JP2016523893A5 - - Google Patents
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- JP2016523893A5 JP2016523893A5 JP2016522952A JP2016522952A JP2016523893A5 JP 2016523893 A5 JP2016523893 A5 JP 2016523893A5 JP 2016522952 A JP2016522952 A JP 2016522952A JP 2016522952 A JP2016522952 A JP 2016522952A JP 2016523893 A5 JP2016523893 A5 JP 2016523893A5
- Authority
- JP
- Japan
- Prior art keywords
- amine
- quinolin
- group
- hydrogen atom
- chloro
- 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.)
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 235
- 229910052799 carbon Inorganic materials 0.000 claims description 224
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 96
- 241001430294 unidentified retrovirus Species 0.000 claims description 92
- 229910052757 nitrogen Inorganic materials 0.000 claims description 88
- 241000282414 Homo sapiens Species 0.000 claims description 71
- 208000032839 leukemia Diseases 0.000 claims description 70
- 125000005843 halogen group Chemical group 0.000 claims description 66
- 239000006260 foam Substances 0.000 claims description 64
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- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 39
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 208000023275 Autoimmune disease Diseases 0.000 claims description 24
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- 208000012902 Nervous system disease Diseases 0.000 claims description 22
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- 241000288906 Primates Species 0.000 claims description 22
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- 241001529934 Simian T-lymphotropic virus 3 Species 0.000 claims description 22
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- 206010042971 T-cell lymphoma Diseases 0.000 claims description 22
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims description 22
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- 238000000034 method Methods 0.000 claims description 22
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- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 16
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- DGRWWQSIXMNUFG-UHFFFAOYSA-N n-pyridin-2-ylquinoxalin-2-amine Chemical compound C=1N=C2C=CC=CC2=NC=1NC1=CC=CC=N1 DGRWWQSIXMNUFG-UHFFFAOYSA-N 0.000 claims description 9
- YFSKNMVMVDRGQL-UHFFFAOYSA-N 1-n-(6-chloroquinolin-2-yl)-4-n,4-n-dimethylbenzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1NC1=CC=C(C=C(Cl)C=C2)C2=N1 YFSKNMVMVDRGQL-UHFFFAOYSA-N 0.000 claims description 8
- KROFVRIRTYNLBH-UHFFFAOYSA-N 1-n-(8-chloroquinolin-2-yl)-4-(trifluoromethoxy)benzene-1,2-diamine Chemical compound NC1=CC(OC(F)(F)F)=CC=C1NC1=CC=C(C=CC=C2Cl)C2=N1 KROFVRIRTYNLBH-UHFFFAOYSA-N 0.000 claims description 8
