JP2001521889A5 - - Google Patents
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- Publication number
- JP2001521889A5 JP2001521889A5 JP2000518654A JP2000518654A JP2001521889A5 JP 2001521889 A5 JP2001521889 A5 JP 2001521889A5 JP 2000518654 A JP2000518654 A JP 2000518654A JP 2000518654 A JP2000518654 A JP 2000518654A JP 2001521889 A5 JP2001521889 A5 JP 2001521889A5
- Authority
- JP
- Japan
- Prior art keywords
- benzenesulfonamide
- pyrazol
- trifluoromethyl
- compound
- phenyl
- 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.)
- Withdrawn
Links
- -1 cyano, carboxyl Chemical group 0.000 description 78
- 150000001875 compounds Chemical class 0.000 description 28
- 150000003839 salts Chemical class 0.000 description 20
- 125000000217 alkyl group Chemical group 0.000 description 19
- 239000008194 pharmaceutical composition Substances 0.000 description 19
- 125000001188 haloalkyl group Chemical group 0.000 description 14
- 125000005843 halogen group Chemical group 0.000 description 14
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 14
- 125000000753 cycloalkyl group Chemical group 0.000 description 13
- 125000003545 alkoxy group Chemical group 0.000 description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 12
- 125000000623 heterocyclic group Chemical group 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 10
- 125000003282 alkyl amino group Chemical group 0.000 description 9
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 125000004414 alkyl thio group Chemical group 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 description 7
- 125000002971 oxazolyl group Chemical group 0.000 description 7
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 6
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 6
- 125000004966 cyanoalkyl group Chemical group 0.000 description 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 6
- 125000004438 haloalkoxy group Chemical group 0.000 description 6
- 150000004678 hydrides Chemical class 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 125000004181 carboxyalkyl group Chemical group 0.000 description 5
- 125000002883 imidazolyl group Chemical group 0.000 description 5
- 125000000842 isoxazolyl group Chemical group 0.000 description 5
- 125000003226 pyrazolyl group Chemical group 0.000 description 5
- NSQNZEUFHPTJME-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(C(F)(F)F)=N1 NSQNZEUFHPTJME-UHFFFAOYSA-N 0.000 description 4
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 4
- 125000004103 aminoalkyl group Chemical group 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 4
- WAZQAZKAZLXFMK-UHFFFAOYSA-N deracoxib Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 WAZQAZKAZLXFMK-UHFFFAOYSA-N 0.000 description 4
- 125000006003 dichloroethyl group Chemical group 0.000 description 4
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 4
- 125000006001 difluoroethyl group Chemical group 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 125000006343 heptafluoro propyl group Chemical group 0.000 description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- 125000004043 oxo group Chemical group O=* 0.000 description 4
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- TZUKXDRCVJCLLL-UHFFFAOYSA-N 2-methyl-5-[1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazol-2-yl]pyridine Chemical compound C1=NC(C)=CC=C1C1=NC(C(F)(F)F)=CN1C1=CC=C(S(C)(=O)=O)C=C1 TZUKXDRCVJCLLL-UHFFFAOYSA-N 0.000 description 2
- ZJOUYQCSZYKGKU-UHFFFAOYSA-N 3-[1-(4-methylsulfonylphenyl)-4-(trifluoromethyl)imidazol-2-yl]pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1N1C(C=2C=NC=CC=2)=NC(C(F)(F)F)=C1 ZJOUYQCSZYKGKU-UHFFFAOYSA-N 0.000 description 2
- INRQTVDUZFESAO-UHFFFAOYSA-N 4-(3,4-difluorophenyl)-3-(4-methylsulfonylphenyl)-2h-furan-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=C(F)C(F)=CC=2)C(=O)OC1 INRQTVDUZFESAO-UHFFFAOYSA-N 0.000 description 2
- NSRMOHFGSWCCFK-UHFFFAOYSA-N 4-[2-(5-methylpyridin-3-yl)-4-(trifluoromethyl)imidazol-1-yl]benzenesulfonamide Chemical compound CC1=CN=CC(C=2N(C=C(N=2)C(F)(F)F)C=2C=CC(=CC=2)S(N)(=O)=O)=C1 NSRMOHFGSWCCFK-UHFFFAOYSA-N 0.000 description 2
- MQPLMBSDWYIIID-UHFFFAOYSA-N 4-[5-phenyl-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC=CC=2)=CC(C(F)(F)F)=N1 MQPLMBSDWYIIID-UHFFFAOYSA-N 0.000 description 2
- 208000006399 Premature Obstetric Labor Diseases 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000005100 aryl amino carbonyl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 2
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 230000001605 fetal effect Effects 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- TTZNQDOUNXBMJV-UHFFFAOYSA-N mavacoxib Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C=2C=CC(F)=CC=2)=CC(C(F)(F)F)=N1 TTZNQDOUNXBMJV-UHFFFAOYSA-N 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- HKYOGYJVZLWKLN-UHFFFAOYSA-N n-[5-(3,4-difluorophenyl)-2-(trifluoromethyl)-1,3-oxazol-4-yl]benzenesulfonamide Chemical compound C1=C(F)C(F)=CC=C1C1=C(NS(=O)(=O)C=2C=CC=CC=2)N=C(C(F)(F)F)O1 HKYOGYJVZLWKLN-UHFFFAOYSA-N 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 description 1
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000005164 aryl thioalkyl group Chemical group 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000004470 heterocyclooxy group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6388997P | 1997-10-31 | 1997-10-31 | |
| US60/063,889 | 1997-10-31 | ||
| PCT/US1998/022246 WO1999022720A2 (en) | 1997-10-31 | 1998-10-27 | Selective cyclooxygenase-2 inhibitors against premature labor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001521889A JP2001521889A (ja) | 2001-11-13 |
| JP2001521889A5 true JP2001521889A5 (US06815460-20041109-C00023.png) | 2006-01-05 |
Family
ID=22052179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000518654A Withdrawn JP2001521889A (ja) | 1997-10-31 | 1998-10-27 | 早期分娩の治療及び予防中における胎児動脈管の維持にシクロオキシゲナーゼ−２阻害剤を使用する方法 |
Country Status (9)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020188016A9 (en) * | 2000-06-08 | 2002-12-12 | Peterson Johnny W. | Heterocycle derivatives and methods of use |
| ES2275218T3 (es) | 2003-05-07 | 2007-06-01 | Osteologix A/S | Sales de estroncio hidrosolubles para el tratamiento de afecciones de cartilagos y/o huesos. |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2161789A1 (en) * | 1993-05-13 | 1994-11-24 | Jacques Yves Gauthier | 2-substituted-3,4-diarylthiophene derivatives as inhibitors of cyclooxygenase |
| US5474995A (en) * | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
| US5466823A (en) * | 1993-11-30 | 1995-11-14 | G.D. Searle & Co. | Substituted pyrazolyl benzenesulfonamides |
| EP0889724A1 (en) * | 1996-02-27 | 1999-01-13 | Rpms Technology Limited | Cox-2 selective inhibitors for managing labour and uterine contractions |
| US5677318A (en) * | 1996-07-11 | 1997-10-14 | Merck Frosst Canada, Inc. | Diphenyl-1,2-3-thiadiazoles as anti-inflammatory agents |
-
1998
- 1998-10-27 WO PCT/US1998/022246 patent/WO1999022720A2/en active IP Right Grant
- 1998-10-27 CA CA002308639A patent/CA2308639A1/en not_active Abandoned
- 1998-10-27 BR BR9813164-8A patent/BR9813164A/pt not_active Application Discontinuation
- 1998-10-27 JP JP2000518654A patent/JP2001521889A/ja not_active Withdrawn
- 1998-10-27 EP EP98955026A patent/EP1027048A2/en not_active Ceased
- 1998-10-27 AU AU11926/99A patent/AU758566B2/en not_active Ceased
- 1998-10-29 ZA ZA9809876A patent/ZA989876B/xx unknown
- 1998-10-30 TW TW087118094A patent/TW577739B/zh not_active IP Right Cessation
- 1998-10-30 TW TW092134686A patent/TW200404535A/zh unknown
- 1998-10-30 AR ARP980105483A patent/AR014000A1/es not_active Application Discontinuation
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