Source: http://www.google.com/patents/US4590201?dq=7222078
Timestamp: 2017-04-28 01:16:50
Document Index: 695508748

Matched Legal Cases: ['art 24', 'art 24', 'art 18', 'art 18', 'art 16', 'art 16']

Patent US4590201 - 5-amino or substituted amino 1,2,3-triazoles - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inPatentsNovel 5-amino or substituted amino 1,2,3-triazoles are disclosed as having anticoccidial activity. The compounds are useful for controlling coccidiosis when administered in minor quantities to animals, in particular to poultry, usually in admixture with animal sustenance....http://www.google.com/patents/US4590201?utm_source=gb-gplus-sharePatent US4590201 - 5-amino or substituted amino 1,2,3-triazolesAdvanced Patent SearchTry the new Google Patents, with machine-classified Google Scholar results, and Japanese and South Korean patents.Publication numberUS4590201 APublication typeGrantApplication numberUS 06/576,301Publication dateMay 20, 1986Filing dateFeb 2, 1984Priority dateFeb 2, 1984Fee statusPaidAlso published asDE3584100D1, EP0151529A2, EP0151529A3, EP0151529B1Publication number06576301, 576301, US 4590201 A, US 4590201A, US-A-4590201, US4590201 A, US4590201AInventorsRichard J. Bochis, John C. Chabala, Michael H. FisherOriginal AssigneeMerck & Co., Inc.Export CitationBiBTeX, EndNote, RefManPatent Citations (3), Non-Patent Citations (25), Referenced by (35), Classifications (42), Legal Events (4) External Links: USPTO, USPTO Assignment, Espacenet5-amino or substituted amino 1,2,3-triazoles
US 4590201 AAbstract
1. A compound having the formula: ##STR4## wherein: ##STR5## wherein p is 0 to 2; m is 0 to 4; and n is 0 to 5; X is O, S, SO, SO2, CO, CHCN, CH2 or C═NR6 where R6 is hydrogen, loweralkyl, hydroxy, loweralkoxy, amino, loweralkylamino, diloweralkylamino or cyano; and,R4 and R5 are independently halogen, cyano, trifluoromethyl, loweralkanoyl, nitro, loweralkyl, loweralkoxy, carboxy, lowercarbalkoxy, trifluoromethoxy, acetamido, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl, trichlorovinyl, trifluoromethylthio, trifluoromethylsulfinyl, or trifluoromethylsulfonyl; R2 is amino, mono or diloweralkyl amino, acetamido, acetimido, ureido, formamido, formimido or guanidino; and R3 is carbamoyl, cyano, carbazoyl, amidino or N-hydroxycarbamoyl;wherein said loweralkyl, loweralkyl containing, lower alkoxy and loweralkanoyl groups contain from 1 to 3 carbon atoms. 2. The compound of claim 1 wherein p is 1; X is O, S, SO, SO2, CO or C═NR6 wherein R6 is hydrogen, hydroxy, methoxy or cyano;R4 is fluoro, chloro, bromo, methyl, trifluoromethyl, cyano, carbomethoxy, trifluoromethoxy, trifluoromethylthio, or trichlorovinyl; R5 is halogen, methyl, trifluoromethyl, cyano, carbalkoxy, or trichlorovinyl; R2 is amino and R3 is carbamoyl. 3. The compound of claim 2 wherein p is 1; X is S, SO, SO2, CO or C═NR6 wherein R6 is hydrogen, hydroxy, methoxy, or cyano;R4 is one or two substituents ortho to X and are independently fluoro, chloro, methyl, trifluoromethyl, cyano or carbomethoxy; R5 is 1 to 3 substituents meta and/or para to X and which are independently fluoro, chloro, methyl, cyano, carbomethoxy or trichlorovinyl; R2 is amino; and R3 is carbamoyl. 4. The compound of claim 1 which is 5-amino-1-[4-(4-chlorobenzoyl)-3-trifluoromethylbenzyl]-1,2,3-triazole-4-carboxamide.
