JP5690823B2 - Ｊａｋ受容体およびタンパク質チロシンキナーゼ阻害薬としての複素環化合物 - Google Patents

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Publication number

JP5690823B2

JP5690823B2 JP2012518753A JP2012518753A JP5690823B2 JP 5690823 B2 JP5690823 B2 JP 5690823B2 JP 2012518753 A JP2012518753 A JP 2012518753A JP 2012518753 A JP2012518753 A JP 2012518753A JP 5690823 B2 JP5690823 B2 JP 5690823B2

Authority

JP

Japan

Prior art keywords

pyrrolo

pyrimidin

diazaspiro

oct

octane

Prior art date

2009-07-08

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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• 102000042838 JAK family Human genes 0.000 title description 8
• 108091082332 JAK family Proteins 0.000 title description 8
• 150000002391 heterocyclic compounds Chemical class 0.000 title description 3
• 239000005483 tyrosine kinase inhibitor Substances 0.000 title 1
• -1 cyano, hydroxy Chemical group 0.000 claims description 278
• 150000001875 compounds Chemical class 0.000 claims description 159
• 229910052739 hydrogen Inorganic materials 0.000 claims description 71
• 239000001257 hydrogen Substances 0.000 claims description 71
• 125000000623 heterocyclic group Chemical group 0.000 claims description 70
• 125000000217 alkyl group Chemical group 0.000 claims description 67
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 64
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 59
• 150000003839 salts Chemical class 0.000 claims description 51
• 239000012453 solvate Substances 0.000 claims description 49
• 125000001072 heteroaryl group Chemical group 0.000 claims description 46
• 229910052736 halogen Inorganic materials 0.000 claims description 44
• 150000002367 halogens Chemical class 0.000 claims description 44
• 125000004432 carbon atom Chemical group C* 0.000 claims description 40
• 125000000304 alkynyl group Chemical group 0.000 claims description 37
• 125000003342 alkenyl group Chemical group 0.000 claims description 36
• 125000003118 aryl group Chemical group 0.000 claims description 35
• 150000002431 hydrogen Chemical class 0.000 claims description 35
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
• 125000004043 oxo group Chemical group O=* 0.000 claims description 32
• 238000011282 treatment Methods 0.000 claims description 27
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
• 208000023275 Autoimmune disease Diseases 0.000 claims description 20
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 19
• 125000001424 substituent group Chemical group 0.000 claims description 19
• 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 claims description 18
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 17
• 229910052760 oxygen Inorganic materials 0.000 claims description 17
• 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 claims description 16
• 125000004104 aryloxy group Chemical group 0.000 claims description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 16
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
• 201000010099 disease Diseases 0.000 claims description 15
• 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
• 125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• 239000003814 drug Substances 0.000 claims description 14
• 125000005418 aryl aryl group Chemical group 0.000 claims description 13
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 13
• 102100033438 Tyrosine-protein kinase JAK1 Human genes 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 12
• 102100026456 POU domain, class 3, transcription factor 3 Human genes 0.000 claims description 11
• 101710133393 POU domain, class 3, transcription factor 3 Proteins 0.000 claims description 11
• 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims description 11
