HRP20110903T1 - Heteroaril supstituirani pirolo[2,3-b]piridini i pirolo[2,3-b]pirimidini kao inhibitori janus kinaze - Google Patents
Heteroaril supstituirani pirolo[2,3-b]piridini i pirolo[2,3-b]pirimidini kao inhibitori janus kinaze Download PDFInfo
- Publication number
- HRP20110903T1 HRP20110903T1 HR20110903T HRP20110903T HRP20110903T1 HR P20110903 T1 HRP20110903 T1 HR P20110903T1 HR 20110903 T HR20110903 T HR 20110903T HR P20110903 T HRP20110903 T HR P20110903T HR P20110903 T1 HRP20110903 T1 HR P20110903T1
- Authority
- HR
- Croatia
- Prior art keywords
- pyrrolo
- pyrazol
- pyrimidin
- propanonitrile
- phenyl
- Prior art date
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- 125000001072 heteroaryl group Chemical group 0.000 title claims abstract 25
- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical class C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 title 1
- 229940122245 Janus kinase inhibitor Drugs 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 95
- 150000003839 salts Chemical class 0.000 claims abstract 91
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract 28
- 125000003118 aryl group Chemical group 0.000 claims abstract 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 25
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract 23
- 125000005843 halogen group Chemical group 0.000 claims abstract 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 19
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 14
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract 13
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract 13
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims abstract 13
- 125000001424 substituent group Chemical group 0.000 claims abstract 13
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 6
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims abstract 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 201000010099 disease Diseases 0.000 claims 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 16
- 206010028980 Neoplasm Diseases 0.000 claims 11
- 201000011510 cancer Diseases 0.000 claims 10
- 208000014767 Myeloproliferative disease Diseases 0.000 claims 9
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims 9
- 208000027866 inflammatory disease Diseases 0.000 claims 9
- -1 C1-4cyanoalkyl Chemical group 0.000 claims 8
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 claims 7
- 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 5
- 102000042838 JAK family Human genes 0.000 claims 5
- 108091082332 JAK family Proteins 0.000 claims 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 5
- 210000002345 respiratory system Anatomy 0.000 claims 5
- 208000017520 skin disease Diseases 0.000 claims 5
- HFNKQEVNSGCOJV-UHFFFAOYSA-N 3-cyclopentyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1-pyrazolyl]propanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C1CCCC1 HFNKQEVNSGCOJV-UHFFFAOYSA-N 0.000 claims 4
- MKZZWHGNUHUYCM-UHFFFAOYSA-N 3-cyclopropyl-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C1CC1 MKZZWHGNUHUYCM-UHFFFAOYSA-N 0.000 claims 4
- 208000032027 Essential Thrombocythemia Diseases 0.000 claims 4
- 201000011152 Pemphigus Diseases 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 201000001976 pemphigus vulgaris Diseases 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- 101000997835 Homo sapiens Tyrosine-protein kinase JAK1 Proteins 0.000 claims 3
- 102100033438 Tyrosine-protein kinase JAK1 Human genes 0.000 claims 3
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 2
- TVGMVLZIRSLGAH-UHFFFAOYSA-N 3-(3-methylsulfonylphenyl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CS(=O)(=O)C1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 TVGMVLZIRSLGAH-UHFFFAOYSA-N 0.000 claims 2
- QCEZQKJRYJUQDQ-UHFFFAOYSA-N 3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]-n-phenylbenzamide Chemical compound C=1C=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1C(=O)NC1=CC=CC=C1 QCEZQKJRYJUQDQ-UHFFFAOYSA-N 0.000 claims 2
- 101000844245 Homo sapiens Non-receptor tyrosine-protein kinase TYK2 Proteins 0.000 claims 2
- 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 claims 2
- 241000701044 Human gammaherpesvirus 4 Species 0.000 claims 2
- 241000701806 Human papillomavirus Species 0.000 claims 2
- 206010048643 Hypereosinophilic syndrome Diseases 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 206010028561 Myeloid metaplasia Diseases 0.000 claims 2
- 208000009525 Myocarditis Diseases 0.000 claims 2
- 102100032028 Non-receptor tyrosine-protein kinase TYK2 Human genes 0.000 claims 2
- 206010034277 Pemphigoid Diseases 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims 2
- 201000008736 Systemic mastocytosis Diseases 0.000 claims 2
- 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 claims 2
- 208000017733 acquired polycythemia vera Diseases 0.000 claims 2
- 208000000594 bullous pemphigoid Diseases 0.000 claims 2
- 208000010247 contact dermatitis Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 230000000302 ischemic effect Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 206010028537 myelofibrosis Diseases 0.000 claims 2
- 208000037244 polycythemia vera Diseases 0.000 claims 2
