JP5597542B2 - Ｓｃｄ阻害薬としてのトリアゾール誘導体 - Google Patents
Ｓｃｄ阻害薬としてのトリアゾール誘導体 Download PDFInfo
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- JP5597542B2 JP5597542B2 JP2010532599A JP2010532599A JP5597542B2 JP 5597542 B2 JP5597542 B2 JP 5597542B2 JP 2010532599 A JP2010532599 A JP 2010532599A JP 2010532599 A JP2010532599 A JP 2010532599A JP 5597542 B2 JP5597542 B2 JP 5597542B2
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- JP
- Japan
- Prior art keywords
- methyl
- alkyl
- dichlorophenyl
- triazole
- carboxamide
- 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.)
- Expired - Fee Related
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- 239000003112 inhibitor Substances 0.000 title description 11
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 228
- 150000001875 compounds Chemical class 0.000 claims description 203
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 66
- -1 5-[({1-[(3,4-Dichlorophenyl) methyl] -5-methyl-1H-1,2,3-triazol-4-yl} carbonyl) amino] -1,3,4-thiadiazole-2 -Ethyl carboxylate Chemical compound 0.000 claims description 52
- 125000006413 ring segment Chemical group 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 24
- 125000005842 heteroatom Chemical group 0.000 claims description 24
- 229910052717 sulfur Chemical group 0.000 claims description 24
- 239000011593 sulfur Chemical group 0.000 claims description 24
- 125000001188 haloalkyl group Chemical group 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000001301 oxygen Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000005973 Carvone Substances 0.000 claims description 6
- YJUUCBLNULZUSW-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-5-methyl-N-(4-methyl-1,3-thiazol-2-yl)triazole-4-carboxamide Chemical compound ClC=1C=C(C=CC=1Cl)CN1N=NC(=C1C)C(=O)NC=1SC=C(N=1)C YJUUCBLNULZUSW-UHFFFAOYSA-N 0.000 claims description 5
- DOBZBSPNHKOMIA-UHFFFAOYSA-N 2-[[1-[(3,4-dichlorophenyl)methyl]triazole-4-carbonyl]amino]-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)N)=CN=C1NC(=O)C(N=N1)=CN1CC1=CC=C(Cl)C(Cl)=C1 DOBZBSPNHKOMIA-UHFFFAOYSA-N 0.000 claims description 4
- IVIXDSIHYGSHJP-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-5-methyl-n-(1,3,4-thiadiazol-2-yl)triazole-4-carboxamide Chemical compound CC1=C(C(=O)NC=2SC=NN=2)N=NN1CC1=CC=C(Cl)C(Cl)=C1 IVIXDSIHYGSHJP-UHFFFAOYSA-N 0.000 claims description 3
- UXTIQTWACPISAD-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-n-(5-formyl-1,3-thiazol-2-yl)-5-methyltriazole-4-carboxamide Chemical compound CC1=C(C(=O)NC=2SC(C=O)=CN=2)N=NN1CC1=CC=C(Cl)C(Cl)=C1 UXTIQTWACPISAD-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
- XVFIROIXHGVGBJ-UHFFFAOYSA-N 2-[[1-[(3,4-dichlorophenyl)methyl]-5-methyltriazole-4-carbonyl]amino]-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(O)=O)=C(C)N=C1NC(=O)C1=C(C)N(CC=2C=C(Cl)C(Cl)=CC=2)N=N1 XVFIROIXHGVGBJ-UHFFFAOYSA-N 0.000 claims description 3
- GKQMHHZUWNIULG-UHFFFAOYSA-N 2-[[1-[(3,4-dichlorophenyl)methyl]-5-methyltriazole-4-carbonyl]amino]-n,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound CC1=C(C(=O)NC)SC(NC(=O)C2=C(N(CC=3C=C(Cl)C(Cl)=CC=3)N=N2)C)=N1 GKQMHHZUWNIULG-UHFFFAOYSA-N 0.000 claims description 3
- SQZLORQPHAJYBE-UHFFFAOYSA-N 2-[[1-[(3,4-dichlorophenyl)methyl]triazole-4-carbonyl]amino]-n-(2-hydroxyethyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NCCO)=CN=C1NC(=O)C(N=N1)=CN1CC1=CC=C(Cl)C(Cl)=C1 SQZLORQPHAJYBE-UHFFFAOYSA-N 0.000 claims description 3
- FSWLTVCGFNLBSC-UHFFFAOYSA-N N-(1,3-benzodioxol-5-yl)-1-[(4-fluorophenyl)methyl]-4-triazolecarboxamide Chemical compound C1=CC(F)=CC=C1CN1N=NC(C(=O)NC=2C=C3OCOC3=CC=2)=C1 FSWLTVCGFNLBSC-UHFFFAOYSA-N 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
