DE1937811A1 - Neue 1,4-substituierte Phenylpiperazine - Google Patents

Neue 1,4-substituierte Phenylpiperazine

Info

Publication number: DE1937811A1
Authority: DE; Germany
Prior art keywords: phenyl; piperazine; salts; diethylaminoethyl; chlorobenzyl
Prior art date: 1968-07-26
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

DE19691937811

Other languages

German (de)

English (en)

Inventor

Zellner Dr Gertraud

Zelliner Dr Hugo

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Donau-Pharmazie GmbH

Original Assignee

Donau-Pharmazie GmbH

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1968-07-26

Filing date

1969-07-25

Publication date

1970-01-29

1969-07-25 Application filed by Donau-Pharmazie GmbH filed Critical Donau-Pharmazie GmbH

1970-01-29 Publication of DE1937811A1 publication Critical patent/DE1937811A1/de

Status Pending legal-status Critical Current

Links

YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 title description 5
-1 dimethylaminoethyl Chemical group 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 25
MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 21
150000001875 compounds Chemical class 0.000 claims description 13
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
150000003254 radicals Chemical class 0.000 claims description 8
239000003146 anticoagulant agent Substances 0.000 claims description 5
229940127219 anticoagulant drug Drugs 0.000 claims description 5
150000004885 piperazines Chemical class 0.000 claims description 5
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
CFNQBNSZXFEPBW-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-2-phenyl-4-(2-piperidin-1-ylethyl)piperazine Chemical compound C1=CC(Cl)=CC=C1CN1C(C=2C=CC=CC=2)CN(CCN2CCCCC2)CC1 CFNQBNSZXFEPBW-UHFFFAOYSA-N 0.000 claims 1
229930194542 Keto Natural products 0.000 claims 1
125000004803 chlorobenzyl group Chemical group 0.000 claims 1
125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 90
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 57
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 55
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 47
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
239000002585 base Substances 0.000 description 27
239000002904 solvent Substances 0.000 description 27
239000003921 oil Substances 0.000 description 26
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 20
238000009835 boiling Methods 0.000 description 16
235000011121 sodium hydroxide Nutrition 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
239000013078 crystal Substances 0.000 description 13
229910000027 potassium carbonate Inorganic materials 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 11
229910021529 ammonia Inorganic materials 0.000 description 10
238000001914 filtration Methods 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 7
238000010992 reflux Methods 0.000 description 7
235000002639 sodium chloride Nutrition 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
230000001476 alcoholic effect Effects 0.000 description 6
238000001816 cooling Methods 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 4
WKFFHKBGGZHQAX-UHFFFAOYSA-N 3-phenylpiperazin-2-one Chemical compound O=C1NCCNC1C1=CC=CC=C1 WKFFHKBGGZHQAX-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
230000029936 alkylation Effects 0.000 description 4
238000005804 alkylation reaction Methods 0.000 description 4
238000000034 method Methods 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
OQQCVIQZHVVXQG-UHFFFAOYSA-N 1-[2-(diethylamino)ethyl]-3-phenylpiperazin-2-one Chemical compound O=C1N(CCN(CC)CC)CCNC1C1=CC=CC=C1 OQQCVIQZHVVXQG-UHFFFAOYSA-N 0.000 description 3
XZBXAYCCBFTQHH-UHFFFAOYSA-N 3-chloropropylbenzene Chemical compound ClCCCC1=CC=CC=C1 XZBXAYCCBFTQHH-UHFFFAOYSA-N 0.000 description 3
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 3
229910010082 LiAlH Inorganic materials 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
208000007536 Thrombosis Diseases 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
238000004587 chromatography analysis Methods 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
239000012230 colorless oil Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
ZIUSQWKUOOKTMU-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-2-phenylpiperazin-1-yl]-n,n-diethylethanamine Chemical compound C1C(C=2C=CC=CC=2)N(CCN(CC)CC)CCN1CC1=CC=C(Cl)C=C1 ZIUSQWKUOOKTMU-UHFFFAOYSA-N 0.000 description 2
ZCLDHBGCWYMQBW-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-3-phenylpiperazin-1-yl]-n,n-diethylethanamine Chemical compound C=1C=CC=CC=1C1CN(CCN(CC)CC)CCN1CC1=CC=C(Cl)C=C1 ZCLDHBGCWYMQBW-UHFFFAOYSA-N 0.000 description 2
HHODNEBCKLBZOH-UHFFFAOYSA-N 4-[2-(diethylamino)ethyl]-3-phenylpiperazin-2-one Chemical compound CCN(CC)CCN1CCNC(=O)C1C1=CC=CC=C1 HHODNEBCKLBZOH-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
150000001412 amines Chemical class 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
MSQACBWWAIBWIC-UHFFFAOYSA-N hydron;piperazine;chloride Chemical compound Cl.C1CNCCN1 MSQACBWWAIBWIC-UHFFFAOYSA-N 0.000 description 2
JXKSNRRFVDOMAZ-UHFFFAOYSA-N n,n-diethyl-2-(2-phenylpiperazin-1-yl)ethanamine Chemical compound CCN(CC)CCN1CCNCC1C1=CC=CC=C1 JXKSNRRFVDOMAZ-UHFFFAOYSA-N 0.000 description 2
KSIRMSHBIDYZPE-UHFFFAOYSA-N n,n-diethyl-2-(3-phenylpiperazin-1-yl)ethanamine Chemical compound C1N(CCN(CC)CC)CCNC1C1=CC=CC=C1 KSIRMSHBIDYZPE-UHFFFAOYSA-N 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
YZIFVWOCPGPNHB-UHFFFAOYSA-N 1,2-dichloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C(Cl)=C1 YZIFVWOCPGPNHB-UHFFFAOYSA-N 0.000 description 1
PMIAMRAWHYEPNH-UHFFFAOYSA-N 1-(2-chloroethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCCl)C=C1 PMIAMRAWHYEPNH-UHFFFAOYSA-N 0.000 description 1
WNRWEBKEQARBKV-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine Chemical compound ClCCN1CCCCC1 WNRWEBKEQARBKV-UHFFFAOYSA-N 0.000 description 1
DCLMJYZEOSDVCL-UHFFFAOYSA-N 1-(chloromethyl)-4-ethoxybenzene Chemical compound CCOC1=CC=C(CCl)C=C1 DCLMJYZEOSDVCL-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
ZIWQTDIDVQRWAH-UHFFFAOYSA-N 2-hydroxy-3-oxobutanoyl chloride Chemical compound CC(=O)C(O)C(Cl)=O ZIWQTDIDVQRWAH-UHFFFAOYSA-N 0.000 description 1
UZXIUPFYHZTINO-UHFFFAOYSA-N 2-phenyl-1-[(4-phenylmethoxyphenyl)methyl]piperazine Chemical compound C=1C=CC=CC=1COC(C=C1)=CC=C1CN1CCNCC1C1=CC=CC=C1 UZXIUPFYHZTINO-UHFFFAOYSA-N 0.000 description 1
RIMRLBGNCLMSNH-UHFFFAOYSA-N 2-phenylpiperazine Chemical compound C1NCCNC1C1=CC=CC=C1 RIMRLBGNCLMSNH-UHFFFAOYSA-N 0.000 description 1
YPMDKMTXGRUKET-UHFFFAOYSA-N 3-phenyl-4-[(4-phenylmethoxyphenyl)methyl]piperazin-2-one Chemical compound C=1C=CC=CC=1C1C(=O)NCCN1CC(C=C1)=CC=C1OCC1=CC=CC=C1 YPMDKMTXGRUKET-UHFFFAOYSA-N 0.000 description 1
GUBZDPRGTAVKHL-UHFFFAOYSA-N 4-(3-chloro-1-morpholin-4-ylpropyl)morpholine Chemical compound C1COCCN1C(CCCl)N1CCOCC1 GUBZDPRGTAVKHL-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 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
UPJGPZMDCCNPBK-UHFFFAOYSA-N 4-n,4-n-diethylbutane-1,2,4-triamine Chemical compound CCN(CC)CCC(N)CN UPJGPZMDCCNPBK-UHFFFAOYSA-N 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
206010053567 Coagulopathies Diseases 0.000 description 1
UDMBCSSLTHHNCD-UHFFFAOYSA-N Coenzym Q(11) Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(O)=O)C(O)C1O UDMBCSSLTHHNCD-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
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
OEFBSWQIIDQIIG-UHFFFAOYSA-N N,N-dimethylaniline propan-2-one Chemical compound CC(C)=O.CN(C)c1ccccc1 OEFBSWQIIDQIIG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 1
229950006790 adenosine phosphate Drugs 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000023555 blood coagulation Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
210000001627 cerebral artery Anatomy 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
230000035602 clotting Effects 0.000 description 1
210000004351 coronary vessel Anatomy 0.000 description 1
150000004656 dimethylamines Chemical class 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000004907 flux Effects 0.000 description 1
238000006170 formylation reaction Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000010985 leather Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
210000004623 platelet-rich plasma Anatomy 0.000 description 1
CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
JVXZJEUVAOVXIX-UHFFFAOYSA-N propan-2-one;pyridine Chemical compound CC(C)=O.C1=CC=NC=C1 JVXZJEUVAOVXIX-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000002002 slurry Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DE19691937811 1968-07-26 1969-07-25 Neue 1,4-substituierte Phenylpiperazine Pending DE1937811A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
AT730668A AT284127B (de)	1968-07-26	1968-07-26	Verfahren zur Herstellung von neuen 1,4-substituierten Phenylpiperazinen und von deren Salzen

Publications (1)

Publication Number	Publication Date
DE1937811A1 true DE1937811A1 (de)	1970-01-29

Family

ID=3594726

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19691937811 Pending DE1937811A1 (de)	1968-07-26	1969-07-25	Neue 1,4-substituierte Phenylpiperazine

Country Status (10)

Country	Link
AT (1)	AT284127B (el)
BE (1)	BE736520A (el)
CA (1)	CA963904A (el)
CH (3)	CH537936A (el)
DE (1)	DE1937811A1 (el)
DK (1)	DK121955B (el)
FR (1)	FR2013813A1 (el)
GB (1)	GB1266780A (el)
NL (1)	NL6911484A (el)
SE (1)	SE355364B (el)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2601364B1 (fr) *	1986-07-09	1988-10-21	Adir	Nouveaux derives de la piperazine dione-2,6, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent.
FR2616433B1 (fr) *	1987-06-15	1989-09-01	Adir	Nouveaux derives piperazinyl alkyl piperazine, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent
US7041826B2 (en) *	2003-06-02	2006-05-09	Aurobindo Pharma Ltd.	Process for preparing 1-methyl-3-phenylpiperazine using a novel intermediate

1968
- 1968-07-26 AT AT730668A patent/AT284127B/de not_active IP Right Cessation
1969
- 1969-07-18 CH CH1582471A patent/CH537936A/de not_active IP Right Cessation
- 1969-07-18 CH CH1105669A patent/CH520693A/de not_active IP Right Cessation
- 1969-07-18 CH CH1582371A patent/CH540268A/de not_active IP Right Cessation
- 1969-07-24 BE BE736520D patent/BE736520A/xx unknown
- 1969-07-24 GB GB1266780D patent/GB1266780A/en not_active Expired
- 1969-07-25 CA CA057,953A patent/CA963904A/en not_active Expired
- 1969-07-25 SE SE1055169A patent/SE355364B/xx unknown
- 1969-07-25 DK DK405469A patent/DK121955B/da unknown
- 1969-07-25 DE DE19691937811 patent/DE1937811A1/de active Pending
- 1969-07-25 NL NL6911484A patent/NL6911484A/xx unknown
- 1969-07-25 FR FR6925493A patent/FR2013813A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
FR2013813A1 (el)	1970-04-10
DK121955B (da)	1971-12-27
BE736520A (el)	1969-12-31
NL6911484A (el)	1970-01-28
CH540268A (de)	1973-09-28
AT284127B (de)	1970-09-10
CA963904A (en)	1975-03-04
SE355364B (el)	1973-04-16
CH520693A (de)	1972-03-31
GB1266780A (el)	1972-03-15
CH537936A (de)	1973-07-31

Publication	Publication Date	Title
DE2065636A1 (de)	1974-12-19	Neue tricyclische verbindungen
DE69004973T2 (de)	1994-06-23	Piperidine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel.
DE60307875T2 (de)	2007-04-12	Imidazopyrin-derivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zusamensetzungen
DE2415082A1 (de)	1974-10-10	Disubstituierte piperazine, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel
DE1965264A1 (de)	1970-07-16	Pyrazinoylsulfamide und Verfahren zu ihrer Herstellung
DE1620449B2 (de)	1973-07-26	Substituierte benzimidazole und verfahren zu ihrer herstellung
DE2718405A1 (de)	1978-11-02	Neue n- eckige klammer auf 1-(3-benzoylpropyl)-4-piperidyl eckige klammer zu -sulfonsaeureamide und verfahren zu deren herstellung
DE2724434A1 (de)	1979-02-22	Neue, in 11-stellung substituierte 5,11-dihydro-6h-pyrido eckige klammer auf 2,3-b eckige klammer zu eckige klammer auf 1,4 eckige klammer zu benzodiazepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
CH637653A5 (de)	1983-08-15	In 11-stellung substituierte 5,11-dihydro-6h-pyrido(2,3-b)(1,4)benzodiazepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel.
DE2523103A1 (de)	1976-12-09	Neue propargyl-2-phenylamino-imidazoline-(2), deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben
DE3876711T2 (de)	1993-07-01	Piperidin-derivate, deren herstellung und deren verwendung als heilmittel.
DE1470194C3 (de)	1975-07-24	1,3,3-trisubstituierte 4-0mega-(Aminoalkyl) -2-pyrrolidinone und-2-thiopyrrolidinone
DE68912263T2 (de)	1994-06-01	4-Methyl-5[2-(4-phenyl-1-piperazinyl)-ethyl]-Thiazolderivate, ihre Herstellung und Zusammenstellungen, die sie enthalten.
DE1937811A1 (de)	1970-01-29	Neue 1,4-substituierte Phenylpiperazine
DE2335432A1 (de)	1975-01-30	3,4-dihydro-2h-naphthalinon-(1)5-oxy-propyl-piperazin-derivate und verfahren zu ihrer herstellung
DD202563A5 (de)	1983-09-21	Verfahren zur herstellung von 1,5-diphenylpyrazolin-3-on-verbindungen
DE3305495A1 (de)	1983-08-18	Piperazin- und homopiperazinderivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitungen
DE69400692T2 (de)	1997-05-07	Substituierte Piperazine, ihre Verfahrensherstellung und die enthaltenen pharmazeutischen Zusammenfassungen
DE1115259B (de)	1961-10-19	Verfahren zur Herstellung von Iminodibenzylen
DE2002107A1 (de)	1970-07-30	Neue organische Verbindungen und Verfahren zu deren Herstellung
EP0069953A1 (de)	1983-01-19	Triazino-(2,1-a)isochinolinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE3907512C2 (de)	1997-08-14	Neue Aryloxy-alkylamine, deren Herstellung und diese enthaltende Arzneimittel
DE2024045A1 (de)	1970-11-26	Derivate von Dibenzo(a,d)-5Hcyclohepten
DE2004816A1 (de)	1970-08-27	Thienopyridinderivate und Verfahren zu deren Herstellung
DE2215545C3 (de)	1976-03-11	Pyridin-2-carbonsäurepiperazide

Legal Events

Date	Code	Title	Description
1978-05-24	OHJ	Non-payment of the annual fee