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 11
• 206010028980 Neoplasm Diseases 0.000 claims description 10
• 125000004946 alkenylalkyl group Chemical group 0.000 claims description 10
• 125000005038 alkynylalkyl group Chemical group 0.000 claims description 10
• 125000005018 aryl alkenyl group Chemical group 0.000 claims description 10
• 125000005015 aryl alkynyl group Chemical group 0.000 claims description 10
• 201000011510 cancer Diseases 0.000 claims description 10
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 10
• 206010012601 diabetes mellitus Diseases 0.000 claims description 10
• 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 10
• 125000004449 heterocyclylalkenyl group Chemical group 0.000 claims description 10
• 208000015181 infectious disease Diseases 0.000 claims description 10
• 230000002458 infectious effect Effects 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 9
• 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims description 9
• 230000000694 effects Effects 0.000 claims description 9
• 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 9
• 210000000987 immune system Anatomy 0.000 claims description 9
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• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
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• 125000006413 ring segment Chemical group 0.000 claims description 8
• 201000004624 Dermatitis Diseases 0.000 claims description 7
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 7
• 239000002253 acid Substances 0.000 claims description 7
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• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
• 201000004681 Psoriasis Diseases 0.000 claims description 6
• 150000001408 amides Chemical class 0.000 claims description 6
• 230000001684 chronic effect Effects 0.000 claims description 6
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• GXKZSONBJMNAQR-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-yl-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C1CC2=CC=CC=C2C1C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 GXKZSONBJMNAQR-UHFFFAOYSA-N 0.000 claims description 5
• FRWOSBMAKMQDSL-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-1-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]ethanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CC(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 FRWOSBMAKMQDSL-UHFFFAOYSA-N 0.000 claims description 5
• 208000024827 Alzheimer disease Diseases 0.000 claims description 5
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
• 208000011231 Crohn disease Diseases 0.000 claims description 5
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
• JHPJYTPUCSEZFG-UHFFFAOYSA-N [7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]-(1,2,3,4-tetrahydronaphthalen-1-yl)methanone Chemical compound C1CCC2=CC=CC=C2C1C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 JHPJYTPUCSEZFG-UHFFFAOYSA-N 0.000 claims description 5
• 230000001154 acute effect Effects 0.000 claims description 5
• 229940121363 anti-inflammatory agent Drugs 0.000 claims description 5
• 239000002260 anti-inflammatory agent Substances 0.000 claims description 5
• 208000006673 asthma Diseases 0.000 claims description 5
• 208000032839 leukemia Diseases 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
• 238000002560 therapeutic procedure Methods 0.000 claims description 5
• 125000006655 (C3-C8) heteroaryl group Chemical group 0.000 claims description 4
• BZAIUFWHZFVLKX-UHFFFAOYSA-N 5,6-dihydro-4h-cyclopenta[b]thiophen-2-yl-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanethione Chemical compound C=1C=2CCCC=2SC=1C(=S)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 BZAIUFWHZFVLKX-UHFFFAOYSA-N 0.000 claims description 4
