JP2017516771A5 - - Google Patents
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- JP2017516771A5 JP2017516771A5 JP2016568635A JP2016568635A JP2017516771A5 JP 2017516771 A5 JP2017516771 A5 JP 2017516771A5 JP 2016568635 A JP2016568635 A JP 2016568635A JP 2016568635 A JP2016568635 A JP 2016568635A JP 2017516771 A5 JP2017516771 A5 JP 2017516771A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- unsubstituted
- cycloalkyl
- substituted
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 146
- 125000001424 substituent group Chemical group 0.000 claims 52
- 229910052736 halogen Inorganic materials 0.000 claims 46
- 150000002367 halogens Chemical class 0.000 claims 46
- 150000001875 compounds Chemical class 0.000 claims 38
- 229910052739 hydrogen Inorganic materials 0.000 claims 33
- 239000001257 hydrogen Substances 0.000 claims 33
- 150000003839 salts Chemical class 0.000 claims 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 13
- 229910052760 oxygen Inorganic materials 0.000 claims 13
- 239000001301 oxygen Substances 0.000 claims 13
- 150000001204 N-oxides Chemical class 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 239000011593 sulfur Substances 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 235000019000 fluorine Nutrition 0.000 claims 7
- 125000001153 fluoro group Chemical group F* 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000002619 bicyclic group Chemical group 0.000 claims 6
- 150000001721 carbon Chemical group 0.000 claims 6
- 239000003112 inhibitor Substances 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 4
- 239000003937 drug carrier Substances 0.000 claims 3
- 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 claims 2
- 102100026148 Free fatty acid receptor 1 Human genes 0.000 claims 2
- 101710142060 Free fatty acid receptor 1 Proteins 0.000 claims 2
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 claims 2
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims 2
- 102000004877 Insulin Human genes 0.000 claims 2
- 108090001061 Insulin Proteins 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- 102000002072 Non-Receptor Type 1 Protein Tyrosine Phosphatase Human genes 0.000 claims 2
- 108010015847 Non-Receptor Type 1 Protein Tyrosine Phosphatase Proteins 0.000 claims 2
- 102000023984 PPAR alpha Human genes 0.000 claims 2
- 230000008484 agonism Effects 0.000 claims 2
- 239000000556 agonist Substances 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229940125396 insulin Drugs 0.000 claims 2
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims 1
- MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 claims 1
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims 1
- 229940123208 Biguanide Drugs 0.000 claims 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims 1
- 101001078593 Caenorhabditis elegans 3beta-hydroxysteroid dehydrogenase/Delta(5)-Delta(4) isomerase 1 Proteins 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229940122502 Cholesterol absorption inhibitor Drugs 0.000 claims 1
- 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 claims 1
- 229940122904 Glucagon receptor antagonist Drugs 0.000 claims 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- 101000618112 Homo sapiens Sperm-associated antigen 8 Proteins 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 108010016731 PPAR gamma Proteins 0.000 claims 1
- 102000000536 PPAR gamma Human genes 0.000 claims 1
- 229940122054 Peroxisome proliferator-activated receptor delta agonist Drugs 0.000 claims 1
- 102100040918 Pro-glucagon Human genes 0.000 claims 1
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims 1
- 108091006277 SLC5A1 Proteins 0.000 claims 1
- 102000058090 Sodium-Glucose Transporter 1 Human genes 0.000 claims 1
- 229940123518 Sodium/glucose cotransporter 2 inhibitor Drugs 0.000 claims 1
- 102100021913 Sperm-associated antigen 8 Human genes 0.000 claims 1
- 102000001494 Sterol O-Acyltransferase Human genes 0.000 claims 1
- 108010054082 Sterol O-acyltransferase Proteins 0.000 claims 1
- 229940100389 Sulfonylurea Drugs 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 230000003579 anti-obesity Effects 0.000 claims 1
