JP2019537594A5 - - Google Patents
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- Publication number
- JP2019537594A5 JP2019537594A5 JP2019523576A JP2019523576A JP2019537594A5 JP 2019537594 A5 JP2019537594 A5 JP 2019537594A5 JP 2019523576 A JP2019523576 A JP 2019523576A JP 2019523576 A JP2019523576 A JP 2019523576A JP 2019537594 A5 JP2019537594 A5 JP 2019537594A5
- Authority
- JP
- Japan
- Prior art keywords
- tetrahydro
- naphthylidine
- propanoic acid
- propyl
- pyrazole
- 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
- -1 cyano, nitro, amino Chemical group 0.000 claims 216
- 235000019260 propionic acid Nutrition 0.000 claims 177
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 137
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 103
- 150000004672 propanoic acids Chemical compound 0.000 claims 78
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 38
- 125000000217 alkyl group Chemical group 0.000 claims 29
- 125000004452 carbocyclyl group Chemical group 0.000 claims 22
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000005843 halogen group Chemical group 0.000 claims 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 16
- 206010016654 Fibrosis Diseases 0.000 claims 15
- 230000004761 fibrosis Effects 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 125000001188 haloalkyl group Chemical group 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- 239000011780 sodium chloride Substances 0.000 claims 13
- 125000004103 aminoalkyl group Chemical group 0.000 claims 12
- 125000004438 haloalkoxy group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims 11
- 229960001663 sulfanilamide Drugs 0.000 claims 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 9
- KXDHJXZQYSOELW-UHFFFAOYSA-M carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 8
- 150000001408 amides Chemical class 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 201000009794 idiopathic pulmonary fibrosis Diseases 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims 4
- 125000003762 3,4-dimethoxyphenyl group Chemical compound [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 4
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 4
- 125000005418 aryl aryl group Chemical group 0.000 claims 4
- 125000004429 atoms Chemical group 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 210000004185 Liver Anatomy 0.000 claims 3
- 208000005069 Pulmonary Fibrosis Diseases 0.000 claims 3
- 230000001476 alcoholic Effects 0.000 claims 3
- 230000000747 cardiac effect Effects 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 201000002793 renal fibrosis Diseases 0.000 claims 3
- 231100000240 steatosis hepatitis Toxicity 0.000 claims 3
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 239000004475 Arginine Substances 0.000 claims 2
- 206010061835 Diabetic nephropathy Diseases 0.000 claims 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 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
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- 125000005884 carbocyclylalkyl group Chemical group 0.000 claims 2
- 201000000522 chronic kidney disease Diseases 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000005842 heteroatoms Chemical group 0.000 claims 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 2
- 201000009594 systemic scleroderma Diseases 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims 1
