JP2010513319A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010513319A5 JP2010513319A5 JP2009541644A JP2009541644A JP2010513319A5 JP 2010513319 A5 JP2010513319 A5 JP 2010513319A5 JP 2009541644 A JP2009541644 A JP 2009541644A JP 2009541644 A JP2009541644 A JP 2009541644A JP 2010513319 A5 JP2010513319 A5 JP 2010513319A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- heterocycle
- indazol
- piperidin
- ylamino
- 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
- 125000000623 heterocyclic group Chemical group 0.000 claims 105
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 claims 90
- 125000000217 alkyl group Chemical group 0.000 claims 67
- 125000003342 alkenyl group Chemical group 0.000 claims 61
- 125000000304 alkynyl group Chemical group 0.000 claims 61
- 150000001875 compounds Chemical class 0.000 claims 51
- 238000000034 method Methods 0.000 claims 38
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims 36
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims 35
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 34
- 125000001072 heteroaryl group Chemical group 0.000 claims 33
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims 32
- 125000003710 aryl alkyl group Chemical group 0.000 claims 27
- 125000001424 substituent group Chemical group 0.000 claims 27
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 26
- 125000005015 aryl alkynyl group Chemical group 0.000 claims 26
- 125000003118 aryl group Chemical group 0.000 claims 26
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims 26
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 26
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims 26
- 229910052736 halogen Inorganic materials 0.000 claims 19
- 150000002367 halogens Chemical class 0.000 claims 19
- 125000005842 heteroatom Chemical group 0.000 claims 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 230000002401 inhibitory effect Effects 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 7
- 125000002950 monocyclic group Chemical group 0.000 claims 7
- 125000004043 oxo group Chemical group O=* 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000004434 sulfur atom Chemical group 0.000 claims 6
- -1 3-(((R) -3- (lH-indazol-5-ylamino) piperidin-1-yl) methyl) phenoxy Chemical group 0.000 claims 5
- 201000001320 Atherosclerosis Diseases 0.000 claims 4
- 208000002177 Cataract Diseases 0.000 claims 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 4
- 206010047163 Vasospasm Diseases 0.000 claims 4
- 125000002015 acyclic group Chemical group 0.000 claims 4
- 230000036523 atherogenesis Effects 0.000 claims 4
- 239000002775 capsule Substances 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 238000000605 extraction Methods 0.000 claims 4
- 239000012530 fluid Substances 0.000 claims 4
- 238000002513 implantation Methods 0.000 claims 4
- 230000004410 intraocular pressure Effects 0.000 claims 4
- 230000004112 neuroprotection Effects 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 230000010412 perfusion Effects 0.000 claims 4
- 238000002271 resection Methods 0.000 claims 4
- 230000009441 vascular protection Effects 0.000 claims 4
- 230000029663 wound healing Effects 0.000 claims 4
- 230000015572 biosynthetic process Effects 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- HRCKLYFDWWYCLS-LJQANCHMSA-N 2-[3-[[(3r)-3-(isoquinolin-5-ylamino)pyrrolidin-1-yl]methyl]phenoxy]ethanol Chemical compound OCCOC1=CC=CC(CN2C[C@@H](CC2)NC=2C3=CC=NC=C3C=CC=2)=C1 HRCKLYFDWWYCLS-LJQANCHMSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- IHCQSKFOQWOBBA-OXQOHEQNSA-N (2r)-1-[3-[[(3r)-3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenoxy]propan-2-ol Chemical compound C[C@@H](O)COC1=CC=CC(CN2C[C@@H](CCC2)NC=2C=C3C=NNC3=CC=2)=C1 IHCQSKFOQWOBBA-OXQOHEQNSA-N 0.000 claims 1
- IHCQSKFOQWOBBA-UZLBHIALSA-N (2r)-1-[3-[[(3s)-3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenoxy]propan-2-ol Chemical compound C[C@@H](O)COC1=CC=CC(CN2C[C@H](CCC2)NC=2C=C3C=NNC3=CC=2)=C1 IHCQSKFOQWOBBA-UZLBHIALSA-N 0.000 claims 1
- OXZZTYUKEITHSD-VQTJNVASSA-N (2r)-3-[3-[[(3s)-3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenoxy]propane-1,2-diol Chemical compound OC[C@@H](O)COC1=CC=CC(CN2C[C@H](CCC2)NC=2C=C3C=NNC3=CC=2)=C1 OXZZTYUKEITHSD-VQTJNVASSA-N 0.000 claims 1
- OXZZTYUKEITHSD-UXHICEINSA-N (2s)-3-[3-[[(3r)-3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenoxy]propane-1,2-diol Chemical compound OC[C@H](O)COC1=CC=CC(CN2C[C@@H](CCC2)NC=2C=C3C=NNC3=CC=2)=C1 OXZZTYUKEITHSD-UXHICEINSA-N 0.000 claims 1
- RZQREJCXFJBPJW-HSZRJFAPSA-N 2-[3-[[(3r)-3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenoxy]-1-(4-methylpiperazin-1-yl)ethanone Chemical compound C1CN(C)CCN1C(=O)COC1=CC=CC(CN2C[C@@H](CCC2)NC=2C=C3C=NNC3=CC=2)=C1 RZQREJCXFJBPJW-HSZRJFAPSA-N 0.000 claims 1
- XWCDUEYGMIPYND-JOCHJYFZSA-N 2-[3-[[(3r)-3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenoxy]-1-morpholin-4-ylethanone Chemical compound C=1C=CC(CN2C[C@@H](CCC2)NC=2C=C3C=NNC3=CC=2)=CC=1OCC(=O)N1CCOCC1 XWCDUEYGMIPYND-JOCHJYFZSA-N 0.000 claims 1
- BPRCQSXHYHFFRW-GOSISDBHSA-N 2-[3-[[(3r)-3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC(CN2C[C@@H](CCC2)NC=2C=C3C=NNC3=CC=2)=C1 BPRCQSXHYHFFRW-GOSISDBHSA-N 0.000 claims 1
