CA2714888C - Pyrimidyl cyclopentanes as akt protein kinase inhibitors - Google Patents

Info

Publication number

CA2714888C

CA2714888C CA2714888A CA2714888A CA2714888C CA 2714888 C CA2714888 C CA 2714888C CA 2714888 A CA2714888 A CA 2714888A CA 2714888 A CA2714888 A CA 2714888A CA 2714888 C CA2714888 C CA 2714888C

Authority

CA

Canada

Prior art keywords

methyl

indoline

dihydro

cyclopenta

pyrimidin

Prior art date

2008-01-09

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.)

Expired - Fee Related

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• 108091008611 Protein Kinase B Proteins 0.000 title claims abstract description 61
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title abstract description 4
• 239000003909 protein kinase inhibitor Substances 0.000 title abstract description 4
• -1 Pyrimidyl cyclopentanes Chemical class 0.000 title description 97
• 150000001875 compounds Chemical class 0.000 claims abstract description 259
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 72
• 150000003839 salts Chemical class 0.000 claims abstract description 48
• 201000010099 disease Diseases 0.000 claims abstract description 45
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 31
• 201000011510 cancer Diseases 0.000 claims abstract description 22
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 17
• 239000012453 solvate Substances 0.000 claims abstract description 12
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 9
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 137
• 239000000203 mixture Substances 0.000 claims description 130
• 125000003003 spiro group Chemical group 0.000 claims description 116
• JHMKGUPCKJSSEF-UHFFFAOYSA-N spiro[1,2-dihydroindole-3,4'-piperidine] Chemical compound C1NC2=CC=CC=C2C11CCNCC1 JHMKGUPCKJSSEF-UHFFFAOYSA-N 0.000 claims description 97
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 52
• 125000003118 aryl group Chemical group 0.000 claims description 47
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 37
• 229910052731 fluorine Inorganic materials 0.000 claims description 36
• 125000000623 heterocyclic group Chemical group 0.000 claims description 35
• 239000008194 pharmaceutical composition Substances 0.000 claims description 35
• 125000000217 alkyl group Chemical group 0.000 claims description 33
• 229910052794 bromium Inorganic materials 0.000 claims description 32
• 229910052801 chlorine Inorganic materials 0.000 claims description 29
• 239000003814 drug Substances 0.000 claims description 29
• 229910052740 iodine Inorganic materials 0.000 claims description 29
• 208000035475 disorder Diseases 0.000 claims description 27
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 21
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 21
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 230000000694 effects Effects 0.000 claims description 17
• 108091000080 Phosphotransferase Proteins 0.000 claims description 15
• 102000020233 phosphotransferase Human genes 0.000 claims description 15
• 210000004027 cell Anatomy 0.000 claims description 14
• 239000003795 chemical substances by application Substances 0.000 claims description 13
• 125000001072 heteroaryl group Chemical group 0.000 claims description 13
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• 230000005764 inhibitory process Effects 0.000 claims description 12
• 101100322915 Caenorhabditis elegans akt-1 gene Proteins 0.000 claims description 10
• 208000009956 adenocarcinoma Diseases 0.000 claims description 10
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
• 229940124597 therapeutic agent Drugs 0.000 claims description 10
• 206010039491 Sarcoma Diseases 0.000 claims description 9
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 8
• 206010041823 squamous cell carcinoma Diseases 0.000 claims description 8
• 239000003981 vehicle Substances 0.000 claims description 8
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
• 101100162366 Caenorhabditis elegans akt-2 gene Proteins 0.000 claims description 7
• 201000009030 Carcinoma Diseases 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 6
• 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 6
• 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 6
• VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 6
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 6
• 210000004072 lung Anatomy 0.000 claims description 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• 201000004681 Psoriasis Diseases 0.000 claims description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 210000002307 prostate Anatomy 0.000 claims description 5
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 4
• 239000002671 adjuvant Substances 0.000 claims description 4
• 210000001072 colon Anatomy 0.000 claims description 4
• 201000001441 melanoma Diseases 0.000 claims description 4
• 206010001233 Adenoma benign Diseases 0.000 claims description 3
• 208000024827 Alzheimer disease Diseases 0.000 claims description 3
• 201000001320 Atherosclerosis Diseases 0.000 claims description 3
• 210000004556 brain Anatomy 0.000 claims description 3
• 210000000481 breast Anatomy 0.000 claims description 3
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• 230000002496 gastric effect Effects 0.000 claims description 3
• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 3
• 210000000214 mouth Anatomy 0.000 claims description 3
• 210000000056 organ Anatomy 0.000 claims description 3
• 208000037803 restenosis Diseases 0.000 claims description 3
• PXDBDBMRDICFHQ-CQSZACIVSA-N 1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-4-carbonitrile Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=C2C(=CC=C1)C#N)CC12CCNCC1 PXDBDBMRDICFHQ-CQSZACIVSA-N 0.000 claims description 2
• NTJVBDOLKOACBN-CQSZACIVSA-N 1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-5-carbonitrile Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(C=C11)C#N)CC21CCNCC2 NTJVBDOLKOACBN-CQSZACIVSA-N 0.000 claims description 2
• BVGWPGWXIHSDFT-CYBMUJFWSA-N 1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-5-carboxamide Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(C=C11)C(N)=O)CC21CCNCC2 BVGWPGWXIHSDFT-CYBMUJFWSA-N 0.000 claims description 2
• PXJBTOPLGPEHTL-CYBMUJFWSA-N 1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-5-ol Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(O)C=C11)CC21CCNCC2 PXJBTOPLGPEHTL-CYBMUJFWSA-N 0.000 claims description 2
