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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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004275488A Abandoned AU2004275488A1 (en) | 2003-09-26 | 2004-09-21 | Pyridine derivatives and use thereof as urotensin II antagonists |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7750161B2 (OSRAM) |
| EP (1) | EP1670470B1 (OSRAM) |
| JP (1) | JP4851328B2 (OSRAM) |
| KR (1) | KR20070014108A (OSRAM) |
| CN (1) | CN1856305B (OSRAM) |
| AR (1) | AR045949A1 (OSRAM) |
| AT (1) | ATE427748T1 (OSRAM) |
| AU (1) | AU2004275488A1 (OSRAM) |
| BR (1) | BRPI0414777A (OSRAM) |
| CA (1) | CA2540196C (OSRAM) |
| DE (1) | DE602004020486D1 (OSRAM) |
| IL (1) | IL174497A0 (OSRAM) |
| MX (1) | MXPA06003264A (OSRAM) |
| NO (1) | NO20061395L (OSRAM) |
| RU (1) | RU2006113948A (OSRAM) |
| TW (1) | TW200526630A (OSRAM) |
| WO (1) | WO2005030209A1 (OSRAM) |
| ZA (1) | ZA200602442B (OSRAM) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004089296A2 (en) | 2003-04-03 | 2004-10-21 | The Regents Of The University Of California | Improved inhibitors for the soluble epoxide 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 |
| KR101271372B1 (ko) * | 2004-10-12 | 2013-06-07 | 액테리온 파마슈티칼 리미티드 | 결정질 술페이트 염으로서의 1-〔2-(4-벤질-4-하이드록시-피페리딘-1-일)-에틸〕-3-(2-메틸-퀴놀린-4-일)-유레아 |
| TW200630337A (en) * | 2004-10-14 | 2006-09-01 | Euro Celtique Sa | Piperidinyl compounds and the use thereof |
| NZ554555A (en) | 2004-10-20 | 2011-09-30 | Univ California | Cyclohexyl-urea derivatives as 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 |
| AR059826A1 (es) | 2006-03-13 | 2008-04-30 | Univ California | Inhibidores de urea conformacionalmente restringidos de epoxido hidrolasa soluble |
| US8247442B2 (en) | 2006-03-29 | 2012-08-21 | Purdue Pharma L.P. | 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 |
| WO2007118854A1 (en) * | 2006-04-13 | 2007-10-25 | Euro-Celtique S.A. | Benzenesulfonamide compounds and the use thereof |
| EP2125823B1 (en) * | 2006-12-22 | 2012-02-15 | Actelion Pharmaceuticals Ltd. | 5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine derivatives |
| US8399486B2 (en) | 2007-04-09 | 2013-03-19 | Purdue Pharma L.P. | Benzenesulfonyl compounds and the use thereof |
| WO2009040659A2 (en) * | 2007-09-28 | 2009-04-02 | Purdue Pharma L.P. | Benzenesulfonamide compounds and the use thereof |
| JP2011506466A (ja) | 2007-12-11 | 2011-03-03 | 株式会社サイトパスファインダー | カルボキサミド化合物ならびにケモカイン受容体アゴニストとしてのそれらの使用 |
| WO2012054093A2 (en) | 2010-01-29 | 2012-04-26 | The Regents Of The University Of California | Acyl piperidine inhibitors of soluble epoxide hydrolase |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE903957A1 (en) | 1989-11-06 | 1991-05-08 | Sanofi Sa | Aromatic amine compounds, their method of preparation and¹pharmaceutical compositions in which they are present |
| 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 |
| US6331541B1 (en) * | 1998-12-18 | 2001-12-18 | Soo S. Ko | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| CA2347770A1 (en) * | 1998-12-18 | 2000-06-22 | Bristol-Myers Squibb Pharma Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| DE60027011T2 (de) | 1999-07-28 | 2006-12-07 | Kirin Beer K.K. | Harnstoffderivate als CCR-3 Rezeptor-Inhibitoren |
| US6544992B1 (en) | 1999-12-21 | 2003-04-08 | Smithkline Beecham Corporation | Urotensin-II receptor antagonists |
| ATE279923T1 (de) | 1999-12-21 | 2004-11-15 | Smithkline Beecham Corp | Urotensin-ii rezeptorantagonisten |
| EP1248607A4 (en) | 1999-12-21 | 2004-10-06 | Smithkline Beecham Corp | UROTENSIN II RECEPTOR ANTAGONISTS |
| CA2402096A1 (en) | 2000-03-07 | 2001-09-13 | Takeda Chemical Industries, Ltd. | Vasoactive agents |
| CA2413274A1 (en) * | 2000-06-21 | 2001-12-27 | George V. Delucca | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| US7091247B2 (en) | 2000-06-28 | 2006-08-15 | Takeda Pharmaceutical Company Limited | Biphenyl compound |
| CA2414976A1 (en) | 2000-07-04 | 2002-01-10 | Takeda Chemical Industries, Ltd. | Gpr14 antagonistic agent |
| EP1351687A4 (en) | 2000-12-11 | 2004-01-21 | Smithkline Beecham Corp | UROTENSIN II RECEPTOR ANTAGONISTS |