- HFNKQEVNSGCOJV-OAHLLOKOSA-N ruxolitinib Chemical compound C1([C@@H](CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)CCCC1 HFNKQEVNSGCOJV-OAHLLOKOSA-N 0.000 claims 2
- 201000000849 skin cancer Diseases 0.000 claims 2
- 230000003612 virological effect Effects 0.000 claims 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- CGAYFEFKISEIQR-UHFFFAOYSA-N 1-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]cyclopropane-1-carbonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C1(C#N)CC1 CGAYFEFKISEIQR-UHFFFAOYSA-N 0.000 claims 1
- GIGYWKFQEDAKGV-UHFFFAOYSA-N 1-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]phenyl]-3-phenylurea Chemical compound C=1C=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1NC(=O)NC1=CC=CC=C1 GIGYWKFQEDAKGV-UHFFFAOYSA-N 0.000 claims 1
- CJVMUHAGCRAOIH-UHFFFAOYSA-N 1-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]phenyl]-3-propan-2-ylurea Chemical compound CC(C)NC(=O)NC1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 CJVMUHAGCRAOIH-UHFFFAOYSA-N 0.000 claims 1
- HKTMUSRKGJOFQT-UHFFFAOYSA-N 1-phenyl-2-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]ethanone Chemical compound C1=C(C=2C=3C=CNC=3N=CC=2)C=NN1CC(=O)C1=CC=CC=C1 HKTMUSRKGJOFQT-UHFFFAOYSA-N 0.000 claims 1
- INGUHLZZQKDACC-UHFFFAOYSA-N 1-phenyl-2-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]propan-1-one Chemical compound C1=C(C=2C=3C=CNC=3N=CC=2)C=NN1C(C)C(=O)C1=CC=CC=C1 INGUHLZZQKDACC-UHFFFAOYSA-N 0.000 claims 1
- GDTGNZSOHXXADB-UHFFFAOYSA-N 1-phenyl-2-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propan-1-ol Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(C)C(O)C1=CC=CC=C1 GDTGNZSOHXXADB-UHFFFAOYSA-N 0.000 claims 1
- NTYBSPKWKAEMKG-UHFFFAOYSA-N 1-phenyl-2-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propan-1-one Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(C)C(=O)C1=CC=CC=C1 NTYBSPKWKAEMKG-UHFFFAOYSA-N 0.000 claims 1
- YZGOMXNLMPSGTB-UHFFFAOYSA-N 2-[1-[4-(1H-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]ethyl]benzonitrile Chemical compound N1C=CC=2C1=NC=CC=2C=1C=NN(C=1)C(C)C1=C(C#N)C=CC=C1 YZGOMXNLMPSGTB-UHFFFAOYSA-N 0.000 claims 1
- BOLDWUBNHGCOKD-UHFFFAOYSA-N 2-[1-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]cyclopentyl]acetonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CC=2)C=NN1C1(CC#N)CCCC1 BOLDWUBNHGCOKD-UHFFFAOYSA-N 0.000 claims 1
- IDFICYBUDIOWHA-UHFFFAOYSA-N 2-[1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]cyclohexyl]acetonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C1(CC#N)CCCCC1 IDFICYBUDIOWHA-UHFFFAOYSA-N 0.000 claims 1
- WLWKNCAZCPIQKN-UHFFFAOYSA-N 2-[1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]cyclopentyl]acetonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C1(CC#N)CCCC1 WLWKNCAZCPIQKN-UHFFFAOYSA-N 0.000 claims 1
- DZOWVAFBINXFOB-UHFFFAOYSA-N 2-[1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]cyclopropyl]acetonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C1(CC#N)CC1 DZOWVAFBINXFOB-UHFFFAOYSA-N 0.000 claims 1
- XMDCTOCUQQUDPE-UHFFFAOYSA-N 2-[2-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]-5-(trifluoromethyl)phenyl]acetonitrile Chemical compound N#CCC1=CC(C(F)(F)F)=CC=C1N1N=CC(C=2C=3C=CNC=3N=CC=2)=C1 XMDCTOCUQQUDPE-UHFFFAOYSA-N 0.000 claims 1
- PAWUPHYEOOFEER-UHFFFAOYSA-N 2-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]pyridine-4-carbonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C1=CC(C#N)=CC=N1 PAWUPHYEOOFEER-UHFFFAOYSA-N 0.000 claims 1
- WBTHKLYGCKGFPM-UHFFFAOYSA-N 2-[3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]cyclohexyl]acetonitrile Chemical compound C1C(CC#N)CCCC1N1N=CC(C=2C=3C=CNC=3N=CN=2)=C1 WBTHKLYGCKGFPM-UHFFFAOYSA-N 0.000 claims 1
- BIPPXMZRIQZSKE-UHFFFAOYSA-N 2-[3-chloro-2-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]-5-(trifluoromethyl)phenyl]acetonitrile Chemical compound N#CCC1=CC(C(F)(F)F)=CC(Cl)=C1N1N=CC(C=2C=3C=CNC=3N=CC=2)=C1 BIPPXMZRIQZSKE-UHFFFAOYSA-N 0.000 claims 1
- VYIIVQPPRDOYNI-UHFFFAOYSA-N 2-[3-methyl-4-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]phenyl]acetonitrile Chemical compound CC1=CC(CC#N)=CC=C1N1N=CC(C=2C=3C=CNC=3N=CC=2)=C1 VYIIVQPPRDOYNI-UHFFFAOYSA-N 0.000 claims 1
- KHVBCXARHGPTLW-UHFFFAOYSA-N 2-[3-methyl-4-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]phenyl]acetonitrile Chemical compound CC1=CC(CC#N)=CC=C1N1N=CC(C=2C=3C=CNC=3N=CN=2)=C1 KHVBCXARHGPTLW-UHFFFAOYSA-N 0.000 claims 1
- PSWCXILVFVGISQ-UHFFFAOYSA-N 2-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]-3-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=CC(C#N)=C1N1N=CC(C=2C=3C=CNC=3N=CC=2)=C1 PSWCXILVFVGISQ-UHFFFAOYSA-N 0.000 claims 1
- YKKSCJLAOCFSQC-UHFFFAOYSA-N 2-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]-5-(trifluoromethyl)benzonitrile Chemical compound N#CC1=CC(C(F)(F)F)=CC=C1N1N=CC(C=2C=3C=CNC=3N=CC=2)=C1 YKKSCJLAOCFSQC-UHFFFAOYSA-N 0.000 claims 1
- UXKVRHSAYBHZJH-UHFFFAOYSA-N 2-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]benzonitrile Chemical compound N#CC1=CC=CC=C1N1N=CC(C=2C=3C=CNC=3N=CC=2)=C1 UXKVRHSAYBHZJH-UHFFFAOYSA-N 0.000 claims 1
- JYLQHLUANOQCSK-UHFFFAOYSA-N 2-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]cyclohexan-1-ol Chemical compound OC1CCCCC1N1N=CC(C=2C=3C=CNC=3N=CC=2)=C1 JYLQHLUANOQCSK-UHFFFAOYSA-N 0.000 claims 1
