JP2019537603A5 - - Google Patents
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- Publication number
- JP2019537603A5 JP2019537603A5 JP2019523847A JP2019523847A JP2019537603A5 JP 2019537603 A5 JP2019537603 A5 JP 2019537603A5 JP 2019523847 A JP2019523847 A JP 2019523847A JP 2019523847 A JP2019523847 A JP 2019523847A JP 2019537603 A5 JP2019537603 A5 JP 2019537603A5
- Authority
- JP
- Japan
- Prior art keywords
- tetrahydro
- pyrazole
- naphthylidine
- ethyl
- carboxyamide
- 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.)
- Granted
Links
- 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 277
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 157
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 147
- 235000019260 propionic acid Nutrition 0.000 claims 145
- -1 C (O) NR a R b Chemical compound 0.000 claims 126
- 125000000217 alkyl group Chemical group 0.000 claims 54
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 36
- 229940124530 sulfonamide Drugs 0.000 claims 32
- 150000003456 sulfonamides Chemical class 0.000 claims 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 30
- 125000001475 halogen functional group Chemical group 0.000 claims 27
- 125000003545 alkoxy group Chemical group 0.000 claims 26
- 125000004452 carbocyclyl group Chemical group 0.000 claims 26
- 125000003118 aryl group Chemical group 0.000 claims 24
- 125000001072 heteroaryl group Chemical group 0.000 claims 22
- 125000000623 heterocyclic group Chemical group 0.000 claims 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims 17
- 125000001188 haloalkyl group Chemical group 0.000 claims 17
- 125000004438 haloalkoxy group Chemical group 0.000 claims 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 15
- 150000001408 amides Chemical class 0.000 claims 14
- 125000004103 aminoalkyl group Chemical group 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 14
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- 206010016654 Fibrosis Diseases 0.000 claims 12
- 230000004761 fibrosis Effects 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 11
- 125000004404 heteroalkyl group Chemical group 0.000 claims 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 9
- 125000004429 atom Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 7
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 6
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 6
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims 4
- YECJUZIGFPJWGQ-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonamide Chemical compound CC1=CC(C)=C(S(N)(=O)=O)C(C)=C1 YECJUZIGFPJWGQ-UHFFFAOYSA-N 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 3
- 206010023421 Kidney fibrosis Diseases 0.000 claims 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 3
- 230000001476 alcoholic effect Effects 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 208000019425 cirrhosis of liver Diseases 0.000 claims 3
- 208000006454 hepatitis Diseases 0.000 claims 3
- 231100000283 hepatitis Toxicity 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 239000004475 Arginine Substances 0.000 claims 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 2
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- 201000009594 Systemic Scleroderma Diseases 0.000 claims 2
- 206010042953 Systemic sclerosis Diseases 0.000 claims 2
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000005884 carbocyclylalkyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 208000020832 chronic kidney disease Diseases 0.000 claims 2