- PDNRANQFZBPQEF-LJQANCHMSA-N 2-[3-[[(3r)-3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenoxy]ethanol Chemical compound OCCOC1=CC=CC(CN2C[C@@H](CCC2)NC=2C=C3C=NNC3=CC=2)=C1 PDNRANQFZBPQEF-LJQANCHMSA-N 0.000 claims 1
- QPEIXLYASHZHRM-GOSISDBHSA-N 2-[3-[[(3r)-3-(1h-indazol-5-ylamino)pyrrolidin-1-yl]methyl]phenoxy]ethanol Chemical compound OCCOC1=CC=CC(CN2C[C@@H](CC2)NC=2C=C3C=NNC3=CC=2)=C1 QPEIXLYASHZHRM-GOSISDBHSA-N 0.000 claims 1
- VDEVCBVUHZCKCU-HXUWFJFHSA-N 2-[3-[[(3r)-3-(isoquinolin-5-ylamino)piperidin-1-yl]methyl]phenoxy]ethanol Chemical compound OCCOC1=CC=CC(CN2C[C@@H](CCC2)NC=2C3=CC=NC=C3C=CC=2)=C1 VDEVCBVUHZCKCU-HXUWFJFHSA-N 0.000 claims 1
- CVQXJHBUWUKUAE-JOCHJYFZSA-N 2-[3-[[(3r)-3-(isoquinolin-5-ylamino)pyrrolidin-1-yl]methyl]phenoxy]-1-morpholin-4-ylethanone Chemical compound C=1C=CC(CN2C[C@@H](CC2)NC=2C3=CC=NC=C3C=CC=2)=CC=1OCC(=O)N1CCOCC1 CVQXJHBUWUKUAE-JOCHJYFZSA-N 0.000 claims 1
- UPWDVLSJGHGBFP-GOSISDBHSA-N 2-[3-[[(3r)-3-(isoquinolin-5-ylamino)pyrrolidin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC(CN2C[C@@H](CC2)NC=2C3=CC=NC=C3C=CC=2)=C1 UPWDVLSJGHGBFP-GOSISDBHSA-N 0.000 claims 1
- PDNRANQFZBPQEF-IBGZPJMESA-N 2-[3-[[(3s)-3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenoxy]ethanol Chemical compound OCCOC1=CC=CC(CN2C[C@H](CCC2)NC=2C=C3C=NNC3=CC=2)=C1 PDNRANQFZBPQEF-IBGZPJMESA-N 0.000 claims 1
- QPEIXLYASHZHRM-SFHVURJKSA-N 2-[3-[[(3s)-3-(1h-indazol-5-ylamino)pyrrolidin-1-yl]methyl]phenoxy]ethanol Chemical compound OCCOC1=CC=CC(CN2C[C@H](CC2)NC=2C=C3C=NNC3=CC=2)=C1 QPEIXLYASHZHRM-SFHVURJKSA-N 0.000 claims 1
- VDEVCBVUHZCKCU-FQEVSTJZSA-N 2-[3-[[(3s)-3-(isoquinolin-5-ylamino)piperidin-1-yl]methyl]phenoxy]ethanol Chemical compound OCCOC1=CC=CC(CN2C[C@H](CCC2)NC=2C3=CC=NC=C3C=CC=2)=C1 VDEVCBVUHZCKCU-FQEVSTJZSA-N 0.000 claims 1
- HRCKLYFDWWYCLS-IBGZPJMESA-N 2-[3-[[(3s)-3-(isoquinolin-5-ylamino)pyrrolidin-1-yl]methyl]phenoxy]ethanol Chemical compound OCCOC1=CC=CC(CN2C[C@H](CC2)NC=2C3=CC=NC=C3C=CC=2)=C1 HRCKLYFDWWYCLS-IBGZPJMESA-N 0.000 claims 1
- BPRCQSXHYHFFRW-UHFFFAOYSA-N 2-[3-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC(CN2CC(CCC2)NC=2C=C3C=NNC3=CC=2)=C1 BPRCQSXHYHFFRW-UHFFFAOYSA-N 0.000 claims 1
- PDNRANQFZBPQEF-UHFFFAOYSA-N 2-[3-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenoxy]ethanol Chemical compound OCCOC1=CC=CC(CN2CC(CCC2)NC=2C=C3C=NNC3=CC=2)=C1 PDNRANQFZBPQEF-UHFFFAOYSA-N 0.000 claims 1
- QPEIXLYASHZHRM-UHFFFAOYSA-N 2-[3-[[3-(1h-indazol-5-ylamino)pyrrolidin-1-yl]methyl]phenoxy]ethanol Chemical compound OCCOC1=CC=CC(CN2CC(CC2)NC=2C=C3C=NNC3=CC=2)=C1 QPEIXLYASHZHRM-UHFFFAOYSA-N 0.000 claims 1
- HRCKLYFDWWYCLS-UHFFFAOYSA-N 2-[3-[[3-(isoquinolin-5-ylamino)pyrrolidin-1-yl]methyl]phenoxy]ethanol Chemical compound OCCOC1=CC=CC(CN2CC(CC2)NC=2C3=CC=NC=C3C=CC=2)=C1 HRCKLYFDWWYCLS-UHFFFAOYSA-N 0.000 claims 1
- UDCBPDAHRGAKOJ-UHFFFAOYSA-N 2-[3-[[4-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenoxy]ethanol Chemical compound OCCOC1=CC=CC(CN2CCC(CC2)NC=2C=C3C=NNC3=CC=2)=C1 UDCBPDAHRGAKOJ-UHFFFAOYSA-N 0.000 claims 1
- CIHPIJHUAGKONW-UHFFFAOYSA-N 2-[4-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1CN1CC(NC=2C=C3C=NNC3=CC=2)CCC1 CIHPIJHUAGKONW-UHFFFAOYSA-N 0.000 claims 1
- GCWJCJSCGSLPQM-UHFFFAOYSA-N 2-[5-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]-2-methylphenoxy]ethanol Chemical compound C1=C(OCCO)C(C)=CC=C1CN1CC(NC=2C=C3C=NNC3=CC=2)CCC1 GCWJCJSCGSLPQM-UHFFFAOYSA-N 0.000 claims 1
- QBXDKOPEYCIHQK-UHFFFAOYSA-N 2-[5-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]indol-1-yl]acetic acid Chemical compound C1=C2NN=CC2=CC(NC2CCCN(C2)CC=2C=C3C=CN(C3=CC=2)CC(=O)O)=C1 QBXDKOPEYCIHQK-UHFFFAOYSA-N 0.000 claims 1
- PBBCVKDKPWRTSW-UHFFFAOYSA-N 2-[5-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]indol-1-yl]ethanol Chemical compound C1=C2NN=CC2=CC(NC2CCCN(C2)CC=2C=C3C=CN(C3=CC=2)CCO)=C1 PBBCVKDKPWRTSW-UHFFFAOYSA-N 0.000 claims 1
- XEQSNPVXRPAPMJ-OAQYLSRUSA-N 2-[6-[[(3r)-3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]indol-1-yl]ethanol Chemical compound C1=C2NN=CC2=CC(N[C@@H]2CCCN(C2)CC2=CC=C3C=CN(C3=C2)CCO)=C1 XEQSNPVXRPAPMJ-OAQYLSRUSA-N 0.000 claims 1
- BXCXZISLTZBGJO-UHFFFAOYSA-N 2-[6-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]-2,3-dihydroindol-1-yl]ethanol Chemical compound C1=C2NN=CC2=CC(NC2CCCN(C2)CC2=CC=C3CCN(C3=C2)CCO)=C1 BXCXZISLTZBGJO-UHFFFAOYSA-N 0.000 claims 1
- IGNAVGHLKLQNRU-UHFFFAOYSA-N 2-[6-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]indol-1-yl]acetic acid Chemical compound C1=C2NN=CC2=CC(NC2CCCN(C2)CC2=CC=C3C=CN(C3=C2)CC(=O)O)=C1 IGNAVGHLKLQNRU-UHFFFAOYSA-N 0.000 claims 1
- XEQSNPVXRPAPMJ-UHFFFAOYSA-N 2-[6-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]indol-1-yl]ethanol Chemical compound C1=C2NN=CC2=CC(NC2CCCN(C2)CC2=CC=C3C=CN(C3=C2)CCO)=C1 XEQSNPVXRPAPMJ-UHFFFAOYSA-N 0.000 claims 1
- HFFGJIJZKRLHOZ-UHFFFAOYSA-N 2-ethynyl-5-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenol Chemical compound C1=C(C#C)C(O)=CC(CN2CC(CCC2)NC=2C=C3C=NNC3=CC=2)=C1 HFFGJIJZKRLHOZ-UHFFFAOYSA-N 0.000 claims 1
- LWKUYNWGILHOCX-UHFFFAOYSA-N 3-[3-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenoxy]propan-1-ol Chemical compound OCCCOC1=CC=CC(CN2CC(CCC2)NC=2C=C3C=NNC3=CC=2)=C1 LWKUYNWGILHOCX-UHFFFAOYSA-N 0.000 claims 1