- QAUAPRNFAWLMAD-UHFFFAOYSA-N 2-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]cyclohexane-1-carbonitrile Chemical compound N#CC1CCCCC1N1N=CC(C=2C=3C=CNC=3N=CC=2)=C1 QAUAPRNFAWLMAD-UHFFFAOYSA-N 0.000 claims 1
- IZANPVOIMADAJP-UHFFFAOYSA-N 2-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]-n-[3-(trifluoromethyl)phenyl]propanamide Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 IZANPVOIMADAJP-UHFFFAOYSA-N 0.000 claims 1
- YJZQNPDRMXNAQI-UHFFFAOYSA-N 2-[4-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]cyclohexyl]acetonitrile Chemical compound C1CC(CC#N)CCC1N1N=CC(C=2C=3C=CNC=3N=CN=2)=C1 YJZQNPDRMXNAQI-UHFFFAOYSA-N 0.000 claims 1
- BORJGIRWWXWVED-UHFFFAOYSA-N 2-[4-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]methyl]phenyl]benzonitrile Chemical compound N#CC1=CC=CC=C1C(C=C1)=CC=C1CN1N=CC(C=2C=3C=CNC=3N=CC=2)=C1 BORJGIRWWXWVED-UHFFFAOYSA-N 0.000 claims 1
- VQUZGUQADNFJDS-UHFFFAOYSA-N 2-[5-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]-2-(trifluoromethyl)phenyl]acetonitrile Chemical compound C1=C(CC#N)C(C(F)(F)F)=CC=C1N1N=CC(C=2C=3C=CNC=3N=CC=2)=C1 VQUZGUQADNFJDS-UHFFFAOYSA-N 0.000 claims 1
- VLJQJXSQIHYYFI-UHFFFAOYSA-N 2-[[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]methyl]benzonitrile Chemical compound N#CC1=CC=CC=C1CN1N=CC(C=2C=3C=CNC=3N=CC=2)=C1 VLJQJXSQIHYYFI-UHFFFAOYSA-N 0.000 claims 1
- GQWKHZGBVWSNHU-UHFFFAOYSA-N 2-chloro-3-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]benzonitrile Chemical compound ClC1=C(C#N)C=CC=C1N1N=CC(C=2C=3C=CNC=3N=CC=2)=C1 GQWKHZGBVWSNHU-UHFFFAOYSA-N 0.000 claims 1
- RKZVHZJXXWWDDP-UHFFFAOYSA-N 2-cyano-n-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]phenyl]acetamide Chemical compound N#CCC(=O)NC1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 RKZVHZJXXWWDDP-UHFFFAOYSA-N 0.000 claims 1
- MYDROCLKHWOEDX-UHFFFAOYSA-N 2-fluoro-4-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]benzonitrile Chemical compound C1=C(C#N)C(F)=CC(N2N=CC(=C2)C=2C=3C=CNC=3N=CC=2)=C1 MYDROCLKHWOEDX-UHFFFAOYSA-N 0.000 claims 1
- CWMSUJYHYZKQCN-UHFFFAOYSA-N 2-phenyl-n-[3-[[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]methyl]phenyl]acetamide Chemical compound C=1C=CC(CN2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1NC(=O)CC1=CC=CC=C1 CWMSUJYHYZKQCN-UHFFFAOYSA-N 0.000 claims 1
- ZVRQJPRMMAJUMZ-UHFFFAOYSA-N 3-(1-benzofuran-2-yl)-3-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C=1C2=CC=CC=C2OC=1C(CC#N)N(N=C1)C=C1C1=CC=NC2=C1C=CN2 ZVRQJPRMMAJUMZ-UHFFFAOYSA-N 0.000 claims 1
- ADCNYQBUDBUNTF-UHFFFAOYSA-N 3-(1-methylcyclopentyl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C1(C)CCCC1 ADCNYQBUDBUNTF-UHFFFAOYSA-N 0.000 claims 1
- TXRBKHPRGSORKD-UHFFFAOYSA-N 3-(1-methylpyrazol-4-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C(CC#N)N1N=CC(C=2C=3C=CNC=3N=CN=2)=C1 TXRBKHPRGSORKD-UHFFFAOYSA-N 0.000 claims 1
- BZZHLZDNLLVCJY-UHFFFAOYSA-N 3-(1-methylsulfonylpyrrolidin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1N(S(=O)(=O)C)CCC1C(CC#N)N1N=CC(C=2C=3C=CNC=3N=CN=2)=C1 BZZHLZDNLLVCJY-UHFFFAOYSA-N 0.000 claims 1
- QIOPTSMJYWGZQX-UHFFFAOYSA-N 3-(2-bromo-1,3-thiazol-5-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound S1C(Br)=NC=C1C(CC#N)N1N=CC(C=2C=3C=CNC=3N=CN=2)=C1 QIOPTSMJYWGZQX-UHFFFAOYSA-N 0.000 claims 1
- BFFDLHXFOKTJJO-UHFFFAOYSA-N 3-(2-bromopyridin-4-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=NC(Br)=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 BFFDLHXFOKTJJO-UHFFFAOYSA-N 0.000 claims 1
- VJOPGWDAQQVHHK-UHFFFAOYSA-N 3-(2-methoxypyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound COC1=NC=CC=C1C(CC#N)N1N=CC(C=2C=3C=CNC=3N=CN=2)=C1 VJOPGWDAQQVHHK-UHFFFAOYSA-N 0.000 claims 1
- KTQQQXLFJWUKOM-UHFFFAOYSA-N 3-(3,5-dibromophenyl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound BrC1=CC(Br)=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 KTQQQXLFJWUKOM-UHFFFAOYSA-N 0.000 claims 1
- MBADRWYPVDLHQC-UHFFFAOYSA-N 3-(3,5-dimethyl-1,2-oxazol-4-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CC1=NOC(C)=C1C(CC#N)N1N=CC(C=2C=3C=CNC=3N=CN=2)=C1 MBADRWYPVDLHQC-UHFFFAOYSA-N 0.000 claims 1
- ZKWJALOZNSEXDT-UHFFFAOYSA-N 3-(3-aminophenyl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound NC1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 ZKWJALOZNSEXDT-UHFFFAOYSA-N 0.000 claims 1
- ZKHIJQOTDVSLGU-UHFFFAOYSA-N 3-(3-benzylsulfanylphenyl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C(C=1)=CC=CC=1SCC1=CC=CC=C1 ZKHIJQOTDVSLGU-UHFFFAOYSA-N 0.000 claims 1
- TVOOWGXRWCNBPV-UHFFFAOYSA-N 3-(3-benzylsulfonylphenyl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C=1C=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1S(=O)(=O)CC1=CC=CC=C1 TVOOWGXRWCNBPV-UHFFFAOYSA-N 0.000 claims 1
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- YBVTVMVSICZEJE-UHFFFAOYSA-N 3-(3-chlorophenyl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound ClC1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 YBVTVMVSICZEJE-UHFFFAOYSA-N 0.000 claims 1
- WCEMDJMNQNQPFW-UHFFFAOYSA-N 3-(3-ethylsulfanylphenyl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CCSC1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 WCEMDJMNQNQPFW-UHFFFAOYSA-N 0.000 claims 1