- SJQBOAPYEWHLJK-UHFFFAOYSA-N 1-n-(8-chloroquinolin-2-yl)-4-n,4-n-dimethylbenzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1NC1=CC=C(C=CC=C2Cl)C2=N1 SJQBOAPYEWHLJK-UHFFFAOYSA-N 0.000 claims description 8
- AGJXIRGBYDQMRP-UHFFFAOYSA-N 2-(quinolin-2-ylamino)pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC(NC=2N=C3C=CC=CC3=CC=2)=C1 AGJXIRGBYDQMRP-UHFFFAOYSA-N 0.000 claims description 8
- FXWXPPMZBPDNTC-UHFFFAOYSA-N 2-(quinolin-2-ylamino)pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(NC=2N=C3C=CC=CC3=CC=2)=C1 FXWXPPMZBPDNTC-UHFFFAOYSA-N 0.000 claims description 8
- PLFPWCLLFOJLBI-UHFFFAOYSA-N 2-(quinolin-3-ylamino)pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(NC=2C=C3C=CC=CC3=NC=2)=C1 PLFPWCLLFOJLBI-UHFFFAOYSA-N 0.000 claims description 8
- JXMJKMAWRLFXAP-UHFFFAOYSA-N 2-[(4-methylquinolin-2-yl)amino]pyridine-3-carbonitrile Chemical compound N=1C2=CC=CC=C2C(C)=CC=1NC1=NC=CC=C1C#N JXMJKMAWRLFXAP-UHFFFAOYSA-N 0.000 claims description 8
- BKJDCCJYCUPNRL-UHFFFAOYSA-N 2-[(8-chloroquinolin-2-yl)amino]pyridin-3-ol Chemical compound OC1=CC=CN=C1NC1=CC=C(C=CC=C2Cl)C2=N1 BKJDCCJYCUPNRL-UHFFFAOYSA-N 0.000 claims description 8
- UBKNQKFAALWYST-UHFFFAOYSA-N 2-[(8-chloroquinolin-2-yl)amino]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1NC1=CC=C(C=CC=C2Cl)C2=N1 UBKNQKFAALWYST-UHFFFAOYSA-N 0.000 claims description 8
- SXYZJVGUCCEKGQ-UHFFFAOYSA-N 2-[(8-chloroquinolin-2-yl)amino]pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC(NC=2N=C3C(Cl)=CC=CC3=CC=2)=C1 SXYZJVGUCCEKGQ-UHFFFAOYSA-N 0.000 claims description 8
- YFKLMAPHIMPQJI-UHFFFAOYSA-N 2-n-(4-methylpyridin-2-yl)quinoline-2,5-diamine Chemical compound CC1=CC=NC(NC=2N=C3C=CC=C(N)C3=CC=2)=C1 YFKLMAPHIMPQJI-UHFFFAOYSA-N 0.000 claims description 8
- LQYGHYLIGWZTLP-UHFFFAOYSA-N 2-n-(4-methylpyridin-2-yl)quinoline-2,8-diamine Chemical compound CC1=CC=NC(NC=2N=C3C(N)=CC=CC3=CC=2)=C1 LQYGHYLIGWZTLP-UHFFFAOYSA-N 0.000 claims description 8
- VGWOMTPTPCNRSD-UHFFFAOYSA-N 2-n-(8-chloroquinolin-2-yl)-4-methylpyridine-2,3-diamine Chemical compound CC1=CC=NC(NC=2N=C3C(Cl)=CC=CC3=CC=2)=C1N VGWOMTPTPCNRSD-UHFFFAOYSA-N 0.000 claims description 8
- GKQWGUCKPKFKBV-UHFFFAOYSA-N 2-n-quinolin-3-ylpyridine-2,3-diamine Chemical compound NC1=CC=CN=C1NC1=CN=C(C=CC=C2)C2=C1 GKQWGUCKPKFKBV-UHFFFAOYSA-N 0.000 claims description 8
- YRKSELLNQXQCRF-UHFFFAOYSA-N 3-methyl-n-(4-methylpyridin-2-yl)quinolin-2-amine Chemical compound CC1=CC=NC(NC=2C(=CC3=CC=CC=C3N=2)C)=C1 YRKSELLNQXQCRF-UHFFFAOYSA-N 0.000 claims description 8
- WTXUYUSDSQGBAN-UHFFFAOYSA-N 3-methyl-n-(6-methylpyridin-2-yl)quinolin-2-amine Chemical compound CC1=CC=CC(NC=2C(=CC3=CC=CC=C3N=2)C)=N1 WTXUYUSDSQGBAN-UHFFFAOYSA-N 0.000 claims description 8
- HLZQAAVXDMDYFS-UHFFFAOYSA-N 3-methyl-n-[2-(trifluoromethoxy)phenyl]quinolin-2-amine Chemical compound CC1=CC2=CC=CC=C2N=C1NC1=CC=CC=C1OC(F)(F)F HLZQAAVXDMDYFS-UHFFFAOYSA-N 0.000 claims description 8