4-(4-Chlorobenzoyl)toluene
4-(4-Chlorobenzoyl)benzyl bromide
4-(4-Chlorobenzoyl)benzyl azide
5-Amino-1-(4-[4-chlorobenzoyl]benzyl)-1,2,3-triazole-4-carboxamide
3-(4-Chlorobenzoyl)toluene
3-(4-Chlorobenzoyl)benzyl bromide
3-(4-Chlorobenzoyl)benzyl azide
5-Amino-1-(3-[4-chlorobenzoyl]benzyl)-1,2,3-triazole-4-carboxamide
4-(4-Chlorobenzoyl)-3-chlorotoluene
4-(4-Chlorobenzoyl)-3-chlorobenzyl bromide
4-(4-Chlorobenzoyl)-3-chlorobenzyl azide
5-Amino-1-(4-[4-chlorobenzoyl]-3-chlorobenzyl)-1,2,3- triazole-4-carboxamide
3-(4-Chlorobenzoyl)-4-chlorotoluene
3-(4-Chlorobenzoyl)-4-chlorobenzyl bromide
3-(4-Chlorobenzoyl)-4-chlorobenzyl azide
5-Amino-1-(3-[4-chlorobenzoyl]-4-chlorobenzyl)-1,2,3-triazole-4-carboxamide
2,6-Dichloro-4-methylacetanilide
2,6-Dichloro-4-methylbenzonitrile
2,6-Dichloro-4-methylbenzamide
2,6-Dichloro-4-methylbenzoic acid
1-(2,6-Dichloro-4-methylphenyl)-1-(4-chlorophenyl)methyleneimine hydrochloride
4-(t-Butyldimethylsilyloxymethyl)-2,4',6-trichlorobenzophenone
4-(4-Chlorobenzoyl)-3,5-dichlorotoluene
4-(4-Chlorobenzoyl)-3,5-dichlorobenzyl azide
5-Amino-1-(4-[4-chlorobenzoyl]-3,5-dichlorobenzyl)-1,2,3-triazole-4-carboxamide
3-Chloro-4-(4-chlorophenylthio)benzamide
3-Chloro-4-(4-chlorophenylthio)benzyl azide
5-Amino-1-(3-chloro-4-[4-chlorophenylsulfinyl]benzyl-1,2,3-triazole-4-carboxamide
5-Amino-1-(3-chloro-4-[4-chlorophenylsulfonyl]benzyl-1,2,3-triazole-4-carboxamide
4-(4-Chlorophenylthio)-3,5-dichlorobenzamide
4-(4-Chlorophenylthio)-3,5-dichlorobenzylamine
4-(4-Chlorophenylthio)-3,5-dichlorobenzoic acid and 4-(4-Chlorophenylsulfinyl)-3,5-dichlorobenzoic acid
4-(4-Chlorophenylthio)-3,5-dichlorobenzyl alcohol and 4-(4-Chlorophenylsulfinyl)-3,5-dichlorobenzyl alcohol
4-(4-Chlorophenylthio)-3,5-dichlorobenzyl azide
5-Amino-1-(4-[4-chlorophenylthio]-3,5-dichlorobenzyl)1,2,3-triazole-4-carboxamide
5-Amino-1-(4-[4-chlorophenylsulfinyl]-3,5-dichlorobenzyl)-1,2,3-triazole
4-Benzoyl-3-methylbenzyl azide and 2-benzoyl-5-methylbenzyl azide
4-Amino-1-(4-benzoyl-3-methylbenzyl)-1,2,3-triazole-4-carboxamide
2,6-Dichloro-4-methylbenzophenone
4-Benzoyl-3,5-dichlorobenzyl bromide
4-Benzoyl-3,5-dichlorobenzyl azide
5-Amino-1-(4-benzoyl-3,5-dichlorobenzyl)-1,2,3-triazole-4-carboxamide
4-(2,6-Dichlorobenzoyl)toluene
4-(2,6-Dichlorobenzoyl)benzyl bromide
4-(2,6-Dichlorobenzoyl)benzyl azide
5-Amino-1-(4-[2,6-dichlorobenzoyl]benzyl)-1,2,3-triazole-4-carboxamide
4-Chlorobenzoylmesitylene
4-(4-Chlorobenzoyl)- 3,5-dimethylbenzyl azide and 2-(4-chlorobenzoyl)-3,5-dimethylbenzyl azide
5-Amino-1-(4-[4-chlorobenzoyl]-3,5-dimethylbenzyl)-1,2,3-triazole-4-carboxamide
1-(4-Chlorobenzoyl)-2-chloro-4,6-dimethylbenzene and 1-(4-chlorobenzoyl)-4-chloro-2,6-dimethylbenzene
3-Chloro-4-(4-chlorobenzoyl)-5-methylbenzyl)azide and 3-chloro-2-(4-chlorobenzovl)-5-methylbenzyl azide
5-Amino-1-(3-chloro-4-[4-chlorobenzoyl]-5-methylbenzyl)-1,2,3-triazole-4-carboxamide
1-(4-Trifluoromethylbenzoyl)-2-chloro-4,6-dimethylbenzene and 1-(4-trifluoromethylbenzoyl)-4-chloro-2,6-dimethylbenzene
4-(4-Trifluoromethylbenzoyl)-3-chloro-5-methylbenzyl azide and 2-(4-trifluoromethylbenzoyl)-3-chloro-5-methylbenzyl azide
5-Amino-1-(4-[4-trifluoromethylbenzoyl]-3-chloro-5-methylbenzyl)-1,2,3-triazole-4-carboxamide
1-(4-[4-Trifluoromethylbenzoyl]-3-chloro-5-methyl-benzyl)-5-methylamino-1,2,3-triazole-4-carboxamide
