JP2019515903A5 - - Google Patents
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- Publication number
- JP2019515903A5 JP2019515903A5 JP2018554114A JP2018554114A JP2019515903A5 JP 2019515903 A5 JP2019515903 A5 JP 2019515903A5 JP 2018554114 A JP2018554114 A JP 2018554114A JP 2018554114 A JP2018554114 A JP 2018554114A JP 2019515903 A5 JP2019515903 A5 JP 2019515903A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- amino
- pyrazolo
- pyrimidin
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 93
- 229910052739 hydrogen Inorganic materials 0.000 claims 50
- 239000001257 hydrogen Substances 0.000 claims 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 38
- 125000005843 halogen group Chemical group 0.000 claims 29
- 150000001875 compounds Chemical class 0.000 claims 28
- 125000003118 aryl group Chemical group 0.000 claims 27
- 125000001424 substituent group Chemical group 0.000 claims 27
- -1 cyano, hydroxy, carboxy, carbamoyl Chemical group 0.000 claims 25
- 150000003839 salts Chemical class 0.000 claims 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims 23
- 125000001188 haloalkyl group Chemical group 0.000 claims 21
- 125000004438 haloalkoxy group Chemical group 0.000 claims 20
- 239000012453 solvate Substances 0.000 claims 20
- 125000003545 alkoxy group Chemical group 0.000 claims 19
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 229910052757 nitrogen Inorganic materials 0.000 claims 17
- 125000001072 heteroaryl group Chemical group 0.000 claims 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 16
- 125000003282 alkyl amino group Chemical group 0.000 claims 12
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 12
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 239000003795 chemical substances by application Substances 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 206010028980 Neoplasm Diseases 0.000 claims 8
- 102100028286 Proto-oncogene tyrosine-protein kinase receptor Ret Human genes 0.000 claims 8
- 201000011510 cancer Diseases 0.000 claims 8
- 125000002947 alkylene group Chemical group 0.000 claims 7
- 125000000304 alkynyl group Chemical group 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 150000002431 hydrogen Chemical group 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 230000035772 mutation Effects 0.000 claims 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 208000009018 Medullary thyroid cancer Diseases 0.000 claims 2
- 230000010261 cell growth Effects 0.000 claims 2
- 230000004927 fusion Effects 0.000 claims 2
- 208000023356 medullary thyroid gland carcinoma Diseases 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
- 230000005945 translocation Effects 0.000 claims 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 2
- DSKWNVPCROYIQW-UHFFFAOYSA-N 2-(4-amino-1-cyclobutylpyrazolo[3,4-d]pyrimidin-3-yl)-3-chloro-N-methyl-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC)C1CCC1 DSKWNVPCROYIQW-UHFFFAOYSA-N 0.000 claims 1