- BBELFTARGYTHDL-UHFFFAOYSA-N n-(6-acetyl-1,3-benzodioxol-5-yl)-1-[(4-methylphenyl)methyl]triazole-4-carboxamide Chemical compound CC(=O)C1=CC=2OCOC=2C=C1NC(=O)C(N=N1)=CN1CC1=CC=C(C)C=C1 BBELFTARGYTHDL-UHFFFAOYSA-N 0.000 claims description 3
- KTWSYEZQTYYHCA-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-5-methyl-n-(5-methyl-1,3,4-oxadiazol-2-yl)triazole-4-carboxamide Chemical compound O1C(C)=NN=C1NC(=O)C1=C(C)N(CC=2C=C(Cl)C(Cl)=CC=2)N=N1 KTWSYEZQTYYHCA-UHFFFAOYSA-N 0.000 claims description 2
- HIYLWYNZTALBPF-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-5-methyl-n-[4-methyl-5-(4-methylpiperazine-1-carbonyl)-1,3-thiazol-2-yl]triazole-4-carboxamide Chemical compound C1CN(C)CCN1C(=O)C1=C(C)N=C(NC(=O)C2=C(N(CC=3C=C(Cl)C(Cl)=CC=3)N=N2)C)S1 HIYLWYNZTALBPF-UHFFFAOYSA-N 0.000 claims description 2
- CJCNHKVLKZKBRB-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-5-methyl-n-[4-methyl-5-(morpholine-4-carbonyl)-1,3-thiazol-2-yl]triazole-4-carboxamide Chemical compound S1C(C(=O)N2CCOCC2)=C(C)N=C1NC(=O)C(=C1C)N=NN1CC1=CC=C(Cl)C(Cl)=C1 CJCNHKVLKZKBRB-UHFFFAOYSA-N 0.000 claims description 2
- MJGOZLJSHPMVRG-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-n-(5,7-dioxo-4h-[1,3]thiazolo[4,5-d]pyrimidin-2-yl)-5-methyltriazole-4-carboxamide Chemical compound CC1=C(C(=O)NC=2SC=3C(=O)NC(=O)NC=3N=2)N=NN1CC1=CC=C(Cl)C(Cl)=C1 MJGOZLJSHPMVRG-UHFFFAOYSA-N 0.000 claims description 2
- ZPKFOWSICCGABP-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-n-(6-methoxy-1,3-benzothiazol-2-yl)-5-methyltriazole-4-carboxamide Chemical compound S1C2=CC(OC)=CC=C2N=C1NC(=O)C(=C1C)N=NN1CC1=CC=C(Cl)C(Cl)=C1 ZPKFOWSICCGABP-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 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 2
- RUQOQQPLJNBDLU-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-n-[5-(methoxymethyl)-1,3,4-thiadiazol-2-yl]-5-methyltriazole-4-carboxamide Chemical compound S1C(COC)=NN=C1NC(=O)C1=C(C)N(CC=2C=C(Cl)C(Cl)=CC=2)N=N1 RUQOQQPLJNBDLU-UHFFFAOYSA-N 0.000 claims description 2
- HMUBFKXBCBWGID-UHFFFAOYSA-N 2-[[1-[(3,4-dichlorophenyl)methyl]-5-methyltriazole-4-carbonyl]amino]-4-methyl-n-(3-methylbutyl)-1,3-thiazole-5-carboxamide Chemical compound CC1=C(C(=O)NCCC(C)C)SC(NC(=O)C2=C(N(CC=3C=C(Cl)C(Cl)=CC=3)N=N2)C)=N1 HMUBFKXBCBWGID-UHFFFAOYSA-N 0.000 claims description 2
- CSPDQCMMCLWQSU-UHFFFAOYSA-N 2-[[1-[(3,4-dichlorophenyl)methyl]-5-methyltriazole-4-carbonyl]amino]-4-methyl-n-propan-2-yl-1,3-thiazole-5-carboxamide Chemical compound CC1=C(C(=O)NC(C)C)SC(NC(=O)C2=C(N(CC=3C=C(Cl)C(Cl)=CC=3)N=N2)C)=N1 CSPDQCMMCLWQSU-UHFFFAOYSA-N 0.000 claims description 2
- UUQMIZGFESDJAL-UHFFFAOYSA-N 2-[[1-[(3,4-dichlorophenyl)methyl]-5-methyltriazole-4-carbonyl]amino]-n,n,4-trimethyl-1,3-thiazole-5-carboxamide Chemical compound CC1=C(C(=O)N(C)C)SC(NC(=O)C2=C(N(CC=3C=C(Cl)C(Cl)=CC=3)N=N2)C)=N1 UUQMIZGFESDJAL-UHFFFAOYSA-N 0.000 claims description 2
- BODRVDIVZMVGMT-UHFFFAOYSA-N 2-[[1-[(3,4-dichlorophenyl)methyl]-5-methyltriazole-4-carbonyl]amino]-n,n-dimethyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)N(C)C)=CN=C1NC(=O)C1=C(C)N(CC=2C=C(Cl)C(Cl)=CC=2)N=N1 BODRVDIVZMVGMT-UHFFFAOYSA-N 0.000 claims description 2
- PEXRZOMFOKNMSC-UHFFFAOYSA-N 2-[[1-[(3,4-dichlorophenyl)methyl]-5-methyltriazole-4-carbonyl]amino]-n-(2-hydroxyethyl)-1,3-thiazole-5-carboxamide Chemical compound CC1=C(C(=O)NC=2SC(=CN=2)C(=O)NCCO)N=NN1CC1=CC=C(Cl)C(Cl)=C1 PEXRZOMFOKNMSC-UHFFFAOYSA-N 0.000 claims description 2
- WJANGXSNWJYUOX-UHFFFAOYSA-N 2-[[1-[(3,4-dichlorophenyl)methyl]-5-methyltriazole-4-carbonyl]amino]-n-(2-hydroxyethyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NCCO)=C(C)N=C1NC(=O)C1=C(C)N(CC=2C=C(Cl)C(Cl)=CC=2)N=N1 WJANGXSNWJYUOX-UHFFFAOYSA-N 0.000 claims description 2
- OJKABWGGAYFPCH-UHFFFAOYSA-N 2-[[1-[(3,4-dichlorophenyl)methyl]-5-methyltriazole-4-carbonyl]amino]-n-(2-methoxyethyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC1=C(C(=O)NCCOC)SC(NC(=O)C2=C(N(CC=3C=C(Cl)C(Cl)=CC=3)N=N2)C)=N1 OJKABWGGAYFPCH-UHFFFAOYSA-N 0.000 claims description 2
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- FPYYDWOUJOIZGQ-UHFFFAOYSA-N 2-[[1-[(3,4-dichlorophenyl)methyl]-5-methyltriazole-4-carbonyl]amino]-n-[2-(dimethylamino)ethyl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC1=C(C(=O)NCCN(C)C)SC(NC(=O)C2=C(N(CC=3C=C(Cl)C(Cl)=CC=3)N=N2)C)=N1 FPYYDWOUJOIZGQ-UHFFFAOYSA-N 0.000 claims description 2
- CHTAGKMMUFSEBQ-UHFFFAOYSA-N 2-[[1-[(3,4-dichlorophenyl)methyl]-5-methyltriazole-4-carbonyl]amino]-n-ethyl-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC1=C(C(=O)NCC)SC(NC(=O)C2=C(N(CC=3C=C(Cl)C(Cl)=CC=3)N=N2)C)=N1 CHTAGKMMUFSEBQ-UHFFFAOYSA-N 0.000 claims description 2
- AUCGJOFNIPOTMB-UHFFFAOYSA-N 2-[[1-[(3,4-dichlorophenyl)methyl]-5-methyltriazole-4-carbonyl]amino]-n-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC)=CN=C1NC(=O)C1=C(C)N(CC=2C=C(Cl)C(Cl)=CC=2)N=N1 AUCGJOFNIPOTMB-UHFFFAOYSA-N 0.000 claims description 2
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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 2
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- C07D403/12—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 linked by a chain containing hetero atoms as chain links
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| PCT/EP2008/065105 WO2009060054A1 (en) | 2007-11-09 | 2008-11-07 | Triazole derivatives as scd inhibitors |
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| 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 |
| US10301273B2 (en) | 2014-08-07 | 2019-05-28 | 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 |
| WO2016208591A1 (ja) | 2015-06-22 | 2016-12-29 | 大日本住友製薬株式会社 | １，４－ジ置換イミダゾール誘導体 |
| EP3323809A4 (en) | 2015-06-22 | 2019-01-02 | Sumitomo Dainippon Pharma Co., Ltd. | Bicyclic heterocyclic amide 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 |
| MA47212A (fr) | 2017-01-06 | 2019-11-13 | Yumanity Therapeutics Inc | Méthodes de traitement de troubles neurologiques |
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| 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 |
| CN112312913B (zh) | 2018-03-23 | 2024-03-08 | 詹森药业有限公司 | 化合物和其用途 |
| 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 |
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| 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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| EP1804799B1 (en) | 2004-09-20 | 2013-08-21 | 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 |
| AU2006272334A1 (en) | 2005-07-20 | 2007-01-25 | Merck Frosst Canada Ltd | Heteroaromatic compounds as inhibitors of stearoyl-coenzyme A delta-9 desaturase |
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| JP2011503032A (ja) | 2011-01-27 |
| US20120225878A1 (en) | 2012-09-06 |
| GB0722075D0 (en) | 2007-12-19 |
| EP2207774A1 (en) | 2010-07-21 |
| EP2207774B1 (en) | 2016-04-13 |
| ES2575955T3 (es) | 2016-07-04 |
| US20100297097A1 (en) | 2010-11-25 |
| WO2009060054A1 (en) | 2009-05-14 |
| US8207204B2 (en) | 2012-06-26 |
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