AU2012204843A1 - Novel sulfamide piperazine derivatives as protein tyrosine kinase inhibitors and pharmaceutical use thereof - Google Patents

Info

Publication number

AU2012204843A1

AU2012204843A1 AU2012204843A AU2012204843A AU2012204843A1 AU 2012204843 A1 AU2012204843 A1 AU 2012204843A1 AU 2012204843 A AU2012204843 A AU 2012204843A AU 2012204843 A AU2012204843 A AU 2012204843A AU 2012204843 A1 AU2012204843 A1 AU 2012204843A1

Authority

AU

Australia

Prior art keywords

methyl

pyrrolo

pyrimidin

octane

octa

Prior art date

2011-01-07

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• RNFIBTDXEXGJBV-UHFFFAOYSA-N piperazine;sulfamide Chemical class NS(N)(=O)=O.C1CNCCN1 RNFIBTDXEXGJBV-UHFFFAOYSA-N 0.000 title description 2
• 239000005483 tyrosine kinase inhibitor Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 328
• -1 cyano, hydroxy Chemical group 0.000 claims description 228
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 226
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 152
• 125000000217 alkyl group Chemical group 0.000 claims description 116
• 125000000623 heterocyclic group Chemical group 0.000 claims description 109
• 229940124530 sulfonamide Drugs 0.000 claims description 93
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 63
• 238000000034 method Methods 0.000 claims description 59
• 125000003118 aryl group Chemical group 0.000 claims description 58
• 229910052739 hydrogen Inorganic materials 0.000 claims description 58
• 239000001257 hydrogen Substances 0.000 claims description 57
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 56
• 239000000203 mixture Substances 0.000 claims description 53
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 51
• 125000001072 heteroaryl group Chemical group 0.000 claims description 49
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 42
• 125000004043 oxo group Chemical group O=* 0.000 claims description 40
• 229910052736 halogen Inorganic materials 0.000 claims description 39
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 36
• JALJYLNIVJITOC-UHFFFAOYSA-N 7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonic acid Chemical compound OS(=O)(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 JALJYLNIVJITOC-UHFFFAOYSA-N 0.000 claims description 30
• 150000002431 hydrogen Chemical group 0.000 claims description 30
• 125000001424 substituent group Chemical group 0.000 claims description 30
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 30
• 238000011282 treatment Methods 0.000 claims description 30
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
• IMHPOXSWOGMMNZ-UHFFFAOYSA-N 1,2-diazaspiro[2.5]octane-4-sulfonamide Chemical compound N1NC12CCCCC2S(=O)(=O)N IMHPOXSWOGMMNZ-UHFFFAOYSA-N 0.000 claims description 21
• 208000023275 Autoimmune disease Diseases 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 18
• 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 claims description 18
• BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 17
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 17
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 17
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
• 201000010099 disease Diseases 0.000 claims description 17
• 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 claims description 16
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 101000844245 Homo sapiens Non-receptor tyrosine-protein kinase TYK2 Proteins 0.000 claims description 14
• 101000997835 Homo sapiens Tyrosine-protein kinase JAK1 Proteins 0.000 claims description 14
• 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 claims description 14
• 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims description 14
• 150000003839 salts Chemical class 0.000 claims description 14
• 206010028980 Neoplasm Diseases 0.000 claims description 13
• 201000011510 cancer Diseases 0.000 claims description 13
• 238000011321 prophylaxis Methods 0.000 claims description 13
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
• 102100033438 Tyrosine-protein kinase JAK1 Human genes 0.000 claims description 12
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 12
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
• 206010012601 diabetes mellitus Diseases 0.000 claims description 11
• 201000004681 Psoriasis Diseases 0.000 claims description 10
• 125000004104 aryloxy group Chemical group 0.000 claims description 10
• 230000001363 autoimmune Effects 0.000 claims description 10