- JATHVEVHCNBUNG-UHFFFAOYSA-N 2-(4-amino-1-cyclohexylpyrazolo[3,4-d]pyrimidin-3-yl)-3-chloro-N-methyl-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC)C1CCCCC1 JATHVEVHCNBUNG-UHFFFAOYSA-N 0.000 claims 1
- QBXTYIQNVFGQQN-UHFFFAOYSA-N 2-(4-amino-1-propan-2-ylpyrazolo[4,3-c]pyridin-3-yl)-3-chloro-N-methyl-1H-indole-6-carboxamide Chemical compound NC1=NC=CC2=C1C(=NN2C(C)C)C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC QBXTYIQNVFGQQN-UHFFFAOYSA-N 0.000 claims 1
- KHWXTXSKIPRCHN-UHFFFAOYSA-N 2-(4-amino-1-tert-butylpyrazolo[3,4-d]pyrimidin-3-yl)-1-methylindole-6-carboxylic acid Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1N(C2=CC(=CC=C2C=1)C(=O)O)C)C(C)(C)C KHWXTXSKIPRCHN-UHFFFAOYSA-N 0.000 claims 1
- OGUFXWBZNKEOCD-UHFFFAOYSA-N 2-(4-amino-1-tert-butylpyrazolo[3,4-d]pyrimidin-3-yl)-3-bromo-N-methyl-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Br)C(=O)NC)C(C)(C)C OGUFXWBZNKEOCD-UHFFFAOYSA-N 0.000 claims 1
- JENIHZJYWBWMAT-UHFFFAOYSA-N 2-(4-amino-1-tert-butylpyrazolo[3,4-d]pyrimidin-3-yl)-3-chloro-1H-indole-6-carboxylic acid Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)O)C(C)(C)C JENIHZJYWBWMAT-UHFFFAOYSA-N 0.000 claims 1
- XKSROQSJCOMSFN-UHFFFAOYSA-N 2-(4-amino-1-tert-butylpyrazolo[3,4-d]pyrimidin-3-yl)-3-chloro-N-(2-hydroxyethyl)-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NCCO)C(C)(C)C XKSROQSJCOMSFN-UHFFFAOYSA-N 0.000 claims 1
- GATYLOYCUAPWMB-UHFFFAOYSA-N 2-(4-amino-1-tert-butylpyrazolo[3,4-d]pyrimidin-3-yl)-3-chloro-N-(2-morpholin-4-ylethyl)-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NCCN1CCOCC1)C(C)(C)C GATYLOYCUAPWMB-UHFFFAOYSA-N 0.000 claims 1
- MJSDVPHVJFPGEB-UHFFFAOYSA-N 2-(4-amino-1-tert-butylpyrazolo[3,4-d]pyrimidin-3-yl)-3-chloro-N-(3-piperidin-1-ylpropyl)-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NCCCN1CCCCC1)C(C)(C)C MJSDVPHVJFPGEB-UHFFFAOYSA-N 0.000 claims 1
- JONUNFKBZRKJSB-UHFFFAOYSA-N 2-(4-amino-1-tert-butylpyrazolo[3,4-d]pyrimidin-3-yl)-3-chloro-N-(oxan-4-yl)-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC1CCOCC1)C(C)(C)C JONUNFKBZRKJSB-UHFFFAOYSA-N 0.000 claims 1
- ACNNJWMMLBYERQ-UHFFFAOYSA-N 2-(4-amino-1-tert-butylpyrazolo[3,4-d]pyrimidin-3-yl)-3-chloro-N-[1-(2-hydroxyethyl)pyrazol-3-yl]-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC1=NN(C=C1)CCO)C(C)(C)C ACNNJWMMLBYERQ-UHFFFAOYSA-N 0.000 claims 1
- RAKDOBWGYQVOPT-UHFFFAOYSA-N 2-(4-amino-1-tert-butylpyrazolo[3,4-d]pyrimidin-3-yl)-3-chloro-N-[1-(2-methoxyethyl)pyrazol-3-yl]-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC1=NN(C=C1)CCOC)C(C)(C)C RAKDOBWGYQVOPT-UHFFFAOYSA-N 0.000 claims 1
- XEDLQHAQDJOFQI-UHFFFAOYSA-N 2-(4-amino-1-tert-butylpyrazolo[3,4-d]pyrimidin-3-yl)-3-chloro-N-[1-(2-morpholin-4-ylethyl)pyrazol-3-yl]-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC1=NN(C=C1)CCN1CCOCC1)C(C)(C)C XEDLQHAQDJOFQI-UHFFFAOYSA-N 0.000 claims 1
- CDNJXEIHIBWNAM-UHFFFAOYSA-N 2-(4-amino-1-tert-butylpyrazolo[3,4-d]pyrimidin-3-yl)-3-chloro-N-[2-(2-morpholin-4-ylethoxy)ethyl]-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NCCOCCN1CCOCC1)C(C)(C)C CDNJXEIHIBWNAM-UHFFFAOYSA-N 0.000 claims 1