- ZVSGNVMLGDTCMY-UHFFFAOYSA-N 3-(3-ethylsulfinylphenyl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CCS(=O)C1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 ZVSGNVMLGDTCMY-UHFFFAOYSA-N 0.000 claims 1
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- OKARDSIHOMFMDX-UHFFFAOYSA-N 3-(3-methylimidazol-4-yl)-3-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CN1C=NC=C1C(CC#N)N1N=CC(C=2C=3C=CNC=3N=CC=2)=C1 OKARDSIHOMFMDX-UHFFFAOYSA-N 0.000 claims 1
- CBKOEBGYVBPPLI-UHFFFAOYSA-N 3-(3-morpholin-4-ylsulfonylphenyl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C=1C=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1S(=O)(=O)N1CCOCC1 CBKOEBGYVBPPLI-UHFFFAOYSA-N 0.000 claims 1
- CETUSXLETHLLDA-UHFFFAOYSA-N 3-(3-nitrophenyl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound [O-][N+](=O)C1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 CETUSXLETHLLDA-UHFFFAOYSA-N 0.000 claims 1
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- GMBBHAHHJHZWHJ-UHFFFAOYSA-N 3-(3-phenylmethoxyphenyl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C(C=1)=CC=CC=1OCC1=CC=CC=C1 GMBBHAHHJHZWHJ-UHFFFAOYSA-N 0.000 claims 1
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- LDVFGVGSGXCINC-UHFFFAOYSA-N 3-(4-methylsulfinylphenyl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=CC(S(=O)C)=CC=C1C(CC#N)N1N=CC(C=2C=3C=CNC=3N=CN=2)=C1 LDVFGVGSGXCINC-UHFFFAOYSA-N 0.000 claims 1
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- INARHFWDLBEPIB-UHFFFAOYSA-N 3-(5-bromo-2-methoxyphenyl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound COC1=CC=C(Br)C=C1C(CC#N)N1N=CC(C=2C=3C=CNC=3N=CN=2)=C1 INARHFWDLBEPIB-UHFFFAOYSA-N 0.000 claims 1
- OWZQRLUHNBYDBD-UHFFFAOYSA-N 3-(5-bromopyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound BrC1=CN=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 OWZQRLUHNBYDBD-UHFFFAOYSA-N 0.000 claims 1
- QIUUNPJERHCTRI-UHFFFAOYSA-N 3-(5-cyclohexylsulfanylpyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C(C=1)=CN=CC=1SC1CCCCC1 QIUUNPJERHCTRI-UHFFFAOYSA-N 0.000 claims 1
- GWFVWTNKERDISB-UHFFFAOYSA-N 3-(5-cyclohexylsulfinylpyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C=1N=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1S(=O)C1CCCCC1 GWFVWTNKERDISB-UHFFFAOYSA-N 0.000 claims 1
- YOOBQEXFWQQOPL-UHFFFAOYSA-N 3-(5-cyclohexylsulfonylpyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C=1N=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1S(=O)(=O)C1CCCCC1 YOOBQEXFWQQOPL-UHFFFAOYSA-N 0.000 claims 1
- LWJWGUUTNLAKQG-UHFFFAOYSA-N 3-(5-ethylsulfanylpyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CCSC1=CN=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 LWJWGUUTNLAKQG-UHFFFAOYSA-N 0.000 claims 1
- JXLJWUBYEHEJRB-UHFFFAOYSA-N 3-(5-ethylsulfinylpyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CCS(=O)C1=CN=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 JXLJWUBYEHEJRB-UHFFFAOYSA-N 0.000 claims 1
- UIQXHRAQESDSNP-UHFFFAOYSA-N 3-(5-ethylsulfonylpyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CCS(=O)(=O)C1=CN=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 UIQXHRAQESDSNP-UHFFFAOYSA-N 0.000 claims 1
- HAMDNSCESBAUIU-UHFFFAOYSA-N 3-(5-ethynylpyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C#CC1=CN=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 HAMDNSCESBAUIU-UHFFFAOYSA-N 0.000 claims 1
- ABPKTQVYTSFZQN-UHFFFAOYSA-N 3-(5-formylthiophen-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound S1C(C=O)=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 ABPKTQVYTSFZQN-UHFFFAOYSA-N 0.000 claims 1
- ARTUSOXONCFJSQ-UHFFFAOYSA-N 3-(5-methoxypyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound COC1=CN=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 ARTUSOXONCFJSQ-UHFFFAOYSA-N 0.000 claims 1
- TZNUFUUVSLCYTD-UHFFFAOYSA-N 3-(5-morpholin-4-ylpyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C(C=1)=CN=CC=1N1CCOCC1 TZNUFUUVSLCYTD-UHFFFAOYSA-N 0.000 claims 1
- CWPDWRNLICNHPU-UHFFFAOYSA-N 3-(5-phenylpyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C(C=1)=CN=CC=1C1=CC=CC=C1 CWPDWRNLICNHPU-UHFFFAOYSA-N 0.000 claims 1
- GGYPBLHKXGXDIP-UHFFFAOYSA-N 3-(5-phenylsulfanylpyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C(C=1)=CN=CC=1SC1=CC=CC=C1 GGYPBLHKXGXDIP-UHFFFAOYSA-N 0.000 claims 1
- KTXHYLGUVWAFRU-UHFFFAOYSA-N 3-(5-propan-2-ylsulfanylpyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CC(C)SC1=CN=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 KTXHYLGUVWAFRU-UHFFFAOYSA-N 0.000 claims 1
- XEVUCQWBQWHHBF-UHFFFAOYSA-N 3-(5-propan-2-ylsulfinylpyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CC(C)S(=O)C1=CN=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 XEVUCQWBQWHHBF-UHFFFAOYSA-N 0.000 claims 1
- FAVPKMFQHQYNSB-UHFFFAOYSA-N 3-(5-propan-2-ylsulfonylpyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CC(C)S(=O)(=O)C1=CN=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 FAVPKMFQHQYNSB-UHFFFAOYSA-N 0.000 claims 1
- CLLLIYAKXYKLSF-UHFFFAOYSA-N 3-(5-pyridin-3-ylpyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C(C=1)=CN=CC=1C1=CC=CN=C1 CLLLIYAKXYKLSF-UHFFFAOYSA-N 0.000 claims 1
- KGXATMGGZZNBMA-UHFFFAOYSA-N 3-(5-pyrimidin-5-ylpyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C(C=1)=CN=CC=1C1=CN=CN=C1 KGXATMGGZZNBMA-UHFFFAOYSA-N 0.000 claims 1
