyl-phenyl, 2-chloro-6-methyl-phenyl, 2-methy1-4-chloro-phenyl,
2-chloro-4-methyl-phenyl, 2-chloro-4-ethyl-phenyl, 2-chloro-6-ethyl-phenyl, 2-chloro-4-tert.butyl-phenyl, 2,6-dichloro-4=methyl-phenyl, 2,4-dichloro-6-methyl phenyl, 2,4-dimethyl-6-chloro-phenyl and 2,6-dimethy1-4-chloro-phenyl,
and their non-toxic, pharmac'ologieally acceptable acid addition salts.
2. 2-(2',6'-dichlorophenyl) amino 1,3-diaz'acyclopentene-(Z).
3. 2-(2'-chloro-4'-methyl-phenyl) amino 1,3diazacyclopentene- (2) 4. 2-(2'-chloro 6-methyl-phenyl) amino 1,3-diazacyclopentene- (2) 5. 2-(2-methyl 4-chl-orophenyl) amino 1,3-diazacyelopentene-(Z).
6. 2-(2'-chloro 4'-ethyl-phenyl) amino 1,3-diazacyclopentene- 2) 7. 2-(2'-chloro 6'-ethyl-phenyl) amino 1,3-diazacyclopentene- 2) 8. 2-(2-chloro 4'-tert.butyl-phenyl) amino 1,3-diazacyclopentene- (2) 9. 2-(2-trifluoromethyl phenyl) amino 1,3-diazacyclopentene- (2 10. 1-methyl-2-(2',6 dichlorophenyl) amino 1,3- diazacyclopen tene- 2) 11. 1 methyl-2-(2'-trifiuoromethyl phenyl) amino- 1,3-diazacyclopentene- (2) 12. 1-methyl-2- (4'-tert.butyl 2-chlorophenyl) amino- 1,3-diazacyclopentene- 2) 13. 1-methyl-2-(2'-chloro 6-ethyl phenyl) amino- 1,3-diazacyclopentene- 2) =14. 1-methyl-2-(2'-chloro 4'-rnethyl phenyl) aminoamino-l ,3-diazacyclopentene- (2) 15. 2-(2',6'-dichlorophenyl) amino 4-methyl 1,3-diazacyclopentene- (2) 16. 2-(2-chloro 4'-methy1 phenyl) amino-4-methyl- 1,3-diazacyclopentene-(2) 17. 2-(2'-chloro 6'-ethyl phenyl) amino-4-methyl- 1,3-diazacyclopentene(2) 18. 2-(2,6-dichloro 4-methyl phenyl) amino-1,3- diazacyclopentene-( 2) I 19. 2-(2,4'-dichloro 6'-methyl phenyl) amino-1,3- diazacyclopentene- (2 20. 2-(2',4'-dimethyl 6'-chlor0phenyl) amino 1,3- diazacyclopentene- (2) 21. 2-(2',6'-dirnethy1 4'-ch1orophenyl) amino 1,3- diazacyclopentene- 2) References Cited by the Examiner UNITED STATES PATENTS 1,912,849 6/ 1933 Kranzlein et a1 260-3096 2,742,481 4/1956 Cain 260309.6 2,744,909 5/1956 Speeter 260309*.6 2,899,426 8/1959 Bloom 260309.6 2,899,434 8/1959 Bloom 260-2564 3,024,166 3/1962 Kuna et al 16765 3,036,955 5/1962 Kuna et al. 16765 3,081,222 3/ 1963 Hageman et al 260---309.6
FOREIGN PATENTS 625,631 8/1961 Canada.
IRVING MARCUS, Primary Examiner.
Disclaimer 3,236,857.Karl Zeile, Karl Heinz Hauptmarm and Helmut Stahle. Ingelheim am Rhine, Germany. 2-(PHENYL-AMINO)-l,3-DIAZACYCLOPENT- ENE-(2) SUBSTITUTION PRODUCTS. Patent dated Feb. 22, 1966. Disclaimer filed Aug. 13, 1982, by the assignee, Boehringer Ingelheim G. m. b.H.
The term of this patent subsequent to Aug. 24, 1982 has been disclaimed.