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 4
• 206010040799 Skin atrophy Diseases 0.000 claims description 4
• 208000010668 atopic eczema Diseases 0.000 claims description 4
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 4
• 206010025135 lupus erythematosus Diseases 0.000 claims description 4
• 208000002780 macular degeneration Diseases 0.000 claims description 4
• CIIJBWFCTGDACO-UHFFFAOYSA-N methyl 4-[4-(4-cyanobutanoyl)-4,7-diazaspiro[2.5]octan-7-yl]-7h-pyrrolo[2,3-d]pyrimidine-6-carboxylate Chemical compound N1=CN=C2NC(C(=O)OC)=CC2=C1N(C1)CCN(C(=O)CCCC#N)C21CC2 CIIJBWFCTGDACO-UHFFFAOYSA-N 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• FBOHBMDPMVKPSX-UHFFFAOYSA-N tert-butyl 3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate Chemical compound CC(C)(C)OC(=O)N1C(C2)CCC1CN2C1=NC=NC2=C1C=CN2 FBOHBMDPMVKPSX-UHFFFAOYSA-N 0.000 claims description 4
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• XAVWTKGUTIAESU-UHFFFAOYSA-N (1,1-dioxothian-4-yl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1C(=O)C1CCS(=O)(=O)CC1 XAVWTKGUTIAESU-UHFFFAOYSA-N 0.000 claims description 3
• TYQCANIQEPXVSI-UHFFFAOYSA-N (1-phenylcyclopropyl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C1CC1(C=1C=CC=CC=1)C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 TYQCANIQEPXVSI-UHFFFAOYSA-N 0.000 claims description 3
• VGJWOEGRXCUEPU-UHFFFAOYSA-N (2,3-dimethoxyphenyl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound COC1=CC=CC(C(=O)N2C3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1OC VGJWOEGRXCUEPU-UHFFFAOYSA-N 0.000 claims description 3
• SCDHDBZEMJQRAQ-UHFFFAOYSA-N (2-chloro-4-methylsulfonylphenyl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 SCDHDBZEMJQRAQ-UHFFFAOYSA-N 0.000 claims description 3
• UHRPPNPPEWKKKG-UHFFFAOYSA-N (2-fluoro-4-methylsulfonylphenyl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound FC1=CC(S(=O)(=O)C)=CC=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 UHRPPNPPEWKKKG-UHFFFAOYSA-N 0.000 claims description 3
• UUUUTLHENPSEQJ-UHFFFAOYSA-N (3,5-dimethoxyphenyl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound COC1=CC(OC)=CC(C(=O)N2C3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1 UUUUTLHENPSEQJ-UHFFFAOYSA-N 0.000 claims description 3
• QJIQEOAWLQXUMG-UHFFFAOYSA-N (3-fluoro-4-methylsulfonylphenyl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C1=C(F)C(S(=O)(=O)C)=CC=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 QJIQEOAWLQXUMG-UHFFFAOYSA-N 0.000 claims description 3
• NGVBWWMSIHLCGP-UHFFFAOYSA-N (3-methyl-1-benzothiophen-2-yl)-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone Chemical compound S1C2=CC=CC=C2C(C)=C1C(=O)N1C(C2)CCC1CN2C1=NC=NC2=C1C=CN2 NGVBWWMSIHLCGP-UHFFFAOYSA-N 0.000 claims description 3
• SCIBQICCVMELLP-UHFFFAOYSA-N (3-methyl-4-methylsulfonylphenyl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C1=C(S(C)(=O)=O)C(C)=CC(C(=O)N2C3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1 SCIBQICCVMELLP-UHFFFAOYSA-N 0.000 claims description 3
• OMIWKQNDEXBGNG-UHFFFAOYSA-N (3-methylpyrazin-2-yl)-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone Chemical compound CC1=NC=CN=C1C(=O)N1C2CCC1CN(C=1C=3C=CNC=3N=CN=1)C2 OMIWKQNDEXBGNG-UHFFFAOYSA-N 0.000 claims description 3
• LEWOMMLFZJBXSZ-UHFFFAOYSA-N (3-methylpyrazin-2-yl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound CC1=NC=CN=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 LEWOMMLFZJBXSZ-UHFFFAOYSA-N 0.000 claims description 3
• WUEYXHOFKWVDQD-UHFFFAOYSA-N (3-methylquinoxalin-2-yl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound CC1=NC2=CC=CC=C2N=C1C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 WUEYXHOFKWVDQD-UHFFFAOYSA-N 0.000 claims description 3
