CA1054151A - Derives de la n-(trimethoxy-3,4,5 cinnamoyl) piperazine, leur procede de preparation et leur application en therapeutique - Google Patents
Derives de la n-(trimethoxy-3,4,5 cinnamoyl) piperazine, leur procede de preparation et leur application en therapeutiqueInfo
- Publication number
- CA1054151A CA1054151A CA239,824A CA239824A CA1054151A CA 1054151 A CA1054151 A CA 1054151A CA 239824 A CA239824 A CA 239824A CA 1054151 A CA1054151 A CA 1054151A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- radical
- cinnamoyl
- piperazine
- trimethoxy
- Prior art date
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- ZQXXBLADSLNAAT-UHFFFAOYSA-N 1-piperazin-1-yl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one Chemical class COC1=C(OC)C(OC)=CC(C=CC(=O)N2CCNCC2)=C1 ZQXXBLADSLNAAT-UHFFFAOYSA-N 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract description 20
- -1 cinnamoyl Chemical group 0.000 claims abstract description 17
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 8
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000011976 maleic acid Substances 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 125000001302 tertiary amino group Chemical group 0.000 claims abstract description 4
- 231100000252 nontoxic Toxicity 0.000 claims abstract 3
- 230000003000 nontoxic effect Effects 0.000 claims abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000003335 secondary amines Chemical class 0.000 claims description 5
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- WRJZKSHNBALIGH-UHFFFAOYSA-N 2-piperazin-1-ium-1-ylacetate Chemical compound OC(=O)CN1CCNCC1 WRJZKSHNBALIGH-UHFFFAOYSA-N 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 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 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229940124549 vasodilator Drugs 0.000 abstract description 4
- 239000003071 vasodilator agent Substances 0.000 abstract description 4
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 3
- 230000002490 cerebral effect Effects 0.000 abstract description 3
- 241001465754 Metazoa Species 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 2
- 230000002093 peripheral effect Effects 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 210000001367 artery Anatomy 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003218 coronary vasodilator agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000002739 subcortical effect Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 229960002195 perazine Drugs 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 210000003462 vein Anatomy 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
- C07D295/16—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
- C07D295/18—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 carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- 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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7438203A FR2291754A2 (fr) | 1974-11-20 | 1974-11-20 | Nouveau derive de la n-(trimethoxy-3,4,5 cinnamoyl) piperazine, son procede de preparation et son application en therapeutique |
| FR7529782A FR2325372A2 (fr) | 1975-09-29 | 1975-09-29 | Nouveaux derives de la n-(trimethoxy-3,4,5 cinaamoyl) piperazine, leur procede de preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1054151A true CA1054151A (fr) | 1979-05-08 |
Family
ID=26218609
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA239,824A Expired CA1054151A (fr) | 1974-11-20 | 1975-11-17 | Derives de la n-(trimethoxy-3,4,5 cinnamoyl) piperazine, leur procede de preparation et leur application en therapeutique |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4029650A (en, 2012) |
| JP (1) | JPS609506B2 (en, 2012) |
| AU (1) | AU503778B2 (en, 2012) |
| CA (1) | CA1054151A (en, 2012) |
| CH (1) | CH580091A5 (en, 2012) |
| DE (1) | DE2550851C2 (en, 2012) |
| ES (1) | ES442845A2 (en, 2012) |
| GB (1) | GB1473262A (en, 2012) |
| IT (1) | IT1055691B (en, 2012) |
| LU (1) | LU73671A1 (en, 2012) |
| NL (1) | NL7513538A (en, 2012) |
| SE (1) | SE417515B (en, 2012) |
| SU (1) | SU592357A3 (en, 2012) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2387971A1 (fr) * | 1977-04-19 | 1978-11-17 | Delalande Sa | Nouvelles trimethoxy cinnamoyles piperazines, leur procede de preparation et leur application en therapeutique |
| GR71991B (en, 2012) * | 1980-01-21 | 1983-08-26 | Delalande Sa | |
| JPS5888370A (ja) * | 1981-11-19 | 1983-05-26 | Hokuriku Seiyaku Co Ltd | １−（３，４，５−トリメトキシシンナモイル）−４−アミノカルボニルエチル置換ピペラジン及びホモピペラジン誘導体、及びその製造方法 |
| FR2522325B1 (fr) * | 1982-02-26 | 1985-08-09 | Delalande Sa | Nouveaux derives aryliques de la piperazine, de l'homopiperazine et de n,n'-dialkyl diamino-1,2 ethane, leur procede de preparation et leur application en therapeutique |
| FR2552762B1 (fr) * | 1983-09-30 | 1986-07-25 | Delalande Sa | Nouveaux amides piperaziniques et homopiperaziniques derives de l'acide 3,4-dioxymethylene cinnamique, leur procede de preparation et leur application en therapeutique |
| JPS6172773A (ja) * | 1984-09-17 | 1986-04-14 | Terumo Corp | ピペラジン誘導体およびこれを含有する血管拡張剤 |
| JPS6332603U (en, 2012) * | 1986-08-18 | 1988-03-02 | ||
| JPS6428906U (en, 2012) * | 1987-08-08 | 1989-02-21 | ||
| IL92011A0 (en) * | 1988-10-19 | 1990-07-12 | Abbott Lab | Heterocyclic peptide renin inhibitors |
| US5164388A (en) * | 1988-10-19 | 1992-11-17 | Abbott Laboratories | Heterocyclic peptide renin inhibitors |
| US5541622A (en) * | 1990-07-24 | 1996-07-30 | Incontrol Solutions, Inc. | Miniature isometric joystick |
| US6432957B1 (en) * | 2001-06-29 | 2002-08-13 | Kowa Co., Ltd. | Piperazine derivative |
| WO2004046110A1 (ja) * | 2002-11-15 | 2004-06-03 | Yamanouchi Pharmaceutical Co., Ltd. | メラニン凝集ホルモン受容体拮抗剤 |
| CN101906085B (zh) * | 2009-06-04 | 2013-12-11 | 天津药物研究院 | 治疗心脑血管疾病的化合物、组合物、制备方法及用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1178400A (en) * | 1966-12-13 | 1970-01-21 | Delalande Sa | Nitrogen Substituted Amines and their process of Preparation. |
| GB1218591A (en) * | 1968-04-03 | 1971-01-06 | Delalande Sa | Derivatives of n-(3,4,5-trimethoxy cennamoyl) piperazine and their process of preparation |
| US3753984A (en) * | 1971-05-26 | 1973-08-21 | Delalande Sa | Amides derived from the esters of 1-piperazine propionic acid, their method of preparation and their application to therapeutics |
-
1975
- 1975-10-28 GB GB4428375A patent/GB1473262A/en not_active Expired
- 1975-10-29 LU LU73671A patent/LU73671A1/xx unknown
- 1975-10-31 CH CH1411175A patent/CH580091A5/xx not_active IP Right Cessation
- 1975-11-12 DE DE2550851A patent/DE2550851C2/de not_active Expired
- 1975-11-14 JP JP50136403A patent/JPS609506B2/ja not_active Expired
- 1975-11-14 AU AU86658/75A patent/AU503778B2/en not_active Expired
- 1975-11-17 CA CA239,824A patent/CA1054151A/fr not_active Expired
- 1975-11-19 NL NL7513538A patent/NL7513538A/xx not_active Application Discontinuation
- 1975-11-19 SE SE7513011A patent/SE417515B/xx unknown
- 1975-11-19 IT IT69852/75A patent/IT1055691B/it active
- 1975-11-20 US US05/633,932 patent/US4029650A/en not_active Expired - Lifetime
- 1975-11-20 ES ES442845A patent/ES442845A2/es not_active Expired
- 1975-11-20 SU SU752190956A patent/SU592357A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| LU73671A1 (en, 2012) | 1976-08-19 |
| DE2550851C2 (de) | 1982-11-11 |
| SE7513011L (sv) | 1976-05-21 |
| NL7513538A (nl) | 1976-05-24 |
| SE417515B (sv) | 1981-03-23 |
| US4029650A (en) | 1977-06-14 |
| ES442845A2 (es) | 1977-05-16 |
| SU592357A3 (ru) | 1978-02-05 |
| AU8665875A (en) | 1977-05-19 |
| JPS51101988A (en) | 1976-09-08 |
| GB1473262A (en) | 1977-05-11 |
| AU503778B2 (en) | 1979-09-20 |
| IT1055691B (it) | 1982-01-11 |
| JPS609506B2 (ja) | 1985-03-11 |
| CH580091A5 (en, 2012) | 1976-09-30 |
| DE2550851A1 (de) | 1976-05-26 |
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