JP2007500715A5 - - Google Patents
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- JP2007500715A5 JP2007500715A5 JP2006522072A JP2006522072A JP2007500715A5 JP 2007500715 A5 JP2007500715 A5 JP 2007500715A5 JP 2006522072 A JP2006522072 A JP 2006522072A JP 2006522072 A JP2006522072 A JP 2006522072A JP 2007500715 A5 JP2007500715 A5 JP 2007500715A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- hydrogen
- cycloalkyl
- group
- aralkyl
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims 45
- 239000001257 hydrogen Substances 0.000 claims 45
- 125000003710 aryl alkyl group Chemical group 0.000 claims 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 29
- 125000003118 aryl group Chemical group 0.000 claims 29
- 125000001072 heteroaryl group Chemical group 0.000 claims 29
- 125000000623 heterocyclic group Chemical group 0.000 claims 29
- 125000000217 alkyl group Chemical group 0.000 claims 22
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 21
- 125000005843 halogen group Chemical group 0.000 claims 21
- 125000001424 substituent group Chemical group 0.000 claims 21
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 18
- -1 chloro, methyl Chemical group 0.000 claims 18
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims 16
- 150000002431 hydrogen Chemical class 0.000 claims 16
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 14
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 14
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 14
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims 14
- 229940079593 drug Drugs 0.000 claims 10
- 239000003814 drug Substances 0.000 claims 10
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 9
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims 9
- 201000010099 disease Diseases 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000003367 polycyclic group Chemical group 0.000 claims 6
- 230000005856 abnormality Effects 0.000 claims 5
- 108010087894 Fatty acid desaturases Proteins 0.000 claims 4
- 102000016553 Stearoyl-CoA Desaturase Human genes 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 3
- 208000004930 Fatty Liver Diseases 0.000 claims 2
- 206010019708 Hepatic steatosis Diseases 0.000 claims 2
- 101000631826 Homo sapiens Stearoyl-CoA desaturase Proteins 0.000 claims 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 2
- 230000002159 abnormal effect Effects 0.000 claims 2
- 208000010706 fatty liver disease Diseases 0.000 claims 2
- 102000055981 human SCD1 Human genes 0.000 claims 2
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 2
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
- 231100000240 steatosis hepatitis Toxicity 0.000 claims 2
- 125000004385 trihaloalkyl group Chemical group 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- 208000002705 Glucose Intolerance Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
- HZYJFYDBOVZGIW-UHFFFAOYSA-N [4-[6-(2-phenylethoxy)pyridazin-3-yl]piperazin-1-yl]-[2-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(OCCC=3C=CC=CC=3)=CC=2)CC1 HZYJFYDBOVZGIW-UHFFFAOYSA-N 0.000 claims 1
- WBLYCICMFISNEP-UHFFFAOYSA-N [4-[6-(2-phenylethylamino)pyridazin-3-yl]piperazin-1-yl]-[2-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(NCCC=3C=CC=CC=3)=CC=2)CC1 WBLYCICMFISNEP-UHFFFAOYSA-N 0.000 claims 1
- KIMDQFVNARRKRG-UHFFFAOYSA-N [4-[6-(2-phenylethylsulfanyl)pyridazin-3-yl]piperazin-1-yl]-[2-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(SCCC=3C=CC=CC=3)=CC=2)CC1 KIMDQFVNARRKRG-UHFFFAOYSA-N 0.000 claims 1
- KOTQLIKJTDTRGO-UHFFFAOYSA-N [4-[6-(2-phenylethylsulfinyl)pyridazin-3-yl]piperazin-1-yl]-[2-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)S(=O)CCC=2C=CC=CC=2)CC1 KOTQLIKJTDTRGO-UHFFFAOYSA-N 0.000 claims 1
- SLRFPPGXCUIOEE-UHFFFAOYSA-N [4-[6-(2-phenylethylsulfonyl)pyridazin-3-yl]piperazin-1-yl]-[2-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)N1CCN(C=2N=NC(=CC=2)S(=O)(=O)CCC=2C=CC=CC=2)CC1 SLRFPPGXCUIOEE-UHFFFAOYSA-N 0.000 claims 1
- ACASVUBSIKGUOX-UHFFFAOYSA-N [4-[6-(3-methylbutylsulfanyl)pyridazin-3-yl]piperazin-1-yl]-[2-(trifluoromethyl)phenyl]methanone Chemical compound N1=NC(SCCC(C)C)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 ACASVUBSIKGUOX-UHFFFAOYSA-N 0.000 claims 1
- XTRLGWKVRHBAFP-UHFFFAOYSA-N [4-[6-[methyl(2-phenylethyl)amino]pyridazin-3-yl]piperazin-1-yl]-[2-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(N2CCN(CC2)C(=O)C=2C(=CC=CC=2)C(F)(F)F)N=NC=1N(C)CCC1=CC=CC=C1 XTRLGWKVRHBAFP-UHFFFAOYSA-N 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 1
- UPDYFVHFGPENGT-UHFFFAOYSA-N n-[6-[4-[2-(trifluoromethyl)benzoyl]piperazin-1-yl]pyridazin-3-yl]propane-1-sulfonamide Chemical compound N1=NC(NS(=O)(=O)CCC)=CC=C1N1CCN(C(=O)C=2C(=CC=CC=2)C(F)(F)F)CC1 UPDYFVHFGPENGT-UHFFFAOYSA-N 0.000 claims 1
- 201000009104 prediabetes syndrome Diseases 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49109503P | 2003-07-30 | 2003-07-30 | |
| US49111603P | 2003-07-30 | 2003-07-30 | |
| US60/491,095 | 2003-07-30 | ||
| US60/491,116 | 2003-07-30 | ||
| PCT/US2004/024541 WO2005011653A2 (en) | 2003-07-30 | 2004-07-29 | Pyridazine derivatives and their use as therapeutic agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007500715A JP2007500715A (ja) | 2007-01-18 |
| JP2007500715A5 true JP2007500715A5 (https=) | 2007-09-13 |
| JP4831577B2 JP4831577B2 (ja) | 2011-12-07 |
Family
ID=34118852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006522072A Expired - Fee Related JP4831577B2 (ja) | 2003-07-30 | 2004-07-29 | ピリダジン誘導体および治療剤としての用途 |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US7514436B2 (https=) |
| EP (2) | EP2316826A1 (https=) |
| JP (1) | JP4831577B2 (https=) |
| KR (1) | KR20060037410A (https=) |
| CN (1) | CN101712653A (https=) |
| AT (1) | ATE555789T1 (https=) |
| AU (1) | AU2004261249B2 (https=) |
| BR (1) | BRPI0412343A (https=) |
| CA (1) | CA2533897A1 (https=) |
| EC (1) | ECSP066315A (https=) |
| ES (1) | ES2386353T3 (https=) |
| IL (1) | IL173032A0 (https=) |
| MA (1) | MA28009A1 (https=) |
| NO (1) | NO20060974L (https=) |
| RU (1) | RU2006105716A (https=) |
| SG (1) | SG145699A1 (https=) |
| TN (1) | TNSN06032A1 (https=) |
| WO (1) | WO2005011653A2 (https=) |
Families Citing this family (68)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7517884B2 (en) | 1998-03-30 | 2009-04-14 | Kalypsys Inc. | Sulfonyl-substituted bicyclic compounds as modulators of PPAR |
| US20040226056A1 (en) * | 1998-12-22 | 2004-11-11 | Myriad Genetics, Incorporated | Compositions and methods for treating neurological disorders and diseases |
| DE602004017316D1 (de) | 2003-07-24 | 2008-12-04 | Euro Celtique Sa | Heteroaryl-tetrahydropyridylverbindungen, die sich für die behandlung bzw. die prävention von schmerzen eignen |
| PL1648874T3 (pl) | 2003-07-30 | 2012-04-30 | Xenon Pharmaceuticals Inc | Pochodne piperazyny i ich zastosowanie jako środków leczniczych |
| CA2533897A1 (en) * | 2003-07-30 | 2005-02-10 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
| US7754711B2 (en) * | 2003-07-30 | 2010-07-13 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
| US7759348B2 (en) | 2003-07-30 | 2010-07-20 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
| MX2007003332A (es) | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de estearoil-coa-desaturasa. |
| BRPI0515482A (pt) | 2004-09-20 | 2008-07-22 | Xenon Pharmaceuticals Inc | derivados heterocìclicos e seus usos como agentes terapêuticos |
| BRPI0515500A (pt) | 2004-09-20 | 2008-07-29 | Xenon Pharmaceuticals Inc | derivados piridazina para inibição de estearoil-coa-desaturase |
| AU2005286647A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| CN101084211A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其作为治疗剂的用途 |
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| AU2005286728A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-CoA desaturase |
| CA2585172C (en) | 2004-10-29 | 2014-08-12 | Kalypsys, Inc. | Sulfonyl-substituted bicyclic compounds as modulators of ppar |
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| HUE040020T2 (hu) | 2005-10-25 | 2019-02-28 | Kalypsys Inc | PPAR modulátorok sói és eljárások metabolikus betegségek kezelésére |
| EP1966183A4 (en) * | 2005-12-20 | 2010-12-29 | Merck Frosst Canada Ltd | HETEROAROMATIC COMPOUNDS AS INHIBITORS OF STEAROYL-COENZYME A-DELTA-9-DESATURASE |
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| WO2007143597A2 (en) | 2006-06-05 | 2007-12-13 | Novartis Ag | Organic compounds |
| JP2009539884A (ja) * | 2006-06-12 | 2009-11-19 | メルク フロスト カナダ リミテツド | ステアロイル−コエンザイムａデルタ−９デサチュラーゼのインヒビターとしてのアゼチジン誘導体 |
| MX2009002019A (es) | 2006-08-24 | 2009-03-09 | Novartis Ag | Derivados de 2-(pirazin-2-il)-tiazol y 2-(1h-pirazol-3-il)-tiazol asi como compuestos relacionados como inhibidores de la estearoil-coa-desaturasa (scd) para el tratamiento de trastornos metabolicos, cardiovasculares, y otros. |
| WO2008062276A2 (en) * | 2006-11-20 | 2008-05-29 | Glenmark Pharmaceuticals S.A. | Acetylene derivatives as stearoyl coa desaturase inhibitors |
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| US8575167B2 (en) | 2007-02-06 | 2013-11-05 | Takeda Pharmaceutical Company Limited | Spiro compounds having stearoyl-CoA desaturase action |
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| CA2681162C (en) * | 2007-03-15 | 2015-11-24 | Novartis Ag | Benzyl and pyridine derivatives as modulators of hedgehog pathway |
| CA2685266C (en) * | 2007-04-27 | 2014-01-28 | Purdue Pharma L.P. | Trpv1 antagonists and uses thereof for the treatment of prevention of pain, ui and ulcer, ibd, or ibs in an animal |
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| GB0722077D0 (en) | 2007-11-09 | 2007-12-19 | Smithkline Beecham Corp | Compounds |
| US20100041663A1 (en) | 2008-07-18 | 2010-02-18 | Novartis Ag | Organic Compounds as Smo Inhibitors |
| US8673917B2 (en) | 2008-09-09 | 2014-03-18 | Sanofi | 2-heteroaryl-pyrrolo [3,4-C]pyrrole derivatives, and use thereof as SCD inhibitors |
| WO2010071610A1 (en) | 2008-12-19 | 2010-06-24 | Agency For Science, Technology And Research (A*Star) | Severe chikungunya biomarkers |
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| GB0907425D0 (en) * | 2009-04-29 | 2009-06-10 | Glaxo Group Ltd | Compounds |
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| FR2948939B1 (fr) * | 2009-08-05 | 2013-03-22 | Pf Medicament | Derives de 2h pyridazin-3-ones, leur preparation et leur application en therapeutique humaine |
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| SG11201811023UA (en) * | 2016-06-23 | 2019-01-30 | St Jude Childrens Res Hospital | Small molecule modulators of pantothenate kinases |
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| EP3852791B1 (en) | 2018-09-19 | 2024-07-03 | Novo Nordisk Health Care AG | Activating pyruvate kinase r |
| HRP20251148T1 (hr) | 2019-09-19 | 2025-11-21 | Novo Nordisk Health Care Ag | Pripravci koji aktiviraju piruvat-kinazu r (pkr) |
| MX2023001818A (es) | 2020-08-13 | 2023-03-13 | Boehringer Ingelheim Int | Compuestos para usarse en tratamiento de deterioro cognitivo asociado con la esquizofrenia. |
| IL301829A (en) | 2020-10-13 | 2023-06-01 | Boehringer Ingelheim Int | Process of reworking |
| US12128035B2 (en) | 2021-03-19 | 2024-10-29 | Novo Nordisk Health Care Ag | Activating pyruvate kinase R |
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| DE19614204A1 (de) * | 1996-04-10 | 1997-10-16 | Thomae Gmbh Dr K | Carbonsäurederivate, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
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-
2004
- 2004-07-29 CA CA002533897A patent/CA2533897A1/en not_active Abandoned
- 2004-07-29 AU AU2004261249A patent/AU2004261249B2/en not_active Ceased
- 2004-07-29 KR KR1020067002006A patent/KR20060037410A/ko not_active Ceased
- 2004-07-29 RU RU2006105716/04A patent/RU2006105716A/ru not_active Application Discontinuation
- 2004-07-29 US US10/566,856 patent/US7514436B2/en not_active Expired - Fee Related
- 2004-07-29 AT AT04779555T patent/ATE555789T1/de active
- 2004-07-29 SG SG200805678-0A patent/SG145699A1/en unknown
- 2004-07-29 ES ES04779555T patent/ES2386353T3/es not_active Expired - Lifetime
- 2004-07-29 CN CN200910224929A patent/CN101712653A/zh active Pending
- 2004-07-29 BR BRPI0412343-3A patent/BRPI0412343A/pt not_active IP Right Cessation
- 2004-07-29 JP JP2006522072A patent/JP4831577B2/ja not_active Expired - Fee Related
- 2004-07-29 EP EP10184440A patent/EP2316826A1/en not_active Withdrawn
- 2004-07-29 WO PCT/US2004/024541 patent/WO2005011653A2/en not_active Ceased
- 2004-07-29 EP EP04779555A patent/EP1651616B1/en not_active Expired - Lifetime
-
2006
- 2006-01-09 IL IL173032A patent/IL173032A0/en unknown
- 2006-01-25 EC EC2006006315A patent/ECSP066315A/es unknown
- 2006-01-27 TN TNP2006000032A patent/TNSN06032A1/en unknown
- 2006-02-27 MA MA28837A patent/MA28009A1/fr unknown
- 2006-02-28 NO NO20060974A patent/NO20060974L/no not_active Application Discontinuation
-
2009
- 2009-02-20 US US12/390,117 patent/US8148378B2/en not_active Expired - Fee Related
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