FI65427C - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara xanten- eller furankarbonyloxipropanpiperazin-derivat - Google Patents
Foerfarande foer framstaellning av nya terapeutiskt anvaendbara xanten- eller furankarbonyloxipropanpiperazin-derivat Download PDFInfo
- Publication number
- FI65427C FI65427C FI773743A FI773743A FI65427C FI 65427 C FI65427 C FI 65427C FI 773743 A FI773743 A FI 773743A FI 773743 A FI773743 A FI 773743A FI 65427 C FI65427 C FI 65427C
- Authority
- FI
- Finland
- Prior art keywords
- piperazin
- xanthene
- carbonyloxy
- group
- general formula
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 31
- -1 furancarbonyloxypropane piperazine derivatives Chemical class 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims 1
- 125000004953 trihalomethyl group Chemical group 0.000 claims 1
- 125000001680 trimethoxyphenyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000005917 acylation reaction Methods 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LLTVLFHJCBDYPG-UHFFFAOYSA-N 3-(4-prop-2-enylpiperazin-1-yl)propan-1-ol Chemical compound OCCCN1CCN(CC=C)CC1 LLTVLFHJCBDYPG-UHFFFAOYSA-N 0.000 description 3
- NSLZHZKOVGVVEH-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propan-1-ol Chemical compound COC1=CC=CC=C1N1CCN(CCCO)CC1 NSLZHZKOVGVVEH-UHFFFAOYSA-N 0.000 description 3
- KAXYEGYWTMUHLM-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 9h-xanthene-9-carboxylate;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CCCOC(=O)C2C3=CC=CC=C3OC3=CC=CC=C32)CC1 KAXYEGYWTMUHLM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- CIHGCPVAWJMVQE-UHFFFAOYSA-N 3-(4-benzylpiperazin-1-yl)propyl 9h-xanthene-9-carboxylate;dihydrochloride Chemical compound Cl.Cl.C12=CC=CC=C2OC2=CC=CC=C2C1C(=O)OCCCN(CC1)CCN1CC1=CC=CC=C1 CIHGCPVAWJMVQE-UHFFFAOYSA-N 0.000 description 2
- RWHQTSQQOYHQGH-UHFFFAOYSA-N 3-(4-butylpiperazin-1-yl)propyl 9h-xanthene-9-carboxylate Chemical compound C1CN(CCCC)CCN1CCCOC(=O)C1C2=CC=CC=C2OC2=CC=CC=C21 RWHQTSQQOYHQGH-UHFFFAOYSA-N 0.000 description 2
- JREHPVSBEVQWQE-UHFFFAOYSA-N 3-(4-butylpiperazin-1-yl)propyl 9h-xanthene-9-carboxylate;dihydrochloride Chemical compound Cl.Cl.C1CN(CCCC)CCN1CCCOC(=O)C1C2=CC=CC=C2OC2=CC=CC=C21 JREHPVSBEVQWQE-UHFFFAOYSA-N 0.000 description 2
- MRFNRXJKVMMOIT-UHFFFAOYSA-N 3-[4-(2-phenoxyethyl)piperazin-1-yl]propyl 9h-xanthene-9-carboxylate;dihydrochloride Chemical compound Cl.Cl.C12=CC=CC=C2OC2=CC=CC=C2C1C(=O)OCCCN(CC1)CCN1CCOC1=CC=CC=C1 MRFNRXJKVMMOIT-UHFFFAOYSA-N 0.000 description 2
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 2
- JYRSCMLJPXJTLI-UHFFFAOYSA-N 9h-xanthene-9-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)C3=CC=CC=C3OC2=C1 JYRSCMLJPXJTLI-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- HDJLSECJEQSPKW-UHFFFAOYSA-N Methyl 2-Furancarboxylate Chemical compound COC(=O)C1=CC=CO1 HDJLSECJEQSPKW-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000002763 arrhythmic effect Effects 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 2