- FQULGNZYLGGSSU-UHFFFAOYSA-N 3-methyl-n-[2-methyl-4-(trifluoromethoxy)phenyl]quinolin-2-amine Chemical compound CC1=CC(OC(F)(F)F)=CC=C1NC1=NC2=CC=CC=C2C=C1C FQULGNZYLGGSSU-UHFFFAOYSA-N 0.000 claims description 8
- VGMBGEVZRWQBOM-UHFFFAOYSA-N 3-methyl-n-[3-(trifluoromethoxy)phenyl]quinolin-2-amine Chemical compound CC1=CC2=CC=CC=C2N=C1NC1=CC=CC(OC(F)(F)F)=C1 VGMBGEVZRWQBOM-UHFFFAOYSA-N 0.000 claims description 8
- FWXKBWUMNDDJHT-UHFFFAOYSA-N 3-methyl-n-[4-(trifluoromethoxy)phenyl]quinolin-2-amine Chemical compound CC1=CC2=CC=CC=C2N=C1NC1=CC=C(OC(F)(F)F)C=C1 FWXKBWUMNDDJHT-UHFFFAOYSA-N 0.000 claims description 8
- RZGVHAHGCJOOLM-UHFFFAOYSA-N 3-methyl-n-[4-(trifluoromethoxy)phenyl]quinolin-2-amine;hydrochloride Chemical compound [Cl-].CC1=CC2=CC=CC=C2[NH+]=C1NC1=CC=C(OC(F)(F)F)C=C1 RZGVHAHGCJOOLM-UHFFFAOYSA-N 0.000 claims description 8
- RUIHEVIZDKFBBX-UHFFFAOYSA-N 3-methyl-n-[5-(trifluoromethyl)pyridin-2-yl]quinolin-2-amine Chemical compound CC1=CC2=CC=CC=C2N=C1NC1=CC=C(C(F)(F)F)C=N1 RUIHEVIZDKFBBX-UHFFFAOYSA-N 0.000 claims description 8
- BFRIMUUKUWOPBW-UHFFFAOYSA-N 3-methyl-n-pyrazin-2-ylquinolin-2-amine Chemical compound CC1=CC2=CC=CC=C2N=C1NC1=CN=CC=N1 BFRIMUUKUWOPBW-UHFFFAOYSA-N 0.000 claims description 8
- PJKUHBGZFLHCNB-UHFFFAOYSA-N 3-methyl-n-pyridin-2-ylquinolin-2-amine Chemical compound CC1=CC2=CC=CC=C2N=C1NC1=CC=CC=N1 PJKUHBGZFLHCNB-UHFFFAOYSA-N 0.000 claims description 8
- JKWLLRXHEBZOLZ-UHFFFAOYSA-N 4-methoxy-n-(4-methylpyridin-2-yl)quinolin-7-amine Chemical compound C=1C=C2C(OC)=CC=NC2=CC=1NC1=CC(C)=CC=N1 JKWLLRXHEBZOLZ-UHFFFAOYSA-N 0.000 claims description 8
- PFFGMKJSHDWGGT-UHFFFAOYSA-N 4-methoxy-n-[4-(trifluoromethoxy)phenyl]quinolin-7-amine Chemical compound C=1C=C2C(OC)=CC=NC2=CC=1NC1=CC=C(OC(F)(F)F)C=C1 PFFGMKJSHDWGGT-UHFFFAOYSA-N 0.000 claims description 8
- GAWOGCFTXVIYQT-UHFFFAOYSA-N 4-methoxy-n-pyridin-2-ylquinolin-7-amine Chemical compound C=1C=C2C(OC)=CC=NC2=CC=1NC1=CC=CC=N1 GAWOGCFTXVIYQT-UHFFFAOYSA-N 0.000 claims description 8
- KQHZIQRXEWLDJA-UHFFFAOYSA-N 4-methyl-n-(4-methylpyridin-2-yl)quinolin-2-amine Chemical compound CC1=CC=NC(NC=2N=C3C=CC=CC3=C(C)C=2)=C1 KQHZIQRXEWLDJA-UHFFFAOYSA-N 0.000 claims description 8
- GHJMOXJEERLACS-UHFFFAOYSA-N 4-methyl-n-(5-nitropyridin-2-yl)quinolin-2-amine Chemical compound N=1C2=CC=CC=C2C(C)=CC=1NC1=CC=C([N+]([O-])=O)C=N1 GHJMOXJEERLACS-UHFFFAOYSA-N 0.000 claims description 8
- BICKHJDFQUBMDX-UHFFFAOYSA-N 4-methyl-n-(6-methylpyridin-2-yl)quinolin-2-amine Chemical compound CC1=CC=CC(NC=2N=C3C=CC=CC3=C(C)C=2)=N1 BICKHJDFQUBMDX-UHFFFAOYSA-N 0.000 claims description 8
- OCEOPRHNGQCGSQ-UHFFFAOYSA-N 4-methyl-n-[4-(trifluoromethoxy)phenyl]quinolin-2-amine Chemical compound N=1C2=CC=CC=C2C(C)=CC=1NC1=CC=C(OC(F)(F)F)C=C1 OCEOPRHNGQCGSQ-UHFFFAOYSA-N 0.000 claims description 8
