JP2020532550A5 - - Google Patents
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- Publication number
- JP2020532550A5 JP2020532550A5 JP2020512678A JP2020512678A JP2020532550A5 JP 2020532550 A5 JP2020532550 A5 JP 2020532550A5 JP 2020512678 A JP2020512678 A JP 2020512678A JP 2020512678 A JP2020512678 A JP 2020512678A JP 2020532550 A5 JP2020532550 A5 JP 2020532550A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- amino
- pyridyl
- 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
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- -1 2-Hydroxypropa-2-yl Chemical group 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 33
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 9
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000006002 1,1-difluoroethyl group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- QULQVCSHCACLOQ-UHFFFAOYSA-N 1-[4-[6-[1-methyl-5-[(6-propan-2-ylpyrazin-2-yl)amino]pyrazol-4-yl]pyridin-3-yl]phenyl]cyclopropane-1-carboxylic acid Chemical compound C(C)(C)C1=CN=CC(=N1)NC1=C(C=NN1C)C1=CC=C(C=N1)C1=CC=C(C=C1)C1(CC1)C(=O)O QULQVCSHCACLOQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims description 6
- 206010016654 Fibrosis Diseases 0.000 claims description 5
- 230000004761 fibrosis Effects 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 4
- IZIGBCMMMQBBNV-UHFFFAOYSA-N 1-[4-[4-[1-methyl-5-[(6-propan-2-ylpyrazin-2-yl)amino]pyrazol-4-yl]phenyl]phenyl]cyclopropane-1-carboxylic acid Chemical compound C(C)(C)C1=CN=CC(=N1)NC1=C(C=NN1C)C1=CC=C(C=C1)C1=CC=C(C=C1)C1(CC1)C(=O)O IZIGBCMMMQBBNV-UHFFFAOYSA-N 0.000 claims description 3
- KOIJODABUPRJDS-UHFFFAOYSA-N 1-[2-cyano-4-[6-[5-[(6-cyclopropyloxypyrazin-2-yl)amino]-1-methylpyrazol-4-yl]pyridin-3-yl]phenyl]cyclopropane-1-carboxylic acid Chemical compound C(#N)C1=C(C=CC(=C1)C=1C=NC(=CC=1)C=1C=NN(C=1NC1=NC(=CN=C1)OC1CC1)C)C1(CC1)C(=O)O KOIJODABUPRJDS-UHFFFAOYSA-N 0.000 claims description 2
- XGGYBDMIXLZPFU-UHFFFAOYSA-N 1-[3-(cyanomethyl)-4-[6-[1-methyl-5-[(6-propan-2-ylpyrazin-2-yl)amino]pyrazol-4-yl]pyridin-3-yl]phenyl]cyclopropane-1-carboxylic acid Chemical compound C(#N)CC=1C=C(C=CC=1C=1C=NC(=CC=1)C=1C=NN(C=1NC1=NC(=CN=C1)C(C)C)C)C1(CC1)C(=O)O XGGYBDMIXLZPFU-UHFFFAOYSA-N 0.000 claims description 2
- NSXWARPCWAPPIT-UHFFFAOYSA-N 1-[3-(methoxymethyl)-4-[6-[1-methyl-5-[(6-propan-2-ylpyrazin-2-yl)amino]pyrazol-4-yl]pyridin-3-yl]phenyl]cyclopropane-1-carboxylic acid Chemical compound C(C)(C)C1=CN=CC(=N1)NC1=C(C=NN1C)C1=CC=C(C=N1)C1=C(C=C(C=C1)C1(CC1)C(=O)O)COC NSXWARPCWAPPIT-UHFFFAOYSA-N 0.000 claims description 2
- WZMVKHVVKDAQPS-UHFFFAOYSA-N 1-[3-cyano-4-[6-[1-methyl-5-[(6-propan-2-ylpyrazin-2-yl)amino]pyrazol-4-yl]pyridin-3-yl]phenyl]cyclopropane-1-carboxylic acid Chemical compound C(#N)C=1C=C(C=CC=1C=1C=NC(=CC=1)C=1C=NN(C=1NC1=NC(=CN=C1)C(C)C)C)C1(CC1)C(=O)O WZMVKHVVKDAQPS-UHFFFAOYSA-N 0.000 claims description 2
