JP2017510555A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- XZDHATBCLTUCFX-UHFFFAOYSA-N 2-[1-methyl-3-[4-[(2-phenylcyclopropyl)amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound CN1CC(CC#N)(C1)N1CCC(CC1)NC1CC1c1ccccc1 XZDHATBCLTUCFX-UHFFFAOYSA-N 0.000 claims 1
- UUFGEUMETGJRQR-QRWMCTBCSA-N 2-[1-methyl-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetic acid Chemical compound CN1CC(CC(O)=O)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 UUFGEUMETGJRQR-QRWMCTBCSA-N 0.000 claims 1
- XZDHATBCLTUCFX-MUMRKEEXSA-N 2-[1-methyl-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound CN1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 XZDHATBCLTUCFX-MUMRKEEXSA-N 0.000 claims 1
- LHGCYQPQMMRWBE-UHFFFAOYSA-N 2-[1-methyl-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound CN1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1 LHGCYQPQMMRWBE-UHFFFAOYSA-N 0.000 claims 1
- FDRSPKPJWQDXPR-VQTJNVASSA-N 2-[1-methyl-4-[3-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]azetidin-1-yl]piperidin-4-yl]acetonitrile Chemical compound CN1CCC(CC1)(N1CC(C1)CN[C@H]1[C@@H](C1)C1=CC=CC=C1)CC#N FDRSPKPJWQDXPR-VQTJNVASSA-N 0.000 claims 1
- NBGAAOKBUAFGJO-RBUKOAKNSA-N 2-[1-methylsulfonyl-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]ethanol Chemical compound CS(=O)(=O)N1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CCO NBGAAOKBUAFGJO-RBUKOAKNSA-N 0.000 claims 1
- NCGLLDRHTVMYPJ-UHFFFAOYSA-N 2-[1-methylsulfonyl-4-[3-[[(2-phenylcyclopropyl)amino]methyl]azetidin-1-yl]piperidin-4-yl]acetonitrile Chemical compound CS(=O)(=O)N1CCC(CC#N)(CC1)N1CC(CNC2CC2c2ccccc2)C1 NCGLLDRHTVMYPJ-UHFFFAOYSA-N 0.000 claims 1
- WAOKAHCYIMPPGD-UHFFFAOYSA-N 2-[3-(cyanomethyl)-3-[4-[(2-phenylcyclopropyl)amino]piperidin-1-yl]azetidin-1-yl]benzonitrile Chemical compound N#CCC1(CN(C1)c1ccccc1C#N)N1CCC(CC1)NC1CC1c1ccccc1 WAOKAHCYIMPPGD-UHFFFAOYSA-N 0.000 claims 1
- JDCIQSZZZCQWTA-UHFFFAOYSA-N 2-[3-(cyanomethyl)-3-[4-[(2-phenylcyclopropyl)amino]piperidin-1-yl]azetidin-1-yl]pyridine-3-carbonitrile Chemical compound N#CCC1(CN(C1)c1ncccc1C#N)N1CCC(CC1)NC1CC1c1ccccc1 JDCIQSZZZCQWTA-UHFFFAOYSA-N 0.000 claims 1
- KLWGXIYQXBIWJD-VQTJNVASSA-N 2-[3-(cyanomethyl)-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-1-yl]-N-methylacetamide Chemical compound C(#N)CC1(CN(C1)CC(=O)NC)N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1 KLWGXIYQXBIWJD-VQTJNVASSA-N 0.000 claims 1
- JXCHKGWNLZVMEZ-RBUKOAKNSA-N 2-[3-(cyanomethyl)-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-1-yl]acetamide Chemical compound C(#N)CC1(CN(C1)CC(=O)N)N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1 JXCHKGWNLZVMEZ-RBUKOAKNSA-N 0.000 claims 1
- PWIOSBYHMSARTI-UHFFFAOYSA-N 2-[3-(cyanomethyl)-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-1-yl]benzonitrile Chemical compound N#CCC1(CN(C1)c1ccccc1C#N)N1CCC(CNC2CC2c2ccccc2)CC1 PWIOSBYHMSARTI-UHFFFAOYSA-N 0.000 claims 1
- CTZRQHBOAPYTEO-UHFFFAOYSA-N 2-[3-(cyanomethyl)-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-1-yl]pyridine-3-carbonitrile Chemical compound N#CCC1(CN(C1)c1ncccc1C#N)N1CCC(CNC2CC2c2ccccc2)CC1 CTZRQHBOAPYTEO-UHFFFAOYSA-N 0.000 claims 1
- UXIYDZIOOUEJGJ-DLBZAZTESA-N 2-[3-[3-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]azetidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1(=CC=CC=C1)[C@H]1[C@@H](C1)NCC1CN(C1)C1(CNC1)CC#N UXIYDZIOOUEJGJ-DLBZAZTESA-N 0.000 claims 1
- BWGRVHGXZYCISM-MUMRKEEXSA-N 2-[3-[4-[[(1R)-2-(4-fluorophenyl)cyclopropyl]amino]piperidin-1-yl]-1-methylsulfonylazetidin-3-yl]acetonitrile Chemical compound CS(=O)(=O)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccc(F)cc1 BWGRVHGXZYCISM-MUMRKEEXSA-N 0.000 claims 1
- IIDCSONIAIQNMY-GFOWMXPYSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(1,2-thiazole-5-carbonyl)azetidin-3-yl]acetonitrile Chemical compound O=C(N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1)c1ccns1 IIDCSONIAIQNMY-GFOWMXPYSA-N 0.000 claims 1
- USUWNBOZHLVEAO-GFOWMXPYSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(1,3-thiazol-2-ylmethyl)azetidin-3-yl]acetic acid Chemical compound OC(=O)CC1(CN(Cc2nccs2)C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 USUWNBOZHLVEAO-GFOWMXPYSA-N 0.000 claims 1
- GHWJMOSGGHRPOZ-BPGUCPLFSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(1,3-thiazol-5-ylmethyl)azetidin-3-yl]acetic acid Chemical compound OC(=O)CC1(CN(Cc2cncs2)C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 GHWJMOSGGHRPOZ-BPGUCPLFSA-N 0.000 claims 1
- DEVUVKQKULAJNV-GFOWMXPYSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(1,3-thiazole-2-carbonyl)azetidin-3-yl]acetonitrile Chemical compound O=C(N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1)c1nccs1 DEVUVKQKULAJNV-GFOWMXPYSA-N 0.000 claims 1
- UMLNPHYCWGBJOH-GFOWMXPYSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(1,3-thiazole-4-carbonyl)azetidin-3-yl]acetonitrile Chemical compound O=C(N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1)c1cscn1 UMLNPHYCWGBJOH-GFOWMXPYSA-N 0.000 claims 1
- XGFPOLXECPYKPJ-GFOWMXPYSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(1,3-thiazole-5-carbonyl)azetidin-3-yl]acetonitrile Chemical compound O=C(N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1)c1cncs1 XGFPOLXECPYKPJ-GFOWMXPYSA-N 0.000 claims 1
- TYHVLCMAEMDYCP-BPGUCPLFSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(1H-pyrazole-4-carbonyl)azetidin-3-yl]acetonitrile Chemical compound O=C(N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1)c1cn[nH]c1 TYHVLCMAEMDYCP-BPGUCPLFSA-N 0.000 claims 1
- DAGXBMVVNPMYCV-VGAJERRHSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(1H-pyrazole-5-carbonyl)azetidin-3-yl]acetonitrile Chemical compound O=C(N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1)c1ccn[nH]1 DAGXBMVVNPMYCV-VGAJERRHSA-N 0.000 claims 1
- FMBNWGHWIFUXPF-XMMISQBUSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(2-pyridin-2-ylacetyl)azetidin-3-yl]acetonitrile Chemical compound O=C(Cc1ccccn1)N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 FMBNWGHWIFUXPF-XMMISQBUSA-N 0.000 claims 1
- WQPGXBJNMQFZEF-MUMRKEEXSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(3,3,3-trifluoropropyl)azetidin-3-yl]acetic acid Chemical compound OC(=O)CC1(CN(CCC(F)(F)F)C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 WQPGXBJNMQFZEF-MUMRKEEXSA-N 0.000 claims 1
- HGTYIFDNJSWEGV-BPGUCPLFSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(pyrazine-2-carbonyl)azetidin-3-yl]acetonitrile Chemical compound O=C(N1CC(CC#N)(C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1)c1cnccn1 HGTYIFDNJSWEGV-BPGUCPLFSA-N 0.000 claims 1
- PAODTXXDMLQHCY-BPGUCPLFSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(pyrimidin-2-ylmethyl)azetidin-3-yl]acetic acid Chemical compound OC(=O)CC1(CN(Cc2ncccn2)C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 PAODTXXDMLQHCY-BPGUCPLFSA-N 0.000 claims 1
- NLKWZDUQUSVPJL-FOIFJWKZSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]-1-(pyrimidin-5-ylmethyl)azetidin-3-yl]acetic acid Chemical compound OC(=O)CC1(CN(Cc2cncnc2)C1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 NLKWZDUQUSVPJL-FOIFJWKZSA-N 0.000 claims 1
- XVOKNSJVLHJVLS-QRWMCTBCSA-N 2-[3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound N#CCC1(CNC1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 XVOKNSJVLHJVLS-QRWMCTBCSA-N 0.000 claims 1
- MEHVWKKCGUIXNI-STTLMXHVSA-N 2-[3-[4-[[(1R,2S)-2-(4-fluorophenyl)cyclopropyl]amino]piperidin-1-yl]-1-(4-hydroxycyclohexyl)azetidin-3-yl]acetonitrile Chemical compound FC1=CC=C(C=C1)[C@H]1[C@@H](C1)NC1CCN(CC1)C1(CN(C1)C1CCC(CC1)O)CC#N MEHVWKKCGUIXNI-STTLMXHVSA-N 0.000 claims 1
- XVOKNSJVLHJVLS-ZWKOTPCHSA-N 2-[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(CNC1)CC#N XVOKNSJVLHJVLS-ZWKOTPCHSA-N 0.000 claims 1
- XVOKNSJVLHJVLS-MSOLQXFVSA-N 2-[3-[4-[[(1S,2R)-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(CNC1)CC#N XVOKNSJVLHJVLS-MSOLQXFVSA-N 0.000 claims 1
- TUXVOJPDNKEUES-UHFFFAOYSA-N 2-[3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]-1-[3-(trifluoromethyl)pyridin-2-yl]azetidin-3-yl]acetonitrile Chemical compound FC(F)(F)c1cccnc1N1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1 TUXVOJPDNKEUES-UHFFFAOYSA-N 0.000 claims 1
- ITMDMKOHSAXUAX-UHFFFAOYSA-N 2-[3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]-1-[5-(trifluoromethyl)pyridin-2-yl]azetidin-3-yl]acetonitrile Chemical compound FC(F)(F)c1ccc(nc1)N1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1 ITMDMKOHSAXUAX-UHFFFAOYSA-N 0.000 claims 1
- DOMHYKFZPPFFSW-UHFFFAOYSA-N 2-[3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-3-yl]acetic acid Chemical compound OC(=O)CC1(CNC1)N1CCC(CNC2CC2c2ccccc2)CC1 DOMHYKFZPPFFSW-UHFFFAOYSA-N 0.000 claims 1
- SFXSOHVWLSFZFW-UHFFFAOYSA-N 2-[3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-3-yl]acetonitrile Chemical compound N#CCC1(CNC1)N1CCC(CNC2CC2c2ccccc2)CC1 SFXSOHVWLSFZFW-UHFFFAOYSA-N 0.000 claims 1
- IADKUDSGXJARPU-RBUKOAKNSA-N 2-[4-[3-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]azetidin-1-yl]piperidin-4-yl]acetonitrile Chemical compound C1(=CC=CC=C1)[C@H]1[C@@H](C1)NCC1CN(C1)C1(CCNCC1)CC#N IADKUDSGXJARPU-RBUKOAKNSA-N 0.000 claims 1
- VFHTVJZMYGMJST-UHFFFAOYSA-N 2-chloro-6-[3-(cyanomethyl)-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-1-yl]benzonitrile Chemical compound Clc1cccc(N2CC(CC#N)(C2)N2CCC(CNC3CC3c3ccccc3)CC2)c1C#N VFHTVJZMYGMJST-UHFFFAOYSA-N 0.000 claims 1
- XOABJLMYTOAXDU-UHFFFAOYSA-N 2-phenyl-N-[[1-(1-phenylpiperidin-4-yl)azetidin-3-yl]methyl]cyclopropan-1-amine Chemical compound C(NC1CC1c1ccccc1)C1CN(C1)C1CCN(CC1)c1ccccc1 XOABJLMYTOAXDU-UHFFFAOYSA-N 0.000 claims 1
- GLXPUBZSNUMXBZ-ZWKOTPCHSA-N 3-(cyanomethyl)-3-[4-[[(1R,2S)-2-(4-fluorophenyl)cyclopropyl]amino]piperidin-1-yl]azetidine-1-sulfonamide Chemical compound C(#N)CC1(CN(C1)S(=O)(=O)N)N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=C(C=C1)F GLXPUBZSNUMXBZ-ZWKOTPCHSA-N 0.000 claims 1
- GMBKWWMGXRBRKT-ZWKOTPCHSA-N 3-(cyanomethyl)-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidine-1-sulfonamide Chemical compound C(#N)CC1(CN(C1)S(=O)(=O)N)N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1 GMBKWWMGXRBRKT-ZWKOTPCHSA-N 0.000 claims 1
- AQLWLNLLRWETFZ-VQTJNVASSA-N 3-(cyanomethyl)-N,N-dimethyl-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidine-1-sulfonamide Chemical compound C(#N)CC1(CN(C1)S(=O)(=O)N(C)C)N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1 AQLWLNLLRWETFZ-VQTJNVASSA-N 0.000 claims 1
- QFHDHMBBBAWCFI-UHFFFAOYSA-N 3-(cyanomethyl)-N-(2,4-difluorophenyl)-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidine-1-carboxamide Chemical compound Fc1ccc(NC(=O)N2CC(CC#N)(C2)N2CCC(CNC3CC3c3ccccc3)CC2)c(F)c1 QFHDHMBBBAWCFI-UHFFFAOYSA-N 0.000 claims 1
- VJCRHXYGKIEQEH-RBUKOAKNSA-N 3-(cyanomethyl)-N-methyl-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidine-1-sulfonamide Chemical compound C(#N)CC1(CN(C1)S(=O)(=O)NC)N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1 VJCRHXYGKIEQEH-RBUKOAKNSA-N 0.000 claims 1
- ZKXDFFPSTBNTFS-LEWJYISDSA-N 3-[2-(dimethylamino)-2-oxoethyl]-N,N-dimethyl-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidine-1-carboxamide Chemical compound CN(C(CC1(CN(C1)C(=O)N(C)C)N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)=O)C ZKXDFFPSTBNTFS-LEWJYISDSA-N 0.000 claims 1
- RWNJNROHWPRAPM-VQTJNVASSA-N 3-[3-(cyanomethyl)-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-1-yl]propanoic acid Chemical compound C(#N)CC1(CN(C1)CCC(=O)O)N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1 RWNJNROHWPRAPM-VQTJNVASSA-N 0.000 claims 1
- VUGJEBCUYKUMNE-UHFFFAOYSA-N 3-cyano-4-[3-(cyanomethyl)-3-[4-[(2-phenylcyclopropyl)amino]piperidin-1-yl]azetidin-1-yl]benzoic acid Chemical compound C(#N)C=1C=C(C(=O)O)C=CC=1N1CC(C1)(N1CCC(CC1)NC1C(C1)C1=CC=CC=C1)CC#N VUGJEBCUYKUMNE-UHFFFAOYSA-N 0.000 claims 1
- GZYXUPOSMJNNNG-UHFFFAOYSA-N 4-(cyanomethyl)-4-[3-[[(2-phenylcyclopropyl)amino]methyl]azetidin-1-yl]-N-propan-2-ylpiperidine-1-carboxamide Chemical compound CC(C)NC(=O)N1CCC(CC#N)(CC1)N1CC(CNC2CC2c2ccccc2)C1 GZYXUPOSMJNNNG-UHFFFAOYSA-N 0.000 claims 1
- NOQVNHUJKIVFEW-UHFFFAOYSA-N 4-(cyanomethyl)-N,N-dimethyl-4-[3-[[(2-phenylcyclopropyl)amino]methyl]azetidin-1-yl]piperidine-1-carboxamide Chemical compound CN(C)C(=O)N1CCC(CC#N)(CC1)N1CC(CNC2CC2c2ccccc2)C1 NOQVNHUJKIVFEW-UHFFFAOYSA-N 0.000 claims 1
- JPPOIZFRLNQZDJ-UHFFFAOYSA-N 4-(cyanomethyl)-N-(4-fluorophenyl)-4-[3-[[(2-phenylcyclopropyl)amino]methyl]azetidin-1-yl]piperidine-1-carboxamide Chemical compound Fc1ccc(NC(=O)N2CCC(CC#N)(CC2)N2CC(CNC3CC3c3ccccc3)C2)cc1 JPPOIZFRLNQZDJ-UHFFFAOYSA-N 0.000 claims 1
- CVXHLUSQNWCTAM-UHFFFAOYSA-N 4-[3-(cyanomethyl)-3-[4-[(2-phenylcyclopropyl)amino]piperidin-1-yl]azetidin-1-yl]benzonitrile Chemical compound N#CCC1(CN(C1)c1ccc(cc1)C#N)N1CCC(CC1)NC1CC1c1ccccc1 CVXHLUSQNWCTAM-UHFFFAOYSA-N 0.000 claims 1
- SIOQWJTYOGOHDJ-UHFFFAOYSA-N 4-[3-(cyanomethyl)-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-1-yl]-2,5-difluoro-N-propan-2-ylbenzamide Chemical compound CC(C)NC(=O)c1cc(F)c(cc1F)N1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1 SIOQWJTYOGOHDJ-UHFFFAOYSA-N 0.000 claims 1
- LDQZIOZDTIHCGW-UHFFFAOYSA-N 4-[3-(cyanomethyl)-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-1-yl]benzonitrile Chemical compound N#CCC1(CN(C1)c1ccc(cc1)C#N)N1CCC(CNC2CC2c2ccccc2)CC1 LDQZIOZDTIHCGW-UHFFFAOYSA-N 0.000 claims 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 1