- LFODQFOSXSMJRS-UHFFFAOYSA-N 4-methyl-n-[4-(trifluoromethoxy)phenyl]quinolin-2-amine;hydrochloride Chemical compound [Cl-].[NH+]=1C2=CC=CC=C2C(C)=CC=1NC1=CC=C(OC(F)(F)F)C=C1 LFODQFOSXSMJRS-UHFFFAOYSA-N 0.000 claims description 8
- WZMXBKQUZOMDOY-UHFFFAOYSA-N 4-methyl-n-pyrazin-2-ylquinolin-2-amine Chemical compound N=1C2=CC=CC=C2C(C)=CC=1NC1=CN=CC=N1 WZMXBKQUZOMDOY-UHFFFAOYSA-N 0.000 claims description 8
- ADHHGODRRRVYSR-UHFFFAOYSA-N 4-methyl-n-pyridin-2-ylquinolin-2-amine Chemical compound N=1C2=CC=CC=C2C(C)=CC=1NC1=CC=CC=N1 ADHHGODRRRVYSR-UHFFFAOYSA-N 0.000 claims description 8
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- HTXYLYNDCJUKPB-UHFFFAOYSA-N 4-morpholin-4-yl-n-[4-(trifluoromethoxy)phenyl]quinolin-7-amine Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC1=CC=C(C(=CC=N2)N3CCOCC3)C2=C1 HTXYLYNDCJUKPB-UHFFFAOYSA-N 0.000 claims description 8
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- FNRTZPDQMOKWEO-UHFFFAOYSA-N 4-n,4-n-dimethyl-7-n-(4-methylpyridin-2-yl)quinoline-4,7-diamine Chemical compound C=1C=C2C(N(C)C)=CC=NC2=CC=1NC1=CC(C)=CC=N1 FNRTZPDQMOKWEO-UHFFFAOYSA-N 0.000 claims description 8
- OWEYRQNNNZFLKZ-UHFFFAOYSA-N 4-n,4-n-dimethyl-7-n-[4-(trifluoromethoxy)phenyl]quinoline-4,7-diamine Chemical compound C=1C=C2C(N(C)C)=CC=NC2=CC=1NC1=CC=C(OC(F)(F)F)C=C1 OWEYRQNNNZFLKZ-UHFFFAOYSA-N 0.000 claims description 8
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- LHEPULDUSUAMAY-UHFFFAOYSA-N 6-(quinolin-2-ylamino)pyridine-3-carbonitrile Chemical compound N1=CC(C#N)=CC=C1NC1=CC=C(C=CC=C2)C2=N1 LHEPULDUSUAMAY-UHFFFAOYSA-N 0.000 claims description 8
- YTYBSSXNNMYTMP-UHFFFAOYSA-N 6-(quinolin-2-ylamino)pyridine-3-carbonitrile;hydrochloride Chemical compound [Cl-].[NH+]1=CC(C#N)=CC=C1NC1=CC=C(C=CC=C2)C2=N1 YTYBSSXNNMYTMP-UHFFFAOYSA-N 0.000 claims description 8
- YKAUOMYYVJQVGG-UHFFFAOYSA-N 6-(quinoxalin-2-ylamino)pyridine-3-carbonitrile Chemical compound N1=CC(C#N)=CC=C1NC1=CN=C(C=CC=C2)C2=N1 YKAUOMYYVJQVGG-UHFFFAOYSA-N 0.000 claims description 8
- VZZOWEGAADNEDX-UHFFFAOYSA-N 6-[(3-methylquinolin-2-yl)amino]pyridine-3-carbonitrile Chemical compound CC1=CC2=CC=CC=C2N=C1NC1=CC=C(C#N)C=N1 VZZOWEGAADNEDX-UHFFFAOYSA-N 0.000 claims description 8
- YZUSLURXWJRRKQ-UHFFFAOYSA-N 6-[(4-methylquinolin-2-yl)amino]pyridine-3-carbonitrile Chemical compound N=1C2=CC=CC=C2C(C)=CC=1NC1=CC=C(C#N)C=N1 YZUSLURXWJRRKQ-UHFFFAOYSA-N 0.000 claims description 8
- HYQKEYKCHFZSNV-UHFFFAOYSA-N 6-[(8-chloroquinolin-2-yl)amino]-2-methylpyridine-3-carbonitrile Chemical compound C1=C(C#N)C(C)=NC(NC=2N=C3C(Cl)=CC=CC3=CC=2)=C1 HYQKEYKCHFZSNV-UHFFFAOYSA-N 0.000 claims description 8
- NQUSIBMZMQGZJP-UHFFFAOYSA-N 6-[(8-chloroquinolin-2-yl)amino]pyridine-3-carbonitrile Chemical compound N1=C2C(Cl)=CC=CC2=CC=C1NC1=CC=C(C#N)C=N1 NQUSIBMZMQGZJP-UHFFFAOYSA-N 0.000 claims description 8