• GGZCAJVJBUQSAN-CQSZACIVSA-N 2-[1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-5-yl]oxyacetamide Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(OCC(N)=O)C=C11)CC21CCNCC2 GGZCAJVJBUQSAN-CQSZACIVSA-N 0.000 claims description 2
• VWASTLFRTNZCLA-CYBMUJFWSA-N 5-bromo-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(Br)C=C11)CC21CCNCC2 VWASTLFRTNZCLA-CYBMUJFWSA-N 0.000 claims description 2
• XATMNHOGMFTHIQ-CYBMUJFWSA-N 5-chloro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(Cl)C=C11)CC21CCNCC2 XATMNHOGMFTHIQ-CYBMUJFWSA-N 0.000 claims description 2
• 208000003200 Adenoma Diseases 0.000 claims description 2
• 208000023275 Autoimmune disease Diseases 0.000 claims description 2
• 208000017604 Hodgkin disease Diseases 0.000 claims description 2
• 206010061218 Inflammation Diseases 0.000 claims description 2
• 208000018737 Parkinson disease Diseases 0.000 claims description 2
• 201000010208 Seminoma Diseases 0.000 claims description 2
• 230000001028 anti-proliverative effect Effects 0.000 claims description 2
• 210000000988 bone and bone Anatomy 0.000 claims description 2
• 210000003679 cervix uteri Anatomy 0.000 claims description 2
• 210000003238 esophagus Anatomy 0.000 claims description 2
• 125000006437 ethyl cyclopropyl group Chemical group 0.000 claims description 2
• 229940088597 hormone Drugs 0.000 claims description 2
• 239000005556 hormone Substances 0.000 claims description 2
• 230000004054 inflammatory process Effects 0.000 claims description 2
• 210000003734 kidney Anatomy 0.000 claims description 2
• 208000032839 leukemia Diseases 0.000 claims description 2
• 210000004185 liver Anatomy 0.000 claims description 2
• 125000006431 methyl cyclopropyl group Chemical group 0.000 claims description 2
• VURZMYBEGLIJGU-OAHLLOKOSA-N n-[[1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-5-yl]methyl]acetamide Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(CNC(C)=O)C=C11)CC21CCNCC2 VURZMYBEGLIJGU-OAHLLOKOSA-N 0.000 claims description 2
• 210000001672 ovary Anatomy 0.000 claims description 2
• 210000000496 pancreas Anatomy 0.000 claims description 2
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
• 210000000664 rectum Anatomy 0.000 claims description 2
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
• 210000002784 stomach Anatomy 0.000 claims description 2
• 210000001550 testis Anatomy 0.000 claims description 2
• 230000003612 virological effect Effects 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
• 208000024172 Cardiovascular disease Diseases 0.000 claims 3
• 208000015122 neurodegenerative disease Diseases 0.000 claims 3
• VFKHNGZYFPVEPS-VQIMIIECSA-N (5r,7r)-5-methyl-4-[4-[(propan-2-ylamino)methyl]spiro[2h-indole-3,4'-piperidine]-1-yl]-6,7-dihydro-5h-cyclopenta[d]pyrimidin-7-ol Chemical compound C1=2C(CNC(C)C)=CC=CC=2N(C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CC21CCNCC2 VFKHNGZYFPVEPS-VQIMIIECSA-N 0.000 claims 2
• 208000029462 Immunodeficiency disease Diseases 0.000 claims 2
• 206010012601 diabetes mellitus Diseases 0.000 claims 2
• 208000014829 head and neck neoplasm Diseases 0.000 claims 2
• 208000019423 liver disease Diseases 0.000 claims 2
• 230000004770 neurodegeneration Effects 0.000 claims 2
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
• 210000003800 pharynx Anatomy 0.000 claims 2
