CA2776028C - Pyrrolo[2,3-d]pyrimidine compounds - Google Patents

Info

Publication number

CA2776028C

CA2776028C CA2776028A CA2776028A CA2776028C CA 2776028 C CA2776028 C CA 2776028C CA 2776028 A CA2776028 A CA 2776028A CA 2776028 A CA2776028 A CA 2776028A CA 2776028 C CA2776028 C CA 2776028C

Authority

CA

Canada

Prior art keywords

methyl

pyrrolo

pyrimidin

trans

cyclohexyl

Prior art date

2009-10-15

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

Links

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• CIPO
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• 150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 title abstract description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 263
• 108010024121 Janus Kinases Proteins 0.000 claims abstract description 58
• 102000015617 Janus Kinases Human genes 0.000 claims abstract description 58
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
• -1 cyano, phenyl Chemical group 0.000 claims description 245
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 190
• 229910052739 hydrogen Inorganic materials 0.000 claims description 188
• 239000001257 hydrogen Substances 0.000 claims description 188
• 150000003839 salts Chemical class 0.000 claims description 122
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 113
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 109
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 99
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 94
• 125000001424 substituent group Chemical group 0.000 claims description 90
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 87
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 77
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 70
• 125000003118 aryl group Chemical group 0.000 claims description 66
• 125000000623 heterocyclic group Chemical group 0.000 claims description 54
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 53
• 125000005843 halogen group Chemical group 0.000 claims description 52
• 238000011282 treatment Methods 0.000 claims description 49
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
• 125000004076 pyridyl group Chemical group 0.000 claims description 41
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 41
• 125000001153 fluoro group Chemical group F* 0.000 claims description 39
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 35
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
• 230000001404 mediated effect Effects 0.000 claims description 28
• 125000003545 alkoxy group Chemical group 0.000 claims description 25
• 125000004043 oxo group Chemical group O=* 0.000 claims description 23
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 21
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 20
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
• 125000004193 piperazinyl group Chemical group 0.000 claims description 19
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 18
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
• 208000006673 asthma Diseases 0.000 claims description 15
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
• 206010052779 Transplant rejections Diseases 0.000 claims description 13
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 13
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 13
• 230000005764 inhibitory process Effects 0.000 claims description 13
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 13
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 13
• 201000006417 multiple sclerosis Diseases 0.000 claims description 13
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 13
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 13
• JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims description 12
• 206010028980 Neoplasm Diseases 0.000 claims description 11
• 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 11
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
• 208000023275 Autoimmune disease Diseases 0.000 claims description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
• 208000035475 disorder Diseases 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• 206010012601 diabetes mellitus Diseases 0.000 claims description 9
• 201000010099 disease Diseases 0.000 claims description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 210000000056 organ Anatomy 0.000 claims description 9
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 9
• 239000003937 drug carrier Substances 0.000 claims description 8
• 206010020751 Hypersensitivity Diseases 0.000 claims description 7
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
• 230000001363 autoimmune Effects 0.000 claims description 7
• 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 7
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 7
• IZXWMVPZODQBRB-UHFFFAOYSA-N piperidine-3,4-diol Chemical compound OC1CCNCC1O IZXWMVPZODQBRB-UHFFFAOYSA-N 0.000 claims description 7
• 125000003386 piperidinyl group Chemical group 0.000 claims description 7
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
• 208000006011 Stroke Diseases 0.000 claims description 6
• 230000007815 allergy Effects 0.000 claims description 6
• 125000002393 azetidinyl group Chemical group 0.000 claims description 6
• 201000011510 cancer Diseases 0.000 claims description 6
• 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
• 208000032839 leukemia Diseases 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 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 description 6
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 208000024827 Alzheimer disease Diseases 0.000 claims description 5