- YGTLRZXTQCCYGE-UHFFFAOYSA-N 6-chloro-n-(4-methylpyridin-2-yl)quinolin-2-amine Chemical compound CC1=CC=NC(NC=2N=C3C=CC(Cl)=CC3=CC=2)=C1 YGTLRZXTQCCYGE-UHFFFAOYSA-N 0.000 claims description 8
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- GSBHDTFVSXZRQJ-UHFFFAOYSA-N 6-chloro-n-(6-ethylpyridin-2-yl)quinolin-2-amine Chemical compound CCC1=CC=CC(NC=2N=C3C=CC(Cl)=CC3=CC=2)=N1 GSBHDTFVSXZRQJ-UHFFFAOYSA-N 0.000 claims description 8
- XTHMFTROJRWDRJ-UHFFFAOYSA-N 6-chloro-n-(6-methylpyridin-2-yl)quinolin-2-amine Chemical compound CC1=CC=CC(NC=2N=C3C=CC(Cl)=CC3=CC=2)=N1 XTHMFTROJRWDRJ-UHFFFAOYSA-N 0.000 claims description 8
- ABFXUMAJZGUCJM-UHFFFAOYSA-N 6-chloro-n-[4-(trifluoromethoxy)phenyl]quinolin-2-amine Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC1=CC=C(C=C(Cl)C=C2)C2=N1 ABFXUMAJZGUCJM-UHFFFAOYSA-N 0.000 claims description 8
- FOKFEEOICXUAED-UHFFFAOYSA-N 6-chloro-n-[5-(trifluoromethyl)pyridin-2-yl]quinolin-2-amine Chemical compound N1=CC(C(F)(F)F)=CC=C1NC1=CC=C(C=C(Cl)C=C2)C2=N1 FOKFEEOICXUAED-UHFFFAOYSA-N 0.000 claims description 8
- ZUSBYXKHPAAGKP-UHFFFAOYSA-N 6-chloro-n-pyrazin-2-ylquinolin-2-amine Chemical compound C1=CC2=CC(Cl)=CC=C2N=C1NC1=CN=CC=N1 ZUSBYXKHPAAGKP-UHFFFAOYSA-N 0.000 claims description 8
- ZRNNTAQMCOKIDY-UHFFFAOYSA-N 6-methyl-n-naphthalen-2-ylpyridin-2-amine Chemical compound CC1=CC=CC(NC=2C=C3C=CC=CC3=CC=2)=N1 ZRNNTAQMCOKIDY-UHFFFAOYSA-N 0.000 claims description 8
- KLDBYFPTUGYQSF-UHFFFAOYSA-N 8-bromo-n-(4-methylpyridin-2-yl)quinolin-2-amine Chemical compound CC1=CC=NC(NC=2N=C3C(Br)=CC=CC3=CC=2)=C1 KLDBYFPTUGYQSF-UHFFFAOYSA-N 0.000 claims description 8
- MLMZDTAOJFGGJT-UHFFFAOYSA-N 8-bromo-n-[4-(trifluoromethoxy)phenyl]quinolin-2-amine Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC1=CC=C(C=CC=C2Br)C2=N1 MLMZDTAOJFGGJT-UHFFFAOYSA-N 0.000 claims description 8
- IYLUIBBHBDWNTE-UHFFFAOYSA-N 8-bromo-n-pyrazin-2-ylquinolin-2-amine Chemical compound N1=C2C(Br)=CC=CC2=CC=C1NC1=CN=CC=N1 IYLUIBBHBDWNTE-UHFFFAOYSA-N 0.000 claims description 8
- RUURRABBFPPQTD-UHFFFAOYSA-N 8-chloro-n-(3-chloro-4-methoxyphenyl)quinolin-2-amine Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=CC=C(C=CC=C2Cl)C2=N1 RUURRABBFPPQTD-UHFFFAOYSA-N 0.000 claims description 8
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| TW202237119A (zh) | 2020-12-10 | 2022-10-01 | 美商住友製藥腫瘤公司 | Ａｌｋ﹘５抑制劑和彼之用途 |
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| WO2022247920A1 (zh) | 2021-05-27 | 2022-12-01 | 江苏恒瑞医药股份有限公司 | 喹啉胺类化合物、其制备方法及其在医药上的应用 |
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| FR2387229A1 (fr) | 1977-04-13 | 1978-11-10 | Anvar | Dipyrido (4,3-b) (3,4-f) indoles, procede d'obtention, application therapeutique et compositions pharmaceutiques les contenant |
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| FR2645861A1 (fr) | 1989-04-17 | 1990-10-19 | Inst Nat Sante Rech Med | Utilisation de dipyrido (4,3-b) (3,4-f) indoles pour la preparation de medicaments utiles pour le traitement du sida |
| US6177401B1 (en) | 1992-11-13 | 2001-01-23 | Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften | Use of organic compounds for the inhibition of Flk-1 mediated vasculogenesis and angiogenesis |
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| UA75055C2 (uk) | 1999-11-30 | 2006-03-15 | Пфайзер Продактс Інк. | Похідні бензоімідазолу, що використовуються як антипроліферативний засіб, фармацевтична композиція на їх основі |
| DE10013318A1 (de) | 2000-03-17 | 2001-09-20 | Merck Patent Gmbh | Formulierung enthaltend Chinoxalinderivate |
| WO2002074726A2 (en) | 2001-01-22 | 2002-09-26 | Memory Pharmaceuticals Corporation | Aniline derivatives useful as phosphodiesterase 4 inhibitors |
| JP2005531574A (ja) | 2002-05-22 | 2005-10-20 | アムジエン・インコーポレーテツド | 痛みの治療にバニロイド受容体リガンドとして使用するためのアミノ−ピリジン、−ピリジンおよびピリダジン誘導体 |
| AU2002950217A0 (en) | 2002-07-16 | 2002-09-12 | Prana Biotechnology Limited | 8- Hydroxy Quinoline Derivatives |
| MXPA05000827A (es) | 2002-07-19 | 2005-08-29 | Memory Pharm Corp | Inhibidores de fosfodiesterasa 4, incluyendo analogos de anilina y difenilamina n-sustituidos. |
| FR2849474B3 (fr) | 2002-12-27 | 2004-12-03 | Olivier Jean Noel Juin | Installation de transformation de l'energie cinetique d'un fluide en energie electrique |
| WO2004078731A1 (en) | 2003-03-06 | 2004-09-16 | 'chemical Diversity Research Institute', Ltd. | Quinoline-carboxylic acids and the derivatives thereof, a focused library |
| FR2859475A1 (fr) | 2003-09-04 | 2005-03-11 | Centre Nat Rech Scient | Utilisation de composes derives d'ellipticine et d'aza-ellipticine pour la preparation d'un medicament utile pour le traitement de maladies genetiques resultant de l'alteration des processus d'epissage |
| FR2859474B1 (fr) | 2003-09-04 | 2006-01-13 | Centre Nat Rech Scient | Utilisation de composes derives d'indole pour la preparation d'un medicament utile pour le traitement de maladies genetiques resultant de l'alteration des processus d'epissage |
| KR101190912B1 (ko) | 2003-11-19 | 2012-10-12 | 어레이 바이오파마 인크. | Ｍｅｋ의 헤테로시클릭 억제제 및 그의 사용 방법 |
| EP1853265B1 (en) | 2005-01-28 | 2016-01-27 | The Government of the United States of America as represented by the Secretary of the Department of Health and Human Services | Farnesyltransferase inhibitors for use in the treatment of laminopathies, cellular aging and atherosclerosis |
| FR2903312B1 (fr) | 2006-07-05 | 2008-09-26 | Univ Aix Marseille Ii | Utilisation d'inhibiteurs d'hmg-coa reductase et de farnesyl-pyrophosphate synthase dans la preparation d'un medicament |
| WO2008008234A1 (en) | 2006-07-07 | 2008-01-17 | Targegen, Inc. | 2-amino-5-substituted pyrimidine inhibitors |