• 210000001685 thyroid gland Anatomy 0.000 claims 2
• CIYQEURPTVHUDC-IUUIHGGBSA-N (2'r,3s)-5-chloro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]-2'-phenylspiro[2h-indole-3,3'-pyrrolidine] Chemical compound C1([C@H]2NCC[C@]22CN(C3=CC=C(Cl)C=C32)C=2N=CN=C3CC[C@H](C=23)C)=CC=CC=C1 CIYQEURPTVHUDC-IUUIHGGBSA-N 0.000 claims 1
• CIYQEURPTVHUDC-PWBHZWRTSA-N (2's,3s)-5-chloro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]-2'-phenylspiro[2h-indole-3,3'-pyrrolidine] Chemical compound C1([C@@H]2NCC[C@]22CN(C3=CC=C(Cl)C=C32)C=2N=CN=C3CC[C@H](C=23)C)=CC=CC=C1 CIYQEURPTVHUDC-PWBHZWRTSA-N 0.000 claims 1
• BTFAVOGGBKYWBK-WXTAPIANSA-N (3r)-1'-benzyl-5-chloro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,3'-pyrrolidine] Chemical compound C([C@]1(CN(C2=CC=C(Cl)C=C21)C=1N=CN=C2CC[C@H](C=12)C)C1)CN1CC1=CC=CC=C1 BTFAVOGGBKYWBK-WXTAPIANSA-N 0.000 claims 1
• JVOVSFLQQWIRFB-KECVGCMWSA-N (3r)-3-(4-chlorophenyl)-3-[(3r)-5-fluoro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,3'-piperidine]-1'-yl]propan-1-amine Chemical compound C1([C@@H](CCN)N2CCC[C@]3(CN(C4=CC=C(F)C=C43)C=3N=CN=C4CC[C@H](C=34)C)C2)=CC=C(Cl)C=C1 JVOVSFLQQWIRFB-KECVGCMWSA-N 0.000 claims 1
• JGEDZLJLAJGANY-ZUOKHONESA-N (3r)-5-chloro-1'-methyl-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,3'-pyrrolidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(Cl)C=C11)C[C@@]21CCN(C)C2 JGEDZLJLAJGANY-ZUOKHONESA-N 0.000 claims 1
• RHCCOTJQMGRAFO-CWTRNNRKSA-N (3r)-5-chloro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,3'-pyrrolidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(Cl)C=C11)C[C@@]21CCNC2 RHCCOTJQMGRAFO-CWTRNNRKSA-N 0.000 claims 1
• FMDLUAOMVAWXAF-SPLOXXLWSA-N (3r)-5-fluoro-1'-methyl-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,3'-piperidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(F)C=C11)C[C@@]21CCCN(C)C2 FMDLUAOMVAWXAF-SPLOXXLWSA-N 0.000 claims 1
• KDSDVNYISAQTNU-ZUOKHONESA-N (3r)-5-fluoro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,3'-piperidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(F)C=C11)C[C@@]21CCCNC2 KDSDVNYISAQTNU-ZUOKHONESA-N 0.000 claims 1
• BTFAVOGGBKYWBK-DWXRJYCRSA-N (3s)-1'-benzyl-5-chloro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,3'-pyrrolidine] Chemical compound C([C@@]1(CN(C2=CC=C(Cl)C=C21)C=1N=CN=C2CC[C@H](C=12)C)C1)CN1CC1=CC=CC=C1 BTFAVOGGBKYWBK-DWXRJYCRSA-N 0.000 claims 1
• JVOVSFLQQWIRFB-RXIOXGHVSA-N (3s)-3-(4-chlorophenyl)-3-[(3r)-5-fluoro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,3'-piperidine]-1'-yl]propan-1-amine Chemical compound C1([C@H](CCN)N2CCC[C@]3(CN(C4=CC=C(F)C=C43)C=3N=CN=C4CC[C@H](C=34)C)C2)=CC=C(Cl)C=C1 JVOVSFLQQWIRFB-RXIOXGHVSA-N 0.000 claims 1
• JGEDZLJLAJGANY-XCLFUZPHSA-N (3s)-5-chloro-1'-methyl-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,3'-pyrrolidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(Cl)C=C11)C[C@]21CCN(C)C2 JGEDZLJLAJGANY-XCLFUZPHSA-N 0.000 claims 1
• RHCCOTJQMGRAFO-BLVKFPJESA-N (3s)-5-chloro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,3'-pyrrolidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(Cl)C=C11)C[C@]21CCNC2 RHCCOTJQMGRAFO-BLVKFPJESA-N 0.000 claims 1
• KDSDVNYISAQTNU-XCLFUZPHSA-N (3s)-5-fluoro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,3'-piperidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(F)C=C11)C[C@]21CCCNC2 KDSDVNYISAQTNU-XCLFUZPHSA-N 0.000 claims 1
• CMZQQNKPDGPZPW-BLXRZLIXSA-N (5r,7r)-4-(2'-benzyl-5-chlorospiro[2h-indole-3,4'-piperidine]-1-yl)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-7-ol Chemical compound C1([C@H](O)C[C@H](C=21)C)=NC=NC=2N(C1=CC=C(Cl)C=C11)CC1(C1)CCNC1CC1=CC=CC=C1 CMZQQNKPDGPZPW-BLXRZLIXSA-N 0.000 claims 1
• BASYETULZMUEGW-CXAGYDPISA-N (5r,7r)-4-(5-chloro-1'-methylspiro[2h-indole-3,4'-piperidine]-1-yl)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-7-ol Chemical compound C1([C@H](O)C[C@H](C=21)C)=NC=NC=2N(C1=CC=C(Cl)C=C11)CC21CCN(C)CC2 BASYETULZMUEGW-CXAGYDPISA-N 0.000 claims 1
• QQLSXKBZWCKNBE-MDNDKPPQSA-N (5r,7r)-4-(5-chlorospiro[2h-indole-3,3'-pyrrolidine]-1-yl)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-7-ol Chemical compound C1([C@H](O)C[C@H](C=21)C)=NC=NC=2N(C1=CC=C(Cl)C=C11)CC21CCNC2 QQLSXKBZWCKNBE-MDNDKPPQSA-N 0.000 claims 1
• OXHNGOKZNXXJAW-MLGOLLRUSA-N (5r,7r)-4-(5-chlorospiro[2h-indole-3,4'-piperidine]-1-yl)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-7-ol Chemical compound C1([C@H](O)C[C@H](C=21)C)=NC=NC=2N(C1=CC=C(Cl)C=C11)CC21CCNCC2 OXHNGOKZNXXJAW-MLGOLLRUSA-N 0.000 claims 1
• VCUXIXQNZUYVAO-LROULRCXSA-N (5r,7r)-4-[(2's,3s)-2'-(hydroxymethyl)spiro[2h-indole-3,4'-pyrrolidine]-1-yl]-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-7-ol Chemical compound C1([C@H](O)C[C@H](C=21)C)=NC=NC=2N(C1=CC=CC=C11)C[C@@]21CN[C@H](CO)C2 VCUXIXQNZUYVAO-LROULRCXSA-N 0.000 claims 1
• BWPJBBZFBWHULL-AZZHVHCYSA-N (5r,7r)-4-[(2's,3s)-2'-[(r)-(4-chlorophenyl)-hydroxymethyl]spiro[2h-indole-3,4'-pyrrolidine]-1-yl]-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-7-ol Chemical compound C1([C@@H](O)[C@H]2NC[C@]3(CN(C4=CC=CC=C43)C=3N=CN=C4[C@H](O)C[C@H](C=34)C)C2)=CC=C(Cl)C=C1 BWPJBBZFBWHULL-AZZHVHCYSA-N 0.000 claims 1
• BWPJBBZFBWHULL-CDVCLYDWSA-N (5r,7r)-4-[(2's,3s)-2'-[(s)-(4-chlorophenyl)-hydroxymethyl]spiro[2h-indole-3,4'-pyrrolidine]-1-yl]-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-7-ol Chemical compound C1([C@H](O)[C@H]2NC[C@]3(CN(C4=CC=CC=C43)C=3N=CN=C4[C@H](O)C[C@H](C=34)C)C2)=CC=C(Cl)C=C1 BWPJBBZFBWHULL-CDVCLYDWSA-N 0.000 claims 1
• AOSUARAORKVTKK-MLGOLLRUSA-N (5r,7r)-4-[4-(aminomethyl)-5-chlorospiro[2h-indole-3,4'-piperidine]-1-yl]-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-7-ol Chemical compound C1([C@H](O)C[C@H](C=21)C)=NC=NC=2N(C1=C2C(=C(Cl)C=C1)CN)CC12CCNCC1 AOSUARAORKVTKK-MLGOLLRUSA-N 0.000 claims 1
• BNYSLJIDSAEAJZ-CRAIPNDOSA-N (5r,7r)-4-[4-[(dimethylamino)methyl]spiro[2h-indole-3,4'-piperidine]-1-yl]-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-7-ol Chemical compound C1([C@H](O)C[C@H](C=21)C)=NC=NC=2N(C1=C2C(=CC=C1)CN(C)C)CC12CCNCC1 BNYSLJIDSAEAJZ-CRAIPNDOSA-N 0.000 claims 1
• GFAZWQDLFJTDIV-FOIQADDNSA-N (5r,7r)-4-[5-chloro-1'-(cyclopropylmethyl)spiro[2h-indole-3,4'-piperidine]-1-yl]-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-7-ol Chemical compound C1([C@H](O)C[C@H](C=21)C)=NC=NC=2N(C1=CC=C(Cl)C=C11)CC1(CC1)CCN1CC1CC1 GFAZWQDLFJTDIV-FOIQADDNSA-N 0.000 claims 1
