JP2010513319A5 - - Google Patents
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- 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
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- 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
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| 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 |
| CL2008003120A1 (es) * | 2007-11-01 | 2009-10-09 | Acucela Inc | Compuestos derivados de fenilalquil-, fenilalquenil-, fenilalquinil- amina, feniltioalquilamina, fenilaminoalquilamina, fenilalcoxiamina y fenilalquilguanidina; composicion farmaceutica; y uso de los compuestos para tratar un trastorno o enfermedad oftalmologica tal como retinopatia, maculopatia, retinitis pigmentosa, uveitis, entre otras. |
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| US20100008968A1 (en) * | 2008-06-26 | 2010-01-14 | Lampe John W | Method for treating cardiovascular diseases using rho kinase inhibitor compounds |
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| US20090325960A1 (en) * | 2008-06-26 | 2009-12-31 | Fulcher Emilee H | Method for treating inflammatory 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 |
| US20100204210A1 (en) * | 2008-12-04 | 2010-08-12 | Scott Sorensen | Method for treating pulmonary diseases using rho kinase inhibitor compounds |
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| 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 |
| DK2326332T3 (da) * | 2009-06-22 | 2013-03-04 | Dmi Acquistion Corp | Fremgangsmåde til behandling af sygdomme |
| AU2010332010A1 (en) * | 2009-12-14 | 2012-08-02 | Inspire Pharmaceuticals, Inc. | Bridged bicyclic Rho kinase inhibitor compounds, composition and use |
| RU2013107007A (ru) * | 2010-07-19 | 2014-08-27 | Инспайр Фармасьютикалз, Инк. | Бифункциональные соединения, являющиеся ингибиторами rho-киназы, композиция и применение |
| WO2012015760A1 (en) * | 2010-07-27 | 2012-02-02 | Inspire Pharmaceuticals, Inc. | Method for treating ophthalmic diseases using kinase inhibitor compounds in prodrug forms |
| GB201107223D0 (en) | 2011-04-29 | 2011-06-15 | Amakem Nv | Novel rock inhibitors |
| CA3178138A1 (en) | 2011-12-06 | 2013-06-13 | Astellas Institute For Regenerative Medicine | Method of directed differentiation producing corneal endothelial cells, compositions thereof, and uses thereof |
| KR101939710B1 (ko) | 2011-12-21 | 2019-01-17 | 노비라 테라퓨틱스, 인코포레이티드 | B형 간염의 항바이러스성 제제 |
| 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 |
| UY34993A (es) | 2012-08-28 | 2014-02-28 | Janssen R & D Ireland | Sulfamoilarilamidas y su uso como medicamentos para el tratamiento de la hepatitis b |
| ES2617495T3 (es) * | 2012-10-31 | 2017-06-19 | Ph Pharma Co., Ltd. | Nuevos inhibidores de rock |
| CN104968350A (zh) | 2012-12-19 | 2015-10-07 | 安皮奥制药股份有限公司 | 疾病的治疗方法 |
| WO2014131847A1 (en) | 2013-02-28 | 2014-09-04 | Janssen R&D Ireland | Sulfamoyl-arylamides and the use thereof as medicaments for the treatment of hepatitis b |
| US20140275160A1 (en) | 2013-03-15 | 2014-09-18 | Aerie Pharmaceuticals, Inc. | Combination therapy |
| JP6419155B2 (ja) | 2013-04-03 | 2018-11-07 | ヤンセン・サイエンシズ・アイルランド・ユーシー | Ｎ−フェニル−カルボキサミド誘導体およびｂ型肝炎を治療するための医薬品としてのその使用 |
| HRP20181863T1 (hr) | 2013-05-17 | 2018-12-28 | Janssen Sciences Ireland Uc | Derivati sulfamoiltiofenamida i njihova uporaba kao lijekova za liječenje hepatitisa b |
| JO3583B1 (ar) | 2013-05-17 | 2020-07-05 | Janssen Sciences Ireland Uc | مشتقات سلفامويل بيرولاميد واستخدامها كادوية لمعالجة التهاب الكبد نوع بي |
| NO3024819T3 (enExample) | 2013-07-25 | 2018-07-21 | ||
| 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 |
| WO2015120178A1 (en) | 2014-02-05 | 2015-08-13 | Novira Therapeutics, Inc. | Combination therapy for treatment of hbv infections |
| DK3102572T3 (en) | 2014-02-06 | 2019-02-04 | Janssen Sciences Ireland Uc | SULFAMOYLPYRROLAMIDE DERIVATIVES AND THEIR USE AS MEDICINES TO TREAT HEPATITIS B |
| WO2016057306A1 (en) | 2014-10-06 | 2016-04-14 | University Of Houston | Rho associated kinase (rock) inhibitors and their use in treating disease |
| HK1247147A1 (zh) | 2015-03-19 | 2018-09-21 | 诺维拉治疗公司 | 氮杂环辛烷和氮杂环壬烷衍生物以及治疗乙型肝炎感染的方法 |
| 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 |