- 206010005949 Bone cancer Diseases 0.000 claims 1
- 208000018084 Bone neoplasm Diseases 0.000 claims 1
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims 1
- 102100021519 Hemoglobin subunit beta Human genes 0.000 claims 1
- 108091005904 Hemoglobin subunit beta Proteins 0.000 claims 1
- 208000017604 Hodgkin disease Diseases 0.000 claims 1
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 1
- 101001050886 Homo sapiens Lysine-specific histone demethylase 1A Proteins 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 102100024985 Lysine-specific histone demethylase 1A Human genes 0.000 claims 1
- 208000025205 Mantle-Cell Lymphoma Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 206010028570 Myelopathy Diseases 0.000 claims 1
- JBMXDXFJXJLJSZ-XMMISQBUSA-N N,N-dimethyl-2-[1-(oxan-4-yl)-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetamide Chemical compound CN(C)C(=O)CC1(CN(C1)C1CCOCC1)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 JBMXDXFJXJLJSZ-XMMISQBUSA-N 0.000 claims 1
- LHQXFINMYQORHT-VQTJNVASSA-N N,N-dimethyl-2-[1-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]cyclobutyl]acetamide Chemical compound CN(C(CC1(CCC1)N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)=O)C LHQXFINMYQORHT-VQTJNVASSA-N 0.000 claims 1
- QMCGPOOLGHNHTJ-LEWJYISDSA-N N,N-dimethyl-2-[1-[4-methyl-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]cyclobutyl]acetamide Chemical compound CN(C(CC1(CCC1)N1CCC(CC1)(CN[C@H]1[C@@H](C1)C1=CC=CC=C1)C)=O)C QMCGPOOLGHNHTJ-LEWJYISDSA-N 0.000 claims 1
- OINBUCHQWKHXGE-GFOWMXPYSA-N N,N-dimethyl-2-[1-methylsulfonyl-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetamide Chemical compound CN(C)C(=O)CC1(CN(C1)S(C)(=O)=O)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 OINBUCHQWKHXGE-GFOWMXPYSA-N 0.000 claims 1
- NNGVVKXEUSNXHF-VQTJNVASSA-N N,N-dimethyl-3-[2-(methylamino)-2-oxoethyl]-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidine-1-carboxamide Chemical compound CN(C(=O)N1CC(C1)(N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)CC(=O)NC)C NNGVVKXEUSNXHF-VQTJNVASSA-N 0.000 claims 1
- MNXLPLGILREJMI-UHFFFAOYSA-N N-(3-chloro-2-fluorophenyl)-3-(cyanomethyl)-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidine-1-carboxamide Chemical compound Fc1c(Cl)cccc1NC(=O)N1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1 MNXLPLGILREJMI-UHFFFAOYSA-N 0.000 claims 1
- NRMYICXRCKYDGH-RBUKOAKNSA-N N-methyl-2-[1-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]cyclobutyl]acetamide Chemical compound CNC(CC1(CCC1)N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)=O NRMYICXRCKYDGH-RBUKOAKNSA-N 0.000 claims 1
- CALXIMFKIFKIMQ-VQTJNVASSA-N N-methyl-2-[1-[4-methyl-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]cyclobutyl]acetamide Chemical compound CNC(CC1(CCC1)N1CCC(CC1)(CN[C@H]1[C@@H](C1)C1=CC=CC=C1)C)=O CALXIMFKIFKIMQ-VQTJNVASSA-N 0.000 claims 1
- NKLIIIQKMHWWRE-MUMRKEEXSA-N N-methyl-2-[1-methylsulfonyl-3-[4-[[(1R)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidin-3-yl]acetamide Chemical compound CNC(=O)CC1(CN(C1)S(C)(=O)=O)N1CCC(CC1)N[C@@H]1CC1c1ccccc1 NKLIIIQKMHWWRE-MUMRKEEXSA-N 0.000 claims 1
- CNQGUUGQPWCPFS-UHFFFAOYSA-N N-methyl-2-[3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidin-3-yl]acetamide Chemical compound CNC(=O)CC1(CNC1)N1CCC(CNC2CC2c2ccccc2)CC1 CNQGUUGQPWCPFS-UHFFFAOYSA-N 0.000 claims 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- 208000008385 Urogenital Neoplasms Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- JPTGAPQWKGYFGD-UHFFFAOYSA-N ethyl 4-(cyanomethyl)-4-[3-[[(2-phenylcyclopropyl)amino]methyl]azetidin-1-yl]piperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(CC#N)(CC1)N1CC(CNC2CC2c2ccccc2)C1 JPTGAPQWKGYFGD-UHFFFAOYSA-N 0.000 claims 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- DQDYFFXIISPDLN-RBUKOAKNSA-N methyl 3-(cyanomethyl)-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidine-1-carboxylate Chemical compound C(#N)CC1(CN(C1)C(=O)OC)N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1 DQDYFFXIISPDLN-RBUKOAKNSA-N 0.000 claims 1
- KSSGLLPOBYMBQL-UHFFFAOYSA-N methyl 3-(cyanomethyl)-3-[4-[[(2-phenylcyclopropyl)amino]methyl]piperidin-1-yl]azetidine-1-carboxylate Chemical compound COC(=O)N1CC(CC#N)(C1)N1CCC(CNC2CC2c2ccccc2)CC1 KSSGLLPOBYMBQL-UHFFFAOYSA-N 0.000 claims 1
- YGYJDIMVBSOMLI-VQTJNVASSA-N methyl 3-[2-(dimethylamino)-2-oxoethyl]-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidine-1-carboxylate Chemical compound CN(C(CC1(CN(C1)C(=O)OC)N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)=O)C YGYJDIMVBSOMLI-VQTJNVASSA-N 0.000 claims 1
- XTENMDFQBUVJMC-RBUKOAKNSA-N methyl 3-[2-(methylamino)-2-oxoethyl]-3-[4-[[(1R,2S)-2-phenylcyclopropyl]amino]piperidin-1-yl]azetidine-1-carboxylate Chemical compound CNC(CC1(CN(C1)C(=O)OC)N1CCC(CC1)N[C@H]1[C@@H](C1)C1=CC=CC=C1)=O XTENMDFQBUVJMC-RBUKOAKNSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 201000011682 nervous system cancer Diseases 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461939458P | 2014-02-13 | 2014-02-13 | |
| US61/939,458 | 2014-02-13 | ||
| US201462061258P | 2014-10-08 | 2014-10-08 | |
| US62/061,258 | 2014-10-08 | ||
| PCT/US2015/015635 WO2015123424A1 (en) | 2014-02-13 | 2015-02-12 | Cyclopropylamines as lsd1 inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019186168A Division JP6781815B2 (ja) | 2014-02-13 | 2019-10-09 | Ｌｓｄ１阻害剤としてのシクロプロピルアミン類 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017510555A JP2017510555A (ja) | 2017-04-13 |
| JP2017510555A5 true JP2017510555A5 (cg-RX-API-DMAC7.html) | 2018-03-29 |
| JP6602779B2 JP6602779B2 (ja) | 2019-11-06 |
Family
ID=52595463
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016551815A Active JP6602779B2 (ja) | 2014-02-13 | 2015-02-12 | Ｌｓｄ１阻害剤としてのシクロプロピルアミン類 |
| JP2019186168A Active JP6781815B2 (ja) | 2014-02-13 | 2019-10-09 | Ｌｓｄ１阻害剤としてのシクロプロピルアミン類 |
| JP2020174661A Pending JP2021011496A (ja) | 2014-02-13 | 2020-10-16 | Ｌｓｄ１阻害剤としてのシクロプロピルアミン類 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019186168A Active JP6781815B2 (ja) | 2014-02-13 | 2019-10-09 | Ｌｓｄ１阻害剤としてのシクロプロピルアミン類 |
| JP2020174661A Pending JP2021011496A (ja) | 2014-02-13 | 2020-10-16 | Ｌｓｄ１阻害剤としてのシクロプロピルアミン類 |
Country Status (35)
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6602779B2 (ja) | 2014-02-13 | 2019-11-06 | インサイト・コーポレイション | Ｌｓｄ１阻害剤としてのシクロプロピルアミン類 |
| US9493442B2 (en) | 2014-02-13 | 2016-11-15 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| US9527835B2 (en) | 2014-02-13 | 2016-12-27 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| CN106164066B (zh) | 2014-02-13 | 2020-01-17 | 因赛特公司 | 作为lsd1抑制剂的环丙胺 |