[Official Gazette November 16, 1982.]
|Cited Patent
|Filing date
|Publication date
|Apr 8, 1929
|Jun 6, 1933
|Ig Farbenindustrie Ag
|Heterocyclic bases of the aminoimidazoline series and process of preparing them
|Oct 20, 1953
|Apr 17, 1956
|Mcneilab Inc
|Dialkylaminoimidazoline compounds and their preparation
|Jun 27, 1955
|May 8, 1956
|Bristol Lab Inc
|2-(ortho-phenylbenzyl) imidazoline and acid addition salts
|Oct 18, 1956
|Aug 11, 1959
|Synthesis of l
|Oct 18, 1956
|Aug 11, 1959
|Mar 22, 1960
|Mar 6, 1962
|Bristol Myers Co
|Analgesic dihydroxymethylbenzimidazol-2-ones
|Jun 8, 1960
|May 29, 1962
|Bristol Myers Co
|Analgesic 5-lower alkyl-2-amino thiazoles
|Mar 11, 1960
|Mar 12, 1963
|Us Rubber Co
|Aug 15, 1961
|Pfizer & Co C
|Derivatives of diazacycloalkenes
|Citing Patent
|Filing date
|Publication date
|Dec 21, 1965
|Jul 8, 1969
|Boehringer Sohn Ingelheim
|2 - (phenyl - amino) - 1,3 - diazacyclopentene - (2) substitution products for reducing blood pressure
|Oct 24, 1967
|Sep 23, 1969
|Boehringer Sohn Ingelheim
|Process for the preparation of 2-phenylamino-1,3-diazacycloalkenes-2
|Nov 13, 1967
|Nov 10, 1970
|Standard Oil Co
|Method of preparing cyclic ureas from n,n-dialkylammonium n,n-dialkyl monothiol carbamates and diprimaryamines
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|Jun 18, 1974
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|Hypotensive pharmaceutical compositions containing certain 2-anilino-1,3-diazacyclopentenes-(2)
|Mar 29, 1974
|Jan 6, 1976
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|Feb 10, 1976
|Boehringer Ingelheim Gmbh
|Aug 25, 1975
|Jul 19, 1977
|Boehringer Ingelheim Gmbh
|2-(N-thienylmethyl-phenylamino)-imidazolines-(2) and salts thereof
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|Nov 14, 1978
|Boehringer Ingelheim Gmbh
|2-[(2',6'-Disubstituted-phenyl)-imino]-imidazolidines and salts thereof
|Feb 12, 1979
|Jul 22, 1980
|Boehringer Ingelheim Gmbh
|2-Phenylimino-imidazolidines and salts thereof
|May 31, 1977
|Jul 29, 1980
|Richardson-Merrell Inc.
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|Nov 6, 1978
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|Hoffman-La Roche Inc.
|2-Imino-imidazolidine derivatives
|Jul 13, 1979
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|Irving Cooper
|Means and method for aiding individuals to stop smoking
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|Hoffman-La Roche Inc.
|2-Imino-imidazolidine derivatives
|Dec 23, 1982
|Apr 24, 1984
|Smithkline Beckman Corporation
|2(4-tert.-Butyl-2,6-dichlorophenyl-imino)imidazolidine and use as an anti-hypertension agent
|Nov 20, 1981
|Jul 24, 1984
|Alcon Laboratories, Inc.
|2-(Trisubstituted phenylimino)-imidazolines
|Aug 3, 1983
|May 7, 1985
|Icilio Cavero
|Method of lowering intraocular pressure using phenylimino-imidazoles
|Aug 3, 1983
|May 14, 1985
|Alcon Laboratories, Inc.
|Method for lowering intraocular pressure using phenylimino-imidazoles
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|Feb 17, 1987
|Alcon Laboratories, Inc.
|3-chloro-4-(4,5-dihydro-1H-imidazo-2-yl)-amino-5-alkylbenzoic acids, esters, salts, compositions and methods
|Feb 7, 1995
|Nov 4, 1997
|Pierce; David R.
|Process for preparation of clonidine derivatives
|Dec 7, 2004
|Apr 21, 2005
|Boehringer Ingelheim International Gmbh
|Alkylphenyliminoimidazolidine derivatives for treating urinary incontinence
|Dec 21, 2001
|Jul 10, 2003
|Aventis Pharma Gmbh
|Substituierte Imidazolidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie enthaltendes Medikament
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|International Classification
|Cooperative Classification
|European Classification


text:
Spectral Debt
Gonzo the Eggman
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It is 2016. I think it is high time that Captain America have a dog man as a boyfriend.
