JP2017510555A5 - - Google Patents
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- Publication number
- JP2017510555A5 JP2017510555A5 JP2016551815A JP2016551815A JP2017510555A5 JP 2017510555 A5 JP2017510555 A5 JP 2017510555A5 JP 2016551815 A JP2016551815 A JP 2016551815A JP 2016551815 A JP2016551815 A JP 2016551815A JP 2017510555 A5 JP2017510555 A5 JP 2017510555A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- phenylcyclopropyl
- piperidin
- alkyl
- azetidin
- 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 97
- 150000003839 salts Chemical class 0.000 claims 47
- 150000001875 compounds Chemical class 0.000 claims 40
- 125000003118 aryl group Chemical group 0.000 claims 29
- 125000005843 halogen group Chemical group 0.000 claims 28
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 27
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 25
- 125000001424 substituent group Chemical group 0.000 claims 21
- 229910052799 carbon Inorganic materials 0.000 claims 17
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 16
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 13
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 10
- -1 4-fluorophenylmethyl Chemical group 0.000 claims 9
- 125000005842 heteroatom Chemical group 0.000 claims 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 8
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 8
- 239000003814 drug Substances 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 3
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 150000001721 carbon Chemical group 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 2
- LRISLSZFPGTNFP-CFYLOBDVSA-N 2-[1-(4-hydroxycyclohexanecarbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound OC1CCC(CC1)C(=O)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 LRISLSZFPGTNFP-CFYLOBDVSA-N 0.000 claims 2
- LNKLCUWGJGYEJN-YRTVTSRJSA-N 2-[1-(4-hydroxycyclohexyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound OC1CCC(CC1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 LNKLCUWGJGYEJN-YRTVTSRJSA-N 0.000 claims 2
- WKZYPDVFDYESLQ-RBUKOAKNSA-N 2-[1-methylsulfonyl-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound CS(=O)(=O)N1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CC#N WKZYPDVFDYESLQ-RBUKOAKNSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 2
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 2
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 claims 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
- 208000032027 Essential Thrombocythemia Diseases 0.000 claims 2
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 2
- 208000033826 Promyelocytic Acute Leukemia Diseases 0.000 claims 2
- 208000017733 acquired polycythemia vera Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 2
- 201000005787 hematologic cancer Diseases 0.000 claims 2
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 2
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims 2
- 206010028537 myelofibrosis Diseases 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 208000037244 polycythemia vera Diseases 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 208000003476 primary myelofibrosis Diseases 0.000 claims 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- VWIIMFORTMBPLN-UHFFFAOYSA-N 1-phenyl-4-[3-[[(2-phenylcyclopropyl)amino]methyl]azetidin-1-yl]cyclohexane-1-carbonitrile Chemical compound N#CC1(CCC(CC1)N1CC(CNC2CC2c2ccccc2)C1)c1ccccc1 VWIIMFORTMBPLN-UHFFFAOYSA-N 0.000 claims 1
- TVDKZBASXPLLBZ-FOIFJWKZSA-N 2-[1-(1-hydroxycyclopentanecarbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound OC1(CCCC1)C(=O)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 TVDKZBASXPLLBZ-FOIFJWKZSA-N 0.000 claims 1
- WNSIQTHQNNHKOU-GFOWMXPYSA-N 2-[1-(1-hydroxycyclopropanecarbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound OC1(CC1)C(=O)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 WNSIQTHQNNHKOU-GFOWMXPYSA-N 0.000 claims 1
- YSIRGVBHKRVSKU-FOIFJWKZSA-N 2-[1-(1-methylpyrazol-4-yl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound Cn1cc(cn1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 YSIRGVBHKRVSKU-FOIFJWKZSA-N 0.000 claims 1
- FTXZQOUPDXBLHA-FCHUYYIVSA-N 2-[1-(1-methylpyrazol-4-yl)sulfonyl-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound CN1N=CC(=C1)S(=O)(=O)N1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CC#N FTXZQOUPDXBLHA-FCHUYYIVSA-N 0.000 claims 1
- BBEZPWPHOQIEGI-FCHUYYIVSA-N 2-[1-(1-methylpyrazole-4-carbonyl)-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound CN1N=CC(=C1)C(=O)N1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CC#N BBEZPWPHOQIEGI-FCHUYYIVSA-N 0.000 claims 1
- XEDHJJBMYHJZND-UHFFFAOYSA-N 2-[1-(2-fluorobenzoyl)-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound Fc1ccccc1C(=O)N1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1 XEDHJJBMYHJZND-UHFFFAOYSA-N 0.000 claims 1
- YGKRJKSCOHXOOF-GFOWMXPYSA-N 2-[1-(2-hydroxyethyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound OCCN1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 YGKRJKSCOHXOOF-GFOWMXPYSA-N 0.000 claims 1
- NQZHVXXBZTZCFM-LEWJYISDSA-N 2-[1-(2-methylpyrazole-3-carbonyl)-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound CN1N=CC=C1C(=O)N1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CC#N NQZHVXXBZTZCFM-LEWJYISDSA-N 0.000 claims 1
- MJPVZDXQCTUQIG-UHFFFAOYSA-N 2-[1-(3,5-difluorobenzoyl)-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound Fc1cc(F)cc(c1)C(=O)N1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1 MJPVZDXQCTUQIG-UHFFFAOYSA-N 0.000 claims 1
- JHBCJWXVGNIDCD-UHFFFAOYSA-N 2-[1-(3-fluorobenzoyl)-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound Fc1cccc(c1)C(=O)N1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1 JHBCJWXVGNIDCD-UHFFFAOYSA-N 0.000 claims 1
- ZPVKWJUILDIPIU-BPGUCPLFSA-N 2-[1-(3-hydroxyazetidine-1-carbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound OC1CN(C1)C(=O)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 ZPVKWJUILDIPIU-BPGUCPLFSA-N 0.000 claims 1
- PPOYSOLYFOBOFP-YMOXTTMHSA-N 2-[1-(3-hydroxycyclobutyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound OC1CC(C1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 PPOYSOLYFOBOFP-YMOXTTMHSA-N 0.000 claims 1
- QEODSRKCBHJXGW-UHFFFAOYSA-N 2-[1-(4-fluorobenzoyl)-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound Fc1ccc(cc1)C(=O)N1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1 QEODSRKCBHJXGW-UHFFFAOYSA-N 0.000 claims 1
- BSGNTEOUVKIDEX-UHFFFAOYSA-N 2-[1-(4-fluorobenzoyl)-4-[3-[[(2-phenylcyclopropyl)amino]methyl]azetidin-1-yl]piperidin-4-yl]acetonitrile Chemical compound Fc1ccc(cc1)C(=O)N1CCC(CC#N)(CC1)N1CC(CNC2CC2c2ccccc2)C1 BSGNTEOUVKIDEX-UHFFFAOYSA-N 0.000 claims 1
- CFEZGDDEXODSOP-OZAIVSQSSA-N 2-[1-(4-hydroxypiperidine-1-carbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound OC1CCN(CC1)C(=O)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 CFEZGDDEXODSOP-OZAIVSQSSA-N 0.000 claims 1
- JDOVUIRQPWAANN-XMMISQBUSA-N 2-[1-(4-methoxypiperidine-1-carbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound COC1CCN(CC1)C(=O)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 JDOVUIRQPWAANN-XMMISQBUSA-N 0.000 claims 1
- MOKIPZSEHIRCHU-UHFFFAOYSA-N 2-[1-(benzenesulfonyl)-4-[3-[[(2-phenylcyclopropyl)amino]methyl]azetidin-1-yl]piperidin-4-yl]acetonitrile Chemical compound O=S(=O)(N1CCC(CC#N)(CC1)N1CC(CNC2CC2c2ccccc2)C1)c1ccccc1 MOKIPZSEHIRCHU-UHFFFAOYSA-N 0.000 claims 1
