NO300543B1 - 1,7-kondenserte 2-(piperazinoalkyl)-indolderivater og mellomprodukter for deres fremstilling - Google Patents

Info

Publication number

NO300543B1

NO300543B1 NO923282A NO923282A NO300543B1 NO 300543 B1 NO300543 B1 NO 300543B1 NO 923282 A NO923282 A NO 923282A NO 923282 A NO923282 A NO 923282A NO 300543 B1 NO300543 B1 NO 300543B1

Authority

NO

Norway

Prior art keywords

group

substituted

denotes

hydroxy

optionally

Prior art date

1991-08-23

Links

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• 238000002360 preparation method Methods 0.000 title abstract description 30
• 239000000543 intermediate Substances 0.000 title abstract description 8
• 229940054051 antipsychotic indole derivative Drugs 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 241
• -1 C3-C7-alkenyl Chemical group 0.000 claims abstract description 87
• 239000002253 acid Substances 0.000 claims abstract description 76
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 70
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 59
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 55
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 37
• 239000001257 hydrogen Substances 0.000 claims abstract description 37
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 24
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 20
• 150000003839 salts Chemical class 0.000 claims abstract description 15
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 14
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 12
• 239000005864 Sulphur Substances 0.000 claims abstract description 11
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
• 239000001301 oxygen Substances 0.000 claims abstract description 7
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 6
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
• 150000002367 halogens Chemical class 0.000 claims description 45
• 229910052736 halogen Inorganic materials 0.000 claims description 42
• 125000003545 alkoxy group Chemical group 0.000 claims description 39
• 150000002431 hydrogen Chemical class 0.000 claims description 22
• 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 15
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 12
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
• 125000004423 acyloxy group Chemical group 0.000 claims description 9
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• 125000001041 indolyl group Chemical group 0.000 claims description 9
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• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
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• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
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• 229960000583 acetic acid Drugs 0.000 description 26
• 239000002904 solvent Substances 0.000 description 26
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 25
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 24
• 239000002244 precipitate Substances 0.000 description 23
• 238000012360 testing method Methods 0.000 description 23
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• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
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• 125000004356 hydroxy functional group Chemical group O* 0.000 description 20
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• 150000007513 acids Chemical class 0.000 description 19
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• ZFBRKSGGMODDHD-UHFFFAOYSA-N 1-(4-methylpyridin-2-yl)piperazine Chemical compound CC1=CC=NC(N2CCNCC2)=C1 ZFBRKSGGMODDHD-UHFFFAOYSA-N 0.000 description 18
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