• WFLYRFIVHWYTQS-UHFFFAOYSA-N (3-methylsulfonylphenyl)-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone Chemical compound CS(=O)(=O)C1=CC=CC(C(=O)N2C3CCC2CN(C3)C=2C=3C=CNC=3N=CN=2)=C1 WFLYRFIVHWYTQS-UHFFFAOYSA-N 0.000 claims description 3
• DWNDGRNTOKWLMA-UHFFFAOYSA-N (3-methylsulfonylphenyl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound CS(=O)(=O)C1=CC=CC(C(=O)N2C3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1 DWNDGRNTOKWLMA-UHFFFAOYSA-N 0.000 claims description 3
• BRWPFQWKZQTTIT-UHFFFAOYSA-N (3-methylthiophen-2-yl)-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone Chemical compound C1=CSC(C(=O)N2C3CCC2CN(C3)C=2C=3C=CNC=3N=CN=2)=C1C BRWPFQWKZQTTIT-UHFFFAOYSA-N 0.000 claims description 3
• IUFXYHUMOJLHEN-UHFFFAOYSA-N (3-methylthiophen-2-yl)-[7-(1h-pyrrolo[2,3-b]pyridin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C1=CSC(C(=O)N2C3(CC3)CN(CC2)C=2C=3C=CNC=3N=CC=2)=C1C IUFXYHUMOJLHEN-UHFFFAOYSA-N 0.000 claims description 3
• TWXDMIRFBBHLQI-UHFFFAOYSA-N (3-methylthiophen-2-yl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C1=CSC(C(=O)N2C3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1C TWXDMIRFBBHLQI-UHFFFAOYSA-N 0.000 claims description 3
• DYMDLCWINGHUNL-UHFFFAOYSA-N (3-phenylphenyl)-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone Chemical compound C1N(C=2C=3C=CNC=3N=CN=2)CC2CCC1N2C(=O)C(C=1)=CC=CC=1C1=CC=CC=C1 DYMDLCWINGHUNL-UHFFFAOYSA-N 0.000 claims description 3
• MZYJPIIHIMBCGC-UHFFFAOYSA-N (3-phenylphenyl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C=1C=CC(C=2C=CC=CC=2)=CC=1C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 MZYJPIIHIMBCGC-UHFFFAOYSA-N 0.000 claims description 3
• WDIODPMMEWTVCE-UHFFFAOYSA-N (4-cyclopentylsulfonylphenyl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C=1C=C(S(=O)(=O)C2CCCC2)C=CC=1C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 WDIODPMMEWTVCE-UHFFFAOYSA-N 0.000 claims description 3
• ZWEZUZZTRSBSOL-UHFFFAOYSA-N (4-fluoro-1h-indol-2-yl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C=1C=2C(F)=CC=CC=2NC=1C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 ZWEZUZZTRSBSOL-UHFFFAOYSA-N 0.000 claims description 3
• PLFGLRCMSDYPOV-UHFFFAOYSA-N (4-fluoro-3-methylsulfonylphenyl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C1=C(F)C(S(=O)(=O)C)=CC(C(=O)N2C3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1 PLFGLRCMSDYPOV-UHFFFAOYSA-N 0.000 claims description 3
• RVROPJKPULOSOO-UHFFFAOYSA-N (4-hydroxycyclohexyl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C1CC(O)CCC1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 RVROPJKPULOSOO-UHFFFAOYSA-N 0.000 claims description 3
• ASSBVTATDXNZBN-UHFFFAOYSA-N (4-hydroxythiophen-2-yl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound OC1=CSC(C(=O)N2C3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1 ASSBVTATDXNZBN-UHFFFAOYSA-N 0.000 claims description 3
• KQTJKUULTZCDER-UHFFFAOYSA-N (4-methoxythiophen-2-yl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound COC1=CSC(C(=O)N2C3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1 KQTJKUULTZCDER-UHFFFAOYSA-N 0.000 claims description 3
• HJVCWXFBATUEDA-UHFFFAOYSA-N (4-methylsulfonylphenyl)-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)N1C2CCC1CN(C=1C=3C=CNC=3N=CN=1)C2 HJVCWXFBATUEDA-UHFFFAOYSA-N 0.000 claims description 3
• UDRBVXJTJQXFJH-UHFFFAOYSA-N (4-methylsulfonylphenyl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 UDRBVXJTJQXFJH-UHFFFAOYSA-N 0.000 claims description 3
• DHEHVNZIUYKLJA-UHFFFAOYSA-N (4-methylthiophen-2-yl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound CC1=CSC(C(=O)N2C3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1 DHEHVNZIUYKLJA-UHFFFAOYSA-N 0.000 claims description 3
