RU2006113948A - Производные пиридина и их применение в качестве антагонистов уротензина ii - Google Patents
Производные пиридина и их применение в качестве антагонистов уротензина ii Download PDFInfo
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- RU2006113948A RU2006113948A RU2006113948/04A RU2006113948A RU2006113948A RU 2006113948 A RU2006113948 A RU 2006113948A RU 2006113948/04 A RU2006113948/04 A RU 2006113948/04A RU 2006113948 A RU2006113948 A RU 2006113948A RU 2006113948 A RU2006113948 A RU 2006113948A
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- Prior art keywords
- ethyl
- ureido
- piperidin
- dimethylpyridin
- aryl
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- 239000005557 antagonist Substances 0.000 title claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title 1
- -1 pyridin-4-yl radical Chemical class 0.000 claims 108
- 150000001875 compounds Chemical class 0.000 claims 35
- 239000001257 hydrogen Substances 0.000 claims 24
- 229910052739 hydrogen Inorganic materials 0.000 claims 24
- 125000003118 aryl group Chemical group 0.000 claims 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 19
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 18
- 125000002837 carbocyclic group Chemical group 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 206010012601 diabetes mellitus Diseases 0.000 claims 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- DEVUYWTZRXOMSI-UHFFFAOYSA-N (sulfamoylamino)benzene Chemical compound NS(=O)(=O)NC1=CC=CC=C1 DEVUYWTZRXOMSI-UHFFFAOYSA-N 0.000 claims 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 4
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
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- 208000020832 chronic kidney disease Diseases 0.000 claims 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
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- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010010904 Convulsion Diseases 0.000 claims 2
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims 2
- 108010036949 Cyclosporine Proteins 0.000 claims 2
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- 239000002671 adjuvant Substances 0.000 claims 2
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- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 2
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- 229960001265 ciclosporin Drugs 0.000 claims 2
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- 229930182912 cyclosporin Natural products 0.000 claims 2
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 2
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- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 claims 1
- JWWGZUNNEIUCNE-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[2-(3,3-diphenylpyrrolidin-1-yl)ethyl]urea Chemical compound CC1=NC(C)=CC(NC(=O)NCCN2CC(CC2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 JWWGZUNNEIUCNE-UHFFFAOYSA-N 0.000 claims 1
- FFIHDYBQWKZAKX-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)-3-[2-[4-[methyl-[4-(trifluoromethyl)phenyl]sulfonylamino]piperidin-1-yl]ethyl]urea Chemical compound C=1C=C(C(F)(F)F)C=CC=1S(=O)(=O)N(C)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 FFIHDYBQWKZAKX-UHFFFAOYSA-N 0.000 claims 1
- WCPFQQHADRJANG-UHFFFAOYSA-N 1-(4-methoxyphenyl)cyclopropane-1-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1(C(O)=O)CC1 WCPFQQHADRJANG-UHFFFAOYSA-N 0.000 claims 1
- CUTGZUCYQMNVJF-UHFFFAOYSA-N 1-[2-(4-benzyl-4-hydroxypiperidin-1-yl)ethyl]-3-(2,6-diethylpyridin-4-yl)urea Chemical compound CCC1=NC(CC)=CC(NC(=O)NCCN2CCC(O)(CC=3C=CC=CC=3)CC2)=C1 CUTGZUCYQMNVJF-UHFFFAOYSA-N 0.000 claims 1
- YTDCFWNNOYWQHK-UHFFFAOYSA-N 1-[2-(4-benzyl-4-hydroxypiperidin-1-yl)ethyl]-3-(2,6-dimethylpyridin-4-yl)urea Chemical compound CC1=NC(C)=CC(NC(=O)NCCN2CCC(O)(CC=3C=CC=CC=3)CC2)=C1 YTDCFWNNOYWQHK-UHFFFAOYSA-N 0.000 claims 1