• 125000002393 azetidinyl group Chemical group 0.000 claims description 10
• 125000001153 fluoro group Chemical group F* 0.000 claims description 10
• 210000000987 immune system Anatomy 0.000 claims description 10
• 201000006417 multiple sclerosis Diseases 0.000 claims description 10
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 9
• 102000042838 JAK family Human genes 0.000 claims description 9
• 108091082332 JAK family Proteins 0.000 claims description 9
• 108091000080 Phosphotransferase Proteins 0.000 claims description 9
• 201000008937 atopic dermatitis Diseases 0.000 claims description 9
• 230000000694 effects Effects 0.000 claims description 9
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
• 102000020233 phosphotransferase Human genes 0.000 claims description 9
• 150000003456 sulfonamides Chemical class 0.000 claims description 9
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 8
• 208000024827 Alzheimer disease Diseases 0.000 claims description 8
• 208000011231 Crohn disease Diseases 0.000 claims description 8
• 241001303601 Rosacea Species 0.000 claims description 8
• 208000024799 Thyroid disease Diseases 0.000 claims description 8
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 8
• 208000006673 asthma Diseases 0.000 claims description 8
• 208000030533 eye disease Diseases 0.000 claims description 8
• 208000015181 infectious disease Diseases 0.000 claims description 8
• 230000002458 infectious effect Effects 0.000 claims description 8
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
• 208000032839 leukemia Diseases 0.000 claims description 8
• 206010025135 lupus erythematosus Diseases 0.000 claims description 8
• 208000002780 macular degeneration Diseases 0.000 claims description 8
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 8
• 201000004700 rosacea Diseases 0.000 claims description 8
• 208000017520 skin disease Diseases 0.000 claims description 8
• 239000012453 solvate Substances 0.000 claims description 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
• OEXDCSYVQCRQNO-UHFFFAOYSA-N 7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound NS(=O)(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 OEXDCSYVQCRQNO-UHFFFAOYSA-N 0.000 claims description 7
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 7
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 7
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 7
• 239000002253 acid Substances 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 238000002560 therapeutic procedure Methods 0.000 claims description 7
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 6
• 201000004624 Dermatitis Diseases 0.000 claims description 6
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 6
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 208000027866 inflammatory disease Diseases 0.000 claims description 6
• TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
• 230000001684 chronic effect Effects 0.000 claims description 5
• 230000002757 inflammatory effect Effects 0.000 claims description 5
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Chemical compound OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 5
• UPBPAKISEVOITE-MSXFZWOLSA-N (NZ)-N-[(4-methoxyphenyl)methylidene]-7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1=CC(OC)=CC=C1\C=N/S(=O)(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 UPBPAKISEVOITE-MSXFZWOLSA-N 0.000 claims description 4
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
• 206010039705 Scleritis Diseases 0.000 claims description 4
• 206010040799 Skin atrophy Diseases 0.000 claims description 4
• 230000001154 acute effect Effects 0.000 claims description 4
• 230000032683 aging Effects 0.000 claims description 4
• 229940121363 anti-inflammatory agent Drugs 0.000 claims description 4
• 239000002260 anti-inflammatory agent Substances 0.000 claims description 4
• 208000010668 atopic eczema Diseases 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 4
• QPZVZKSXBBMCRM-UHFFFAOYSA-N n-(2-phenylethyl)-7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)NCCC1=CC=CC=C1 QPZVZKSXBBMCRM-UHFFFAOYSA-N 0.000 claims description 4
• NYVSWDGDOBILKU-UHFFFAOYSA-N n-(cyanomethyl)-n-(2-phenylethyl)-7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)N(CC#N)CCC1=CC=CC=C1 NYVSWDGDOBILKU-UHFFFAOYSA-N 0.000 claims description 4
• SYSRIKNTGFJCSF-UHFFFAOYSA-N n-methyl-n-(pyrrolidin-3-ylmethyl)-7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)N(C)CC1CCNC1 SYSRIKNTGFJCSF-UHFFFAOYSA-N 0.000 claims description 4
• 125000003566 oxetanyl group Chemical group 0.000 claims description 4
• 102000004169 proteins and genes Human genes 0.000 claims description 4
• 108090000623 proteins and genes Proteins 0.000 claims description 4
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
• VGLIWKLNSIPDPO-UHFFFAOYSA-N 4-(4-imidazol-1-ylsulfonyl-4,7-diazaspiro[2.5]octan-7-yl)-7H-pyrrolo[2,3-d]pyrimidine Chemical compound C1=CN=CN1S(=O)(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 VGLIWKLNSIPDPO-UHFFFAOYSA-N 0.000 claims description 3
• PODDKJDNQSSKHD-UHFFFAOYSA-N 4-(4-piperidin-1-ylsulfonyl-4,7-diazaspiro[2.5]octan-7-yl)-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)N1CCCCC1 PODDKJDNQSSKHD-UHFFFAOYSA-N 0.000 claims description 3
• XFYAOSWNQLKSOT-UHFFFAOYSA-N N-(2-methoxyethyl)-N-(2-phenylethyl)-7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)N(CCOC)CCC1=CC=CC=C1 XFYAOSWNQLKSOT-UHFFFAOYSA-N 0.000 claims description 3
• QFVKMCJXZVMCSP-UHFFFAOYSA-N N-(3-cyanopropyl)-N-(2-phenylethyl)-7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)N(CCCC#N)CCC1=CC=CC=C1 QFVKMCJXZVMCSP-UHFFFAOYSA-N 0.000 claims description 3
• LATMSELDCZIDDC-UHFFFAOYSA-N N-(4-cyanobutyl)-N-(2-phenylethyl)-7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)N(CCCCC#N)CCC1=CC=CC=C1 LATMSELDCZIDDC-UHFFFAOYSA-N 0.000 claims description 3
• YFERPDDHNCYXOF-UHFFFAOYSA-N N-(azetidin-3-yl)-N-methyl-7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)N(C)C1CNC1 YFERPDDHNCYXOF-UHFFFAOYSA-N 0.000 claims description 3
• RAFNKNDYDNGOAD-UHFFFAOYSA-N N-[(2-cyanophenyl)methyl]-N-methyl-7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)N(C)CC1=CC=CC=C1C#N RAFNKNDYDNGOAD-UHFFFAOYSA-N 0.000 claims description 3
• DYWAFADPHCTOEP-UHFFFAOYSA-N N-[3-(3-cyanophenyl)propyl]-N-methyl-7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)N(C)CCCC1=CC=CC(C#N)=C1 DYWAFADPHCTOEP-UHFFFAOYSA-N 0.000 claims description 3
• FRGOJTCBTIPUFW-UHFFFAOYSA-N N-[3-(4-cyanophenyl)propyl]-N-methyl-7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)N(C)CCCC1=CC=C(C#N)C=C1 FRGOJTCBTIPUFW-UHFFFAOYSA-N 0.000 claims description 3
• 241000534944 Thia Species 0.000 claims description 3
• 206010052779 Transplant rejections Diseases 0.000 claims description 3
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 3
• 230000002500 effect on skin Effects 0.000 claims description 3
• JGHFRGJGSGRUHV-UHFFFAOYSA-N ethyl 2-[2-phenylethyl-[[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]sulfonyl]amino]acetate Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)N(CC(=O)OCC)CCC1=CC=CC=C1 JGHFRGJGSGRUHV-UHFFFAOYSA-N 0.000 claims description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000002757 morpholinyl group Chemical group 0.000 claims description 3
• NMEYIHPSPMHXGR-UHFFFAOYSA-N n,n-dimethyl-2-[methyl-[[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]sulfonyl]amino]acetamide Chemical compound CN(C)C(=O)CN(C)S(=O)(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 NMEYIHPSPMHXGR-UHFFFAOYSA-N 0.000 claims description 3
• OXLLIFVNWVIAQB-UHFFFAOYSA-N n-(2-methylpropyl)-n-(2-phenylethyl)-7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)N(CC(C)C)CCC1=CC=CC=C1 OXLLIFVNWVIAQB-UHFFFAOYSA-N 0.000 claims description 3
• YKPBEWKMOVHBLR-UHFFFAOYSA-N n-(2-phenylethyl)-n-(2-pyrazol-1-ylethyl)-7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)N(CCN1N=CC=C1)CCC1=CC=CC=C1 YKPBEWKMOVHBLR-UHFFFAOYSA-N 0.000 claims description 3
• IBLNEBOCMPEHLE-UHFFFAOYSA-N n-(2-phenylethyl)-n-(3-phenylpropyl)-7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)N(CCC=1C=CC=CC=1)CCCC1=CC=CC=C1 IBLNEBOCMPEHLE-UHFFFAOYSA-N 0.000 claims description 3
• ACOPWBKJITVHHX-UHFFFAOYSA-N n-(3-cyanopropyl)-n-(3-phenylpropyl)-7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)N(CCCC#N)CCCC1=CC=CC=C1 ACOPWBKJITVHHX-UHFFFAOYSA-N 0.000 claims description 3
• MPINDTZZSIHGQS-UHFFFAOYSA-N n-(cyanomethyl)-n-(2-hydroxyethyl)-7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound OCCN(CC#N)S(=O)(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 MPINDTZZSIHGQS-UHFFFAOYSA-N 0.000 claims description 3
• NICFBFHTBZISBG-UHFFFAOYSA-N n-(cyanomethyl)-n-cyclobutyl-7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)N(CC#N)C1CCC1 NICFBFHTBZISBG-UHFFFAOYSA-N 0.000 claims description 3
• DCNSJGOMFIRNTM-UHFFFAOYSA-N n-(cyclobutylmethyl)-n-(2-phenylethyl)-7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)N(CC1CCC1)CCC1=CC=CC=C1 DCNSJGOMFIRNTM-UHFFFAOYSA-N 0.000 claims description 3
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