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 2
- 229960002768 dipyridamole Drugs 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- PZFJRJUFZLBHCJ-UHFFFAOYSA-N ethyl 4-[3-(9h-xanthene-9-carbonyloxy)propyl]piperazine-1-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=O)OCC)CCN1CCCOC(=O)C1C2=CC=CC=C2OC2=CC=CC=C21 PZFJRJUFZLBHCJ-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229960001404 quinidine Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
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- VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 description 1
- ZWAQJGHGPPDZSF-UHFFFAOYSA-N 1-prop-2-enylpiperazine Chemical compound C=CCN1CCNCC1 ZWAQJGHGPPDZSF-UHFFFAOYSA-N 0.000 description 1
- HZNQSWJZTWOTKM-UHFFFAOYSA-N 2,3,4-trimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(OC)=C1OC HZNQSWJZTWOTKM-UHFFFAOYSA-N 0.000 description 1
- 125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 description 1
- PRBASKPGFZYSAI-UHFFFAOYSA-N 3-(4-butylpiperazin-1-yl)propan-1-ol Chemical compound CCCCN1CCN(CCCO)CC1 PRBASKPGFZYSAI-UHFFFAOYSA-N 0.000 description 1
- LVNLMFITHNZGKA-UHFFFAOYSA-N 3-(4-phenylpiperazin-1-yl)propan-1-ol Chemical compound C1CN(CCCO)CCN1C1=CC=CC=C1 LVNLMFITHNZGKA-UHFFFAOYSA-N 0.000 description 1
- JICUPLVXNUQUEY-UHFFFAOYSA-N 3-(4-phenylpiperazin-1-yl)propyl 9h-xanthene-9-carboxylate;dihydrochloride Chemical compound Cl.Cl.C12=CC=CC=C2OC2=CC=CC=C2C1C(=O)OCCCN(CC1)CCN1C1=CC=CC=C1 JICUPLVXNUQUEY-UHFFFAOYSA-N 0.000 description 1
- HMXJGGUTQZQUTJ-UHFFFAOYSA-N 3-[4-(2,5-dimethylphenyl)piperazin-1-yl]propan-1-ol Chemical compound CC1=CC=C(C)C(N2CCN(CCCO)CC2)=C1 HMXJGGUTQZQUTJ-UHFFFAOYSA-N 0.000 description 1
- QKJXXGNRTAANSC-UHFFFAOYSA-N 3-[4-(2,5-dimethylphenyl)piperazin-1-yl]propyl furan-2-carboxylate;dihydrochloride Chemical compound Cl.Cl.CC1=CC=C(C)C(N2CCN(CCCOC(=O)C=3OC=CC=3)CC2)=C1 QKJXXGNRTAANSC-UHFFFAOYSA-N 0.000 description 1
- VYDVGSPQFPUTGU-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl furan-2-carboxylate;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC=C1N1CCN(CCCOC(=O)C=2OC=CC=2)CC1 VYDVGSPQFPUTGU-UHFFFAOYSA-N 0.000 description 1
- UIPNEMHIQYJIIL-UHFFFAOYSA-N 3-[4-(3-chlorophenyl)piperazin-1-yl]propyl furan-2-carboxylate;dihydrochloride Chemical compound Cl.Cl.ClC1=CC=CC(N2CCN(CCCOC(=O)C=3OC=CC=3)CC2)=C1 UIPNEMHIQYJIIL-UHFFFAOYSA-N 0.000 description 1
- DGSWVEFXJNJPNK-UHFFFAOYSA-N 3-[4-(3-methoxyphenyl)piperazin-1-yl]propan-1-ol Chemical compound COC1=CC=CC(N2CCN(CCCO)CC2)=C1 DGSWVEFXJNJPNK-UHFFFAOYSA-N 0.000 description 1