- QADSWFUWTFRSTI-UHFFFAOYSA-N 1-[2-(4-benzyl-4-hydroxypiperidin-1-yl)ethyl]-3-(2-ethyl-6-methylpyridin-4-yl)urea Chemical compound CC1=NC(CC)=CC(NC(=O)NCCN2CCC(O)(CC=3C=CC=CC=3)CC2)=C1 QADSWFUWTFRSTI-UHFFFAOYSA-N 0.000 claims 1
- CGVXZQKFKMHDPG-UHFFFAOYSA-N 1-[2-(4-benzyl-4-hydroxypiperidin-1-yl)ethyl]-3-[2-(2-phenylethyl)pyridin-4-yl]urea Chemical compound C1CN(CCNC(=O)NC=2C=C(CCC=3C=CC=CC=3)N=CC=2)CCC1(O)CC1=CC=CC=C1 CGVXZQKFKMHDPG-UHFFFAOYSA-N 0.000 claims 1
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- QIQVSDKBVFEASF-UHFFFAOYSA-N 1-[2-[4-(cyclopropylamino)piperidin-1-yl]ethyl]-3-(2,6-dimethylpyridin-4-yl)urea Chemical compound CC1=NC(C)=CC(NC(=O)NCCN2CCC(CC2)NC2CC2)=C1 QIQVSDKBVFEASF-UHFFFAOYSA-N 0.000 claims 1
- GBDCYEMRIVDQFP-UHFFFAOYSA-N 1-[2-[4-[(2,6-difluorophenyl)sulfonyl-ethylamino]piperidin-1-yl]ethyl]-3-(2,6-dimethylpyridin-4-yl)urea Chemical compound FC=1C=CC=C(F)C=1S(=O)(=O)N(CC)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 GBDCYEMRIVDQFP-UHFFFAOYSA-N 0.000 claims 1
- GUNHYCLKBCIWEX-UHFFFAOYSA-N 1-[2-[4-[(3,4-difluorophenyl)sulfonyl-ethylamino]piperidin-1-yl]ethyl]-3-(2,6-dimethylpyridin-4-yl)urea Chemical compound C=1C=C(F)C(F)=CC=1S(=O)(=O)N(CC)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 GUNHYCLKBCIWEX-UHFFFAOYSA-N 0.000 claims 1
- KOUVYYQUIQJPCK-UHFFFAOYSA-N 1-[2-[4-[(3,4-dimethoxyphenyl)sulfonyl-ethylamino]piperidin-1-yl]ethyl]-3-(2,6-dimethylpyridin-4-yl)urea Chemical compound C=1C=C(OC)C(OC)=CC=1S(=O)(=O)N(CC)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 KOUVYYQUIQJPCK-UHFFFAOYSA-N 0.000 claims 1
- ARHYSDQOKXDTRM-UHFFFAOYSA-N 1-[2-[4-[ethyl-(4-fluorophenyl)sulfonylamino]piperidin-1-yl]ethyl]-3-(2-ethyl-6-methylpyridin-4-yl)urea Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)N(CC)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(CC)=C1 ARHYSDQOKXDTRM-UHFFFAOYSA-N 0.000 claims 1
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- PVAFEQHVEAVCJP-UHFFFAOYSA-N n-[1-[2-[(2,6-dimethylpyridin-4-yl)carbamoylamino]ethyl]piperidin-4-yl]-n-ethyl-4-fluorobenzamide Chemical compound C=1C=C(F)C=CC=1C(=O)N(CC)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 PVAFEQHVEAVCJP-UHFFFAOYSA-N 0.000 claims 1
- RZPNUNDXIUUBNP-UHFFFAOYSA-N n-[1-[2-[(2,6-dimethylpyridin-4-yl)carbamoylamino]ethyl]piperidin-4-yl]-n-methyl-2-phenylacetamide Chemical compound C=1C=CC=CC=1CC(=O)N(C)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(C)=C1 RZPNUNDXIUUBNP-UHFFFAOYSA-N 0.000 claims 1
- SDBCDGMASFQENW-UHFFFAOYSA-N n-[4-[[1-[2-[(2,6-dimethylpyridin-4-yl)carbamoylamino]ethyl]piperidin-4-yl]methylsulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NCC1CCN(CCNC(=O)NC=2C=C(C)N=C(C)C=2)CC1 SDBCDGMASFQENW-UHFFFAOYSA-N 0.000 claims 1
- LPCFSSAXQPCDLB-UHFFFAOYSA-N n-ethyl-n-[1-[2-[(2-ethyl-6-methylpyridin-4-yl)carbamoylamino]ethyl]piperidin-4-yl]-2-phenylacetamide Chemical compound C=1C=CC=CC=1CC(=O)N(CC)C(CC1)CCN1CCNC(=O)NC1=CC(C)=NC(CC)=C1 LPCFSSAXQPCDLB-UHFFFAOYSA-N 0.000 claims 1
- 239000003614 peroxisome proliferator Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
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- 201000004240 prostatic hypertrophy Diseases 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- HFNHAPQMXICKCF-USJMABIRSA-N urotensin-ii Chemical compound N([C@@H](CC(O)=O)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@@H](C(C)C)C(O)=O)C(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H](N)CCC(O)=O)[C@@H](C)O HFNHAPQMXICKCF-USJMABIRSA-N 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- 239000003038 vasopressin antagonist Substances 0.000 claims 1
- 0 CC(C)(CC1(C)C)CN(CCNC(N*)=O)CCC1(*)I Chemical compound CC(C)(CC1(C)C)CN(CCNC(N*)=O)CCC1(*)I 0.000 description 4
Classifications
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| DE10358539A1 (de) * | 2003-12-15 | 2005-07-07 | Merck Patent Gmbh | Carbonsäureamidderivate |
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| EP1379519A1 (en) | 2001-03-29 | 2004-01-14 | SmithKline Beecham Corporation | Pyrrolidine sulfonamides |