- LLZJBRCDXQKHNK-UHFFFAOYSA-N 1-[4-[2-[1-methyl-5-[(6-propan-2-ylpyrazin-2-yl)amino]pyrazol-4-yl]pyrimidin-5-yl]phenyl]cyclopropane-1-carboxylic acid Chemical compound C(C)(C)C1=CN=CC(=N1)NC1=C(C=NN1C)C1=NC=C(C=N1)C1=CC=C(C=C1)C1(CC1)C(=O)O LLZJBRCDXQKHNK-UHFFFAOYSA-N 0.000 claims description 2
- YWVCNVGNWLTRMD-UHFFFAOYSA-N 1-[4-[4-[1-methyl-5-[[6-(2-methylpropyl)pyrazin-2-yl]amino]pyrazol-4-yl]phenyl]phenyl]cyclopropane-1-carboxylic acid Chemical compound C(C(C)C)C1=CN=CC(=N1)NC1=C(C=NN1C)C1=CC=C(C=C1)C1=CC=C(C=C1)C1(CC1)C(=O)O YWVCNVGNWLTRMD-UHFFFAOYSA-N 0.000 claims description 2
- PTNUTYVOMANMRW-UHFFFAOYSA-N 1-[4-[5-[1-methyl-5-[(6-propan-2-ylpyrazin-2-yl)amino]pyrazol-4-yl]pyrazin-2-yl]phenyl]cyclopropane-1-carboxylic acid Chemical compound C(C)(C)C1=CN=CC(=N1)NC1=C(C=NN1C)C=1N=CC(=NC=1)C1=CC=C(C=C1)C1(CC1)C(=O)O PTNUTYVOMANMRW-UHFFFAOYSA-N 0.000 claims description 2
- ZNPWHDPODRSYQC-UHFFFAOYSA-N 1-[4-[5-fluoro-6-[1-methyl-5-[(6-propan-2-yloxypyrazin-2-yl)amino]pyrazol-4-yl]pyridin-3-yl]phenyl]cyclopropane-1-carboxylic acid Chemical compound FC=1C=C(C=NC=1C=1C=NN(C=1NC1=NC(=CN=C1)OC(C)C)C)C1=CC=C(C=C1)C1(CC1)C(=O)O ZNPWHDPODRSYQC-UHFFFAOYSA-N 0.000 claims description 2
- VTJPSPQBNJNSKO-UHFFFAOYSA-N 1-[4-[6-[1-methyl-5-[(6-propan-2-yloxypyrazin-2-yl)amino]pyrazol-4-yl]pyridin-3-yl]phenyl]cyclopropane-1-carboxylic acid Chemical compound C(C)(C)OC1=CN=CC(=N1)NC1=C(C=NN1C)C1=CC=C(C=N1)C1=CC=C(C=C1)C1(CC1)C(=O)O VTJPSPQBNJNSKO-UHFFFAOYSA-N 0.000 claims description 2
- AWHHYOMHUXGWEM-UHFFFAOYSA-N 1-[4-[6-[1-methyl-5-[[6-(trifluoromethyl)pyrazin-2-yl]amino]pyrazol-4-yl]pyridin-3-yl]phenyl]cyclopropane-1-carboxylic acid Chemical compound CN1N=CC(=C1NC1=NC(=CN=C1)C(F)(F)F)C1=CC=C(C=N1)C1=CC=C(C=C1)C1(CC1)C(=O)O AWHHYOMHUXGWEM-UHFFFAOYSA-N 0.000 claims description 2
- LGXMMPNFLWGPJD-UHFFFAOYSA-N 1-[4-[6-[5-[(6-cyclopropyloxypyrazin-2-yl)amino]-1-methylpyrazol-4-yl]pyridin-3-yl]phenyl]cyclopropane-1-carboxylic acid Chemical compound C1(CC1)OC1=CN=CC(=N1)NC1=C(C=NN1C)C1=CC=C(C=N1)C1=CC=C(C=C1)C1(CC1)C(=O)O LGXMMPNFLWGPJD-UHFFFAOYSA-N 0.000 claims description 2
- HMHGLQULECVPPS-UHFFFAOYSA-N 1-[4-[6-[5-[[6-(1,1-difluoroethyl)pyrazin-2-yl]amino]-1-methylpyrazol-4-yl]pyridin-3-yl]phenyl]cyclopropane-1-carboxylic acid Chemical compound FC(C)(F)C1=CN=CC(=N1)NC1=C(C=NN1C)C1=CC=C(C=N1)C1=CC=C(C=C1)C1(CC1)C(=O)O HMHGLQULECVPPS-UHFFFAOYSA-N 0.000 claims description 2
- SWATWOUWJLKSFA-UHFFFAOYSA-N 1-[4-[6-[5-[[6-(2-fluoropropan-2-yl)pyrazin-2-yl]amino]-1-methylpyrazol-4-yl]pyridin-3-yl]phenyl]cyclopropane-1-carboxylic acid Chemical compound FC(C)(C)C1=CN=CC(=N1)NC1=C(C=NN1C)C1=CC=C(C=N1)C1=CC=C(C=C1)C1(CC1)C(=O)O SWATWOUWJLKSFA-UHFFFAOYSA-N 0.000 claims description 2
- AHENRFMTHLGPPL-UHFFFAOYSA-N 1-[6-[6-[1-methyl-5-[(6-propan-2-ylpyrazin-2-yl)amino]pyrazol-4-yl]pyridin-3-yl]pyridin-3-yl]cyclopropane-1-carboxylic acid Chemical compound C(C)(C)C1=CN=CC(=N1)NC1=C(C=NN1C)C1=CC=C(C=N1)C1=CC=C(C=N1)C1(CC1)C(=O)O AHENRFMTHLGPPL-UHFFFAOYSA-N 0.000 claims description 2
- RDHJKFCYDGUKLJ-UHFFFAOYSA-N C(C)(C)C1=CN=CC(=N1)NC1=C(C=NN1C)C1=CC=C(C=N1)C=1C=CC(=NC=1)C1(CC1)C(=O)O Chemical compound C(C)(C)C1=CN=CC(=N1)NC1=C(C=NN1C)C1=CC=C(C=N1)C=1C=CC(=NC=1)C1(CC1)C(=O)O RDHJKFCYDGUKLJ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- MQVZSCBXICVWNS-UHFFFAOYSA-N azane [4-[4-[5-[(6-cyclopropylpyrazin-2-yl)amino]-1-methylpyrazol-4-yl]phenyl]phenyl] cyclopropanecarboxylate Chemical compound N.Cn1ncc(c1Nc1cncc(n1)C1CC1)-c1ccc(cc1)-c1ccc(OC(=O)C2CC2)cc1 MQVZSCBXICVWNS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- OTDDJDZGEPULTG-UHFFFAOYSA-N 1-[3-methyl-4-[6-[1-methyl-5-[(6-propan-2-ylpyrazin-2-yl)amino]pyrazol-4-yl]pyridin-3-yl]phenyl]cyclopropane-1-carboxylic acid Chemical compound C(C)(C)C1=CN=CC(=N1)NC1=C(C=NN1C)C1=CC=C(C=N1)C1=C(C=C(C=C1)C1(CC1)C(=O)O)C OTDDJDZGEPULTG-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 3
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNPCT/CN2017/100354 | 2017-09-04 | ||
| PCT/CN2017/100354 WO2019041340A1 (en) | 2017-09-04 | 2017-09-04 | LYSOPHOSPHATIDE ACID RECEPTOR 1 RECEPTOR INHIBITORS (LPAR1) |
| PCT/US2018/048249 WO2019046239A1 (en) | 2017-09-04 | 2018-08-28 | LYSOPHOSPHATIDE ACID RECEPTOR 1 RECEPTOR INHIBITORS (LPAR1) |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020532550A JP2020532550A (ja) | 2020-11-12 |
| JP2020532550A5 true JP2020532550A5 (enExample) | 2020-12-24 |
| JP6854386B2 JP6854386B2 (ja) | 2021-04-07 |
Family
ID=63528947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020512678A Active JP6854386B2 (ja) | 2017-09-04 | 2018-08-28 | リゾホスファチジン酸受容体１（ｌｐａｒ１）阻害剤化合物 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US11365185B2 (enExample) |
| EP (1) | EP3679032B1 (enExample) |
| JP (1) | JP6854386B2 (enExample) |
| KR (1) | KR102341064B1 (enExample) |
| CN (1) | CN111032647B (enExample) |
| AU (1) | AU2018323969B2 (enExample) |
| CA (1) | CA3073983C (enExample) |
| EA (1) | EA039482B1 (enExample) |
| ES (1) | ES2966827T3 (enExample) |
| IL (1) | IL273000B2 (enExample) |
| MX (1) | MX2020002430A (enExample) |
| SA (1) | SA520411406B1 (enExample) |
| WO (2) | WO2019041340A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3158743A1 (en) | 2019-11-15 | 2021-05-20 | Gilead Sciences, Inc. | Triazole carbamate pyridyl sulfonamides as lpa receptor antagonists and uses thereof |
| CA3185689A1 (en) | 2020-06-03 | 2021-12-09 | Gilead Sciences, Inc. | Lpa receptor antagonists and uses thereof |
| TWI843503B (zh) | 2020-06-03 | 2024-05-21 | 美商基利科學股份有限公司 | Lpa受體拮抗劑及其用途 |
| CA3218917A1 (en) | 2021-05-11 | 2022-11-17 | Gilead Sciences, Inc. | Lpa receptor antagonists and uses thereof |
| CN113461640B (zh) * | 2021-06-17 | 2023-08-11 | 中央民族大学 | Lpar1抑制剂、医药用途及其制备方法 |
