FR2462432A2 - Nouveaux derives de la 3,4,5 trimethoxy cinnamoyle piperazine, leur procede de preparation et leur application en therapeutique - Google Patents
Nouveaux derives de la 3,4,5 trimethoxy cinnamoyle piperazine, leur procede de preparation et leur application en therapeutique Download PDFInfo
- Publication number
- FR2462432A2 FR2462432A2 FR7919990A FR7919990A FR2462432A2 FR 2462432 A2 FR2462432 A2 FR 2462432A2 FR 7919990 A FR7919990 A FR 7919990A FR 7919990 A FR7919990 A FR 7919990A FR 2462432 A2 FR2462432 A2 FR 2462432A2
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- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 8
- DLCYXQODDJUHQL-VOTSOKGWSA-N (e)-3-phenyl-1-piperazin-1-ylprop-2-en-1-one Chemical compound C1CNCCN1C(=O)\C=C\C1=CC=CC=C1 DLCYXQODDJUHQL-VOTSOKGWSA-N 0.000 title claims description 5
- 230000001225 therapeutic effect Effects 0.000 title description 3
- -1 PHENYL GROUP Chemical group 0.000 claims abstract description 22
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims abstract description 3
- 210000000748 cardiovascular system Anatomy 0.000 claims abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000003814 drug Substances 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 64
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 3
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- HLPBHWMIZHQNRC-UHFFFAOYSA-N (2-ethoxyphenyl) acetate Chemical compound CCOC1=CC=CC=C1OC(C)=O HLPBHWMIZHQNRC-UHFFFAOYSA-N 0.000 claims description 2
- HPARLNRMYDSBNO-UHFFFAOYSA-N 1,4-benzodioxine Chemical group C1=CC=C2OC=COC2=C1 HPARLNRMYDSBNO-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 210000000988 bone and bone Anatomy 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 150000002924 oxiranes Chemical class 0.000 claims description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 2
- 230000009885 systemic effect Effects 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
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- 229940079593 drug Drugs 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical group C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 abstract description 11
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
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- AEELHPSJKHUGEA-UHFFFAOYSA-N 2-methylbut-1-ene Chemical class [CH2+]C(=C)C[CH2-] AEELHPSJKHUGEA-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical group 0.000 abstract 1
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 70
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
- 125000005605 benzo group Chemical group 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 229910001868 water Inorganic materials 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000001228 spectrum Methods 0.000 description 11
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- 230000008018 melting Effects 0.000 description 10
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- ZQXXBLADSLNAAT-UHFFFAOYSA-N 1-piperazin-1-yl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one Chemical compound COC1=C(OC)C(OC)=CC(C=CC(=O)N2CCNCC2)=C1 ZQXXBLADSLNAAT-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XSPXZEGNOAVEOZ-UHFFFAOYSA-N 2,3,7,8-tetrahydro-1,4-benzodioxine Chemical compound C1CC2=C(OCCO2)C=C1 XSPXZEGNOAVEOZ-UHFFFAOYSA-N 0.000 description 3
- OXXFSDSZIMQPJC-UHFFFAOYSA-N 2-ethoxy-1-(2-hydroxyphenyl)ethanone Chemical compound CCOCC(=O)C1=CC=CC=C1O OXXFSDSZIMQPJC-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 235000011167 hydrochloric acid Nutrition 0.000 description 3
- KNFJXUPAAYVKII-UHFFFAOYSA-N methyl N-(5-hydroxy-2,3-dihydro-1,4-benzodioxin-8-yl)carbamate Chemical compound OC1=CC=C(C=2OCCOC=21)NC(=O)OC KNFJXUPAAYVKII-UHFFFAOYSA-N 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- ZBIAKUMOEKILTF-UHFFFAOYSA-N 2-[4-[4,4-bis(4-fluorophenyl)butyl]-1-piperazinyl]-N-(2,6-dimethylphenyl)acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 ZBIAKUMOEKILTF-UHFFFAOYSA-N 0.000 description 2