| US9346776B2 (en) | 2014-02-13 | 2016-05-24 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compound |
| US9428470B2 (en) | 2014-02-13 | 2016-08-30 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| US9695168B2 (en) | 2014-07-10 | 2017-07-04 | Incyte Corporation | Substituted imidazo[1,5-α]pyridines and imidazo[1,5-α]pyrazines as LSD1 inhibitors |
| WO2016007727A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| TW201613925A (en) | 2014-07-10 | 2016-04-16 | Incyte Corp | Imidazopyrazines as LSD1 inhibitors |
| CN107660205B (zh) | 2015-04-03 | 2021-08-27 | 因赛特公司 | 作为lsd1抑制剂的杂环化合物 |
| US20180284095A1 (en) | 2015-06-12 | 2018-10-04 | Oryzon Genomics, S.A. | Biomarkers associated with lsd1 inhibitors and uses thereof |
| WO2017013061A1 (en) | 2015-07-17 | 2017-01-26 | Oryzon Genomics, S.A. | Biomarkers associated with lsd1 inhibitors and uses thereof |
| EA035534B1 (ru) | 2015-08-12 | 2020-06-30 | Инсайт Корпорейшн | Соли ингибитора lsd1 |
| US10059668B2 (en) | 2015-11-05 | 2018-08-28 | Mirati Therapeutics, Inc. | LSD1 inhibitors |
| SG11201805645QA (en) | 2015-12-29 | 2018-07-30 | Mirati Therapeutics Inc | Lsd1 inhibitors |
| CA3017411C (en) | 2016-03-15 | 2024-06-25 | Oryzon Genomics, S.A. | Combinations of lsd1 inhibitors for use in the treatment of solid tumors |
| EP3430015B9 (en) | 2016-03-16 | 2025-12-31 | Oryzon Genomics, S.A. | METHODS FOR DETERMINING THE ENGAGEMENT OF A KDM1A TARGET AND CORRESPONDING USEFUL CHEMOPROBE |
| 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 |
| BR112018071585B1 (pt) | 2016-04-22 | 2024-01-02 | Incyte Corporation | Formulações de um inibidor de lsd1, seus usos e método de preparação das mesmas |
| 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 |
| WO2018083138A1 (en) | 2016-11-03 | 2018-05-11 | Oryzon Genomics, S.A. | Pharmacodynamic biomarkers for personalized cancer care using epigenetic modifying agents |
| US20190256930A1 (en) | 2016-11-03 | 2019-08-22 | Oryzon Genomics, S.A. | Biomarkers for determining responsiveness to lsd1 inhibitors |
| JP7352284B2 (ja) | 2017-05-15 | 2023-09-28 | ザ・リージェンツ・オブ・ザ・ユニバーシティ・オブ・ミシガン | ＬＳＤ－１インヒビターとしてのピロロ〔２，３－ｃ〕ピリジン及び関連類似体 |
| AU2018309372B2 (en) | 2017-08-03 | 2024-08-15 | Oryzon Genomics, S.A. | Methods of treating behavior alterations |
| WO2019068326A1 (en) | 2017-10-05 | 2019-04-11 | Université D'aix-Marseille | INHIBITORS OF LSD1 FOR THE TREATMENT AND PREVENTION OF CARDIOMYOPATHIES |
| WO2019222069A1 (en) | 2018-05-15 | 2019-11-21 | The Regents Of The University Of Michigan | Imidazo[4,5-c]pyridine compounds as lsd-1 inhibitors |
| US10968200B2 (en) | 2018-08-31 | 2021-04-06 | Incyte Corporation | Salts of an LSD1 inhibitor and processes for preparing the same |
| AU2019387370A1 (en) | 2018-11-30 | 2021-06-10 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| CN113631164A (zh) | 2019-03-20 | 2021-11-09 | 奥莱松基因组股份有限公司 | 使用kdm1a抑制剂如化合物伐菲德司他治疗注意缺陷多动症的方法 |
| AU2020242302B2 (en) | 2019-03-20 | 2025-10-30 | Oryzon Genomics, S.A. | Methods of treating borderline personality disorder |
| JP2022546908A (ja) | 2019-07-05 | 2022-11-10 | オリゾン・ゲノミクス・ソシエダッド・アノニマ | Ｋｄｍ１ａ阻害剤を使用した小細胞肺がんの個別化された処置のためのバイオマーカーおよび方法 |
| 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 |
| AU2022254484A1 (en) | 2021-04-08 | 2023-11-09 | Oryzon Genomics, S.A. | Combinations of lsd1 inhibitors for treating myeloid cancers |
| WO2023217758A1 (en) | 2022-05-09 | 2023-11-16 | Oryzon Genomics, S.A. | Methods of treating malignant peripheral nerve sheath tumor (mpnst) using lsd1 inhibitors |
| JP2025516648A (ja) | 2022-05-09 | 2025-05-30 | オリゾン・ゲノミクス・ソシエダッド・アノニマ | Ｌｓｄ１阻害薬を用いるｎｆ１変異腫瘍の治療法 |
| KR20250109775A (ko) | 2022-11-24 | 2025-07-17 | 오리존 지노믹스 에스.에이. | 암 치료를 위한 lsd1 억제제 및 메닌 억제제의 조합 |
| 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 |
| WO2025080946A2 (en) | 2023-10-12 | 2025-04-17 | 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 |
| WO2025255438A1 (en) | 2024-06-07 | 2025-12-11 | Revolution Medicines, Inc. | Methods of treating a ras protein-related disease or disorder |
Family Cites Families (316)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7013068A (cg-RX-API-DMAC7.html) | 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 (cg-RX-API-DMAC7.html) | 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 |
| TR200001728T2 (tr) | 1997-11-11 | 2000-09-21 | Ono Pharmaceutical Co., Ltd. | Birleşik pirazin türevleri |
| 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 |
| MXPA02003321A (es) | 1999-09-28 | 2004-09-10 | Panacea Biotec Ltd | Composiciones de liberacion controlada que comprenden nimesulida. |
| 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 |
| CA2407573C (en) | 2000-04-27 | 2011-09-13 | Yamanouchi Pharmaceutical Co. Ltd. | Imidazopyridine derivatives |
| US6403588B1 (en) | 2000-04-27 | 2002-06-11 | Yamanouchi Pharmaceutical Co., Ltd. | Imidazopyridine derivatives |
| AU2002215608B2 (en) | 2000-06-28 | 2004-12-09 | Smithkline Beecham P.L.C. | Wet milling process |
| AR029538A1 (es) | 2000-07-06 | 2003-07-02 | Wyeth Corp | Composiciones farmaceuticas de agentes estrogenicos |
| JP2004532792A (ja) | 2000-07-14 | 2004-10-28 | ブリストル−マイヤーズ・スクイブ・ファーマ・カンパニー | 神経障害を治療するためのイミダゾ［１，２−ａ］ピラジン |
| 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 |
| ATE310740T1 (de) | 2000-11-10 | 2005-12-15 | Merck Sharp & Dohme | Imidazotriazin-derivate als liganden für gaba- rezeptoren |
| AU2002224927A1 (en) | 2000-12-13 | 2002-06-24 | Basf Aktiengesellschaft | Use of substituted imidazoazines, novel imidazoazines, methods for the production thereof, and agents containing these compounds |
| 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 |
| EP1513522A2 (en) | 2002-01-18 | 2005-03-16 | Sri International | Methods of treating conditions associated with an edg receptor |
| US20050113283A1 (en) | 2002-01-18 | 2005-05-26 | David Solow-Cordero | Methods of treating conditions associated with an EDG-4 receptor |
| 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 |
| WO2005014777A2 (en) | 2002-10-16 | 2005-02-17 | Board Of Regents, The University Of Texas System | Methods and compositions for increasing the efficacy of biologically-active ingredients |
| MXPA05006568A (es) | 2002-12-20 | 2005-09-22 | Pharmacia Corp | Compuestos de pirazol aciclico para la inhibicion de proteina cinasa-2 activada por proteina cinasa activada por mitogenos. |
| WO2004072080A1 (en) | 2003-02-10 | 2004-08-26 | Cellular Genomics, Inc. | Certain 8-heteroaryl-6-phenyl-imidazo[1,2-a]pyrazines as modulators of hsp90 complex 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 |