- IUBQYUTWCSGHJN-UHFFFAOYSA-N 3-[4-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenyl]prop-2-yn-1-ol Chemical compound C1=CC(C#CCO)=CC=C1CN1CC(NC=2C=C3C=NNC3=CC=2)CCC1 IUBQYUTWCSGHJN-UHFFFAOYSA-N 0.000 claims 1
- GDLBRGNBENEOGY-UHFFFAOYSA-N 3-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]benzonitrile Chemical compound N#CC1=CC=CC(CN2CC(CCC2)NC=2C=C3C=NNC3=CC=2)=C1 GDLBRGNBENEOGY-UHFFFAOYSA-N 0.000 claims 1
- KKQFDOMDTGXQMM-UHFFFAOYSA-N 3-[[3-(1h-indazol-5-ylamino)pyrrolidin-1-yl]methyl]benzonitrile Chemical compound N#CC1=CC=CC(CN2CC(CC2)NC=2C=C3C=NNC3=CC=2)=C1 KKQFDOMDTGXQMM-UHFFFAOYSA-N 0.000 claims 1
- HGIRVGIKIQKKOC-UHFFFAOYSA-N 3-[[3-(isoquinolin-5-ylamino)piperidin-1-yl]methyl]benzonitrile Chemical compound N#CC1=CC=CC(CN2CC(CCC2)NC=2C3=CC=NC=C3C=CC=2)=C1 HGIRVGIKIQKKOC-UHFFFAOYSA-N 0.000 claims 1
- DJUWCELEOPHKCD-UHFFFAOYSA-N 3-[[3-(isoquinolin-5-ylamino)pyrrolidin-1-yl]methyl]benzonitrile Chemical compound N#CC1=CC=CC(CN2CC(CC2)NC=2C3=CC=NC=C3C=CC=2)=C1 DJUWCELEOPHKCD-UHFFFAOYSA-N 0.000 claims 1
- IBZCJNIYGGMRCN-UHFFFAOYSA-N 4-[4-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenyl]but-3-yn-1-ol Chemical compound C1=CC(C#CCCO)=CC=C1CN1CC(NC=2C=C3C=NNC3=CC=2)CCC1 IBZCJNIYGGMRCN-UHFFFAOYSA-N 0.000 claims 1
- LFXXHSZZBJKJJF-UHFFFAOYSA-N 4-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1CN1CC(NC=2C=C3C=NNC3=CC=2)CCC1 LFXXHSZZBJKJJF-UHFFFAOYSA-N 0.000 claims 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- ZOHRKOKZKGNCNH-OAQYLSRUSA-N n-[(3r)-1-[(3-cyclopropylphenyl)methyl]pyrrolidin-3-yl]isoquinolin-5-amine Chemical compound C([C@@H](CC1)NC=2C3=CC=NC=C3C=CC=2)N1CC(C=1)=CC=CC=1C1CC1 ZOHRKOKZKGNCNH-OAQYLSRUSA-N 0.000 claims 1
- LMORZGYOIOJSPZ-OAQYLSRUSA-N n-[(3r)-1-[(4-cyclopropylphenyl)methyl]pyrrolidin-3-yl]isoquinolin-5-amine Chemical compound C([C@@H](CC1)NC=2C3=CC=NC=C3C=CC=2)N1CC(C=C1)=CC=C1C1CC1 LMORZGYOIOJSPZ-OAQYLSRUSA-N 0.000 claims 1
- SPMSXTGVXFPBBK-LJQANCHMSA-N n-[(3r)-1-[(4-cyclopropylsulfanylphenyl)methyl]pyrrolidin-3-yl]isoquinolin-5-amine Chemical compound C([C@@H](CC1)NC=2C3=CC=NC=C3C=CC=2)N1CC(C=C1)=CC=C1SC1CC1 SPMSXTGVXFPBBK-LJQANCHMSA-N 0.000 claims 1
- FQZNIWQVFRJDOJ-HXUWFJFHSA-N n-[(3r)-1-[(4-ethynylphenyl)methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1=CC(C#C)=CC=C1CN1C[C@H](NC=2C=C3C=NNC3=CC=2)CCC1 FQZNIWQVFRJDOJ-HXUWFJFHSA-N 0.000 claims 1
- MIMFSAOPASEOEY-HXUWFJFHSA-N n-[(3r)-1-[(4-ethynylphenyl)methyl]pyrrolidin-3-yl]isoquinolin-5-amine Chemical compound C1=CC(C#C)=CC=C1CN1C[C@H](NC=2C3=CC=NC=C3C=CC=2)CC1 MIMFSAOPASEOEY-HXUWFJFHSA-N 0.000 claims 1
- DPZSYTMLVCLGRU-GOSISDBHSA-N n-[(3r)-1-[(4-methylsulfanylphenyl)methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1=CC(SC)=CC=C1CN1C[C@H](NC=2C=C3C=NNC3=CC=2)CCC1 DPZSYTMLVCLGRU-GOSISDBHSA-N 0.000 claims 1
- IQUZIVDCVRBBFR-GOSISDBHSA-N n-[(3r)-1-[(4-methylsulfanylphenyl)methyl]pyrrolidin-3-yl]isoquinolin-5-amine Chemical compound C1=CC(SC)=CC=C1CN1C[C@H](NC=2C3=CC=NC=C3C=CC=2)CC1 IQUZIVDCVRBBFR-GOSISDBHSA-N 0.000 claims 1
- ZOHRKOKZKGNCNH-NRFANRHFSA-N n-[(3s)-1-[(3-cyclopropylphenyl)methyl]pyrrolidin-3-yl]isoquinolin-5-amine Chemical compound C([C@H](CC1)NC=2C3=CC=NC=C3C=CC=2)N1CC(C=1)=CC=CC=1C1CC1 ZOHRKOKZKGNCNH-NRFANRHFSA-N 0.000 claims 1
- LMORZGYOIOJSPZ-NRFANRHFSA-N n-[(3s)-1-[(4-cyclopropylphenyl)methyl]pyrrolidin-3-yl]isoquinolin-5-amine Chemical compound C([C@H](CC1)NC=2C3=CC=NC=C3C=CC=2)N1CC(C=C1)=CC=C1C1CC1 LMORZGYOIOJSPZ-NRFANRHFSA-N 0.000 claims 1
- SPMSXTGVXFPBBK-IBGZPJMESA-N n-[(3s)-1-[(4-cyclopropylsulfanylphenyl)methyl]pyrrolidin-3-yl]isoquinolin-5-amine Chemical compound C([C@H](CC1)NC=2C3=CC=NC=C3C=CC=2)N1CC(C=C1)=CC=C1SC1CC1 SPMSXTGVXFPBBK-IBGZPJMESA-N 0.000 claims 1
- FQZNIWQVFRJDOJ-FQEVSTJZSA-N n-[(3s)-1-[(4-ethynylphenyl)methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1=CC(C#C)=CC=C1CN1C[C@@H](NC=2C=C3C=NNC3=CC=2)CCC1 FQZNIWQVFRJDOJ-FQEVSTJZSA-N 0.000 claims 1
- DPZSYTMLVCLGRU-SFHVURJKSA-N n-[(3s)-1-[(4-methylsulfanylphenyl)methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1=CC(SC)=CC=C1CN1C[C@@H](NC=2C=C3C=NNC3=CC=2)CCC1 DPZSYTMLVCLGRU-SFHVURJKSA-N 0.000 claims 1
- IQUZIVDCVRBBFR-SFHVURJKSA-N n-[(3s)-1-[(4-methylsulfanylphenyl)methyl]pyrrolidin-3-yl]isoquinolin-5-amine Chemical compound C1=CC(SC)=CC=C1CN1C[C@@H](NC=2C3=CC=NC=C3C=CC=2)CC1 IQUZIVDCVRBBFR-SFHVURJKSA-N 0.000 claims 1
- QQPGUHWCZXHDEH-UHFFFAOYSA-N n-[1-[(3-cyclopropylphenyl)methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1CCC(NC=2C=C3C=NNC3=CC=2)CN1CC(C=1)=CC=CC=1C1CC1 QQPGUHWCZXHDEH-UHFFFAOYSA-N 0.000 claims 1
- CLCMIAAQLBZPHZ-UHFFFAOYSA-N n-[1-[(3-cyclopropylphenyl)methyl]piperidin-3-yl]isoquinolin-5-amine Chemical compound C1CCC(NC=2C3=CC=NC=C3C=CC=2)CN1CC(C=1)=CC=CC=1C1CC1 CLCMIAAQLBZPHZ-UHFFFAOYSA-N 0.000 claims 1
- ISVDVUHFFNAXRM-UHFFFAOYSA-N n-[1-[(3-ethynylphenyl)methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C#CC1=CC=CC(CN2CC(CCC2)NC=2C=C3C=NNC3=CC=2)=C1 ISVDVUHFFNAXRM-UHFFFAOYSA-N 0.000 claims 1
- NGHLZEZXRFLFJC-UHFFFAOYSA-N n-[1-[(3-methylsulfanylphenyl)methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound CSC1=CC=CC(CN2CC(CCC2)NC=2C=C3C=NNC3=CC=2)=C1 NGHLZEZXRFLFJC-UHFFFAOYSA-N 0.000 claims 1
- OLGYHXPKEZCVEP-UHFFFAOYSA-N n-[1-[(3-methylsulfonylphenyl)methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound CS(=O)(=O)C1=CC=CC(CN2CC(CCC2)NC=2C=C3C=NNC3=CC=2)=C1 OLGYHXPKEZCVEP-UHFFFAOYSA-N 0.000 claims 1