- WBJRCQRCLKJHOM-UHFFFAOYSA-N 3-(6-bromopyridin-2-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound BrC1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=N1 WBJRCQRCLKJHOM-UHFFFAOYSA-N 0.000 claims 1
- RWQABNUWBXVZBE-UHFFFAOYSA-N 3-(6-chloropyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=NC(Cl)=CC=C1C(CC#N)N1N=CC(C=2C=3C=CNC=3N=CN=2)=C1 RWQABNUWBXVZBE-UHFFFAOYSA-N 0.000 claims 1
- NNDMVWHOMAYHCB-UHFFFAOYSA-N 3-(6-methoxypyridin-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=NC(OC)=CC=C1C(CC#N)N1N=CC(C=2C=3C=CNC=3N=CN=2)=C1 NNDMVWHOMAYHCB-UHFFFAOYSA-N 0.000 claims 1
- HMDWMUZBJSLHCU-UHFFFAOYSA-N 3-(furan-3-yl)-3-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CC=2)C=NN1C(CC#N)C=1C=COC=1 HMDWMUZBJSLHCU-UHFFFAOYSA-N 0.000 claims 1
- XFYCGSYZXBNSBF-UHFFFAOYSA-N 3-(furan-3-yl)-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C=1C=COC=1 XFYCGSYZXBNSBF-UHFFFAOYSA-N 0.000 claims 1
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- LSMKUUVNRFCGEA-UHFFFAOYSA-N 3-[1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]butyl]benzonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CCC)C1=CC=CC(C#N)=C1 LSMKUUVNRFCGEA-UHFFFAOYSA-N 0.000 claims 1
- ZFAXWTITSSKZDD-UHFFFAOYSA-N 3-[1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]benzonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(C)C1=CC=CC(C#N)=C1 ZFAXWTITSSKZDD-UHFFFAOYSA-N 0.000 claims 1
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- KJSGVEYMDDCOBV-UHFFFAOYSA-N 3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]-n-phenylbenzenesulfonamide Chemical compound C=1C=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1S(=O)(=O)NC1=CC=CC=C1 KJSGVEYMDDCOBV-UHFFFAOYSA-N 0.000 claims 1
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- NSGDMTBTXTVZHW-UHFFFAOYSA-N 3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]benzonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C1=CC=CC(C#N)=C1 NSGDMTBTXTVZHW-UHFFFAOYSA-N 0.000 claims 1
- DNEQCGDNZFTTAJ-UHFFFAOYSA-N 3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]cyclopentane-1-carbonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C1CCC(C#N)C1 DNEQCGDNZFTTAJ-UHFFFAOYSA-N 0.000 claims 1
- QHSMILYAMJWNGM-UHFFFAOYSA-N 3-[3-(1-phenylethylsulfonyl)phenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C=1C=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1S(=O)(=O)C(C)C1=CC=CC=C1 QHSMILYAMJWNGM-UHFFFAOYSA-N 0.000 claims 1
- RPNXFYKFEMLUBK-UHFFFAOYSA-N 3-[3-(1h-pyrazol-4-yl)phenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C(C=1)=CC=CC=1C=1C=NNC=1 RPNXFYKFEMLUBK-UHFFFAOYSA-N 0.000 claims 1
- PPFUCRICNHNATE-UHFFFAOYSA-N 3-[3-(2,6-dimethylmorpholin-4-yl)sulfonylphenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1C(C)OC(C)CN1S(=O)(=O)C1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 PPFUCRICNHNATE-UHFFFAOYSA-N 0.000 claims 1
- HUNKABQMOYQPJN-UHFFFAOYSA-N 3-[3-(2-methylpropylsulfonyl)phenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CC(C)CS(=O)(=O)C1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 HUNKABQMOYQPJN-UHFFFAOYSA-N 0.000 claims 1
- YJLPMITWAXUVTR-UHFFFAOYSA-N 3-[3-(2-phenylethylsulfonyl)phenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C=1C=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1S(=O)(=O)CCC1=CC=CC=C1 YJLPMITWAXUVTR-UHFFFAOYSA-N 0.000 claims 1
- PWBIZOCHRWGZRT-UHFFFAOYSA-N 3-[3-(3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-ylsulfonyl)phenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1CC2CCCCC2CN1S(=O)(=O)C(C=1)=CC=CC=1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 PWBIZOCHRWGZRT-UHFFFAOYSA-N 0.000 claims 1
- OHQQFUHNXRCIOC-UHFFFAOYSA-N 3-[3-(3,4-dihydro-1h-isoquinolin-2-ylsulfonyl)phenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1CC2=CC=CC=C2CN1S(=O)(=O)C(C=1)=CC=CC=1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 OHQQFUHNXRCIOC-UHFFFAOYSA-N 0.000 claims 1
- CRCIGEXBCQQFNX-UHFFFAOYSA-N 3-[3-(4-ethylpiperazin-1-yl)sulfonylphenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1CN(CC)CCN1S(=O)(=O)C1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 CRCIGEXBCQQFNX-UHFFFAOYSA-N 0.000 claims 1
- GWJYOFPTLJITLB-UHFFFAOYSA-N 3-[3-(4-hydroxypiperidin-1-yl)sulfonylphenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1CC(O)CCN1S(=O)(=O)C1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 GWJYOFPTLJITLB-UHFFFAOYSA-N 0.000 claims 1
- UYNKGROTZHOOHG-UHFFFAOYSA-N 3-[3-(4-methylpiperazin-1-yl)sulfonylphenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 UYNKGROTZHOOHG-UHFFFAOYSA-N 0.000 claims 1
- GYKNHLCPEPNDLQ-UHFFFAOYSA-N 3-[3-(4-oxopiperidin-1-yl)sulfonylphenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1CC(=O)CCN1S(=O)(=O)C1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 GYKNHLCPEPNDLQ-UHFFFAOYSA-N 0.000 claims 1
- XGQUSDPRLSCVEZ-UHFFFAOYSA-N 3-[3-(cyanomethoxy)phenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound N#CCOC1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 XGQUSDPRLSCVEZ-UHFFFAOYSA-N 0.000 claims 1
- HQNZCVLBJIKVTE-UHFFFAOYSA-N 3-[3-(cyclohexylmethylsulfonyl)phenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C=1C=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1S(=O)(=O)CC1CCCCC1 HQNZCVLBJIKVTE-UHFFFAOYSA-N 0.000 claims 1