- KQQSUVAYFVDCOX-XZOQPEGZSA-N 2-[1-(cyclopropylmethyl)-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]-N,N-dimethylacetamide Chemical compound C1(CC1)CN1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CC(=O)N(C)C KQQSUVAYFVDCOX-XZOQPEGZSA-N 0.000 claims 1
- POXDXBWDCJXXQK-FCHUYYIVSA-N 2-[1-(cyclopropylmethyl)-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]-N-methylacetamide Chemical compound C1(CC1)CN1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CC(=O)NC POXDXBWDCJXXQK-FCHUYYIVSA-N 0.000 claims 1
- GOBGZDUAYFOHAB-FOIFJWKZSA-N 2-[1-(morpholine-4-carbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound O=C(N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1)N1CCOCC1 GOBGZDUAYFOHAB-FOIFJWKZSA-N 0.000 claims 1
- SRPFBOAHKKBKKR-OZAIVSQSSA-N 2-[1-(oxan-4-yl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound N#CCC1(CN(C1)C1CCOCC1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 SRPFBOAHKKBKKR-OZAIVSQSSA-N 0.000 claims 1
- FXFHNEHARADBNL-JTGIGXABSA-N 2-[1-(oxolan-3-yl)-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1(=CC=CC=C1)[C@H]1[C@@H](C1)NC1CCN(CC1)C1(CN(C1)C1COCC1)CC#N FXFHNEHARADBNL-JTGIGXABSA-N 0.000 claims 1
- BMNSVVYABBFIOM-ATKRNPRHSA-N 2-[1-(oxolane-2-carbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound O=C(C1CCCO1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 BMNSVVYABBFIOM-ATKRNPRHSA-N 0.000 claims 1
- PNLVAMICRIAANP-KITAHSCOSA-N 2-[1-(oxolane-3-carbonyl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound O=C(C1CCOC1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 PNLVAMICRIAANP-KITAHSCOSA-N 0.000 claims 1
- BMNSVVYABBFIOM-HRUVVLKGSA-N 2-[1-[(2R)-oxolane-2-carbonyl]-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound O=C([C@H]1CCCO1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 BMNSVVYABBFIOM-HRUVVLKGSA-N 0.000 claims 1
- BMNSVVYABBFIOM-PDQYLBCOSA-N 2-[1-[(2S)-oxolane-2-carbonyl]-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound O=C([C@@H]1CCCO1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 BMNSVVYABBFIOM-PDQYLBCOSA-N 0.000 claims 1
- PNLVAMICRIAANP-PSQUCKQXSA-N 2-[1-[(3R)-oxolane-3-carbonyl]-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound O=C([C@@H]1CCOC1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 PNLVAMICRIAANP-PSQUCKQXSA-N 0.000 claims 1
- PNLVAMICRIAANP-KFEBLCFASA-N 2-[1-[(3S)-oxolane-3-carbonyl]-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound O=C([C@H]1CCOC1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 PNLVAMICRIAANP-KFEBLCFASA-N 0.000 claims 1
- NYIWGYPPKJPGTJ-GFOWMXPYSA-N 2-[1-[4-(methoxymethyl)-4-[[[(1R)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]cyclobutyl]acetic acid Chemical compound COCC1(CN[C@@H]2CC2c2ccccc2)CCN(CC1)C1(CC(O)=O)CCC1 NYIWGYPPKJPGTJ-GFOWMXPYSA-N 0.000 claims 1
- GHEGXJMODHODMQ-UHFFFAOYSA-N 2-[1-[4-[(2-phenylcyclopropyl)amino]piperidin-1-yl]cyclobutyl]acetonitrile Chemical compound N#CCC1(CCC1)N1CCC(CC1)NC1CC1c1ccccc1 GHEGXJMODHODMQ-UHFFFAOYSA-N 0.000 claims 1
- INRMDSMOHQTQSG-WUBHUQEYSA-N 2-[1-[4-[(4-fluorophenyl)methyl]-4-[[[(1R)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]cyclobutyl]acetic acid Chemical compound OC(=O)CC1(CCC1)N1CCC(CN[C@@H]2CC2c2ccccc2)(Cc2ccc(F)cc2)CC1 INRMDSMOHQTQSG-WUBHUQEYSA-N 0.000 claims 1
- RRYIYTAJBSSOPL-UHFFFAOYSA-N 2-[1-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]cyclobutyl]acetonitrile Chemical compound N#CCC1(CCC1)N1CCC(CNC2CC2c2ccccc2)CC1 RRYIYTAJBSSOPL-UHFFFAOYSA-N 0.000 claims 1
- ATMPNNXKBAQDJV-MUMRKEEXSA-N 2-[1-[4-[[[(1R)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]cyclobutyl]acetic acid Chemical compound OC(=O)CC1(CCC1)N1CCC(CN[C@@H]2CC2c2ccccc2)CC1 ATMPNNXKBAQDJV-MUMRKEEXSA-N 0.000 claims 1
- ZQLIYVSBBTXGFL-RBUKOAKNSA-N 2-[1-[4-methyl-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]cyclobutyl]acetic acid Chemical compound CC1(CCN(CC1)C1(CCC1)CC(=O)O)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 ZQLIYVSBBTXGFL-RBUKOAKNSA-N 0.000 claims 1
- CHLWPXFUYDMJHJ-VQTJNVASSA-N 2-[1-acetyl-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound C(C)(=O)N1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CC#N CHLWPXFUYDMJHJ-VQTJNVASSA-N 0.000 claims 1
- JIGFNRMEKAMQDW-LEWJYISDSA-N 2-[1-acetyl-4-[3-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]azetidin-1-yl]piperidin-4-yl]acetonitrile Chemical compound C(C)(=O)N1CCC(CC1)(N1CC(C1)CN[C@H]1[C@@H](C1)C1=CC=CC=C1)CC#N JIGFNRMEKAMQDW-LEWJYISDSA-N 0.000 claims 1
- QXXWMQDZVMZJOV-BJKOFHAPSA-N 2-[1-benzoyl-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound C(C1=CC=CC=C1)(=O)N1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CC#N QXXWMQDZVMZJOV-BJKOFHAPSA-N 0.000 claims 1
- DYHJMPPSZFIVIQ-UHFFFAOYSA-N 2-[1-benzoyl-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound O=C(N1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1)c1ccccc1 DYHJMPPSZFIVIQ-UHFFFAOYSA-N 0.000 claims 1
- YIVORPSROJSZLH-LOSJGSFVSA-N 2-[1-benzyl-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound C(C1=CC=CC=C1)N1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CC#N YIVORPSROJSZLH-LOSJGSFVSA-N 0.000 claims 1
- CBQUUHSDOMDECC-MUMRKEEXSA-N 2-[1-ethyl-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetic acid Chemical compound CCN1CC(CC(O)=O)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 CBQUUHSDOMDECC-MUMRKEEXSA-N 0.000 claims 1
- FHJDCJOIHQMOKO-GFOWMXPYSA-N 2-[1-ethylsulfonyl-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]-N-methylacetamide Chemical compound CCS(=O)(=O)N1CC(CC(=O)NC)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 FHJDCJOIHQMOKO-GFOWMXPYSA-N 0.000 claims 1
- UOUIRRWHFRPORZ-GFOWMXPYSA-N 2-[1-ethylsulfonyl-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound CCS(=O)(=O)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 UOUIRRWHFRPORZ-GFOWMXPYSA-N 0.000 claims 1
- NKPUMNAEPKDNKZ-GFOWMXPYSA-N 2-[1-ethylsulfonyl-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]ethanol Chemical compound CCS(=O)(=O)N1CC(CCO)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 NKPUMNAEPKDNKZ-GFOWMXPYSA-N 0.000 claims 1
- OSXJNKWWLVSYHK-LEWJYISDSA-N 2-[1-ethylsulfonyl-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]-N,N-dimethylacetamide Chemical compound C(C)S(=O)(=O)N1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CC(=O)N(C)C OSXJNKWWLVSYHK-LEWJYISDSA-N 0.000 claims 1
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201613860A (en) | 2014-02-13 | 2016-04-16 | Incyte Corp | Cyclopropylamines as LSD1 inhibitors |
| US9346776B2 (en) | 2014-02-13 | 2016-05-24 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compound |
| PL3105218T3 (pl) | 2014-02-13 | 2020-03-31 | Incyte Corporation | Cyklopropyloaminy jako inhibitory lsd1 |
| LT3105226T (lt) | 2014-02-13 | 2019-11-11 | Incyte Corp | Ciklopropilaminai, kaip lsd1 inhibitoriai |
| US9428470B2 (en) | 2014-02-13 | 2016-08-30 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| US9527835B2 (en) | 2014-02-13 | 2016-12-27 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| US9695180B2 (en) | 2014-07-10 | 2017-07-04 | Incyte Corporation | Substituted imidazo[1,2-a]pyrazines as LSD1 inhibitors |
| WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| TWI687419B (zh) | 2014-07-10 | 2020-03-11 | 美商英塞特公司 | 作為ｌｓｄ１抑制劑之咪唑并吡啶及咪唑并吡嗪 |
| US9758523B2 (en) | 2014-07-10 | 2017-09-12 | Incyte Corporation | Triazolopyridines and triazolopyrazines as LSD1 inhibitors |
| EP3277689B1 (en) | 2015-04-03 | 2019-09-04 | Incyte Corporation | Heterocyclic compounds as lsd1 inhibitors |
| CN107849611A (zh) | 2015-06-12 | 2018-03-27 | 奥瑞泽恩基因组学股份有限公司 | 与lsd1抑制剂相关的生物标志物及其用途 |