A brave pop culture addict puts his foot down once and for all.
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text:
Kids Say The Darndest Things
No kid is exactly the same because kids are, like us parents, unique individuals. However, it boggles my mind how predictable and similar children and the catch phrases they use can be. I'm hungry. This phrase is classically heard just after the click of carseat buckles or the turn of a car key as you're pulling away from a party where copious amounts of food was served, but not eaten. I have to go to the bathroom really bad. This one usually comes halfway into a walk to the playground, or when you're pulling the car onto the highway for a 30 minute trip. I'm NOT tired! shrieks the overly tired toddler at nap time. I think this video clip about sums it up. You never let me do anything fun. Oh, challenge accepted my dear. You're not invited to my birthday party. I hate you. You're the worst mom ever. I'm sending you to jail! I'll group all of the insults together. They'd be insulting were they not so hilarious. I find that laughing in their face really isn't the best way to handle these. Ignore. Ignore. Ignore. I promise they'll phase them out, at least until we hear them again at 13 or so. Then there are the good things. When I really stop to think about it, and to document it, there are way more good phrases than...Read More


text: Who Needs a Waiter? Order Your Dinner with an iPad By Gordon Tokumatsu UP NEXT XWho Needs a Waiter? Order Your Dinner with...LinkEmbedEmailCopyCloseLink to this videohttp://www.nbclosangeles.com/on-air/as-seen-on/Murrieta-Teacher-Pleads-Guilty-to-Sex-WIth-Student_Los-Angeles-381051891.htmlCopyClose Embed this video Replay More videos (1 of 9)«»Forget the waiter, now the iPad can take your order when you eat out. NEWSLETTERS Receive the latest as-seen-on updates in your inboxPrivacy policy | More Newsletters


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A fabulous 16 year old Arran from independent bottlers Douglas Laing. Matured in a single Sherry butt after distillation during the summer of 1996, it was bottled as part of the Provenance range in… More info
This is an astounding single cask whisky from the Isle of Arran distillery. It was distilled on the 8th August 1996 before a 16 year maturation in a first-fill sherry puncheon. We bottled it on the… More info
So it seems Berry Bros. & Rudd are getting into whiskies with interesting finishes! This 16 year old Arran single malt, from the Isle of Arran, spent an undisclosed amount of time near the end of its… More info
A Strictly Limited bottling of Arran single malt, made possible by Càrn Mòr. It was drawn for 2 hogsheads which matured the whisky for 16 years, from 1997 to 2014. 568 bottles of tasty island whisky… More info
From the Rest & be Thankful Whisky Company's selection of independently bottled whiskies comes a 16 year old single malt from the Arran distillery, matured in a single bourbon cask. Back in June… More info
An Arran from Gordon & MacPhail's Connoisseurs Choice range. Distilled in 2000, it was bottled in 2013 following a maturation period spent in refill bourbon casks. More info
Another lovely Premium Single Cask bottling from the Arran distillery. The island distillers filled single Sherry cask #893 in July 1998 and left it to mature for 16 years. In September 2014, the… More info
This was distilled at the Auchentoshan distillery in Autumn 2000 before a 12 year maturation in a single refill hogshead. It was bottled in Winter 2012 and it comes from the impressive Provenance… More info
Distilled in the autumn of 2000 and bottled in spring 2013, this 12 year old Auchentoshan was matured in a single refill hogshead before bottling as part of Douglas Laing's Provenance range. More info
This Provenance bottling of 13 year old Auchentoshan single malt Scotch whisky honours the season of Spring, as it was in the Spring of 2000 that it was distilled. Another brilliant single cask… More info
A classically light, elegant Auchentoshan single malt Scotch whisky, bottled by Douglas Laing for the Old Particular range. It was distilled in the Lowlands in September 2000 and matured in a single… More info
A 16 year old Auchentoshan bottled by WM Cadenhead for the new range, Duthies. Duthies consists of 6 whiskies from a range of distilleries, none of which are chill-filtered, nor do they have added… More info
This Auchentoshan was aged in bourbon and finished in Chateau Climens (a first growth Sauternes wine producer in the Barsac appellation). They bottled this in 2008 at Bruichladdich and it's a limited… More info