- QUJOREAGMCLAOO-UHFFFAOYSA-N n-[1-[(4-cyclopropylphenyl)methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1CCC(NC=2C=C3C=NNC3=CC=2)CN1CC(C=C1)=CC=C1C1CC1 QUJOREAGMCLAOO-UHFFFAOYSA-N 0.000 claims 1
- NWQAWCOYBNUWPT-UHFFFAOYSA-N n-[1-[(4-cyclopropylphenyl)methyl]piperidin-3-yl]isoquinolin-5-amine Chemical compound C1CCC(NC=2C3=CC=NC=C3C=CC=2)CN1CC(C=C1)=CC=C1C1CC1 NWQAWCOYBNUWPT-UHFFFAOYSA-N 0.000 claims 1
- XOGZXGLZHJWWDZ-UHFFFAOYSA-N n-[1-[(4-cyclopropylsulfanylphenyl)methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1CCC(NC=2C=C3C=NNC3=CC=2)CN1CC(C=C1)=CC=C1SC1CC1 XOGZXGLZHJWWDZ-UHFFFAOYSA-N 0.000 claims 1
- XPXJREKHQWNIQZ-UHFFFAOYSA-N n-[1-[(4-cyclopropylsulfanylphenyl)methyl]piperidin-3-yl]isoquinolin-5-amine Chemical compound C1CCC(NC=2C3=CC=NC=C3C=CC=2)CN1CC(C=C1)=CC=C1SC1CC1 XPXJREKHQWNIQZ-UHFFFAOYSA-N 0.000 claims 1
- DQNYJGMBMWJKJV-UHFFFAOYSA-N n-[1-[(4-ethenylphenyl)methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1=CC(C=C)=CC=C1CN1CC(NC=2C=C3C=NNC3=CC=2)CCC1 DQNYJGMBMWJKJV-UHFFFAOYSA-N 0.000 claims 1
- DLTBJFNKVNSDQJ-UHFFFAOYSA-N n-[1-[(4-ethylsulfanylphenyl)methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1=CC(SCC)=CC=C1CN1CC(NC=2C=C3C=NNC3=CC=2)CCC1 DLTBJFNKVNSDQJ-UHFFFAOYSA-N 0.000 claims 1
- FQZNIWQVFRJDOJ-UHFFFAOYSA-N n-[1-[(4-ethynylphenyl)methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1=CC(C#C)=CC=C1CN1CC(NC=2C=C3C=NNC3=CC=2)CCC1 FQZNIWQVFRJDOJ-UHFFFAOYSA-N 0.000 claims 1
- DMQNUCUGOVADJT-UHFFFAOYSA-N n-[1-[(4-methylsulfanylphenyl)methyl]piperidin-3-yl]isoquinolin-5-amine Chemical compound C1=CC(SC)=CC=C1CN1CC(NC=2C3=CC=NC=C3C=CC=2)CCC1 DMQNUCUGOVADJT-UHFFFAOYSA-N 0.000 claims 1
- DLFCOOXTMLTEEG-UHFFFAOYSA-N n-[1-[(4-methylsulfonylphenyl)methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CN1CC(NC=2C=C3C=NNC3=CC=2)CCC1 DLFCOOXTMLTEEG-UHFFFAOYSA-N 0.000 claims 1
- XSYWGPNWBBDYPP-UHFFFAOYSA-N n-[1-[(4-methylsulfonylphenyl)methyl]piperidin-3-yl]isoquinolin-5-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CN1CC(NC=2C3=CC=NC=C3C=CC=2)CCC1 XSYWGPNWBBDYPP-UHFFFAOYSA-N 0.000 claims 1
- XKFGCNGELSXIMD-UHFFFAOYSA-N n-[1-[(4-methylsulfonylphenyl)methyl]pyrrolidin-3-yl]-1h-indazol-5-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CN1CC(NC=2C=C3C=NNC3=CC=2)CC1 XKFGCNGELSXIMD-UHFFFAOYSA-N 0.000 claims 1
- IERPXRYTDDRYGB-UHFFFAOYSA-N n-[1-[(4-methylsulfonylphenyl)methyl]pyrrolidin-3-yl]isoquinolin-5-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CN1CC(NC=2C3=CC=NC=C3C=CC=2)CC1 IERPXRYTDDRYGB-UHFFFAOYSA-N 0.000 claims 1
- BMTAHBGHVDJLDW-UHFFFAOYSA-N n-[1-[(4-morpholin-4-ylphenyl)methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1CCC(NC=2C=C3C=NNC3=CC=2)CN1CC(C=C1)=CC=C1N1CCOCC1 BMTAHBGHVDJLDW-UHFFFAOYSA-N 0.000 claims 1
- XOHJYOXUEUCFEV-UHFFFAOYSA-N n-[1-[(4-phenylphenyl)methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1CCC(NC=2C=C3C=NNC3=CC=2)CN1CC(C=C1)=CC=C1C1=CC=CC=C1 XOHJYOXUEUCFEV-UHFFFAOYSA-N 0.000 claims 1
- SOXNYIWWQIFJRI-UHFFFAOYSA-N n-[1-[(4-pyrrolidin-1-ylphenyl)methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1CCC(NC=2C=C3C=NNC3=CC=2)CN1CC(C=C1)=CC=C1N1CCCC1 SOXNYIWWQIFJRI-UHFFFAOYSA-N 0.000 claims 1
- WAVNRZBIYVZRSB-UHFFFAOYSA-N n-[1-[(4-thiophen-2-ylphenyl)methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1CCC(NC=2C=C3C=NNC3=CC=2)CN1CC(C=C1)=CC=C1C1=CC=CS1 WAVNRZBIYVZRSB-UHFFFAOYSA-N 0.000 claims 1
- QPQXUWYBRBDMKL-UHFFFAOYSA-N n-[1-[[3-(2-aminoethoxy)phenyl]methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound NCCOC1=CC=CC(CN2CC(CCC2)NC=2C=C3C=NNC3=CC=2)=C1 QPQXUWYBRBDMKL-UHFFFAOYSA-N 0.000 claims 1
- LNAVORGTPYZRDM-UHFFFAOYSA-N n-[1-[[3-(aminomethyl)phenyl]methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound NCC1=CC=CC(CN2CC(CCC2)NC=2C=C3C=NNC3=CC=2)=C1 LNAVORGTPYZRDM-UHFFFAOYSA-N 0.000 claims 1
- AIEDMXUFXQBODU-UHFFFAOYSA-N n-[1-[[4-(2-cyclopropylethynyl)phenyl]methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1CCC(NC=2C=C3C=NNC3=CC=2)CN1CC(C=C1)=CC=C1C#CC1CC1 AIEDMXUFXQBODU-UHFFFAOYSA-N 0.000 claims 1
- LFRWJOOFIZGJRS-UHFFFAOYSA-N n-[1-[[4-(aminomethyl)phenyl]methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1=CC(CN)=CC=C1CN1CC(NC=2C=C3C=NNC3=CC=2)CCC1 LFRWJOOFIZGJRS-UHFFFAOYSA-N 0.000 claims 1
- PKCSBJKNGDETTE-UHFFFAOYSA-N n-[1-[[4-(methylsulfanylmethyl)phenyl]methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1=CC(CSC)=CC=C1CN1CC(NC=2C=C3C=NNC3=CC=2)CCC1 PKCSBJKNGDETTE-UHFFFAOYSA-N 0.000 claims 1
- CWXOVADRAJYZRV-UHFFFAOYSA-N n-[1-[[4-(methylsulfonylmethyl)phenyl]methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1=CC(CS(=O)(=O)C)=CC=C1CN1CC(NC=2C=C3C=NNC3=CC=2)CCC1 CWXOVADRAJYZRV-UHFFFAOYSA-N 0.000 claims 1
- YKVGSJWLOZXWNB-UHFFFAOYSA-N n-[1-[[4-[(dimethylamino)methyl]phenyl]methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1=CC(CN(C)C)=CC=C1CN1CC(NC=2C=C3C=NNC3=CC=2)CCC1 YKVGSJWLOZXWNB-UHFFFAOYSA-N 0.000 claims 1
- QRMMOYFBMFFTSZ-UHFFFAOYSA-N n-[1-[[4-[3-(dimethylamino)propoxy]phenyl]methyl]pyrrolidin-3-yl]-1h-indazol-5-amine Chemical compound C1=CC(OCCCN(C)C)=CC=C1CN1CC(NC=2C=C3C=NNC3=CC=2)CC1 QRMMOYFBMFFTSZ-UHFFFAOYSA-N 0.000 claims 1