- LCMVFFJEWIRSFV-UHFFFAOYSA-N 3-[3-(cyclopropylmethylsulfonyl)phenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1S(=O)(=O)CC1CC1 LCMVFFJEWIRSFV-UHFFFAOYSA-N 0.000 claims 1
- KFMMWDYHFNAZOQ-UHFFFAOYSA-N 3-[3-(furan-3-ylmethylsulfonyl)phenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C=1C=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1S(=O)(=O)CC=1C=COC=1 KFMMWDYHFNAZOQ-UHFFFAOYSA-N 0.000 claims 1
- NXRSOXHKCMTJCK-UHFFFAOYSA-N 3-[3-(hydroxymethyl)cyclopentyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1C(CO)CCC1C(CC#N)N1N=CC(C=2C=3C=CNC=3N=CN=2)=C1 NXRSOXHKCMTJCK-UHFFFAOYSA-N 0.000 claims 1
- GSWJUWXFLAFQGO-UHFFFAOYSA-N 3-[3-(morpholine-4-carbonyl)phenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C=1C=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1C(=O)N1CCOCC1 GSWJUWXFLAFQGO-UHFFFAOYSA-N 0.000 claims 1
- DBBFIVASUVLZRF-UHFFFAOYSA-N 3-[3-(naphthalen-2-ylmethylsulfonyl)phenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C=1C=C2C=CC=CC2=CC=1CS(=O)(=O)C(C=1)=CC=CC=1C(CC#N)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 DBBFIVASUVLZRF-UHFFFAOYSA-N 0.000 claims 1
- QIQGWSBEXVIJSF-UHFFFAOYSA-N 3-[3-(oxan-4-ylmethylsulfonyl)phenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C=1C=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1S(=O)(=O)CC1CCOCC1 QIQGWSBEXVIJSF-UHFFFAOYSA-N 0.000 claims 1
- NUSSHOZXQNCGGW-UHFFFAOYSA-N 3-[3-(pyridin-4-ylmethylsulfonyl)phenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C=1C=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1S(=O)(=O)CC1=CC=NC=C1 NUSSHOZXQNCGGW-UHFFFAOYSA-N 0.000 claims 1
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- RNHGIBLHNAYYDJ-UHFFFAOYSA-N 3-[4,4-difluoro-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]but-3-enyl]benzonitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC=C(F)F)C1=CC=CC(C#N)=C1 RNHGIBLHNAYYDJ-UHFFFAOYSA-N 0.000 claims 1
- OGPVINHNJYCGAP-UHFFFAOYSA-N 3-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]-3-(1,3-thiazol-5-yl)propanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CC=2)C=NN1C(CC#N)C1=CN=CS1 OGPVINHNJYCGAP-UHFFFAOYSA-N 0.000 claims 1
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- MDMRCXQIINSRGZ-UHFFFAOYSA-N 3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]-3-[5-(trifluoromethyl)pyridin-3-yl]propanenitrile Chemical compound FC(F)(F)C1=CN=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 MDMRCXQIINSRGZ-UHFFFAOYSA-N 0.000 claims 1
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- HPFNKZJTZQFOEN-UHFFFAOYSA-N 3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]-3-thiophen-3-ylpropanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C=1C=CSC=1 HPFNKZJTZQFOEN-UHFFFAOYSA-N 0.000 claims 1
- KJAFOBQBTYIBSM-UHFFFAOYSA-N 3-[4-(cyanomethoxy)phenyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=CC(OCC#N)=CC=C1C(CC#N)N1N=CC(C=2C=3C=CNC=3N=CN=2)=C1 KJAFOBQBTYIBSM-UHFFFAOYSA-N 0.000 claims 1
- RSTJBADBYDTUPD-UHFFFAOYSA-N 3-[5-(1-methylpyrazol-4-yl)pyridin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CN=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 RSTJBADBYDTUPD-UHFFFAOYSA-N 0.000 claims 1
- VYVHOEXPBGOCDZ-UHFFFAOYSA-N 3-[5-(benzenesulfinyl)pyridin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C=1N=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1S(=O)C1=CC=CC=C1 VYVHOEXPBGOCDZ-UHFFFAOYSA-N 0.000 claims 1
- IBZKCYJQNLWBIM-UHFFFAOYSA-N 3-[5-(benzenesulfonyl)pyridin-3-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C=1N=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1S(=O)(=O)C1=CC=CC=C1 IBZKCYJQNLWBIM-UHFFFAOYSA-N 0.000 claims 1
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- CAGSCFQUKPDLOU-UHFFFAOYSA-N 3-[6-(dimethylamino)pyridin-2-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound CN(C)C1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=N1 CAGSCFQUKPDLOU-UHFFFAOYSA-N 0.000 claims 1
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- LHEKCWTVUADBFE-UHFFFAOYSA-N 3-[[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]methyl]-n-[3-(trifluoromethyl)phenyl]benzamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)C=2C=C(CN3N=CC(=C3)C=3C=4C=CNC=4N=CN=3)C=CC=2)=C1 LHEKCWTVUADBFE-UHFFFAOYSA-N 0.000 claims 1
- VRYSVXJBUYKTLO-UHFFFAOYSA-N 3-[[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]methyl]benzonitrile Chemical compound N#CC1=CC=CC(CN2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 VRYSVXJBUYKTLO-UHFFFAOYSA-N 0.000 claims 1
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- NZJRQYKNACJTEU-UHFFFAOYSA-N 3-chloro-2-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]benzonitrile Chemical compound ClC1=CC=CC(C#N)=C1N1N=CC(C=2C=3C=CNC=3N=CC=2)=C1 NZJRQYKNACJTEU-UHFFFAOYSA-N 0.000 claims 1
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- AKUNHDMTESOUJE-UHFFFAOYSA-N 3-methyl-5-[2-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propyl]-1,2,4-oxadiazole Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(C)CC1=NC(C)=NO1 AKUNHDMTESOUJE-UHFFFAOYSA-N 0.000 claims 1
- FSWCHUZTZVAVHQ-UHFFFAOYSA-N 3-pyridin-2-yl-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C1=CC=CC=N1 FSWCHUZTZVAVHQ-UHFFFAOYSA-N 0.000 claims 1
- UYFXFMAEIPPFAG-UHFFFAOYSA-N 3-pyridin-3-yl-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C1=CC=CN=C1 UYFXFMAEIPPFAG-UHFFFAOYSA-N 0.000 claims 1