• WYLBYEUHBWQDRU-UHFFFAOYSA-N (4-phenylphenyl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 WYLBYEUHBWQDRU-UHFFFAOYSA-N 0.000 claims description 3
• BKZIOVJQMYEJDG-UHFFFAOYSA-N (5,7-difluoro-1h-indol-2-yl)-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone Chemical compound C=1C2=CC(F)=CC(F)=C2NC=1C(=O)N1C(C2)CCC1CN2C1=NC=NC2=C1C=CN2 BKZIOVJQMYEJDG-UHFFFAOYSA-N 0.000 claims description 3
• BPPSREOIVHBZJC-UHFFFAOYSA-N (5-fluoro-1h-indol-2-yl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C=1C2=CC(F)=CC=C2NC=1C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 BPPSREOIVHBZJC-UHFFFAOYSA-N 0.000 claims description 3
• KSHJKLUTKFAUTR-UHFFFAOYSA-N (5-fluoro-3-methyl-1h-indol-2-yl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound N1C2=CC=C(F)C=C2C(C)=C1C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 KSHJKLUTKFAUTR-UHFFFAOYSA-N 0.000 claims description 3
• YKLCKJCXTVYWCL-UHFFFAOYSA-N (5-fluoro-6-methyl-1h-indol-2-yl)-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone Chemical compound C=1C=2C=C(F)C(C)=CC=2NC=1C(=O)N1C(C2)CCC1CN2C1=NC=NC2=C1C=CN2 YKLCKJCXTVYWCL-UHFFFAOYSA-N 0.000 claims description 3
• UOZVXUHNOQNMIZ-UHFFFAOYSA-N (5-methoxythiophen-2-yl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound S1C(OC)=CC=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 UOZVXUHNOQNMIZ-UHFFFAOYSA-N 0.000 claims description 3
• XREQWEOPAPCJDD-UHFFFAOYSA-N (5-methoxythiophen-3-yl)-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone Chemical compound S1C(OC)=CC(C(=O)N2C3CCC2CN(C3)C=2C=3C=CNC=3N=CN=2)=C1 XREQWEOPAPCJDD-UHFFFAOYSA-N 0.000 claims description 3
• IGHXTOCMLSUOEV-UHFFFAOYSA-N (5-methoxythiophen-3-yl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound S1C(OC)=CC(C(=O)N2C3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1 IGHXTOCMLSUOEV-UHFFFAOYSA-N 0.000 claims description 3
• KYQNRSAFYBKNKM-UHFFFAOYSA-N (5-methyl-1-benzothiophen-2-yl)-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone Chemical compound C=1C2=CC(C)=CC=C2SC=1C(=O)N1C(C2)CCC1CN2C1=NC=NC2=C1C=CN2 KYQNRSAFYBKNKM-UHFFFAOYSA-N 0.000 claims description 3
• REBGSJVUMZBKDI-UHFFFAOYSA-N (5-methyl-1h-indol-2-yl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C=1C2=CC(C)=CC=C2NC=1C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 REBGSJVUMZBKDI-UHFFFAOYSA-N 0.000 claims description 3
• GBOARWOLAVVKLR-UHFFFAOYSA-N (5-methylpyrazin-2-yl)-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone Chemical compound C1=NC(C)=CN=C1C(=O)N1C2CCC1CN(C=1C=3C=CNC=3N=CN=1)C2 GBOARWOLAVVKLR-UHFFFAOYSA-N 0.000 claims description 3
• ADMGTZVHALYHTB-UHFFFAOYSA-N (5-methylpyrazin-2-yl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C1=NC(C)=CN=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 ADMGTZVHALYHTB-UHFFFAOYSA-N 0.000 claims description 3
• YEEBZDOTJXVDBI-UHFFFAOYSA-N (5-methylthiophen-2-yl)-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]methanone Chemical compound S1C(C)=CC=C1C(=O)N1C(CN2C=3C=4C=CNC=4N=CN=3)CC2C1 YEEBZDOTJXVDBI-UHFFFAOYSA-N 0.000 claims description 3
• GVAJMPGXCKJTPB-UHFFFAOYSA-N (5-methylthiophen-2-yl)-[7-(1h-pyrrolo[2,3-b]pyridin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound S1C(C)=CC=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CC=2)CC1 GVAJMPGXCKJTPB-UHFFFAOYSA-N 0.000 claims description 3
• YOHJGBSIVRGDGH-UHFFFAOYSA-N (5-methylthiophen-2-yl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound S1C(C)=CC=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 YOHJGBSIVRGDGH-UHFFFAOYSA-N 0.000 claims description 3
• KHHMOIVSNKODQM-UHFFFAOYSA-N (5-phenylthiophen-2-yl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C=1C=C(C=2C=CC=CC=2)SC=1C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 KHHMOIVSNKODQM-UHFFFAOYSA-N 0.000 claims description 3
