NO862138L - Analogifremgangsmaate for fremstilling av terapeutisk aktive n-fenyl-4-fenyl-1-piperazincarboxamidiner og beslektede forbindelser. - Google Patents
Analogifremgangsmaate for fremstilling av terapeutisk aktive n-fenyl-4-fenyl-1-piperazincarboxamidiner og beslektede forbindelser.Info
- Publication number
- NO862138L NO862138L NO862138A NO862138A NO862138L NO 862138 L NO862138 L NO 862138L NO 862138 A NO862138 A NO 862138A NO 862138 A NO862138 A NO 862138A NO 862138 L NO862138 L NO 862138L
- Authority
- NO
- Norway
- Prior art keywords
- hydrogen
- alkyl
- formula
- compound according
- piperazinecarboxamidine
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 134
- 238000002360 preparation method Methods 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 19
- 230000001225 therapeutic effect Effects 0.000 title claims 2
- 239000002253 acid Substances 0.000 claims description 80
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 239000001257 hydrogen Substances 0.000 claims description 64
- -1 -OH Chemical group 0.000 claims description 52
- 150000003839 salts Chemical class 0.000 claims description 41
- 150000002431 hydrogen Chemical class 0.000 claims description 38
- 150000002148 esters Chemical class 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000001589 carboacyl group Chemical group 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- HBGHJWNGKZSGQY-UHFFFAOYSA-N n'-(3,5-dichlorophenyl)-4-(4-hydroxy-2-methoxyphenyl)piperazine-1-carboximidamide Chemical compound COC1=CC(O)=CC=C1N1CCN(C(N)=NC=2C=C(Cl)C=C(Cl)C=2)CC1 HBGHJWNGKZSGQY-UHFFFAOYSA-N 0.000 claims description 9
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 9
- 239000012458 free base Substances 0.000 claims description 8
- CTQJQDJECZVMQZ-UHFFFAOYSA-N n'-(3,5-dichlorophenyl)-4-(2-methoxyphenyl)piperazine-1-carboximidamide Chemical compound COC1=CC=CC=C1N1CCN(C(N)=NC=2C=C(Cl)C=C(Cl)C=2)CC1 CTQJQDJECZVMQZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 238000012546 transfer Methods 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 6
- 206010003119 arrhythmia Diseases 0.000 claims description 6
- 230000006793 arrhythmia Effects 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- LNLHBFVYXUXLFX-UHFFFAOYSA-N 4-(2-methoxyphenyl)-n'-(2-methylpropyl)-n-phenylpiperazine-1-carboximidamide Chemical compound COC1=CC=CC=C1N1CCN(C(NC=2C=CC=CC=2)=NCC(C)C)CC1 LNLHBFVYXUXLFX-UHFFFAOYSA-N 0.000 claims description 3
- IJEPCVKPPXQPBQ-UHFFFAOYSA-N n'-(3,4-dichlorophenyl)-4-(2-methoxyphenyl)piperazine-1-carboximidamide Chemical compound COC1=CC=CC=C1N1CCN(C(N)=NC=2C=C(Cl)C(Cl)=CC=2)CC1 IJEPCVKPPXQPBQ-UHFFFAOYSA-N 0.000 claims description 3
- NRKGVSYVKJHVRF-UHFFFAOYSA-N n'-(3,5-dichlorophenyl)-4-(4-fluorophenyl)piperazine-1-carboximidamide Chemical compound C1=CC(F)=CC=C1N1CCN(C(=N)NC=2C=C(Cl)C=C(Cl)C=2)CC1 NRKGVSYVKJHVRF-UHFFFAOYSA-N 0.000 claims description 3
- RBOMQXYVSYEKPG-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-4-(2-methoxyphenyl)-n'-(2-methylpropyl)piperazine-1-carboximidamide Chemical compound COC1=CC=CC=C1N1CCN(C(NC=2C=C(Cl)C(Cl)=CC=2)=NCC(C)C)CC1 RBOMQXYVSYEKPG-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
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- 239000000203 mixture Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- 239000000243 solution Substances 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
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- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
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- 150000001448 anilines Chemical class 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 6
- 230000003000 nontoxic effect Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
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Classifications
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- 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
-
- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/20—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 acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/739,393 US4713382A (en) | 1985-05-30 | 1985-05-30 | N-phenyl-4-phenyl-1-piperazinecarboxamidines and related compounds as antiarrhythmic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO862138L true NO862138L (no) | 1986-12-01 |
Family
ID=24972082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO862138A NO862138L (no) | 1985-05-30 | 1986-05-29 | Analogifremgangsmaate for fremstilling av terapeutisk aktive n-fenyl-4-fenyl-1-piperazincarboxamidiner og beslektede forbindelser. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4713382A (xx) |
