NO332535B1 - Indazoler, benzotiazoler og benzoisotiazoler, anvendelse derav for fremstilling av et medikament, og farmasoytisk preparat omfattende forbindelsen - Google Patents

Info

Publication number

NO332535B1

NO332535B1 NO20051985A NO20051985A NO332535B1 NO 332535 B1 NO332535 B1 NO 332535B1 NO 20051985 A NO20051985 A NO 20051985A NO 20051985 A NO20051985 A NO 20051985A NO 332535 B1 NO332535 B1 NO 332535B1

Authority

NO

Norway

Prior art keywords

oct

azabicyclo

carboxamide

carbon atoms

indazole

Prior art date

2002-09-25

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• 238000004519 manufacturing process Methods 0.000 title claims description 15
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title abstract description 6
• 150000002473 indoazoles Chemical class 0.000 title abstract description 3
• CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 title description 2
• 239000008194 pharmaceutical composition Substances 0.000 title 1
• 238000011282 treatment Methods 0.000 claims abstract description 36
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• 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims abstract description 32
• 125000004432 carbon atom Chemical group C* 0.000 claims description 141
• -1 2-thiophenyl Chemical group 0.000 claims description 62
• 125000000217 alkyl group Chemical group 0.000 claims description 47
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• 238000002360 preparation method Methods 0.000 claims description 30
• 150000003839 salts Chemical class 0.000 claims description 30
• BAKAGHXBJJLTDB-UHFFFAOYSA-N 1,2-benzothiazole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=NSC2=C1 BAKAGHXBJJLTDB-UHFFFAOYSA-N 0.000 claims description 27
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
• 125000003545 alkoxy group Chemical group 0.000 claims description 24
• 229910052739 hydrogen Inorganic materials 0.000 claims description 24
• 229910052731 fluorine Inorganic materials 0.000 claims description 23
• 229910052794 bromium Inorganic materials 0.000 claims description 22
• 229910052801 chlorine Inorganic materials 0.000 claims description 22
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• SABOFVOVHYJWCO-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-bromo-1,2-benzothiazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NSC2=CC(Br)=CC=C21 SABOFVOVHYJWCO-LBPRGKRZSA-N 0.000 claims description 20
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 19
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• 150000001412 amines Chemical class 0.000 claims description 16
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 16
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 16
• 229940079593 drug Drugs 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
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• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
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• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
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• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
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• 150000002367 halogens Chemical class 0.000 claims description 6
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• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Chemical class OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
• LPDNEYZLRXGBKO-UHFFFAOYSA-N 1,2-thiazole-3-carboxamide Chemical compound NC(=O)C=1C=CSN=1 LPDNEYZLRXGBKO-UHFFFAOYSA-N 0.000 claims description 5
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 5
• 208000006011 Stroke Diseases 0.000 claims description 5
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
• 230000001713 cholinergic effect Effects 0.000 claims description 5
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• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
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• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 4
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• JNRQAYFUWDRETJ-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-cyclopropyl-1h-indazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=C2)=NNC1=CC=C2C1CC1 JNRQAYFUWDRETJ-INIZCTEOSA-N 0.000 claims description 4
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