JP2013508266A5 - - Google Patents
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- Publication number
- JP2013508266A5 JP2013508266A5 JP2012533715A JP2012533715A JP2013508266A5 JP 2013508266 A5 JP2013508266 A5 JP 2013508266A5 JP 2012533715 A JP2012533715 A JP 2012533715A JP 2012533715 A JP2012533715 A JP 2012533715A JP 2013508266 A5 JP2013508266 A5 JP 2013508266A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- methyl
- alkyl
- hydrogen
- pyrrolo
- 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.)
- Granted
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- -1 R 24 Chemical compound 0.000 claims 113
- 229910052739 hydrogen Inorganic materials 0.000 claims 89
- 239000001257 hydrogen Substances 0.000 claims 89
- 150000002431 hydrogen Chemical class 0.000 claims 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 39
- 125000001424 substituent group Chemical group 0.000 claims 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 35
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 32
- 150000003839 salts Chemical class 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 23
- 125000000623 heterocyclic group Chemical group 0.000 claims 21
- 125000003118 aryl group Chemical group 0.000 claims 20
- 125000004076 pyridyl group Chemical group 0.000 claims 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims 19
- 125000001153 fluoro group Chemical group F* 0.000 claims 19
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 17
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 14
- 125000005843 halogen group Chemical group 0.000 claims 14
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 11
- 125000004043 oxo group Chemical group O=* 0.000 claims 10
- 125000004193 piperazinyl group Chemical group 0.000 claims 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 9
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims 6
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims 6
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 6
- 102000015617 Janus Kinases Human genes 0.000 claims 5
- 108010024121 Janus Kinases Proteins 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
- 230000001404 mediated effect Effects 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 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 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims 4
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- JHPKJBVRIXKCRE-UHFFFAOYSA-N 2-sulfonylpiperidin-3-ol Chemical compound S(=O)(=O)=C1NCCCC1O JHPKJBVRIXKCRE-UHFFFAOYSA-N 0.000 claims 2
- QMHIFZZTSBMKGF-NXOAAHMSSA-N C1[C@H](CO)[C@@H](C)CN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 Chemical compound C1[C@H](CO)[C@@H](C)CN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 QMHIFZZTSBMKGF-NXOAAHMSSA-N 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 238000010276 construction Methods 0.000 claims 2
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
- DFVBZOPVGGDURA-UYSNPLJNSA-N (3r)-1-[[4-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl]methylsulfonyl]piperidin-3-ol Chemical compound N=1C=NC=2NC=CC=2C=1N(C)C(CC1)CCC1CS(=O)(=O)N1CCC[C@@H](O)C1 DFVBZOPVGGDURA-UYSNPLJNSA-N 0.000 claims 1
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- CNUBKBHAGWYWKC-QAQDUYKDSA-N C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CCC(CO)CC1 Chemical compound C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CCC(CO)CC1 CNUBKBHAGWYWKC-QAQDUYKDSA-N 0.000 claims 1
- QUUQHDKVPKLLLY-SHTZXODSSA-N C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CCC(O)CC1 Chemical compound C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CCC(O)CC1 QUUQHDKVPKLLLY-SHTZXODSSA-N 0.000 claims 1
- JRSQFRIEIAFSCP-XUWMOKQASA-N C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CCCC(CO)C1 Chemical compound C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CCCC(CO)C1 JRSQFRIEIAFSCP-XUWMOKQASA-N 0.000 claims 1