- HUVLXAMZMWMEAO-UHFFFAOYSA-N n-[2-[3-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenoxy]ethyl]acetamide Chemical compound CC(=O)NCCOC1=CC=CC(CN2CC(CCC2)NC=2C=C3C=NNC3=CC=2)=C1 HUVLXAMZMWMEAO-UHFFFAOYSA-N 0.000 claims 1
- UVIWSVMESNYYMT-UHFFFAOYSA-N n-[2-chloro-5-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=C(Cl)C(NS(=O)(=O)C)=CC(CN2CC(CCC2)NC=2C=C3C=NNC3=CC=2)=C1 UVIWSVMESNYYMT-UHFFFAOYSA-N 0.000 claims 1
- DSSHWWLYALEYJS-HXUWFJFHSA-N n-[3-[[(3r)-3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=CC(CN2C[C@@H](CCC2)NC=2C=C3C=NNC3=CC=2)=C1 DSSHWWLYALEYJS-HXUWFJFHSA-N 0.000 claims 1
- VYDWBAYBPOUUPX-LJQANCHMSA-N n-[3-[[(3r)-3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(CN2C[C@@H](CCC2)NC=2C=C3C=NNC3=CC=2)=C1 VYDWBAYBPOUUPX-LJQANCHMSA-N 0.000 claims 1
- CPVFJCZYQSPUEE-GOSISDBHSA-N n-[3-[[(3r)-3-(1h-indazol-5-ylamino)pyrrolidin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(CN2C[C@@H](CC2)NC=2C=C3C=NNC3=CC=2)=C1 CPVFJCZYQSPUEE-GOSISDBHSA-N 0.000 claims 1
- JVACKTOSODNYNH-HXUWFJFHSA-N n-[3-[[(3r)-3-(isoquinolin-5-ylamino)piperidin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(CN2C[C@@H](CCC2)NC=2C3=CC=NC=C3C=CC=2)=C1 JVACKTOSODNYNH-HXUWFJFHSA-N 0.000 claims 1
- CNFJHJMGGNMYDX-HXUWFJFHSA-N n-[3-[[(3r)-3-(isoquinolin-5-ylamino)pyrrolidin-1-yl]methyl]phenyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=CC(CN2C[C@@H](CC2)NC=2C3=CC=NC=C3C=CC=2)=C1 CNFJHJMGGNMYDX-HXUWFJFHSA-N 0.000 claims 1
- ZRMHZVWQKSOWAN-LJQANCHMSA-N n-[3-[[(3r)-3-(isoquinolin-5-ylamino)pyrrolidin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(CN2C[C@@H](CC2)NC=2C3=CC=NC=C3C=CC=2)=C1 ZRMHZVWQKSOWAN-LJQANCHMSA-N 0.000 claims 1
- DSSHWWLYALEYJS-FQEVSTJZSA-N n-[3-[[(3s)-3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=CC(CN2C[C@H](CCC2)NC=2C=C3C=NNC3=CC=2)=C1 DSSHWWLYALEYJS-FQEVSTJZSA-N 0.000 claims 1
- VYDWBAYBPOUUPX-IBGZPJMESA-N n-[3-[[(3s)-3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(CN2C[C@H](CCC2)NC=2C=C3C=NNC3=CC=2)=C1 VYDWBAYBPOUUPX-IBGZPJMESA-N 0.000 claims 1
- CPVFJCZYQSPUEE-SFHVURJKSA-N n-[3-[[(3s)-3-(1h-indazol-5-ylamino)pyrrolidin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(CN2C[C@H](CC2)NC=2C=C3C=NNC3=CC=2)=C1 CPVFJCZYQSPUEE-SFHVURJKSA-N 0.000 claims 1
- JVACKTOSODNYNH-FQEVSTJZSA-N n-[3-[[(3s)-3-(isoquinolin-5-ylamino)piperidin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(CN2C[C@H](CCC2)NC=2C3=CC=NC=C3C=CC=2)=C1 JVACKTOSODNYNH-FQEVSTJZSA-N 0.000 claims 1
- ZRMHZVWQKSOWAN-IBGZPJMESA-N n-[3-[[(3s)-3-(isoquinolin-5-ylamino)pyrrolidin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(CN2C[C@H](CC2)NC=2C3=CC=NC=C3C=CC=2)=C1 ZRMHZVWQKSOWAN-IBGZPJMESA-N 0.000 claims 1
- ATFSXSWVVPUEBE-UHFFFAOYSA-N n-[3-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenyl]-n-methylmethanesulfonamide Chemical compound CS(=O)(=O)N(C)C1=CC=CC(CN2CC(CCC2)NC=2C=C3C=NNC3=CC=2)=C1 ATFSXSWVVPUEBE-UHFFFAOYSA-N 0.000 claims 1
- DSSHWWLYALEYJS-UHFFFAOYSA-N n-[3-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=CC(CN2CC(CCC2)NC=2C=C3C=NNC3=CC=2)=C1 DSSHWWLYALEYJS-UHFFFAOYSA-N 0.000 claims 1
- VYDWBAYBPOUUPX-UHFFFAOYSA-N n-[3-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(CN2CC(CCC2)NC=2C=C3C=NNC3=CC=2)=C1 VYDWBAYBPOUUPX-UHFFFAOYSA-N 0.000 claims 1
- CPVFJCZYQSPUEE-UHFFFAOYSA-N n-[3-[[3-(1h-indazol-5-ylamino)pyrrolidin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(CN2CC(CC2)NC=2C=C3C=NNC3=CC=2)=C1 CPVFJCZYQSPUEE-UHFFFAOYSA-N 0.000 claims 1
- UNHJXKXHKIFADV-UHFFFAOYSA-N n-[4-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CN1CC(NC=2C=C3C=NNC3=CC=2)CCC1 UNHJXKXHKIFADV-UHFFFAOYSA-N 0.000 claims 1
- RNANERPNWMVVAB-UHFFFAOYSA-N n-[4-[[3-(1h-indazol-5-ylamino)pyrrolidin-1-yl]methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CN1CC(NC=2C=C3C=NNC3=CC=2)CC1 RNANERPNWMVVAB-UHFFFAOYSA-N 0.000 claims 1
- LBXZGQULVZGSNR-UHFFFAOYSA-N n-[4-[[3-(isoquinolin-5-ylamino)piperidin-1-yl]methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CN1CC(NC=2C3=CC=NC=C3C=CC=2)CCC1 LBXZGQULVZGSNR-UHFFFAOYSA-N 0.000 claims 1
- YCCKDGUXWPCDCH-UHFFFAOYSA-N n-[4-[[3-(isoquinolin-5-ylamino)pyrrolidin-1-yl]methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CN1CC(NC=2C3=CC=NC=C3C=CC=2)CC1 YCCKDGUXWPCDCH-UHFFFAOYSA-N 0.000 claims 1
- CDKZHWZCXRRPDX-UHFFFAOYSA-N n-[[3-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenyl]methyl]acetamide Chemical compound CC(=O)NCC1=CC=CC(CN2CC(CCC2)NC=2C=C3C=NNC3=CC=2)=C1 CDKZHWZCXRRPDX-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87055506P | 2006-12-18 | 2006-12-18 | |
| US60/870,555 | 2006-12-18 | ||
| US11/958,214 | 2007-12-17 | ||
| US11/958,214 US8071779B2 (en) | 2006-12-18 | 2007-12-17 | Cytoskeletal active rho kinase inhibitor compounds, composition and use |
| PCT/US2007/087973 WO2008077057A2 (en) | 2006-12-18 | 2007-12-18 | Cytoskeletal active rho kinase inhibitor compounds, composition and use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010513319A JP2010513319A (ja) | 2010-04-30 |
| JP2010513319A5 true JP2010513319A5 (enExample) | 2010-12-24 |
| JP5511385B2 JP5511385B2 (ja) | 2014-06-04 |
Family
ID=39537056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009541644A Expired - Fee Related JP5511385B2 (ja) | 2006-12-18 | 2007-12-18 | 細胞骨格活性ｒｈｏキナーゼインヒビター化合物、組成物及び使用 |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US8071779B2 (enExample) |