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Cupts VI Dimrotarearray. of Triazoles, CA 74 (23): 125581z (1971).* Cited by examinerReferenced byCiting PatentFiling datePublication dateApplicantTitleUS4721791 *May 19, 1986Jan 26, 1988Merck & Co., Inc.5-amino or substituted amino 1,2,3-triazolesUS4752611 *Nov 29, 1985Jun 21, 1988Merck & Co., Inc.Anticoccidial 1,2,3-trazole compoundsUS4816469 *Nov 6, 1987Mar 28, 1989Merck & Co., Inc.5-Amino or substituted amino 1,2,3-triazolesUS4847257 *Aug 20, 1987Jul 11, 1989Merck & Co., Inc.5-Amino or substituted amino 1,2,3,-triazoles useful as antiproliferative agentsUS4923885 *Aug 19, 1988May 8, 1990Merck & Co., Inc.5-amino-1-(4-naphthoylbenzyl)-1,2,3-triazole-4-carboxamides and analogs as antiproliferative agentsUS4950673 *Aug 18, 1988Aug 21, 1990Merck & Co., Inc.5-amino or substituted amino 1,2,3-triazolesUS5015651 *Dec 6, 1988May 14, 1991E. I. Du Pont De Nemours And CompanyTreatment of hypertension with 1,2,4-angiotensin II antagonistsUS5045543 *May 8, 1989Sep 3, 1991Merck & Co., Inc.5-amino or substituted amino 1,2,3-triazoles useful as antimetastatic agentsUS5081127 *Mar 26, 1990Jan 14, 1992E. I. Du Pont De Nemours And CompanySubstituted 1,2,3-triazole angiotensin II antagonistsUS5093346 *Mar 8, 1991Mar 3, 1992E. I. Du Pont De Nemours And CompanySubstituted 1,2,4-triazole angiotensin II antagonistsUS5189048 *Jul 10, 1991Feb 23, 1993E. I. Du Pont De Nemours And CompanySubstituted 1,2,3 triazole angiotensin II antagonistsUS5315013 *Aug 5, 1992May 24, 1994E. I. Du Pont De Nemours And CompanySubstituted pyrazole angiotensin II antagonistsUS5405782 *Mar 31, 1993Apr 11, 1995The United States Of America As Represented By The Secretary Of The Department Of Health And Human ServicesDetection and quantitation method for therapeutic agents in bloodUS5482954 *Jul 1, 1994Jan 9, 1996The United States Of America As Represented By The Department Of Health And Human ServicesSignal transduction inhibitor triazole and diazole compoundsUS5498620 *May 31, 1995Mar 12, 1996The United States Of America As Represented By The Department Of Health And Human ServicesSignal transduction inhibitor 1,2,3-triazolo compoundsUS5602156 *Mar 10, 1994Feb 11, 1997The United States Of America As Represented By The Department Of Health And Human ServicesMethod for inhibiting metalloproteinase expressionUS5705514 *May 31, 1995Jan 6, 1998The United States Of America As Represented By The Department Of Health And Human ServicesSignal transduction inhibitor compoundsUS5744492 *Mar 10, 1994Apr 28, 1998United States Of AmericaMethod for inhibiting angiogenesisUS5861406 *Jul 18, 1996Jan 19, 1999Constantia GruppeTreatment and prevention of neoplasms with salts of aminoimidazole carboxamide and 5-amino or substituted amino 1,2,3-triazolesUS5880129 *Aug 5, 1997Mar 9, 1999The United States Of America As Represented By The Department Of Health And Human ServicesMethods of inhibiting invasion and metastasis of malignant solid tumorsUS5912346 *Nov 10, 1997Jun 15, 1999Constantia GruppeTreatment and prevention of neoplasms with salts of aminoimidazole carboxamide and 5-amino or substituted amino 1,2,3-triazolesUS6239137Jan 15, 1999May 29, 2001Savvipharm IncSalts of aminoimidazole carboxamide and 5 amino or substituted amino 1,2,3-triazole, induce apoptosis, inhibit DNA synthesis and control cyclooxygenase activityUS7276050Mar 2, 2004Oct 2, 2007Alan FranklinTrans-scleral drug delivery method and apparatusUS8377973 *Sep 3, 2010Feb 19, 2013Tactical Therapeutics IncCompositions and processes for preparing 5-amino or substituted amino 1,2,3-triazoles and triazole orotate formulationsUS8614235Jul 13, 2011Dec 24, 2013Rfe Pharma LlcCAI-based systems and methods for the localized treatment of ocular and other diseasesUS8912223Jan 16, 2013Dec 16, 2014Tactical Therapeutics IncCompositions and processes for preparing 5-amino or substituted amino 1,2,3-triazoles and triazoles orotate formulationsUS20060116404 *Sep 26, 2005Jun 1, 2006Gary RobinsonCAI-based systems and methods for the localized treatment of ocular and other diseasesUS20110060142 *Sep 3, 2010Mar 10, 2011Karmali Rashida ANovel compositions and processes for preparing 5-amino or substituted amino 1,2,3-triazoles and triazole orotate formulationsCN100493609CJan 19, 2005Jun 3, 2009中国医学科学院基础医学研究所Medicine composition for treating malignant tumours and applicationCN104817507A *Sep 3, 2010Aug 5, 2015巧妙疗法股份有限公司Novel compositions and processes for preparing 5-amino or substituted amino 1,2,3-triazoles and triazole orotate formulationsEP2963023A1Sep 3, 2010Jan 6, 2016Tactical Therapeutics Inc.Process for preparing 5-amino-1, 2, 3-triazole orotate derivativesWO1990014009A1 *May 18, 1990Nov 29, 1990The United States Of America, As Represented By The Secretary, U.S. Department Of CommerceTherapeutic application of an anti-invasion compoundWO2006037106A2Sep 26, 2005Apr 6, 2006Rfe Pharma LlcCarboxy-amido-triazoles for the localized treatment of ocular diseasesWO2006076854A1 *Jan 10, 2006Jul 27, 2006Institute Of Basic Medical Sciences, Chinese Academy Of Medical SciencesCombination medication for malignant tumors and applicationWO2011028288A1Sep 3, 2010Mar 10, 2011Tactical Therapeutics, IncNovel compositions and processes for preparing 5-amino or substituted amino 1,2,3-triazoles and triazole orotate formulations* Cited by examinerClassifications U.S. Classification514/359, 548/255International ClassificationC07D249/06, C07F7/18, C07C49/813, C07C63/70, C07C45/67, A01N43/36, A61P33/02, C07C45/63, C07C45/45, C07D249/04, C07C45/46, A61K31/41, C07C45/42Cooperative ClassificationC07D249/06, C07C317/00, C07D249/04, C07C247/00, C07C45/42, C07C45/46, C07C323/00, C07C45/673, C07C45/45, C07F7/1852, C07C45/63, C07C49/813, C07C255/00European ClassificationC07C255/00, C07C247/00, C07C323/00, C07C317/00, C07C45/42, C07C45/67C, C07C45/45, C07C45/46, C07C45/63, C07F7/18C4D4C, C07C63/70, C07D249/04, C07D249/06, C07C49/813Legal EventsDateCodeEventDescriptionJan 21, 1986ASAssignmentOwner name: MERCK & CO., INC., LINCOLN AVENUE, RAHWAY, NEW JERFree format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:BOCHIS, RICHARD J.;CHABALA, JOHN C.;FISHER, MICHAEL H.;REEL/FRAME:004517/0637Effective date: 19840125Owner name: MERCK & CO., INC., A CORP. OF NEW JERSEY,NEW JERSEFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:BOCHIS, RICHARD J.;CHABALA, JOHN C.;FISHER, MICHAEL H.;REEL/FRAME:004517/0637Effective date: 19840125Oct 19, 1989FPAYFee paymentYear of fee payment: 4Oct 22, 1993FPAYFee paymentYear of fee payment: 8Oct 17, 1997FPAYFee paymentYear of fee payment: 12RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services