- IPRAABXWTRGWDG-UHFFFAOYSA-N 3-pyridin-4-yl-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C1=CC=NC=C1 IPRAABXWTRGWDG-UHFFFAOYSA-N 0.000 claims 1
- WJOVXYZBOIIIIM-UHFFFAOYSA-N 3-pyrimidin-5-yl-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC#N)C1=CN=CN=C1 WJOVXYZBOIIIIM-UHFFFAOYSA-N 0.000 claims 1
- IGOCJDKGMYDZSD-UHFFFAOYSA-N 4-(1-benzylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=C(C=2C=3C=CNC=3N=CC=2)C=NN1CC1=CC=CC=C1 IGOCJDKGMYDZSD-UHFFFAOYSA-N 0.000 claims 1
- RWJKKNBOVOMPSI-UHFFFAOYSA-N 4-(1-cyclohex-2-en-1-ylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1CCC=CC1N1N=CC(C=2C=3C=CNC=3N=CC=2)=C1 RWJKKNBOVOMPSI-UHFFFAOYSA-N 0.000 claims 1
- AVEMYBWNWUNQFS-UHFFFAOYSA-N 4-(1-cyclohexylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1CCCCC1N1N=CC(C=2C=3C=CNC=3N=CC=2)=C1 AVEMYBWNWUNQFS-UHFFFAOYSA-N 0.000 claims 1
- QOUXMGUQHNIMDL-UHFFFAOYSA-N 4-(1-phenylpyrazol-4-yl)-1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1C(=C1)C=NN1C1=CC=CC=C1 QOUXMGUQHNIMDL-UHFFFAOYSA-N 0.000 claims 1
- UVWPYXOOEMDENN-UHFFFAOYSA-N 4-(cyanomethoxy)-2-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]benzonitrile Chemical compound N#CCOC1=CC=C(C#N)C(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 UVWPYXOOEMDENN-UHFFFAOYSA-N 0.000 claims 1
- XPKQBAHJYSCQJF-UHFFFAOYSA-N 4-(cyanomethoxy)-3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]benzonitrile Chemical compound N#CCOC1=CC=C(C#N)C=C1C(CC#N)N1N=CC(C=2C=3C=CNC=3N=CN=2)=C1 XPKQBAHJYSCQJF-UHFFFAOYSA-N 0.000 claims 1
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- GLABEBGUPZQZDP-UHFFFAOYSA-N n-(4-chlorophenyl)-3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]benzamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 GLABEBGUPZQZDP-UHFFFAOYSA-N 0.000 claims 1
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- VXYKYNPNDLPFCJ-UHFFFAOYSA-N n-(4-cyanophenyl)-3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]benzamide Chemical compound C=1C=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1C(=O)NC1=CC=C(C#N)C=C1 VXYKYNPNDLPFCJ-UHFFFAOYSA-N 0.000 claims 1
- UOOWWUZHELMFCT-UHFFFAOYSA-N n-(4-phenoxyphenyl)-2-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]butanamide Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC)C(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 UOOWWUZHELMFCT-UHFFFAOYSA-N 0.000 claims 1
- CGCMMJJSVVDARV-UHFFFAOYSA-N n-(4-phenylphenyl)-2-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]butanamide Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC)C(=O)NC(C=C1)=CC=C1C1=CC=CC=C1 CGCMMJJSVVDARV-UHFFFAOYSA-N 0.000 claims 1
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- DVXQVBJUZKRJOD-UHFFFAOYSA-N n-[(4-phenylphenyl)methyl]-2-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]butanamide Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC)C(=O)NCC(C=C1)=CC=C1C1=CC=CC=C1 DVXQVBJUZKRJOD-UHFFFAOYSA-N 0.000 claims 1
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- OIAFXBTXMLGRMP-UHFFFAOYSA-N n-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(C=CC=2)C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 OIAFXBTXMLGRMP-UHFFFAOYSA-N 0.000 claims 1
- LNISPCZDVIRXJX-UHFFFAOYSA-N n-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]phenyl]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)NC1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 LNISPCZDVIRXJX-UHFFFAOYSA-N 0.000 claims 1
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- JJCGUCVQOQCCIC-UHFFFAOYSA-N n-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]phenyl]naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(NC=3C=C(C=CC=3)C(CC#N)N3N=CC(=C3)C=3C=4C=CNC=4N=CN=3)=O)=CC=CC2=C1 JJCGUCVQOQCCIC-UHFFFAOYSA-N 0.000 claims 1
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- CYWKMSDOEMFKBF-UHFFFAOYSA-N n-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]phenyl]pyridine-3-carboxamide Chemical compound C=1C=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1NC(=O)C1=CC=CN=C1 CYWKMSDOEMFKBF-UHFFFAOYSA-N 0.000 claims 1
- PPNQGMKAYPUULI-UHFFFAOYSA-N n-[3-[[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]methyl]phenyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NC=2C=C(CN3N=CC(=C3)C=3C=4C=CNC=4N=CN=3)C=CC=2)=C1 PPNQGMKAYPUULI-UHFFFAOYSA-N 0.000 claims 1
- VEVYJHGTEFGURU-UHFFFAOYSA-N n-[3-[[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]methyl]phenyl]benzenesulfonamide Chemical compound C=1C=CC(CN2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1NS(=O)(=O)C1=CC=CC=C1 VEVYJHGTEFGURU-UHFFFAOYSA-N 0.000 claims 1
- WZDLSGKJTAHQME-UHFFFAOYSA-N n-[3-[[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]methyl]phenyl]naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(NC=3C=C(CN4N=CC(=C4)C=4C=5C=CNC=5N=CN=4)C=CC=3)=O)=CC=CC2=C1 WZDLSGKJTAHQME-UHFFFAOYSA-N 0.000 claims 1
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- BTFQYUJPLYJQKL-UHFFFAOYSA-N n-benzyl-2-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanamide Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(C)C(=O)NCC1=CC=CC=C1 BTFQYUJPLYJQKL-UHFFFAOYSA-N 0.000 claims 1
- ACBCLABDMKFTGU-UHFFFAOYSA-N n-benzyl-3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]-n-methylbenzenesulfonamide Chemical compound C=1C=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1S(=O)(=O)N(C)CC1=CC=CC=C1 ACBCLABDMKFTGU-UHFFFAOYSA-N 0.000 claims 1