| WO2002089793A1 (en) | 2001-05-07 | 2002-11-14 | Smithkline Beecham Corporation | Sulfonamides |
| JP2004529168A (ja) | 2001-05-07 | 2004-09-24 | スミスクライン・ビーチャム・コーポレイション | スルホンアミド |
| JP2004529170A (ja) | 2001-05-07 | 2004-09-24 | スミスクライン・ビーチャム・コーポレイション | スルホンアミド |
| AR033879A1 (es) | 2001-05-07 | 2004-01-07 | Smithkline Beecham Corp | Compuesto sulfonamida, composicion farmaceutica que lo comprende, su uso para preparar dicha composicion y procedimiento para la obtencion de dicho compuesto |
| JP2004535390A (ja) | 2001-05-07 | 2004-11-25 | スミスクライン・ビーチャム・コーポレイション | スルホンアミド |
| EP1385495A4 (en) | 2001-05-07 | 2005-12-21 | Smithkline Beecham Corp | SULPHONAMIDES |
| WO2003048154A1 (en) | 2001-12-04 | 2003-06-12 | Actelion Pharmaceuticals Ltd | 4-(piperidyl- and pyrrolidyl-alkyl-ureido) -quinolines as urotensin ii receptor antagonists |
| JP2006505533A (ja) * | 2002-09-17 | 2006-02-16 | アクテリオン ファマシューティカルズ リミテッド | １−ピリジン−４−イル−尿素誘導体 |
| WO2004043366A2 (en) | 2002-11-06 | 2004-05-27 | Smithkline Beecham Corporation | Sulfonamides |
| TW200418831A (en) | 2002-11-06 | 2004-10-01 | Smithkline Beecham Corp | Sulfonamides |
| AU2003295408A1 (en) | 2002-11-06 | 2004-06-03 | Smithkline Beecham Corporation | Sulfonamides |
| AU2003291262A1 (en) | 2002-11-06 | 2004-06-03 | Smithkline Beecham Corporation | Sulfonamides |
| AU2003291255A1 (en) | 2002-11-06 | 2004-06-03 | Smithkline Beecham Corporation | Sulfonamides |
| US7319111B2 (en) | 2003-02-20 | 2008-01-15 | Encysive Pharmaceuticals, Inc. | Phenylenediamine Urotensin-II receptor antagonists and CCR-9 antagonists |
| WO2004099179A1 (en) | 2003-05-07 | 2004-11-18 | Actelion Pharmaceuticals Ltd | Piperazine-alkyl-ureido derivatives |
-
2004
- 2004-09-21 US US10/573,516 patent/US7750161B2/en not_active Expired - Fee Related
- 2004-09-21 AT AT04765436T patent/ATE427748T1/de not_active IP Right Cessation
- 2004-09-21 WO PCT/EP2004/010559 patent/WO2005030209A1/en not_active Ceased
- 2004-09-21 KR KR1020067005848A patent/KR20070014108A/ko not_active Withdrawn
- 2004-09-21 CN CN2004800277254A patent/CN1856305B/zh not_active Expired - Fee Related
- 2004-09-21 MX MXPA06003264A patent/MXPA06003264A/es unknown
- 2004-09-21 AU AU2004275488A patent/AU2004275488A1/en not_active Abandoned
- 2004-09-21 RU RU2006113948/04A patent/RU2006113948A/ru unknown
- 2004-09-21 CA CA2540196A patent/CA2540196C/en not_active Expired - Fee Related
- 2004-09-21 EP EP04765436A patent/EP1670470B1/en not_active Expired - Lifetime
- 2004-09-21 JP JP2006527332A patent/JP4851328B2/ja not_active Expired - Fee Related
- 2004-09-21 DE DE602004020486T patent/DE602004020486D1/de not_active Expired - Lifetime
- 2004-09-21 BR BRPI0414777-4A patent/BRPI0414777A/pt not_active Application Discontinuation
- 2004-09-24 TW TW093129149A patent/TW200526630A/zh unknown
- 2004-09-24 AR ARP040103475A patent/AR045949A1/es unknown
-
2006
- 2006-03-22 IL IL174497A patent/IL174497A0/en unknown
- 2006-03-24 ZA ZA200602442A patent/ZA200602442B/en unknown
- 2006-03-27 NO NO20061395A patent/NO20061395L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| TW200526630A (en) | 2005-08-16 |
| CN1856305B (zh) | 2010-04-28 |
| WO2005030209A8 (en) | 2006-05-11 |
| CN1856305A (zh) | 2006-11-01 |
| NO20061395L (no) | 2006-06-22 |
| IL174497A0 (en) | 2006-08-01 |
| KR20070014108A (ko) | 2007-01-31 |
| ATE427748T1 (de) | 2009-04-15 |
| MXPA06003264A (es) | 2006-06-08 |
| JP4851328B2 (ja) | 2012-01-11 |
| WO2005030209A1 (en) | 2005-04-07 |
| EP1670470A1 (en) | 2006-06-21 |
| EP1670470B1 (en) | 2009-04-08 |
| AU2004275488A1 (en) | 2005-04-07 |
| BRPI0414777A (pt) | 2006-11-21 |
| US7750161B2 (en) | 2010-07-06 |
| DE602004020486D1 (de) | 2009-05-20 |
| US20070043081A1 (en) | 2007-02-22 |
| ZA200602442B (en) | 2007-09-26 |
| AR045949A1 (es) | 2005-11-16 |
| JP2007506692A (ja) | 2007-03-22 |
| CA2540196C (en) | 2012-03-20 |
| CA2540196A1 (en) | 2005-04-07 |
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