• VYVZPZZFLMWQOF-UHFFFAOYSA-N (5-propylthiophen-3-yl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound S1C(CCC)=CC(C(=O)N2C3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1 VYVZPZZFLMWQOF-UHFFFAOYSA-N 0.000 claims description 3
• NODYLSMNAKYHOT-UHFFFAOYSA-N (6-bromo-1,2-benzothiazol-3-yl)-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone Chemical compound N=1SC2=CC(Br)=CC=C2C=1C(=O)N1C(C2)CCC1CN2C1=NC=NC2=C1C=CN2 NODYLSMNAKYHOT-UHFFFAOYSA-N 0.000 claims description 3
• GOTFYBHSZVVYEF-UHFFFAOYSA-N (6-fluoro-1h-indol-2-yl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound N1C2=CC(F)=CC=C2C=C1C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 GOTFYBHSZVVYEF-UHFFFAOYSA-N 0.000 claims description 3
• TWLKUPMWGOWXKG-UHFFFAOYSA-N (6-hydroxynaphthalen-1-yl)-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone Chemical compound C=1C=CC2=CC(O)=CC=C2C=1C(=O)N1C(C2)CCC1CN2C1=NC=NC2=C1C=CN2 TWLKUPMWGOWXKG-UHFFFAOYSA-N 0.000 claims description 3
• KWRFHSFAKGSRST-UHFFFAOYSA-N (6-methylpyrazin-2-yl)-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone Chemical compound CC1=CN=CC(C(=O)N2C3CCC2CN(C3)C=2C=3C=CNC=3N=CN=2)=N1 KWRFHSFAKGSRST-UHFFFAOYSA-N 0.000 claims description 3
• NXKRGYWZHKHJTC-UHFFFAOYSA-N (7-fluoro-1h-indol-2-yl)-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound N1C=2C(F)=CC=CC=2C=C1C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 NXKRGYWZHKHJTC-UHFFFAOYSA-N 0.000 claims description 3
• PUNDYHIBQKUFGZ-UHFFFAOYSA-N 1,3-oxazol-2-yl-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone Chemical compound C1N(C=2C=3C=CNC=3N=CN=2)CC2CCC1N2C(=O)C1=NC=CO1 PUNDYHIBQKUFGZ-UHFFFAOYSA-N 0.000 claims description 3
• PMFQXDQYZIMYKA-UHFFFAOYSA-N 1-[1-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-carbonyl]cyclopropanecarbonyl]pyrrolidine-3-carbonitrile Chemical compound C1CC1(C(=O)N1C2(CC2)CN(CC1)C=1C=2C=CNC=2N=CN=1)C(=O)N1CCC(C#N)C1 PMFQXDQYZIMYKA-UHFFFAOYSA-N 0.000 claims description 3
• YKXBYRBNIALWPU-UHFFFAOYSA-N 1-[2-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-carbonyl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCCC1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 YKXBYRBNIALWPU-UHFFFAOYSA-N 0.000 claims description 3
• PFXZQMUXSPHNKR-UHFFFAOYSA-N 1-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]-2-thiophen-2-ylethanone Chemical compound C1N(C=2C=3C=CNC=3N=CN=2)CC2CCC1N2C(=O)CC1=CC=CS1 PFXZQMUXSPHNKR-UHFFFAOYSA-N 0.000 claims description 3
• PKULRBYJKHTWQT-UHFFFAOYSA-N 1-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]propan-1-one Chemical compound CCC(=O)N1C(C2)CCC1CN2C1=NC=NC2=C1C=CN2 PKULRBYJKHTWQT-UHFFFAOYSA-N 0.000 claims description 3
• GGTNCUQITNXBFN-UHFFFAOYSA-N 1-[3-oxo-3-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]propyl]pyrazole-4-sulfonamide Chemical compound C1=C(S(=O)(=O)N)C=NN1CCC(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 GGTNCUQITNXBFN-UHFFFAOYSA-N 0.000 claims description 3
• WFQGKZYDLOQVSL-UHFFFAOYSA-N 1-[4-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octane-8-carbonyl]thiophen-2-yl]ethanone Chemical compound S1C(C(=O)C)=CC(C(=O)N2C3CCC2CN(C3)C=2C=3C=CNC=3N=CN=2)=C1 WFQGKZYDLOQVSL-UHFFFAOYSA-N 0.000 claims description 3
• GLPAYBDUCFFDAO-UHFFFAOYSA-N 1-[4-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-carbonyl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 GLPAYBDUCFFDAO-UHFFFAOYSA-N 0.000 claims description 3
• QKRXHSMOQCBERI-UHFFFAOYSA-N 1-[5-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carbonyl]cyclopropane-1-carbonitrile Chemical compound C1C(N(C2)C=3C=4C=CNC=4N=CN=3)CC2N1C(=O)C1(C#N)CC1 QKRXHSMOQCBERI-UHFFFAOYSA-N 0.000 claims description 3
• YOHWBQWRQQLZCH-UHFFFAOYSA-N 1-[6-methyl-7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-carbonyl]cyclopropane-1-carbonitrile Chemical compound C1CC21CN(C=1C=3C=CNC=3N=CN=1)C(C)CN2C(=O)C1(C#N)CC1 YOHWBQWRQQLZCH-UHFFFAOYSA-N 0.000 claims description 3