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000006414 CCl Chemical group ClC* 0.000 claims 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N Isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N Isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N Thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000000511 arginine group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drugs Drugs 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N furane Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- XPXMKIXDFWLRAA-UHFFFAOYSA-N hydrazinide Chemical compound [NH-]N XPXMKIXDFWLRAA-UHFFFAOYSA-N 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- KAESVJOAVNADME-UHFFFAOYSA-N pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662418848P | 2016-11-08 | 2016-11-08 | |
| US62/418,848 | 2016-11-08 | ||
| PCT/US2017/060376 WO2018089353A1 (en) | 2016-11-08 | 2017-11-07 | 3-substituted propionic acids as alpha v integrin inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019537594A JP2019537594A (ja) | 2019-12-26 |
| JP2019537594A5 true JP2019537594A5 (US07794700-20100914-C00152.png) | 2020-11-26 |
| JP7097358B2 JP7097358B2 (ja) | 2022-07-07 |
Family
ID=60409432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019523576A Active JP7097358B2 (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３－置換プロピオン酸 |
Country Status (28)
Families Citing this family (15)
| 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 |
| EA038164B1 (ru) * | 2016-11-08 | 2021-07-16 | Бристол-Маерс Сквибб Компани | 3-замещенные пропановые кислоты в качестве ингибиторов интегрина v |
| WO2018089355A1 (en) * | 2016-11-08 | 2018-05-17 | Bristol-Myers Squibb Company | Cyclobutane- and azetidine-containing mono and spirocyclic compounds as alpha v integrin inhibitors |
| WO2018089358A1 (en) * | 2016-11-08 | 2018-05-17 | Bristol-Myers Squibb Company | Azole amides and amines as alpha v integrin inhibitors |
| KR20190100232A (ko) | 2016-12-29 | 2019-08-28 | 세인트 루이스 유니버시티 | 인테그린 길항제 |
| EP4147698A1 (en) | 2017-02-28 | 2023-03-15 | Morphic Therapeutic, Inc. | Inhibitors of (alpha-v)(beta-6) integrin |
| JP7092784B2 (ja) | 2017-02-28 | 2022-06-28 | モーフィック セラピューティック，インコーポレイテッド | αｖβ６インテグリン阻害剤 |
| JP2021535141A (ja) | 2018-08-29 | 2021-12-16 | モーフィック セラピューティック，インコーポレイテッド | αｖβ６インテグリンの阻害 |
| AU2019373242B2 (en) | 2018-10-30 | 2023-07-13 | Gilead Sciences, Inc. | Compounds for inhibition of alpha 4 beta 7 integrin |
| CN112969504B (zh) | 2018-10-30 | 2024-04-09 | 吉利德科学公司 | 用于抑制α4β7整合素的化合物 |
| AU2019373240B2 (en) | 2018-10-30 | 2023-04-20 | Gilead Sciences, Inc. | Quinoline derivatives as alpha4beta7 integrin inhibitors |
| KR102641718B1 (ko) | 2018-10-30 | 2024-02-29 | 길리애드 사이언시즈, 인코포레이티드 | 알파4베타7 인테그린 억제제로서의 이미다조피리딘 유도체 |
| CN109824495B (zh) * | 2019-02-02 | 2022-12-09 | 盐城师范学院 | 一种新型偶联反应在制备碳-碳键结构化合物中的应用 |
| WO2021030438A1 (en) | 2019-08-14 | 2021-02-18 | Gilead Sciences, Inc. | Compounds for inhibition of alpha 4 beta 7 integrin |
| GB202010626D0 (en) | 2020-07-10 | 2020-08-26 | Univ Nottingham | Compound |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP0451790A1 (de) * | 1990-04-12 | 1991-10-16 | Hoechst Aktiengesellschaft | 3,5-disubstituierte 2-Isoxazoline und Isoxazole, Verfahren zu deren Herstellung, diese enthaltende Mittel und ihre Verwendung |
| 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 |
| EP1049693A1 (en) | 1997-11-26 | 2000-11-08 | Du Pont Pharmaceuticals Company | 1,3,4-THIADIAZOLES AND 1,3,4-OXADIAZOLES AS $g(a) v?$g(b) 3? ANTAGONISTS |
| EP1047425A4 (en) * | 1997-12-17 | 2009-04-22 | Merck & Co Inc | INTEGRIN RECEPTOR ANTAGONISTS |
| EP1105389A4 (en) | 1998-08-13 | 2001-10-17 | Merck & Co Inc | INTEGRIN RECEPTOR ANTAGONISTS |
| ES2376161T3 (es) | 2001-01-29 | 2012-03-09 | Janssen Pharmaceuticals, Inc. | Indoles sustituidos y su utilización como antagonistas de integrinas. |
| WO2004058761A1 (en) * | 2002-12-20 | 2004-07-15 | Pharmacia Corporation | Pyrazole compounds as integrin receptor antagonists derivatives |