| WO2017013061A1 (en) | 2015-07-17 | 2017-01-26 | Oryzon Genomics, S.A. | Biomarkers associated with lsd1 inhibitors and uses thereof |
| KR102710120B1 (ko) | 2015-08-12 | 2024-09-27 | 인사이트 홀딩스 코포레이션 | Lsd1 저해제의 염 |
| US10059668B2 (en) | 2015-11-05 | 2018-08-28 | Mirati Therapeutics, Inc. | LSD1 inhibitors |
| US9809541B2 (en) | 2015-12-29 | 2017-11-07 | Mirati Therapeutics, Inc. | LSD1 inhibitors |
| MY199967A (en) | 2016-03-15 | 2023-11-30 | Oryzon Genomics Sa | Combinations of lsd1 inhibitors for use in the treatment of solid tumors |
| CN107200706A (zh) * | 2016-03-16 | 2017-09-26 | 中国科学院上海药物研究所 | 一类氟取代的环丙胺类化合物及其制备方法、药物组合物和用途 |
| ES3042059T3 (en) | 2016-03-16 | 2025-11-18 | Oryzon Genomics Sa | Methods to determine kdm1a target engagement and chemoprobes useful therefor |
| WO2017184934A1 (en) | 2016-04-22 | 2017-10-26 | Incyte Corporation | Formulations of an lsd1 inhibitor |
| CN107459476B (zh) * | 2016-06-03 | 2022-06-24 | 中国科学院上海药物研究所 | 反吲哚啉环丙胺类化合物及其制备方法、药物组合物和用途 |
| US20190256930A1 (en) | 2016-11-03 | 2019-08-22 | Oryzon Genomics, S.A. | Biomarkers for determining responsiveness to lsd1 inhibitors |
| US20190256929A1 (en) | 2016-11-03 | 2019-08-22 | Oryzon Genomics, S.A. | Pharmacodynamic biomarkers for personalized cancer care using epigenetic modifying agents |
| US11168082B2 (en) | 2017-05-15 | 2021-11-09 | The Regents Of The University Of Michigan | Pyrrolo[2,3-C]pyridines and related analogs as LSD-1 inhibitors |
| CN110996949A (zh) | 2017-08-03 | 2020-04-10 | 奥瑞泽恩基因组学股份有限公司 | 用于治疗行为改变的方法 |
| WO2019068326A1 (en) | 2017-10-05 | 2019-04-11 | Université D'aix-Marseille | INHIBITORS OF LSD1 FOR THE TREATMENT AND PREVENTION OF CARDIOMYOPATHIES |
| US11944614B2 (en) | 2018-05-15 | 2024-04-02 | Regents Of The University Of Michigan | Imidazo[4,5-c]pyridine compounds as LSD-1 inhibitors |
| WO2020047198A1 (en) | 2018-08-31 | 2020-03-05 | Incyte Corporation | Salts of an lsd1 inhibitor and processes for preparing the same |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| RS67485B1 (sr) | 2019-03-20 | 2025-12-31 | Oryzon Genomics Sa | Postupci lečenja poremećaja pažnje sa hiperaktivnošću korišćenjem inhibitora kdm1a kao što je jedinjenje vafidemstat |
| EP4670795A2 (en) | 2019-03-20 | 2025-12-31 | Oryzon Genomics, S.A. | TREATMENT METHODS FOR BORDERLINE PERSONALITY DISORDER |
| CN114341366A (zh) | 2019-07-05 | 2022-04-12 | 奥莱松基因组股份有限公司 | 用于使用kdm1a抑制剂个体化治疗小细胞肺癌的生物标志物和方法 |
| EP3964204A1 (en) | 2020-09-08 | 2022-03-09 | Université d'Aix-Marseille | Lsd1 inhibitors for use in the treatment and prevention of fibrosis of tissues |
| US20250073232A1 (en) | 2021-04-08 | 2025-03-06 | Oryzon Genomics, S.A. | Combinations of lsd1 inhibitors for treating myeloid cancers |
| US20250295660A1 (en) | 2022-05-09 | 2025-09-25 | Oryzon Genomics, S.A. | Methods of treating nf1-mutant tumors using lsd1 inhibitors |
| US20250275969A1 (en) | 2022-05-09 | 2025-09-04 | Oryzon Genomics, S.A. | Methods of treating malignant peripheral nerve sheath tumor (mpnst) using lsd1 inhibitors |
| CN120529900A (zh) | 2022-11-24 | 2025-08-22 | 奥莱松基因组股份有限公司 | 用于治疗癌症的LSD1抑制剂和Menin抑制剂的组合 |
| AU2024265078A1 (en) | 2023-05-04 | 2025-12-11 | Revolution Medicines, Inc. | Combination therapy for a ras related disease or disorder |
| US20250049810A1 (en) | 2023-08-07 | 2025-02-13 | Revolution Medicines, Inc. | Methods of treating a ras protein-related disease or disorder |
| CN117164465B (zh) * | 2023-09-04 | 2025-07-01 | 郑州大学 | 一种苯基环丙胺类化合物及其制备方法和应用 |
| US20250154171A1 (en) | 2023-10-12 | 2025-05-15 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2025171296A1 (en) | 2024-02-09 | 2025-08-14 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2025240847A1 (en) | 2024-05-17 | 2025-11-20 | Revolution Medicines, Inc. | Ras inhibitors |
| US20250375445A1 (en) | 2024-06-07 | 2025-12-11 | Revolution Medicines, Inc. | Methods of treating a ras protein-related disease or disorder |
| WO2025265060A1 (en) | 2024-06-21 | 2025-12-26 | Revolution Medicines, Inc. | Therapeutic compositions and methods for managing treatment-related effects |
| WO2026006747A1 (en) | 2024-06-28 | 2026-01-02 | Revolution Medicines, Inc. | Ras inhibitors |
Family Cites Families (316)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7013068A (enExample) | 1969-09-17 | 1971-03-19 | ||
| US4537889A (en) | 1982-12-27 | 1985-08-27 | Eli Lilly And Company | Inotropic agents |
| US4625040A (en) | 1984-09-24 | 1986-11-25 | Pennwalt Corporation | N-(phenyl) or N-(phenylcyclopropyl)-2,5-dihydro-2-oxo-4[(substituted phenyl)amino]-3-furancarboxamide derivatives |
| US4614810A (en) | 1984-09-24 | 1986-09-30 | Pennwalt Corporation | 4,5-dihydro-4-oxo-2-[(2-trans-phenylcyclopropyl)amino]-3-furancarboxylic acids and derivatives thereof |
| FR2607813B1 (fr) | 1986-12-05 | 1989-03-31 | Montpellier I Universite | Alkylamino-8 imidazo (1,2-a) pyrazines et derives, leur preparation et leur application en therapeutique |
| JPH032778Y2 (enExample) | 1986-12-15 | 1991-01-24 | ||
| AU622330B2 (en) | 1989-06-23 | 1992-04-02 | Takeda Chemical Industries Ltd. | Condensed heterocyclic compounds having a nitrogen atom in the bridgehead for use as fungicides |
| JP2844351B2 (ja) | 1989-07-13 | 1999-01-06 | 株式会社科薬 | 安定なポリミキシン系抗生物質水性溶液 |
| IL96432A0 (en) | 1989-11-30 | 1991-08-16 | Schering Ag | Pesticidal compositions containing pyridine derivatives and novel pyridine derivatives |
| FR2662163A1 (fr) | 1990-05-16 | 1991-11-22 | Lipha | Nouvelles 8-amino-1,2,4-triazolo(4,3-a) pyrazines, procedes de preparation et medicaments les contenant. |
| ES2130269T3 (es) | 1992-06-17 | 1999-07-01 | Upjohn Co | Oximas sustituidas con piridina, pirrolidina y azepina utiles como agentes contra la aterosclerosis y antihipercolesterolemicos. |
| JP2923139B2 (ja) | 1992-10-05 | 1999-07-26 | 三井化学株式会社 | 製 剤 |
| DE4327027A1 (de) | 1993-02-15 | 1994-08-18 | Bayer Ag | Imidazoazine |
| FR2711993B1 (fr) | 1993-11-05 | 1995-12-01 | Rhone Poulenc Rorer Sa | Médicaments contenant des dérivés de 7H-imidazol[1,2-a]pyrazine-8-one, les nouveaux composés et leur préparation. |
| US5932223A (en) | 1996-09-26 | 1999-08-03 | Merck & Co., Inc. | Rotavirus vaccine formulations |
| WO1999024434A1 (en) | 1997-11-11 | 1999-05-20 | Ono Pharmaceutical Co., Ltd. | Fused pyrazine compounds |
| JP2000319277A (ja) | 1999-05-11 | 2000-11-21 | Ono Pharmaceut Co Ltd | 縮合ピラジン化合物およびその化合物を有効成分とする薬剤 |
| JP2000319278A (ja) | 1999-05-11 | 2000-11-21 | Ono Pharmaceut Co Ltd | 縮合ピラジン化合物およびその化合物を有効成分とする薬剤 |
| JP4032566B2 (ja) | 1999-06-21 | 2008-01-16 | 東レ株式会社 | 発光素子 |
| JP4041624B2 (ja) | 1999-07-21 | 2008-01-30 | 三井化学株式会社 | 有機電界発光素子 |
| JP2001057292A (ja) | 1999-08-20 | 2001-02-27 | Toray Ind Inc | 発光素子 |
| CN1399543A (zh) | 1999-09-28 | 2003-02-26 | 灵药生物技术有限公司 | 含有尼美舒利的控释组合物 |
| SE9903611D0 (sv) | 1999-10-06 | 1999-10-06 | Astra Ab | Novel compounds III |
| DE19948434A1 (de) | 1999-10-08 | 2001-06-07 | Gruenenthal Gmbh | Substanzbibliothek enthaltend bicyclische Imidazo-5-amine und/oder bicyclische Imidazo-3-amine |
| JP4409680B2 (ja) | 1999-10-18 | 2010-02-03 | 株式会社ヤクルト本社 | 三環性縮合イミダゾール誘導体 |
| EP1277754B8 (en) | 2000-04-27 | 2005-09-28 | Astellas Pharma Inc. | Imidazopyridine derivatives |
| US6403588B1 (en) | 2000-04-27 | 2002-06-11 | Yamanouchi Pharmaceutical Co., Ltd. | Imidazopyridine derivatives |
| HU230396B1 (hu) | 2000-06-28 | 2016-04-28 | Smithkline Beecham Plc | Nedves őrlési eljárás |
| AR029538A1 (es) | 2000-07-06 | 2003-07-02 | Wyeth Corp | Composiciones farmaceuticas de agentes estrogenicos |