| EP (1) | EP2099457A4 (enExample) |
| JP (1) | JP5511385B2 (enExample) |
| KR (1) | KR20090091767A (enExample) |
| CN (2) | CN103254172A (enExample) |
| AU (1) | AU2007333715B2 (enExample) |
| BR (1) | BRPI0720457A2 (enExample) |
| CA (1) | CA2672825A1 (enExample) |
| MX (1) | MX2009006493A (enExample) |
| RU (1) | RU2470928C2 (enExample) |
| WO (1) | WO2008077057A2 (enExample) |
Families Citing this family (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2580108T3 (es) | 2005-07-11 | 2016-08-19 | Aerie Pharmaceuticals, Inc | Compuestos de isoquinolina |
| EP2462959B1 (en) * | 2005-07-12 | 2016-06-22 | Ampio Pharmaceuticals, Inc. | Methods and products for treatment of diseases |
| EP2526948A1 (en) | 2006-09-20 | 2012-11-28 | Aerie Pharmaceuticals, Inc. | RHO kinase inhibitors |
| US20100022517A1 (en) * | 2006-12-18 | 2010-01-28 | Richards Lori A | Ophthalmic formulation of rho kinase inhibitor compound |
| US8455513B2 (en) | 2007-01-10 | 2013-06-04 | Aerie Pharmaceuticals, Inc. | 6-aminoisoquinoline compounds |
| AR070950A1 (es) | 2007-11-01 | 2010-05-19 | Acucela Inc | Compuestos derivados de amina, composiciones farmaceuticas de ellos, compuestos inhibidores de produccion de 11-cis-retinol y metodos para tratar enfermedades y trastornos oftalmicos |
| US8455514B2 (en) | 2008-01-17 | 2013-06-04 | Aerie Pharmaceuticals, Inc. | 6-and 7-amino isoquinoline compounds and methods for making and using the same |
| RU2011101572A (ru) * | 2008-06-18 | 2012-07-27 | Инспайр Фармасьютикалз, Инк. (Us) | Способ получения соединений, ингибирующих ро-киназу |
| US8207195B2 (en) * | 2008-06-26 | 2012-06-26 | Inspire Pharmaceuticals, Inc. | Method for treating neurological and neuropathic diseases using rho kinase inhibitor compounds |
| US8410147B2 (en) * | 2008-06-26 | 2013-04-02 | Inspire Pharmaceuticals, Inc. | Method for treating diseases associated with alterations in cellular integrity using Rho kinase inhibitor compounds |
| US20100008968A1 (en) * | 2008-06-26 | 2010-01-14 | Lampe John W | Method for treating cardiovascular diseases using rho kinase inhibitor compounds |
| US20090325960A1 (en) * | 2008-06-26 | 2009-12-31 | Fulcher Emilee H | Method for treating inflammatory diseases using rho kinase inhibitor compounds |
| US20090325959A1 (en) * | 2008-06-26 | 2009-12-31 | Vittitow Jason L | Method for treating ophthalmic diseases using rho kinase inhibitor compounds |
| WO2009158587A1 (en) * | 2008-06-26 | 2009-12-30 | Inspire Pharmaceuticals, Inc. | Method for treating pulmonary diseases using rho kinase inhibitor compounds |
| US8450344B2 (en) | 2008-07-25 | 2013-05-28 | Aerie Pharmaceuticals, Inc. | Beta- and gamma-amino-isoquinoline amide compounds and substituted benzamide compounds |
| EP2400969A4 (en) * | 2008-12-04 | 2012-05-16 | Inspire Pharmaceuticals Inc | METHOD FOR TREATING PULMONARY DISEASES USING RHO KINASE INHIBITORY COMPOUNDS |
| WO2010126626A2 (en) | 2009-05-01 | 2010-11-04 | Aerie Pharmaceuticals, Inc. | Dual mechanism inhibitors for the treatment of disease |
| SG2014008171A (en) | 2009-06-22 | 2014-04-28 | Ampio Pharmaceuticals Inc | Method for treatment of diseases |
| SG177302A1 (en) * | 2009-06-22 | 2012-02-28 | Dmi Acquisition Corp | Methods and products for treatment of diseases |
| AU2015203100B2 (en) * | 2009-06-22 | 2017-03-16 | Ampio Pharmaceuticals, Inc. | Method for treatment of diseases |
| WO2011075415A1 (en) | 2009-12-14 | 2011-06-23 | Inspire Pharmaceuticals, Inc. | Bridged bicyclic rho kinase inhibitor compounds, composition and use |
| WO2012012282A1 (en) * | 2010-07-19 | 2012-01-26 | Inspire Pharmaceuticals, Inc. | Bifunctional rho kinase inhibitor compounds, composition and use |
| EP2597953A4 (en) * | 2010-07-27 | 2013-12-25 | Inspire Pharmaceuticals Inc | METHOD FOR THE TREATMENT OF EYE DISEASES USING KINASE-INHIBITOR COMPOUNDS IN PRODRUG FORMS |
| GB201107223D0 (en) * | 2011-04-29 | 2011-06-15 | Amakem Nv | Novel rock inhibitors |
| TR201903889T4 (tr) * | 2011-12-06 | 2019-04-22 | Astellas Inst For Regenerative Medicine | Korneal endotelyal hücreler üreten yönlendirilmiş diferansiyasyona yönelik yöntem. |
| EP2794565B1 (en) | 2011-12-21 | 2017-07-26 | Novira Therapeutics Inc. | Hepatitis b antiviral agents |
| US20130168825A1 (en) * | 2011-12-30 | 2013-07-04 | Alliance For Sustainable Energy, Llc | Fabrication of ionic liquid electrodeposited cu-sn-zn-s-se thin films and method of making |
| CA2881057C (en) | 2012-08-28 | 2020-10-27 | Janssen Sciences Ireland Uc | Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis b |
| BR112015009504A2 (pt) * | 2012-10-31 | 2017-07-04 | Amakem Nv | inibidores de rock |
| SG11201504380SA (en) | 2012-12-19 | 2015-07-30 | Ampio Pharmaceuticals Inc | Method for treatment of diseases |
| JP6466348B2 (ja) | 2013-02-28 | 2019-02-06 | ヤンセン・サイエンシズ・アイルランド・アンリミテッド・カンパニー | スルファモイル−アリールアミドおよびｂ型肝炎を処置するための医薬品としてのその使用 |
| ES2776199T3 (es) | 2013-03-15 | 2020-07-29 | Aerie Pharmaceuticals Inc | Conjugados de compuestos de isoquinolina y prostaglandinas |
| HUE033542T2 (en) | 2013-04-03 | 2017-12-28 | Janssen Sciences Ireland Uc | Their use as medicaments for the treatment of N-phenylcarboxamide derivatives and hepatitis B |