An independent bottling from Lowland distillery Auchentoshan here. Triple-distilled single malt matured for 16 years in a single hogshead before it was bottled by Douglas Laing in December 2013 with… More info
Yet another lovely Douglas Laing indie bottling, this time featuring whisky from the Auchentoshan distillery in the Lowlands. It was distilled in the not-so-distant past of November 1997 and matured… More info
From Hunter Laing's classic Old Malt Cask range of independently bottled whiskies comes a 16 year old Auchentoshan single malt, presented at 50% ABV. It was distilled in October 1997 and matured in a… More info
Lowland single malt Scotch whisky from the Auchtoshan distillery, bottled by Signatory. This tasty rascal was distilled in December 1997, matured in two bourbon barrel and bottled in February 2014… More info
This single malt from Auchentoshan was released as a limited edition of just 4,800 bottles of cask strength, bourbon cask matured, 16 year old Lowland whisky. More info


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California Carpet
Phone: (415) 487-3636 View Additional Phone Numbers 1197 Folsom St, San Francisco, CA 94103 http://www.calfloor.com
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This company offers supplying and installing of carpet, resilient flooring, hardwood flooring, eco-friendly flooring and rugs.
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9821 Business Park Dr, Sacramento CA 95827
Phone Number: (800) 321-2752
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Business ManagementMr. John Wilson, Owner Ms. Mary Wilson, Owner
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Carpet & Rug Dealers - New Floor Materials - Retail Tile - Ceramic - Contractors & Dealers
Service AreaThis business service area covers: San Francisco, Mill Valley, Sausalito and Tiburon. South of San Francisco, California Carpet serves the entire peninsula including Palo Alto, Los Altos, Menlo Park, Burlingame and Redwood City.
We have stores in San Francisco and San Carlos.


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Tyrese Gibson's Felony Citation Dropped by Prosecutors
Florida prosecutors have dropped a felony citation against actor/singer Tyrese Gibson over a car accident last month in January. The 31-year-old R&B singer was involved in a collision with Sheena McCreary in Miami, Florida on January 4, and both drivers were cited for allegedly leaving the scene of an accident "on public or private property".
Gibson's lawyers contested the charge against their client, insisting Gibson star followed protocol by filing a report with cops. The attorneys filed papers on January 18 entering a not guilty plea on their client's behalf.
The "Sweet Lady" singer and McCreary left the scene of the accident in a taxi together after reporting the crash to cops, according to TMZ.com. Prosecutors officially dropped the case on Tuesday, February 16.
More Tyrese Gibson News
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- Brad Pitt Reportedly Worries About 'Anorexic' and 'Fragile' Angelina Jolie
- Dan Aykroyd on Why 'Ghostbusters' Reboot Is Worth Watching: It Has More Laughs and More Scares


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Pushed to the margins, the company is betting on former Airbus COO Guenter Butschek to revive its fortunes New Delhi: Deep losses and disastrous... ...http://www.livemint.com/Companies/b6ImKxp8WqUnns6PsCyCCI/Can-Tata-Motors-get-its-groove-back.html
Kolkata : Tata Motors, the auto arm of India's salt to aviation conglomerate, on Monday said it is difficult to carry on with the introductory... ...http://www.deccanchronicle.com/business/autos/120416/tiago-may-see-price-hike-later.html
Tata Motors Global customer focus strategy, Horizonext tied up with product theme Play Strong! to build customer satisfaction in Indonesia... ...http://www.pocketnewsalert.com/2013/09/tata-motors-show-offer-smart-and-strong.html
Tata initially offered only the Zest's base XE variant in the 75 PS trim of the 1.3 liter Multijet diesel engine. Rest all the variants were... ...http://motorbash.com/tata-zest-xm-xms-variant-75ps-prices/
Tata Manza is build on the J300...
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Why I Love Trees
Walt Dunlap
Original aphorisms. Very little about trees, even less about fishing.
Writers are the pearl divers of the human spirit.
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