| EP1301511A2 (en) | 2000-07-14 | 2003-04-16 | Bristol-Myers Squibb Pharma Company | IMIDAZO 1,2-a]PYRAZINES FOR THE TREATMENT OF NEUROLOGICAL DISORDERS |
| DE10050663A1 (de) | 2000-10-13 | 2002-04-18 | Gruenenthal Gmbh | Verwendung von substituierten Imidazo[1,2-a]pyridin-, -pyrimidin- und pyrazin-3-yl-amin-Derivaten zur Herstellung von Medikamenten zur NOS-Inhibierung |
| WO2002034748A1 (fr) | 2000-10-24 | 2002-05-02 | Sankyo Company, Limited | Derives d'imidazopyridine |
| JP2002205992A (ja) | 2000-11-08 | 2002-07-23 | Takeda Chem Ind Ltd | 二環式トリアゾロン誘導体およびそれを含有する除草剤 |
| US6936608B2 (en) | 2000-11-10 | 2005-08-30 | Merck Sharp & Dohme Ltd. | Imidazo-triazine derivatives as ligands for GABA receptors |
| EP1343785A2 (de) | 2000-12-13 | 2003-09-17 | Basf Aktiengesellschaft | Verwendung von substituierten imidazoazinen, neue imidazoazine, verfahren zu deren herstellung, sowie sie enthaltende mittel |
| EP1217000A1 (en) | 2000-12-23 | 2002-06-26 | Aventis Pharma Deutschland GmbH | Inhibitors of factor Xa and factor VIIa |
| TWI312347B (en) | 2001-02-08 | 2009-07-21 | Eisai R&D Man Co Ltd | Bicyclic nitrogen-containing condensed ring compounds |
| WO2002072549A1 (en) | 2001-03-12 | 2002-09-19 | Millennium Pharmaceuticals, Inc. | Functionalized heterocycles as modulators of chemokine receptor function and methods of use therefor |
| AR035543A1 (es) | 2001-06-26 | 2004-06-16 | Japan Tobacco Inc | Agente terapeutico para la hepatitis c que comprende un compuesto de anillo condensado, compuesto de anillo condensado, composicion farmaceutica que lo comprende, compuestos de benzimidazol, tiazol y bifenilo utiles como intermediarios para producir dichos compuestos, uso del compuesto de anillo con |
| IL159811A0 (en) | 2001-07-13 | 2004-06-20 | Neurogen Corp | Heteroaryl substituted fused bicyclic heteroaryl compounds as gabaa receptor ligands |
| US6921762B2 (en) | 2001-11-16 | 2005-07-26 | Amgen Inc. | Substituted indolizine-like compounds and methods of use |
| US20050113283A1 (en) | 2002-01-18 | 2005-05-26 | David Solow-Cordero | Methods of treating conditions associated with an EDG-4 receptor |
| JP2005519915A (ja) | 2002-01-18 | 2005-07-07 | セレテック・リミテッド・ライアビリティ・カンパニー | Ｅｄｇ受容体に関連する症状の処置方法 |
| AU2003255845A1 (en) | 2002-08-22 | 2004-03-11 | Piramed Limited | Phosphadidylinositol 3,5-biphosphate inhibitors as anti-viral agents |
| UA80296C2 (en) | 2002-09-06 | 2007-09-10 | Biogen Inc | Imidazolopyridines and methods of making and using the same |
| US20060276339A1 (en) | 2002-10-16 | 2006-12-07 | Windsor J B | Methods and compositions for increasing the efficacy of biologically-active ingredients |
| EP1572693A1 (en) | 2002-12-20 | 2005-09-14 | Pharmacia Corporation | Mitogen activated protein kinase-activated protein kinase-2 inhibiting compounds |
| US7189723B2 (en) | 2003-02-10 | 2007-03-13 | Cgi Pharmaceuticals, Inc. | Certain 8-heteroaryl-6-phenyl-imidazo[1,2-a]pyrazines as modulators of kinase activity |
| US7157460B2 (en) | 2003-02-20 | 2007-01-02 | Sugen Inc. | Use of 8-amino-aryl-substituted imidazopyrazines as kinase inhibitors |
| GB0303910D0 (en) | 2003-02-20 | 2003-03-26 | Merck Sharp & Dohme | Therapeutic agents |
| US7186832B2 (en) | 2003-02-20 | 2007-03-06 | Sugen Inc. | Use of 8-amino-aryl-substituted imidazopyrazines as kinase inhibitors |
| EP2385040A1 (en) | 2003-03-14 | 2011-11-09 | ONO Pharmaceutical Co., Ltd. | Nitrogen-containing heterocyclic derivatives and drugs containing the same as the active ingredient |
| ES2338656T3 (es) | 2003-04-11 | 2010-05-11 | High Point Pharmaceuticals, Llc | Uso farmaceutico de 1,2,4-triazoles fusionados. |
| JP2006522750A (ja) | 2003-04-11 | 2006-10-05 | ノボ ノルディスク アクティーゼルスカブ | 代謝性症候群ならびに関連の疾患および障害を治療するために、１１β−ヒドロキシステロイドデヒドロゲナーゼ１型阻害剤および抗高血圧剤を使用する併用療法 |
| CA2522431A1 (en) | 2003-04-24 | 2004-11-11 | Merck & Co., Inc. | Inhibitors of akt activity |
| SE0301653D0 (sv) | 2003-06-05 | 2003-06-05 | Astrazeneca Ab | Novel compounds |
| KR20060056944A (ko) | 2003-07-14 | 2006-05-25 | 아레나 파마슈티칼스, 인크. | 대사 조절제로서 융합된 아릴 및 헤테로아릴 유도체 및이에 관련된 장애의 예방 또는 치료 |
| US7538120B2 (en) | 2003-09-03 | 2009-05-26 | Array Biopharma Inc. | Method of treating inflammatory diseases |
| JP4870562B2 (ja) | 2003-09-12 | 2012-02-08 | メルク セローノ ソシエテ アノニム | 糖尿病の治療のためのスルホンアミド誘導体 |
| JP2005089352A (ja) | 2003-09-16 | 2005-04-07 | Kissei Pharmaceut Co Ltd | 新規なイミダゾ［１，５−ａ］ピラジン誘導体、それを含有する医薬組成物およびそれらの用途 |
| BRPI0415185A (pt) | 2003-10-10 | 2006-11-28 | Pfizer Prod Inc | 2h-[1,2,4]triazol[4,3-a]pirazinas substituìdas como inibidores da gsk-3 |
| US7419978B2 (en) | 2003-10-22 | 2008-09-02 | Bristol-Myers Squibb Company | Phenyl-aniline substituted bicyclic compounds useful as kinase inhibitors |
| US7714009B2 (en) | 2003-10-31 | 2010-05-11 | Takeda Pharmaceutical Company Limited | Nitrogen-containing fused heterocyclic compounds |
| JPWO2005063241A1 (ja) | 2003-12-26 | 2007-07-19 | 小野薬品工業株式会社 | ミトコンドリアベンゾジアゼピン受容体介在性疾患の予防および／または治療剤 |
| WO2005077948A1 (ja) | 2004-02-16 | 2005-08-25 | Daiichi Pharmaceutical Co., Ltd. | 抗真菌作用複素環化合物 |
| US7306631B2 (en) | 2004-03-30 | 2007-12-11 | The Procter & Gamble Company | Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof |
| CA2564356A1 (en) * | 2004-04-26 | 2005-11-03 | Pfizer Inc. | Pyrrolopyridine derivatives and their use as hiv-integrase inhibitors |
| EP1758557B1 (en) | 2004-05-11 | 2011-07-13 | Egalet Ltd. | Swellable dosage form comprising gellan gum |
| TW200612918A (en) | 2004-07-29 | 2006-05-01 | Threshold Pharmaceuticals Inc | Lonidamine analogs |
| JP2008509985A (ja) | 2004-08-18 | 2008-04-03 | ファルマシア アンド アップジョン カンパニー リミテッド ライアビリティ カンパニー | 炎症治療用の新規トリアゾロピリジン化合物 |
| EP1799671A4 (en) | 2004-09-02 | 2009-06-10 | Smithkline Beecham Corp | CHEMICAL COMPOUNDS |
| WO2006038116A2 (en) | 2004-10-07 | 2006-04-13 | Warner-Lambert Company Llc | Triazolopyridine derivatives as antibacterial agents |
| JP2008520719A (ja) | 2004-11-22 | 2008-06-19 | スレショルド ファーマシューティカルズ インコーポレイティッド | チューブリン結合抗癌剤およびそれらのプロドラッグ |
| WO2006058752A1 (en) | 2004-12-01 | 2006-06-08 | Laboratoires Serono S.A. | [1,2,4]triazolo[4,3-a]pyridine derivatives for the treatment of hyperproliferative diseases |
| WO2006073938A2 (en) | 2004-12-30 | 2006-07-13 | East Carolina University | Method for the synthesis of 3-substituted indolizine and benzoindolizine compounds |
| US7456289B2 (en) | 2004-12-31 | 2008-11-25 | National Health Research Institutes | Anti-tumor compounds |
| MX2007010139A (es) | 2005-02-22 | 2007-09-27 | Pfizer | Derivados de oxiindol como agonista del receptor 5ht4. |
| ITBO20050123A1 (it) | 2005-03-07 | 2005-06-06 | Alfa Wassermann Spa | Formulazioni farmaceutiche gastroresistenti contenenti rifaximina |
| EP1871762A2 (en) | 2005-04-18 | 2008-01-02 | Neurogen Corporation | Subtituted heteroaryl cb1 antagonists |
| US7579360B2 (en) | 2005-06-09 | 2009-08-25 | Bristol-Myers Squibb Company | Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| US7572807B2 (en) | 2005-06-09 | 2009-08-11 | Bristol-Myers Squibb Company | Heteroaryl 11-beta-hydroxysteroid dehydrogenase type I inhibitors |
| ATE480239T1 (de) | 2005-06-09 | 2010-09-15 | Oncalis Ag | Angiogeneseinhibitoren |
| US7632837B2 (en) | 2005-06-17 | 2009-12-15 | Bristol-Myers Squibb Company | Bicyclic heterocycles as cannabinoid-1 receptor modulators |
| US7452892B2 (en) | 2005-06-17 | 2008-11-18 | Bristol-Myers Squibb Company | Triazolopyrimidine cannabinoid receptor 1 antagonists |