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
• 208000003556 Dry Eye Syndromes Diseases 0.000 claims description 5
• 206010013774 Dry eye Diseases 0.000 claims description 5
• 206010025323 Lymphomas Diseases 0.000 claims description 5
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 5
• 201000004681 Psoriasis Diseases 0.000 claims description 5
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 5
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
• 206010003246 arthritis Diseases 0.000 claims description 5
• 230000001684 chronic effect Effects 0.000 claims description 5
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• YWEMBZPSYGFVOH-UHFFFAOYSA-N 3-methyl-4-(phenylmethoxycarbonylamino)benzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1NC(=O)OCC1=CC=CC=C1 YWEMBZPSYGFVOH-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 4
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
• 208000011231 Crohn disease Diseases 0.000 claims description 4
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
• 208000034578 Multiple myelomas Diseases 0.000 claims description 4
• 208000033759 Prolymphocytic T-Cell Leukemia Diseases 0.000 claims description 4
• 206010060862 Prostate cancer Diseases 0.000 claims description 4
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
• 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 4
• 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 4
• 206010040047 Sepsis Diseases 0.000 claims description 4
• 208000026651 T-cell prolymphocytic leukemia Diseases 0.000 claims description 4
• 210000001744 T-lymphocyte Anatomy 0.000 claims description 4
• 206010046851 Uveitis Diseases 0.000 claims description 4
• 230000001154 acute effect Effects 0.000 claims description 4
• 208000026935 allergic disease Diseases 0.000 claims description 4
• 210000001185 bone marrow Anatomy 0.000 claims description 4
• 206010006451 bronchitis Diseases 0.000 claims description 4
• 208000027866 inflammatory disease Diseases 0.000 claims description 4
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 4
• 201000008482 osteoarthritis Diseases 0.000 claims description 4
• 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 description 3
• 208000024799 Thyroid disease Diseases 0.000 claims description 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
• 206010025135 lupus erythematosus Diseases 0.000 claims description 3
• 125000006626 methoxycarbonylamino group Chemical group 0.000 claims description 3
• 230000003612 virological effect Effects 0.000 claims description 3
• 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 2
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 42
• FNYKNWAPYCCIQE-VNHLFDKOSA-N C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CCC(C)(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)(O)C1 FNYKNWAPYCCIQE-VNHLFDKOSA-N 0.000 claims 4
• 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 4
• 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 4
• RRWIERVKMPBTBE-HPFXQQBRSA-N (3r)-1-[[(1s,3r,4s)-3-methyl-4-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl]methylsulfonyl]piperidin-3-ol Chemical compound C([C@@H]1C[C@H]([C@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)C)S(=O)(=O)N1CCC[C@@H](O)C1 RRWIERVKMPBTBE-HPFXQQBRSA-N 0.000 claims 2
• RRWIERVKMPBTBE-CVYDXHPNSA-N (3s)-1-[[(1s,3r,4s)-3-methyl-4-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl]methylsulfonyl]piperidin-3-ol Chemical compound C([C@@H]1C[C@H]([C@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)C)S(=O)(=O)N1CCC[C@H](O)C1 RRWIERVKMPBTBE-CVYDXHPNSA-N 0.000 claims 2
• 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 2
• 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 2
• 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 2
• 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 2
• CTSSTHCUMHCFMF-RRCSTGOVSA-N C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1C[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)N1C[C@@H](O)[C@H](O)C1 CTSSTHCUMHCFMF-RRCSTGOVSA-N 0.000 claims 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• JGCGMHHSWAIIID-IYARVYRRSA-N C1CC(CCOC)(C(N)=O)CCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 Chemical compound C1CC(CCOC)(C(N)=O)CCN1S(=O)(=O)C[C@@H]1CC[C@@H](N(C)C=2C=3C=CNC=3N=CN=2)CC1 JGCGMHHSWAIIID-IYARVYRRSA-N 0.000 claims 2
• 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 2
• 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 2
• 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 2
• SRPNJZWTHJDMHK-CTWPCTMYSA-N [(3r)-1-[[4-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl]methylsulfonyl]piperidin-3-yl] 2,2-dimethylpropanoate Chemical compound N=1C=NC=2NC=CC=2C=1N(C)C(CC1)CCC1CS(=O)(=O)N1CCC[C@@H](OC(=O)C(C)(C)C)C1 SRPNJZWTHJDMHK-CTWPCTMYSA-N 0.000 claims 2
• 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 2
• 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 2
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 2
• SEWNTJFAYCYCGB-UFYCRDLUSA-N C([C@@H]1CCCN1S(=O)(=O)C[C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)N1CCCC1 Chemical compound C([C@@H]1CCCN1S(=O)(=O)C[C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)N1CCCC1 SEWNTJFAYCYCGB-UFYCRDLUSA-N 0.000 claims 1
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• SEVRGDCXHGHYDX-JCNLHEQBSA-N C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N(C1)CC1C1=NC=CC=N1 Chemical compound C([C@H]1CC[C@@H](CC1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N(C1)CC1C1=NC=CC=N1 SEVRGDCXHGHYDX-JCNLHEQBSA-N 0.000 claims 1
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