- FFPFOCJSSHPGFQ-UHFFFAOYSA-N 2-(4-amino-1-tert-butylpyrazolo[3,4-d]pyrimidin-3-yl)-3-chloro-N-cyclopropyl-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC1CC1)C(C)(C)C FFPFOCJSSHPGFQ-UHFFFAOYSA-N 0.000 claims 1
- PYVFQLBTKLTYTG-UHFFFAOYSA-N 2-(4-amino-1-tert-butylpyrazolo[3,4-d]pyrimidin-3-yl)-3-chloro-N-ethyl-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NCC)C(C)(C)C PYVFQLBTKLTYTG-UHFFFAOYSA-N 0.000 claims 1
- SVRNPAWUQSRQDR-UHFFFAOYSA-N 2-(4-amino-1-tert-butylpyrazolo[3,4-d]pyrimidin-3-yl)-3-chloro-N-methoxy-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NOC)C(C)(C)C SVRNPAWUQSRQDR-UHFFFAOYSA-N 0.000 claims 1
- JPKMVXLPXRWJMH-UHFFFAOYSA-N 2-(4-amino-1-tert-butylpyrazolo[3,4-d]pyrimidin-3-yl)-3-chloro-N-methyl-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC)C(C)(C)C JPKMVXLPXRWJMH-UHFFFAOYSA-N 0.000 claims 1
- MERLQASBRDWKDQ-UHFFFAOYSA-N 2-(4-amino-1-tert-butylpyrazolo[3,4-d]pyrimidin-3-yl)-3-chloro-N-methyl-1H-pyrrolo[2,3-b]pyridine-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C1=C(C=2C(=NC(=CC=2)C(=O)NC)N1)Cl)C(C)(C)C MERLQASBRDWKDQ-UHFFFAOYSA-N 0.000 claims 1
- QYNGSKKAMMMUSU-UHFFFAOYSA-N 2-(4-amino-1-tert-butylpyrazolo[3,4-d]pyrimidin-3-yl)-3-chloro-N-phenyl-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC1=CC=CC=C1)C(C)(C)C QYNGSKKAMMMUSU-UHFFFAOYSA-N 0.000 claims 1
- AHVGUCBWHJIREZ-UHFFFAOYSA-N 2-(4-amino-1-tert-butylpyrazolo[3,4-d]pyrimidin-3-yl)-3-chloro-N-propan-2-yl-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC(C)C)C(C)(C)C AHVGUCBWHJIREZ-UHFFFAOYSA-N 0.000 claims 1
- ZKCVPKGPHDGZDJ-UHFFFAOYSA-N 2-(4-amino-1-tert-butylpyrazolo[3,4-d]pyrimidin-3-yl)-N,1-dimethylindole-6-carboxamide Chemical compound CNC(=O)c1ccc2cc(-c3nn(c4ncnc(N)c34)C(C)(C)C)n(C)c2c1 ZKCVPKGPHDGZDJ-UHFFFAOYSA-N 0.000 claims 1
- VYARLCVNNHTNAM-UHFFFAOYSA-N 2-(4-amino-7-propan-2-ylimidazo[5,1-f][1,2,4]triazin-5-yl)-3-chloro-N-methyl-1H-indole-6-carboxamide Chemical compound NC1=NC=NN2C1=C(N=C2C(C)C)C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC VYARLCVNNHTNAM-UHFFFAOYSA-N 0.000 claims 1
- DILHJTZQDCOPRO-UHFFFAOYSA-N 2-(4-amino-7-propan-2-ylpyrrolo[2,1-f][1,2,4]triazin-5-yl)-3-chloro-N-methyl-1H-indole-6-carboxamide Chemical compound NC1=NC=NN2C1=C(C=C2C(C)C)C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC DILHJTZQDCOPRO-UHFFFAOYSA-N 0.000 claims 1
- ZWNXAOSIOZQDJI-UHFFFAOYSA-N 2-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidin-5-yl)-3-chloro-N-methyl-1H-indole-6-carboxamide Chemical compound NC=1C2=C(N=CN=1)N(C=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC)C(C)C ZWNXAOSIOZQDJI-UHFFFAOYSA-N 0.000 claims 1
- BYSACNLCTNNHPN-UHFFFAOYSA-N 2-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidin-5-yl)-N-methyl-1H-indole-6-carboxamide Chemical compound CNC(=O)c1ccc2cc([nH]c2c1)-c1cn(C(C)C)c2ncnc(N)c12 BYSACNLCTNNHPN-UHFFFAOYSA-N 0.000 claims 1
- PROVTCUQULPWSW-UHFFFAOYSA-N 2-(4-aminothieno[2,3-d]pyrimidin-5-yl)-3-chloro-N-methyl-1H-indole-6-carboxamide Chemical compound NC=1C2=C(N=CN=1)SC=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC PROVTCUQULPWSW-UHFFFAOYSA-N 0.000 claims 1
- IHZHNFHAODVCHG-UHFFFAOYSA-N 2-(4-aminothieno[2,3-d]pyrimidin-5-yl)-N-methyl-1H-indole-6-carboxamide Chemical compound CNC(=O)c1ccc2cc([nH]c2c1)-c1csc2ncnc(N)c12 IHZHNFHAODVCHG-UHFFFAOYSA-N 0.000 claims 1
- BQUHSWVUQMWBKQ-UHFFFAOYSA-N 2-(8-amino-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl)-3-chloro-N-methyl-1H-indole-6-carboxamide Chemical compound NC=1C=2N(C=CN=1)C(=NC=2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC)C(C)C BQUHSWVUQMWBKQ-UHFFFAOYSA-N 0.000 claims 1
- VDNPELONOYHGLO-UHFFFAOYSA-N 2-(8-amino-3-propan-2-ylimidazo[1,5-a]pyrazin-1-yl)-N-methyl-1H-indole-6-carboxamide Chemical compound CNC(=O)c1ccc2cc([nH]c2c1)-c1nc(C(C)C)n2ccnc(N)c12 VDNPELONOYHGLO-UHFFFAOYSA-N 0.000 claims 1
- CZHZUJVGXKKWOK-UHFFFAOYSA-N 2-[4-amino-1-(1-methylpiperidin-4-yl)pyrazolo[3,4-d]pyrimidin-3-yl]-3-chloro-N-cyclopropyl-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC1CC1)C1CCN(CC1)C CZHZUJVGXKKWOK-UHFFFAOYSA-N 0.000 claims 1
- HDRICYBPUIHGFB-UHFFFAOYSA-N 2-[4-amino-1-(1-methylsulfonylpiperidin-4-yl)pyrazolo[3,4-d]pyrimidin-3-yl]-3-chloro-N-methyl-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC)C1CCN(CC1)S(=O)(=O)C HDRICYBPUIHGFB-UHFFFAOYSA-N 0.000 claims 1
- MTVIBLNIVAZDBD-UHFFFAOYSA-N 2-[4-amino-1-(2-hydroxyethyl)pyrazolo[3,4-d]pyrimidin-3-yl]-3-chloro-N-methyl-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC)CCO MTVIBLNIVAZDBD-UHFFFAOYSA-N 0.000 claims 1
- VEEAEHXPQMQIAP-UHFFFAOYSA-N 2-[4-amino-1-(3-methoxypropyl)pyrazolo[3,4-d]pyrimidin-3-yl]-3-chloro-N-methyl-1H-indole-6-carboxamide Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1Cl)C(=O)NC)CCCOC VEEAEHXPQMQIAP-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- POGSLQNMTATYLA-UHFFFAOYSA-N C(C)(C)N1N=C(C=2C1=NC=NC=2N)C=1NC2=CC(=CC=C2C=1)C=1SC=NN=1 Chemical compound C(C)(C)N1N=C(C=2C1=NC=NC=2N)C=1NC2=CC(=CC=C2C=1)C=1SC=NN=1 POGSLQNMTATYLA-UHFFFAOYSA-N 0.000 claims 1
- NHIXNLZVPJKYHL-UHFFFAOYSA-N C1=CC2=C(C=C1C3=NC=CO3)NC(=C2)C4=C5C(=NC=NC5=NN4)N Chemical compound C1=CC2=C(C=C1C3=NC=CO3)NC(=C2)C4=C5C(=NC=NC5=NN4)N NHIXNLZVPJKYHL-UHFFFAOYSA-N 0.000 claims 1
- NSZXLMVQBNISCL-UHFFFAOYSA-N ClC1=C(NC2=CC(=CC=C12)C=1OC=CN=1)C1=NN(C2=NC=NC(=C21)N)C(C)C Chemical compound ClC1=C(NC2=CC(=CC=C12)C=1OC=CN=1)C1=NN(C2=NC=NC(=C21)N)C(C)C NSZXLMVQBNISCL-UHFFFAOYSA-N 0.000 claims 1
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- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
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- CQRYLFOODJKGGH-UHFFFAOYSA-N NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1)C(=O)NC)C1CCCC1 Chemical compound NC1=C2C(=NC=N1)N(N=C2C=1NC2=CC(=CC=C2C=1)C(=O)NC)C1CCCC1 CQRYLFOODJKGGH-UHFFFAOYSA-N 0.000 claims 1
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| CA3049136C (en) | 2017-01-18 | 2022-06-14 | Array Biopharma Inc. | Substituted pyrazolo[1,5-a]pyrazine compounds as ret kinase inhibitors |
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| TWI812649B (zh) | 2017-10-10 | 2023-08-21 | 美商絡速藥業公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之調配物 |
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