| ES2547303T3 (es) | 2007-01-19 | 2015-10-05 | Ardea Biosciences, Inc. | Inhibidores de MEK |
| FR2912745A1 (fr) | 2007-02-19 | 2008-08-22 | Centre Nat Rech Scient | Nouveaux composes derives d'indole et compositions pharmaceutiques les contenant |
| US20100249184A1 (en) | 2007-03-16 | 2010-09-30 | Mount Sinai School Of Medicine | Induction and/or maintenance of tumor dormancy by disruption of urokinase plasminogen activator receptor-integrin interaction |
| US8222634B2 (en) | 2007-05-17 | 2012-07-17 | Lg Chem, Ltd. | Anthracene derivatives and organic electronic device using the same |
| WO2009023844A2 (en) | 2007-08-15 | 2009-02-19 | Memory Pharmaceuticals Corporation | 3' substituted compounds having 5-ht6 receptor affinity |
| WO2009029617A1 (en) | 2007-08-27 | 2009-03-05 | Kalypsys, Inc. | Diarylamine-substituted quinolones useful as inducible nitric oxide synthase inhibitors |
| FR2926297B1 (fr) | 2008-01-10 | 2013-03-08 | Centre Nat Rech Scient | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
| EP2266972A1 (en) * | 2009-06-12 | 2010-12-29 | Splicos | New chemical molecules that inhibit the splicing mechanism for treating diseases resulting from splicing anomalies |
| CN102625804B (zh) * | 2009-06-12 | 2015-04-08 | Abivax公司 | 用于治疗aids的化合物 |
| WO2010151755A2 (en) | 2009-06-25 | 2010-12-29 | The Brigham And Women's Hospital, Inc. | TREATMENT OF INFLAMMATORY DISEASES USING miR-124 |
| EP2465502A1 (en) | 2010-12-15 | 2012-06-20 | Société Splicos | Compounds useful for treating AIDS |
| US20150272959A1 (en) * | 2012-10-04 | 2015-10-01 | Oyagen, Inc. | Small molecules as anti-hiv agents that disrupt vif self-association and methods of use thereof |
| EP2757161A1 (en) * | 2013-01-17 | 2014-07-23 | Splicos | miRNA-124 as a biomarker of viral infection |
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2014
- 2014-07-04 CA CA2916623A patent/CA2916623C/en active Active
- 2014-07-04 HR HRP20211839TT patent/HRP20211839T1/hr unknown
- 2014-07-04 ES ES14758168T patent/ES2898385T3/es active Active
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- 2014-07-04 BR BR112016000127-3A patent/BR112016000127B1/pt active IP Right Grant
- 2014-07-04 KR KR1020167003323A patent/KR102326068B1/ko active Active
- 2014-07-04 WO PCT/IB2014/062849 patent/WO2015001518A1/en not_active Ceased
- 2014-07-04 CN CN201480038497.4A patent/CN105530938B/zh active Active
- 2014-07-04 PL PL14758168T patent/PL3016656T3/pl unknown
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- 2014-07-04 RU RU2016103217A patent/RU2681943C9/ru active
- 2014-07-04 EP EP14758168.0A patent/EP3016656B1/en active Active
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2019
- 2019-04-26 JP JP2019086240A patent/JP2019142946A/ja active Pending
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