GB1595031A - 3-isobutoxy-2-pyrrolidino-n-phenyl-n-benzyl propylamine and its salts - Google Patents
3-isobutoxy-2-pyrrolidino-n-phenyl-n-benzyl propylamine and its salts Download PDFInfo
- Publication number
- GB1595031A GB1595031A GB1506/78A GB150678A GB1595031A GB 1595031 A GB1595031 A GB 1595031A GB 1506/78 A GB1506/78 A GB 1506/78A GB 150678 A GB150678 A GB 150678A GB 1595031 A GB1595031 A GB 1595031A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- product
- pyrrolidino
- isobutoxy
- formula
- 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
- 150000003839 salts Chemical class 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 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 claims description 5
- 150000001408 amides Chemical group 0.000 claims description 5
- UIEATEWHFDRYRU-UHFFFAOYSA-N bepridil Chemical compound C1CCCN1C(COCC(C)C)CN(C=1C=CC=CC=1)CC1=CC=CC=C1 UIEATEWHFDRYRU-UHFFFAOYSA-N 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- ZMYAKSMZTVWUJB-UHFFFAOYSA-N 2,3-dibromopropanoic acid Chemical compound OC(=O)C(Br)CBr ZMYAKSMZTVWUJB-UHFFFAOYSA-N 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 150000004682 monohydrates Chemical class 0.000 claims description 4
- UDWPFNBMTQONIF-UHFFFAOYSA-L magnesium N-benzylaniline dibromide Chemical compound [Br-].[Mg+2].C(C1=CC=CC=C1)NC1=CC=CC=C1.[Br-] UDWPFNBMTQONIF-UHFFFAOYSA-L 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- BXXJTKRRXACUTI-UHFFFAOYSA-N 3-(2-methylpropoxy)-2-pyrrolidin-1-ylpropanoic acid Chemical compound C(C(C)C)OCC(C(=O)O)N1CCCC1 BXXJTKRRXACUTI-UHFFFAOYSA-N 0.000 claims description 2
- 206010002383 Angina Pectoris Diseases 0.000 abstract description 5
- 238000009835 boiling Methods 0.000 abstract description 2
- 230000002526 effect on cardiovascular system Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ITPDYQOUSLNIHG-UHFFFAOYSA-N Amiodarone hydrochloride Chemical compound [Cl-].CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCC[NH+](CC)CC)C(I)=C1 ITPDYQOUSLNIHG-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 229960005260 amiodarone Drugs 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- -1 2,3-dibromopropionic acid ester Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 208000009079 Bronchial Spasm Diseases 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 210000003748 coronary sinus Anatomy 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 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
- 239000012074 organic phase Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- QVHNPERSEFABEH-UHFFFAOYSA-N 2,2-dibromopropanoic acid Chemical compound CC(Br)(Br)C(O)=O QVHNPERSEFABEH-UHFFFAOYSA-N 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-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
- 238000000692 Student's t-test Methods 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000004004 anti-anginal agent Substances 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000003205 diastolic effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002996 emotional effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- WJZNJZWXOFGUFC-UHFFFAOYSA-N n-benzyl-n-propylaniline Chemical compound C=1C=CC=CC=1N(CCC)CC1=CC=CC=C1 WJZNJZWXOFGUFC-UHFFFAOYSA-N 0.000 description 1
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 1
- 230000010412 perfusion 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
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- DURULFYMVIFBIR-UHFFFAOYSA-N practolol Chemical compound CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1 DURULFYMVIFBIR-UHFFFAOYSA-N 0.000 description 1
- 229960001749 practolol Drugs 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 102220042372 rs201824641 Human genes 0.000 description 1
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical class [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 230000000213 tachycardiac effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229940100445 wheat starch Drugs 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
- C07D295/12—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 or doubly bound nitrogen atoms
- C07D295/125—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen 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
- 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
-
- 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
- C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7702058A FR2378024A1 (fr) | 1977-01-25 | 1977-01-25 | Nouvelle propylamine substituee, obtention et application |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1595031A true GB1595031A (en) | 1981-08-05 |
Family
ID=9185890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1506/78A Expired GB1595031A (en) | 1977-01-25 | 1978-01-13 | 3-isobutoxy-2-pyrrolidino-n-phenyl-n-benzyl propylamine and its salts |
Country Status (12)
