NL1030324C2 - Sulfonylbenzimidazoolderivaten. - Google Patents

Info

Publication number

NL1030324C2

NL1030324C2 NL1030324A NL1030324A NL1030324C2 NL 1030324 C2 NL1030324 C2 NL 1030324C2 NL 1030324 A NL1030324 A NL 1030324A NL 1030324 A NL1030324 A NL 1030324A NL 1030324 C2 NL1030324 C2 NL 1030324C2

Authority

NL

Netherlands

Prior art keywords

group

alkyl

substituted

methyl

dimethylpropyl

Prior art date

2004-11-02

Links

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• Global Dossier
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• IYUBCLHILARKQB-UHFFFAOYSA-N 2-sulfonylbenzimidazole Chemical class C1=CC=CC2=NC(=S(=O)=O)N=C21 IYUBCLHILARKQB-UHFFFAOYSA-N 0.000 title description 3
• -1 isopropylsulfonyl Chemical group 0.000 claims description 362
• 150000001875 compounds Chemical class 0.000 claims description 206
• 125000000623 heterocyclic group Chemical group 0.000 claims description 114
• 125000000217 alkyl group Chemical group 0.000 claims description 108
• 125000001424 substituent group Chemical group 0.000 claims description 106
• 125000003277 amino group Chemical group 0.000 claims description 103
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 81
• 201000006417 multiple sclerosis Diseases 0.000 claims description 62
• 125000003118 aryl group Chemical group 0.000 claims description 56
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 56
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 48
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 43
• 229910052757 nitrogen Chemical group 0.000 claims description 40
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
• 125000005843 halogen group Chemical group 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 33
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 32
• 229910052799 carbon Inorganic materials 0.000 claims description 31
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 29
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 25
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 25
• 239000003814 drug Substances 0.000 claims description 15
• 238000011282 treatment Methods 0.000 claims description 15
• 208000002193 Pain Diseases 0.000 claims description 14
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 14
• 201000010099 disease Diseases 0.000 claims description 13
• 230000000694 effects Effects 0.000 claims description 12
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 12
• 102000009135 CB2 Cannabinoid Receptor Human genes 0.000 claims description 10
• 108010073376 CB2 Cannabinoid Receptor Proteins 0.000 claims description 10
• 230000036407 pain Effects 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• 201000006474 Brain Ischemia Diseases 0.000 claims description 6
• 230000001404 mediated effect Effects 0.000 claims description 6
• 206010008120 Cerebral ischaemia Diseases 0.000 claims description 5
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• 230000001684 chronic effect Effects 0.000 claims description 5
• 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 5
• 208000004296 neuralgia Diseases 0.000 claims description 5
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
• ZUCSYLRZUIFQRF-UHFFFAOYSA-N 2-(2,2-dimethylpropyl)-6-ethylsulfonyl-3-(oxan-4-ylmethyl)imidazo[4,5-b]pyridine Chemical compound CC(C)(C)CC1=NC2=CC(S(=O)(=O)CC)=CN=C2N1CC1CCOCC1 ZUCSYLRZUIFQRF-UHFFFAOYSA-N 0.000 claims description 4
• WGIXCJGYRLRVKG-UHFFFAOYSA-N 2-tert-butyl-5-ethylsulfonyl-1-(oxan-2-ylmethyl)benzimidazole Chemical compound CC(C)(C)C1=NC2=CC(S(=O)(=O)CC)=CC=C2N1CC1CCCCO1 WGIXCJGYRLRVKG-UHFFFAOYSA-N 0.000 claims description 4
• QKMYBDCEPKMNCO-UHFFFAOYSA-N 2-tert-butyl-5-ethylsulfonyl-1-(oxan-4-ylmethyl)benzimidazole Chemical compound CC(C)(C)C1=NC2=CC(S(=O)(=O)CC)=CC=C2N1CC1CCOCC1 QKMYBDCEPKMNCO-UHFFFAOYSA-N 0.000 claims description 4
• CYVVQCCAUVKDCB-UHFFFAOYSA-N 2-tert-butyl-6-ethylsulfonyl-3-(oxan-4-ylmethyl)imidazo[4,5-b]pyridine Chemical compound CC(C)(C)C1=NC2=CC(S(=O)(=O)CC)=CN=C2N1CC1CCOCC1 CYVVQCCAUVKDCB-UHFFFAOYSA-N 0.000 claims description 4
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• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
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• CWOCNAQYXGPFLF-UHFFFAOYSA-N 1-[2-tert-butyl-1-(cyclopropylmethyl)benzimidazol-5-yl]sulfonyl-2-methylpropan-2-ol Chemical compound CC(C)(C)C1=NC2=CC(S(=O)(=O)CC(C)(O)C)=CC=C2N1CC1CC1 CWOCNAQYXGPFLF-UHFFFAOYSA-N 0.000 claims description 3
• PVCSVRLFAQMRQJ-UHFFFAOYSA-N 1-[[2-(2,2-dimethylpropyl)-5-ethylsulfonylbenzimidazol-1-yl]methyl]cyclopentan-1-ol Chemical compound CC(C)(C)CC1=NC2=CC(S(=O)(=O)CC)=CC=C2N1CC1(O)CCCC1 PVCSVRLFAQMRQJ-UHFFFAOYSA-N 0.000 claims description 3
• PULUCWGTNASYGC-UHFFFAOYSA-N 2-(2,2-dimethylpropyl)-6-ethylsulfonyl-3-[2-(trifluoromethoxy)ethyl]imidazo[4,5-b]pyridine Chemical compound CCS(=O)(=O)C1=CN=C2N(CCOC(F)(F)F)C(CC(C)(C)C)=NC2=C1 PULUCWGTNASYGC-UHFFFAOYSA-N 0.000 claims description 3
• JDYFPOCQOQRBHH-UHFFFAOYSA-N 2-[2-(2,2-dimethylpropyl)-1-[2-(trifluoromethoxy)ethyl]benzimidazol-5-yl]sulfonyl-2-methylpropan-1-ol Chemical compound OCC(C)(C)S(=O)(=O)C1=CC=C2N(CCOC(F)(F)F)C(CC(C)(C)C)=NC2=C1 JDYFPOCQOQRBHH-UHFFFAOYSA-N 0.000 claims description 3
• XYHCDXYBKBJRPC-UHFFFAOYSA-N 2-[2-tert-butyl-1-(cyclopropylmethyl)benzimidazol-5-yl]sulfonyl-2-methylpropan-1-ol Chemical compound CC(C)(C)C1=NC2=CC(S(=O)(=O)C(C)(C)CO)=CC=C2N1CC1CC1 XYHCDXYBKBJRPC-UHFFFAOYSA-N 0.000 claims description 3
• MOASUYKEWRFBHZ-UHFFFAOYSA-N 2-tert-butyl-3-(oxan-4-ylmethyl)-6-propan-2-ylsulfonylimidazo[4,5-b]pyridine Chemical compound CC(C)(C)C1=NC2=CC(S(=O)(=O)C(C)C)=CN=C2N1CC1CCOCC1 MOASUYKEWRFBHZ-UHFFFAOYSA-N 0.000 claims description 3
• NPMWGQCDTKRAJK-UHFFFAOYSA-N 4-[(2-tert-butyl-5-tert-butylsulfonylbenzimidazol-1-yl)methyl]oxan-4-ol Chemical compound CC(C)(C)C1=NC2=CC(S(=O)(=O)C(C)(C)C)=CC=C2N1CC1(O)CCOCC1 NPMWGQCDTKRAJK-UHFFFAOYSA-N 0.000 claims description 3
• 208000000884 Airway Obstruction Diseases 0.000 claims description 3
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• 208000011231 Crohn disease Diseases 0.000 claims description 3
• 201000004624 Dermatitis Diseases 0.000 claims description 3
• 206010012735 Diarrhoea Diseases 0.000 claims description 3
• 206010018364 Glomerulonephritis Diseases 0.000 claims description 3
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• 206010065390 Inflammatory pain Diseases 0.000 claims description 3
• 208000008930 Low Back Pain Diseases 0.000 claims description 3
• 206010028980 Neoplasm Diseases 0.000 claims description 3
• 208000001132 Osteoporosis Diseases 0.000 claims description 3
• 201000004681 Psoriasis Diseases 0.000 claims description 3
• 208000036284 Rhinitis seasonal Diseases 0.000 claims description 3
• 208000006011 Stroke Diseases 0.000 claims description 3
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
• 206010047115 Vasculitis Diseases 0.000 claims description 3
• 239000013543 active substance Substances 0.000 claims description 3
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• 125000004432 carbon atom Chemical group C* 0.000 claims description 3
• 206010012601 diabetes mellitus Diseases 0.000 claims description 3
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• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
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• 230000002441 reversible effect Effects 0.000 claims description 3
• 208000017022 seasonal allergic rhinitis Diseases 0.000 claims description 3
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 3
• SOWZZBKSIOEFNM-UHFFFAOYSA-N 1-[2-tert-butyl-1-(oxan-4-ylmethyl)benzimidazol-5-yl]sulfonyl-2-methylpropan-2-ol Chemical compound CC(C)(C)C1=NC2=CC(S(=O)(=O)CC(C)(O)C)=CC=C2N1CC1CCOCC1 SOWZZBKSIOEFNM-UHFFFAOYSA-N 0.000 claims description 2
• IJJDNRKMCVLSNA-UHFFFAOYSA-N 1-[[2-tert-butyl-5-(1-hydroxy-2-methylpropan-2-yl)sulfonylbenzimidazol-1-yl]methyl]cyclopentan-1-ol Chemical compound CC(C)(C)C1=NC2=CC(S(=O)(=O)C(C)(C)CO)=CC=C2N1CC1(O)CCCC1 IJJDNRKMCVLSNA-UHFFFAOYSA-N 0.000 claims description 2
• HMNMQJFDPOKAQH-UHFFFAOYSA-N 2-(2,2-dimethylpropyl)-5-ethylsulfonyl-1-(oxan-4-ylmethyl)benzimidazole Chemical compound CC(C)(C)CC1=NC2=CC(S(=O)(=O)CC)=CC=C2N1CC1CCOCC1 HMNMQJFDPOKAQH-UHFFFAOYSA-N 0.000 claims description 2
• QUPQCDRZCLTJIB-UHFFFAOYSA-N 2-(2,2-dimethylpropyl)-5-ethylsulfonyl-1-[2-(trifluoromethoxy)ethyl]benzimidazole Chemical compound CCS(=O)(=O)C1=CC=C2N(CCOC(F)(F)F)C(CC(C)(C)C)=NC2=C1 QUPQCDRZCLTJIB-UHFFFAOYSA-N 0.000 claims description 2
• KBTFBZPPPXFERJ-UHFFFAOYSA-N 2-tert-butyl-1-(cyclopropylmethyl)-5-propan-2-ylsulfonylbenzimidazole Chemical compound CC(C)(C)C1=NC2=CC(S(=O)(=O)C(C)C)=CC=C2N1CC1CC1 KBTFBZPPPXFERJ-UHFFFAOYSA-N 0.000 claims description 2
• MHGOYTPUMGRCGN-UHFFFAOYSA-N 2-tert-butyl-1-(oxan-4-ylmethyl)-5-(propan-2-ylsulfonylmethyl)benzimidazole Chemical compound CC(C)(C)C1=NC2=CC(CS(=O)(=O)C(C)C)=CC=C2N1CC1CCOCC1 MHGOYTPUMGRCGN-UHFFFAOYSA-N 0.000 claims description 2
• RWALICDEUJFFIX-UHFFFAOYSA-N 4-[[2-(2,2-dimethylpropyl)-6-propan-2-ylsulfonylimidazo[4,5-b]pyridin-3-yl]methyl]oxan-4-ol Chemical compound CC(C)(C)CC1=NC2=CC(S(=O)(=O)C(C)C)=CN=C2N1CC1(O)CCOCC1 RWALICDEUJFFIX-UHFFFAOYSA-N 0.000 claims description 2
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• ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Substances CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 2
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• LOTFQFQGPFCYDC-UHFFFAOYSA-N 2-[2-(2,2-dimethylpropyl)-5-propan-2-ylsulfonylbenzimidazol-1-yl]-n,n-dimethylethanamine Chemical compound CC(C)S(=O)(=O)C1=CC=C2N(CCN(C)C)C(CC(C)(C)C)=NC2=C1 LOTFQFQGPFCYDC-UHFFFAOYSA-N 0.000 claims 1
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