NO323146B1 - Benzazolderivater, deres anvendelse som JNK-modulatorer, farmasoytisk sammensetning som inneholder disse og fremgangsmate til fremstilling av derivatene, - Google Patents

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Publication number

NO323146B1

NO323146B1 NO20022997A NO20022997A NO323146B1 NO 323146 B1 NO323146 B1 NO 323146B1 NO 20022997 A NO20022997 A NO 20022997A NO 20022997 A NO20022997 A NO 20022997A NO 323146 B1 NO323146 B1 NO 323146B1

Authority

NO

Norway

Prior art keywords

benzothiazol

acetonitrile

pyrimidin

amino

pyrimidinyl

Prior art date

1999-12-24

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• 238000000034 method Methods 0.000 title claims description 35
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 18
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 96
• -1 trifluoromethylsulfonyl anilino Chemical group 0.000 claims description 71
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 41
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• 108010055717 JNK Mitogen-Activated Protein Kinases Proteins 0.000 claims description 33
• 238000002360 preparation method Methods 0.000 claims description 32
• 238000006243 chemical reaction Methods 0.000 claims description 24
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 23
• 229910052736 halogen Inorganic materials 0.000 claims description 22
• 150000002367 halogens Chemical group 0.000 claims description 22
• 239000001257 hydrogen Substances 0.000 claims description 22
• 230000037361 pathway Effects 0.000 claims description 22
• 101000950669 Homo sapiens Mitogen-activated protein kinase 9 Proteins 0.000 claims description 21
• 102100037809 Mitogen-activated protein kinase 9 Human genes 0.000 claims description 21
• 208000035475 disorder Diseases 0.000 claims description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
• 150000002431 hydrogen Chemical class 0.000 claims description 14
• 230000000694 effects Effects 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 11
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 9
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 230000014509 gene expression Effects 0.000 claims description 6
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
• PKDPUENCROCRCH-UHFFFAOYSA-N 1-piperazin-1-ylethanone Chemical group CC(=O)N1CCNCC1 PKDPUENCROCRCH-UHFFFAOYSA-N 0.000 claims description 5
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
• 208000023275 Autoimmune disease Diseases 0.000 claims description 5
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
• 229940079593 drug Drugs 0.000 claims description 5
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 5
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 125000000369 oxido group Chemical group [*]=O 0.000 claims description 5
• 125000004043 oxo group Chemical group O=* 0.000 claims description 5
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
• QVMKLKBODZHJDK-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-2-(2-chloropyrimidin-4-yl)acetonitrile Chemical compound ClC1=NC=CC(C(C#N)C=2SC3=CC=CC=C3N=2)=N1 QVMKLKBODZHJDK-UHFFFAOYSA-N 0.000 claims description 4
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• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 150000003230 pyrimidines Chemical class 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
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• OLTNDXQXCQVUHV-UHFFFAOYSA-N S1C(=NC2=C1C=CC=C2)C(C#N)C2=NC(=NC=C2)N2CCN(CC2)C.S2C(=NC1=C2C=CC=C1)C(C#N)C1=NC(=NC=C1)N1CCC(CC1)CC1=CC=CC=C1 Chemical compound S1C(=NC2=C1C=CC=C2)C(C#N)C2=NC(=NC=C2)N2CCN(CC2)C.S2C(=NC1=C2C=CC=C1)C(C#N)C1=NC(=NC=C1)N1CCC(CC1)CC1=CC=CC=C1 OLTNDXQXCQVUHV-UHFFFAOYSA-N 0.000 claims description 2
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• BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 claims description 2
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