JP2002516909A5 - - Google Patents
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- JP2002516909A5 JP2002516909A5 JP2000552097A JP2000552097A JP2002516909A5 JP 2002516909 A5 JP2002516909 A5 JP 2002516909A5 JP 2000552097 A JP2000552097 A JP 2000552097A JP 2000552097 A JP2000552097 A JP 2000552097A JP 2002516909 A5 JP2002516909 A5 JP 2002516909A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- nhc
- phenyl
- heterocyclic group
- halogen
- 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.)
- Pending
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- -1 C1-6Alkyl Chemical group 0.000 description 40
- 125000000623 heterocyclic group Chemical group 0.000 description 33
- 229910052736 halogen Inorganic materials 0.000 description 29
- 150000002367 halogens Chemical class 0.000 description 29
- 125000000217 alkyl group Chemical group 0.000 description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 8
- 125000002837 carbocyclic group Chemical group 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000004663 dialkyl amino group Chemical group 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000003226 pyrazolyl group Chemical group 0.000 description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 4
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 4
- 125000006217 methyl sulfide group Chemical group [H]C([H])([H])S* 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 description 1
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- YMJLEPMVGQBLHL-UHFFFAOYSA-N 1h-pyrazole-5-carbonitrile Chemical compound N#CC1=CC=NN1 YMJLEPMVGQBLHL-UHFFFAOYSA-N 0.000 description 1
- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical class NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 description 1
- AHXBNAYSJKHAGO-UHFFFAOYSA-N 2-(4-nitrophenyl)-5-pyridin-3-ylpyrazole-3-carboxamide Chemical compound NC(=O)C1=CC(C=2C=NC=CC=2)=NN1C1=CC=C([N+]([O-])=O)C=C1 AHXBNAYSJKHAGO-UHFFFAOYSA-N 0.000 description 1
- SLJXCMIFADRNKB-UHFFFAOYSA-N 2-[4-(2,3-dihydro-1h-inden-2-ylmethylamino)phenyl]-5-pyridin-3-ylpyrazole-3-carbonitrile Chemical compound N=1N(C=2C=CC(NCC3CC4=CC=CC=C4C3)=CC=2)C(C#N)=CC=1C1=CC=CN=C1 SLJXCMIFADRNKB-UHFFFAOYSA-N 0.000 description 1
- CRAWFJBJQNWWJG-UHFFFAOYSA-N 2-[4-[(2,6-dimethylphenyl)methylamino]phenyl]-5-pyridin-3-ylpyrazole-3-carbonitrile Chemical compound CC1=CC=CC(C)=C1CNC1=CC=C(N2C(=CC(=N2)C=2C=NC=CC=2)C#N)C=C1 CRAWFJBJQNWWJG-UHFFFAOYSA-N 0.000 description 1
- PSEZMBBKILHUCM-UHFFFAOYSA-N 2-[4-[(2-chloro-6-fluorophenyl)methylamino]phenyl]-5-pyridin-3-ylpyrazole-3-carbonitrile Chemical compound FC1=CC=CC(Cl)=C1CNC1=CC=C(N2C(=CC(=N2)C=2C=NC=CC=2)C#N)C=C1 PSEZMBBKILHUCM-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- CDMNFVCQZPYYDK-UHFFFAOYSA-N 4-(3-cyanopropoxy)-n-[4-(5-cyano-3-pyridin-3-ylpyrazol-1-yl)phenyl]benzamide Chemical compound C=1C=C(OCCCC#N)C=CC=1C(=O)NC(C=C1)=CC=C1N(C(=C1)C#N)N=C1C1=CC=CN=C1 CDMNFVCQZPYYDK-UHFFFAOYSA-N 0.000 description 1
- YFSFKZHKICGCJW-UHFFFAOYSA-N 4-(5-ethyl-3-pyridin-3-ylpyrazol-1-yl)-n-[(2-fluoro-6-methylphenyl)methyl]aniline Chemical compound CCC1=CC(C=2C=NC=CC=2)=NN1C(C=C1)=CC=C1NCC1=C(C)C=CC=C1F YFSFKZHKICGCJW-UHFFFAOYSA-N 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 0 Cc(c(*)c1*)n[n]1-c(cc1)ccc1I* Chemical compound Cc(c(*)c1*)n[n]1-c(cc1)ccc1I* 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino 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
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- ZADSMLIXHMTDJK-UHFFFAOYSA-N ethyl 2,4-dioxo-4-pyridin-3-ylbutanoate Chemical compound CCOC(=O)C(=O)CC(=O)C1=CC=CN=C1 ZADSMLIXHMTDJK-UHFFFAOYSA-N 0.000 description 1
- LBCFPECTPJNANE-UHFFFAOYSA-N ethyl 2-(4-nitrophenyl)-5-pyridin-3-ylpyrazole-3-carboxylate Chemical compound CCOC(=O)C1=CC(C=2C=NC=CC=2)=NN1C1=CC=C([N+]([O-])=O)C=C1 LBCFPECTPJNANE-UHFFFAOYSA-N 0.000 description 1
- PHRDPBKZRMDSTI-UHFFFAOYSA-N ethyl 3-pyridin-3-yl-1h-pyrazole-5-carboxylate Chemical compound N1C(C(=O)OCC)=CC(C=2C=NC=CC=2)=N1 PHRDPBKZRMDSTI-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000004073 interleukin-2 production Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- KRXOZGYPZZPATG-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-ylmethyl)-4-(5-ethyl-3-pyridin-3-ylpyrazol-1-yl)aniline Chemical compound N=1N(C=2C=CC(NCC3CC4=CC=CC=C4C3)=CC=2)C(CC)=CC=1C1=CC=CN=C1 KRXOZGYPZZPATG-UHFFFAOYSA-N 0.000 description 1
- ROIPYAZETGHHCJ-UHFFFAOYSA-N n-[4-(5-ethyl-3-pyridin-3-ylpyrazol-1-yl)phenyl]-1-methylindole-2-carboxamide Chemical compound N=1N(C=2C=CC(NC(=O)C=3N(C4=CC=CC=C4C=3)C)=CC=2)C(CC)=CC=1C1=CC=CN=C1 ROIPYAZETGHHCJ-UHFFFAOYSA-N 0.000 description 1
- CCAFHMPMIJBDRP-UHFFFAOYSA-N n-[4-(5-ethyl-3-pyridin-3-ylpyrazol-1-yl)phenyl]pyridine-3-carboxamide Chemical compound CCC1=CC(C=2C=NC=CC=2)=NN1C(C=C1)=CC=C1NC(=O)C1=CC=CN=C1 CCAFHMPMIJBDRP-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- LQNUZADURLCDLV-IDEBNGHGSA-N nitrobenzene Chemical group [O-][N+](=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 LQNUZADURLCDLV-IDEBNGHGSA-N 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8815498P | 1998-06-05 | 1998-06-05 | |
| US60/088,154 | 1998-06-05 | ||
| PCT/US1999/012295 WO1999062885A1 (en) | 1998-06-05 | 1999-06-03 | Substituted 1-(4-aminophenyl)pyrazoles and their use as anti-inflammatory agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002516909A JP2002516909A (ja) | 2002-06-11 |
| JP2002516909A5 true JP2002516909A5 (enExample) | 2006-07-27 |
Family
ID=22209668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000552097A Pending JP2002516909A (ja) | 1998-06-05 | 1999-06-03 | 置換１−（４−アミノフェニル）ピラゾール及び抗炎症剤としてのそれらの使用 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6506747B1 (enExample) |
| JP (1) | JP2002516909A (enExample) |
| AU (1) | AU4229999A (enExample) |
| CA (1) | CA2332957A1 (enExample) |
| WO (1) | WO1999062885A1 (enExample) |
Families Citing this family (90)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| TR200102817T2 (tr) * | 1999-03-12 | 2002-05-21 | Boehringer Ingelheim Pharmaceuticals, Inc. | Antiinflamatuar ajanlar olarak faydalı bileşikler |
| EP1466906A1 (en) * | 1999-03-12 | 2004-10-13 | Boehringer Ingelheim Pharmaceuticals Inc. | Heterocyclic urea and related compounds useful as anti-inflammatory agents |
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| WO2002053544A1 (en) * | 2000-12-29 | 2002-07-11 | Darwin Discovery Ltd. | Pharmaceutical uses and synthesis of nicotinanilide-n-oxides |
| US7105682B2 (en) | 2001-01-12 | 2006-09-12 | Amgen Inc. | Substituted amine derivatives and methods of use |
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| CN1325491C (zh) * | 2002-08-27 | 2007-07-11 | 安斯泰来制药有限公司 | 新颖结晶 |
| WO2004050632A1 (en) * | 2002-12-02 | 2004-06-17 | Fujisawa Pharmaceutical Co., Ltd. | Pyrazole derivatives useful as cox-i inhibitors |
| US7491827B2 (en) | 2002-12-23 | 2009-02-17 | Millennium Pharmaceuticals, Inc. | Aryl sulfonamides useful as inhibitors of chemokine receptor activity |
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| US7199259B2 (en) * | 2003-06-20 | 2007-04-03 | Metabolex, Inc. | Resolution of α-(phenoxy)phenylacetic acid derivatives |
| WO2005046683A1 (en) * | 2003-10-07 | 2005-05-26 | Renovis, Inc. | Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same |
| EP1725544B1 (en) * | 2004-03-09 | 2009-05-27 | Boehringer Ingelheim Pharmaceuticals Inc. | 3-[4-heterocyclyl-1,2,3-triazol-1-yl]-n-aryl-benzamides as inhibitors of the cytokines production for the treatment of chronic inflammatory diseases |
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| WO2006102645A1 (en) * | 2005-03-24 | 2006-09-28 | Janssen Pharmaceutica, N.V. | Biaryl derived amide modulators of vanilloid vr1 receptor |
| KR101363278B1 (ko) * | 2005-06-27 | 2014-02-21 | 엑셀리시스 페이턴트 컴퍼니 엘엘씨 | 이미다졸계 ｌｘｒ 변조제 |
| JPWO2007010731A1 (ja) * | 2005-07-15 | 2009-01-29 | Jsr株式会社 | 含窒素芳香族化合物およびその製造方法、重合体およびプロトン伝導膜 |
| WO2007016979A2 (en) * | 2005-07-29 | 2007-02-15 | 4Sc Ag | NOVEL HETEROCYCLIC NF-κB INHIBITORS |
| US7714131B2 (en) * | 2005-09-23 | 2010-05-11 | Metabolex, Inc. | Process for the stereoselective preparation of (−)-halofenate and derivatives thereof |
| US8247556B2 (en) | 2005-10-21 | 2012-08-21 | Amgen Inc. | Method for preparing 6-substituted-7-aza-indoles |
| JP2009518442A (ja) * | 2005-12-05 | 2009-05-07 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 可溶性エポキシド加水分解酵素インヒビターとして有益な置換ピラゾール化合物 |
| CA2635888A1 (en) * | 2006-01-04 | 2007-07-19 | Locus Pharmaceuticals, Inc. | Inhibitors of protein kinases |
| US8084473B2 (en) * | 2007-04-24 | 2011-12-27 | Solvay Pharmaceuticals B.V. | Heterocyclic compounds with affinity to muscarinic receptors |
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1999
- 1999-06-03 US US09/324,933 patent/US6506747B1/en not_active Expired - Lifetime
- 1999-06-03 CA CA002332957A patent/CA2332957A1/en not_active Abandoned
- 1999-06-03 AU AU42299/99A patent/AU4229999A/en not_active Abandoned
- 1999-06-03 JP JP2000552097A patent/JP2002516909A/ja active Pending
- 1999-06-03 WO PCT/US1999/012295 patent/WO1999062885A1/en not_active Ceased
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