| TW202126620A (zh) | 2013-05-17 | 2021-07-16 | 愛爾蘭商健生科學愛爾蘭無限公司 | 胺磺醯基吡咯醯胺衍生物及其作為用於治療ｂ型肝炎藥物的用途 |
| HUE040446T2 (hu) | 2013-05-17 | 2019-03-28 | Janssen Sciences Ireland Uc | Szulfamoiltiofenamid-származékok és gyógyszerként történõ alkalmazásuk hepatitis B kezelésére |
| WO2015011281A1 (en) | 2013-07-25 | 2015-01-29 | Janssen R&D Ireland | Glyoxamide substituted pyrrolamide derivatives and the use thereof as medicaments for the treatment of hepatitis b |
| MX368158B (es) | 2013-10-23 | 2019-09-20 | Janssen Sciences Ireland Uc | Derivados de carboxamida y su uso como medicamentos para el tratamiento de la hepatitis b. |
| US9169212B2 (en) | 2014-01-16 | 2015-10-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
| US10392349B2 (en) | 2014-01-16 | 2019-08-27 | Novira Therapeutics, Inc. | Azepane derivatives and methods of treating hepatitis B infections |
| JP6553059B2 (ja) | 2014-02-05 | 2019-07-31 | ノヴィラ・セラピューティクス・インコーポレイテッド | Ｈｂｖ感染の治療のための併用療法 |
| PL3102572T3 (pl) | 2014-02-06 | 2019-04-30 | Janssen Sciences Ireland Uc | Pochodne sulfamoilopirolamidu i ich zastosowanie jako leki do leczenia wirusowego zapalenia wątroby typu B |
| US10335449B2 (en) | 2014-10-06 | 2019-07-02 | University Of Houston System | Rho associated kinase (ROCK) inhibitors and their use in treating disease |
| EP3271019A1 (en) | 2015-03-19 | 2018-01-24 | Novira Therapeutics Inc. | Azocane and azonane derivatives and methods of treating hepatitis b infections |
| EP3294871B1 (en) | 2015-05-12 | 2026-04-29 | HemostOD SA | Combination of pharmacological and microfluidic features for improved platelets production |
| US10875876B2 (en) | 2015-07-02 | 2020-12-29 | Janssen Sciences Ireland Uc | Cyclized sulfamoylarylamide derivatives and the use thereof as medicaments for the treatment of hepatitis B |
| AR106192A1 (es) | 2015-09-29 | 2017-12-20 | Novira Therapeutics Inc | Formas cristalinas de un agente antiviral contra la hepatitis b |
| WO2017086941A1 (en) | 2015-11-17 | 2017-05-26 | Aerie Pharmaceuticals, Inc. | Process for the preparation of kinase inhibitors and intermediates thereof |
| US9643927B1 (en) | 2015-11-17 | 2017-05-09 | Aerie Pharmaceuticals, Inc. | Process for the preparation of kinase inhibitors and intermediates thereof |
| WO2017181141A2 (en) | 2016-04-15 | 2017-10-19 | Novira Therapeutics, Inc. | Combinations and methods comprising a capsid assembly inhibitor |
| WO2018045091A1 (en) | 2016-08-31 | 2018-03-08 | Aerie Pharmaceuticals, Inc. | Ophthalmic compositions |
| AU2018223192A1 (en) * | 2017-02-27 | 2019-06-20 | Janssen Pharmaceutica Nv | [1,2,4]-triazolo [1,5-a]-pyrimidinyl derivatives substituted with piperidine, morpholine or piperazine as OGA inhibitors |
| CA3057872A1 (en) | 2017-03-31 | 2018-10-04 | Aerie Pharmaceuticals, Inc. | Aryl cyclopropyl-amino-isoquinolinyl amide compounds |
| BR112020008850A2 (pt) | 2017-11-03 | 2020-10-20 | Aclaris Therapeutics, Inc. | composto, composição farmacêutica e método para tratar uma doença mediada por jak1 e jak3 |
| SG11202007097QA (en) | 2018-03-14 | 2020-08-28 | Janssen Sciences Ireland Unlimited Co | Capsid assembly modulator dosing regimen |
| CN108929258A (zh) * | 2018-07-09 | 2018-12-04 | 张立国 | 一种Rho激酶抑制剂及其在癌症治疗中的应用 |
| CN108569990A (zh) * | 2018-07-09 | 2018-09-25 | 张立国 | 多取代吡咯烷衍生物及其作为Rho激酶抑制剂在癌症中的应用 |
| JP7591500B2 (ja) | 2018-08-10 | 2024-11-28 | アクラリス セラピューティクス，インコーポレイテッド | ピロロピリミジンｉｔｋ阻害剤 |
| CA3110661A1 (en) | 2018-08-29 | 2020-03-05 | University Of Massachusetts | Inhibition of protein kinases to treat friedreich ataxia |
| AU2019337703B2 (en) | 2018-09-14 | 2023-02-02 | Aerie Pharmaceuticals, Inc. | Aryl cyclopropyl-amino-isoquinolinyl amide compounds |
| WO2020072456A1 (en) * | 2018-10-02 | 2020-04-09 | Case Western Reserve University | Compounds for treating myelin related disorders |
| AU2020223865A1 (en) | 2019-02-22 | 2021-07-15 | Janssen Sciences Ireland Unlimited Company | Amide derivatives useful in the treatment of HBV infection or HBV-induced diseases |
| BR112021021454A2 (pt) | 2019-05-06 | 2021-12-21 | Janssen Sciences Ireland Unlimited Co | Derivados de amida úteis no tratamento da infecção por hbv ou doenças induzidas por hbv |
| CN110215519A (zh) * | 2019-07-12 | 2019-09-10 | 温州医科大学附属眼视光医院 | 药物修饰型人工晶状体及其制备方法和应用 |
| CN114133394B (zh) * | 2020-08-12 | 2023-12-08 | 赛诺哈勃药业（成都）有限公司 | 一种选择性针对细胞周期依赖性激酶12活性的化合物、制备方法及医药用途 |
| MX2024002173A (es) | 2021-08-18 | 2024-03-26 | Chemocentryx Inc | Compuestos de arilsulfonilo como inhibidores de ccr6. |
| IL310368A (en) | 2021-08-18 | 2024-03-01 | Chemocentryx Inc | Arylsulfonyl(hydroxy)piperidines as CCR6 inhibitors |
| TW202329937A (zh) | 2021-12-03 | 2023-08-01 | 美商英塞特公司 | 雙環胺ｃｋ１２抑制劑 |
| US12084453B2 (en) | 2021-12-10 | 2024-09-10 | Incyte Corporation | Bicyclic amines as CDK12 inhibitors |
| CN116891460A (zh) * | 2023-07-12 | 2023-10-17 | 浙江大学 | 一种吲唑类衍生物或其药用盐及应用 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4524816A (en) * | 1984-02-21 | 1985-06-25 | Dentsply Research & Development Corp. | Centrifugal casting furnace |
| US6339099B1 (en) * | 1997-06-20 | 2002-01-15 | Dupont Pharmaceuticals Company | Guanidine mimics as factor Xa inhibitors |
| YU54202A (sh) * | 2000-01-18 | 2006-01-16 | Agouron Pharmaceuticals Inc. | Jedinjenja indazola, farmaceutske smeše i postupci za stimulisanje i inhibiranje ćelijske proliferacije |
| US7217722B2 (en) * | 2000-02-01 | 2007-05-15 | Kirin Beer Kabushiki Kaisha | Nitrogen-containing compounds having kinase inhibitory activity and drugs containing the same |
| US7105682B2 (en) | 2001-01-12 | 2006-09-12 | Amgen Inc. | Substituted amine derivatives and methods of use |
| CA2443918C (en) * | 2001-04-11 | 2012-06-05 | Senju Pharmaceutical Co., Ltd. | Visual function disorder improving agents containing rho kinase inhibitors |
| WO2002083648A1 (fr) * | 2001-04-16 | 2002-10-24 | Eisai Co., Ltd. | Nouveau compose a base de 1h-indazole |
| EP1403255A4 (en) | 2001-06-12 | 2005-04-06 | Sumitomo Pharma | RHO KINASE INHIBITORS |
| US6867221B2 (en) * | 2001-08-30 | 2005-03-15 | Kowa Co., Ltd. | Cyclic amine compounds and pharmaceutical composition containing the same |
| TW200300350A (en) | 2001-11-14 | 2003-06-01 | Bristol Myers Squibb Co | C-5 modified indazolylpyrrolotriazines |
| US20030187026A1 (en) * | 2001-12-13 | 2003-10-02 | Qun Li | Kinase inhibitors |
| KR101160780B1 (ko) | 2002-08-29 | 2012-06-27 | 산텐 세이야꾸 가부시키가이샤 | Ｒｈｏ 키나아제 억제제 및 프로스타글란딘류를 포함하는 녹내장 치료제 |
| CA2502583A1 (en) | 2002-09-12 | 2004-03-25 | Kirin Beer Kabushiki Kaisha | Isoquinoline derivatives having kinase inhibitory activity and medicament containing the same |
| ATE536353T1 (de) * | 2003-08-20 | 2011-12-15 | Vertex Pharma | 2-(4-amino-1,2,5-oxadiazol-4-yl)-imidazol- verbindungen als protein kinase inhibitoren |
| WO2006135383A2 (en) | 2004-08-04 | 2006-12-21 | Myriad Genetics, Inc. | Indazoles |
| US20070054916A1 (en) * | 2004-10-01 | 2007-03-08 | Amgen Inc. | Aryl nitrogen-containing bicyclic compounds and methods of use |
| EP1814856A1 (en) * | 2004-11-12 | 2007-08-08 | Galapagos N.V. | Nitrogen heteroaromatic compounds which bind to the active site of protein kinase enzymes |
| AR054416A1 (es) * | 2004-12-22 | 2007-06-27 | Incyte Corp | Pirrolo [2,3-b]piridin-4-il-aminas y pirrolo [2,3-b]pirimidin-4-il-aminas como inhibidores de las quinasas janus. composiciones farmaceuticas. |
| JP2008545660A (ja) * | 2005-05-20 | 2008-12-18 | バーテックス ファーマシューティカルズ インコーポレイテッド | プロテインキナーゼ阻害剤として有用なピロロピリジン化合物 |
| JP5071374B2 (ja) * | 2005-07-14 | 2012-11-14 | アステラス製薬株式会社 | ヘテロ環ヤヌスキナーゼ３阻害剤 |
| US7618985B2 (en) * | 2005-12-08 | 2009-11-17 | N.V. Organon | Isoquinoline derivatives |
-
2007
- 2007-12-17 US US11/958,214 patent/US8071779B2/en active Active
- 2007-12-18 WO PCT/US2007/087973 patent/WO2008077057A2/en not_active Ceased
- 2007-12-18 BR BRPI0720457-4A patent/BRPI0720457A2/pt not_active IP Right Cessation
- 2007-12-18 CN CN2012105761391A patent/CN103254172A/zh active Pending
- 2007-12-18 RU RU2009127798/04A patent/RU2470928C2/ru not_active IP Right Cessation
- 2007-12-18 CA CA002672825A patent/CA2672825A1/en not_active Abandoned
- 2007-12-18 KR KR1020097012595A patent/KR20090091767A/ko not_active Ceased
- 2007-12-18 MX MX2009006493A patent/MX2009006493A/es unknown
- 2007-12-18 AU AU2007333715A patent/AU2007333715B2/en not_active Ceased
- 2007-12-18 EP EP07869450A patent/EP2099457A4/en not_active Withdrawn
- 2007-12-18 CN CN2007800496081A patent/CN101583361B/zh not_active Expired - Fee Related
- 2007-12-18 JP JP2009541644A patent/JP5511385B2/ja not_active Expired - Fee Related
-
2011
- 2011-10-13 US US13/273,043 patent/US8604218B2/en active Active
-
2012
- 2012-09-13 US US13/614,641 patent/US8604205B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2009127798A (ru) | Цитоскелетно-активные ингибитующие rho-киназу соединения, их композиции и применение | |
| ES2632597T3 (es) | Compuestos intermedios para la preparación de derivados de 1-(acetil)-piperidina y 1-(acetil)-piperazina como fungicidas para usar en la protección de plantas | |
| RU2439068C2 (ru) | Модуляторы mglur5 | |
| JP2011518811A5 (enExample) | ||
| JP2008513500A5 (enExample) | ||
| JP2005536458A5 (enExample) | ||
| CO6150139A2 (es) | Sal de tartrato de 1-[2- fluoruro-4-(trifluorometil)fenil]-3-(3-{[4-metil-5-(4-metil-1,3 oxazol-5-il)-4h-1,2,4-triazol-3 il]tio}propil)-3-azabiciclo[3.1.0]-hexano y a sus solvatos, formulaciones farmaceuticas, procedimientos para su preparacion y su | |
| PE20090297A1 (es) | Derivados de pirazol sustituidos con heteroarilo utiles para tratar trastornos hiperproliferativos y enfermedades asociadas con angiogenesis | |
| JP2013519680A5 (enExample) | ||
| JP2004534035A5 (enExample) | ||
| JP2008511683A5 (enExample) | ||
| JP2007519695A5 (enExample) | ||
| JP2018503661A5 (enExample) | ||
| RU2013108641A (ru) | Способ лечения офтальмологических заболеваний с использованием соединений ингибиторов киназы в пролекарственных формах | |
| JP2011500679A5 (enExample) | ||
| JP2009504791A5 (enExample) | ||
| JP2004537554A5 (enExample) | ||
| RU2004104951A (ru) | Замещенные пиперазиновые соединения и их применение в качестве ингибиторов окисления жирных кислот | |
| JP2015524483A5 (enExample) | ||
| JP2010143943A5 (enExample) | ||
| CA2464367A1 (en) | Bicyclic compounds | |
| JP2007510629A5 (enExample) | ||
| RU2010122320A (ru) | Новые производные 1, 3-дигидро-5-изобензофуранкарбонитрила и фармацевтическая композиция на их основе для лечения преждевременной эякуляции | |
| JP2010519278A5 (enExample) | ||
| JP2004525183A5 (enExample) |