- DFVBZOPVGGDURA-MRJYIUEKSA-N C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CCCC(O)C1 Chemical compound C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CCCC(O)C1 DFVBZOPVGGDURA-MRJYIUEKSA-N 0.000 claims 1
- DFVBZOPVGGDURA-JYJNAYRXSA-N C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CCC[C@H](O)C1 Chemical compound C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CCC[C@H](O)C1 DFVBZOPVGGDURA-JYJNAYRXSA-N 0.000 claims 1
- MALGNVZPLRYZHA-NXNVCVFFSA-N C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CC[C@H](O)[C@H](O)C1 Chemical compound C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CC[C@H](O)[C@H](O)C1 MALGNVZPLRYZHA-NXNVCVFFSA-N 0.000 claims 1
- RCKHTJNDTULILG-RRCSTGOVSA-N C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1C[C@@H](F)[C@H](F)C1 Chemical compound C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1C[C@@H](F)[C@H](F)C1 RCKHTJNDTULILG-RRCSTGOVSA-N 0.000 claims 1
- HLXPYAHSGDXUCD-XUWMOKQASA-N C1C(COC)CCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 Chemical compound C1C(COC)CCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 HLXPYAHSGDXUCD-XUWMOKQASA-N 0.000 claims 1
- VKZZRIHGEAOOMI-BDWYFLKXSA-N C1C(OC)CCCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 Chemical compound C1C(OC)CCCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 VKZZRIHGEAOOMI-BDWYFLKXSA-N 0.000 claims 1
- PLALKTRHBMUZHB-ORXZLVCASA-N C1C(OCC(C)C)CCCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 Chemical compound C1C(OCC(C)C)CCCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 PLALKTRHBMUZHB-ORXZLVCASA-N 0.000 claims 1
- QBEUWGUQNWOOHV-JHJOSGQCSA-N C1C(OCC)CCCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 Chemical compound C1C(OCC)CCCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 QBEUWGUQNWOOHV-JHJOSGQCSA-N 0.000 claims 1
- NCZZXIYJRYNEAO-GAZRBOARSA-N C1C(OCCOC)CCCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 Chemical compound C1C(OCCOC)CCCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 NCZZXIYJRYNEAO-GAZRBOARSA-N 0.000 claims 1
- CZGHFDUUBKBTJH-IYARVYRRSA-N C1CC(COC)CCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 Chemical compound C1CC(COC)CCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 CZGHFDUUBKBTJH-IYARVYRRSA-N 0.000 claims 1
- PKPFNPHDHKBHHB-WKILWMFISA-N C1CC(OC)CCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 Chemical compound C1CC(OC)CCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 PKPFNPHDHKBHHB-WKILWMFISA-N 0.000 claims 1
- ZJVHOOYSNPZCAM-BZUAXINKSA-N C1[C@H](OC)CCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 Chemical compound C1[C@H](OC)CCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 ZJVHOOYSNPZCAM-BZUAXINKSA-N 0.000 claims 1
- POGLJFMJXHZCGT-GUDVDZBRSA-N C1[C@H](OCCOCC)CCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 Chemical compound C1[C@H](OCCOCC)CCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 POGLJFMJXHZCGT-GUDVDZBRSA-N 0.000 claims 1
- CMYJZXSHJXVXHN-BRWVUGGUSA-N COC[C@H]1CCCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 Chemical class COC[C@H]1CCCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 CMYJZXSHJXVXHN-BRWVUGGUSA-N 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims 1
- 206010013774 Dry eye Diseases 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 208000014767 Myeloproliferative disease Diseases 0.000 claims 1
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims 1
- COJRADVRHGSQAO-GUDVDZBRSA-N N1C[C@H](CCC1)CC(C(=O)OS(=O)(=O)C[C@@H]1CC[C@H](CC1)N(C=1C2=C(N=CN1)NC=C2)C)(C)C Chemical compound N1C[C@H](CCC1)CC(C(=O)OS(=O)(=O)C[C@@H]1CC[C@H](CC1)N(C=1C2=C(N=CN1)NC=C2)C)(C)C COJRADVRHGSQAO-GUDVDZBRSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 208000033759 Prolymphocytic T-Cell Leukemia Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000026651 T-cell prolymphocytic leukemia Diseases 0.000 claims 1
- 210000001744 T-lymphocyte Anatomy 0.000 claims 1
- 208000024799 Thyroid disease Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- GYZPAKVHBCQCKK-HVEGKCCWSA-N [(3s)-1-[[3-methyl-4-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl]methylsulfonyl]pyrrolidin-3-yl]methanol Chemical compound C1CC(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CC1CS(=O)(=O)N1CC[C@H](CO)C1 GYZPAKVHBCQCKK-HVEGKCCWSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- 238000010322 bone marrow transplantation Methods 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- UCALNVLMEPQUKV-SOAGJPPSSA-N diethyl [(3r)-1-[[4-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl]methylsulfonyl]piperidin-3-yl] phosphate Chemical compound C1[C@H](OP(=O)(OCC)OCC)CCCN1S(=O)(=O)CC1CCC(N(C)C=2C=3C=CNC=3N=CN=2)CC1 UCALNVLMEPQUKV-SOAGJPPSSA-N 0.000 claims 1
- 150000002009 diols Chemical class 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 125000006626 methoxycarbonylamino group Chemical group 0.000 claims 1
- 125000006405 methylpyridazinyl group Chemical group 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- IZXWMVPZODQBRB-UHFFFAOYSA-N piperidine-3,4-diol Chemical compound OC1CCNCC1O IZXWMVPZODQBRB-UHFFFAOYSA-N 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
- 0 *c1ccccn1 Chemical compound *c1ccccn1 0.000 description 2
- QKAVREGFSUASSA-UHFFFAOYSA-N CCc1ccc(C)nn1 Chemical compound CCc1ccc(C)nn1 QKAVREGFSUASSA-UHFFFAOYSA-N 0.000 description 1
- RILVNLMOTMFTMQ-UHFFFAOYSA-N CCc1ncccn1 Chemical compound CCc1ncccn1 RILVNLMOTMFTMQ-UHFFFAOYSA-N 0.000 description 1
- LYKCEYNKKVKHGA-VVKDPFQVSA-N CN(C1CCC(CCC/C2=C/C=C\C=C/C/C=C2)CC1)c1c(cc[nH]2)c2ncn1 Chemical compound CN(C1CCC(CCC/C2=C/C=C\C=C/C/C=C2)CC1)c1c(cc[nH]2)c2ncn1 LYKCEYNKKVKHGA-VVKDPFQVSA-N 0.000 description 1
- OKUHKHOCCLTDIK-UHFFFAOYSA-N CN(C1CCC(C[Os](C2C=CC=CC=C2)=O)CC1)c1c(cc[nH]2)c2ncn1 Chemical compound CN(C1CCC(C[Os](C2C=CC=CC=C2)=O)CC1)c1c(cc[nH]2)c2ncn1 OKUHKHOCCLTDIK-UHFFFAOYSA-N 0.000 description 1
- DFVBZOPVGGDURA-BZUAXINKSA-N CN([C@H]1CC[C@H](CS(N(CCC2)C[C@@H]2O)(=O)=O)CC1)c1c(cc[nH]2)c2ncn1 Chemical compound CN([C@H]1CC[C@H](CS(N(CCC2)C[C@@H]2O)(=O)=O)CC1)c1c(cc[nH]2)c2ncn1 DFVBZOPVGGDURA-BZUAXINKSA-N 0.000 description 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N Cc1cnc(C)cc1 Chemical compound Cc1cnc(C)cc1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- OISVCGZHLKNMSJ-UHFFFAOYSA-N Cc1nc(C)ccc1 Chemical compound Cc1nc(C)ccc1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 1
- JJYQAQYGUKRIBT-UHFFFAOYSA-N Cc1nc(C/S=[O]/C)n[o]1 Chemical compound Cc1nc(C/S=[O]/C)n[o]1 JJYQAQYGUKRIBT-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25203909P | 2009-10-15 | 2009-10-15 | |
| US61/252,039 | 2009-10-15 | ||
| PCT/IB2010/054447 WO2011045702A1 (en) | 2009-10-15 | 2010-10-01 | Pyrrolo[2,3-d] pyrimidine compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013508266A JP2013508266A (ja) | 2013-03-07 |
| JP2013508266A5 true JP2013508266A5 (enExample) | 2013-10-24 |
| JP5629324B2 JP5629324B2 (ja) | 2014-11-19 |
Family
ID=43413616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012533715A Expired - Fee Related JP5629324B2 (ja) | 2009-10-15 | 2010-10-01 | ピロロ［２，３−ｄ］ピリミジン化合物 |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US8633206B2 (enExample) |
| EP (1) | EP2488524B1 (enExample) |
| JP (1) | JP5629324B2 (enExample) |
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| CN103896946B (zh) * | 2012-12-28 | 2018-04-03 | 浙江导明医药科技有限公司 | 用于预防及治疗多种自身免疫疾病的新化合物 |
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- 2010-10-01 WO PCT/IB2010/054447 patent/WO2011045702A1/en not_active Ceased
- 2010-10-01 AU AU2010308028A patent/AU2010308028A1/en not_active Abandoned
- 2010-10-01 KR KR1020127012417A patent/KR20120083452A/ko not_active Ceased
- 2010-10-01 CN CN2010800461239A patent/CN102574860A/zh active Pending
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- 2010-10-13 US US12/903,554 patent/US8633206B2/en active Active
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