| TW200726765A (en) | 2005-06-17 | 2007-07-16 | Bristol Myers Squibb Co | Triazolopyridine cannabinoid receptor 1 antagonists |
| WO2007028051A2 (en) | 2005-09-02 | 2007-03-08 | Abbott Laboratories | Novel imidazo based heterocycles |
| CN101300233A (zh) | 2005-09-09 | 2008-11-05 | 先灵公司 | 氮杂稠合的细胞周期蛋白依赖性激酶抑制剂 |
| TW200804386A (en) | 2005-11-10 | 2008-01-16 | Schering Corp | Imidazopyrazines as protein kinase inhibitors |
| KR20120107533A (ko) | 2005-11-28 | 2012-10-02 | 마리누스 파마슈티컬스 | ｇａｎａｘｏｌｏｎｅ 제형, 이의 제조방법 및 용도 |
| ATE537171T1 (de) | 2005-12-27 | 2011-12-15 | Hoffmann La Roche | Aryl-isoxazol-4-yl-imidazoä1,5-aüpyridin-deriva e |
| WO2007074491A1 (en) | 2005-12-28 | 2007-07-05 | Universita Degli Studi Di Siena | HETEROTRICYCLIC AMIDE DERIVATIVES AS NEUROKININ-l (NKl) RECEPTOR LIGANDS |
| PE20070978A1 (es) | 2006-02-14 | 2007-11-15 | Novartis Ag | COMPUESTOS HETEROCICLICOS COMO INHIBIDORES DE FOSFATIDILINOSITOL 3-QUINASAS (PI3Ks) |
| EP2004643A1 (en) | 2006-03-31 | 2008-12-24 | Novartis AG | Organic compounds |
| CN101516883A (zh) | 2006-06-06 | 2009-08-26 | 先灵公司 | 作为蛋白激酶抑制剂的咪唑并吡嗪化合物 |
| US20090175852A1 (en) | 2006-06-06 | 2009-07-09 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| US8115000B2 (en) | 2006-06-22 | 2012-02-14 | Mallinckrodt Llc | Pyrazine derivatives and uses thereof in renal monitoring |
| CN101472903A (zh) | 2006-06-22 | 2009-07-01 | 马林克罗特公司 | 具有扩展共轭的吡嗪衍生物及其用途 |
| CA2655720A1 (en) | 2006-06-29 | 2008-01-10 | Schering Corporation | Substituted bicyclic and tricyclic thrombin receptor antagonists |
| WO2008005423A1 (en) | 2006-07-03 | 2008-01-10 | Cambrex Charles City, Inc. | Improved method of making sufentanil |
| US7501438B2 (en) | 2006-07-07 | 2009-03-10 | Forest Laboratories Holdings Limited | Pyridoimidazole derivatives |
| US8217177B2 (en) | 2006-07-14 | 2012-07-10 | Amgen Inc. | Fused heterocyclic derivatives and methods of use |
| PE20121506A1 (es) | 2006-07-14 | 2012-11-26 | Amgen Inc | Compuestos triazolopiridinas como inhibidores de c-met |
| US8198448B2 (en) | 2006-07-14 | 2012-06-12 | Amgen Inc. | Fused heterocyclic derivatives and methods of use |
| EP2044061A2 (en) | 2006-07-20 | 2009-04-08 | Mehmet Kahraman | Benzothiophene inhibitors of rho kinase |
| US7563797B2 (en) | 2006-08-28 | 2009-07-21 | Forest Laboratories Holding Limited | Substituted imidazo(1,2-A)pyrimidines and imidazo(1,2-A) pyridines as cannabinoid receptor ligands |
| DE102006041292A1 (de) | 2006-09-01 | 2008-03-06 | Henkel Kgaa | Wasserstoffperoxid-Aktivierung mit N-Heterocyclen |
| WO2008037607A1 (de) | 2006-09-25 | 2008-04-03 | Basf Se | Carbonylgruppen-enthaltende heterocyclische verbindungen und deren verwendung zur bekämpfung von phytopathogenen pilzen |
| WO2008045393A2 (en) | 2006-10-11 | 2008-04-17 | Amgen Inc. | Imidazo- and triazolo-pyridine compounds and methods of use therof |
| WO2008063910A2 (en) | 2006-11-08 | 2008-05-29 | Novavax, Inc. | Method of preparing solid dosage forms of multi-phasic pharmaceutical compositions |
| WO2008056176A1 (en) | 2006-11-10 | 2008-05-15 | Scottish Biomedical Limited | Pyrazolopyrimidines as phosphodiesterase inhibitors |
| PL2497470T3 (pl) | 2006-11-22 | 2016-04-29 | Incyte Holdings Corp | Imidazotriazyny i imidazopirymidyny jako inhibitory kinazy |
| DE602007012133D1 (de) | 2006-12-01 | 2011-03-03 | Andrew Burritt | Triazolopyridinverbindungen zur behandlung von degenerations- und entzündungskrankheiten |
| AU2007338631A1 (en) | 2006-12-22 | 2008-07-03 | Combinatorx, Incorporated | Pharmaceutical compositions for treatment of parkinson's disease and related disorders |
| JP5612860B2 (ja) | 2007-03-09 | 2014-10-22 | プロビオドルグ エージー | グルタミニルシクラーゼ阻害剤としてのイミダゾ［１，５−ａ］ピリジン誘導体 |
| DE102007012645A1 (de) | 2007-03-16 | 2008-09-18 | Bayer Healthcare Ag | Substituierte Imidazo- und Triazolopyrimidine |
| EP1972628A1 (en) | 2007-03-21 | 2008-09-24 | Schwarz Pharma Ag | Indolizines and aza-analog derivatives thereof as CNS active compounds |
| JP2010523725A (ja) | 2007-04-16 | 2010-07-15 | レオ ファーマ アクティーゼルスカブ | 皮膚疾患処置用ホスホジエステラーゼ阻害剤としてのトリアゾロピリジン |
| CN101687873A (zh) | 2007-04-17 | 2010-03-31 | 百时美施贵宝公司 | 具有稠合杂环的11β-羟基类固醇Ⅰ型脱氢酶抑制剂 |
| CN101855222A (zh) | 2007-05-10 | 2010-10-06 | 通用电气健康护理有限公司 | 对大麻素cb2受体具有活性的咪唑并(1,2-a)吡啶和相关化合物 |
| JP5343845B2 (ja) | 2007-05-21 | 2013-11-13 | 東レ株式会社 | 特定の有機酸を含有する経口製剤並びに経口製剤の溶出性及び化学的安定性の改善方法 |
| RU2487873C2 (ru) | 2007-06-08 | 2013-07-20 | Эбботт Лэборетриз | 5-замещенные индазолы в качестве ингибиторов киназы |
| US8648069B2 (en) | 2007-06-08 | 2014-02-11 | Abbvie Inc. | 5-substituted indazoles as kinase inhibitors |
| MX2009013729A (es) | 2007-06-14 | 2010-01-25 | Schering Corp | Imidazopirazinas como inhibidores de proteina quinasa. |
| CL2008001839A1 (es) | 2007-06-21 | 2009-01-16 | Incyte Holdings Corp | Compuestos derivados de 2,7-diazaespirociclos, inhibidores de 11-beta hidroxil esteroide deshidrogenasa tipo 1; composicion farmaceutica que comprende a dichos compuestos; utiles para tratar la obesidad, diabetes, intolerancia a la glucosa, diabetes tipo ii, entre otras enfermedades. |
| US20090004281A1 (en) | 2007-06-26 | 2009-01-01 | Biovail Laboratories International S.R.L. | Multiparticulate osmotic delivery system |
| AU2008277628B2 (en) | 2007-07-18 | 2012-03-15 | Novartis Ag | Bicyclic heteroaryl compounds and their use as kinase inhibitors |
| KR20100042287A (ko) | 2007-07-31 | 2010-04-23 | 쉐링 코포레이션 | 항암요법으로서의 항-유사분열제 및 아우로라 키나제 억제제 조합물 |
| WO2009017954A1 (en) | 2007-08-01 | 2009-02-05 | Phenomix Corporation | Inhibitors of jak2 kinase |
| BRPI0814939A2 (pt) | 2007-08-10 | 2015-01-27 | Glaxosmithkline Llc | Entidade química, composição farmacêutica, e, método para tratar uma infecção viral em um mamífero. |
| US20090047336A1 (en) | 2007-08-17 | 2009-02-19 | Hong Kong Baptist University | novel formulation of dehydrated lipid vesicles for controlled release of active pharmaceutical ingredient via inhalation |
| FR2920091A1 (fr) | 2007-08-24 | 2009-02-27 | Oreal | Composition tinctoriale comprenant une base d'oxydation aminopyrazolopyridine, un coupleur et un polyol particulier. |
| FR2920090A1 (fr) | 2007-08-24 | 2009-02-27 | Oreal | Composition tinctoriale comprenant une base d'oxydation aminopyrazolopyridine particuliere, un coupleur et un tensioactif particulier. |
| KR20090022616A (ko) | 2007-08-31 | 2009-03-04 | 한올제약주식회사 | 베실산클로피도그렐 함유 경구투여용 약제 |
| US8119658B2 (en) | 2007-10-01 | 2012-02-21 | Bristol-Myers Squibb Company | Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| GB0719803D0 (en) | 2007-10-10 | 2007-11-21 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| BRPI0818533B8 (pt) | 2007-10-11 | 2021-05-25 | Astrazeneca Ab | composto, composição farmacêutica, uso de um composto, e, processo para a preparação de um composto |
| KR20170021904A (ko) | 2007-10-12 | 2017-02-28 | 노파르티스 아게 | 스핑고신 1 포스페이트 (ｓ1ｐ) 수용체 조절제를 포함하는 조성물 |
| CN101903387B (zh) | 2007-12-19 | 2014-05-21 | 健泰科生物技术公司 | 8-苯氨基咪唑并吡啶和它们在制备抗癌剂和/或抗炎剂中的用途 |
| PE20091268A1 (es) | 2007-12-19 | 2009-09-19 | Amgen Inc | Derivados heterociclicos como inhibidores de pi3 quinasa |
| KR100988233B1 (ko) | 2007-12-26 | 2010-10-18 | 한미홀딩스 주식회사 | 클로피도그렐 1,5-나프탈렌 다이술폰산 염 또는 이의수화물의 약학 조성물 및 제제 |
| AU2009223640B2 (en) | 2008-03-11 | 2013-07-04 | Incyte Holdings Corporation | Azetidine and cyclobutane derivatives as jak inhibitors |
| EP2265603B1 (en) | 2008-03-13 | 2014-05-07 | The General Hospital Corporation | Inhibitors of the bmp signaling pathway |
| US8637542B2 (en) | 2008-03-14 | 2014-01-28 | Intellikine, Inc. | Kinase inhibitors and methods of use |
