ZA200210275B - Pyrrolo[2,3-d]pyrimidine compounds as immunosuppressive agents. - Google Patents
Pyrrolo[2,3-d]pyrimidine compounds as immunosuppressive agents. Download PDFInfo
- Publication number
- ZA200210275B ZA200210275B ZA200210275A ZA200210275A ZA200210275B ZA 200210275 B ZA200210275 B ZA 200210275B ZA 200210275 A ZA200210275 A ZA 200210275A ZA 200210275 A ZA200210275 A ZA 200210275A ZA 200210275 B ZA200210275 B ZA 200210275B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- amino
- methyl
- alkoxy
- pyrrolo
- Prior art date
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- 229940125721 immunosuppressive agent Drugs 0.000 title description 3
- 239000003018 immunosuppressive agent Substances 0.000 title description 3
- 150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 170
- 150000001875 compounds Chemical class 0.000 claims description 74
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 56
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- -1 hydroxy, amino Chemical group 0.000 claims description 41
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 30
- 125000003282 alkyl amino group Chemical group 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 27
- 108010019421 Janus Kinase 3 Proteins 0.000 claims description 21
- 102000006500 Janus Kinase 3 Human genes 0.000 claims description 21
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 229910052792 caesium Inorganic materials 0.000 claims description 17
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 17
- 125000004442 acylamino group Chemical group 0.000 claims description 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
- 241000124008 Mammalia Species 0.000 claims description 12
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 12
- 206010012601 diabetes mellitus Diseases 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 208000035475 disorder Diseases 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 9
- 102000001253 Protein Kinase Human genes 0.000 claims description 8
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 8
- 108060006633 protein kinase Proteins 0.000 claims description 8
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- 206010012438 Dermatitis atopic Diseases 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 7
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- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 7
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- 210000000056 organ Anatomy 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 7
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 201000006417 multiple sclerosis Diseases 0.000 claims description 6
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 4
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 4
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 210000000987 immune system Anatomy 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- RHFWLPWDOYJEAL-UHFFFAOYSA-N 1,2-oxazol-3-amine Chemical compound NC=1C=CON=1 RHFWLPWDOYJEAL-UHFFFAOYSA-N 0.000 claims description 2
- BNOWDJRGXLVJHD-UHFFFAOYSA-N 3-methyl-1,2-oxazol-4-amine Chemical compound CC1=NOC=C1N BNOWDJRGXLVJHD-UHFFFAOYSA-N 0.000 claims description 2
- CQMHIXRPQGPCNT-UHFFFAOYSA-N 3-methyl-1,2-thiazol-5-amine Chemical compound CC=1C=C(N)SN=1 CQMHIXRPQGPCNT-UHFFFAOYSA-N 0.000 claims description 2
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 claims description 2
- TXZVMZALSHPMNV-UHFFFAOYSA-N 4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-n-(1,3-thiazol-2-yl)piperidine-1-carboxamide Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)NC1=NC=CS1 TXZVMZALSHPMNV-UHFFFAOYSA-N 0.000 claims description 2
- JHQOCEWOJAFCTJ-UHFFFAOYSA-N 4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidine-1-carboxylic acid Chemical compound CC1CCN(C(O)=O)CC1N(C)C1=NC=NC2=C1C=CN2 JHQOCEWOJAFCTJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910002514 Co–Co Inorganic materials 0.000 claims description 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 2
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 2
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- RDGVREXPTVNIOZ-UHFFFAOYSA-N (3-hydroxypyrrolidin-1-yl)-[4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]methanone Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)N1CCC(O)C1 RDGVREXPTVNIOZ-UHFFFAOYSA-N 0.000 claims 1
- KNRLJPBXCVZFKC-UHFFFAOYSA-N 1-[4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-2-(tetrazol-1-yl)ethanone Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)CN1C=NN=N1 KNRLJPBXCVZFKC-UHFFFAOYSA-N 0.000 claims 1
- HJWUCTNLSFICSW-UHFFFAOYSA-N 2-[2-[[4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidine-1-carbonyl]amino]-1,3-thiazol-4-yl]acetic acid Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)NC1=NC(CC(O)=O)=CS1 HJWUCTNLSFICSW-UHFFFAOYSA-N 0.000 claims 1
- YXPJSLNLGWWFQK-UHFFFAOYSA-N 4-[[4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]methyl]benzenesulfonamide Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1CC1=CC=C(S(N)(=O)=O)C=C1 YXPJSLNLGWWFQK-UHFFFAOYSA-N 0.000 claims 1
- OISQSDKFWKJEBA-UHFFFAOYSA-N 4-amino-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(N)C=C1 OISQSDKFWKJEBA-UHFFFAOYSA-N 0.000 claims 1
- WQXRYEVRJRVDSK-UHFFFAOYSA-N 4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-n-(4-methyl-1,3-thiazol-2-yl)piperidine-1-carboxamide Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)NC1=NC(C)=CS1 WQXRYEVRJRVDSK-UHFFFAOYSA-N 0.000 claims 1
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- NHFAFANWNRBBTO-UHFFFAOYSA-N 5-[2-[4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-2-oxoethyl]-1,3-thiazolidine-2,4-dione Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)CC1SC(=O)NC1=O NHFAFANWNRBBTO-UHFFFAOYSA-N 0.000 claims 1
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- RONMOMUOZGIDET-UHFFFAOYSA-N [4-methyl-3-[methyl(7h-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-pyrrolidin-1-ylmethanone Chemical compound C1C(N(C)C=2C=3C=CNC=3N=CN=2)C(C)CCN1C(=O)N1CCCC1 RONMOMUOZGIDET-UHFFFAOYSA-N 0.000 claims 1
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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| US21428700P | 2000-06-26 | 2000-06-26 |
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| ZA200210275A ZA200210275B (en) | 2000-06-26 | 2002-12-19 | Pyrrolo[2,3-d]pyrimidine compounds as immunosuppressive agents. |
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