JP2003516975A5 - - Google Patents
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- Publication number
- JP2003516975A5 JP2003516975A5 JP2001544697A JP2001544697A JP2003516975A5 JP 2003516975 A5 JP2003516975 A5 JP 2003516975A5 JP 2001544697 A JP2001544697 A JP 2001544697A JP 2001544697 A JP2001544697 A JP 2001544697A JP 2003516975 A5 JP2003516975 A5 JP 2003516975A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclopropyl
- alkyl
- propyl
- methylphenyl
- amine hydrochloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 19
- -1 methylenedioxy Chemical group 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 6
- 229910005965 SO 2 Inorganic materials 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 4
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- PVPTUASRAVWKGX-UHFFFAOYSA-N 1,2-dihydrotriazol-3-amine Chemical compound NN1NNC=C1 PVPTUASRAVWKGX-UHFFFAOYSA-N 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
- 150000004677 hydrates Chemical class 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- PWSFZDMKNKEILM-BDQAORGHSA-N 1-(2,4-dichlorophenyl)-5-ethyl-n-[(1s)-1-phenylbutyl]-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.CCCN([C@@H](CCC)C=1C=CC=CC=1)C(=N1)N=C(CC)N1C1=CC=C(Cl)C=C1Cl PWSFZDMKNKEILM-BDQAORGHSA-N 0.000 claims 1
- AJCMNLUWKLXWQG-UHFFFAOYSA-N 1-(2-chloro-4-methoxy-5-methylphenyl)-5-cyclopropyl-n-(2-cyclopropyl-1-phenylethyl)-n-prop-2-ynyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C1=C(C)C(OC)=CC(Cl)=C1N1C(C2CC2)=NC(N(CC#C)C(CC2CC2)C=2C=CC=CC=2)=N1 AJCMNLUWKLXWQG-UHFFFAOYSA-N 0.000 claims 1
- CZRJUWGPYDDDHQ-UHFFFAOYSA-N 1-(2-chloro-4-methoxy-5-methylphenyl)-5-cyclopropyl-n-(2-cyclopropyl-1-phenylethyl)-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.N1=C(C2CC2)N(C=2C(=CC(OC)=C(C)C=2)Cl)N=C1N(CCC)C(C=1C=CC=CC=1)CC1CC1 CZRJUWGPYDDDHQ-UHFFFAOYSA-N 0.000 claims 1
- MVWDDZGGGHOGQO-FTBISJDPSA-N 1-(2-chloro-4-methoxy-5-methylphenyl)-5-cyclopropyl-n-[(1r)-1-(4-fluorophenyl)-2-methoxyethyl]-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C1([C@H](COC)N(CCC)C2=NN(C(C3CC3)=N2)C=2C(=CC(OC)=C(C)C=2)Cl)=CC=C(F)C=C1 MVWDDZGGGHOGQO-FTBISJDPSA-N 0.000 claims 1
- SWZXDYHQMYVVBM-JIDHJSLPSA-N 1-(2-chloro-4-methoxy-5-methylphenyl)-5-cyclopropyl-n-[(1s)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-n-prop-2-ynyl-1,2,4-triazol-3-amine;hydrobromide Chemical compound Br.C1=C(C)C(OC)=CC(Cl)=C1N1C(C2CC2)=NC(N(CC#C)[C@@H](CC2CC2)C=2C=C(F)C(C)=CC=2)=N1 SWZXDYHQMYVVBM-JIDHJSLPSA-N 0.000 claims 1
- JMBPFABNJHVOCR-JIDHJSLPSA-N 1-(2-chloro-4-methoxy-5-methylphenyl)-5-cyclopropyl-n-[(1s)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C([C@H](N(CCC)C1=NN(C(C2CC2)=N1)C=1C(=CC(OC)=C(C)C=1)Cl)C=1C=C(F)C(C)=CC=1)C1CC1 JMBPFABNJHVOCR-JIDHJSLPSA-N 0.000 claims 1
- VTOYLWIFVFRYHF-UHFFFAOYSA-N 1-(2-chloro-4-methoxy-5-methylphenyl)-5-cyclopropyl-n-[2-cyclopropyl-1-(4-fluorophenyl)ethyl]-n-prop-2-ynyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C1=C(C)C(OC)=CC(Cl)=C1N1C(C2CC2)=NC(N(CC#C)C(CC2CC2)C=2C=CC(F)=CC=2)=N1 VTOYLWIFVFRYHF-UHFFFAOYSA-N 0.000 claims 1
- FVXJMWZVSNUDJY-UHFFFAOYSA-N 1-(2-chloro-4-methoxy-5-methylphenyl)-5-cyclopropyl-n-[2-cyclopropyl-1-(4-fluorophenyl)ethyl]-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.N1=C(C2CC2)N(C=2C(=CC(OC)=C(C)C=2)Cl)N=C1N(CCC)C(C=1C=CC(F)=CC=1)CC1CC1 FVXJMWZVSNUDJY-UHFFFAOYSA-N 0.000 claims 1
- YKOUFOAKCBVIHB-BOXHHOBZSA-N 1-(2-chloro-4-methoxy-5-methylphenyl)-5-methyl-n-[(1s)-1-phenylbutyl]-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.CCCN([C@@H](CCC)C=1C=CC=CC=1)C(=N1)N=C(C)N1C1=CC(C)=C(OC)C=C1Cl YKOUFOAKCBVIHB-BOXHHOBZSA-N 0.000 claims 1
- WFYZDLUMPWFTSR-BQAIUKQQSA-N 1-(2-chloro-4-methoxy-5-methylphenyl)-n-[(1s)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-5-ethyl-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C([C@H](N(CCC)C1=NN(C(CC)=N1)C=1C(=CC(OC)=C(C)C=1)Cl)C=1C=C(F)C(C)=CC=1)C1CC1 WFYZDLUMPWFTSR-BQAIUKQQSA-N 0.000 claims 1
- DTBFUKFUWJFYGL-BQAIUKQQSA-N 1-(2-chloro-4-methoxy-5-methylphenyl)-n-[(1s)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-5-methyl-n-prop-2-ynyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C1=C(C)C(OC)=CC(Cl)=C1N1C(C)=NC(N(CC#C)[C@@H](CC2CC2)C=2C=C(F)C(C)=CC=2)=N1 DTBFUKFUWJFYGL-BQAIUKQQSA-N 0.000 claims 1
- MPPGXEYBOMGQIC-BQAIUKQQSA-N 1-(2-chloro-4-methoxy-5-methylphenyl)-n-[(1s)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-5-methyl-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C([C@H](N(CCC)C1=NN(C(C)=N1)C=1C(=CC(OC)=C(C)C=1)Cl)C=1C=C(F)C(C)=CC=1)C1CC1 MPPGXEYBOMGQIC-BQAIUKQQSA-N 0.000 claims 1
- NLTHNJUIHGELQW-UHFFFAOYSA-N 1-(2-chloro-4-methoxy-5-methylphenyl)-n-[2-cyclopropyl-1-(4-fluorophenyl)ethyl]-5-methyl-n-prop-2-ynyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C1=C(C)C(OC)=CC(Cl)=C1N1C(C)=NC(N(CC#C)C(CC2CC2)C=2C=CC(F)=CC=2)=N1 NLTHNJUIHGELQW-UHFFFAOYSA-N 0.000 claims 1
- XUQASNHMDWEVHJ-UHFFFAOYSA-N 1-(2-chloro-4-methylsulfanylphenyl)-n-[2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-5-methyl-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.N1=C(C)N(C=2C(=CC(SC)=CC=2)Cl)N=C1N(CCC)C(C=1C=C(F)C(C)=CC=1)CC1CC1 XUQASNHMDWEVHJ-UHFFFAOYSA-N 0.000 claims 1
- NEURYOYRKPFLKH-UHFFFAOYSA-N 2-chloro-1-isocyanato-4-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=C(N=C=O)C(Cl)=C1 NEURYOYRKPFLKH-UHFFFAOYSA-N 0.000 claims 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 1
- HWQKGVPWMDGCTJ-BOXHHOBZSA-N 5-cyclopropyl-1-(2,4-dichlorophenyl)-n-[(1r)-1-(4-fluorophenyl)-2-methoxyethyl]-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C1([C@H](COC)N(CCC)C2=NN(C(C3CC3)=N2)C=2C(=CC(Cl)=CC=2)Cl)=CC=C(F)C=C1 HWQKGVPWMDGCTJ-BOXHHOBZSA-N 0.000 claims 1
- PZSMXSNSKGLUSK-FTBISJDPSA-N 5-cyclopropyl-1-(2,4-dichlorophenyl)-n-[(1s)-1-(4-methylphenyl)butyl]-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.CCCN([C@@H](CCC)C=1C=CC(C)=CC=1)C(=NN1C=2C(=CC(Cl)=CC=2)Cl)N=C1C1CC1 PZSMXSNSKGLUSK-FTBISJDPSA-N 0.000 claims 1
- KQELBZSXYJCFJI-UHFFFAOYSA-N 5-cyclopropyl-n-(2-cyclopropyl-1-phenylethyl)-1-(2,4-dichlorophenyl)-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.N1=C(C2CC2)N(C=2C(=CC(Cl)=CC=2)Cl)N=C1N(CCC)C(C=1C=CC=CC=1)CC1CC1 KQELBZSXYJCFJI-UHFFFAOYSA-N 0.000 claims 1
- AATNXRAPUFLVHI-SNYZSRNZSA-N 5-cyclopropyl-n-[(1s)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-1-(2,4-dimethylphenyl)-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C([C@H](N(CCC)C1=NN(C(C2CC2)=N1)C=1C(=CC(C)=CC=1)C)C=1C=C(F)C(C)=CC=1)C1CC1 AATNXRAPUFLVHI-SNYZSRNZSA-N 0.000 claims 1
- UMKBWCOXZVINFP-UHFFFAOYSA-N 5-cyclopropyl-n-[2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-1-(2,4-dichlorophenyl)-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.N1=C(C2CC2)N(C=2C(=CC(Cl)=CC=2)Cl)N=C1N(CCC)C(C=1C=C(F)C(C)=CC=1)CC1CC1 UMKBWCOXZVINFP-UHFFFAOYSA-N 0.000 claims 1
- UFFYEDWIGUERRK-UHFFFAOYSA-N 5-cyclopropyl-n-[2-cyclopropyl-1-(4-fluorophenyl)ethyl]-1-(2,4-dichlorophenyl)-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.N1=C(C2CC2)N(C=2C(=CC(Cl)=CC=2)Cl)N=C1N(CCC)C(C=1C=CC(F)=CC=1)CC1CC1 UFFYEDWIGUERRK-UHFFFAOYSA-N 0.000 claims 1
- XIZCEGGBNOKHRK-UHFFFAOYSA-N 5-cyclopropyl-n-[2-cyclopropyl-1-(4-fluorophenyl)ethyl]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-n-propyl-1,2,4-triazol-3-amine;hydrobromide Chemical compound Br.N1=C(C2CC2)N(C=2C(=CC(=CC=2Cl)C(F)(F)F)Cl)N=C1N(CCC)C(C=1C=CC(F)=CC=1)CC1CC1 XIZCEGGBNOKHRK-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- JZCCEJPJPWXSJU-FTBISJDPSA-N n-[(1s)-2-cyclopropyl-1-(4-fluorophenyl)ethyl]-1-(2,4-dichlorophenyl)-5-ethyl-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C([C@H](N(CCC)C1=NN(C(CC)=N1)C=1C(=CC(Cl)=CC=1)Cl)C=1C=CC(F)=CC=1)C1CC1 JZCCEJPJPWXSJU-FTBISJDPSA-N 0.000 claims 1
- UYYYAXJPBMJQFA-FTBISJDPSA-N n-[(1s)-2-cyclopropyl-1-(4-fluorophenyl)ethyl]-1-(2,4-dichlorophenyl)-5-methyl-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C([C@H](N(CCC)C1=NN(C(C)=N1)C=1C(=CC(Cl)=CC=1)Cl)C=1C=CC(F)=CC=1)C1CC1 UYYYAXJPBMJQFA-FTBISJDPSA-N 0.000 claims 1
- IVMWPMNCYQEPFS-UHFFFAOYSA-N n-[2-cyclopropyl-1-(4-fluorophenyl)ethyl]-1-(2,4-dichlorophenyl)-5-(methoxymethyl)-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.N1=C(COC)N(C=2C(=CC(Cl)=CC=2)Cl)N=C1N(CCC)C(C=1C=CC(F)=CC=1)CC1CC1 IVMWPMNCYQEPFS-UHFFFAOYSA-N 0.000 claims 1
- FXJFOIYJZQPVHA-UHFFFAOYSA-N n-[2-cyclopropyl-1-(4-fluorophenyl)ethyl]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-methyl-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.N1=C(C)N(C=2C(=CC(=CC=2Cl)C(F)(F)F)Cl)N=C1N(CCC)C(C=1C=CC(F)=CC=1)CC1CC1 FXJFOIYJZQPVHA-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9915935A FR2802530B1 (fr) | 1999-12-17 | 1999-12-17 | Nouveaux derives amino substitues ramifies du 3-amino-1-phenyl-1h[1,2,4]triazole, procedes pour leur preparation et compositions pharmaceutiques les contenant |
| FR99/15935 | 1999-12-17 | ||
| PCT/FR2000/003536 WO2001044207A2 (fr) | 1999-12-17 | 2000-12-14 | Nouveaux derives amino substitues ramifies du 3-amino-1-phenyl-1h[1,2 4]triazole, procedes pour leur preparation et compositions pharmaceutiques les contenant |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003516975A JP2003516975A (ja) | 2003-05-20 |
| JP2003516975A5 true JP2003516975A5 (enExample) | 2005-09-29 |
| JP4146641B2 JP4146641B2 (ja) | 2008-09-10 |
Family
ID=9553380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001544697A Expired - Lifetime JP4146641B2 (ja) | 1999-12-17 | 2000-12-14 | ３−アミノ−１−フェニル−１ｈ−［１，２，４］トリアゾールの新規な分岐状置換アミノ誘導体、それらの製造法およびそれらを含む医薬組成物 |
Country Status (33)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7226920B2 (en) * | 2003-08-06 | 2007-06-05 | Vertex Pharmaceuticals Inc. | Aminotriazole compounds useful as inhibitors of protein kinases |
| JO3019B1 (ar) | 2006-04-19 | 2016-09-05 | Janssen Pharmaceutica Nv | ثلاثي مستبدل 4،2،1-ثلاثي زولات |
| ES2424023T3 (es) | 2007-10-18 | 2013-09-26 | Janssen Pharmaceutica N.V. | 1,2,4-triazoles trisustituidos |
| JO2784B1 (en) | 2007-10-18 | 2014-03-15 | شركة جانسين فارماسوتيكا ان. في | 5,3,1 - Triazole substitute derivative |
| MY152486A (en) * | 2008-03-19 | 2014-10-15 | Janssen Pharmaceutica Nv | Trisubstituted 1,2,4 - triazoles as nicotinic acetylcholine receptor modulators |
| US8779158B2 (en) | 2008-05-09 | 2014-07-15 | Janssen Pharmaceutica Nv | Trisubstituted pyrazoles as acetylcholine receptor modulators |
| EP2629616A4 (en) * | 2010-10-21 | 2014-03-26 | Merck Sharp & Dohme | SUBSTITUTED AMINO-TRIAZOLYL-PDE10-HEMMER |
| LT3096756T (lt) | 2014-01-21 | 2024-08-26 | Neurocrine Biosciences, Inc. | Crf1 receptoriaus antagonistai, skirti įgimtos antinksčių hiperplazijos gydymui |
| CN104059027B (zh) * | 2014-07-01 | 2015-10-28 | 河北大学 | 一类含1,2,4-三唑的(e)-甲氧基亚氨基苯乙酸甲酯类化合物及其制备方法和用途 |
| FI3984523T3 (fi) | 2018-12-07 | 2025-10-21 | Neurocrine Biosciences Inc | Crf1-reseptorin antagonisti, lääkeformulaatioita ja niiden kiinteitä muotoja synnynnäisen lisämunuaisten liikakasvun hoitoon |
| KR20220069008A (ko) * | 2019-09-25 | 2022-05-26 | 온코아렌디 테라퓨틱스 에스.에이. | 5-(4-((2s,5s)-5-(4-클로로벤질)-2-메틸모르폴리노)피페리딘-1-일)-1h-1,2,4-트리아졸-3-아민의 생성 방법 |
| CA3152590A1 (en) | 2019-09-27 | 2021-04-01 | Evan Smith | Crf receptor antagonists and methods of use |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3869167D1 (de) * | 1987-03-27 | 1992-04-23 | Kumiai Chemical Industry Co | Phenyltriazol-derivate und insectizid. |
| US5795905A (en) * | 1995-06-06 | 1998-08-18 | Neurocrine Biosciences, Inc. | CRF receptor antagonists and methods relating thereto |
| FR2763337B1 (fr) * | 1997-05-13 | 1999-08-20 | Sanofi Sa | Nouveaux derives du triazole, un procede pour leur preparation et compositions pharmaceutiques les contenant |
-
1999
- 1999-12-17 FR FR9915935A patent/FR2802530B1/fr not_active Expired - Fee Related
-
2000
- 2000-12-14 EA EA200200523A patent/EA004957B1/ru not_active IP Right Cessation
- 2000-12-14 MX MXPA02006033A patent/MXPA02006033A/es active IP Right Grant
- 2000-12-14 UA UA2002064623A patent/UA73333C2/uk unknown
- 2000-12-14 AU AU25259/01A patent/AU780711B2/en not_active Ceased
- 2000-12-14 JP JP2001544697A patent/JP4146641B2/ja not_active Expired - Lifetime
- 2000-12-14 BR BR0017023-2A patent/BR0017023A/pt active Search and Examination
- 2000-12-14 CA CA2398772A patent/CA2398772C/fr not_active Expired - Fee Related
- 2000-12-14 CO CO00095200A patent/CO5251379A1/es not_active Application Discontinuation
- 2000-12-14 ES ES00988916T patent/ES2219436T3/es not_active Expired - Lifetime
- 2000-12-14 WO PCT/FR2000/003536 patent/WO2001044207A2/fr not_active Ceased
- 2000-12-14 HU HU0204080A patent/HUP0204080A3/hu unknown
- 2000-12-14 DK DK00988916T patent/DK1242389T3/da active
- 2000-12-14 EP EP00988916A patent/EP1242389B1/fr not_active Expired - Lifetime
- 2000-12-14 PT PT00988916T patent/PT1242389E/pt unknown
- 2000-12-14 IL IL15003700A patent/IL150037A0/xx active IP Right Grant
- 2000-12-14 AT AT00988916T patent/ATE264847T1/de active
- 2000-12-14 EE EEP200200331A patent/EE04778B1/xx not_active IP Right Cessation
- 2000-12-14 DE DE60010126T patent/DE60010126T2/de not_active Expired - Lifetime
- 2000-12-14 TR TR2004/01775T patent/TR200401775T4/xx unknown
- 2000-12-14 PL PL355811A patent/PL203819B1/pl not_active IP Right Cessation
- 2000-12-14 ME MEP-121/08A patent/MEP12108A/xx unknown
- 2000-12-14 RS YUP-439/02A patent/RS50289B/sr unknown
- 2000-12-14 SK SK850-2002A patent/SK285994B6/sk not_active IP Right Cessation
- 2000-12-14 CZ CZ20022099A patent/CZ302460B6/cs not_active IP Right Cessation
- 2000-12-14 US US10/149,499 patent/US6806282B2/en not_active Expired - Lifetime
- 2000-12-14 TR TR2002/01600T patent/TR200201600T2/xx unknown
- 2000-12-14 KR KR1020027007736A patent/KR100705525B1/ko not_active Expired - Fee Related
- 2000-12-14 CN CNB00819078XA patent/CN1293061C/zh not_active Expired - Fee Related
- 2000-12-15 AR ARP000106666A patent/AR031837A1/es not_active Application Discontinuation
-
2001
- 2001-01-29 TW TW089126997A patent/TWI289554B/zh not_active IP Right Cessation
-
2002
- 2002-05-04 IL IL150037A patent/IL150037A/en not_active IP Right Cessation
- 2002-05-28 IS IS6402A patent/IS2315B/is unknown
- 2002-06-03 ZA ZA200204422A patent/ZA200204422B/en unknown
- 2002-06-13 NO NO20022828A patent/NO20022828L/no not_active Application Discontinuation
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