| JPWO2009128520A1 (ja) | 2008-04-18 | 2011-08-04 | 塩野義製薬株式会社 | Ｐｉ３ｋ阻害活性を有する複素環化合物 |
| DE102008023801A1 (de) | 2008-05-15 | 2009-11-19 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Imidazo- und Triazolopyrimidine, Imidazo- und Pyrazolopyrazine und Imidazotriazine |
| US8349210B2 (en) | 2008-06-27 | 2013-01-08 | Transitions Optical, Inc. | Mesogenic stabilizers |
| WO2010010188A1 (en) | 2008-07-25 | 2010-01-28 | Galapagos Nv | Novel compounds useful for the treatment of degenerative and inflammatory diseases. |
| WO2010010189A1 (en) | 2008-07-25 | 2010-01-28 | Galapagos Nv | Novel compounds useful for the treatment of degenerative and inflammatory diseases |
| WO2010010184A1 (en) | 2008-07-25 | 2010-01-28 | Galapagos Nv | [1, 2, 4] triazolo [1, 5-a] pyridines as jak inhibitors |
| WO2010010187A1 (en) | 2008-07-25 | 2010-01-28 | Galapagos Nv | Novel compounds useful for the treatment of degenerative and inflammatory diseases |
| UY32049A (es) | 2008-08-14 | 2010-03-26 | Takeda Pharmaceutical | Inhibidores de cmet |
| TR200806298A2 (tr) | 2008-08-22 | 2010-03-22 | Bi̇lgi̇ç Mahmut | Farmasötik formülasyon |
| JP2010070503A (ja) | 2008-09-19 | 2010-04-02 | Daiichi Sankyo Co Ltd | 抗真菌作用２−アミノトリアゾロピリジン誘導体 |
| US20120021519A1 (en) | 2008-09-19 | 2012-01-26 | Presidents And Fellows Of Harvard College | Efficient induction of pluripotent stem cells using small molecule compounds |
| EP2346508B1 (en) | 2008-09-26 | 2016-08-24 | Intellikine, LLC | Heterocyclic kinase inhibitors |
| EP2361242B1 (en) | 2008-10-17 | 2018-08-01 | Oryzon Genomics, S.A. | Oxidase inhibitors and their use |
| WO2010048149A2 (en) | 2008-10-20 | 2010-04-29 | Kalypsys, Inc. | Heterocyclic modulators of gpr119 for treatment of disease |
| WO2010064020A1 (en) | 2008-12-04 | 2010-06-10 | Proximagen Ltd. | Imidazopyridine compounds |
| US8450321B2 (en) | 2008-12-08 | 2013-05-28 | Gilead Connecticut, Inc. | 6-(1H-indazol-6-yl)-N-[4-(morpholin-4-yl)phenyl]imidazo-[1,2-A]pyrazin-8-amine, or a pharmaceutically acceptable salt thereof, as a SYK inhibitor |
| US8993808B2 (en) | 2009-01-21 | 2015-03-31 | Oryzon Genomics, S.A. | Phenylcyclopropylamine derivatives and their medical use |
| WO2010090991A1 (en) | 2009-02-04 | 2010-08-12 | Supernus Pharmaceuticals, Inc. | Formulations of desvenlafaxine |
| JP5589003B2 (ja) | 2009-02-04 | 2014-09-10 | ヴァイティー ファーマシューティカルズ，インコーポレイテッド | 脂質障害のような代謝疾患の処置のために有用な［１，３］オキサジン−２−オンの誘導体 |
| TR200900878A2 (tr) | 2009-02-05 | 2010-08-23 | Bi̇lgi̇ç Mahmut | Tek bir dozaj formunda kombine edilen farmasötik formülasyonlar |
| TR200900879A2 (tr) | 2009-02-05 | 2010-08-23 | Bi̇lgi̇ç Mahmut | Aktif maddelerin tek bir dozaj formunda kombine edildiği farmasötik bileşimler |
| CA2752114C (en) | 2009-02-13 | 2017-06-20 | Bayer Pharma Aktiengesellschaft | Fused pyrimidines as akt inhibitors |
| KR20100101056A (ko) | 2009-03-07 | 2010-09-16 | 주식회사 메디젠텍 | 세포핵에서 세포질로의 ｇｓｋ３의 이동을 억제하는 화합물을 함유하는 세포핵에서 세포질로의 ｇｓｋ３ 이동에 의해 발생되는 질환의 치료 또는 예방용 약학적 조성물 |
| WO2010107404A1 (en) | 2009-03-16 | 2010-09-23 | Mahmut Bilgic | Stable pharmaceutical combinations |
| US8481732B2 (en) | 2009-03-20 | 2013-07-09 | Incyte Corporation | Substituted heterocyclic compounds |
| HRP20130846T1 (hr) | 2009-03-31 | 2013-11-22 | Kissei Pharmaceutical Co., Ltd. | Derivati indolizina i njihova uporaba u medicinske svrhe |
| JP5805623B2 (ja) | 2009-04-16 | 2015-11-04 | フンダシオン セントロ ナシオナル デ インベスティガシオネス オンコロヒカス カルロス ザ サードＦｕｎｄａｃｉｏｎ Ｃｅｎｔｒｏ Ｎａｃｉｏｎａｌ ｄｅ Ｉｎｖｅｓｔｉｇａｃｉｏｎｅｓ Ｏｎｃｏｌｏｇｉｃａｓ Ｃａｒｌｏｓ ＩＩＩ | キナーゼ阻害剤として使用するためのイミダゾピラジン類 |
| TWI461426B (zh) | 2009-05-27 | 2014-11-21 | Merck Sharp & Dohme | （二氫）咪唑並異〔５，１－ａ〕喹啉類 |
| AU2010258785A1 (en) | 2009-06-10 | 2012-01-19 | Sunovion Pharmaceuticals Inc. | Histamine H3 inverse agonists and antagonists and methods of use thereof |
| NZ597108A (en) | 2009-06-25 | 2014-04-30 | Alkermes Pharma Ireland Ltd | Prodrugs of nh-acidic compounds |
| JP5819831B2 (ja) | 2009-08-17 | 2015-11-24 | インテリカイン， エルエルシー | 複素環式化合物およびそれらの使用 |
| WO2011022489A2 (en) | 2009-08-18 | 2011-02-24 | The Johns Hopkins University | (bis) urea and (bis) thiourea compounds as epigenic modulators of lysine-specific demethylase 1 and methods of treating disorders |
| WO2011033265A1 (en) | 2009-09-18 | 2011-03-24 | Almac Discovery Limited | Pharmaceutical compounds |
| AU2010297557C1 (en) | 2009-09-25 | 2017-04-06 | Oryzon Genomics S.A. | Lysine specific demethylase-1 inhibitors and their use |
| US8946296B2 (en) | 2009-10-09 | 2015-02-03 | Oryzon Genomics S.A. | Substituted heteroaryl- and aryl-cyclopropylamine acetamides and their use |
| WO2011050245A1 (en) | 2009-10-23 | 2011-04-28 | Yangbo Feng | Bicyclic heteroaryls as kinase inhibitors |
| US8541404B2 (en) | 2009-11-09 | 2013-09-24 | Elexopharm Gmbh | Inhibitors of the human aldosterone synthase CYP11B2 |
| US8614315B2 (en) | 2009-12-25 | 2013-12-24 | Mahmut Bilgic | Cefdinir and cefixime formulations and uses thereof |
| ES2627703T3 (es) | 2010-01-22 | 2017-07-31 | Fundación Centro Nacional De Investigaciones Oncológicas Carlos Iii | Inhibidores de PI3·quinasa |
| WO2011097607A1 (en) | 2010-02-08 | 2011-08-11 | Southern Research Institute | Anti-viral treatment and assay to screen for anti-viral agent |
| US9616058B2 (en) | 2010-02-24 | 2017-04-11 | Oryzon Genomics, S.A. | Potent selective LSD1 inhibitors and dual LSD1/MAO-B inhibitors for antiviral use |
| WO2011106573A2 (en) | 2010-02-24 | 2011-09-01 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with hepadnaviridae |
| TW201200518A (en) | 2010-03-10 | 2012-01-01 | Kalypsys Inc | Heterocyclic inhibitors of histamine receptors for the treatment of disease |
| ES2551407T3 (es) | 2010-03-18 | 2015-11-18 | Bayer Intellectual Property Gmbh | Imidazopirazinas |
| BR112012023576B1 (pt) | 2010-03-18 | 2022-08-23 | Institut Pasteur Korea | Compostos anti-infecciosos e composições compreendendo os mesmos |
| ES2627688T3 (es) | 2010-04-02 | 2017-07-31 | Ogeda Sa | Novedosos compuestos antagonistas selectivos del receptor de NK-3, composición farmacéutica y métodos para uso en trastornos mediados por los receptores de NK-3 |
| JP5868948B2 (ja) | 2010-04-19 | 2016-02-24 | オリゾン・ジェノミックス・ソシエダッド・アノニマＯｒｙｚｏｎ Ｇｅｎｏｍｉｃｓ Ｓ．Ａ． | リジン特異的脱メチル化酵素１阻害薬およびその使用 |
| EA022459B1 (ru) | 2010-04-20 | 2016-01-29 | Университа' Дельи Студи Ди Рома "Ла Сапиенца" | Производные транилципромина в качестве ингибиторов гистон деметилаз lsd1 и/или lsd2 |
| JPWO2011136264A1 (ja) | 2010-04-28 | 2013-07-22 | 第一三共株式会社 | ［５，６］複素環化合物 |
| WO2011143365A1 (en) | 2010-05-13 | 2011-11-17 | Amgen Inc. | Nitrogen heterocyclic compounds useful as pde10 inhibitors |
| WO2011141713A1 (en) | 2010-05-13 | 2011-11-17 | Centro Nacional De Investigaciones Oncologicas (Cnio) | New bicyclic compounds as pi3-k and mtor inhibitors |
| CN102247321A (zh) | 2010-05-20 | 2011-11-23 | 上海亚盛医药科技有限公司 | 一种阿朴棉子酚酮自乳化药物传递系统及其制备方法 |
| WO2011149438A1 (en) | 2010-05-28 | 2011-12-01 | Mahmut Bilgic | Combination of antihypertensive agents |
| CN102295642B (zh) | 2010-06-25 | 2016-04-06 | 中国人民解放军军事医学科学院毒物药物研究所 | 2-芳基咪唑并[1,2-a]吡啶-3-乙酰胺衍生物、其制备方法及用途 |
| NZ604478A (en) | 2010-07-02 | 2014-12-24 | Gilead Sciences Inc | Fused heterocyclic compounds as ion channel modulators |
| WO2012007345A2 (en) | 2010-07-12 | 2012-01-19 | Bayer Pharma Aktiengesellschaft | Substituted imidazo[1,2-a]pyrimidines and -pyridines |
| WO2012009475A1 (en) | 2010-07-14 | 2012-01-19 | Oregon Health & Science University | Methods of treating cancer with inhibition of lysine-specific demethylase 1 |
