ES2575955T3 - Derivados de triazol como inhibidores de SCD - Google Patents
Derivados de triazol como inhibidores de SCD Download PDFInfo
- Publication number
- ES2575955T3 ES2575955T3 ES08847760.9T ES08847760T ES2575955T3 ES 2575955 T3 ES2575955 T3 ES 2575955T3 ES 08847760 T ES08847760 T ES 08847760T ES 2575955 T3 ES2575955 T3 ES 2575955T3
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- ES
- Spain
- Prior art keywords
- methyl
- alkyl
- dichlorophenyl
- triazol
- thiazol
- 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.)
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- 239000003112 inhibitor Substances 0.000 title claims description 17
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 230
- 150000003839 salts Chemical class 0.000 claims abstract description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 34
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 33
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 32
- 125000006413 ring segment Chemical group 0.000 claims abstract description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 30
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 29
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 29
- 229910052717 sulfur Chemical group 0.000 claims abstract description 29
- 239000011593 sulfur Chemical group 0.000 claims abstract description 29
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 25
- 150000002367 halogens Chemical class 0.000 claims abstract description 23
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- 239000001301 oxygen Chemical group 0.000 claims abstract description 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 137
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 73
- -1 - C3-6 cycloalkyl Chemical group 0.000 claims description 70
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 46
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
- 125000004429 atom Chemical group 0.000 claims description 30
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
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- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 15
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- QQLKPFYHNXBVMO-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-n-[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]-5-methyltriazole-4-carboxamide Chemical compound CC1=C(C(=O)NC=2SC=C(CCO)N=2)N=NN1CC1=CC=C(Cl)C(Cl)=C1 QQLKPFYHNXBVMO-UHFFFAOYSA-N 0.000 claims description 3
- WINCCXDLJSBINT-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-n-[4-(hydroxymethyl)pyridin-2-yl]-5-methyltriazole-4-carboxamide Chemical compound CC1=C(C(=O)NC=2N=CC=C(CO)C=2)N=NN1CC1=CC=C(Cl)C(Cl)=C1 WINCCXDLJSBINT-UHFFFAOYSA-N 0.000 claims description 3
- DRIKBOUXIULDLW-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-n-[5-(hydroxymethyl)-1,3,4-thiadiazol-2-yl]-5-methyltriazole-4-carboxamide Chemical compound CC1=C(C(=O)NC=2SC(CO)=NN=2)N=NN1CC1=CC=C(Cl)C(Cl)=C1 DRIKBOUXIULDLW-UHFFFAOYSA-N 0.000 claims description 3
- YYPKNBZUTIOOPB-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-n-[5-(hydroxymethyl)-1,3-thiazol-2-yl]-5-(methoxymethyl)triazole-4-carboxamide Chemical compound COCC1=C(C(=O)NC=2SC(CO)=CN=2)N=NN1CC1=CC=C(Cl)C(Cl)=C1 YYPKNBZUTIOOPB-UHFFFAOYSA-N 0.000 claims description 3
- HHNCYXDOOYAAEL-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-n-[5-(hydroxymethyl)-1,3-thiazol-2-yl]-5-methyltriazole-4-carboxamide Chemical compound CC1=C(C(=O)NC=2SC(CO)=CN=2)N=NN1CC1=CC=C(Cl)C(Cl)=C1 HHNCYXDOOYAAEL-UHFFFAOYSA-N 0.000 claims description 3
- STXJUEONAAWCQM-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-n-[5-(hydroxymethyl)-4-methyl-1,3-thiazol-2-yl]-5-methyltriazole-4-carboxamide Chemical compound S1C(CO)=C(C)N=C1NC(=O)C1=C(C)N(CC=2C=C(Cl)C(Cl)=CC=2)N=N1 STXJUEONAAWCQM-UHFFFAOYSA-N 0.000 claims description 3
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- PVRSXSGPJNWWDF-UHFFFAOYSA-N [2-[[1-[(3,4-dichlorophenyl)methyl]triazol-4-yl]methylamino]-1,3-thiazol-5-yl]methanol Chemical compound S1C(CO)=CN=C1NCC(N=N1)=CN1CC1=CC=C(Cl)C(Cl)=C1 PVRSXSGPJNWWDF-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/02—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 containing two hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
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- Child & Adolescent Psychology (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0722075 | 2007-11-09 | ||
| GBGB0722075.9A GB0722075D0 (en) | 2007-11-09 | 2007-11-09 | Compounds |
| PCT/EP2008/065105 WO2009060054A1 (en) | 2007-11-09 | 2008-11-07 | Triazole derivatives as scd inhibitors |
Publications (1)
| Publication Number | Publication Date |
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| ES2575955T3 true ES2575955T3 (es) | 2016-07-04 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08847760.9T Active ES2575955T3 (es) | 2007-11-09 | 2008-11-07 | Derivados de triazol como inhibidores de SCD |
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| Country | Link |
|---|---|
| US (2) | US8207204B2 (enExample) |
| EP (1) | EP2207774B1 (enExample) |
| JP (1) | JP5597542B2 (enExample) |
| ES (1) | ES2575955T3 (enExample) |
| GB (1) | GB0722075D0 (enExample) |
| WO (1) | WO2009060054A1 (enExample) |
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| GB0722075D0 (en) * | 2007-11-09 | 2007-12-19 | Smithkline Beecham Corp | Compounds |
| GB0722077D0 (en) | 2007-11-09 | 2007-12-19 | Smithkline Beecham Corp | Compounds |
| JP5748947B2 (ja) * | 2009-09-01 | 2015-07-15 | 公益財団法人相模中央化学研究所 | ２−アシルアミノチアゾール誘導体及びその製造方法 |
| WO2013134546A1 (en) | 2012-03-07 | 2013-09-12 | Mayo Foundation For Medical Education And Research | Methods and materials for treating cancer |
| CN102746853B (zh) * | 2012-06-18 | 2013-12-11 | 北京科技大学 | 一种三唑类弯曲棒状液晶化合物及其制备方法 |
| WO2014120994A1 (en) * | 2013-01-31 | 2014-08-07 | The Johns Hopkins University | Rufinamide and derivatives and their use in modulating the gating process of human voltage-gated sodium channels |
| GB201401886D0 (en) | 2014-02-04 | 2014-03-19 | Lytix Biopharma As | Neurodegenerative therapies |
| EP4180041A1 (en) | 2014-08-07 | 2023-05-17 | Mayo Foundation for Medical Education and Research | Compounds and methods for treating cancer |
| WO2016202935A1 (en) * | 2015-06-19 | 2016-12-22 | Bayer Pharma Aktiengesellschaft | Glucose transport inhibitors |
| US10294237B2 (en) | 2015-06-22 | 2019-05-21 | Sumitomo Dainippon Pharma Co., Ltd. | Bicyclic heterocyclic amide derivative |
| CA2990583A1 (en) * | 2015-06-22 | 2016-12-29 | Sumitomo Dainippon Pharma Co., Ltd. | 1,4-disubstituted imidazole derivative |