• RWVFDZNYSPLVKS-UHFFFAOYSA-N 1-[7-(1h-pyrrolo[2,3-b]pyridin-4-yl)-4,7-diazaspiro[2.5]octane-4-carbonyl]cyclopropane-1-carbonitrile Chemical compound C1CC1(C#N)C(=O)N1CCN(C=2C=3C=CNC=3N=CC=2)CC11CC1 RWVFDZNYSPLVKS-UHFFFAOYSA-N 0.000 claims description 3
• SQMUOKMUTSHVBQ-UHFFFAOYSA-N 1-[7-(2-amino-7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]-2-[4-(trifluoromethyl)phenyl]ethanone Chemical compound C=12C=CNC2=NC(N)=NC=1N(CC12CC2)CCN1C(=O)CC1=CC=C(C(F)(F)F)C=C1 SQMUOKMUTSHVBQ-UHFFFAOYSA-N 0.000 claims description 3
• OFUMLJHOHOPOTE-UHFFFAOYSA-N 1-[7-(2-amino-7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-carbonyl]cyclopropane-1-carbonitrile Chemical compound C=12C=CNC2=NC(N)=NC=1N(CC12CC2)CCN1C(=O)C1(C#N)CC1 OFUMLJHOHOPOTE-UHFFFAOYSA-N 0.000 claims description 3
• ZXNIZFBAOORZOY-UHFFFAOYSA-N 1-[7-(5-chloro-7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]-2-(4-fluorophenyl)ethanone Chemical compound C1=CC(F)=CC=C1CC(=O)N1C2(CC2)CN(C=2C=3C(Cl)=CNC=3N=CN=2)CC1 ZXNIZFBAOORZOY-UHFFFAOYSA-N 0.000 claims description 3
• YTZJOWVNDIADIO-UHFFFAOYSA-N 1-[7-(5-chloro-7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]-2-[4-(trifluoromethyl)phenyl]ethanone Chemical compound C1=CC(C(F)(F)F)=CC=C1CC(=O)N1C2(CC2)CN(C=2C=3C(Cl)=CNC=3N=CN=2)CC1 YTZJOWVNDIADIO-UHFFFAOYSA-N 0.000 claims description 3
• ILUPOJFBTMSWDL-UHFFFAOYSA-N 1-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]-2-thiophen-2-ylethane-1,2-dione Chemical compound C=1C=CSC=1C(=O)C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 ILUPOJFBTMSWDL-UHFFFAOYSA-N 0.000 claims description 3
• ZKUMFLWUPWSUHI-UHFFFAOYSA-N 1-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-carbonyl]cyclopentane-1-carbonitrile Chemical compound C1CCCC1(C#N)C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 ZKUMFLWUPWSUHI-UHFFFAOYSA-N 0.000 claims description 3
• QHDSGXBLTQLBMG-UHFFFAOYSA-N 1-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-carbonyl]cyclopropane-1-carbonitrile Chemical compound C1CC1(C#N)C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 QHDSGXBLTQLBMG-UHFFFAOYSA-N 0.000 claims description 3
• NNKKOFXDSRWOSB-UHFFFAOYSA-N 1-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-carbonyl]cyclopropane-1-carboxylic acid Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1C(=O)C1(C(=O)O)CC1 NNKKOFXDSRWOSB-UHFFFAOYSA-N 0.000 claims description 3
• PUGPIXISZFCPAT-UHFFFAOYSA-N 1-benzothiophen-2-yl-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone Chemical compound C1=CC=C2SC(C(N3C4CCC3CN(C4)C=3C=4C=CNC=4N=CN=3)=O)=CC2=C1 PUGPIXISZFCPAT-UHFFFAOYSA-N 0.000 claims description 3
• CHWUAXWKSKMICN-UHFFFAOYSA-N 1-benzothiophen-2-yl-[7-(5-methoxy-1h-pyrrolo[2,3-b]pyridin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound COC1=CN=C2NC=CC2=C1N(C1)CCN(C(=O)C=2SC3=CC=CC=C3C=2)C21CC2 CHWUAXWKSKMICN-UHFFFAOYSA-N 0.000 claims description 3
• XOLWZNJDNMLVKA-UHFFFAOYSA-N 1-benzothiophen-2-yl-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C=1C2=CC=CC=C2SC=1C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 XOLWZNJDNMLVKA-UHFFFAOYSA-N 0.000 claims description 3
• CSNBICGYMVCPKW-UHFFFAOYSA-N 1-benzothiophen-2-yl-[9-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-6,9-diazaspiro[4.5]decan-6-yl]methanone Chemical compound C=1C2=CC=CC=C2SC=1C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CCCC1 CSNBICGYMVCPKW-UHFFFAOYSA-N 0.000 claims description 3
• WIAGMDDCANYFEO-UHFFFAOYSA-N 1-benzothiophen-3-yl-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]methanone Chemical compound C1=CC=C2C(C(N3C4CCC3CN(C4)C=3C=4C=CNC=4N=CN=3)=O)=CSC2=C1 WIAGMDDCANYFEO-UHFFFAOYSA-N 0.000 claims description 3
