JP2017511329A5 - - Google Patents
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- Publication number
- JP2017511329A5 JP2017511329A5 JP2016560389A JP2016560389A JP2017511329A5 JP 2017511329 A5 JP2017511329 A5 JP 2017511329A5 JP 2016560389 A JP2016560389 A JP 2016560389A JP 2016560389 A JP2016560389 A JP 2016560389A JP 2017511329 A5 JP2017511329 A5 JP 2017511329A5
- Authority
- JP
- Japan
- Prior art keywords
- oxy
- amine
- dimethylpentan
- methyl
- difluoromethyl
- 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 methoxy, methyl Chemical group 0.000 claims 34
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- RKAHOQATMSONTM-IBGZPJMESA-N FC(C1=NC=CC(=C1)C1=NC(=C(C=C1)OC[C@](CC(C)C)(N)C)C(F)F)F Chemical compound FC(C1=NC=CC(=C1)C1=NC(=C(C=C1)OC[C@](CC(C)C)(N)C)C(F)F)F RKAHOQATMSONTM-IBGZPJMESA-N 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- 102100038079 AP2-associated protein kinase 1 Human genes 0.000 claims 2
- PJYKLDMCKAFIQS-IBGZPJMESA-N CC(C)C[C@](C)(N)COC1=C(N=C(C=C1)C1=C(F)C(C)=NC=C1)C(F)F Chemical class CC(C)C[C@](C)(N)COC1=C(N=C(C=C1)C1=C(F)C(C)=NC=C1)C(F)F PJYKLDMCKAFIQS-IBGZPJMESA-N 0.000 claims 2
- RKBMAROJKLHAMI-IBGZPJMESA-N CC(C)C[C@](C)(N)COC1=CN=C(C=C1C(F)F)C1=CC(C)=NC=C1 Chemical compound CC(C)C[C@](C)(N)COC1=CN=C(C=C1C(F)F)C1=CC(C)=NC=C1 RKBMAROJKLHAMI-IBGZPJMESA-N 0.000 claims 2
- AALSHYORLVJEBZ-SFHVURJKSA-N CC(C)C[C@](C)(N)COC1=NC=C(C=C1C(F)F)C1=CC=NC(C)=N1 Chemical compound CC(C)C[C@](C)(N)COC1=NC=C(C=C1C(F)F)C1=CC=NC(C)=N1 AALSHYORLVJEBZ-SFHVURJKSA-N 0.000 claims 2
- ULGONQSWPGCYPW-IBGZPJMESA-N C[C@@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)C)C(F)(F)F)(CC(C)C)N Chemical compound C[C@@](COC1=C(C=C(C=C1)C1=CC(=NC=C1)C)C(F)(F)F)(CC(C)C)N ULGONQSWPGCYPW-IBGZPJMESA-N 0.000 claims 2
- YXRJMGXKRWHQME-SFHVURJKSA-N C[C@@](COC=1C(=CC(=NC1)C1=CC(=NC=C1)C)C(F)(F)F)(CC(C)C)N Chemical compound C[C@@](COC=1C(=CC(=NC1)C1=CC(=NC=C1)C)C(F)(F)F)(CC(C)C)N YXRJMGXKRWHQME-SFHVURJKSA-N 0.000 claims 2
- DCWNOICLZKGXFR-IBGZPJMESA-N FC(C1=CC(=NC=C1OC[C@](CC(C)C)(N)C)C1=C(C(=NC=C1)C)F)F Chemical class FC(C1=CC(=NC=C1OC[C@](CC(C)C)(N)C)C1=C(C(=NC=C1)C)F)F DCWNOICLZKGXFR-IBGZPJMESA-N 0.000 claims 2
- NFTPBBCMDGZSHJ-MHZLTWQESA-N FC1=CC=C2C(=CC=NC2=C1)C1=CC(=C(C=N1)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C Chemical compound FC1=CC=C2C(=CC=NC2=C1)C1=CC(=C(C=N1)OC[C@@](CC(C)C)(C)NC(OC(C)(C)C)=O)C NFTPBBCMDGZSHJ-MHZLTWQESA-N 0.000 claims 2
- 101000742699 Homo sapiens AP2-associated protein kinase 1 Proteins 0.000 claims 2
