AU2004275488A1 - Pyridine derivatives and use thereof as urotensin II antagonists - Google Patents
Pyridine derivatives and use thereof as urotensin II antagonists Download PDFInfo
- Publication number
- AU2004275488A1 AU2004275488A1 AU2004275488A AU2004275488A AU2004275488A1 AU 2004275488 A1 AU2004275488 A1 AU 2004275488A1 AU 2004275488 A AU2004275488 A AU 2004275488A AU 2004275488 A AU2004275488 A AU 2004275488A AU 2004275488 A1 AU2004275488 A1 AU 2004275488A1
- Authority
- AU
- Australia
- Prior art keywords
- ethyl
- pyridin
- piperidin
- ureido
- dimethyl
- 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.)
- Abandoned
Links
- 239000005557 antagonist Substances 0.000 title claims description 8
- 108010018369 Urotensin II Proteins 0.000 title description 15
- 102000050488 Urotensin II Human genes 0.000 title description 15
- 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 title description 15
- 150000003222 pyridines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 194
- -1 1-{2-[3-(2-Methyl-6-propyl-pyridin-4-yl)-ureido]-ethyl}-4-phenyl-piperidine-4 carboxylic acid benzyl-methyl-amide 1-[2-(4-Benzyl-piperidin-1 -yl)-ethyl]-3-(2-methyl-6-propyl-pyridin-4-yl)-urea Chemical compound 0.000 claims description 125
- 239000000203 mixture Substances 0.000 claims description 94
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 80
- 125000003118 aryl group Chemical group 0.000 claims description 64
- 239000001257 hydrogen Substances 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 51
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- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 46
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 36
- 125000002837 carbocyclic group Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 125000006413 ring segment Chemical group 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 210000004027 cell Anatomy 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 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 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 206010012601 diabetes mellitus Diseases 0.000 claims description 8
- XNIOWJUQPMKCIJ-UHFFFAOYSA-N 2-(benzylamino)ethanol Chemical compound OCCNCC1=CC=CC=C1 XNIOWJUQPMKCIJ-UHFFFAOYSA-N 0.000 claims description 6
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- PSHRXNWYHPYFQX-OXFOZPMTSA-N urotensin i Chemical compound CSCC[C@H](N)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(N)=O)CC1=CC=C(O)C=C1 PSHRXNWYHPYFQX-OXFOZPMTSA-N 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
- 230000002792 vascular Effects 0.000 claims description 5
- UMQSLMSNBMTPJY-UHFFFAOYSA-N 2,5-dichlorothiophene-3-sulfonic acid Chemical compound OS(=O)(=O)C=1C=C(Cl)SC=1Cl UMQSLMSNBMTPJY-UHFFFAOYSA-N 0.000 claims description 4
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- AFFPZJFLSDVZBV-UHFFFAOYSA-N 2-(trifluoromethyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1C(F)(F)F AFFPZJFLSDVZBV-UHFFFAOYSA-N 0.000 claims description 3
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- 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 description 3
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- 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
- HPBWWHVRBKXSEO-UHFFFAOYSA-N 1-[2-[4-[ethyl-(4-methoxyphenyl)sulfonylamino]piperidin-1-yl]ethyl]-3-(2-methyl-6-propylpyridin-4-yl)urea Chemical compound CC1=NC(CCC)=CC(NC(=O)NCCN2CCC(CC2)N(CC)S(=O)(=O)C=2C=CC(OC)=CC=2)=C1 HPBWWHVRBKXSEO-UHFFFAOYSA-N 0.000 claims 1
- GWJVQLLJRMXZOI-UHFFFAOYSA-N 1-[2-[4-[ethyl-(4-methoxyphenyl)sulfonylamino]piperidin-1-yl]ethyl]-3-[2-methyl-6-(2-phenylethyl)pyridin-4-yl]urea Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)N(CC)C(CC1)CCN1CCNC(=O)NC(C=1)=CC(C)=NC=1CCC1=CC=CC=C1 GWJVQLLJRMXZOI-UHFFFAOYSA-N 0.000 claims 1
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EPPCT/EP03/10746 | 2003-09-26 | ||
| EP0310746 | 2003-09-26 | ||
| PCT/EP2004/010559 WO2005030209A1 (en) | 2003-09-26 | 2004-09-21 | Pyridine derivatives and use thereof as urotensin ii antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2004275488A1 true AU2004275488A1 (en) | 2005-04-07 |
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| AU2004275488A Abandoned AU2004275488A1 (en) | 2003-09-26 | 2004-09-21 | Pyridine derivatives and use thereof as urotensin II antagonists |
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| CN (1) | CN1856305B (enExample) |
| AR (1) | AR045949A1 (enExample) |
| AT (1) | ATE427748T1 (enExample) |
| AU (1) | AU2004275488A1 (enExample) |
| BR (1) | BRPI0414777A (enExample) |
| CA (1) | CA2540196C (enExample) |
| DE (1) | DE602004020486D1 (enExample) |
| IL (1) | IL174497A0 (enExample) |
| MX (1) | MXPA06003264A (enExample) |
| NO (1) | NO20061395L (enExample) |
| RU (1) | RU2006113948A (enExample) |
| TW (1) | TW200526630A (enExample) |
| WO (1) | WO2005030209A1 (enExample) |
| ZA (1) | ZA200602442B (enExample) |
Families Citing this family (17)
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| EP1608319A4 (en) | 2003-04-03 | 2007-02-28 | Univ California | IMPROVED HEMMER FOR SOLUBLE EPOXY HYDROLASE |
| DE10358539A1 (de) * | 2003-12-15 | 2005-07-07 | Merck Patent Gmbh | Carbonsäureamidderivate |
| CA2559665A1 (en) | 2004-03-16 | 2005-09-29 | The Regents Of The University Of California | Reducing nephropathy with inhibitors of soluble epoxide hydrolase and epoxyeicosanoids |
| CN101039930B (zh) * | 2004-10-12 | 2010-08-11 | 埃科特莱茵药品有限公司 | 作为结晶硫酸盐的1-[2-(4-甲苯基-4-羟基-哌啶-1-基)-乙基]-3-(2-甲基-喹啉-4-基)-脲 |
| TW200630337A (en) * | 2004-10-14 | 2006-09-01 | Euro Celtique Sa | Piperidinyl compounds and the use thereof |
| ZA200703613B (en) | 2004-10-20 | 2009-05-27 | Univ California | Improved inhibitors for the soluble epoxide hydrolase |
| SE0403084D0 (sv) * | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Chemical process |
| WO2006135694A2 (en) * | 2005-06-10 | 2006-12-21 | Acadia Pharmaceuticals Inc. | Uii-modulating compounds and their use |
| TW200808723A (en) | 2006-03-13 | 2008-02-16 | Univ California | Conformationally restricted urea inhibitors of soluble epoxide hydrolase |
| WO2007110449A1 (en) | 2006-03-29 | 2007-10-04 | Euro-Celtique S.A. | Benzenesulfonamide compounds and their use |
| US8791264B2 (en) * | 2006-04-13 | 2014-07-29 | Purdue Pharma L.P. | Benzenesulfonamide compounds and their use as blockers of calcium channels |
| TW200812963A (en) | 2006-04-13 | 2008-03-16 | Euro Celtique Sa | Benzenesulfonamide compounds and the use thereof |
| ATE545647T1 (de) * | 2006-12-22 | 2012-03-15 | Actelion Pharmaceuticals Ltd | 5,6,7,8-tetrahydro-imidazoä1,5-aüpyrazinderivat |
| WO2008124118A1 (en) | 2007-04-09 | 2008-10-16 | Purdue Pharma L.P. | Benzenesulfonyl compounds and the use therof |
| US8765736B2 (en) * | 2007-09-28 | 2014-07-01 | Purdue Pharma L.P. | Benzenesulfonamide compounds and the use thereof |
| CN101925383A (zh) | 2007-12-11 | 2010-12-22 | 赛特帕斯凡德株式会社 | 甲酰胺化合物及其作为趋化因子受体激动剂的应用 |
| US9296693B2 (en) | 2010-01-29 | 2016-03-29 | The Regents Of The University Of California | Acyl piperidine inhibitors of soluble epoxide hydrolase |
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|---|---|---|---|---|
| FI97540C (fi) | 1989-11-06 | 1997-01-10 | Sanofi Sa | Menetelmä terapeuttisesti käyttökelpoisten, aromaattisesti substituoitujen piperidiini- ja piperatsiinijohdannaisten valmistamiseksi |
| US6159700A (en) | 1997-01-27 | 2000-12-12 | Smithkline Beecham Corporation | Method of finding agonist and antagonist to human and rat GPR14 |
| AUPP003197A0 (en) | 1997-09-03 | 1997-11-20 | Fujisawa Pharmaceutical Co., Ltd. | New heterocyclic compounds |
| US6444686B1 (en) * | 1998-12-18 | 2002-09-03 | Brsitol-Myers Squibb Pharma Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| US6331541B1 (en) * | 1998-12-18 | 2001-12-18 | Soo S. Ko | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| EP1200395B1 (en) | 1999-07-28 | 2006-03-29 | Kirin Beer Kabushiki Kaisha | Urea derivatives as inhibitors of ccr-3 receptor |
| ES2225297T3 (es) | 1999-12-21 | 2005-03-16 | Smithkline Beecham Corporation | Antagonistas del receptor de urotensina ii. |
| AU2441801A (en) | 1999-12-21 | 2001-07-03 | Smithkline Beecham Corporation | Urotensin-ii receptor antagonists |
| ATE249831T1 (de) | 1999-12-21 | 2003-10-15 | Smithkline Beecham Corp | Carboxamidderivate von pyrrolidine und piperidine als urotensin-ii rezeptorantagonisten |
| CA2402096A1 (en) | 2000-03-07 | 2001-09-13 | Takeda Chemical Industries, Ltd. | Vasoactive agents |
| JP2004517803A (ja) * | 2000-06-21 | 2004-06-17 | ブリストル−マイヤーズ・スクイブ・ファーマ・カンパニー | ケモカイン受容体活性調節剤としてのｎ−ウレイドアルキル−ピペリジン |
| AU2001266346A1 (en) | 2000-06-28 | 2002-01-08 | Takeda Chemical Industries Ltd. | Biphenyl compound |
| WO2002002530A1 (en) | 2000-07-04 | 2002-01-10 | Takeda Chemical Industries, Ltd. | Gpr14 antagonist |
| WO2002047687A1 (en) | 2000-12-11 | 2002-06-20 | Smithkline Beecham Corporation | Urotensin-ii receptor antagonists |
| EP1351687A4 (en) | 2000-12-11 | 2004-01-21 | Smithkline Beecham Corp | UROTENSIN II RECEPTOR ANTAGONISTS |
| WO2002058702A1 (en) | 2001-01-26 | 2002-08-01 | Smithkline Beecham Corporation | Urotensin-ii receptor antagonists |
| US6815451B2 (en) * | 2001-03-27 | 2004-11-09 | Actelion Pharmaceuticals Ltd. | 1,2,3,4-Tetrahydroisoquinolines derivatives as urotensin II receptor antagonists |
| JP2004524355A (ja) | 2001-03-29 | 2004-08-12 | スミスクライン・ビーチャム・コーポレイション | ピロリジンスルホンアミド |
| US20040152692A1 (en) | 2001-03-29 | 2004-08-05 | Dashyant Dhanak | Pyrrolidine sulfonamides |
| JP2004525156A (ja) | 2001-03-29 | 2004-08-19 | スミスクライン・ビーチャム・コーポレイション | ピロリジンスルホンアミド |
| AU2002309524A1 (en) | 2001-03-29 | 2002-10-15 | Smithkline Beecham Corporation | Pyrrolidine 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 |
| JP2005508852A (ja) | 2001-05-07 | 2005-04-07 | 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 |
| WO2002089793A1 (en) | 2001-05-07 | 2002-11-14 | Smithkline Beecham Corporation | Sulfonamides |
| 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 |
| 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 |
| 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 |
| CA2473892C (en) | 2001-12-04 | 2010-09-21 | Actelion Pharmaceuticals Ltd | Novel quinoline derivatives |
| KR20050043967A (ko) * | 2002-09-17 | 2005-05-11 | 액테리온 파마슈티칼 리미티드 | 1-피리딘-4-일-요소 유도체 |
| WO2004043368A2 (en) | 2002-11-06 | 2004-05-27 | Smithkline Beecham Corporation | Sulfonamides |
| WO2004043917A1 (en) | 2002-11-06 | 2004-05-27 | Smithkline Beecham Corporation | Sulfonamides |
| WO2004043366A2 (en) | 2002-11-06 | 2004-05-27 | Smithkline Beecham Corporation | Sulfonamides |
| AU2003291262A1 (en) | 2002-11-06 | 2004-06-03 | Smithkline Beecham Corporation | Sulfonamides |
| AR041885A1 (es) | 2002-11-06 | 2005-06-01 | Smithkline Beecham Corp | Compuesto de sulfonamida, composicion farmaceutica que lo comprende y su uso para preparar dicha composicion |
| AU2004212985B2 (en) | 2003-02-20 | 2010-10-14 | Encysive Pharmaceuticals Inc. | Phenylenediamine urotensin-II receptor antagonists and CCR-9 antagonists |
| EP1631565A1 (en) * | 2003-05-07 | 2006-03-08 | Actelion Pharmaceuticals Ltd. | Piperazine-alkyl-ureido derivatives |
-
2004
- 2004-09-21 CN CN2004800277254A patent/CN1856305B/zh not_active Expired - Fee Related
- 2004-09-21 KR KR1020067005848A patent/KR20070014108A/ko not_active Withdrawn
- 2004-09-21 WO PCT/EP2004/010559 patent/WO2005030209A1/en not_active Ceased
- 2004-09-21 RU RU2006113948/04A patent/RU2006113948A/ru unknown
- 2004-09-21 MX MXPA06003264A patent/MXPA06003264A/es unknown
- 2004-09-21 US US10/573,516 patent/US7750161B2/en not_active Expired - Fee Related
- 2004-09-21 AU AU2004275488A patent/AU2004275488A1/en not_active Abandoned
- 2004-09-21 DE DE602004020486T patent/DE602004020486D1/de not_active Expired - Lifetime
- 2004-09-21 EP EP04765436A patent/EP1670470B1/en not_active Expired - Lifetime
- 2004-09-21 BR BRPI0414777-4A patent/BRPI0414777A/pt not_active Application Discontinuation
- 2004-09-21 AT AT04765436T patent/ATE427748T1/de not_active IP Right Cessation
- 2004-09-21 JP JP2006527332A patent/JP4851328B2/ja not_active Expired - Fee Related
- 2004-09-21 CA CA2540196A patent/CA2540196C/en not_active Expired - Fee Related
- 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 |
|---|---|
| KR20070014108A (ko) | 2007-01-31 |
| CA2540196A1 (en) | 2005-04-07 |
| RU2006113948A (ru) | 2007-11-10 |
| EP1670470B1 (en) | 2009-04-08 |
| ZA200602442B (en) | 2007-09-26 |
| IL174497A0 (en) | 2006-08-01 |
| WO2005030209A1 (en) | 2005-04-07 |
| WO2005030209A8 (en) | 2006-05-11 |
| MXPA06003264A (es) | 2006-06-08 |
| CA2540196C (en) | 2012-03-20 |
| BRPI0414777A (pt) | 2006-11-21 |
| US20070043081A1 (en) | 2007-02-22 |
| US7750161B2 (en) | 2010-07-06 |
| JP4851328B2 (ja) | 2012-01-11 |
| CN1856305B (zh) | 2010-04-28 |
| AR045949A1 (es) | 2005-11-16 |
| NO20061395L (no) | 2006-06-22 |
| DE602004020486D1 (de) | 2009-05-20 |
| CN1856305A (zh) | 2006-11-01 |
| TW200526630A (en) | 2005-08-16 |
| EP1670470A1 (en) | 2006-06-21 |
| JP2007506692A (ja) | 2007-03-22 |
| ATE427748T1 (de) | 2009-04-15 |
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| Date | Code | Title | Description |
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| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |