JP2014501772A5 - - Google Patents
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- JP2014501772A5 JP2014501772A5 JP2013547865A JP2013547865A JP2014501772A5 JP 2014501772 A5 JP2014501772 A5 JP 2014501772A5 JP 2013547865 A JP2013547865 A JP 2013547865A JP 2013547865 A JP2013547865 A JP 2013547865A JP 2014501772 A5 JP2014501772 A5 JP 2014501772A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyrrolo
- diazaspiro
- octane
- pyrimidin
- Prior art date
- 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.)
- Pending
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- -1 cyano, hydroxy Chemical group 0.000 claims 80
- 150000001875 compounds Chemical class 0.000 claims 38
- 125000000623 heterocyclic group Chemical group 0.000 claims 28
- 125000004404 heteroalkyl group Chemical group 0.000 claims 22
- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 239000001257 hydrogen Substances 0.000 claims 22
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 16
- 150000002431 hydrogen Chemical class 0.000 claims 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- 125000004043 oxo group Chemical group O=* 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 12
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 208000023275 Autoimmune disease Diseases 0.000 claims 4
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 4
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 4
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 3
- 201000004624 Dermatitis Diseases 0.000 claims 3
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 claims 3
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 3
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 3
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 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 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 3
- 208000015181 infectious disease Diseases 0.000 claims 3
- 230000002458 infectious effect Effects 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 2
- 206010012438 Dermatitis atopic Diseases 0.000 claims 2
- 102000042838 JAK family Human genes 0.000 claims 2
- 108091082332 JAK family Proteins 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010040799 Skin atrophy Diseases 0.000 claims 2
- 241000534944 Thia Species 0.000 claims 2
- 201000008937 atopic dermatitis Diseases 0.000 claims 2
- 208000010668 atopic eczema Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000030533 eye disease Diseases 0.000 claims 2
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 206010023332 keratitis Diseases 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- QWOKKHXWFDAJCZ-UHFFFAOYSA-N octane-1-sulfonamide Chemical compound CCCCCCCCS(N)(=O)=O QWOKKHXWFDAJCZ-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 230000009759 skin aging Effects 0.000 claims 2
- 208000017520 skin disease Diseases 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 1
- 125000006532 (C3-C5) alkyl group Chemical group 0.000 claims 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- 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 1
- PIDLOAOWCYMMHN-UHFFFAOYSA-N 1-[[7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]sulfonyl]piperidine-3-carbonitrile Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)N1CCCC(C#N)C1 PIDLOAOWCYMMHN-UHFFFAOYSA-N 0.000 claims 1
- LJNYZRGQGRKNRP-UHFFFAOYSA-N 1-[[7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octan-4-yl]sulfonyl]piperidine-4-carbonitrile Chemical compound C1CN(C=2C=3C=CNC=3N=CN=2)CC2(CC2)N1S(=O)(=O)N1CCC(C#N)CC1 LJNYZRGQGRKNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 208000002874 Acne Vulgaris Diseases 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000026872 Addison Disease Diseases 0.000 claims 1
- 201000004384 Alopecia Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010002198 Anaphylactic reaction Diseases 0.000 claims 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 1
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 201000005569 Gout Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 208000003084 Graves Ophthalmopathy Diseases 0.000 claims 1
- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims 1
- 101000844245 Homo sapiens Non-receptor tyrosine-protein kinase TYK2 Proteins 0.000 claims 1
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 claims 1
- 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- NMMOWASTGBPHTO-UHFFFAOYSA-N N-(2,2-diphenylethyl)-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)NCC(C=1C=CC=CC=1)C1=CC=CC=C1 NMMOWASTGBPHTO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- KSGABDOLZMZUQQ-UHFFFAOYSA-N N-(3-cyanopropyl)-N-(2-hydroxyethyl)-7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound N#CCCCN(CCO)S(=O)(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 KSGABDOLZMZUQQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- GZZHZUCELYUDTF-UHFFFAOYSA-N N-(3-cyanopropyl)-N-methyl-7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound N#CCCCN(C)S(=O)(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 GZZHZUCELYUDTF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- AFOKHZQYRYCSGZ-UHFFFAOYSA-N N-(cyanomethyl)-N-[(1,1-dioxothian-4-yl)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(CC#N)CC1CCS(=O)(=O)CC1 AFOKHZQYRYCSGZ-UHFFFAOYSA-N 0.000 claims 1
- RHLWUNNBYOGZPF-UHFFFAOYSA-N N-[(1,1-dioxothian-4-yl)methyl]-N-(2-hydroxyethyl)-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(CCO)CC1CCS(=O)(=O)CC1 RHLWUNNBYOGZPF-UHFFFAOYSA-N 0.000 claims 1
- GTSKKXYSCFTTPE-UHFFFAOYSA-N N-[(1,1-dioxothiolan-3-yl)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)NCC1CCS(=O)(=O)C1 GTSKKXYSCFTTPE-UHFFFAOYSA-N 0.000 claims 1
- RJVRCXVEEOIPDV-UHFFFAOYSA-N N-[(1,1-dioxothiolan-3-yl)methyl]-N-(2-hydroxyethyl)-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(CCO)CC1CCS(=O)(=O)C1 RJVRCXVEEOIPDV-UHFFFAOYSA-N 0.000 claims 1
- CBAWBLHQVSTOSY-UHFFFAOYSA-N N-[(1,1-dioxothiolan-3-yl)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)CC1CCS(=O)(=O)C1 CBAWBLHQVSTOSY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- VCFLUFTWBWEFFW-UHFFFAOYSA-N N-[(4-fluorophenyl)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=C(F)C=C1 VCFLUFTWBWEFFW-UHFFFAOYSA-N 0.000 claims 1
- BKMPNDMVBLLYPY-UHFFFAOYSA-N N-[2-(4-fluorophenyl)ethyl]-N-(2-phenylethyl)-7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1=CC(F)=CC=C1CCN(S(=O)(=O)N1C2(CC2)CN(CC1)C=1C=2C=CNC=2N=CN=1)CCC1=CC=CC=C1 BKMPNDMVBLLYPY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- CFXKIKUOOYKOGW-KRWDZBQOSA-N N-[[(2S)-1-(3-cyanopropylsulfonyl)-4,4-difluoropyrrolidin-2-yl]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)C[C@@H]1CC(F)(F)CN1S(=O)(=O)CCCC#N CFXKIKUOOYKOGW-KRWDZBQOSA-N 0.000 claims 1
- ULRRKTYCONSYMA-HNNXBMFYSA-N N-[[(2S)-4,4-difluoro-1-(3-hydroxypropanoyl)pyrrolidin-2-yl]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)C[C@@H]1CC(F)(F)CN1C(=O)CCO ULRRKTYCONSYMA-HNNXBMFYSA-N 0.000 claims 1
- HDMGZGMCZKCJEP-AWEZNQCLSA-N N-[[(2S)-4,4-difluoro-1-formylpyrrolidin-2-yl]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)C[C@@H]1CC(F)(F)CN1C=O HDMGZGMCZKCJEP-AWEZNQCLSA-N 0.000 claims 1
- BBKNDPZTJPDRKJ-UHFFFAOYSA-N N-[[1-(3-cyanopropanoyl)piperidin-4-yl]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)CC1CCN(C(=O)CCC#N)CC1 BBKNDPZTJPDRKJ-UHFFFAOYSA-N 0.000 claims 1
- VUELUIFCCDJRAJ-UHFFFAOYSA-N N-[[2-(2,2-difluoroethyl)-1,5-dihydropyrazol-5-yl]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)CC1NN(CC(F)F)C=C1 VUELUIFCCDJRAJ-UHFFFAOYSA-N 0.000 claims 1
- AXIKLLWMQWXJLL-UHFFFAOYSA-N N-[[2-(difluoromethyl)-1,5-dihydropyrazol-5-yl]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)CC1NN(C(F)F)C=C1 AXIKLLWMQWXJLL-UHFFFAOYSA-N 0.000 claims 1
- IHSSPJIVZWYYOV-UHFFFAOYSA-N N-methyl-7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-N-[[4-(trifluoromethyl)phenyl]methyl]-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=C(C(F)(F)F)C=C1 IHSSPJIVZWYYOV-UHFFFAOYSA-N 0.000 claims 1
- 201000011152 Pemphigus Diseases 0.000 claims 1
- 208000031845 Pernicious anaemia Diseases 0.000 claims 1
- 206010036105 Polyneuropathy Diseases 0.000 claims 1
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 1
- 208000003251 Pruritus Diseases 0.000 claims 1
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- GKNYDHLHNZPDEH-UHFFFAOYSA-N n-[2-(3-cyanophenoxy)ethyl]-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)CCOC1=CC=CC(C#N)=C1 GKNYDHLHNZPDEH-UHFFFAOYSA-N 0.000 claims 1
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- MYUXLKVLFFVJOE-UHFFFAOYSA-N n-[2-(4-chlorophenoxy)ethyl]-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)CCOC1=CC=C(Cl)C=C1 MYUXLKVLFFVJOE-UHFFFAOYSA-N 0.000 claims 1
- XWOHIVREEIWKFO-UHFFFAOYSA-N n-[2-(4-cyanophenoxy)ethyl]-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)CCOC1=CC=C(C#N)C=C1 XWOHIVREEIWKFO-UHFFFAOYSA-N 0.000 claims 1
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- MVOYGCXBJNKIAH-MRXNPFEDSA-N n-[[(2r)-1-(3-hydroxypropanoyl)pyrrolidin-2-yl]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)C[C@H]1CCCN1C(=O)CCO MVOYGCXBJNKIAH-MRXNPFEDSA-N 0.000 claims 1
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- LETIGEUQCHTFEP-HNNXBMFYSA-N n-[[(2s)-1-(2-hydroxyacetyl)pyrrolidin-2-yl]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)C[C@@H]1CCCN1C(=O)CO LETIGEUQCHTFEP-HNNXBMFYSA-N 0.000 claims 1
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- MVOYGCXBJNKIAH-INIZCTEOSA-N n-[[(2s)-1-(3-hydroxypropanoyl)pyrrolidin-2-yl]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)C[C@@H]1CCCN1C(=O)CCO MVOYGCXBJNKIAH-INIZCTEOSA-N 0.000 claims 1
- AUGZVODVVIWPRS-KRWDZBQOSA-N n-[[(2s)-1-(cyclopropylmethylsulfonyl)-4,4-difluoropyrrolidin-2-yl]methyl]-n-methyl-7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C([C@H]1CN(C)S(=O)(=O)N2C3(CC3)CN(CC2)C=2C=3C=CNC=3N=CN=2)C(F)(F)CN1S(=O)(=O)CC1CC1 AUGZVODVVIWPRS-KRWDZBQOSA-N 0.000 claims 1
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- 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 1
- JMCQWNDAFZDTTQ-UHFFFAOYSA-N n-methyl-n-[(1-methylsulfonylpiperidin-3-yl)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)CC1CCCN(S(C)(=O)=O)C1 JMCQWNDAFZDTTQ-UHFFFAOYSA-N 0.000 claims 1
- JZLQAKGYMDVZCZ-UHFFFAOYSA-N n-methyl-n-[(1-methylsulfonylpiperidin-4-yl)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)CC1CCN(S(C)(=O)=O)CC1 JZLQAKGYMDVZCZ-UHFFFAOYSA-N 0.000 claims 1
- QMXMDZFGOZTFMB-UHFFFAOYSA-N n-methyl-n-[(1-methylsulfonylpyrrolidin-3-yl)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)CC1CCN(S(C)(=O)=O)C1 QMXMDZFGOZTFMB-UHFFFAOYSA-N 0.000 claims 1
- NQQPQVZZTCEQOU-UHFFFAOYSA-N n-methyl-n-[(1-propanoylpyrrolidin-3-yl)methyl]-7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1N(C(=O)CC)CCC1CN(C)S(=O)(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 NQQPQVZZTCEQOU-UHFFFAOYSA-N 0.000 claims 1
- PKBYSESHDMNDES-UHFFFAOYSA-N n-methyl-n-[(1-propylsulfonylpyrrolidin-3-yl)methyl]-7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound C1N(S(=O)(=O)CCC)CCC1CN(C)S(=O)(=O)N1C2(CC2)CN(C=2C=3C=CNC=3N=CN=2)CC1 PKBYSESHDMNDES-UHFFFAOYSA-N 0.000 claims 1
- WUQJAIUIPSLVMN-UHFFFAOYSA-N n-methyl-n-[(3-oxocyclobutyl)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)CC1CC(=O)C1 WUQJAIUIPSLVMN-UHFFFAOYSA-N 0.000 claims 1
- IRCSTPRQTVOZNC-UHFFFAOYSA-N n-methyl-n-[(4-methylidenecyclohexyl)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)CC1CCC(=C)CC1 IRCSTPRQTVOZNC-UHFFFAOYSA-N 0.000 claims 1
- FAFXZDGVCUCCMZ-UHFFFAOYSA-N n-methyl-n-[(4-methylsulfonylphenyl)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=C(S(C)(=O)=O)C=C1 FAFXZDGVCUCCMZ-UHFFFAOYSA-N 0.000 claims 1
- DLQYDROUVYFJPX-OAHLLOKOSA-N n-methyl-n-[[(2r)-1-methylsulfonylpyrrolidin-2-yl]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)C[C@H]1CCCN1S(C)(=O)=O DLQYDROUVYFJPX-OAHLLOKOSA-N 0.000 claims 1
- JCJXXXUMLHAIRS-CYBMUJFWSA-N n-methyl-n-[[(2r)-5-oxopyrrolidin-2-yl]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)C[C@H]1CCC(=O)N1 JCJXXXUMLHAIRS-CYBMUJFWSA-N 0.000 claims 1
- DIVAVHINIHYTBQ-CQSZACIVSA-N n-methyl-n-[[(2r)-pyrrolidin-2-yl]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)C[C@H]1CCCN1 DIVAVHINIHYTBQ-CQSZACIVSA-N 0.000 claims 1
- DLQYDROUVYFJPX-HNNXBMFYSA-N n-methyl-n-[[(2s)-1-methylsulfonylpyrrolidin-2-yl]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)C[C@@H]1CCCN1S(C)(=O)=O DLQYDROUVYFJPX-HNNXBMFYSA-N 0.000 claims 1
- JCJXXXUMLHAIRS-ZDUSSCGKSA-N n-methyl-n-[[(2s)-5-oxopyrrolidin-2-yl]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)C[C@@H]1CCC(=O)N1 JCJXXXUMLHAIRS-ZDUSSCGKSA-N 0.000 claims 1
- DIVAVHINIHYTBQ-AWEZNQCLSA-N n-methyl-n-[[(2s)-pyrrolidin-2-yl]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)C[C@@H]1CCCN1 DIVAVHINIHYTBQ-AWEZNQCLSA-N 0.000 claims 1
- UQPSNJBBYOKOGM-UHFFFAOYSA-N n-methyl-n-phenacyl-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)CC(=O)C1=CC=CC=C1 UQPSNJBBYOKOGM-UHFFFAOYSA-N 0.000 claims 1
- CIGKTCDFFAKRJN-UHFFFAOYSA-N n-methyl-n-phenyl-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)C1=CC=CC=C1 CIGKTCDFFAKRJN-UHFFFAOYSA-N 0.000 claims 1
- RKBWDKYOMREEBB-UHFFFAOYSA-N n-methyl-n-phenylmethoxy-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)OCC1=CC=CC=C1 RKBWDKYOMREEBB-UHFFFAOYSA-N 0.000 claims 1
- RTAKUAFBDVROFX-UHFFFAOYSA-N n-methyl-n-propan-2-yl-7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound CC(C)N(C)S(=O)(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 RTAKUAFBDVROFX-UHFFFAOYSA-N 0.000 claims 1
- XQOVWVQOSYRSQW-UHFFFAOYSA-N n-pentan-2-yl-7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound CCCC(C)NS(=O)(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 XQOVWVQOSYRSQW-UHFFFAOYSA-N 0.000 claims 1
- JJUSREYAJYCMFX-UHFFFAOYSA-N n-phenylmethoxy-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)NOCC1=CC=CC=C1 JJUSREYAJYCMFX-UHFFFAOYSA-N 0.000 claims 1
- OTCDORFSTSKFAZ-UHFFFAOYSA-N n-propan-2-yl-7-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-sulfonamide Chemical compound CC(C)NS(=O)(=O)N1CCN(C=2C=3C=CNC=3N=CN=2)CC11CC1 OTCDORFSTSKFAZ-UHFFFAOYSA-N 0.000 claims 1
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- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 claims 1
- 201000001976 pemphigus vulgaris Diseases 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
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| EP3145512B1 (en) * | 2014-05-19 | 2019-07-17 | Jiangsu Hengrui Medicine Co., Ltd. | Substituted ethynyl heterobicyclic compounds as tyrosine kinase inhibitors |
| CN106661031B (zh) | 2014-06-24 | 2019-07-23 | 大鹏药品工业株式会社 | 吡咯并嘧啶化合物或其盐、含有其的药物组合物及应用 |
| CN110291090A (zh) * | 2017-01-20 | 2019-09-27 | 利奥制药有限公司 | 作为新型jak激酶抑制剂的双环胺 |
| US10799507B2 (en) | 2017-02-03 | 2020-10-13 | Leo Pharma A/S | 5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5-azaspiro[2.5]octane-8-carboxylic acid derivatives as novel JAK kinase inhibitors |
| CN108822048A (zh) * | 2018-07-23 | 2018-11-16 | 上海昌肽生物科技有限公司 | 4-(4-乙基-4,7二氮杂螺环[3,3]辛基)-2-硝基苯胺的合成工艺 |
| CN116730927A (zh) * | 2023-03-21 | 2023-09-12 | 广州佳途科技股份有限公司 | 一种新型高效合成4,7-二氮杂螺[2.5]辛烷盐酸盐的方法 |
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| AU3951899A (en) * | 1998-06-19 | 2000-01-05 | Pfizer Products Inc. | Pyrrolo(2,3-d)pyrimidine compounds |
| PA8474101A1 (es) * | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| OA12118A (en) * | 1999-12-10 | 2006-05-04 | Pfizer Prod Inc | PyrroloÄ2,3-dÜpyrimidine compounds. |
| WO2003022214A2 (en) * | 2001-09-06 | 2003-03-20 | Millennium Pharmaceuticals, Inc. | Piperazine and homopiperazine compounds |
| AU2003284142A1 (en) * | 2002-10-15 | 2004-05-04 | Synta Pharmaceuticals Corp | Aromatic bicyclic heterocyles to modulate 1L-12 production |
| SE0301372D0 (sv) | 2003-05-09 | 2003-05-09 | Astrazeneca Ab | Novel compounds |
| AU2004293026B2 (en) | 2003-11-21 | 2012-01-19 | Array Biopharma Inc. | AKT protein kinase inhibitors |
| CA2545192A1 (en) * | 2003-11-25 | 2005-06-09 | Pfizer Products Inc. | Method of treatment of atherosclerosis |
| RU2006120956A (ru) | 2003-12-17 | 2008-01-27 | Пфайзер Продактс Инк. (Us) | Пирроло{2, 3-d}пиримидиновые соединения для лечения отторжения трансплантата |
| TWI380816B (zh) | 2004-04-13 | 2013-01-01 | Synta Pharmaceuticals Corp | 抑制介白素-１２（ｉｌ-１２）生成之二鹽抑制劑 |
| AR054416A1 (es) * | 2004-12-22 | 2007-06-27 | Incyte Corp | Pirrolo [2,3-b]piridin-4-il-aminas y pirrolo [2,3-b]pirimidin-4-il-aminas como inhibidores de las quinasas janus. composiciones farmaceuticas. |
| US8633205B2 (en) * | 2005-02-03 | 2014-01-21 | Vertex Pharmaceuticals Incorporated | Substituted pyrrolo[2,3-d]pyrimidines as inhibitors of protein kinases |
| US7423043B2 (en) | 2005-02-18 | 2008-09-09 | Lexicon Pharmaceuticals, Inc. | 4-Piperidin-1-yl-7H-pyrrolo[2,3-d]pyrimidine compounds |
| JP2008545660A (ja) * | 2005-05-20 | 2008-12-18 | バーテックス ファーマシューティカルズ インコーポレイテッド | プロテインキナーゼ阻害剤として有用なピロロピリジン化合物 |
| CN102127078A (zh) * | 2005-07-14 | 2011-07-20 | 安斯泰来制药株式会社 | Janus激酶3的杂环类抑制剂 |
| HRP20120786T1 (hr) | 2006-02-02 | 2012-11-30 | Millennium Pharmaceuticals, Inc. | Inhibitori aktivirajuä†eg enzima e1 |
| GB0604944D0 (en) * | 2006-03-11 | 2006-04-19 | Vernalis R&D Ltd | Pyrrolopyrimidine compounds |
| CA2645343A1 (en) | 2006-03-11 | 2007-09-20 | Vernalis (R&D) Limited | Pyrrolopyrimidine derivatives used as hsp90 inhibitors |
| JP2009532475A (ja) | 2006-04-05 | 2009-09-10 | バーテックス ファーマシューティカルズ インコーポレイテッド | ヤヌスキナーゼの阻害剤として有用なデアザプリン |
| AU2008240188A1 (en) * | 2007-04-13 | 2008-10-23 | Supergen, Inc. | Axl kinase inhibitors useful for the treatment of cancer or hyperproliferative disorders |
| ES2557931T3 (es) * | 2007-08-08 | 2016-01-29 | Lexicon Pharmaceuticals, Inc. | (7H-Pirrolo[2,3-d]pirimidin-4-il)-piperazinas como inhibidores de cinasas para el tratamiento de cáncer e inflamación |
| JP5690823B2 (ja) * | 2009-07-08 | 2015-03-25 | レオ ファーマ アクティーゼルスカブ | 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 |
-
2012
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- 2012-01-06 AU AU2012204843A patent/AU2012204843A1/en not_active Abandoned
- 2012-01-06 JP JP2013547865A patent/JP2014501772A/ja active Pending
- 2012-01-06 KR KR1020137020834A patent/KR20140058402A/ko not_active Withdrawn
- 2012-01-06 EP EP12700266.5A patent/EP2661436B1/en not_active Not-in-force
- 2012-01-06 BR BR112013017184A patent/BR112013017184A2/pt not_active IP Right Cessation
- 2012-01-06 US US13/977,408 patent/US9233964B2/en not_active Expired - Fee Related
- 2012-01-06 MX MX2013007792A patent/MX2013007792A/es not_active Application Discontinuation
- 2012-01-06 WO PCT/EP2012/050187 patent/WO2012093169A1/en not_active Ceased
- 2012-01-06 CA CA2823935A patent/CA2823935A1/en not_active Abandoned
- 2012-01-06 RU RU2013136906/04A patent/RU2013136906A/ru not_active Application Discontinuation
- 2012-01-09 TW TW101100842A patent/TW201309703A/zh unknown
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