| EP (1) | EP0204265A1 (xx) |
| JP (1) | JPS61280486A (xx) |
| KR (1) | KR860008999A (xx) |
| CN (1) | CN86103798A (xx) |
| AU (1) | AU5805086A (xx) |
| DD (1) | DD247452A5 (xx) |
| DK (1) | DK253586A (xx) |
| ES (1) | ES8708132A1 (xx) |
| FI (1) | FI862279A (xx) |
| GR (1) | GR861370B (xx) |
| HU (1) | HU195201B (xx) |
| IL (1) | IL78963A0 (xx) |
| NO (1) | NO862138L (xx) |
| PT (1) | PT82675B (xx) |
| ZA (1) | ZA864023B (xx) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3040473B2 (ja) * | 1991-08-14 | 2000-05-15 | プロクター、エンド、ギャンブル、ファーマスーティカルズ、インコーポレーテッド | 抗不整脈及び抗細動剤として有用な新規４−オキソ環式尿素類 |
| AU2013292519B2 (en) * | 2012-07-19 | 2017-12-07 | Drexel University | Sigma receptor ligands for modulating cellular protein homeostasis |
| US11117870B2 (en) | 2017-11-01 | 2021-09-14 | Drexel University | Compounds, compositions, and methods for treating diseases |
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|---|---|---|---|---|
| CA574981A (en) * | 1959-04-28 | H. Brown Edwin | Fluid pressure bearing and seal for centrifugal pump | |
| GB948766A (en) * | 1959-10-20 | 1964-02-05 | May & Baker Ltd | Trifluoromethylphenylpiperazine derivatives |
| US3655667A (en) * | 1968-04-04 | 1972-04-11 | Smith Kline French Lab | 1-(2-benzoylcyclopropylmethyl)-4-phenylpiperazines |
| PH12016A (en) * | 1972-09-22 | 1978-10-06 | Rorer Inc William H | Amidinoureas |
| US3793322A (en) * | 1972-12-15 | 1974-02-19 | Usv Pharma Corp | 1,4-disubstituted piperazines |
| US3976643A (en) * | 1973-07-13 | 1976-08-24 | William H. Rorer, Inc. | Guanidines |
| US3961056A (en) * | 1974-02-11 | 1976-06-01 | The Upjohn Company | Substituted morpholine guanidines for the treatment of arrhythmic conditions |
| GB1514907A (en) * | 1975-05-30 | 1978-06-21 | Rorer Inc William H | Process for the preparation of substituted phenylguanidines and substituted phenylguanidines when thus prepared |
| US4211867A (en) * | 1976-03-19 | 1980-07-08 | Mcneil Laboratories, Incorporated | Nitrogen heterocyclic carboximidamide compounds |
| US4138561A (en) * | 1977-09-30 | 1979-02-06 | Bristol-Myers Company | Cyanocarboxamidines and quinazoline process |
| EP0005385B1 (fr) * | 1978-04-27 | 1982-09-01 | LAROCHE NAVARRON S.A. Société dite: | Dérivés de la pipérazine méthanimine, leur procédé de préparation et leurs applications en thérapeutique |
| CH643549A5 (de) * | 1979-08-25 | 1984-06-15 | Merz & Co | N-(trimethoxybenzyl)-n'-phenylpiperazine. |
| US4374835A (en) * | 1980-01-31 | 1983-02-22 | Laroche-Navarron, S.A. | Piperazine derivatives of theophylline |
-
1985
- 1985-05-30 US US06/739,393 patent/US4713382A/en not_active Expired - Fee Related
-
1986
- 1986-05-28 GR GR861370A patent/GR861370B/el unknown
- 1986-05-28 PT PT82675A patent/PT82675B/pt unknown
- 1986-05-29 HU HU862258A patent/HU195201B/hu unknown
- 1986-05-29 FI FI862279A patent/FI862279A/fi not_active Application Discontinuation
- 1986-05-29 ES ES555440A patent/ES8708132A1/es not_active Expired
- 1986-05-29 KR KR1019860004227A patent/KR860008999A/ko not_active Application Discontinuation
- 1986-05-29 AU AU58050/86A patent/AU5805086A/en not_active Abandoned
- 1986-05-29 CN CN198686103798A patent/CN86103798A/zh active Pending
- 1986-05-29 EP EP86107310A patent/EP0204265A1/en not_active Withdrawn
- 1986-05-29 ZA ZA864023A patent/ZA864023B/xx unknown
- 1986-05-29 NO NO862138A patent/NO862138L/no unknown
- 1986-05-29 DK DK253586A patent/DK253586A/da not_active Application Discontinuation
- 1986-05-29 JP JP61125592A patent/JPS61280486A/ja active Pending
- 1986-05-29 IL IL78963A patent/IL78963A0/xx unknown
- 1986-05-30 DD DD86290764A patent/DD247452A5/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU5805086A (en) | 1986-12-04 |
| FI862279A (fi) | 1986-12-01 |
| HUT41016A (en) | 1987-03-30 |
| EP0204265A1 (en) | 1986-12-10 |
| DD247452A5 (de) | 1987-07-08 |
| DK253586A (da) | 1986-12-01 |
| FI862279A0 (fi) | 1986-05-29 |
| CN86103798A (zh) | 1987-06-10 |
| ES555440A0 (es) | 1987-10-16 |
| US4713382A (en) | 1987-12-15 |
| GR861370B (en) | 1986-09-17 |
| ES8708132A1 (es) | 1987-10-16 |
| PT82675B (en) | 1987-09-29 |
| ZA864023B (en) | 1988-01-27 |
| DK253586D0 (da) | 1986-05-29 |
| JPS61280486A (ja) | 1986-12-11 |
| PT82675A (en) | 1986-06-01 |
| HU195201B (en) | 1988-04-28 |
| IL78963A0 (en) | 1986-09-30 |
| KR860008999A (ko) | 1986-12-19 |
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