CH632750A5 - Verfahren zur herstellung von neuen piperazinderivaten. - Google Patents
Verfahren zur herstellung von neuen piperazinderivaten. Download PDFInfo
- Publication number
- CH632750A5 CH632750A5 CH1475877A CH1475877A CH632750A5 CH 632750 A5 CH632750 A5 CH 632750A5 CH 1475877 A CH1475877 A CH 1475877A CH 1475877 A CH1475877 A CH 1475877A CH 632750 A5 CH632750 A5 CH 632750A5
- Authority
- CH
- Switzerland
- Prior art keywords
- piperazin
- acid addition
- xanthene
- physiologically acceptable
- propane
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title claims description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims description 41
- -1 aliphatic alcohols Chemical class 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- VSBFNCXKYIEYIS-UHFFFAOYSA-N Xanthene-9-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)C3=CC=CC=C3OC2=C1 VSBFNCXKYIEYIS-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000001294 propane Substances 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- PRBASKPGFZYSAI-UHFFFAOYSA-N 3-(4-butylpiperazin-1-yl)propan-1-ol Chemical compound CCCCN1CCN(CCCO)CC1 PRBASKPGFZYSAI-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- 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 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000004885 piperazines Chemical class 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- 125000001680 trimethoxyphenyl group Chemical group 0.000 claims description 2
- MMOMLVPXKBCSMG-UHFFFAOYSA-N 1-benzyl-4-propylpiperazine Chemical compound C1CN(CCC)CCN1CC1=CC=CC=C1 MMOMLVPXKBCSMG-UHFFFAOYSA-N 0.000 claims 1
- UZJJWUSWTWWZEX-UHFFFAOYSA-N 3-[4-(3-methoxyphenyl)piperazin-1-yl]propyl furan-2-carboxylate Chemical compound COC1=CC=CC(N2CCN(CCCOC(=O)C=3OC=CC=3)CC2)=C1 UZJJWUSWTWWZEX-UHFFFAOYSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- YZBJUGHSSZLKRM-UHFFFAOYSA-N ethyl 4-[3-(9h-xanthene-9-carbonyloxy)propyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CCCOC(=O)C1C2=CC=CC=C2OC2=CC=CC=C21 YZBJUGHSSZLKRM-UHFFFAOYSA-N 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- KGMXPXPXPAAUMD-UHFFFAOYSA-N propane;dihydrochloride Chemical compound Cl.Cl.CCC KGMXPXPXPAAUMD-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 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
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 206010003119 arrhythmia Diseases 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 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 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
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ZWAQJGHGPPDZSF-UHFFFAOYSA-N 1-prop-2-enylpiperazine Chemical compound C=CCN1CCNCC1 ZWAQJGHGPPDZSF-UHFFFAOYSA-N 0.000 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
- 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
- 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 2
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-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
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 230000006793 arrhythmia Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 2
- 206010061592 cardiac fibrillation Diseases 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
- 210000004351 coronary vessel Anatomy 0.000 description 2
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229960002768 dipyridamole Drugs 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000002600 fibrillogenic effect Effects 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
- 238000000746 purification Methods 0.000 description 2
- 229960001404 quinidine Drugs 0.000 description 2
- 230000033764 rhythmic process Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 230000002936 tranquilizing effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-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
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 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
- UGMNBYGTGBNHDC-UHFFFAOYSA-N 3-(4-phenylpiperazin-1-yl)propyl 9h-xanthene-9-carboxylate Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C1C(=O)OCCCN(CC1)CCN1C1=CC=CC=C1 UGMNBYGTGBNHDC-UHFFFAOYSA-N 0.000 description 1
- JMBGSFGXQYJFST-UHFFFAOYSA-N 3-[2-methyl-4-(4-methylphenyl)piperazin-1-yl]propan-1-ol Chemical compound C1CN(CCCO)C(C)CN1C1=CC=C(C)C=C1 JMBGSFGXQYJFST-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
- 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 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
- KDDARNQOAVOVCF-UHFFFAOYSA-N 3-[4-(3-methoxyphenyl)piperazin-1-yl]propyl 3-methoxycyclohexane-1-carboxylate;dihydrochloride Chemical compound Cl.Cl.C1C(OC)CCCC1C(=O)OCCCN1CCN(C=2C=C(OC)C=CC=2)CC1 KDDARNQOAVOVCF-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
- 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
- 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
- IUUNRUQKOZOTGA-UHFFFAOYSA-N 3-[4-[(3,4,5-trimethoxyphenyl)methyl]piperazin-1-yl]propyl 9h-xanthene-9-carboxylate;dihydrochloride Chemical compound Cl.Cl.COC1=C(OC)C(OC)=CC(CN2CCN(CCCOC(=O)C3C4=CC=CC=C4OC4=CC=CC=C43)CC2)=C1 IUUNRUQKOZOTGA-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
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- PQQKNRVHFHKIEY-UHFFFAOYSA-N Cl.Cl.Cl.CCC Chemical compound Cl.Cl.Cl.CCC PQQKNRVHFHKIEY-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-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
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 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
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation 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
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid 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
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids 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
- 238000001556 precipitation Methods 0.000 description 1
- UMSVPCYSAUKCAZ-UHFFFAOYSA-N propane;hydrochloride Chemical compound Cl.CCC UMSVPCYSAUKCAZ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000932 sedative agent Substances 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
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 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
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU76RI605A HU174215B (hu) | 1976-12-15 | 1976-12-15 | Sposob poluchenija novykh proizvodnykh piperazina i kislotnykh additivnykh i chetvjortichnykh solej |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH632750A5 true CH632750A5 (de) | 1982-10-29 |
Family
ID=11001009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1475877A CH632750A5 (de) | 1976-12-15 | 1977-12-02 | Verfahren zur herstellung von neuen piperazinderivaten. |
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 |
| FI65427C (fi) | 1984-05-10 |
| ZA777398B (en) | 1978-10-25 |
| ES465061A1 (es) | 1979-01-01 |
| IL53552A0 (en) | 1978-03-10 |
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3586794T2 (de) | Arzneimittel mit psychotroper wirkung. | |
| AT363096B (de) | Verfahren zur herstellung von neuen phthalazinderivaten und deren salzen | |
| DE1670849C3 (de) | Verfahren zur Herstellung von 8-Acylamino-1,23,4-tetrahydroisochinolinen | |
| DE1793759A1 (de) | Mittel zur behandlung bronchospastischer erscheinungen | |
| DE2238504B2 (de) | l-Phenoxy-3-alkylaminopropan-2-ol -Derivate | |
| DE69215626T2 (de) | Trimetazidinederivate, Verfahren zu deren Herstellung und deren pharmazeutischen Zusammensetzungen | |
| DE3334757A1 (de) | Piperazinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate | |
| EP0105210B1 (de) | Isochinolinderivate, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen und ihre Verwendung | |
| DE1815808B2 (de) | 1 -(Alkanoylamiitophenoxy)-3-alkylamino-2-propanole deren Herstellungsverfahren und pharmazeutische Zusammensetzungen auf deren Basis | |
| DE2463088C1 (de) | Substituierte Thienylverbindungen,Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| CH632750A5 (de) | Verfahren zur herstellung von neuen piperazinderivaten. | |
| DE2757532A1 (de) | N,n'-disubstituiertes cyclisches diamin und verfahren zu dessen herstellung | |
| DE1940566B2 (de) | 1- (2-Nitrilophenoxy)-2-hydroxy-3äthylaminopropan, Verfahren zu dessen Herstellung und diese enthaltende Arzneimittel | |
| DE2427272C3 (de) | 1-(2-(β-Naphthyloxy)-äthyl)-3-methyl -pyrazolon-(5), Verfahren sowie Verwendung als Antithrombotikum | |
| DE2609746A1 (de) | Piperazinverbindungen sowie arzneimittel, die diese verbindungen enthalten | |
| DE2439284C2 (de) | 2-Phenyl-3-amino-4-acetyl-5-methylpyrrol, dessen Salze und diese Verbindungen enthaltende pharmazeutische Zubereitung | |
| DE2517020A1 (de) | Alkanolaminderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE3113087C2 (de) | 1,4-Disubstituierte Piperazine, deren Salze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2062055C3 (de) | Propanolamin-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel | |
| CH635337A5 (de) | 3-(4-(2'-pyridyl)-piperazin-1-yl)-1-(3,4,5-trimethoxy-benzoyloxy)-propan, verfahren zur herstellung sowie diese verbindung enthaltende arzneimittel. | |
| DE1445638C (de) | 9 geschweifte Klammer auf gamma eckige Klammer auf N* (beta hydroxyaryl) piperazino eckige Klammer zu propyl geschweifte Klam mer zu 9,10 dihydro 9,10 athano (1,2) anthra zen und seme Salze, Verfahren zu deren Her stellung und pharmazeutisches Mittel | |
| DE1568734C3 (de) | N-Dialkyl-aminoalkyl-S-diphenylsulfoximine und ihre Salze sowie Verfahren zu ihrer Herstellung | |
| DE1151509B (de) | Verfahren zur Herstellung von Phenthiazinderivaten | |
| DE1445416C3 (de) | N-substituierte 23-Polymethylenindole, ein Verfahren zu ihrer Herstellung und Arzneimittel | |
| DE2215545C3 (de) | Pyridin-2-carbonsäurepiperazide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |