JP2011516498A5 - - Google Patents
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- Publication number
- JP2011516498A5 JP2011516498A5 JP2011503219A JP2011503219A JP2011516498A5 JP 2011516498 A5 JP2011516498 A5 JP 2011516498A5 JP 2011503219 A JP2011503219 A JP 2011503219A JP 2011503219 A JP2011503219 A JP 2011503219A JP 2011516498 A5 JP2011516498 A5 JP 2011516498A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- triazolo
- dihydro
- oxo
- compound
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 108010087894 Fatty acid desaturases Proteins 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 102000016553 Stearoyl-CoA Desaturase Human genes 0.000 claims description 6
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 6
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 4
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 claims description 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 4
- 208000032109 Transient ischaemic attack Diseases 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 201000010875 transient cerebral ischemia Diseases 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- HCEBEAXUZILJMF-UHFFFAOYSA-N tert-butyl n-[2-[(3,4-dichlorophenyl)methyl]-3-oxo-[1,2,4]triazolo[4,3-a]pyridin-6-yl]carbamate Chemical compound O=C1N2C=C(NC(=O)OC(C)(C)C)C=CC2=NN1CC1=CC=C(Cl)C(Cl)=C1 HCEBEAXUZILJMF-UHFFFAOYSA-N 0.000 claims description 3
- JSCHCUAUVSTTPV-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)methyl]-n-(2-hydroxyethyl)-3-oxo-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamide Chemical compound O=C1N2C=C(C(=O)NCCO)C=CC2=NN1CC1=CC=C(Cl)C(Cl)=C1 JSCHCUAUVSTTPV-UHFFFAOYSA-N 0.000 claims description 2
- JDRORHFKYOKHML-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)methyl]-n-hexyl-3-oxo-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamide Chemical compound O=C1N2C=C(C(=O)NCCCCCC)C=CC2=NN1CC1=CC=C(Cl)C(Cl)=C1 JDRORHFKYOKHML-UHFFFAOYSA-N 0.000 claims description 2
- QLZBPKABEYQQMV-UHFFFAOYSA-N 2-[3-(2,5-dichlorophenoxy)propyl]-n-(2-hydroxyethyl)-3-oxo-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamide Chemical compound O=C1N2C=C(C(=O)NCCO)C=CC2=NN1CCCOC1=CC(Cl)=CC=C1Cl QLZBPKABEYQQMV-UHFFFAOYSA-N 0.000 claims description 2
- KAQMFLNMRQOAKK-UHFFFAOYSA-N 2-[[4-chloro-3-(trifluoromethyl)phenyl]methyl]-3-oxo-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamide Chemical compound O=C1N2C=C(C(=O)N)C=CC2=NN1CC1=CC=C(Cl)C(C(F)(F)F)=C1 KAQMFLNMRQOAKK-UHFFFAOYSA-N 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 208000002249 Diabetes Complications Diseases 0.000 claims description 2
- 206010012655 Diabetic complications Diseases 0.000 claims description 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims description 2
- 206010022489 Insulin Resistance Diseases 0.000 claims description 2
- 208000032382 Ischaemic stroke Diseases 0.000 claims description 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- 208000018262 Peripheral vascular disease Diseases 0.000 claims description 2
- 208000017442 Retinal disease Diseases 0.000 claims description 2
- 206010038923 Retinopathy Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 2
- 208000029078 coronary artery disease Diseases 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- RGMNKANICOKRFW-UHFFFAOYSA-N ethyl 2-[(3,4-dichlorophenyl)methyl]-3-oxo-[1,2,4]triazolo[4,3-a]pyridine-6-carboxylate Chemical compound O=C1N2C=C(C(=O)OCC)C=CC2=NN1CC1=CC=C(Cl)C(Cl)=C1 RGMNKANICOKRFW-UHFFFAOYSA-N 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 208000019622 heart disease Diseases 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 230000000302 ischemic effect Effects 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- KOZNWTGOMQFSMO-UHFFFAOYSA-N n-[2-[[4-chloro-3-(trifluoromethyl)phenyl]methyl]-3-oxo-[1,2,4]triazolo[4,3-a]pyridin-6-yl]-2-hydroxyacetamide Chemical compound O=C1N2C=C(NC(=O)CO)C=CC2=NN1CC1=CC=C(Cl)C(C(F)(F)F)=C1 KOZNWTGOMQFSMO-UHFFFAOYSA-N 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- -1 1- (4-fluoro-3- (trifluoromethyl) phenyl) ethyl Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- DDDARTXFGYJQFS-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)methyl]-3-oxo-[1,2,4]triazolo[4,3-a]pyridine-6-carboxylic acid Chemical compound O=C1N2C=C(C(=O)O)C=CC2=NN1CC1=CC=C(Cl)C(Cl)=C1 DDDARTXFGYJQFS-UHFFFAOYSA-N 0.000 description 1