- GODBTBASCNBWTC-UHFFFAOYSA-N 3-[4-(3-methoxyphenyl)piperazin-1-yl]propyl furan-2-carboxylate;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC(N2CCN(CCCOC(=O)C=3OC=CC=3)CC2)=C1 GODBTBASCNBWTC-UHFFFAOYSA-N 0.000 description 1
- YCAOTOCJYOKDAV-UHFFFAOYSA-N 3-[4-(3-phenylpropyl)piperazin-1-yl]propan-1-ol Chemical compound C1CN(CCCO)CCN1CCCC1=CC=CC=C1 YCAOTOCJYOKDAV-UHFFFAOYSA-N 0.000 description 1
- IKJKDQUTTOGGPC-UHFFFAOYSA-N 3-[4-(3-phenylpropyl)piperazin-1-yl]propyl 9h-xanthene-9-carboxylate;dihydrochloride Chemical compound Cl.Cl.C12=CC=CC=C2OC2=CC=CC=C2C1C(=O)OCCCN(CC1)CCN1CCCC1=CC=CC=C1 IKJKDQUTTOGGPC-UHFFFAOYSA-N 0.000 description 1
- UGDTVTGAQKFKAU-UHFFFAOYSA-N 3-[4-(4-methoxyphenyl)piperazin-1-yl]propan-1-ol Chemical compound C1=CC(OC)=CC=C1N1CCN(CCCO)CC1 UGDTVTGAQKFKAU-UHFFFAOYSA-N 0.000 description 1
- PJINHFPUYHDKGN-UHFFFAOYSA-N 3-[4-(4-methoxyphenyl)piperazin-1-yl]propyl furan-2-carboxylate;dihydrochloride Chemical compound Cl.Cl.C1=CC(OC)=CC=C1N1CCN(CCCOC(=O)C=2OC=CC=2)CC1 PJINHFPUYHDKGN-UHFFFAOYSA-N 0.000 description 1
- HQEXPCJZCHRWDZ-UHFFFAOYSA-N 3-[4-[(3,4,5-trimethoxyphenyl)methyl]piperazin-1-yl]propan-1-ol Chemical compound COC1=C(OC)C(OC)=CC(CN2CCN(CCCO)CC2)=C1 HQEXPCJZCHRWDZ-UHFFFAOYSA-N 0.000 description 1
- YLTWCCPKJQIQRR-UHFFFAOYSA-N 3-[4-[(3-methoxycyclohexyl)methyl]piperazin-1-yl]propan-1-ol Chemical compound C1C(OC)CCCC1CN1CCN(CCCO)CC1 YLTWCCPKJQIQRR-UHFFFAOYSA-N 0.000 description 1
- RENFEDDIYYZJHC-UHFFFAOYSA-N 3-[4-[2-(2-methoxyphenyl)ethyl]piperazin-1-yl]propan-1-ol Chemical compound COC1=CC=CC=C1CCN1CCN(CCCO)CC1 RENFEDDIYYZJHC-UHFFFAOYSA-N 0.000 description 1
- UEZPJLWDYMUKQM-UHFFFAOYSA-N 3-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]propan-1-ol Chemical compound C1CN(CCCO)CCN1C1=CC=CC(C(F)(F)F)=C1 UEZPJLWDYMUKQM-UHFFFAOYSA-N 0.000 description 1
- BEVIOKZUBPMNFX-UHFFFAOYSA-N 3-[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]propyl furan-2-carboxylate;dihydrochloride Chemical compound Cl.Cl.FC(F)(F)C1=CC=CC(N2CCN(CCCOC(=O)C=3OC=CC=3)CC2)=C1 BEVIOKZUBPMNFX-UHFFFAOYSA-N 0.000 description 1
- LWEOFVINMVZGAS-UHFFFAOYSA-N 3-piperazin-1-ylpropan-1-ol Chemical class OCCCN1CCNCC1 LWEOFVINMVZGAS-UHFFFAOYSA-N 0.000 description 1
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- JNANLGAZMJOZBL-UHFFFAOYSA-N ethyl 4-(3-hydroxypropyl)piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCN(CCCO)CC1 JNANLGAZMJOZBL-UHFFFAOYSA-N 0.000 description 1
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 1
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- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- HKHVOAWFHWULQC-UHFFFAOYSA-N propyl 9H-xanthene-9-carboxylate dihydrochloride Chemical compound Cl.Cl.C1=CC=C2C(C(=O)OCCC)C3=CC=CC=C3OC2=C1 HKHVOAWFHWULQC-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Anesthesiology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HURI000605 | 1976-12-15 | ||
| HU76RI605A HU174215B (hu) | 1976-12-15 | 1976-12-15 | Sposob poluchenija novykh proizvodnykh piperazina i kislotnykh additivnykh i chetvjortichnykh solej |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI773743A7 FI773743A7 (fi) | 1978-06-16 |
| FI65427B FI65427B (fi) | 1984-01-31 |
| FI65427C true FI65427C (fi) | 1984-05-10 |
Family
ID=11001009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI773743A FI65427C (fi) | 1976-12-15 | 1977-12-12 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara xanten- eller furankarbonyloxipropanpiperazin-derivat |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US4140790A (enExample) |
| JP (2) | JPS6026114B2 (enExample) |
| AT (1) | AT359507B (enExample) |
| BE (1) | BE861849A (enExample) |
| CA (1) | CA1080219A (enExample) |
| CH (1) | CH632750A5 (enExample) |
| DE (1) | DE2755707A1 (enExample) |
| ES (1) | ES465061A1 (enExample) |
| FI (1) | FI65427C (enExample) |
| FR (1) | FR2374322A1 (enExample) |
| GB (1) | GB1580227A (enExample) |
| HU (1) | HU174215B (enExample) |
| IL (1) | IL53552A (enExample) |
| IN (1) | IN146474B (enExample) |
| NL (1) | NL7713827A (enExample) |
| NO (1) | NO147306C (enExample) |
| PT (1) | PT67403B (enExample) |
| SE (1) | SE430159B (enExample) |
| SU (1) | SU694071A3 (enExample) |
| YU (1) | YU293677A (enExample) |
| ZA (1) | ZA777398B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU174215B (hu) * | 1976-12-15 | 1979-11-28 | Richter Gedeon Vegyeszet | Sposob poluchenija novykh proizvodnykh piperazina i kislotnykh additivnykh i chetvjortichnykh solej |
| US4703120A (en) * | 1986-04-28 | 1987-10-27 | Ortho Pharmaceutical Corporation | Furo(3,4-d)pyrimidine-2,4-dione derivatives and intermediates thereof |
| CN1060168C (zh) * | 1994-05-06 | 2001-01-03 | 中国人民解放军军事医学科学院毒物药物研究所 | 新的呫吨衍生物，其制备方法及含它们的药物组合物 |
| MXPA04007459A (es) | 2002-02-01 | 2005-09-08 | Astrazeneca Ab | Compuestos de quinazolina. |
| JP2006522742A (ja) * | 2003-04-08 | 2006-10-05 | ニューロームド テクノロジーズ、インク． | ピペラジンから距離をおいて配置したベンズヒドリル基から成る一群のカルシウムチャンネル阻害剤 |
| US20080207738A1 (en) * | 2007-02-28 | 2008-08-28 | Cancure Laboratories, Llc | Drug combinations to treat drug resistant tumors |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3481930A (en) * | 1966-11-21 | 1969-12-02 | American Home Prod | Xanthene and thioxanthene-9 ureas and propionamides |
| US3502662A (en) * | 1968-03-18 | 1970-03-24 | American Home Prod | N-(9-xanthenyl or thioxanthenyl)-3-amino or iodo-propionamides and 4-(9-xanthenyl or thioxanthenyl)-thiosemicarbazones |
| FR2201084B1 (enExample) * | 1972-09-29 | 1975-10-31 | Bouchara Emile | |
| US3953449A (en) * | 1973-05-09 | 1976-04-27 | Synthelabo | 2-(4-M-CF3 or -SCF3 phenylpiperazino)-ethyl benzoates |