| EP1351688A4 (en) | 2000-12-11 | 2006-01-04 | Smithkline Beecham Corp | UROTENSIN-II RECEPTOR ANTAGONISTS |
| US6818655B2 (en) | 2001-01-26 | 2004-11-16 | Smithkline Beecham Corporation | Urotensin-II receptor antagonists |
| WO2002076979A1 (en) | 2001-03-27 | 2002-10-03 | Actelion Pharmaceuticals Ltd | 1,2,3,4-tetrahydroisoquinolines derivatives as urotensin ii receptor antagonists |
| AU2002309524A1 (en) | 2001-03-29 | 2002-10-15 | Smithkline Beecham Corporation | Pyrrolidine sulfonamides |
| EP1379503A1 (en) | 2001-03-29 | 2004-01-14 | SmithKline Beecham Corporation | Pyrrolidine sulfonamides |
| EP1379519A1 (en) | 2001-03-29 | 2004-01-14 | SmithKline Beecham Corporation | Pyrrolidine sulfonamides |
| WO2002078707A1 (en) | 2001-03-29 | 2002-10-10 | 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 |
| EP1399137A4 (en) | 2001-05-07 | 2005-12-14 | Smithkline Beecham Corp | SULPHONAMIDES |
| 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 |
| 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 |
| HUP0402184A2 (hu) * | 2001-12-04 | 2005-02-28 | Actelion Pharmaceuticals Ltd. | 4-(Piperidil- és pirrolidil-alkil-ureido)-kinolin-származékok mint urotenzin II receptor antagonisták és ezeket tartalmazó gyógyszerkészítmények |
| BR0314353A (pt) | 2002-09-17 | 2005-07-19 | Actelion Pharmaceuticals Ltd | Compostos, composições farmacêuticas, uso de um ou mais compostos em combinação com outros compostos farmacologicamente ativos, e, método para tratar um paciente que sofre de um distúrbio |
| AU2003291303A1 (en) | 2002-11-06 | 2004-06-03 | Smithkline Beecham Corporation | Sulfonamides |
| WO2004043368A2 (en) | 2002-11-06 | 2004-05-27 | Smithkline Beecham Corporation | Sulfonamides |
| WO2004043917A1 (en) | 2002-11-06 | 2004-05-27 | Smithkline Beecham Corporation | Sulfonamides |
| WO2004043369A2 (en) | 2002-11-06 | 2004-05-27 | Smithkline Beecham Corporation | Sulfonamides |
| TW200418831A (en) | 2002-11-06 | 2004-10-01 | Smithkline Beecham Corp | Sulfonamides |
| EP2415760A3 (en) | 2003-02-20 | 2012-02-22 | Encysive Pharmaceuticals, Inc. | CCR-9 antagonists |
| JP2006525273A (ja) * | 2003-05-07 | 2006-11-09 | アクテリオン ファマシューティカルズ リミテッド | 新規なピペラジン誘導体 |
-
2004
- 2004-09-21 BR BRPI0414777-4A patent/BRPI0414777A/pt not_active Application Discontinuation
- 2004-09-21 CN CN2004800277254A patent/CN1856305B/zh not_active Expired - Fee Related
- 2004-09-21 DE DE602004020486T patent/DE602004020486D1/de not_active Expired - Lifetime
- 2004-09-21 CA CA2540196A patent/CA2540196C/en not_active Expired - Fee Related
- 2004-09-21 JP JP2006527332A patent/JP4851328B2/ja not_active Expired - Fee Related
- 2004-09-21 RU RU2006113948/04A patent/RU2006113948A/ru unknown
- 2004-09-21 AT AT04765436T patent/ATE427748T1/de not_active IP Right Cessation
- 2004-09-21 EP EP04765436A patent/EP1670470B1/en not_active Expired - Lifetime
- 2004-09-21 MX MXPA06003264A patent/MXPA06003264A/es unknown
- 2004-09-21 KR KR1020067005848A patent/KR20070014108A/ko not_active Withdrawn
- 2004-09-21 AU AU2004275488A patent/AU2004275488A1/en not_active Abandoned
- 2004-09-21 WO PCT/EP2004/010559 patent/WO2005030209A1/en not_active Ceased
- 2004-09-21 US US10/573,516 patent/US7750161B2/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 |
|---|---|
| MXPA06003264A (es) | 2006-06-08 |
| RU2006113948A (ru) | 2007-11-10 |
| ZA200602442B (en) | 2007-09-26 |
| CN1856305A (zh) | 2006-11-01 |
| ATE427748T1 (de) | 2009-04-15 |
| IL174497A0 (en) | 2006-08-01 |
| WO2005030209A8 (en) | 2006-05-11 |
| CN1856305B (zh) | 2010-04-28 |
| BRPI0414777A (pt) | 2006-11-21 |
| WO2005030209A1 (en) | 2005-04-07 |
| AR045949A1 (es) | 2005-11-16 |
| CA2540196A1 (en) | 2005-04-07 |
| US20070043081A1 (en) | 2007-02-22 |
| CA2540196C (en) | 2012-03-20 |
| US7750161B2 (en) | 2010-07-06 |
| KR20070014108A (ko) | 2007-01-31 |
| EP1670470A1 (en) | 2006-06-21 |
| NO20061395L (no) | 2006-06-22 |
| DE602004020486D1 (de) | 2009-05-20 |
| EP1670470B1 (en) | 2009-04-08 |
| JP4851328B2 (ja) | 2012-01-11 |
| TW200526630A (en) | 2005-08-16 |
| JP2007506692A (ja) | 2007-03-22 |
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| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |