CA2899888A1 - Pyrrolo[2,3-d]pyrimidine derivatives - Google Patents

Info

Publication number

CA2899888A1

CA2899888A1 CA2899888A CA2899888A CA2899888A1 CA 2899888 A1 CA2899888 A1 CA 2899888A1 CA 2899888 A CA2899888 A CA 2899888A CA 2899888 A CA2899888 A CA 2899888A CA 2899888 A1 CA2899888 A1 CA 2899888A1

Authority

CA

Canada

Prior art keywords

methyl

pyrrolo

cis

pyrimidin

cyclobutyl

Prior art date

2014-08-12

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 title abstract description 7
• 230000009021 linear effect Effects 0.000 claims description 474
• 125000000217 alkyl group Chemical group 0.000 claims description 372
• 150000001875 compounds Chemical class 0.000 claims description 296
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 270
• -1 --OR e Chemical group 0.000 claims description 157
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 156
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 140
• 125000003118 aryl group Chemical group 0.000 claims description 136
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 128
• 125000001072 heteroaryl group Chemical group 0.000 claims description 112
• 125000005843 halogen group Chemical group 0.000 claims description 111
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 83
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 58
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 55
• 150000003839 salts Chemical class 0.000 claims description 54
• 125000003545 alkoxy group Chemical group 0.000 claims description 53
• 125000001424 substituent group Chemical group 0.000 claims description 53
• 229910052739 hydrogen Inorganic materials 0.000 claims description 51
• 239000001257 hydrogen Substances 0.000 claims description 51
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 47
• 229910052805 deuterium Inorganic materials 0.000 claims description 47
• 150000002431 hydrogen Chemical group 0.000 claims description 46
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 43
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 43
• 125000000623 heterocyclic group Chemical group 0.000 claims description 42
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 42
• 229910052757 nitrogen Inorganic materials 0.000 claims description 39
• 125000004429 atom Chemical group 0.000 claims description 35
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 31
• 229910052799 carbon Inorganic materials 0.000 claims description 21
• 125000002950 monocyclic group Chemical group 0.000 claims description 21
• 125000002619 bicyclic group Chemical group 0.000 claims description 20
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 239000001301 oxygen Substances 0.000 claims description 18
• 229920006395 saturated elastomer Polymers 0.000 claims description 18
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
• 125000005842 heteroatom Chemical group 0.000 claims description 17
• 229910052717 sulfur Inorganic materials 0.000 claims description 17
• 239000011593 sulfur Substances 0.000 claims description 17
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
• 125000001188 haloalkyl group Chemical group 0.000 claims description 13
• 229910052702 rhenium Inorganic materials 0.000 claims description 10
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 9
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 8
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
• SVPZJHKVRMRREG-UHFFFAOYSA-N cyclopentanecarbonitrile Chemical compound N#CC1CCCC1 SVPZJHKVRMRREG-UHFFFAOYSA-N 0.000 claims description 7
• GFBLFDSCAKHHGX-UHFFFAOYSA-N cyclobutanecarbonitrile Chemical compound N#CC1CCC1 GFBLFDSCAKHHGX-UHFFFAOYSA-N 0.000 claims description 6
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 5
• 229940116839 Janus kinase 1 inhibitor Drugs 0.000 claims description 4
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 4
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• 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 3
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
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• TUEQXSLLTMWDFV-BETUJISGSA-N FC1(CC(C1)(C)CS(=O)(=O)C[C@H]1C[C@H](C1)N(C=1C2=C(N=CN=1)NC=C2)C)F Chemical compound FC1(CC(C1)(C)CS(=O)(=O)C[C@H]1C[C@H](C1)N(C=1C2=C(N=CN=1)NC=C2)C)F TUEQXSLLTMWDFV-BETUJISGSA-N 0.000 claims description 2
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• IQCLJRQNJINKEK-GASCZTMLSA-N N([C@H]1C[C@H](C1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)C1=CC=CC(C(C)(C)O)=C1 Chemical compound N([C@H]1C[C@H](C1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)C1=CC=CC(C(C)(C)O)=C1 IQCLJRQNJINKEK-GASCZTMLSA-N 0.000 claims description 2
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• UYSGAWMQMRAGJH-RWMBFGLXSA-N N([C@H]1C[C@H](C1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CC[C@@H](C#N)C1 Chemical compound N([C@H]1C[C@H](C1)N(C)C=1C=2C=CNC=2N=CN=1)S(=O)(=O)N1CC[C@@H](C#N)C1 UYSGAWMQMRAGJH-RWMBFGLXSA-N 0.000 claims description 2
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• PBIUUJCEMUAWJJ-UHFFFAOYSA-N azetidine-3-carbonitrile Chemical compound N#CC1CNC1 PBIUUJCEMUAWJJ-UHFFFAOYSA-N 0.000 claims description 2
• 229910052731 fluorine Inorganic materials 0.000 claims description 2
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• AKEUQPIANKYLQS-TXEJJXNPSA-N CC1(COC1)CS(=O)(=O)N[C@@H]1C[C@@H](C1)N(C=1C2=C(N=CN=1)NC=C2)C Chemical compound CC1(COC1)CS(=O)(=O)N[C@@H]1C[C@@H](C1)N(C=1C2=C(N=CN=1)NC=C2)C AKEUQPIANKYLQS-TXEJJXNPSA-N 0.000 claims 2
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• HYMXQESPSIAYCN-UHFFFAOYSA-N cyclobutanesulfonamide Chemical compound NS(=O)(=O)C1CCC1 HYMXQESPSIAYCN-UHFFFAOYSA-N 0.000 claims 2
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