AU2007303056A1 - Bicyclic nitrogen-containing heterocyclic compounds for use as stearoyl CoA desaturase inhibitors - Google Patents
Bicyclic nitrogen-containing heterocyclic compounds for use as stearoyl CoA desaturase inhibitors Download PDFInfo
- Publication number
- AU2007303056A1 AU2007303056A1 AU2007303056A AU2007303056A AU2007303056A1 AU 2007303056 A1 AU2007303056 A1 AU 2007303056A1 AU 2007303056 A AU2007303056 A AU 2007303056A AU 2007303056 A AU2007303056 A AU 2007303056A AU 2007303056 A1 AU2007303056 A1 AU 2007303056A1
- Authority
- AU
- Australia
- Prior art keywords
- amino
- methyl
- oxo
- hydropyridino
- pyrazin
- 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
- -1 Bicyclic nitrogen-containing heterocyclic compounds Chemical class 0.000 title claims description 123
- 108010087894 Fatty acid desaturases Proteins 0.000 title claims description 64
- 102000016553 Stearoyl-CoA Desaturase Human genes 0.000 title claims 2
- 239000003112 inhibitor Substances 0.000 title description 12
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 287
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 214
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 175
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 166
- 150000001875 compounds Chemical class 0.000 claims description 160
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 118
- 125000000217 alkyl group Chemical group 0.000 claims description 94
- 125000003118 aryl group Chemical group 0.000 claims description 70
- 125000001072 heteroaryl group Chemical group 0.000 claims description 70
- 125000001424 substituent group Chemical group 0.000 claims description 54
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 51
- 201000010099 disease Diseases 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 125000000623 heterocyclic group Chemical group 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 125000000304 alkynyl group Chemical group 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- 125000002947 alkylene group Chemical group 0.000 claims description 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 8
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- 241000124008 Mammalia Species 0.000 claims description 7
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
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- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
- 239000000651 prodrug Substances 0.000 claims description 5
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- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 4
- 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- NIPZZXUFJPQHNH-UHFFFAOYSA-M pyrazine-2-carboxylate Chemical compound [O-]C(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-M 0.000 claims description 2
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 6
- XZOWIJDBQIHMFC-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O.CCCC(N)=O XZOWIJDBQIHMFC-UHFFFAOYSA-N 0.000 claims 5
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 claims 1
- WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 claims 1
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 claims 1
- 102100028897 Stearoyl-CoA desaturase Human genes 0.000 description 60
- 239000000203 mixture Substances 0.000 description 59
- 238000002360 preparation method Methods 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 150000001412 amines Chemical class 0.000 description 24
- 229910052736 halogen Inorganic materials 0.000 description 23
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 22
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Classifications
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- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