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0096720A4 (en) * | 1981-12-28 | 1984-05-29 | Carter Wallace | Process for the preparation of B-[(2-methylpropoxy)-methyl]-N-phenyl-N-(phenylmethyl)-1-pyrrolidineethanamine. |
| US4555514A (en) * | 1984-01-18 | 1985-11-26 | Riom Laboratoires C.E.R.M. "Rl-Cerm" S.A. | 3-Alkoxy-2-(N-pyrolidino)-N-pyridyl-N-furyl(or thienyl) methyl-pyropyl amines useful as calcium antagonists |
| AU568704B2 (en) * | 1983-11-11 | 1988-01-07 | Akzo N.V. | Ether of n-propanolamine derivative |
| AU568694B2 (en) * | 1983-11-11 | 1988-01-07 | Akzo N.V. | N-benzyl-n-phenyl-b-pyrrolidinyl-f-isobutoxy-propylamine |
| AU569326B2 (en) * | 1983-09-27 | 1988-01-28 | Riom Laboratoires C.E.R.M. "Rl-Cerm" S.A. | 2-(n-pyrrolidino)-3-isobutoxy-n-substituted phenyl-n-benzyl-propylamines |
| US4762834A (en) * | 1984-01-18 | 1988-08-09 | Riom Laboratoires C.E.R.M. "Rl-Cerm", S.A. | 3-alkoxy-2-(N-pyrrolidino)-N-pyrimidinyl- or -N-pyrazinolpropylamines useful for treatment of cardiovascular disorders |
| EP0330910A1 (en) * | 1988-02-16 | 1989-09-06 | Kowa Company, Ltd. | Propane derivatives |
| WO2016098128A1 (en) * | 2014-12-16 | 2016-06-23 | Council Of Scientific & Industrial Research | Process for the preparation of bepridil |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2558159B1 (fr) * | 1984-01-18 | 1986-06-13 | Cerm Cent Europ Rech Mauvernay | 3-alkoxy 2-(n-pyrrolidino)-n-pyridyl-n-arylmethyl-propylamines, leur preparation et leur application en therapeutique |
| DE3726633A1 (de) * | 1987-08-11 | 1989-02-23 | Boehringer Mannheim Gmbh | Neue 1,2-diamino-verbindungen, verfahren zu ihrer herstellung sowie arzneimittel, die diese verbindungen enthalten |
| DE3726632A1 (de) * | 1987-08-11 | 1989-05-18 | Boehringer Mannheim Gmbh | 1,2-diamino-verbindungen, verfahren zu ihrer herstellung sowie arzneimittel, die diese verbindungen enthalten |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795735A (fr) * | 1972-03-06 | 1973-06-18 | Cerm Cent Europ Rech Mauvernay | Nouvelles ethylenediamines substituees a activite cardiovasculaire |
-
1977
- 1977-01-25 FR FR7702058A patent/FR2378024A1/fr active Granted
- 1977-10-03 JP JP11797777A patent/JPS5392764A/ja active Granted
-
1978
- 1978-01-11 CH CH27378A patent/CH628889A5/fr not_active IP Right Cessation
- 1978-01-13 GB GB1506/78A patent/GB1595031A/en not_active Expired
- 1978-01-16 IL IL53816A patent/IL53816A0/xx not_active IP Right Cessation
- 1978-01-20 PT PT67556A patent/PT67556B/pt unknown
- 1978-01-20 NL NLAANVRAGE7800753,A patent/NL189258C/xx not_active IP Right Cessation
- 1978-01-21 ES ES466237A patent/ES466237A1/es not_active Expired
- 1978-01-23 BE BE184554A patent/BE863214A/xx not_active IP Right Cessation
- 1978-01-23 AU AU32660/78A patent/AU516479B2/en not_active Expired
- 1978-01-24 ZA ZA00780426A patent/ZA78426B/xx unknown
- 1978-01-24 DE DE2802864A patent/DE2802864C2/de not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0096720A4 (en) * | 1981-12-28 | 1984-05-29 | Carter Wallace | Process for the preparation of B-[(2-methylpropoxy)-methyl]-N-phenyl-N-(phenylmethyl)-1-pyrrolidineethanamine. |
| AU569326B2 (en) * | 1983-09-27 | 1988-01-28 | Riom Laboratoires C.E.R.M. "Rl-Cerm" S.A. | 2-(n-pyrrolidino)-3-isobutoxy-n-substituted phenyl-n-benzyl-propylamines |
| AU568704B2 (en) * | 1983-11-11 | 1988-01-07 | Akzo N.V. | Ether of n-propanolamine derivative |
| AU568694B2 (en) * | 1983-11-11 | 1988-01-07 | Akzo N.V. | N-benzyl-n-phenyl-b-pyrrolidinyl-f-isobutoxy-propylamine |
| US4555514A (en) * | 1984-01-18 | 1985-11-26 | Riom Laboratoires C.E.R.M. "Rl-Cerm" S.A. | 3-Alkoxy-2-(N-pyrolidino)-N-pyridyl-N-furyl(or thienyl) methyl-pyropyl amines useful as calcium antagonists |
| US4762834A (en) * | 1984-01-18 | 1988-08-09 | Riom Laboratoires C.E.R.M. "Rl-Cerm", S.A. | 3-alkoxy-2-(N-pyrrolidino)-N-pyrimidinyl- or -N-pyrazinolpropylamines useful for treatment of cardiovascular disorders |
| EP0330910A1 (en) * | 1988-02-16 | 1989-09-06 | Kowa Company, Ltd. | Propane derivatives |
| WO2016098128A1 (en) * | 2014-12-16 | 2016-06-23 | Council Of Scientific & Industrial Research | Process for the preparation of bepridil |
Also Published As
| Publication number | Publication date |
|---|---|
| CH628889A5 (en) | 1982-03-31 |
| ES466237A1 (es) | 1978-10-16 |
| AU516479B2 (en) | 1981-06-04 |
| AU3266078A (en) | 1979-08-02 |
| DE2802864A1 (de) | 1978-07-27 |
| NL189258C (nl) | 1993-02-16 |
| JPS5392764A (en) | 1978-08-15 |
| BE863214A (fr) | 1978-07-24 |
| PT67556A (fr) | 1978-02-01 |
| IL53816A0 (en) | 1978-04-30 |
| NL189258B (nl) | 1992-09-16 |
| JPS5429493B2 (enrdf_load_stackoverflow) | 1979-09-25 |
| FR2378024B1 (enrdf_load_stackoverflow) | 1979-05-11 |
| PT67556B (fr) | 1979-06-18 |
| DE2802864C2 (de) | 1982-12-09 |
| NL7800753A (nl) | 1978-07-27 |
| ZA78426B (en) | 1979-01-31 |
| FR2378024A1 (fr) | 1978-08-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19980112 |