| AU2022405082B2 (en) | 2021-12-08 | 2025-09-25 | Gilead Sciences, Inc. | Lpa receptor antagonists and uses thereof |
| AR128613A1 (es) | 2022-02-25 | 2024-05-29 | Lhotse Bio Inc | Compuestos y composiciones para el tratamiento de afecciones asociadas con la actividad del receptor de lpa |
| WO2024112895A1 (en) * | 2022-11-24 | 2024-05-30 | Lhotse Bio, Inc. | Compounds and compositions for treating conditions associated with lpa receptor activity |
| WO2024249867A1 (en) * | 2023-06-02 | 2024-12-05 | Am Sciences | Compounds for treating fibrotic diseases |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2466121B (en) * | 2008-12-15 | 2010-12-08 | Amira Pharmaceuticals Inc | Antagonists of lysophosphatidic acid receptors |
| GB2474748B (en) * | 2009-10-01 | 2011-10-12 | Amira Pharmaceuticals Inc | Polycyclic compounds as lysophosphatidic acid receptor antagonists |
| GB2474120B (en) * | 2009-10-01 | 2011-12-21 | Amira Pharmaceuticals Inc | Compounds as Lysophosphatidic acid receptor antagonists |
| BR112013014019A2 (pt) * | 2010-12-07 | 2016-09-13 | Amira Pharmaceuticals Inc | antagonistas do receptor do ácido lisofosfatídico e seus usos |
| EP2694496A1 (en) * | 2011-04-05 | 2014-02-12 | Amira Pharmaceuticals, Inc. | 3- or 5 - bi phenyl - 4 - ylisoxazole - based compounds useful for the treatment of fibrosis, pain, cancer and respiratory, allergic, nervous system or cardiovascular disorders |
| WO2012138648A1 (en) * | 2011-04-06 | 2012-10-11 | Irm Llc | Compositions and methods for modulating lpa receptors |
| US9526091B2 (en) * | 2012-03-16 | 2016-12-20 | Intel Corporation | Method and apparatus for coordination of self-optimization functions in a wireless network |
| CA3005811A1 (en) | 2015-11-20 | 2017-05-26 | Ube Industries, Ltd. | Pharmaceutical composition for treatment or prevention of nash |
-
2017
- 2017-09-04 WO PCT/CN2017/100354 patent/WO2019041340A1/en not_active Ceased
-
2018
- 2018-08-28 EP EP18766481.8A patent/EP3679032B1/en active Active
- 2018-08-28 CN CN201880053540.2A patent/CN111032647B/zh active Active
- 2018-08-28 AU AU2018323969A patent/AU2018323969B2/en active Active
- 2018-08-28 EA EA202090368A patent/EA039482B1/ru unknown
- 2018-08-28 WO PCT/US2018/048249 patent/WO2019046239A1/en not_active Ceased
- 2018-08-28 US US16/633,371 patent/US11365185B2/en active Active
- 2018-08-28 CA CA3073983A patent/CA3073983C/en active Active
- 2018-08-28 JP JP2020512678A patent/JP6854386B2/ja active Active
- 2018-08-28 ES ES18766481T patent/ES2966827T3/es active Active
- 2018-08-28 KR KR1020207006096A patent/KR102341064B1/ko active Active
- 2018-08-28 MX MX2020002430A patent/MX2020002430A/es unknown
-
2020
- 2020-02-25 SA SA520411406A patent/SA520411406B1/ar unknown
- 2020-03-01 IL IL273000A patent/IL273000B2/en unknown
-
2022
- 2022-05-18 US US17/747,261 patent/US12145924B2/en active Active