• OCWWXJUELTZKJI-DNVCBOLYSA-N (5r,7r)-4-[5-chloro-4-[(propan-2-ylamino)methyl]spiro[2h-indole-3,4'-piperidine]-1-yl]-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-7-ol Chemical compound C=1C=C(Cl)C(CNC(C)C)=C2C=1N(C=1C=3[C@H](C)C[C@@H](O)C=3N=CN=1)CC21CCNCC1 OCWWXJUELTZKJI-DNVCBOLYSA-N 0.000 claims 1
• RSKLVGHFKJHZTP-WZONZLPQSA-N (5r,7r)-5-methyl-4-(5-phenylmethoxyspiro[2h-indole-3,4'-piperidine]-1-yl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-7-ol Chemical compound C1([C@H](O)C[C@H](C=21)C)=NC=NC=2N(C1=CC=C(OCC=2C=CC=CC=2)C=C11)CC21CCNCC2 RSKLVGHFKJHZTP-WZONZLPQSA-N 0.000 claims 1
• OWPDZYLYPSEWTE-OMXJDXKCSA-N (5r,7r)-5-methyl-4-[(3r)-4-[(propan-2-ylamino)methyl]spiro[2h-indole-3,3'-pyrrolidine]-1-yl]-6,7-dihydro-5h-cyclopenta[d]pyrimidin-7-ol Chemical compound C1=2C(CNC(C)C)=CC=CC=2N(C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)C[C@@]21CCNC2 OWPDZYLYPSEWTE-OMXJDXKCSA-N 0.000 claims 1
• UGWOANGMUQTAGK-WAWZGNHOSA-N (5r,7r)-5-methyl-4-[(3r)-4-methylspiro[2h-indole-3,3'-pyrrolidine]-1-yl]-6,7-dihydro-5h-cyclopenta[d]pyrimidin-7-ol Chemical compound C1([C@H](O)C[C@H](C=21)C)=NC=NC=2N(C1=C2C(=CC=C1)C)C[C@@]12CCNC1 UGWOANGMUQTAGK-WAWZGNHOSA-N 0.000 claims 1
• OWPDZYLYPSEWTE-YLEKAMJDSA-N (5r,7r)-5-methyl-4-[(3s)-4-[(propan-2-ylamino)methyl]spiro[2h-indole-3,3'-pyrrolidine]-1-yl]-6,7-dihydro-5h-cyclopenta[d]pyrimidin-7-ol Chemical compound C1=2C(CNC(C)C)=CC=CC=2N(C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)C[C@]21CCNC2 OWPDZYLYPSEWTE-YLEKAMJDSA-N 0.000 claims 1
• OXHNGOKZNXXJAW-WBMJQRKESA-N (5r,7s)-4-(5-chlorospiro[2h-indole-3,4'-piperidine]-1-yl)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-7-ol Chemical compound C1([C@@H](O)C[C@H](C=21)C)=NC=NC=2N(C1=CC=C(Cl)C=C11)CC21CCNCC2 OXHNGOKZNXXJAW-WBMJQRKESA-N 0.000 claims 1
• MQTJECMKSKGEPV-SJLPKXTDSA-N 1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]-4-[(2r)-pyrrolidin-2-yl]spiro[2h-indole-3,4'-piperidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=C2C(=CC=C1)[C@@H]1NCCC1)CC12CCNCC1 MQTJECMKSKGEPV-SJLPKXTDSA-N 0.000 claims 1
• YKHIXJAQBQDQMP-LJQANCHMSA-N 1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]-5-phenylmethoxyspiro[2h-indole-3,4'-piperidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(OCC=2C=CC=CC=2)C=C11)CC21CCNCC2 YKHIXJAQBQDQMP-LJQANCHMSA-N 0.000 claims 1
• XDTVZZIBANFIOP-OAHLLOKOSA-N 2,2-difluoro-n-[[1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-4-yl]methyl]ethanamine Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=C2C(=CC=C1)CNCC(F)F)CC12CCNCC1 XDTVZZIBANFIOP-OAHLLOKOSA-N 0.000 claims 1
• FMMGIRZHCZEGEW-IVZQSRNASA-N 2-[(3r)-5-fluoro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,3'-piperidine]-1'-yl]ethanol Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(F)C=C11)C[C@@]21CCCN(CCO)C2 FMMGIRZHCZEGEW-IVZQSRNASA-N 0.000 claims 1
• MPOPBAKMAMFJBU-CQSZACIVSA-N 2-[1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-5-yl]acetamide Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(CC(N)=O)C=C11)CC21CCNCC2 MPOPBAKMAMFJBU-CQSZACIVSA-N 0.000 claims 1
• SEKSMQYBQXKQQP-OAHLLOKOSA-N 2-[1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-5-yl]ethanamine Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(CCN)C=C11)CC21CCNCC2 SEKSMQYBQXKQQP-OAHLLOKOSA-N 0.000 claims 1
• FUKCEEQQOQIZRB-OAHLLOKOSA-N 2-[1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-5-yl]ethanol Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(CCO)C=C11)CC21CCNCC2 FUKCEEQQOQIZRB-OAHLLOKOSA-N 0.000 claims 1
