AU2007333715B2 - Cytoskeletal active rho kinase inhibitor compounds, composition and use - Google Patents

Info

Publication number

AU2007333715B2

AU2007333715B2 AU2007333715A AU2007333715A AU2007333715B2 AU 2007333715 B2 AU2007333715 B2 AU 2007333715B2 AU 2007333715 A AU2007333715 A AU 2007333715A AU 2007333715 A AU2007333715 A AU 2007333715A AU 2007333715 B2 AU2007333715 B2 AU 2007333715B2

Authority

AU

Australia

Prior art keywords

compound

indazol

piperidin

heterocycle

ylamino

Prior art date

2006-12-18

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.)

Ceased

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 347
• 230000003436 cytoskeletal effect Effects 0.000 title abstract description 13
• 239000000203 mixture Substances 0.000 title description 32
• 239000003590 rho kinase inhibitor Substances 0.000 title description 4
• 238000000034 method Methods 0.000 claims abstract description 194
• 230000004410 intraocular pressure Effects 0.000 claims abstract description 38
• 230000003993 interaction Effects 0.000 claims abstract description 19
• 108010043137 Actomyosin Proteins 0.000 claims abstract description 18
• 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 description 321
• 125000000623 heterocyclic group Chemical group 0.000 claims description 276
• 125000000217 alkyl group Chemical group 0.000 claims description 196
• 125000003342 alkenyl group Chemical group 0.000 claims description 157
• 125000000304 alkynyl group Chemical group 0.000 claims description 152
• 125000001424 substituent group Chemical group 0.000 claims description 112
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 104
• 125000001072 heteroaryl group Chemical group 0.000 claims description 99
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 91
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 85
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 83
• 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 82
• 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims description 82
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 80
• 125000003118 aryl group Chemical group 0.000 claims description 80
• -1 (3-(1H-indazol-5-ylamino)pyrrolidin-1-yl)methyl Chemical group 0.000 claims description 79
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 73
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 70
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 69
• 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 68
• 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 68
• 125000005018 aryl alkenyl group Chemical group 0.000 claims description 67
• 125000005015 aryl alkynyl group Chemical group 0.000 claims description 67
• 229910052757 nitrogen Inorganic materials 0.000 claims description 60
• 125000005842 heteroatom Chemical group 0.000 claims description 58
• 150000002367 halogens Chemical class 0.000 claims description 43
• 229910052736 halogen Inorganic materials 0.000 claims description 42
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 40
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 38
• 125000005843 halogen group Chemical group 0.000 claims description 30
• 230000002401 inhibitory effect Effects 0.000 claims description 30
• 229910052717 sulfur Inorganic materials 0.000 claims description 30
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 29
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 27
• 229910052760 oxygen Inorganic materials 0.000 claims description 27
• 239000001301 oxygen Substances 0.000 claims description 27
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 101100203600 Caenorhabditis elegans sor-1 gene Proteins 0.000 claims description 23
• 125000004434 sulfur atom Chemical group 0.000 claims description 23
• 208000010412 Glaucoma Diseases 0.000 claims description 21
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 21
• 125000002015 acyclic group Chemical group 0.000 claims description 20
• 239000012530 fluid Substances 0.000 claims description 20
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 19
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• DTVYNUOOZIKEEX-UHFFFAOYSA-N 5-aminoisoquinoline Chemical compound N1=CC=C2C(N)=CC=CC2=C1 DTVYNUOOZIKEEX-UHFFFAOYSA-N 0.000 claims description 17
• 230000033115 angiogenesis Effects 0.000 claims description 16
• 230000029663 wound healing Effects 0.000 claims description 16
• 125000002950 monocyclic group Chemical group 0.000 claims description 15
• 125000004043 oxo group Chemical group O=* 0.000 claims description 15
• XBTOSRUBOXQWBO-UHFFFAOYSA-N 1h-indazol-5-amine Chemical compound NC1=CC=C2NN=CC2=C1 XBTOSRUBOXQWBO-UHFFFAOYSA-N 0.000 claims description 14
• 239000003795 chemical substances by application Substances 0.000 claims description 13
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 13
• 208000002177 Cataract Diseases 0.000 claims description 12
• 206010036346 Posterior capsule opacification Diseases 0.000 claims description 12
• 206010047163 Vasospasm Diseases 0.000 claims description 12
• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 230000000923 atherogenic effect Effects 0.000 claims description 11
• 238000000605 extraction Methods 0.000 claims description 11
• 238000002513 implantation Methods 0.000 claims description 11
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 11
• 230000010412 perfusion Effects 0.000 claims description 11
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
• 230000004112 neuroprotection Effects 0.000 claims description 10
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 10
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
• 150000001721 carbon Chemical group 0.000 claims description 8
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
• 150000001412 amines Chemical class 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
• 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 description 4
• 229940125773 compound 10 Drugs 0.000 claims description 4
• YCNQEIDRNDLZLW-UHFFFAOYSA-N ethyl 2-[3-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC(CN2CC(CCC2)NC=2C=C3C=NNC3=CC=2)=C1 YCNQEIDRNDLZLW-UHFFFAOYSA-N 0.000 claims description 4
• ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims description 4
• 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 description 4
• AJUALODYLMJXKY-JOCHJYFZSA-N n-[(3r)-1-[[3-(diethoxyphosphorylmethoxy)phenyl]methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound CCOP(=O)(OCC)COC1=CC=CC(CN2C[C@@H](CCC2)NC=2C=C3C=NNC3=CC=2)=C1 AJUALODYLMJXKY-JOCHJYFZSA-N 0.000 claims description 4
• 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 description 4
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• XJBMIEOOJSNFLV-GOSISDBHSA-N 2-[3-[[(3r)-3-(isoquinolin-5-ylamino)pyrrolidin-1-yl]methyl]phenoxy]acetamide Chemical compound NC(=O)COC1=CC=CC(CN2C[C@@H](CC2)NC=2C3=CC=NC=C3C=CC=2)=C1 XJBMIEOOJSNFLV-GOSISDBHSA-N 0.000 claims description 3
• 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 description 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• NFKDKPROTAFVJH-HXUWFJFHSA-N 2-[6-[[(3r)-3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]indol-1-yl]acetamide Chemical compound C1=C2NN=CC2=CC(N[C@@H]2CCCN(C2)CC2=CC=C3C=CN(C3=C2)CC(=O)N)=C1 NFKDKPROTAFVJH-HXUWFJFHSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• GGWYWWPWWDQMKJ-UHFFFAOYSA-N 3-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]benzamide Chemical compound NC(=O)C1=CC=CC(CN2CC(CCC2)NC=2C=C3C=NNC3=CC=2)=C1 GGWYWWPWWDQMKJ-UHFFFAOYSA-N 0.000 claims description 3
• JSQRFMBGAVZKFV-UHFFFAOYSA-N 3-[[3-(1h-indazol-5-ylamino)piperidin-1-yl]methyl]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(CN2CC(CCC2)NC=2C=C3C=NNC3=CC=2)=C1 JSQRFMBGAVZKFV-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 239000004146 Propane-1,2-diol Substances 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• DPZSYTMLVCLGRU-UHFFFAOYSA-N n-[1-[(4-methylsulfanylphenyl)methyl]piperidin-3-yl]-1h-indazol-5-amine Chemical compound C1=CC(SC)=CC=C1CN1CC(NC=2C=C3C=NNC3=CC=2)CCC1 DPZSYTMLVCLGRU-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
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