| HU174215B (hu) * | 1976-12-15 | 1979-11-28 | Richter Gedeon Vegyeszet | Sposob poluchenija novykh proizvodnykh piperazina i kislotnykh additivnykh i chetvjortichnykh solej |
-
1976
- 1976-12-15 HU HU76RI605A patent/HU174215B/hu unknown
-
1977
- 1977-11-25 JP JP52140843A patent/JPS6026114B2/ja not_active Expired
- 1977-12-02 CH CH1475877A patent/CH632750A5/de not_active IP Right Cessation
- 1977-12-05 AT AT867677A patent/AT359507B/de not_active IP Right Cessation
- 1977-12-06 IL IL53552A patent/IL53552A/xx unknown
- 1977-12-07 SE SE7713906A patent/SE430159B/xx unknown
- 1977-12-09 FR FR7737196A patent/FR2374322A1/fr active Granted
- 1977-12-12 US US05/859,928 patent/US4140790A/en not_active Expired - Lifetime
- 1977-12-12 IN IN1717/CAL/77A patent/IN146474B/en unknown
- 1977-12-12 ZA ZA00777398A patent/ZA777398B/xx unknown
- 1977-12-12 YU YU02936/77A patent/YU293677A/xx unknown
- 1977-12-12 FI FI773743A patent/FI65427C/fi not_active IP Right Cessation
- 1977-12-13 SU SU772555706A patent/SU694071A3/ru active
- 1977-12-14 GB GB52038/77A patent/GB1580227A/en not_active Expired
- 1977-12-14 NL NL7713827A patent/NL7713827A/xx not_active Application Discontinuation
- 1977-12-14 JP JP14945477A patent/JPS5377073A/ja active Pending
- 1977-12-14 DE DE19772755707 patent/DE2755707A1/de not_active Ceased
- 1977-12-14 BE BE183452A patent/BE861849A/xx not_active IP Right Cessation
- 1977-12-14 NO NO774294A patent/NO147306C/no unknown
- 1977-12-14 PT PT67403A patent/PT67403B/pt unknown
- 1977-12-14 CA CA293,096A patent/CA1080219A/en not_active Expired
- 1977-12-14 ES ES465061A patent/ES465061A1/es not_active Expired
-
1978
- 1978-12-28 US US05/974,082 patent/US4250310A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA1080219A (en) | 1980-06-24 |
| NO774294L (no) | 1978-06-16 |
| ZA777398B (en) | 1978-10-25 |
| ES465061A1 (es) | 1979-01-01 |
| IL53552A0 (en) | 1978-03-10 |
| CH632750A5 (de) | 1982-10-29 |
| NO147306C (no) | 1983-03-16 |
| SE430159B (sv) | 1983-10-24 |
| AT359507B (de) | 1980-11-10 |
| YU293677A (en) | 1982-08-31 |
| PT67403B (en) | 1979-05-21 |
| IN146474B (enExample) | 1979-06-16 |
| GB1580227A (en) | 1980-11-26 |
| FR2374322A1 (fr) | 1978-07-13 |
| FI773743A7 (fi) | 1978-06-16 |
| JPS5377073A (en) | 1978-07-08 |
| ATA867677A (de) | 1980-04-15 |
| US4250310A (en) | 1981-02-10 |
| SE7713906L (sv) | 1978-06-16 |
| NL7713827A (nl) | 1978-06-19 |
| BE861849A (fr) | 1978-03-31 |
| PT67403A (en) | 1978-01-01 |
| IL53552A (en) | 1981-07-31 |
| FI65427B (fi) | 1984-01-31 |
| DE2755707A1 (de) | 1978-06-29 |
| JPS5377080A (en) | 1978-07-08 |
| NO147306B (no) | 1982-12-06 |
| JPS6026114B2 (ja) | 1985-06-21 |
| SU694071A3 (ru) | 1979-10-25 |
| US4140790A (en) | 1979-02-20 |
| FR2374322B1 (enExample) | 1981-11-27 |
| HU174215B (hu) | 1979-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: RICHTER GEDEON VEGYESZETI GYAR RT. |