• SGBGODIIJXSBEZ-OEPVSBQMSA-N 2-[1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-5-yl]oxy-2-phenylethanamine Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(OC(CN)C=2C=CC=CC=2)C=C11)CC21CCNCC2 SGBGODIIJXSBEZ-OEPVSBQMSA-N 0.000 claims 1
• SGZIYIQDZQOFIY-OAHLLOKOSA-N 2-[5-chloro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-1'-yl]ethanol Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(Cl)C=C11)CC21CCN(CCO)CC2 SGZIYIQDZQOFIY-OAHLLOKOSA-N 0.000 claims 1
• OEWUGMFOQVTQBH-MRXNPFEDSA-N 2-[[1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-4-yl]methylamino]ethanol Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=C2C(=CC=C1)CNCCO)CC12CCNCC1 OEWUGMFOQVTQBH-MRXNPFEDSA-N 0.000 claims 1
• MRMAXCFZNDKFSJ-MRXNPFEDSA-N 2-fluoro-n-[[1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-4-yl]methyl]ethanamine Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=C2C(=CC=C1)CNCCF)CC12CCNCC1 MRMAXCFZNDKFSJ-MRXNPFEDSA-N 0.000 claims 1
• NHLOOCMMUHSWRS-GOSISDBHSA-N 2-methyl-n-[[1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-4-yl]methyl]propan-1-amine Chemical compound C1=2C(CNCC(C)C)=CC=CC=2N(C=2C=3[C@H](C)CCC=3N=CN=2)CC21CCNCC2 NHLOOCMMUHSWRS-GOSISDBHSA-N 0.000 claims 1
• DOFBTDSZDQCFTO-MRXNPFEDSA-N 3,3,3-trifluoro-n-[[1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-4-yl]methyl]propan-1-amine Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=C2C(=CC=C1)CNCCC(F)(F)F)CC12CCNCC1 DOFBTDSZDQCFTO-MRXNPFEDSA-N 0.000 claims 1
• GPRQMCAVOZQKBS-QRQCRPRQSA-N 3-[(3s)-5-chloro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,3'-pyrrolidine]-1'-yl]propan-1-amine Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(Cl)C=C11)C[C@]21CCN(CCCN)C2 GPRQMCAVOZQKBS-QRQCRPRQSA-N 0.000 claims 1
• GVRMLHVGEWEIDI-MRXNPFEDSA-N 3-[5-chloro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-1'-yl]propan-1-amine Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(Cl)C=C11)CC21CCN(CCCN)CC2 GVRMLHVGEWEIDI-MRXNPFEDSA-N 0.000 claims 1
• KBKVPYYEWYCXRP-ADRQNKRLSA-N 3-[5-fluoro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,3'-piperidine]-1'-yl]propan-1-amine Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(F)C=C11)CC21CCCN(CCCN)C2 KBKVPYYEWYCXRP-ADRQNKRLSA-N 0.000 claims 1
• YGIXNQNDFMVHCV-HXUWFJFHSA-N 4,4-dimethyl-n-[[1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-4-yl]methyl]cyclohexan-1-amine Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=C2C(=CC=C1)CNC1CCC(C)(C)CC1)CC12CCNCC1 YGIXNQNDFMVHCV-HXUWFJFHSA-N 0.000 claims 1
• JHNPQSUJGXKJLM-GFCCVEGCSA-N 4,5-difluoro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=C2C(=C(F)C=C1)F)CC12CCNCC1 JHNPQSUJGXKJLM-GFCCVEGCSA-N 0.000 claims 1
• KNGMXBHNPBTTOB-GFCCVEGCSA-N 4-bromo-5-chloro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=C2C(=C(Cl)C=C1)Br)CC12CCNCC1 KNGMXBHNPBTTOB-GFCCVEGCSA-N 0.000 claims 1
• FNSPOPNMKFZOEZ-GFCCVEGCSA-N 5,6-difluoro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC(F)=C(F)C=C11)CC21CCNCC2 FNSPOPNMKFZOEZ-GFCCVEGCSA-N 0.000 claims 1
• RHQIODMIALNFGJ-GOSISDBHSA-N 5-[(3-fluorophenyl)methyl]-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(CC=2C=C(F)C=CC=2)C=C11)CC21CCNCC2 RHQIODMIALNFGJ-GOSISDBHSA-N 0.000 claims 1
• FHJAZBSOQMUVLO-MRXNPFEDSA-N 5-chloro-1'-(cyclopropylmethyl)-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(Cl)C=C11)CC1(CC1)CCN1CC1CC1 FHJAZBSOQMUVLO-MRXNPFEDSA-N 0.000 claims 1
• GJHGVIAOMOJRBJ-GOSISDBHSA-N 5-chloro-1'-[(4-chlorophenyl)methyl]-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(Cl)C=C11)CC1(CC1)CCN1CC1=CC=C(Cl)C=C1 GJHGVIAOMOJRBJ-GOSISDBHSA-N 0.000 claims 1
• BSKQROWBULRFDR-CQSZACIVSA-N 5-chloro-1'-methyl-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(Cl)C=C11)CC21CCN(C)CC2 BSKQROWBULRFDR-CQSZACIVSA-N 0.000 claims 1
• SCKYDDYMNJOVPP-MRXNPFEDSA-N 5-chloro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]-1'-propan-2-ylspiro[2h-indole-3,4'-piperidine] Chemical compound C1CN(C(C)C)CCC11C2=CC(Cl)=CC=C2N(C=2C=3[C@H](C)CCC=3N=CN=2)C1 SCKYDDYMNJOVPP-MRXNPFEDSA-N 0.000 claims 1
• UGVRXWVXNMVTHV-CYBMUJFWSA-N 5-chloro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-4-carbonitrile Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=C2C(=C(Cl)C=C1)C#N)CC12CCNCC1 UGVRXWVXNMVTHV-CYBMUJFWSA-N 0.000 claims 1
• SNJWNRBAUDHGNS-IUODEOHRSA-N 5-chloro-1-[(5r,7r)-7-fluoro-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine] Chemical compound C1([C@H](F)C[C@H](C=21)C)=NC=NC=2N(C1=CC=C(Cl)C=C11)CC21CCNCC2 SNJWNRBAUDHGNS-IUODEOHRSA-N 0.000 claims 1
• SNJWNRBAUDHGNS-DOMZBBRYSA-N 5-chloro-1-[(5r,7s)-7-fluoro-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine] Chemical compound C1([C@@H](F)C[C@H](C=21)C)=NC=NC=2N(C1=CC=C(Cl)C=C11)CC21CCNCC2 SNJWNRBAUDHGNS-DOMZBBRYSA-N 0.000 claims 1
• YLJBLMJDJAERNW-GFCCVEGCSA-N 5-chloro-4-fluoro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=C2C(=C(Cl)C=C1)F)CC12CCNCC1 YLJBLMJDJAERNW-GFCCVEGCSA-N 0.000 claims 1
• JSJLTHVPTPJHOT-GFCCVEGCSA-N 5-chloro-6-fluoro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC(F)=C(Cl)C=C11)CC21CCNCC2 JSJLTHVPTPJHOT-GFCCVEGCSA-N 0.000 claims 1
• JQEZVHMVGVUDFS-GFCCVEGCSA-N 5-chloro-7-fluoro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=C(F)C=C(Cl)C=C11)CC21CCNCC2 JQEZVHMVGVUDFS-GFCCVEGCSA-N 0.000 claims 1
• YVGCEMSQTHLNIJ-OAHLLOKOSA-N 5-cyclopropyl-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(C=C11)C2CC2)CC21CCNCC2 YVGCEMSQTHLNIJ-OAHLLOKOSA-N 0.000 claims 1
• OWOQTIGIMGFTBK-OAHLLOKOSA-N 5-ethoxy-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine] Chemical compound C12=CC(OCC)=CC=C2N(C=2C=3[C@H](C)CCC=3N=CN=2)CC21CCNCC2 OWOQTIGIMGFTBK-OAHLLOKOSA-N 0.000 claims 1
• WCYLDZCGIOKXMD-CYBMUJFWSA-N 5-fluoro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine] Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(F)C=C11)CC21CCNCC2 WCYLDZCGIOKXMD-CYBMUJFWSA-N 0.000 claims 1
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• ZSZSXJPPBRTWMO-CQSZACIVSA-N [1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-5-yl]methanamine Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=CC=C(CN)C=C11)CC21CCNCC2 ZSZSXJPPBRTWMO-CQSZACIVSA-N 0.000 claims 1
• VRIKUWYGQFRSMO-CYBMUJFWSA-N [5-chloro-1-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]spiro[2h-indole-3,4'-piperidine]-4-yl]methanamine Chemical compound C([C@H](C=12)C)CC2=NC=NC=1N(C1=C2C(=C(Cl)C=C1)CN)CC12CCNCC1 VRIKUWYGQFRSMO-CYBMUJFWSA-N 0.000 claims 1
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