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- C07—ORGANIC CHEMISTRY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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Landscapes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84964806P | 2006-10-05 | 2006-10-05 | |
| US60/849,648 | 2006-10-05 | ||
| PCT/US2007/080627 WO2008043087A2 (en) | 2006-10-05 | 2007-10-05 | Bicyclic nitrogen-containing heterocyclic compounds for use as stearoyl coa desaturase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2007303056A1 true AU2007303056A1 (en) | 2008-04-10 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2007303056A Abandoned AU2007303056A1 (en) | 2006-10-05 | 2007-10-05 | Bicyclic nitrogen-containing heterocyclic compounds for use as stearoyl CoA desaturase inhibitors |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US7732453B2 (enExample) |
| EP (1) | EP2066665A2 (enExample) |
| JP (1) | JP2010505881A (enExample) |
| KR (1) | KR20090057416A (enExample) |
| CN (1) | CN101522676A (enExample) |
| AU (1) | AU2007303056A1 (enExample) |
| BR (1) | BRPI0717502A2 (enExample) |
| CA (1) | CA2665476A1 (enExample) |
| IL (1) | IL197828A0 (enExample) |
| MX (1) | MX2009003658A (enExample) |
| RU (1) | RU2009112397A (enExample) |
| WO (1) | WO2008043087A2 (enExample) |
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| JP2010505881A (ja) * | 2006-10-05 | 2010-02-25 | ギリアード・パロ・アルト・インコーポレイテッド | ステアロイルＣｏＡデサチュラーゼインヒビターとして使用するための二環式窒素含有複素環式化合物 |
| US7893066B2 (en) * | 2006-10-05 | 2011-02-22 | Gilead Palo Alto, Inc. | Pyridol[2,3-B]pyrazinones for use as stearoyl CoA desaturase inhibitors |
| 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 |
| US20080255161A1 (en) * | 2007-04-11 | 2008-10-16 | Dmitry Koltun | 3-HYDROQUINAZOLIN-4-ONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS |
| PT2247292T (pt) * | 2008-03-05 | 2017-07-17 | Merck Patent Gmbh | Derivados de piridopirazinonas como estimulantes da secreção de insulina, procedimentos para a sua obtenção e a sua utilização no tratamento da diabetes |
| KR20100132999A (ko) * | 2008-04-04 | 2010-12-20 | 길리애드 사이언시즈, 인코포레이티드 | 스테아로일 ＣｏＡ 불포화 효소 억제제로서 사용하기 위한 트리아졸로피리디논 유도체 |
| EP2274308A1 (en) * | 2008-04-04 | 2011-01-19 | Gilead Sciences, Inc. | Pyrrolotriazinone derivatives for use as stearoyl coa desaturase inhibitors |
| WO2009126123A1 (en) * | 2008-04-10 | 2009-10-15 | Cv Therapeutics Inc. | Bicyclic nitrogen containing heterocyclic compounds for use as stearoyl coa desaturase inhibitors |
| US20100267752A1 (en) * | 2008-10-15 | 2010-10-21 | Gilead Palo Alto, Inc. | 3-HYDROQUINAZOLIN-4-ONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS |
| JP6254087B2 (ja) | 2011-10-15 | 2017-12-27 | ジェネンテック， インコーポレイテッド | 癌を治療するためのｓｃｄ１アンタゴニスト |
| RU2606230C1 (ru) * | 2015-10-20 | 2017-01-10 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | (Z)-Этил 2-(4-(4-хлорфенил)-2,4-диоксо-3-(3-оксо-3,4-дигидрохиноксалин-2(1Н)-илиден)бутанамидо)-4-метил-5-фенилтиофен-3-карбоксилат, обладающий противодиабетической активностью, и способ его получения |
| AU2017236879B2 (en) * | 2016-03-22 | 2022-07-21 | Balchem Corporation | Compositions comprising choline |
| CN110099898B (zh) | 2016-10-24 | 2023-07-25 | 优曼尼蒂治疗公司 | 化合物及其用途 |
| KR20190108118A (ko) | 2017-01-06 | 2019-09-23 | 유마니티 테라퓨틱스, 인크. | 신경계 장애의 치료를 위한 방법 |
| EP3700934A4 (en) | 2017-10-24 | 2021-10-27 | Yumanity Therapeutics, Inc. | COMPOUNDS AND USES OF THESE COMPOUNDS |
| BR112020019191A2 (pt) | 2018-03-23 | 2021-01-05 | Yumanity Therapeutics, Inc. | Compostos e seus usos |
| EP3914593A4 (en) | 2019-01-24 | 2022-11-02 | Yumanity Therapeutics, Inc. | CONNECTIONS AND USES THEREOF |
| EA202192047A1 (ru) | 2019-11-13 | 2021-12-08 | Юманити Терапьютикс, Инк. | Соединения и их применение |
| CN118161500A (zh) | 2019-11-25 | 2024-06-11 | 安进公司 | 作为δ-5脱饱和酶抑制剂的杂环化合物以及使用方法 |
| JP2023549540A (ja) | 2020-11-18 | 2023-11-27 | デシフェラ・ファーマシューティカルズ，エルエルシー | Ｇｃｎ２およびｐｅｒｋキナーゼ阻害剤およびその使用方法 |