| JP6896701B2 (ja) | 2016-02-26 | 2021-06-30 | 大日本住友製薬株式会社 | イミダゾリルアミド誘導体 |
| MA46589A (fr) | 2016-10-24 | 2019-08-28 | Yumanity Therapeutics Inc | Composés et utilisations de ces derniers |
| KR20190108118A (ko) | 2017-01-06 | 2019-09-23 | 유마니티 테라퓨틱스, 인크. | 신경계 장애의 치료를 위한 방법 |
| US11873298B2 (en) | 2017-10-24 | 2024-01-16 | Janssen Pharmaceutica Nv | Compounds and uses thereof |
| KR20190110740A (ko) | 2018-03-21 | 2019-10-01 | 주식회사유한양행 | 신규의 아릴 또는 헤테로아릴 트라이아졸론 유도체 또는 이의 염 및 이를 포함하는 약학 조성물 |
| KR20190110736A (ko) * | 2018-03-21 | 2019-10-01 | 주식회사유한양행 | 신규의 트라이아졸론 유도체 또는 이의 염 및 이를 포함하는 약학 조성물 |
| MX2020009942A (es) | 2018-03-23 | 2021-01-08 | Yumanity Therapeutics Inc | Compuestos y usos de los mismos. |
| TWI835945B (zh) | 2018-12-14 | 2024-03-21 | 南韓商柳韓洋行股份有限公司 | 3,3-二氟烯丙胺化物或其鹽及包含彼的醫藥組合物 |
| TW202039486A (zh) | 2018-12-14 | 2020-11-01 | 南韓商柳韓洋行股份有限公司 | 三唑并吡啶-3-酮化物或其鹽及包含彼之醫藥組合物 |
| KR20220007845A (ko) | 2019-01-24 | 2022-01-19 | 유마니티 테라퓨틱스, 인크. | 화합물 및 이의 용도 |
| EA202192047A1 (ru) | 2019-11-13 | 2021-12-08 | Юманити Терапьютикс, Инк. | Соединения и их применение |
| GB202205846D0 (en) * | 2022-04-22 | 2022-06-08 | Phytoquest Ltd | Bioactive molecules in yogurt |
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| US20060160794A1 (en) * | 2003-06-12 | 2006-07-20 | Amegadzie Albert K | Tachykinin receptor antagonists |
| WO2006101521A2 (en) | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| DE102005019970B4 (de) | 2005-04-27 | 2007-04-26 | Phoenix Contact Gmbh & Co. Kg | Adressvergabe für sichere Busteilnehmer |
| WO2007009236A1 (en) * | 2005-07-20 | 2007-01-25 | Merck Frosst Canada Ltd. | Heteroaromatic compounds as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| GB0625605D0 (en) | 2006-12-21 | 2007-01-31 | Smithkline Beecham Corp | Compounds |
| GB0625654D0 (en) | 2006-12-21 | 2007-01-31 | Smithkline Beecham Corp | Compounds |
| GB0625594D0 (en) | 2006-12-21 | 2007-01-31 | Smithkline Beecham Corp | Compounds |
| GB0625604D0 (en) | 2006-12-21 | 2007-01-31 | Smithkline Beecham Corp | Compounds |
| EP2125799A1 (en) | 2007-02-28 | 2009-12-02 | Smithkline Beecham Corporation | Thiadiazole derivatives, inhibitors of stearoyl-coa desaturase |
| GB0714129D0 (en) | 2007-07-19 | 2007-08-29 | Smithkline Beecham Corp | compounds |
| GB0715055D0 (en) | 2007-08-02 | 2007-09-12 | Smithkline Beecham Corp | Compounds |
| GB0721419D0 (en) | 2007-10-31 | 2007-12-12 | Smithkline Beecham Corp | Compounds |
| GB0722077D0 (en) | 2007-11-09 | 2007-12-19 | Smithkline Beecham Corp | Compounds |
| GB0722075D0 (en) * | 2007-11-09 | 2007-12-19 | Smithkline Beecham Corp | Compounds |
| GB0810913D0 (en) | 2008-06-13 | 2008-07-23 | Smithkline Beecham Corp | Comppounds |
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- 2008-11-07 EP EP08847760.9A patent/EP2207774B1/en not_active Not-in-force
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| GB0722075D0 (en) | 2007-12-19 |
| JP5597542B2 (ja) | 2014-10-01 |
| US20120225878A1 (en) | 2012-09-06 |
| WO2009060054A1 (en) | 2009-05-14 |
| EP2207774B1 (en) | 2016-04-13 |
| US8207204B2 (en) | 2012-06-26 |
| JP2011503032A (ja) | 2011-01-27 |
| EP2207774A1 (en) | 2010-07-21 |
| US20100297097A1 (en) | 2010-11-25 |
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