- 229940123980 Desaturase inhibitor Drugs 0.000 description 1
- QRBKGBJKWUCYRX-UHFFFAOYSA-N n-[2-[(3,4-dichlorophenyl)methyl]-3-oxo-[1,2,4]triazolo[4,3-a]pyridin-6-yl]-2,3-dihydroxypropanamide Chemical compound O=C1N2C=C(NC(=O)C(O)CO)C=CC2=NN1CC1=CC=C(Cl)C(Cl)=C1 QRBKGBJKWUCYRX-UHFFFAOYSA-N 0.000 description 1
- QSJOHKPAPMCPSV-LBPRGKRZSA-N n-butyl-2-[(1s)-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethyl]-3-oxo-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamide Chemical compound C1([C@H](C)N2N=C3C=CC(=CN3C2=O)C(=O)NCCCC)=CC=C(F)C(C(F)(F)F)=C1 QSJOHKPAPMCPSV-LBPRGKRZSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4262508P | 2008-04-04 | 2008-04-04 | |
| US61/042,625 | 2008-04-04 | ||
| PCT/US2009/039503 WO2009137201A1 (en) | 2008-04-04 | 2009-04-03 | Triazolopyridinone derivatives for use as stearoyl coa desaturase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011516498A JP2011516498A (ja) | 2011-05-26 |
| JP2011516498A5 true JP2011516498A5 (https=) | 2013-05-02 |
Family
ID=41119775
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011503219A Withdrawn JP2011516498A (ja) | 2008-04-04 | 2009-04-03 | ステアロイル−ＣｏＡデサチュラーゼの阻害剤として使用するためのトリアゾロピリジノン誘導体 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8088792B2 (https=) |
| EP (1) | EP2268637A1 (https=) |
| JP (1) | JP2011516498A (https=) |
| KR (1) | KR20100132999A (https=) |
| AU (1) | AU2009244664A1 (https=) |
| BR (1) | BRPI0910987A2 (https=) |
| CA (1) | CA2719288A1 (https=) |
| MX (1) | MX2010010949A (https=) |
| WO (1) | WO2009137201A1 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101522676A (zh) * | 2006-10-05 | 2009-09-02 | Cv医药有限公司 | 用作硬脂酰-CoA脱氢酶抑制剂的双环含氮杂环化合物 |
| EP2131844A1 (en) * | 2007-04-09 | 2009-12-16 | CV Therapeutics Inc. | PTERIDINONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS |
| US20090105283A1 (en) * | 2007-04-11 | 2009-04-23 | Dmitry Koltun | 3-HYDROQUINAZOLIN-4-ONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS |
| CA2719362A1 (en) * | 2008-04-04 | 2009-10-08 | Gilead Sciences, Inc. | Pyrrolotriazinone derivatives for use as stearoyl coa desaturase inhibitors |
| US8088792B2 (en) * | 2008-04-04 | 2012-01-03 | Gilead Sciences, Inc. | Triazolopyridinone derivatives for use as stearoyl CoA desaturase inhibitors |
| WO2010045374A1 (en) * | 2008-10-15 | 2010-04-22 | Gilead Palo Alto, Inc. | 3-hydroquinazolin-4-one derivatives for use as stearoyl coa desaturase inhibitors |
| WO2010096722A1 (en) | 2009-02-20 | 2010-08-26 | Takeda Pharmaceutical Company Limited | 3-oxo-2, 3-dihydro- [1,2, 4] triazolo [4, 3-a]pyridines as soluble epoxide hydrolase (seh) inhibitors |
| KR101360176B1 (ko) * | 2011-05-04 | 2014-02-12 | 제일약품주식회사 | 신규한 트리아졸로피리딘 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 포함하는 약학적 조성물 |
| WO2016153938A1 (en) * | 2015-03-25 | 2016-09-29 | Biosynthetic Technologies, Llc | Ester compounds including triesters having terminal vicinal acyl groups |
| US20170081323A1 (en) | 2015-09-18 | 2017-03-23 | F. Hoffmann-La Roche Ag | Triazolones derivatives for use in the treatment, amelioration or prevention of a viral disease |
| US20170081324A1 (en) * | 2015-09-18 | 2017-03-23 | F. Hoffmann-La Roche Ag | Triazolones derivatives and their use in the treatment, amelioration or prevention of a viral disease |
| US11970486B2 (en) | 2016-10-24 | 2024-04-30 | Janssen Pharmaceutica Nv | Compounds and uses thereof |
| EA201991650A1 (ru) | 2017-01-06 | 2020-01-20 | Юманити Терапьютикс, Инк. | Способы лечения неврологических расстройств |
| CA3083000A1 (en) | 2017-10-24 | 2019-05-02 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| BR112020019191A2 (pt) | 2018-03-23 | 2021-01-05 | Yumanity Therapeutics, Inc. | Compostos e seus usos |
| MX2021008903A (es) | 2019-01-24 | 2021-11-04 | Yumanity Therapeutics Inc | Compuestos y usos de los mismos. |
| EA202192047A1 (ru) | 2019-11-13 | 2021-12-08 | Юманити Терапьютикс, Инк. | Соединения и их применение |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3845770A (en) * | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| US4326525A (en) * | 1980-10-14 | 1982-04-27 | Alza Corporation | Osmotic device that improves delivery properties of agent in situ |
| US5364620A (en) * | 1983-12-22 | 1994-11-15 | Elan Corporation, Plc | Controlled absorption diltiazem formulation for once daily administration |
| US5023252A (en) * | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
| US4992445A (en) * | 1987-06-12 | 1991-02-12 | American Cyanamid Co. | Transdermal delivery of pharmaceuticals |
| US5001139A (en) * | 1987-06-12 | 1991-03-19 | American Cyanamid Company | Enchancers for the transdermal flux of nivadipine |
| US4902514A (en) * | 1988-07-21 | 1990-02-20 | Alza Corporation | Dosage form for administering nilvadipine for treating cardiovascular symptoms |
| WO1994018981A1 (en) * | 1993-02-22 | 1994-09-01 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5821241A (en) * | 1994-02-22 | 1998-10-13 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| EP1409487A1 (en) | 1999-09-15 | 2004-04-21 | Warner-Lambert Company Llc | Pteridinones as kinase inhibitors |
| TW200420565A (en) | 2002-12-13 | 2004-10-16 | Bristol Myers Squibb Co | C-6 modified indazolylpyrrolotriazines |
| JP5080256B2 (ja) | 2004-09-20 | 2012-11-21 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 二環式複素環誘導体およびステアロイル−ＣｏＡデサチュラーゼ（ＳＣＤ）のインヒビターとしてのそれらの使用 |
| JP2009501733A (ja) * | 2005-07-20 | 2009-01-22 | 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デサチュラーゼの阻害剤としてのヘテロ芳香族化合物 |
| WO2008003753A1 (en) | 2006-07-07 | 2008-01-10 | Biovitrum Ab (Publ) | Pyrazolo [1,5-a] pyrimidine analogs for use as inhibitors of stearoyl-coa desaturase (scd) activity |
| CN101522676A (zh) * | 2006-10-05 | 2009-09-02 | Cv医药有限公司 | 用作硬脂酰-CoA脱氢酶抑制剂的双环含氮杂环化合物 |
| US7893066B2 (en) * | 2006-10-05 | 2011-02-22 | Gilead Palo Alto, Inc. | Pyridol[2,3-B]pyrazinones for use as stearoyl CoA desaturase inhibitors |
| JP2010508288A (ja) | 2006-10-27 | 2010-03-18 | ブリストル−マイヤーズ スクイブ カンパニー | キナーゼ阻害剤として有用なヘテロサイクリックアミド化合物 |
| EP2131844A1 (en) * | 2007-04-09 | 2009-12-16 | CV Therapeutics Inc. | PTERIDINONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS |
| US20080255161A1 (en) * | 2007-04-11 | 2008-10-16 | Dmitry Koltun | 3-HYDROQUINAZOLIN-4-ONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS |
| US20090105283A1 (en) * | 2007-04-11 | 2009-04-23 | Dmitry Koltun | 3-HYDROQUINAZOLIN-4-ONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS |
| US8088792B2 (en) * | 2008-04-04 | 2012-01-03 | Gilead Sciences, Inc. | Triazolopyridinone derivatives for use as stearoyl CoA desaturase inhibitors |
| CA2719362A1 (en) * | 2008-04-04 | 2009-10-08 | Gilead Sciences, Inc. | Pyrrolotriazinone derivatives for use as stearoyl coa desaturase inhibitors |
| EP2278976A1 (en) * | 2008-04-07 | 2011-02-02 | Gilead Sciences, Inc. | 2h-benzo[b][1,4]oxazin-3(4h)-one derivatives for use as stearoyl coa desaturase inhibitors |
-
2009
- 2009-04-03 US US12/417,891 patent/US8088792B2/en not_active Expired - Fee Related
- 2009-04-03 JP JP2011503219A patent/JP2011516498A/ja not_active Withdrawn
- 2009-04-03 BR BRPI0910987A patent/BRPI0910987A2/pt not_active IP Right Cessation
- 2009-04-03 EP EP09743188A patent/EP2268637A1/en not_active Withdrawn
- 2009-04-03 MX MX2010010949A patent/MX2010010949A/es not_active Application Discontinuation
- 2009-04-03 CA CA2719288A patent/CA2719288A1/en not_active Abandoned
- 2009-04-03 KR KR1020107024841A patent/KR20100132999A/ko not_active Withdrawn
- 2009-04-03 WO PCT/US2009/039503 patent/WO2009137201A1/en not_active Ceased
- 2009-04-03 AU AU2009244664A patent/AU2009244664A1/en not_active Abandoned
-
2011
- 2011-11-23 US US13/303,763 patent/US20120065227A1/en not_active Abandoned
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