| CN101987082B (zh) | 2010-07-16 | 2013-04-03 | 钟术光 | 固体制剂及其制备方法 |
| CN101987081B (zh) | 2010-07-16 | 2012-08-08 | 钟术光 | 一种控释制剂 |
| WO2012016133A2 (en) | 2010-07-29 | 2012-02-02 | President And Fellows Of Harvard College | Ros1 kinase inhibitors for the treatment of glioblastoma and other p53-deficient cancers |
| BR112013002164B1 (pt) | 2010-07-29 | 2021-11-09 | Oryzon Genomics S.A. | Inibidores de desmetilase à base de arilciclopropilamina de lsd1, seus usos, e composição farmacêutica |
| EP2598480B1 (en) | 2010-07-29 | 2019-04-24 | Oryzon Genomics, S.A. | Cyclopropylamine derivatives useful as lsd1 inhibitors |
| WO2012034116A2 (en) | 2010-09-10 | 2012-03-15 | The Johns Hopkins University | Small molecules as epigenetic modulators of lysine-specific demethylase 1 and methods of treating disorders |
| CN102397552B (zh) | 2010-09-10 | 2016-06-08 | 广州自远生物科技有限公司 | 一种含喹诺酮类的药物复合制剂及其制备方法和应用 |
| JP5906191B2 (ja) | 2010-09-29 | 2016-04-20 | キッセイ薬品工業株式会社 | （アザ）インドリジン誘導体及びその医薬用途 |
| US20130303545A1 (en) | 2010-09-30 | 2013-11-14 | Tamara Maes | Cyclopropylamine derivatives useful as lsd1 inhibitors |
| WO2012047852A2 (en) | 2010-10-07 | 2012-04-12 | The J. David Gladstone Institutes | Compositions and methods for modulating immunodeficiency virus transcription |
| JP5815720B2 (ja) | 2010-10-18 | 2015-11-17 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | 殺線虫性スルホンアミド |
| WO2012052745A1 (en) | 2010-10-21 | 2012-04-26 | Centro Nacional De Investigaciones Oncológicas (Cnio) | Combinations of pi3k inhibitors with a second anti -tumor agent |
| PL2630146T3 (pl) | 2010-10-21 | 2020-11-02 | Medivation Technologies Llc | Krystaliczna sól tosylanowa (8S,9R)-5-fluoro-8-(4-fluorofenylo)-9-(1-metylo-1H-1,2,4-triazol-5-ilo)-8,9-dihydro-2H-pirydo[4,3,2-de]ftalazyno-3(7H)-onu |
| EP2444084A1 (en) | 2010-10-21 | 2012-04-25 | Centro Nacional de Investigaciones Oncológicas (CNIO) | Use of PI3K inibitors for the treatment of obesity |
| WO2012071469A2 (en) | 2010-11-23 | 2012-05-31 | Nevada Cancer Institute | Histone demethylase inhibitors and uses thereof for treatment o f cancer |
| WO2012072713A2 (en) | 2010-11-30 | 2012-06-07 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with flaviviridae |
| EP2651404B1 (en) | 2010-12-14 | 2015-10-14 | Electrophoretics Limited | Casein kinase 1delta (ck1delta) inhibitors |
| US20140187548A1 (en) | 2010-12-17 | 2014-07-03 | Bayer Intellectual Property Gmbh | 6 substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| ES2556458T3 (es) | 2010-12-17 | 2016-01-18 | Bayer Intellectual Property Gmbh | 6-Imidazopirazinas sustituidas para uso como inhibidores de Mps-1 y TKK en el tratamiento de trastornos hiperproliferativos |
| CN103370322B (zh) | 2010-12-17 | 2016-02-10 | 拜耳知识产权有限责任公司 | 在过度增殖性病症的治疗中用作mps-1和tkk抑制剂的2-取代的咪唑并吡嗪 |
| UY33805A (es) | 2010-12-17 | 2012-07-31 | Boehringer Ingelheim Int | ?Derivados de dihidrobenzofuranil-piperidinilo, aza-dihidrobenzofuranilpiperidinilo y diaza-dihidrobenzofuranil-piperidinilo, composiciones farmacéuticas que los contienen y usos de los mismos?. |
| JP2013545779A (ja) | 2010-12-17 | 2013-12-26 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 過剰増殖性障害の治療におけるｍｐｓ−１およびｔｋｋ阻害剤として使用するための６置換イミダゾピラジン |
| TWI617559B (zh) | 2010-12-22 | 2018-03-11 | 江蘇恆瑞醫藥股份有限公司 | ２－芳基咪唑并［１，２－ｂ］嗒．２－苯基咪唑并［１，２－ａ］吡啶，和２－苯基咪唑并［１，２－ａ］吡衍生物 |
| EP2655334B1 (en) | 2010-12-22 | 2018-10-03 | Eutropics Pharmaceuticals, Inc. | Compositions and methods useful for treating diseases |
| EP2665726A4 (en) | 2011-01-21 | 2014-09-03 | Gen Hospital Corp | COMPOSITIONS AND METHODS OF TREATING CARDIOVASCULAR DISEASES |
| EP3981395A1 (en) | 2011-02-08 | 2022-04-13 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for myeloproliferative disorders |
| EP2712316A1 (en) | 2011-02-08 | 2014-04-02 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for myeloproliferative or lymphoproliferative diseases or disorders |
| US9127000B2 (en) | 2011-02-23 | 2015-09-08 | Intellikine, LLC. | Heterocyclic compounds and uses thereof |
| US9464065B2 (en) | 2011-03-24 | 2016-10-11 | The Scripps Research Institute | Compounds and methods for inducing chondrogenesis |
| BR112013024502B1 (pt) | 2011-03-25 | 2021-09-08 | Glaxosmithkline Intellectual Property (No.2) Limited | Compostos de ciclopropilaminas como inibidores lsd1 e composições farmacêuticas compreendendo ditos compostos |
| WO2012147890A1 (ja) | 2011-04-27 | 2012-11-01 | 持田製薬株式会社 | 新規アゾール誘導体 |
| EP2750671A2 (en) | 2011-05-19 | 2014-07-09 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for thrombosis and cardiovascular diseases |
| EP2524918A1 (en) | 2011-05-19 | 2012-11-21 | Centro Nacional de Investigaciones Oncológicas (CNIO) | Imidazopyrazines derivates as kinase inhibitors |
| WO2012156531A2 (en) | 2011-05-19 | 2012-11-22 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for inflammatory diseases or conditions |
| EP2717708A1 (en) | 2011-06-07 | 2014-04-16 | SPAI Group Ltd. | Compositions and methods for improving stability and extending shelf life of sensitive food additives and food products thereof |
| TWI577676B (zh) | 2011-06-20 | 2017-04-11 | 英塞特控股公司 | 作為ｊａｋ抑制劑之吖丁啶基苯基、吡啶基或吡基羧醯胺衍生物 |
| TW201311149A (zh) | 2011-06-24 | 2013-03-16 | Ishihara Sangyo Kaisha | 有害生物防治劑 |
| EP2548877A1 (en) | 2011-07-19 | 2013-01-23 | MSD Oss B.V. | 4-(5-Membered fused pyridinyl)benzamides as BTK-inhibitors |
| EA025529B1 (ru) | 2011-08-09 | 2017-01-30 | Такеда Фармасьютикал Компани Лимитед | Циклопропанаминовое соединение |
| SG2014009609A (en) | 2011-08-15 | 2014-05-29 | Univ Utah Res Found | Substituted (e)-n'-(1-phenylethylidene) benzohydrazide analogs as histone demethylase inhiitors |
| WO2013033688A1 (en) | 2011-09-01 | 2013-03-07 | The Brigham And Women's Hospital, Inc. | Treatment of cancer |
| JP6067019B2 (ja) | 2011-09-02 | 2017-01-25 | プロメガ コーポレイションＰｒｏｍｅｇａ Ｃｏｒｐｏｒａｔｉｏｎ | 代謝的に活性な細胞の酸化還元状態を評価するための化合物及び方法、ならびにｎａｄ（ｐ）／ｎａｄ（ｐ）ｈを測定するための方法 |
| HK1211023A1 (zh) | 2011-10-10 | 2016-05-13 | H. Lundbeck A/S | 具有咪唑并吡嗪骨架pde9i |
| EP2768805B1 (en) | 2011-10-20 | 2020-03-25 | Oryzon Genomics, S.A. | (hetero)aryl cyclopropylamine compounds as lsd1 inhibitors |
| CL2014000988A1 (es) | 2011-10-20 | 2014-11-03 | Oryzon Genomics Sa | Compuestos derivados de (aril o heteroaril) ciclopropilamida, inhibidores de lsd1; procedimiento para prepararlos; composicion farmaceutica que los comprende; y metodo para tratar o prevenir cancer, una enfermedad neurologica, una infeccion viral y la reactivacion viral despues de la latencia. |
| CN107417549A (zh) * | 2011-10-20 | 2017-12-01 | 奥莱松基因组股份有限公司 | 作为lsd1抑制剂的（杂）芳基环丙基胺化合物 |
| ITMI20111971A1 (it) | 2011-10-28 | 2013-04-29 | Mesogenics Srl | Inibitori dell'enzima lsd-1 per l'induzione del differenziamento osteogenico |
| WO2013074390A1 (en) | 2011-11-14 | 2013-05-23 | Merck Sharp & Dohme Corp. | Triazolopyridinone pde10 inhibitors |
| CA2857964A1 (en) | 2011-12-05 | 2013-06-13 | Brandeis University | Treatment of amyloidosis by compounds that regulate retromer stabilization |
| HK1203948A1 (en) | 2012-03-07 | 2015-11-06 | Merck Patent Gmbh | Triazolopyrazine derivatives |
| CN102587054B (zh) | 2012-03-13 | 2014-05-07 | 机械科学研究总院先进制造技术研究中心 | 缸盖自动锁紧装置及包括该装置的筒子纱染色机 |
| GB201205669D0 (en) | 2012-03-30 | 2012-05-16 | Agency Science Tech & Res | Bicyclic heterocyclic derivatives as mnk2 and mnk2 modulators and uses thereof |
| CN102579381B (zh) | 2012-03-30 | 2013-07-10 | 河南中帅医药科技发展有限公司 | 盐酸胍法辛缓释制剂及其制备方法 |
| CN103373996A (zh) | 2012-04-20 | 2013-10-30 | 山东亨利医药科技有限责任公司 | 作为crth2受体拮抗剂的二并环衍生物 |