| TW201018661A (en) | 2003-03-14 | 2010-05-16 | Ono Pharmaceutical Co | Heterocyclic rinf having nitrogen atom derivatives and medicament containing the derivatives as active ingredient |
| WO2004089380A2 (en) | 2003-04-11 | 2004-10-21 | Novo Nordisk A/S | Pharmaceutical use of fused 1,2,4-triazoles |
| 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 |
| US7579355B2 (en) | 2003-04-24 | 2009-08-25 | Merck & Co., Inc. | Inhibitors of Akt activity |
| SE0301653D0 (sv) | 2003-06-05 | 2003-06-05 | Astrazeneca Ab | Novel compounds |
| WO2005007658A2 (en) | 2003-07-14 | 2005-01-27 | Arena Pharmaceuticals, Inc. | Fused-aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto |
| US7538120B2 (en) | 2003-09-03 | 2009-05-26 | Array Biopharma Inc. | Method of treating inflammatory diseases |
| ES2385219T3 (es) | 2003-09-12 | 2012-07-19 | Merck Serono Sa | Derivados de sulfonamida para el tratamiento de diabetes |
| 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 |
| WO2005044793A2 (en) | 2003-10-31 | 2005-05-19 | Takeda Pharmaceutical Company Limited | Nitrogen-containing fused heterocyclic compounds |
| EP1698335A4 (en) | 2003-12-26 | 2007-08-01 | Ono Pharmaceutical Co | AGENT FOR PREVENTING AND / OR TREATING DISEASES INVOLVING A MITOCHONDRIAL BENZODIAZEPINE RECEPTOR |
| JPWO2005077948A1 (ja) | 2004-02-16 | 2008-01-10 | 第一製薬株式会社 | 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 |
| MXPA06012449A (es) * | 2004-04-26 | 2007-01-17 | Pfizer | Inhibidores de la enzima integrasa de vih. |
| 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 |
| EP1781655A2 (en) | 2004-08-18 | 2007-05-09 | Pharmacia & Upjohn Company LLC | Triazolopyridine compounds useful for the treatment of inflammation |
| MX2007002679A (es) | 2004-09-02 | 2007-05-16 | Smithkline Beecham Corp | Compuestos quimicos. |
| MX2007004179A (es) | 2004-10-07 | 2007-06-07 | Warner Lambert Co | Derivados de triazolpiridina como agentes antibacterianos. |
| AU2005309761A1 (en) | 2004-11-22 | 2006-06-01 | Threshold Pharmaceuticals, Inc. | Tubulin binding anti cancer agents and prodrugs thereof |
| JP2008521858A (ja) | 2004-12-01 | 2008-06-26 | ラボラトワール セローノ ソシエテ アノニム | 過増殖性疾患を処置するための［１，２，４］トリアゾロ［４，３−ａ］ピリジン誘導体 |
| WO2007149479A1 (en) | 2006-06-22 | 2007-12-27 | Mallinckrodt Inc. | Pyrazine derivatives and uses thereof in renal monitoring |
| 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 |
| GEP20094727B (en) | 2005-02-22 | 2009-07-10 | Pfizer | Oxyindole derivatives as 5ht4 receptor agonists |
| ITBO20050123A1 (it) | 2005-03-07 | 2005-06-06 | Alfa Wassermann Spa | Formulazioni farmaceutiche gastroresistenti contenenti rifaximina |
| AR053712A1 (es) | 2005-04-18 | 2007-05-16 | Neurogen Corp | Heteroarilos sustituidos, antagonistas de cb1 (receptor 1 canabinoide) |
| US7572807B2 (en) | 2005-06-09 | 2009-08-11 | Bristol-Myers Squibb Company | Heteroaryl 11-beta-hydroxysteroid dehydrogenase type I inhibitors |
| AU2005332594A1 (en) | 2005-06-09 | 2006-12-14 | Oncalis Ag | Angiogenesis inhibitors |
| US7579360B2 (en) | 2005-06-09 | 2009-08-25 | Bristol-Myers Squibb Company | Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| 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 |
| CA2620223A1 (en) | 2005-09-02 | 2007-03-08 | Abbott Laboratories | Novel imidazo based heterocycles |
| WO2007032936A2 (en) | 2005-09-09 | 2007-03-22 | Schering Corporation | Azafused cyclin dependent kinase inhibitors |
| US20070117804A1 (en) | 2005-11-10 | 2007-05-24 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| EA017290B1 (ru) | 2005-11-28 | 2012-11-30 | Домейн Раша Инвестментс Лимитед | Композиции на основе ганаксолона |
| BRPI0620760A2 (pt) | 2005-12-27 | 2011-11-22 | Hoffmann La Roche | derivados de aril-isoxazol-4-il-imidazo[1,5]piridina |
| 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) |
| KR20080104351A (ko) | 2006-03-31 | 2008-12-02 | 노파르티스 아게 | 유기 화합물 |
| US20090175852A1 (en) | 2006-06-06 | 2009-07-09 | Schering Corporation | Imidazopyrazines as protein kinase inhibitors |
| TW200808802A (en) | 2006-06-06 | 2008-02-16 | Schering Corp | Imidazopyrazines as protein kinase inhibitors |
| US9216963B2 (en) | 2006-06-22 | 2015-12-22 | Medibeacon Inc. | Pyrazine derivatives with extended conjugation and methods of using the same in optical applications |
| MX2009000107A (es) | 2006-06-29 | 2009-01-23 | Schering Corp | Antagonistas del receptor de trombina biciclicos y triciclicos sustituidos. |
| WO2008005423A1 (en) | 2006-07-03 | 2008-01-10 | Cambrex Charles City, Inc. | Improved method of making sufentanil |
| WO2008005908A2 (en) | 2006-07-07 | 2008-01-10 | Forest Laboratories Holdings Limited | Pyridoimidazole derivatives |
| US8217177B2 (en) | 2006-07-14 | 2012-07-10 | Amgen Inc. | Fused heterocyclic derivatives and methods of use |
| US8198448B2 (en) | 2006-07-14 | 2012-06-12 | Amgen Inc. | Fused heterocyclic derivatives and methods of use |
| PE20080403A1 (es) | 2006-07-14 | 2008-04-25 | Amgen Inc | Derivados heterociclicos fusionados y metodos de uso |
| US20080021026A1 (en) | 2006-07-20 | 2008-01-24 | 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 |
| EP2086973B1 (en) | 2006-10-11 | 2012-01-25 | 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 |
| AU2007323725B2 (en) | 2006-11-22 | 2014-02-20 | Incyte Holdings Corporation | Imidazotriazines and imidazopyrimidines as kinase inhibitors |
| US7977352B2 (en) | 2006-12-01 | 2011-07-12 | Galapagos Nv | Triazolopyridine compounds useful for the treatment of degenerative and inflammatory diseases |
| US20100316712A1 (en) | 2006-12-22 | 2010-12-16 | Combinatorx, Incorporated | Pharmaceutical compositions for treatment of parkinson's disease and related disorders |
| DK2118101T3 (da) | 2007-03-09 | 2013-01-02 | Probiodrug Ag | IMIDAZO (1,5-A)-PYRIDinderivater som glutaminylcyclaseinhibitorer |
| 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 |
| ATE540037T1 (de) | 2007-04-16 | 2012-01-15 | Leo Pharma As | Triazolopyridine als phosphodiesterasehemmer zur behandlung von hautkrankheiten |
| US8546394B2 (en) | 2007-04-17 | 2013-10-01 | Bristol-Myers Squibb Company | Substituted [1,2,4]triazolo[4,3-A]pyrazine 11-beta-hydroxysteroid dehydrogenase inhibitors |
| US20110206607A1 (en) | 2007-05-10 | 2011-08-25 | Roger Olsson | Imidazol (1,2-a)pyridines and related compounds with activity at cannabinoid cb2 receptors |
| ES2648037T3 (es) | 2007-05-21 | 2017-12-28 | Toray Industries, Inc. | Preparación oral que comprende un ácido orgánico específico y método para mejorar la propiedad de disolución y la estabilidad química de la preparación oral |
| WO2008154241A1 (en) | 2007-06-08 | 2008-12-18 | Abbott Laboratories | 5-heteroaryl substituted indazoles as kinase inhibitors |