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- IDZMFWNJETYMNA-UHFFFAOYSA-N n-benzyl-3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]benzenesulfonamide Chemical compound C=1C=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=CC=1S(=O)(=O)NCC1=CC=CC=C1 IDZMFWNJETYMNA-UHFFFAOYSA-N 0.000 claims 1
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- RYSXARZCHCLMKW-UHFFFAOYSA-N n-naphthalen-1-yl-2-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]butanamide Chemical compound C=1C=CC2=CC=CC=C2C=1NC(=O)C(CC)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 RYSXARZCHCLMKW-UHFFFAOYSA-N 0.000 claims 1
- ZNYWOCGTXLSGKS-UHFFFAOYSA-N n-naphthalen-1-yl-2-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanamide Chemical compound C=1C=CC2=CC=CC=C2C=1NC(=O)C(C)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 ZNYWOCGTXLSGKS-UHFFFAOYSA-N 0.000 claims 1
- BGQICWXNEYJWLQ-UHFFFAOYSA-N n-naphthalen-1-yl-3-[[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]methyl]benzamide Chemical compound C=1C=CC2=CC=CC=C2C=1NC(=O)C(C=1)=CC=CC=1CN(N=C1)C=C1C1=NC=NC2=C1C=CN2 BGQICWXNEYJWLQ-UHFFFAOYSA-N 0.000 claims 1
- XHBHMNUFTISSLS-UHFFFAOYSA-N n-naphthalen-2-yl-2-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]butanamide Chemical compound C=1C=C2C=CC=CC2=CC=1NC(=O)C(CC)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 XHBHMNUFTISSLS-UHFFFAOYSA-N 0.000 claims 1
- WQPPOEOMPCDPLF-UHFFFAOYSA-N n-naphthalen-2-yl-2-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanamide Chemical compound C=1C=C2C=CC=CC2=CC=1NC(=O)C(C)N(N=C1)C=C1C1=NC=NC2=C1C=CN2 WQPPOEOMPCDPLF-UHFFFAOYSA-N 0.000 claims 1
- RZVXRPBQQOZSHP-UHFFFAOYSA-N n-naphthalen-2-yl-3-[[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]methyl]benzamide Chemical compound C=1C=C2C=CC=CC2=CC=1NC(=O)C(C=1)=CC=CC=1CN(N=C1)C=C1C1=NC=NC2=C1C=CN2 RZVXRPBQQOZSHP-UHFFFAOYSA-N 0.000 claims 1
- DQOFAAURSQOBNF-UHFFFAOYSA-N n-phenyl-2-[4-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrazol-1-yl]propanamide Chemical compound C1=C(C=2C=3C=CNC=3N=CC=2)C=NN1C(C)C(=O)NC1=CC=CC=C1 DQOFAAURSQOBNF-UHFFFAOYSA-N 0.000 claims 1
- IPZNHIZMYLXIHS-UHFFFAOYSA-N n-phenyl-2-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]butanamide Chemical compound C1=C(C=2C=3C=CNC=3N=CN=2)C=NN1C(CC)C(=O)NC1=CC=CC=C1 IPZNHIZMYLXIHS-UHFFFAOYSA-N 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 208000025638 primary cutaneous T-cell non-Hodgkin lymphoma Diseases 0.000 claims 1
- SRMKLVJAONASJU-UHFFFAOYSA-N propan-2-yl n-[3-[2-cyano-1-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]ethyl]phenyl]carbamate Chemical compound CC(C)OC(=O)NC1=CC=CC(C(CC#N)N2N=CC(=C2)C=2C=3C=CNC=3N=CN=2)=C1 SRMKLVJAONASJU-UHFFFAOYSA-N 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 206010037844 rash Diseases 0.000 claims 1
- 230000010410 reperfusion Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 claims 1
- 210000003491 skin Anatomy 0.000 claims 1
- 230000036556 skin irritation Effects 0.000 claims 1
- 231100000475 skin irritation Toxicity 0.000 claims 1
- 231100000046 skin rash Toxicity 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
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PCT/US2006/047369 WO2007070514A1 (en) | 2005-12-13 | 2006-12-12 | Heteroaryl substituted pyrrolo[2,3-b]pyridines and pyrrolo[2,3-b]pyrimidines as janus kinase inhibitors |
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HRP20150837TT HRP20150837T2 (hr) | 2005-12-13 | 2015-08-06 | Heteroaril supstituirani pirolo[2,3-b]piridini i pirolo[2,3-b]pirimidini kao inhibitori janus kinaze |
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HRP20170090TT HRP20170090T1 (hr) | 2005-12-13 | 2017-01-19 | Heteroaril supstituirani pirolo[2,3-b]piridini i pirolo[2,3-b]pirimidini kao inhibitori janus kinaze |
HRP20170162TT HRP20170162T1 (hr) | 2005-12-13 | 2017-02-01 | HETEROARIL SUPSTITUIRANI PIROLO[2,3-b]PIRIDINI I PIROLO[2,3-b]PIRIMIDINI KAO INHIBITORI JANUS KINAZE |
HRP20170200TT HRP20170200T1 (hr) | 2005-12-13 | 2017-02-07 | HETEROARIL SUPSTITUIRANI PIROLO[2,3-b]PIRIDINI I PIROLO[2,3-b]PIRIMIDINI KAO INHIBITORI JANUS KINAZE |
HRP20181912TT HRP20181912T1 (hr) | 2005-12-13 | 2018-11-16 | Derivati pirolo[2,3-d]pirimidina kao inhibitori janus kinaze |
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HRP20160112TT HRP20160112T1 (hr) | 2005-12-13 | 2016-02-02 | HETEROARIL SUPSTITUIRANI PIROLO[2,3-b]PIRIDINI I PIROLO[2,3-b]PIRIMIDINI KAO INHIBITORI JANUS KINAZE |
HRP20170090TT HRP20170090T1 (hr) | 2005-12-13 | 2017-01-19 | Heteroaril supstituirani pirolo[2,3-b]piridini i pirolo[2,3-b]pirimidini kao inhibitori janus kinaze |
HRP20170162TT HRP20170162T1 (hr) | 2005-12-13 | 2017-02-01 | HETEROARIL SUPSTITUIRANI PIROLO[2,3-b]PIRIDINI I PIROLO[2,3-b]PIRIMIDINI KAO INHIBITORI JANUS KINAZE |
HRP20170200TT HRP20170200T1 (hr) | 2005-12-13 | 2017-02-07 | HETEROARIL SUPSTITUIRANI PIROLO[2,3-b]PIRIDINI I PIROLO[2,3-b]PIRIMIDINI KAO INHIBITORI JANUS KINAZE |
HRP20181912TT HRP20181912T1 (hr) | 2005-12-13 | 2018-11-16 | Derivati pirolo[2,3-d]pirimidina kao inhibitori janus kinaze |
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