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| US5023252A (en) * | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
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| US4992445A (en) * | 1987-06-12 | 1991-02-12 | American Cyanamid Co. | Transdermal delivery of pharmaceuticals |
| CA2020073A1 (en) | 1989-07-03 | 1991-01-04 | Eric E. Allen | Substituted quinazolinones as angiotensin ii antagonists |
| KR20010042298A (ko) * | 1998-03-31 | 2001-05-25 | 로즈 암스트롱, 크리스틴 에이. 트러트웨인 | 인자 Ｘａ 및 트롬빈과 같은 세린 프로테아제억제제로서의 퀴녹살리논 |
| KR20010083092A (ko) | 1998-07-06 | 2001-08-31 | 스티븐 비. 데이비스 | 이중 안지오텐신 엔도텔린 수용체 길항제로서의 비페닐술폰아미드 |
| CA2393896A1 (en) | 1999-09-15 | 2001-03-22 | Warner-Lambert Company | Pteridinones as kinase inhibitors |
| WO2002076954A1 (en) * | 2001-03-23 | 2002-10-03 | Smithkline Beecham Corporation | Compounds useful as kinase inhibitors for the treatment of hyperproliferative diseases |
| WO2003076416A1 (en) | 2002-03-08 | 2003-09-18 | Warner-Lambert Company Llc | Oxo azabicyclic compounds |
| US7196090B2 (en) * | 2002-07-25 | 2007-03-27 | Warner-Lambert Company | Kinase inhibitors |
| US20040142950A1 (en) | 2003-01-17 | 2004-07-22 | Bunker Amy Mae | Amide and ester matrix metalloproteinase inhibitors |
| CN1829701A (zh) * | 2003-07-30 | 2006-09-06 | 泽农医药公司 | 哌嗪衍生物和它们作为治疗剂的用途 |
| EP1830869B1 (en) | 2004-12-24 | 2013-05-22 | Spinifex Pharmaceuticals Pty Ltd | Method of treatment or prophylaxis |
| JP2010505881A (ja) * | 2006-10-05 | 2010-02-25 | ギリアード・パロ・アルト・インコーポレイテッド | ステアロイルＣｏＡデサチュラーゼインヒビターとして使用するための二環式窒素含有複素環式化合物 |
| US7893066B2 (en) | 2006-10-05 | 2011-02-22 | Gilead Palo Alto, Inc. | Pyridol[2,3-B]pyrazinones for use as stearoyl CoA desaturase inhibitors |
| 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 |
| US20080255161A1 (en) | 2007-04-11 | 2008-10-16 | Dmitry Koltun | 3-HYDROQUINAZOLIN-4-ONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS |
| EP2274308A1 (en) | 2008-04-04 | 2011-01-19 | Gilead Sciences, Inc. | Pyrrolotriazinone derivatives for use as stearoyl coa desaturase inhibitors |
| KR20100132999A (ko) | 2008-04-04 | 2010-12-20 | 길리애드 사이언시즈, 인코포레이티드 | 스테아로일 ＣｏＡ 불포화 효소 억제제로서 사용하기 위한 트리아졸로피리디논 유도체 |
-
2007
- 2007-10-05 JP JP2009531633A patent/JP2010505881A/ja active Pending
- 2007-10-05 MX MX2009003658A patent/MX2009003658A/es not_active Application Discontinuation
- 2007-10-05 CA CA002665476A patent/CA2665476A1/en not_active Abandoned
- 2007-10-05 WO PCT/US2007/080627 patent/WO2008043087A2/en not_active Ceased
- 2007-10-05 RU RU2009112397/04A patent/RU2009112397A/ru not_active Application Discontinuation
- 2007-10-05 BR BRPI0717502-7A patent/BRPI0717502A2/pt not_active IP Right Cessation
- 2007-10-05 US US11/868,386 patent/US7732453B2/en not_active Expired - Fee Related
- 2007-10-05 KR KR1020097006958A patent/KR20090057416A/ko not_active Withdrawn
- 2007-10-05 AU AU2007303056A patent/AU2007303056A1/en not_active Abandoned
- 2007-10-05 CN CNA2007800367748A patent/CN101522676A/zh active Pending
- 2007-10-05 EP EP07853820A patent/EP2066665A2/en not_active Ceased
-
2009
- 2009-03-26 IL IL197828A patent/IL197828A0/en unknown
-
2010
- 2010-04-26 US US12/767,515 patent/US8148376B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008043087A2 (en) | 2008-04-10 |
| MX2009003658A (es) | 2009-04-22 |
| JP2010505881A (ja) | 2010-02-25 |
| CA2665476A1 (en) | 2008-04-10 |
| US8148376B2 (en) | 2012-04-03 |
| RU2009112397A (ru) | 2010-10-10 |
| KR20090057416A (ko) | 2009-06-05 |
| EP2066665A2 (en) | 2009-06-10 |
| BRPI0717502A2 (pt) | 2015-06-16 |
| WO2008043087A3 (en) | 2008-05-22 |
| IL197828A0 (en) | 2009-12-24 |
| US20080139570A1 (en) | 2008-06-12 |
| US20100204238A1 (en) | 2010-08-12 |
| US7732453B2 (en) | 2010-06-08 |
| CN101522676A (zh) | 2009-09-02 |
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