| BR0317600A (pt) * | 2002-12-20 | 2005-11-29 | Pharmacia Corp | ácidos heteroarilalcanóicos como derivados de antagonistas de receptor de integrina |
| WO2006108040A1 (en) | 2005-04-05 | 2006-10-12 | Janssen Pharmaceutica, N.V. | Substituted indoles and their use as integrin antagonists |
| TW200800999A (en) * | 2005-09-06 | 2008-01-01 | Astrazeneca Ab | Novel compounds |
| US7592461B2 (en) | 2005-12-21 | 2009-09-22 | Bristol-Myers Squibb Company | Indane modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof |
| AR059224A1 (es) | 2006-01-31 | 2008-03-19 | Jerini Ag | Compuestos para la inhibicion de integrinas y uso de estas |
| WO2007141473A1 (en) | 2006-06-09 | 2007-12-13 | Astrazeneca Ab | N-(benzoyl)-o- [2- (pyridin- 2 -ylamino) ethyl] -l-tyrosine derivatives and related compounds as a5b1 antagonists for the treatment of solid tumors |
| WO2008125811A1 (en) * | 2007-04-11 | 2008-10-23 | Astrazeneca Ab | N-[HETEROARYLCARBONYL]-S-THIENYL-L-ALANINE DERIVATIVES AS α5β1 ANTAGONISTS |
| WO2011026937A1 (en) | 2009-09-04 | 2011-03-10 | Basf Se | Process for preparing 1-phenylpyrazoles |
| WO2011059839A1 (en) | 2009-10-29 | 2011-05-19 | Sirtris Pharmaceuticals, Inc. | Bicyclic pyridines and analogs as sirtuin modulators |
| 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. |
| 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 |
| GB201417018D0 (en) | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| GB201417094D0 (en) | 2014-09-26 | 2014-11-12 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| TWI736529B (zh) | 2015-02-19 | 2021-08-21 | 美商賽氟洛生命科學公司 | 氟化之四氫啶基壬酸衍生物及其用途 |
| 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 |
| EA038164B1 (ru) * | 2016-11-08 | 2021-07-16 | Бристол-Маерс Сквибб Компани | 3-замещенные пропановые кислоты в качестве ингибиторов интегрина v |
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2017
- 2017-11-07 EA EA201991122A patent/EA038164B1/ru unknown
- 2017-11-07 WO PCT/US2017/060376 patent/WO2018089353A1/en unknown
- 2017-11-07 MA MA046743A patent/MA46743A/fr unknown
- 2017-11-07 MX MX2019005244A patent/MX2019005244A/es unknown
- 2017-11-07 ES ES17801230T patent/ES2925173T3/es active Active
- 2017-11-07 AU AU2017359023A patent/AU2017359023B2/en active Active
- 2017-11-07 DK DK17801230.8T patent/DK3538525T3/da active
- 2017-11-07 LT LTEPPCT/US2017/060376T patent/LT3538525T/lt unknown
- 2017-11-07 HU HUE17801230A patent/HUE059708T2/hu unknown
- 2017-11-07 PE PE2019000940A patent/PE20191647A1/es unknown
- 2017-11-07 RS RS20220759A patent/RS63483B1/sr unknown
- 2017-11-07 KR KR1020197016082A patent/KR102505629B1/ko active IP Right Grant
- 2017-11-07 PL PL17801230.8T patent/PL3538525T3/pl unknown
- 2017-11-07 CN CN201780082473.2A patent/CN110167935B/zh active Active
- 2017-11-07 MY MYPI2019002576A patent/MY199931A/en unknown
- 2017-11-07 JP JP2019523576A patent/JP7097358B2/ja active Active
- 2017-11-07 SI SI201731195T patent/SI3538525T1/sl unknown
- 2017-11-07 US US16/347,844 patent/US10968219B2/en active Active
- 2017-11-07 HR HRP20220990TT patent/HRP20220990T1/hr unknown
- 2017-11-07 CA CA3042707A patent/CA3042707A1/en active Pending
- 2017-11-07 EP EP17801230.8A patent/EP3538525B1/en active Active
- 2017-11-07 PT PT178012308T patent/PT3538525T/pt unknown
- 2017-11-08 TW TW106138533A patent/TWI763733B/zh active
- 2017-11-08 AR ARP170103105A patent/AR110153A1/es unknown
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2019
- 2019-05-06 IL IL266473A patent/IL266473B/en unknown
- 2019-05-08 CL CL2019001264A patent/CL2019001264A1/es unknown
- 2019-06-04 CO CONC2019/0005824A patent/CO2019005824A2/es unknown
- 2019-06-07 ZA ZA2019/03665A patent/ZA201903665B/en unknown
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2021
- 2021-02-24 US US17/184,179 patent/US11884661B2/en active Active