- JJNHJOVVASIHIL-INIZCTEOSA-N N[C@H](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)F)CC(C)C Chemical compound N[C@H](COC1=C(C=C(C=C1)C1=CC(=NC=C1)NC(C)=O)F)CC(C)C JJNHJOVVASIHIL-INIZCTEOSA-N 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
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- AALSHYORLVJEBZ-GOSISDBHSA-N (2R)-1-[3-(difluoromethyl)-5-(2-methylpyrimidin-4-yl)pyridin-2-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound FC(C=1C(=NC=C(C1)C1=NC(=NC=C1)C)OC[C@@](CC(C)C)(N)C)F AALSHYORLVJEBZ-GOSISDBHSA-N 0.000 claims 1
- WIIALNVSHHTFFZ-JOCHJYFZSA-N (2R)-1-[3-(difluoromethyl)-5-(5,7-difluoroquinolin-4-yl)pyridin-2-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound FC(C=1C(=NC=C(C=1)C1=CC=NC2=CC(=CC(=C12)F)F)OC[C@@](CC(C)C)(N)C)F WIIALNVSHHTFFZ-JOCHJYFZSA-N 0.000 claims 1
- OKSLIDNQBOADCD-JOCHJYFZSA-N (2R)-1-[5-(7-chloroquinolin-4-yl)-3-(difluoromethyl)pyridin-2-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound ClC1=CC=C2C(=CC=NC2=C1)C=1C=C(C(=NC1)OC[C@@](CC(C)C)(N)C)C(F)F OKSLIDNQBOADCD-JOCHJYFZSA-N 0.000 claims 1
- QZNNODQLLRSCHN-VWLOTQADSA-N (2S)-1-(2-cyclopropyl-4-quinolin-4-ylphenoxy)-2,4-dimethylpentan-2-amine Chemical compound C1(CC1)C1=C(OC[C@](CC(C)C)(N)C)C=CC(=C1)C1=CC=NC2=CC=CC=C12 QZNNODQLLRSCHN-VWLOTQADSA-N 0.000 claims 1
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- BIQHWJJDUAWYEN-SFHVURJKSA-N (2S)-1-[2-(difluoromethyl)-6-(2-methylpyrimidin-4-yl)pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=CC=C(N=C1C(F)F)C1=CC=NC(C)=N1 BIQHWJJDUAWYEN-SFHVURJKSA-N 0.000 claims 1
- APTYRPSOZMZHRQ-QFIPXVFZSA-N (2S)-1-[2-(difluoromethyl)-6-(5,7-difluoroquinolin-4-yl)pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=CC=C(N=C1C(F)F)C1=CC=NC2=CC(F)=CC(F)=C12 APTYRPSOZMZHRQ-QFIPXVFZSA-N 0.000 claims 1
- YJVNBILWESXTRQ-SFHVURJKSA-N (2S)-1-[2-(difluoromethyl)-6-(6-methylpyrimidin-4-yl)pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=CC=C(N=C1C(F)F)C1=CC(C)=NC=N1 YJVNBILWESXTRQ-SFHVURJKSA-N 0.000 claims 1
- VONWNHVCOBGODO-SFHVURJKSA-N (2S)-1-[2-fluoro-4-(2-fluoropyridin-4-yl)phenoxy]-2,4-dimethylpentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=C(F)C=C(C=C1)C1=CC(F)=NC=C1 VONWNHVCOBGODO-SFHVURJKSA-N 0.000 claims 1
- QYLMAGMUZOOXAT-FQEVSTJZSA-N (2S)-1-[4-(difluoromethyl)-6-(2-ethylpyridin-4-yl)pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound CCC1=NC=CC(=C1)C1=NC=C(OC[C@@](C)(N)CC(C)C)C(=C1)C(F)F QYLMAGMUZOOXAT-FQEVSTJZSA-N 0.000 claims 1
- CDMSYPKSRHQLQX-SFHVURJKSA-N (2S)-1-[4-(difluoromethyl)-6-(2-methylpyrimidin-4-yl)pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(N=C1)C1=CC=NC(C)=N1)C(F)F CDMSYPKSRHQLQX-SFHVURJKSA-N 0.000 claims 1