| WO2014002051A2 (en) | 2012-06-28 | 2014-01-03 | Novartis Ag | Complement pathway modulators and uses thereof |
| CN102772444A (zh) | 2012-07-06 | 2012-11-14 | 周明千 | 中药超微破壁口服片剂饮片的加工方法 |
| GB201212513D0 (en) | 2012-07-13 | 2012-08-29 | Ucb Pharma Sa | Therapeutic agents |
| CA2886187C (en) | 2012-09-28 | 2020-04-14 | Vanderbilt University | Fused heterocyclic compounds as selective bmp inhibitors |
| EP2903978B1 (en) | 2012-10-05 | 2022-12-07 | Rigel Pharmaceuticals, Inc. | Gdf-8 inhibitors |
| CA2887598A1 (en) * | 2012-10-12 | 2014-04-17 | Takeda Pharmaceutical Company Limited | Cyclopropanamine compound and use thereof |
| CA2890897A1 (en) | 2012-11-14 | 2014-05-22 | The Board Of Regents Of The University Of Texas System | Inhibition of hif-2.alpha. heterodimerization with hif 1.beta. (arnt) |
| WO2014084298A1 (ja) | 2012-11-28 | 2014-06-05 | 京都府公立大学法人 | リシン構造を有するｌｓｄ1選択的阻害薬 |
| EP2925307B1 (en) | 2012-11-30 | 2020-10-28 | McCord, Darlene E. | Hydroxytyrosol and oleuropein compositions for induction of dna damage, cell death and lsd1 inhibition |
| EP2740474A1 (en) | 2012-12-05 | 2014-06-11 | Instituto Europeo di Oncologia S.r.l. | Cyclopropylamine derivatives useful as inhibitors of histone demethylases kdm1a |
| CA2889165A1 (en) | 2012-12-19 | 2014-06-26 | Wockhardt Limited | A stable aqueous composition comprising human insulin or an analogue or derivative thereof |
| CN103054869A (zh) | 2013-01-18 | 2013-04-24 | 郑州大学 | 含三唑基的氨基二硫代甲酸酯化合物在制备以lsd1为靶标药物中的应用 |
| CN103933036B (zh) | 2013-01-23 | 2017-10-13 | 中国人民解放军军事医学科学院毒物药物研究所 | 2‑芳基咪唑并[1,2‑α]吡啶‑3‑乙酰胺衍生物在制备防治PTSD的药物中的用途 |
| CN105263910A (zh) | 2013-02-18 | 2016-01-20 | 斯克利普斯研究所 | 具有治疗潜力的血管加压素受体调节剂 |
| US8558008B2 (en) | 2013-02-28 | 2013-10-15 | Dermira, Inc. | Crystalline glycopyrrolate tosylate |
| WO2014164867A1 (en) | 2013-03-11 | 2014-10-09 | Imago Biosciences | Kdm1a inhibitors for the treatment of disease |
| US20160050895A1 (en) | 2013-03-13 | 2016-02-25 | Australian Nuclear Science And Technology Organization | Transgenic non-human organisms with non-functional tspo genes |
| US20140343118A1 (en) | 2013-03-14 | 2014-11-20 | Duke University | Methods of treatment using arylcyclopropylamine compounds |
| JP2016517434A (ja) | 2013-03-14 | 2016-06-16 | エピザイム，インコーポレイティド | 癌を処置するための併用療法 |
| US9918983B2 (en) | 2013-05-30 | 2018-03-20 | The Board Of Regents Of The Nevada System Of Higher Education On Behalf Of The University Of Nevada, Las Vegas | Suicidal LSD1 inhibitors targeting SOX2-expressing cancer cells |
| BR112015032113B1 (pt) | 2013-06-19 | 2019-01-29 | University Of Utah Research Foundation | análogos de (e)-n’-(1-feniletilideno)benzohidrazida substituídos como inibidores de histona demetilase |
| SMT202000071T1 (it) | 2013-06-21 | 2020-03-13 | Myokardia Inc | Composti di pirimidinadione contro le condizioni cardiache |
| US9186391B2 (en) | 2013-08-29 | 2015-11-17 | Musc Foundation For Research Development | Cyclic peptide inhibitors of lysine-specific demethylase 1 |
| WO2015031564A2 (en) | 2013-08-30 | 2015-03-05 | University Of Utah | Substituted-1h-benzo[d]imidazole series compounds as lysine-specfic demethylase 1 (lsd1) inhibitors |
| US9770514B2 (en) | 2013-09-03 | 2017-09-26 | ExxPharma Therapeutics LLC | Tamper-resistant pharmaceutical dosage forms |
| PL3043778T3 (pl) | 2013-09-13 | 2018-04-30 | Bayer Pharma Aktiengesellschaft | Kompozycje farmaceutyczne zawierające refametinib |
| KR101568724B1 (ko) | 2013-11-13 | 2015-11-12 | 서울대학교산학협력단 | 신규한 화합물, 이의 생산 방법, 및 히스톤 디메틸라제 저해제로서 이의 용도 |
| FI3080100T3 (fi) | 2013-12-11 | 2023-03-15 | Celgene Quanticel Res Inc | Lysiinispesifisen demetylaasi-1:n estäjät |
| US9346776B2 (en) | 2014-02-13 | 2016-05-24 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compound |
| US9527835B2 (en) | 2014-02-13 | 2016-12-27 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| PL3105218T3 (pl) | 2014-02-13 | 2020-03-31 | Incyte Corporation | Cyklopropyloaminy jako inhibitory lsd1 |
| LT3105226T (lt) | 2014-02-13 | 2019-11-11 | Incyte Corp | Ciklopropilaminai, kaip lsd1 inhibitoriai |
| TW201613860A (en) | 2014-02-13 | 2016-04-16 | Incyte Corp | Cyclopropylamines as LSD1 inhibitors |
| US9428470B2 (en) | 2014-02-13 | 2016-08-30 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| CN103893163B (zh) | 2014-03-28 | 2016-02-03 | 中国药科大学 | 2-([1，1′-联苯]-4-基)2-氧代乙基4-((3-氯-4-甲基苯基)氨基)-4-氧代丁酸酯在制备lsd1抑制剂药物中的应用 |
| HUE041457T2 (hu) | 2014-04-02 | 2019-05-28 | Bristol Myers Squibb Co | Biaril kináz inhibitorok |
| EP2933002A1 (en) | 2014-04-11 | 2015-10-21 | Sanovel Ilac Sanayi ve Ticaret A.S. | Pharmaceutical combinations of dabigatran and proton pump inhibitors |
| CA2945085C (en) | 2014-04-11 | 2022-05-10 | Takeda Pharmaceutical Company Limited | Cyclopropanamine compound and use thereof |
| EP2929884A1 (en) | 2014-04-11 | 2015-10-14 | Sanovel Ilac Sanayi ve Ticaret A.S. | Pharmaceutical combinations of dabigatran and h2-receptor antagonists |
| CN103961340B (zh) | 2014-04-30 | 2019-06-25 | 南通中国科学院海洋研究所海洋科学与技术研究发展中心 | 一类lsd1抑制剂及其应用 |
| JP6320570B2 (ja) | 2014-05-30 | 2018-05-09 | イエオ−イスティトゥート・エウロペオ・ディ・オンコロジア・エッセ・エッレ・エッレ | ヒストンデメチラーゼ阻害剤としてのシクロプロピルアミン化合物 |
| CN104119280B (zh) | 2014-06-27 | 2016-03-16 | 郑州大学 | 含氨基类脲与端炔结构单元的嘧啶衍生物、制备方法及应用 |
| US9758523B2 (en) | 2014-07-10 | 2017-09-12 | Incyte Corporation | Triazolopyridines and triazolopyrazines as LSD1 inhibitors |
| WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| US9695180B2 (en) | 2014-07-10 | 2017-07-04 | Incyte Corporation | Substituted imidazo[1,2-a]pyrazines as LSD1 inhibitors |
| TWI687419B (zh) | 2014-07-10 | 2020-03-11 | 美商英塞特公司 | 作為ｌｓｄ１抑制劑之咪唑并吡啶及咪唑并吡嗪 |
| GB201417828D0 (en) | 2014-10-08 | 2014-11-19 | Cereno Scient Ab | New methods and compositions |
| CN104173313B (zh) | 2014-08-25 | 2017-05-17 | 杭州朱养心药业有限公司 | 利伐沙班片剂药物组合物 |
| JP6653116B2 (ja) | 2014-08-27 | 2020-02-26 | 日本ケミファ株式会社 | オルメサルタンのプロドラッグ製剤 |
| MX381729B (es) | 2014-10-08 | 2025-03-13 | Hoffmann La Roche | Derivados espirodiamina como inhibidores de la aldosterona sintasa. |
| EP3277689B1 (en) | 2015-04-03 | 2019-09-04 | Incyte Corporation | Heterocyclic compounds as lsd1 inhibitors |
| CA2981584A1 (en) | 2015-04-03 | 2016-10-06 | Bristol-Myers Squibb Company | Inhibitors of indoleamine 2,3-dioxygenase for the treatment of cancer |
| JP2018510198A (ja) | 2015-04-03 | 2018-04-12 | ミュタビリスＭｕｔａｂｉｌｉｓ | 複素環式化合物及びそれらの細菌感染症の予防または治療のための使用 |
| KR102710120B1 (ko) | 2015-08-12 | 2024-09-27 | 인사이트 홀딩스 코포레이션 | Lsd1 저해제의 염 |
| CN112656772B (zh) | 2015-10-15 | 2022-05-20 | 浙江东日药业有限公司 | 利伐沙班药物组合物 |
| US9809541B2 (en) | 2015-12-29 | 2017-11-07 | Mirati Therapeutics, Inc. | LSD1 inhibitors |
| JPWO2017130933A1 (ja) | 2016-01-25 | 2018-11-29 | 国立大学法人 熊本大学 | 神経変性疾患治療剤 |
| WO2017184934A1 (en) | 2016-04-22 | 2017-10-26 | Incyte Corporation | Formulations of an lsd1 inhibitor |
| WO2018136634A1 (en) | 2017-01-18 | 2018-07-26 | Vanderbilt University | Fused heterocyclic compounds as selective bmp inhibitors |
| BR112019017108A2 (pt) | 2017-03-16 | 2020-04-07 | Jiangsu Hengrui Medicine Co | derivados de heteroaril[4,3-c]pirimidina-5-amina, método de preparação dos mesmos, e usos médicos dos mesmos |
| GEP20237560B (en) | 2018-07-05 | 2023-10-25 | Incyte Corp | Fused pyrazine derivatives as a2a / a2b inhibitors |
| WO2020047198A1 (en) | 2018-08-31 | 2020-03-05 | Incyte Corporation | Salts of an lsd1 inhibitor and processes for preparing the same |
-
2015
- 2015-02-12 LT LT15707007T patent/LT3105226T/lt unknown
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