| CN108430971A (zh) | 2015-09-29 | 2018-08-21 | 诺维拉治疗公司 | 乙型肝炎抗病毒剂的晶体形式 |
| JP6832946B2 (ja) | 2015-11-17 | 2021-02-24 | アエリエ ファーマシューティカルズ インコーポレイテッド | キナーゼ阻害剤およびその中間体の調製方法 |
| US9643927B1 (en) | 2015-11-17 | 2017-05-09 | Aerie Pharmaceuticals, Inc. | Process for the preparation of kinase inhibitors and intermediates thereof |
| KR20180129943A (ko) | 2016-04-15 | 2018-12-05 | 노비라 테라퓨틱스, 인코포레이티드 | 캡시드 조립 억제제를 포함하는 배합물 및 방법 |
| CN109640966A (zh) | 2016-08-31 | 2019-04-16 | 爱瑞制药公司 | 眼用组合物 |
| EP3585790A1 (en) * | 2017-02-27 | 2020-01-01 | Janssen Pharmaceutica NV | [1,2,4]-triazolo [1,5-a]-pyrimidinyl derivatives substituted with piperidine, morpholine or piperazine as oga inhibitors |
| WO2018183911A1 (en) | 2017-03-31 | 2018-10-04 | Aerie Pharmaceuticals, Inc. | Aryl cyclopropyl-amino-isoquinolinyl amide compounds |
| KR102821964B1 (ko) | 2017-11-03 | 2025-06-19 | 어클라리스 쎄라퓨틱스, 인코포레이티드 | 치환된 피롤로피리미딘 jak 억제제 및 이의 제조 및 사용 방법 |
| JP2021515769A (ja) | 2018-03-14 | 2021-06-24 | 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 | カプシド集合調節剤の投薬レジメン |
| 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 |
| EP3833350A4 (en) | 2018-08-10 | 2022-05-18 | Aclaris Therapeutics, Inc. | Pyrrolopyrimidine itk inhibitors |
| US12281308B2 (en) | 2018-08-29 | 2025-04-22 | University Of Massachusetts | Inhibition of protein kinases to treat Friedreich ataxia |
| US11427563B2 (en) | 2018-09-14 | 2022-08-30 | Aerie Pharmaceuticals, Inc. | Aryl cyclopropyl-amino-isoquinolinyl amide compounds |
| US12048678B2 (en) | 2018-10-02 | 2024-07-30 | Case Western Reserve University | Compounds for treating myelin related disorders |
| US11096931B2 (en) | 2019-02-22 | 2021-08-24 | Janssen Sciences Ireland Unlimited Company | Amide derivatives useful in the treatment of HBV infection or HBV-induced diseases |
| US11491148B2 (en) | 2019-05-06 | 2022-11-08 | Janssen Sciences Ireland Unlimited Company | Amide derivatives useful in the treatment of HBV infection or HBV-induced diseases |
| 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 |
| WO2023023532A2 (en) | 2021-08-18 | 2023-02-23 | Chemocentryx, Inc. | Aryl sulfonyl (hydroxy) piperidines as ccr6 inhibitors |
| CN118019735A (zh) | 2021-08-18 | 2024-05-10 | 坎莫森特里克斯公司 | 作为ccr6抑制剂的芳基磺酰基化合物 |
| 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 |
| CA2707827A1 (en) | 2001-04-11 | 2002-10-24 | 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 |
| US7199147B2 (en) | 2001-06-12 | 2007-04-03 | Dainippon Sumitomo Pharma Co., Ltd. | 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 |
| AU2003257588A1 (en) | 2002-08-29 | 2004-03-19 | Santen Pharmaceutical Co., Ltd. | REMEDY FOR GLAUCOMA COMPRISING Rho KINASE INHIBITOR AND PROSTAGLANDINS |
| EP1550660A1 (en) | 2002-09-12 | 2005-07-06 | Kirin Beer Kabushiki Kaisha | Isoquinoline derivatives having kinasae inhibitory activity and drugs containing the same |
| CA2536253A1 (en) | 2003-08-20 | 2005-03-03 | Vertex Pharmaceuticals Incorporated | Aminofurazan compounds useful as protein kinase inhibitors |
| 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 |
| CA2585490A1 (en) * | 2004-11-12 | 2006-05-18 | Galapagos Nv | 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. |
| KR20080016659A (ko) * | 2005-05-20 | 2008-02-21 | 버텍스 파마슈티칼스 인코포레이티드 | 단백질 키나제의 억제제로서 유용한 피롤로피리딘 |
| KR20080026654A (ko) * | 2005-07-14 | 2008-03-25 | 아스텔라스세이야쿠 가부시키가이샤 | 헤테로시클릭 야누스 키나제 3 억제제 |
| 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 CN CN2012105761391A patent/CN103254172A/zh active Pending
- 2007-12-18 BR BRPI0720457-4A patent/BRPI0720457A2/pt not_active IP Right Cessation
- 2007-12-18 KR KR1020097012595A patent/KR20090091767A/ko not_active Ceased
- 2007-12-18 RU RU2009127798/04A patent/RU2470928C2/ru not_active IP Right Cessation
- 2007-12-18 WO PCT/US2007/087973 patent/WO2008077057A2/en not_active Ceased
- 2007-12-18 MX MX2009006493A patent/MX2009006493A/es unknown
- 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
- 2007-12-18 CA CA002672825A patent/CA2672825A1/en not_active Abandoned
- 2007-12-18 AU AU2007333715A patent/AU2007333715B2/en not_active Ceased
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2011
- 2011-10-13 US US13/273,043 patent/US8604218B2/en active Active
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