| US8648069B2 (en) | 2007-06-08 | 2014-02-11 | Abbvie Inc. | 5-substituted indazoles as kinase inhibitors |
| CN101772500A (zh) | 2007-06-14 | 2010-07-07 | 先灵公司 | 作为蛋白质激酶抑制剂的咪唑并吡嗪 |
| 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 |
| MX2010000716A (es) | 2007-07-18 | 2010-03-26 | Novartis Ag | Compuestos de heteroarilo biciclicos y su uso como inhibidores de cinasa. |
| AU2008282885A1 (en) | 2007-07-31 | 2009-02-05 | Schering Corporation | Anti-mitotic agent and aurora kinase inhibitor combination as anti-cancer treatment |
| WO2009017954A1 (en) | 2007-08-01 | 2009-02-05 | Phenomix Corporation | Inhibitors of jak2 kinase |
| CN101842098A (zh) | 2007-08-10 | 2010-09-22 | 基因实验室技术有限公司 | 用于治疗病毒感染的含氮的二环化学实体 |
| 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 |
| PL2201012T3 (pl) | 2007-10-11 | 2014-11-28 | Astrazeneca Ab | Pochodne pirolo[2,3-d]pirymidyny jako inhibitory kinazy białkowej b |
| EP3120833A1 (en) | 2007-10-12 | 2017-01-25 | Novartis Ag | Compositions comprising sphingosine 1 phosphate (s1p) receptor modulators |
| CA2710194C (en) | 2007-12-19 | 2014-04-22 | Amgen Inc. | Inhibitors of p13 kinase |
| RU2498985C2 (ru) | 2007-12-19 | 2013-11-20 | Дженентек, Инк. | 8-анилиноимидазопиридины и способы их использования |
| KR100988233B1 (ko) | 2007-12-26 | 2010-10-18 | 한미홀딩스 주식회사 | 클로피도그렐 1,5-나프탈렌 다이술폰산 염 또는 이의수화물의 약학 조성물 및 제제 |
| NZ587928A (en) | 2008-03-11 | 2012-08-31 | Incyte Corp | Azetidine and cyclobutane derivatives as jak inhibitors |
| US8507501B2 (en) | 2008-03-13 | 2013-08-13 | The Brigham And Women's Hospital, Inc. | Inhibitors of the BMP signaling pathway |
| JP5547099B2 (ja) | 2008-03-14 | 2014-07-09 | インテリカイン， エルエルシー | キナーゼ阻害剤および使用方法 |
| 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 |
| WO2010010184A1 (en) | 2008-07-25 | 2010-01-28 | Galapagos Nv | [1, 2, 4] triazolo [1, 5-a] pyridines as jak inhibitors |
| 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 |
| 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 |
| WO2010043721A1 (en) | 2008-10-17 | 2010-04-22 | 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 |
| DK2376490T3 (da) | 2008-12-04 | 2013-04-15 | Proximagen Ltd | Imidazopyridinforbindelser |
| 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 |
| EP2393813B1 (en) | 2009-02-04 | 2013-07-31 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11 ß-hydroxysteroid dehydrogenase 1 useful for the treatment of diseases related to elevated level of cortisol |
| US20100209489A1 (en) | 2009-02-04 | 2010-08-19 | Supernus Pharmaceuticals, Inc. | Formulations of desvenlafaxine |
| 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 |
| WO2010091824A1 (en) | 2009-02-13 | 2010-08-19 | Bayer Schering Pharma Aktiengesellschaft | Fused pyrimidines as akt inhibitors |
| KR20100101054A (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 |
| KR101772963B1 (ko) | 2009-03-31 | 2017-08-31 | 깃세이 야쿠힌 고교 가부시키가이샤 | 인돌리진 유도체 및 그 의약용도 |
| AU2010238361B2 (en) | 2009-04-16 | 2015-08-06 | Fundacion Centro Nacional De Investigaciones Oncologicas Carlos Iii | Imidazopyrazines for use as kinase inhibitors |
| TWI461426B (zh) | 2009-05-27 | 2014-11-21 | Merck Sharp & Dohme | （二氫）咪唑並異〔５，１－ａ〕喹啉類 |
| CN102803268A (zh) | 2009-06-10 | 2012-11-28 | 桑诺维恩药品公司 | 组胺h3反相激动剂和拮抗剂及其使用方法 |
| JP5732453B2 (ja) | 2009-06-25 | 2015-06-10 | アルカーメス ファーマ アイルランド リミテッド | Ｎｈ酸性化合物のプロドラッグ |
| AU2010284254B2 (en) | 2009-08-17 | 2015-09-17 | Intellikine, Llc | Heterocyclic compounds and uses thereof |
| EP2467359A4 (en) | 2009-08-18 | 2013-01-09 | Univ Johns Hopkins | (BIS-) UREA- AND (BIS-) THIOMINE COMPOUNDS AS EPIGENE MODULATORS OF THE LYSINE-SPECIFIC DEMETHYLASE 1 AND METHODS OF DISEASE TREATMENT THEREWITH |
| WO2011033265A1 (en) | 2009-09-18 | 2011-03-24 | Almac Discovery Limited | Pharmaceutical compounds |
| BR112012006572A2 (pt) | 2009-09-25 | 2016-04-26 | Oryzon Genomics Sa | inibidores de demetilase-1 de lisina específicos e seu uso |
| WO2011042217A1 (en) | 2009-10-09 | 2011-04-14 | 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 |
| EP2526102B1 (en) | 2010-01-22 | 2017-03-08 | Fundación Centro Nacional de Investigaciones Oncológicas Carlos III | Inhibitors of PI3 kinase |
| US20130085133A1 (en) | 2010-02-08 | 2013-04-04 | Sourthern Research Institute Office of Commercialization and Intellectual Prop. | Anti-viral treatment and assay to screenfor anti-viral agent |
| WO2011106573A2 (en) | 2010-02-24 | 2011-09-01 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with hepadnaviridae |
| 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 |
| 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 |
| CA2793086C (en) | 2010-03-18 | 2018-08-21 | Institut Pasteur Korea | Substituted imidazo[1,2-a]pyridine compounds and their use in the treatment of bacterial infections |
| SI2552920T1 (sl) | 2010-04-02 | 2017-07-31 | Ogeda Sa | Nove nk-3 receptor selektivne antagonist spojine, farmacevtski sestavki in postopki za uporabo pri nk-3 receptor posredovanih motnjah |
| AU2011244325B2 (en) | 2010-04-19 | 2015-12-17 | Oryzon Genomics S.A. | Lysine specific demethylase-1 inhibitors and their use |
| PL2560949T3 (pl) | 2010-04-20 | 2017-01-31 | Università Degli Studi Di Roma "La Sapienza" | Pochodne tranylocyprominy jako inhibitory demetylazy histonowej LSD1 i/lub LSD2 |
| CA2791020A1 (en) | 2010-04-28 | 2011-11-03 | Daiichi Sankyo Company, Limited | [5,6] heterocyclic compound |
| JP5702855B2 (ja) | 2010-05-13 | 2015-04-15 | アムジエン・インコーポレーテツド | Ｐｄｅ１０阻害剤として有用な窒素複素環化合物 |
| 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 |
| EP2575808A1 (en) | 2010-05-28 | 2013-04-10 | 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 |
| BR112012033402A2 (pt) | 2010-07-02 | 2017-01-24 | Gilead Sciences Inc | moduladores de canais de íons conforme os compostos heterocíclicos fundidos |
| CN103097384B (zh) | 2010-07-12 | 2017-02-15 | 拜耳知识产权有限责任公司 | 取代的咪唑并[1,2‑a]嘧啶和吡啶 |
| 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 |
| WO2012013727A1 (en) | 2010-07-29 | 2012-02-02 | Oryzon Genomics S.A. | Cyclopropylamine derivatives useful as lsd1 inhibitors |
| CA2806008C (en) | 2010-07-29 | 2019-07-09 | Oryzon Genomics S.A. | Arylcyclopropylamine based demethylase inhibitors of lsd1 and their medical use |
| 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 |
| US9527805B2 (en) | 2010-09-10 | 2016-12-27 | Robert A. Casero | 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 |
| US9643969B2 (en) | 2010-09-29 | 2017-05-09 | Kissei Pharmaceutical Co., Ltd. | (aza)indolizine derivative and pharmaceutical use thereof |