- 125000004992 haloalkylamino group Chemical group 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- IWTFOFMTUOBLHG-UHFFFAOYSA-N 2-methoxypyridine Chemical compound COC1=CC=CC=N1 IWTFOFMTUOBLHG-UHFFFAOYSA-N 0.000 claims 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000005336 allyloxy group Chemical group 0.000 claims 1
- 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- OVIZSQRQYWEGON-UHFFFAOYSA-N butane-1-sulfonamide Chemical compound CCCCS(N)(=O)=O OVIZSQRQYWEGON-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- ICFQGMYPBURXAZ-UHFFFAOYSA-N pentane-1-sulfonamide Chemical compound CCCCCS(N)(=O)=O ICFQGMYPBURXAZ-UHFFFAOYSA-N 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662418838P | 2016-11-08 | 2016-11-08 | |
| US62/418,838 | 2016-11-08 | ||
| PCT/US2017/060390 WO2018089358A1 (en) | 2016-11-08 | 2017-11-07 | Azole amides and amines as alpha v integrin inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019537603A JP2019537603A (ja) | 2019-12-26 |
| JP2019537603A5 true JP2019537603A5 (enExample) | 2020-12-03 |
| JP7128811B2 JP7128811B2 (ja) | 2022-08-31 |
Family
ID=60409437
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019523847A Active JP7128811B2 (ja) | 2016-11-08 | 2017-11-07 | アルファｖインテグリン阻害剤としてのアゾールアミドおよびアミン |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US10851098B2 (enExample) |
| EP (1) | EP3538527B1 (enExample) |
| JP (1) | JP7128811B2 (enExample) |
| KR (1) | KR102510858B1 (enExample) |
| CN (1) | CN110167933B (enExample) |
| AU (1) | AU2017359028A1 (enExample) |
| BR (1) | BR112019009245A2 (enExample) |
| CA (1) | CA3042684A1 (enExample) |
| EA (1) | EA201991121A1 (enExample) |
| ES (1) | ES2898835T3 (enExample) |
| IL (1) | IL266465A (enExample) |
| MA (1) | MA46746A (enExample) |
| MX (1) | MX2019005234A (enExample) |
| WO (1) | WO2018089358A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109996541A (zh) | 2016-09-07 | 2019-07-09 | 普利安特治疗公司 | N-酰基氨基酸化合物及其使用方法 |
| KR20190100232A (ko) | 2016-12-29 | 2019-08-28 | 세인트 루이스 유니버시티 | 인테그린 길항제 |
| MA47697A (fr) | 2017-02-28 | 2020-01-08 | Morphic Therapeutic Inc | Inhibiteurs de l'(alpha-v)(bêta-6) intégrine |
| EP3589285A4 (en) | 2017-02-28 | 2020-08-12 | Morphic Therapeutic, Inc. | INHIBITORS OF INTEGRIN (ALPHA-V) (BETA-6) |
| EP3617206A1 (en) | 2018-08-29 | 2020-03-04 | Morphic Therapeutic, Inc. | Integrin inhibitors |
| KR102641718B1 (ko) | 2018-10-30 | 2024-02-29 | 길리애드 사이언시즈, 인코포레이티드 | 알파4베타7 인테그린 억제제로서의 이미다조피리딘 유도체 |
| CN112996786B (zh) | 2018-10-30 | 2024-08-20 | 吉利德科学公司 | 用于抑制α4β7整合素的化合物 |
| KR102659859B1 (ko) | 2018-10-30 | 2024-04-25 | 길리애드 사이언시즈, 인코포레이티드 | 알파4β7 인테그린의 억제를 위한 화합물 |
| US20220119383A1 (en) | 2018-10-30 | 2022-04-21 | Gilead Sciences, Inc. | Quinoline derivatives as alpha4beta7 integrin inhibitors |
| CN119431230A (zh) | 2019-08-14 | 2025-02-14 | 吉利德科学公司 | 用于抑制α4β7整合素的化合物 |
| GB202010626D0 (en) * | 2020-07-10 | 2020-08-26 | Univ Nottingham | Compound |
| WO2022167866A1 (en) * | 2021-02-08 | 2022-08-11 | Rappta Therapeutics Oy | Modulators of protein phosphatase 2a (pp2a) and methods using same |
| WO2022192545A1 (en) * | 2021-03-10 | 2022-09-15 | Dice Molecules Sv, Inc. | Alpha v beta 6 and alpha v beta 1 integrin inhibitors and uses thereof |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5849736A (en) * | 1993-11-24 | 1998-12-15 | The Dupont Merck Pharmaceutical Company | Isoxazoline and isoxazole fibrinogen receptor antagonists |
| ZA972195B (en) | 1996-03-15 | 1998-09-14 | Du Pont Merck Pharma | Spirocycle integrin inhibitors |
| JP2001524481A (ja) * | 1997-11-26 | 2001-12-04 | デュポン ファーマシューティカルズ カンパニー | αＶβ３アンタゴニストとしての１，３，４−チアジアゾール類および１，３，４−オキサジアゾール類 |