- VQPKLYXPUPPWOJ-QFIPXVFZSA-N (2S)-1-[4-(difluoromethyl)-6-[6-(trifluoromethoxy)quinolin-4-yl]pyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound FC(C1=C(C=NC(=C1)C1=CC=NC2=CC=C(C=C12)OC(F)(F)F)OC[C@](CC(C)C)(N)C)F VQPKLYXPUPPWOJ-QFIPXVFZSA-N 0.000 claims 1
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- KHGSGIDZUJKCPA-QFIPXVFZSA-N (2S)-1-[6-(6-fluoroquinolin-4-yl)-2-methylpyridin-3-yl]oxy-2,4-dimethylpentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=CC=C(N=C1C)C1=CC=NC2=CC=C(F)C=C12 KHGSGIDZUJKCPA-QFIPXVFZSA-N 0.000 claims 1
- NOJOTLCVBXCQCU-QHCPKHFHSA-N (2S)-2,4-dimethyl-1-(2-methylsulfonyl-4-quinolin-4-ylphenoxy)pentan-2-amine Chemical compound CC(C)C[C@](C)(N)COC1=C(C=C(C=C1)C1=CC=NC2=CC=CC=C12)S(C)(=O)=O NOJOTLCVBXCQCU-QHCPKHFHSA-N 0.000 claims 1
- PPHIUCCSQWZQGM-QFIPXVFZSA-N 4-[6-[(2S)-2-amino-2,4-dimethylpentoxy]-5-fluoropyridin-3-yl]quinoline-7-carbonitrile Chemical compound CC(C)C[C@](C)(N)COC1=C(F)C=C(C=N1)C1=CC=NC2=CC(=CC=C12)C#N PPHIUCCSQWZQGM-QFIPXVFZSA-N 0.000 claims 1
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| US8901305B2 (en) * | 2012-07-31 | 2014-12-02 | Bristol-Myers Squibb Company | Aryl lactam kinase inhibitors |
| JP2016509066A (ja) | 2013-02-22 | 2016-03-24 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | アダプター関連キナーゼ１（ａａｋ１）の阻害剤としての５ｈ−クロメノ［３，４−ｃ］ピリジン |
| WO2015006100A1 (en) | 2013-07-08 | 2015-01-15 | Bristol-Myers Squibb Company | Aryl amide kinase inhibitors |
| WO2015038112A1 (en) | 2013-09-11 | 2015-03-19 | Bristol-Myers Squibb Company | Aryl ether-base kinase inhibitors |
| EP3099300B1 (en) | 2014-01-29 | 2018-09-05 | Bristol-Myers Squibb Company | Aryl lactam kinase inhibitors |
| ES2701903T3 (es) | 2014-01-31 | 2019-02-26 | Bristol Myers Squibb Co | Inhibidores de cinasa a base de quinolina |
| KR102379518B1 (ko) * | 2014-04-02 | 2022-03-25 | 브리스톨-마이어스 스큅 컴퍼니 | 비아릴 키나제 억제제 |
| EP3200797A1 (en) | 2014-09-30 | 2017-08-09 | Bristol-Myers Squibb Company | Quinazoline-based kinase inhibitors |
| EP3292124B1 (en) | 2015-04-10 | 2019-05-22 | Bristol-Myers Squibb Company | 6h-isochromeno[3,4-c]pyridines and benzo[c][1,7]naphthyridin-6-(5h)-ones as adaptor associated kinase 1 (aak1) inhibitors |
| ES2767776T3 (es) | 2015-10-01 | 2020-06-18 | Bristol Myers Squibb Co | Inhibidores de biaril cinasa |
| US10544120B2 (en) * | 2015-10-01 | 2020-01-28 | Bristol-Myers Squibb Company | Biaryl kinase inhibitors |
| US10981190B2 (en) | 2018-07-06 | 2021-04-20 | Liqui-Box Corporation | Dispensing probe for dispensing flowable material |
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