| US20130303545A1 (en) | 2010-09-30 | 2013-11-14 | Tamara Maes | Cyclopropylamine derivatives useful as lsd1 inhibitors |
| US20120108500A1 (en) | 2010-10-07 | 2012-05-03 | Naoki Sakane | 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 |
| EP2444084A1 (en) | 2010-10-21 | 2012-04-25 | Centro Nacional de Investigaciones Oncológicas (CNIO) | Use of PI3K inibitors for the treatment of obesity |
| NZ609490A (en) | 2010-10-21 | 2015-06-26 | Biomarin Pharm Inc | Crystalline (8s,9r)-5-fluoro-8-(4-fluorophenyl)-9-(1-methyl-1h-1,2,4-triazol-5-yl)-8,9-dihydro-2h-pyrido[4,3,2-de]phthalazin-3(7h)-one tosylate salt |
| WO2012052745A1 (en) | 2010-10-21 | 2012-04-26 | Centro Nacional De Investigaciones Oncológicas (Cnio) | Combinations of pi3k inhibitors with a second anti -tumor agent |
| 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 |
| JP2014503528A (ja) | 2010-12-14 | 2014-02-13 | エレクトロプホレトイクス リミテッド | カゼインキナーゼ１δ（ＣＫ１δ）阻害剤及びタウオパチーなどの神経変性疾患の治療におけるその使用 |
| EP2651945A1 (en) | 2010-12-17 | 2013-10-23 | Bayer Intellectual Property GmbH | 6-substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| 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?. |
| WO2012080232A1 (en) | 2010-12-17 | 2012-06-21 | Bayer Pharma Aktiengesellschaft | 2-substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| WO2012080230A1 (en) | 2010-12-17 | 2012-06-21 | Bayer Pharma Aktiengesellschaft | 6 substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| CN103443100B (zh) | 2010-12-17 | 2016-03-23 | 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抑制剂的取代的6-咪唑并吡嗪 |
| 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 |
| WO2012088438A1 (en) | 2010-12-22 | 2012-06-28 | Eutropics Pharmaceuticals, Inc. | Compositions and methods useful for treating diseases |
| US20140038953A1 (en) | 2011-01-21 | 2014-02-06 | The General Hospital Corporation | Compositions and methods for cardiovascular disease |
| EP3981395A1 (en) | 2011-02-08 | 2022-04-13 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for myeloproliferative disorders |
| WO2012107499A1 (en) | 2011-02-08 | 2012-08-16 | Oryzon Genomics S.A. | Lysine demethylase inhibitors for myeloproliferative or lymphoproliferative diseases or disorders |
| EP2678016B1 (en) | 2011-02-23 | 2016-08-10 | 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 |
| KR101884493B1 (ko) | 2011-03-25 | 2018-08-01 | 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 | Lsd1 억제제로서의 시클로프로필아민 |
| 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 |
| US20140296255A1 (en) | 2011-05-19 | 2014-10-02 | Oryzong Genomics, S.A. | Lysine demethylase inhibitors for thrombosis and cardiovascular diseases |
| WO2012156531A2 (en) | 2011-05-19 | 2012-11-22 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for inflammatory diseases or conditions |
| EP2524918A1 (en) | 2011-05-19 | 2012-11-21 | Centro Nacional de Investigaciones Oncológicas (CNIO) | Imidazopyrazines derivates as kinase inhibitors |
| CA2838311A1 (en) | 2011-06-07 | 2012-12-13 | SPAI Group Ltd. | Compositions and methods for improving stability and extending shelf life of sensitive food additives and food products thereof |
| AR086983A1 (es) | 2011-06-20 | 2014-02-05 | Incyte Corp | Derivados de azetidinil fenil, piridil o pirazinil carboxamida como inhibidores de jak |
| 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 |
| MX2014001568A (es) * | 2011-08-09 | 2014-03-31 | Takeda Pharmaceutical | Compuesto de ciclopropanoamina. |
| DK2744330T3 (da) | 2011-08-15 | 2020-09-07 | Univ Utah Res Found | Erstattede (e)-n'-(1-phenylethyliden) benzohydrazid-analoger som histone-demethylase-hæmmere |
| US9289415B2 (en) | 2011-09-01 | 2016-03-22 | 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 |
| MA37958B1 (fr) | 2011-10-10 | 2018-10-31 | H Lundbeck As | Pde9i ayant un squelette imidazo pyrazinone |
| EP2768805B1 (en) | 2011-10-20 | 2020-03-25 | Oryzon Genomics, S.A. | (hetero)aryl cyclopropylamine compounds as lsd1 inhibitors |
| KR102079406B1 (ko) * | 2011-10-20 | 2020-02-19 | 오리존 지노믹스 에스.에이. | Lsd1 억제제로서의 (헤테로)아릴 사이클로프로필아민 화합물 |
| 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. |
| ITMI20111971A1 (it) | 2011-10-28 | 2013-04-29 | Mesogenics Srl | Inibitori dell'enzima lsd-1 per l'induzione del differenziamento osteogenico |
| EP2785183B1 (en) | 2011-11-14 | 2018-12-19 | Merck Sharp & Dohme Corp. | Triazolopyridinone pde10 inhibitors |
| WO2013085877A1 (en) | 2011-12-05 | 2013-06-13 | Brandeis University | Treatment of amyloidosis by compounds that regulate retromer stabilization |
| CA2866450C (en) | 2012-03-07 | 2020-02-18 | 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 |
| US9815819B2 (en) | 2012-06-28 | 2017-11-14 | 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 |
| AU2013324396B2 (en) | 2012-09-28 | 2018-10-04 | Vanderbilt University | Fused heterocyclic compounds as selective BMP inhibitors |
| SG11201502527UA (en) | 2012-10-05 | 2015-04-29 | Rigel Pharmaceuticals Inc | Gdf-8 inhibitors |
| EP2907802B1 (en) * | 2012-10-12 | 2019-08-07 | Takeda Pharmaceutical Company Limited | Cyclopropanamine compound and use thereof |
| WO2014078479A2 (en) | 2012-11-14 | 2014-05-22 | The Board Of Regents Of The University Of Texas System | INHIBITION OF HIF-2α HETERODIMERIZATION WITH HIF1β (ARNT) |
| JP6238908B2 (ja) | 2012-11-28 | 2017-11-29 | 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 |
| AU2013365945B2 (en) | 2012-12-19 | 2017-03-02 | 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 |
| CA2901577A1 (en) | 2013-02-18 | 2014-08-21 | The Scripps Research Institute | Modulators of vasopressin receptors with therapeutic potential |
| 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 |
| AU2014231768A1 (en) | 2013-03-13 | 2015-09-24 | Australian Nuclear Science And Technology Organisation | 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 |
| EP2968343A4 (en) | 2013-03-14 | 2016-11-02 | Epizyme Inc | COMBINATION THERAPY FOR THE TREATMENT OF CANCER |
| WO2014194280A2 (en) | 2013-05-30 | 2014-12-04 | The Board of Regents of the Nevada System of Higher Education on behalf of the University of | Novel suicidal lsd1 inhibitors targeting sox2-expressing cancer cells |
| SG10201710543PA (en) | 2013-06-19 | 2018-02-27 | Univ Utah Res Found | Substituted (e)-n'-(1-phenylethylidene) benzohydrazide analogs as histone demethylase inhibitors |
| 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 |
| WO2015036512A1 (en) | 2013-09-13 | 2015-03-19 | Bayer Pharma Aktiengesellschaft | Pharmaceutical compositions containing 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 |