• JBQIXTBMDUTVQV-UHFFFAOYSA-N 1-benzothiophen-3-yl-[7-(1h-pyrrolo[2,3-b]pyridin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C=1SC2=CC=CC=C2C=1C(=O)N1CCN(C=2C=3C=CNC=3N=CC=2)CC11CC1 JBQIXTBMDUTVQV-UHFFFAOYSA-N 0.000 claims description 3
• IVBMADFNLXNLMZ-UHFFFAOYSA-N 1-benzothiophen-3-yl-[7-(5-methoxy-1h-pyrrolo[2,3-b]pyridin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound COC1=CN=C2NC=CC2=C1N(C1)CCN(C(=O)C=2C3=CC=CC=C3SC=2)C21CC2 IVBMADFNLXNLMZ-UHFFFAOYSA-N 0.000 claims description 3
• IEWCGHYDBGTUQH-UHFFFAOYSA-N 1-benzothiophen-3-yl-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C=1SC2=CC=CC=C2C=1C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 IEWCGHYDBGTUQH-UHFFFAOYSA-N 0.000 claims description 3
• CUMUYNPOFLYAPJ-UHFFFAOYSA-N 1-benzothiophen-5-yl-[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]methanone Chemical compound C=1C=C2SC=CC2=CC=1C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 CUMUYNPOFLYAPJ-UHFFFAOYSA-N 0.000 claims description 3
• HUSNRHIKZUGEFM-UHFFFAOYSA-N 1-methyl-5-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octane-8-carbonyl]pyrrole-2-sulfonamide Chemical compound C1=C(S(N)(=O)=O)N(C)C(C(=O)N2C3CCC2CN(C3)C=2C=3C=CNC=3N=CN=2)=C1 HUSNRHIKZUGEFM-UHFFFAOYSA-N 0.000 claims description 3
• WFFJEVBFBIAURF-UHFFFAOYSA-N 1-methyl-5-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octane-8-carbonyl]pyrrole-3-sulfonamide Chemical compound CN1C=C(S(N)(=O)=O)C=C1C(=O)N1C2CCC1CN(C=1C=3C=CNC=3N=CN=1)C2 WFFJEVBFBIAURF-UHFFFAOYSA-N 0.000 claims description 3
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• RHWSMXURASEZNN-UHFFFAOYSA-N [7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC(C(=O)N2C3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)=C1 RHWSMXURASEZNN-UHFFFAOYSA-N 0.000 claims description 3
• GOKDRIFENGUPDD-UHFFFAOYSA-N [7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 GOKDRIFENGUPDD-UHFFFAOYSA-N 0.000 claims description 3
• FAGLONLMGGLXQZ-UHFFFAOYSA-N [7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]-quinoxalin-2-ylmethanone Chemical compound C=1N=C2C=CC=CC2=NC=1C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 FAGLONLMGGLXQZ-UHFFFAOYSA-N 0.000 claims description 3
• YXZUANDUADDKRY-UHFFFAOYSA-N [7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]-thiophen-2-ylmethanone Chemical compound C=1C=CSC=1C(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 YXZUANDUADDKRY-UHFFFAOYSA-N 0.000 claims description 3
• 230000003110 anti-inflammatory effect Effects 0.000 claims description 3
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• UUALHBDAOFQDMW-UHFFFAOYSA-N benzyl 3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate Chemical compound C1N(C=2C=3C=CNC=3N=CN=2)CC2CCC1N2C(=O)OCC1=CC=CC=C1 UUALHBDAOFQDMW-UHFFFAOYSA-N 0.000 claims description 3
• 239000004305 biphenyl Substances 0.000 claims description 3
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• 208000030949 chronic idiopathic urticaria Diseases 0.000 claims description 3
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• 208000024376 chronic urticaria Diseases 0.000 claims description 3
• 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 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• HRKBSOYXUISAKH-UHFFFAOYSA-N ethyl 3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate Chemical compound CCOC(=O)N1C(C2)CCC1CN2C1=NC=NC2=C1C=CN2 HRKBSOYXUISAKH-UHFFFAOYSA-N 0.000 claims description 3
• HAHWJQLMZREYFZ-UHFFFAOYSA-N ethyl n-[3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octane-8-carbothioyl]carbamate Chemical compound CCOC(=O)NC(=S)N1C(C2)CCC1CN2C1=NC=NC2=C1C=CN2 HAHWJQLMZREYFZ-UHFFFAOYSA-N 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
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