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- 101150065749 Churc1 gene Proteins 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
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- IYIKLHRQXLHMJQ-UHFFFAOYSA-N amiodarone Chemical compound CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCCN(CC)CC)C(I)=C1 IYIKLHRQXLHMJQ-UHFFFAOYSA-N 0.000 description 2
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- PZVIQOFUJGMMFC-UHFFFAOYSA-N methyl N-(5-phenylmethoxy-2,3-dihydro-1,4-benzodioxin-8-yl)carbamate Chemical compound C(C1=CC=CC=C1)OC1=CC=C(C=2OCCOC=21)NC(=O)OC PZVIQOFUJGMMFC-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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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
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7919990A FR2462432A2 (fr) | 1979-08-03 | 1979-08-03 | Nouveaux derives de la 3,4,5 trimethoxy cinnamoyle piperazine, leur procede de preparation et leur application en therapeutique |
| CH551180A CH646694A5 (fr) | 1979-08-03 | 1980-07-18 | Derives de la 3,4,5-trimethoxy cinnamoyle piperazine et leur procede de preparation. |
| CA000356675A CA1155121A (en) | 1979-08-03 | 1980-07-21 | Derivatives of 3,4,5-trimethoxy cinnamoyl piperazine, the process for preparing the same and their use in therapeutics |
| SE8005300A SE8005300L (sv) | 1979-08-03 | 1980-07-22 | Nya derivat 3,4,5-trimetoxicinnamoylpiperazin, deras framstellning och anvendning som lekemedel |
| GR62561A GR68073B (enrdf_load_stackoverflow) | 1979-08-03 | 1980-07-28 | |
| IT23763/80A IT1219979B (it) | 1977-04-19 | 1980-07-29 | Derivati della 3,4,5-trimetossicinnamoil-piperazina,loro procedimento di preparazione e loro applicazione terapeutica |
| DE19803028912 DE3028912A1 (de) | 1979-08-03 | 1980-07-30 | Neue derivate des 3,45-trimethoxycinnamoyl-piperazins, verfahren zu ihrer herstellung und solche derivate |
| BE0/201625A BE884602R (fr) | 1979-08-03 | 1980-08-01 | Nouvelles cinnamoyles piperazines et homopiperazines leur procede de preparation et leur application en therapeutique |
| LU82677A LU82677A1 (fr) | 1979-08-03 | 1980-08-01 | Nouveaux derives de la 3,4,5-trimethoxy cinnamoyle piperazine,leur procede de preparation et leur application en therapeutique |
| JP10632080A JPS5626885A (en) | 1979-08-03 | 1980-08-01 | Novel derivative of piperazine |
| GB8025200A GB2057433B (en) | 1979-08-03 | 1980-08-01 | 3,4,5-trimethoxy cinnamoyl piperazine derivatives processes for preparing the same and their use in therapeutics |
| ES493931A ES8107195A1 (es) | 1979-08-03 | 1980-08-01 | Procedimiento de preparacion de nuevos derivados de la 3,4,5-trimetoxi-cinamoil-piperazina |
| MX10155280U MX6334E (es) | 1979-08-03 | 1980-08-01 | Procedimiento para preparar derivados de la 3,4,5-trimetoxi-cinamoil piperazina |
| ZA00804709A ZA804709B (en) | 1979-08-03 | 1980-08-01 | Novel derivatives of 3,4,5-trimethoxy cinnamoyl piperazine,the process for preparing the same and their use in therapeutics |
| AU61003/80A AU6100380A (en) | 1979-08-03 | 1980-08-01 | Derivatives of 3,4,5-trimethoxy cinnamoyl piperazine |
| NL8004434A NL8004434A (nl) | 1979-08-03 | 1980-08-04 | Nieuwe 3,4,5-trimethoxy-cinnamoylpiperazine- verbindingen, werkwijze voor hun bereiding en hun toepassing als geneesmiddelen. |
| ES499814A ES8301944A1 (es) | 1979-08-03 | 1981-02-26 | Un procedimiento de preparacion de ((metil-3)-n-butiloxicar-bonil-8-benzodioxan-1,4-il)-oxi-3-((trimetoxi-3,4,5-cinamo- il)-4-piperazin-1-il)-1-propanol-2 (s(-)) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7919990A FR2462432A2 (fr) | 1979-08-03 | 1979-08-03 | Nouveaux derives de la 3,4,5 trimethoxy cinnamoyle piperazine, leur procede de preparation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2462432A2 true FR2462432A2 (fr) | 1981-02-13 |
| FR2462432B2 FR2462432B2 (enrdf_load_stackoverflow) | 1983-05-27 |
Family
ID=9228620
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7919990A Granted FR2462432A2 (fr) | 1977-04-19 | 1979-08-03 | Nouveaux derives de la 3,4,5 trimethoxy cinnamoyle piperazine, leur procede de preparation et leur application en therapeutique |
Country Status (14)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2507604A2 (fr) * | 1977-04-19 | 1982-12-17 | Delalande Sa | Nouvelles trimethoxy-3,4,5 cinnamoyle piperazines, leur procede de preparation et leur application en therapeutique |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4558129A (en) * | 1983-05-18 | 1985-12-10 | Syntex (U.S.A.) Inc. | Benzodioxanyl-hydroxyethylene-piperazinyl acetanilides which effect calcium entry and β-blockade |
| US4567264A (en) * | 1983-05-18 | 1986-01-28 | Syntex (U.S.A.) Inc. | Cardioselective aryloxy- and arylthio- hydroxypropylene-piperazinyl acetanilides which affect calcium entry |
| US4499100A (en) * | 1983-05-18 | 1985-02-12 | Syntex (U.S.A.) Inc. | Benzodioxanyl-hydroxyethyleneamino-piperidinyl acetanilides, ketones, esters and carbamates which effect immunity and calcium entry and β-blockade |
| US4997836A (en) * | 1988-11-11 | 1991-03-05 | Takeda Chemical Industries, Ltd. | Trisubstituted piperazine compounds, their production and use |
| US6514996B2 (en) | 1995-05-19 | 2003-02-04 | Kyowa Hakko Kogyo Co., Ltd. | Derivatives of benzofuran or benzodioxole |
| EP0943613A4 (en) * | 1996-11-19 | 2002-07-10 | Kyowa Hakko Kogyo Kk | Oxygenic heterocyclic compounds |
| WO2008144933A1 (en) | 2007-05-29 | 2008-12-04 | Université de Montréal | Cinnamoyl inhibitors of transglutaminase |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE865990A (fr) * | 1977-04-19 | 1978-10-16 | Delalande Sa | Nouvelles cinnamoyles piperazines et homopiperazines, leur procede de preparation et leur application en therapeutique |
-
1979
- 1979-08-03 FR FR7919990A patent/FR2462432A2/fr active Granted
-
1980
- 1980-07-18 CH CH551180A patent/CH646694A5/fr not_active IP Right Cessation
- 1980-07-21 CA CA000356675A patent/CA1155121A/en not_active Expired
- 1980-07-22 SE SE8005300A patent/SE8005300L/xx not_active Application Discontinuation
- 1980-07-28 GR GR62561A patent/GR68073B/el unknown
- 1980-07-30 DE DE19803028912 patent/DE3028912A1/de not_active Ceased
- 1980-08-01 GB GB8025200A patent/GB2057433B/en not_active Expired
- 1980-08-01 ES ES493931A patent/ES8107195A1/es not_active Expired
- 1980-08-01 LU LU82677A patent/LU82677A1/fr unknown
- 1980-08-01 BE BE0/201625A patent/BE884602R/fr not_active IP Right Cessation
- 1980-08-01 AU AU61003/80A patent/AU6100380A/en not_active Abandoned
- 1980-08-01 ZA ZA00804709A patent/ZA804709B/xx unknown
- 1980-08-01 JP JP10632080A patent/JPS5626885A/ja active Granted
- 1980-08-04 NL NL8004434A patent/NL8004434A/nl not_active Application Discontinuation
-
1981
- 1981-02-26 ES ES499814A patent/ES8301944A1/es not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE865990A (fr) * | 1977-04-19 | 1978-10-16 | Delalande Sa | Nouvelles cinnamoyles piperazines et homopiperazines, leur procede de preparation et leur application en therapeutique |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2507604A2 (fr) * | 1977-04-19 | 1982-12-17 | Delalande Sa | Nouvelles trimethoxy-3,4,5 cinnamoyle piperazines, leur procede de preparation et leur application en therapeutique |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA804709B (en) | 1981-10-28 |
| SE8005300L (sv) | 1981-02-04 |
| GB2057433A (en) | 1981-04-01 |
| JPS634827B2 (enrdf_load_stackoverflow) | 1988-02-01 |
| CA1155121A (en) | 1983-10-11 |
| ES499814A0 (es) | 1982-12-16 |
| JPS5626885A (en) | 1981-03-16 |
| AU6100380A (en) | 1981-02-05 |
| LU82677A1 (fr) | 1982-05-10 |
| ES493931A0 (es) | 1981-10-01 |
| ES8301944A1 (es) | 1982-12-16 |
| ES8107195A1 (es) | 1981-10-01 |
| FR2462432B2 (enrdf_load_stackoverflow) | 1983-05-27 |
| NL8004434A (nl) | 1981-02-05 |
| GR68073B (enrdf_load_stackoverflow) | 1981-10-29 |
| GB2057433B (en) | 1983-08-10 |
| CH646694A5 (fr) | 1984-12-14 |
| DE3028912A1 (de) | 1981-09-24 |
| BE884602R (fr) | 1981-02-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TP | Transmission of property |