- 239000003613 bile acid Substances 0.000 claims 1
- 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 claims 1
- 229940125881 cholesteryl ester transfer protein inhibitor Drugs 0.000 claims 1
- 229940125542 dual agonist Drugs 0.000 claims 1
- OLNTVTPDXPETLC-XPWALMASSA-N ezetimibe Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(O)=CC=1)C1=CC=C(F)C=C1 OLNTVTPDXPETLC-XPWALMASSA-N 0.000 claims 1
- 229960000815 ezetimibe Drugs 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
- 229940121380 ileal bile acid transporter inhibitor Drugs 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 229960004738 nicotinyl alcohol Drugs 0.000 claims 1
- 239000004031 partial agonist Substances 0.000 claims 1
- 239000002530 phenolic antioxidant Substances 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- 229960002855 simvastatin Drugs 0.000 claims 1
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 claims 1
- MFFMDFFZMYYVKS-SECBINFHSA-N sitagliptin Chemical compound C([C@H](CC(=O)N1CC=2N(C(=NN=2)C(F)(F)F)CC1)N)C1=CC(F)=C(F)C=C1F MFFMDFFZMYYVKS-SECBINFHSA-N 0.000 claims 1
- 229960004034 sitagliptin Drugs 0.000 claims 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNPCT/CN2014/078104 | 2014-05-22 | ||
| PCT/CN2014/078104 WO2015176267A1 (en) | 2014-05-22 | 2014-05-22 | Antidiabetic tricyclic compounds |
| PCT/CN2015/079262 WO2015176640A1 (en) | 2014-05-22 | 2015-05-19 | Antidiabetic tricyclic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2017516771A JP2017516771A (ja) | 2017-06-22 |
| JP2017516771A5 true JP2017516771A5 (https=) | 2018-06-07 |
Family
ID=54553222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016568635A Pending JP2017516771A (ja) | 2014-05-22 | 2015-05-19 | 抗糖尿病性三環式化合物 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US10000454B2 (https=) |
| EP (1) | EP3145915B1 (https=) |
| JP (1) | JP2017516771A (https=) |
| KR (1) | KR20170005861A (https=) |
| CN (1) | CN106458913A (https=) |
| AU (1) | AU2015263620B2 (https=) |
| CA (1) | CA2947781A1 (https=) |
| ES (1) | ES3016636T3 (https=) |
| MX (1) | MX2016015182A (https=) |
| RU (1) | RU2016150413A (https=) |
| WO (2) | WO2015176267A1 (https=) |
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| KR102435080B1 (ko) | 2016-07-19 | 2022-08-22 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 해충 방제제로서의 축합 바이시클릭 헤테로사이클 유도체 |
| CN106588673B (zh) * | 2016-12-20 | 2018-06-26 | 金凯(辽宁)化工有限公司 | 一种2-甲基-5-氨基三氟甲苯的制备方法 |
| BR102018007822A2 (pt) | 2017-04-20 | 2018-11-06 | Gilead Sciences, Inc. | composto, métodos para inibir pd-1, pd-l1 e/ou interação de pd-1/pd-l1 e para tratamento de câncer, composição farmacêutica, e, kit para tratamento de ou prevenção de câncer ou uma doença ou condição |
| AU2018331125A1 (en) | 2017-09-12 | 2020-03-05 | Jiangsu Hengrui Medicine Co., Ltd. | Deuterium atom-substituted indole formamide derivative, preparation method therefor, and medical applications thereof |
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| KR102591947B1 (ko) | 2018-04-19 | 2023-10-25 | 길리애드 사이언시즈, 인코포레이티드 | Pd-1/pd-l1 억제제 |
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| CN112574122B (zh) * | 2019-09-27 | 2024-05-31 | 上海天慈国际药业有限公司 | 一种奥拉帕尼关键中间体的制备方法 |
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-
2014
- 2014-05-22 WO PCT/CN2014/078104 patent/WO2015176267A1/en not_active Ceased
-
2015
- 2015-05-19 KR KR1020167035452A patent/KR20170005861A/ko not_active Withdrawn
- 2015-05-19 JP JP2016568635A patent/JP2017516771A/ja active Pending
- 2015-05-19 EP EP15795833.1A patent/EP3145915B1/en active Active
- 2015-05-19 CN CN201580026394.0A patent/CN106458913A/zh active Pending
- 2015-05-19 WO PCT/CN2015/079262 patent/WO2015176640A1/en not_active Ceased
- 2015-05-19 ES ES15795833T patent/ES3016636T3/es active Active
- 2015-05-19 RU RU2016150413A patent/RU2016150413A/ru not_active Application Discontinuation
- 2015-05-19 AU AU2015263620A patent/AU2015263620B2/en not_active Ceased
- 2015-05-19 CA CA2947781A patent/CA2947781A1/en not_active Abandoned
- 2015-05-19 MX MX2016015182A patent/MX2016015182A/es unknown
- 2015-05-19 US US15/310,488 patent/US10000454B2/en active Active
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