| US9493442B2 (en) | 2014-02-13 | 2016-11-15 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| JP6602779B2 (ja) | 2014-02-13 | 2019-11-06 | インサイト・コーポレイション | Ｌｓｄ１阻害剤としてのシクロプロピルアミン類 |
| US9527835B2 (en) | 2014-02-13 | 2016-12-27 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| US9428470B2 (en) | 2014-02-13 | 2016-08-30 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| CN106164066B (zh) | 2014-02-13 | 2020-01-17 | 因赛特公司 | 作为lsd1抑制剂的环丙胺 |
| US9346776B2 (en) | 2014-02-13 | 2016-05-24 | Takeda Pharmaceutical Company Limited | Fused 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 |
| HRP20181899T1 (hr) | 2014-04-02 | 2019-01-11 | Bristol-Myers Squibb Company | Biaril inhibitori kinaze |
| WO2015155281A1 (en) | 2014-04-11 | 2015-10-15 | Sanovel Ilac Sanayi Ve Ticaret A.S. | Pharmaceutical combinations of dabigatran and proton pump inhibitors |
| WO2015155297A1 (en) | 2014-04-11 | 2015-10-15 | Sanovel Ilac Sanayi Ve Ticaret A.S. | Pharmaceutical combinations of dabigatran and h2-receptor antagonists |
| UY36071A (es) | 2014-04-11 | 2015-11-30 | Takeda Pharmaceutical | Compuesto de ciclopropanamina y sus usos |
| 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 |
| BR112016028219B1 (pt) | 2014-05-30 | 2022-12-06 | Istituto Europeo Di Oncologia S.R.L | Composto ou composição farmacêutica para uso no tratamento ou prevenção do câncer, de uma doença infecciosa, ou de uma doença designada por aberração de metabolismo de energia celular em um indivíduo, processo para obtenção de um composto de fórmula (i) e uso do composto ou composição farmacêutica na fabricação de um medicamento para uso no tratamento ou prevenção do câncer, de uma doença infecciosa, ou de uma doença designada por aberração de metabolismo de energia celular em um indivíduo |
| 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 |
| WO2016007727A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| US9695168B2 (en) | 2014-07-10 | 2017-07-04 | Incyte Corporation | Substituted imidazo[1,5-α]pyridines and imidazo[1,5-α]pyrazines as LSD1 inhibitors |
| WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| TW201613925A (en) | 2014-07-10 | 2016-04-16 | Incyte Corp | Imidazopyrazines as LSD1 inhibitors |
| 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 |
| KR102550852B1 (ko) | 2014-10-08 | 2023-07-05 | 에프. 호프만-라 로슈 아게 | 알도스테론 신타아제 억제제로서의 스피로다이아민 유도체 |
| MX2017012729A (es) | 2015-04-03 | 2017-11-15 | Bristol Myers Squibb Co | Inhibidores de indolamina 2,3-dioxigenasa (ido) para el tratamiento de cancer. |
| WO2016156597A1 (en) | 2015-04-03 | 2016-10-06 | Mutabilis | Heterocyclic compounds and their use in preventing or treating bacterial infections |
| CN107660205B (zh) | 2015-04-03 | 2021-08-27 | 因赛特公司 | 作为lsd1抑制剂的杂环化合物 |
| EA035534B1 (ru) | 2015-08-12 | 2020-06-30 | Инсайт Корпорейшн | Соли ингибитора lsd1 |
| 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 |
| SG11201805645QA (en) | 2015-12-29 | 2018-07-30 | 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 |
| BR112018071585B1 (pt) | 2016-04-22 | 2024-01-02 | Incyte Corporation | Formulações de um inibidor de lsd1, seus usos e método de preparação das mesmas |
| US20200054643A1 (en) | 2017-01-18 | 2020-02-20 | Vanderbilt University | Fused heterocyclic compounds as selective bmp inhibitors |
| KR20190129851A (ko) | 2017-03-16 | 2019-11-20 | 지앙수 헨그루이 메디슨 컴퍼니 리미티드 | 헤테로아릴[4,3-c]피리미딘-5-아민 유도체, 이의 제조 방법 및 이의 의학적 용도 |
| AU2019297361B2 (en) | 2018-07-05 | 2024-06-27 | Incyte Corporation | Fused pyrazine derivatives as A2A / A2B inhibitors |
| US10968200B2 (en) | 2018-08-31 | 2021-04-06 | Incyte Corporation | Salts of an LSD1 inhibitor and processes for preparing the same |
-
2015
- 2015-02-12 JP JP2016551815A patent/JP6602779B2/ja active Active
- 2015-02-12 BR BR112016018555-2A patent/BR112016018555B1/pt active IP Right Grant
- 2015-02-12 SG SG10201806846RA patent/SG10201806846RA/en unknown
- 2015-02-12 SI SI201530894T patent/SI3105226T1/sl unknown
- 2015-02-12 PL PL15707007T patent/PL3105226T3/pl unknown
- 2015-02-12 MY MYPI2016001463A patent/MY196877A/en unknown
- 2015-02-12 SM SM20190620T patent/SMT201900620T1/it unknown
- 2015-02-12 HU HUE15707007A patent/HUE045725T2/hu unknown
- 2015-02-12 AU AU2015217119A patent/AU2015217119C1/en active Active
- 2015-02-12 WO PCT/US2015/015635 patent/WO2015123424A1/en not_active Ceased
- 2015-02-12 CR CR20160395A patent/CR20160395A/es unknown
- 2015-02-12 DK DK15707007.9T patent/DK3105226T3/da active
- 2015-02-12 EA EA201691594A patent/EA201691594A1/ru unknown
- 2015-02-12 NZ NZ723203A patent/NZ723203A/en unknown
- 2015-02-12 RS RS20191440A patent/RS59534B1/sr unknown
- 2015-02-12 EP EP15707007.9A patent/EP3105226B1/en active Active
- 2015-02-12 ME MEP-2019-315A patent/ME03580B/me unknown
- 2015-02-12 CN CN201580019205.7A patent/CN106488915B/zh active Active
- 2015-02-12 CA CA2939081A patent/CA2939081C/en active Active
- 2015-02-12 TW TW104104830A patent/TWI664164B/zh active
- 2015-02-12 ES ES15707007T patent/ES2750956T3/es active Active
- 2015-02-12 UA UAA201609399A patent/UA122389C2/uk unknown
- 2015-02-12 LT LT15707007T patent/LT3105226T/lt unknown
- 2015-02-12 US US14/620,884 patent/US9493450B2/en active Active
- 2015-02-12 CR CR20200362A patent/CR20200362A/es unknown
- 2015-02-12 EP EP19190056.2A patent/EP3626714A1/en not_active Withdrawn
- 2015-02-12 SG SG11201606333VA patent/SG11201606333VA/en unknown
- 2015-02-12 HR HRP20192033TT patent/HRP20192033T1/hr unknown
- 2015-02-12 TW TW108112023A patent/TWI720451B/zh active
- 2015-02-12 MX MX2016010390A patent/MX373103B/es active IP Right Grant
- 2015-02-12 PT PT157070079T patent/PT3105226T/pt unknown
- 2015-02-12 KR KR1020167025066A patent/KR102352408B1/ko active Active
- 2015-02-12 PE PE2016001467A patent/PE20161384A1/es unknown
-
2016
- 2016-07-26 IL IL246950A patent/IL246950B/en active IP Right Grant
- 2016-08-04 PH PH12016501546A patent/PH12016501546A1/en unknown
- 2016-08-10 MX MX2020003702A patent/MX2020003702A/es unknown
- 2016-08-10 CL CL2016002021A patent/CL2016002021A1/es unknown
- 2016-08-17 ZA ZA2016/05715A patent/ZA201605715B/en unknown
- 2016-09-09 EC ECIEPI201673171A patent/ECSP16073171A/es unknown
- 2016-10-07 US US15/288,605 patent/US9994546B2/en active Active
-
2018
- 2018-05-04 US US15/970,954 patent/US10676457B2/en active Active
-
2019
- 2019-06-17 AU AU2019204244A patent/AU2019204244B2/en active Active
- 2019-10-09 JP JP2019186168A patent/JP6781815B2/ja active Active
- 2019-11-21 CY CY20191101225T patent/CY1122314T1/el unknown
-
2020
- 2020-05-01 US US16/864,304 patent/US11155532B2/en not_active Expired - Fee Related
- 2020-09-13 IL IL277299A patent/IL277299B/en unknown
- 2020-10-16 JP JP2020174661A patent/JP2021011496A/ja active Pending