| AU736026B2 (en) | 1997-12-17 | 2001-07-26 | Merck & Co., Inc. | Integrin receptor antagonists |
| AU748621B2 (en) | 1998-08-13 | 2002-06-06 | Merck & Co., Inc. | Integrin receptor antagonists |
| AU749351B2 (en) * | 1999-06-02 | 2002-06-27 | Merck & Co., Inc. | Alpha V integrin receptor antagonists |
| AU2001269876A1 (en) * | 2000-06-15 | 2001-12-24 | Mark Laurence Boys | Heteroarylalkanoic acids as integrin receptor antagonists |
| MXPA03006772A (es) | 2001-01-29 | 2004-10-15 | Dimensional Pharm Inc | Indoles sustituidos y su uso como antogonistas de integrina. |
| PL219749B1 (pl) * | 2002-08-16 | 2015-07-31 | Janssen Pharmaceutica Nv | Pochodna piperydyny i jej zastosowanie oraz kompozycja farmaceutyczna ją zawierająca |
| US20070117849A1 (en) * | 2003-10-01 | 2007-05-24 | Simon Goodman | Alfavbeta3 and alfavbet6 integrin antagonists as antifibrotic agents |
| WO2006108040A1 (en) | 2005-04-05 | 2006-10-12 | Janssen Pharmaceutica, N.V. | Substituted indoles and their use as integrin antagonists |
| US20080045521A1 (en) | 2006-06-09 | 2008-02-21 | Astrazeneca Ab | Phenylalanine derivatives |
| WO2008125811A1 (en) | 2007-04-11 | 2008-10-23 | Astrazeneca Ab | N-[HETEROARYLCARBONYL]-S-THIENYL-L-ALANINE DERIVATIVES AS α5β1 ANTAGONISTS |
| ITFI20100019A1 (it) * | 2010-02-12 | 2011-08-13 | Univ Firenze | Inibitori peptidomimetici di integrine basati sull'1,2,3-triazolo per la diagnosi e terapia dei tumori. |
| JP2015535227A (ja) | 2012-10-26 | 2015-12-10 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | Ｓｙｋの３，４−二置換１ｈ−ピラゾール及び４，５−二置換チアゾール阻害剤 |
| ES2763556T3 (es) * | 2013-02-07 | 2020-05-29 | Scifluor Life Sciences Inc | Antagonistas fluorados de integrina |
| GB201305668D0 (en) | 2013-03-28 | 2013-05-15 | Glaxosmithkline Ip Dev Ltd | Avs6 Integrin Antagonists |
| TWI667233B (zh) | 2013-12-19 | 2019-08-01 | 德商拜耳製藥公司 | 新穎吲唑羧醯胺，其製備方法、含彼等之醫藥製劑及其製造醫藥之用途 |
| GB201417011D0 (en) | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| GB201417002D0 (en) | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compound |
| GB201417094D0 (en) | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| GB201417018D0 (en) | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| KR102647026B1 (ko) | 2015-02-19 | 2024-03-12 | 사이플루어 라이프 사이언시즈, 인크 | 플루오르화 테트라히드로나프티리디닐 노난산 유도체 및 이의 용도 |
| JP2018515424A (ja) | 2015-03-10 | 2018-06-14 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 抗アルファｖベータ１インテグリン阻害剤及び使用方法 |
| CA3042707A1 (en) * | 2016-11-08 | 2018-05-17 | Bristol-Myers Squibb Company | 3-substituted propionic acids as .alpha.v integrin inhibitors |
-
2017
- 2017-11-07 JP JP2019523847A patent/JP7128811B2/ja active Active
- 2017-11-07 ES ES17801235T patent/ES2898835T3/es active Active
- 2017-11-07 MA MA046746A patent/MA46746A/fr unknown
- 2017-11-07 EA EA201991121A patent/EA201991121A1/ru unknown
- 2017-11-07 AU AU2017359028A patent/AU2017359028A1/en not_active Abandoned
- 2017-11-07 CA CA3042684A patent/CA3042684A1/en not_active Abandoned
- 2017-11-07 KR KR1020197016076A patent/KR102510858B1/ko active Active
- 2017-11-07 BR BR112019009245A patent/BR112019009245A2/pt not_active Application Discontinuation
- 2017-11-07 WO PCT/US2017/060390 patent/WO2018089358A1/en not_active Ceased
- 2017-11-07 US US16/347,829 patent/US10851098B2/en active Active
- 2017-11-07 CN CN201780082144.8A patent/CN110167933B/zh active Active
- 2017-11-07 EP EP17801235.7A patent/EP3538527B1/en active Active
- 2017-11-07 MX MX2019005234A patent/MX2019005234A/es unknown
-
2019
- 2019-05-06 IL IL266465A patent/IL266465A/en unknown