HU180644B - Process for preparing 1-/2-propynyl-oxy-/2-amino-3-propanol esters - Google Patents
Process for preparing 1-/2-propynyl-oxy-/2-amino-3-propanol esters Download PDFInfo
- Publication number
- HU180644B HU180644B HU80803126A HU312680A HU180644B HU 180644 B HU180644 B HU 180644B HU 80803126 A HU80803126 A HU 80803126A HU 312680 A HU312680 A HU 312680A HU 180644 B HU180644 B HU 180644B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- phenyl
- compound
- radical
- compounds
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- -1 alkyl radical Chemical class 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000003444 phase transfer catalyst Substances 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 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 208000020446 Cardiac disease Diseases 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- 125000005905 mesyloxy group Chemical group 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 abstract description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical group [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 6
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- KSLSOBUAIFEGLT-UHFFFAOYSA-N 2-phenylbut-3-yn-2-ol Chemical compound C#CC(O)(C)C1=CC=CC=C1 KSLSOBUAIFEGLT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 208000001871 Tachycardia Diseases 0.000 description 2
- 230000004872 arterial blood pressure Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 210000005240 left ventricle Anatomy 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000006794 tachycardia Effects 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- BPWQZVXIARGHIS-UHFFFAOYSA-N 1-(1-ethynylcyclohexyl)oxy-3-pyrrolidin-1-ylpropan-2-ol Chemical compound C1CCCN1CC(O)COC1(C#C)CCCCC1 BPWQZVXIARGHIS-UHFFFAOYSA-N 0.000 description 1
- AUGPFUKHHHPALE-UHFFFAOYSA-N 1-(2-chloro-3-phenoxypropyl)pyrrolidine Chemical compound C1CCCN1CC(Cl)COC1=CC=CC=C1 AUGPFUKHHHPALE-UHFFFAOYSA-N 0.000 description 1
- QWBRUZYLJQZHGC-UHFFFAOYSA-N 1-[1-(1-ethynylcyclohexyl)oxy-3-(2-phenylbut-3-yn-2-yloxy)propan-2-yl]pyrrolidine Chemical compound C=1C=CC=CC=1C(C)(C#C)OCC(N1CCCC1)COC1(C#C)CCCCC1 QWBRUZYLJQZHGC-UHFFFAOYSA-N 0.000 description 1
- MOFBXBIYUVXLFH-UHFFFAOYSA-N 1-[1-phenoxy-3-(2-phenylbut-3-yn-2-yloxy)propan-2-yl]pyrrolidine Chemical compound C=1C=CC=CC=1C(C)(C#C)OCC(N1CCCC1)COC1=CC=CC=C1 MOFBXBIYUVXLFH-UHFFFAOYSA-N 0.000 description 1
- HOUFSDUTCAUBHL-UHFFFAOYSA-N 1-[2-chloro-3-(2-methylpropoxy)propyl]pyrrolidine Chemical compound CC(C)COCC(Cl)CN1CCCC1 HOUFSDUTCAUBHL-UHFFFAOYSA-N 0.000 description 1
- CWLUFVAFWWNXJZ-UHFFFAOYSA-N 1-hydroxypyrrolidine Chemical compound ON1CCCC1 CWLUFVAFWWNXJZ-UHFFFAOYSA-N 0.000 description 1
- UTISCLIDFORRJP-UHFFFAOYSA-N 1-prop-1-ynylcyclohexan-1-ol Chemical compound CC#CC1(O)CCCCC1 UTISCLIDFORRJP-UHFFFAOYSA-N 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical group CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 description 1
- QCHHRTIQDOHXPB-UHFFFAOYSA-N 3-naphthalen-1-yloxy-2-(propan-2-ylamino)propan-1-ol Chemical compound C1=CC=C2C(OCC(CO)NC(C)C)=CC=CC2=C1 QCHHRTIQDOHXPB-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
- WJYHOGKFWPZPJY-UHFFFAOYSA-N CS(=O)(=O)OC(CN1CCCC1)COC2(CCCCC2)C#C Chemical compound CS(=O)(=O)OC(CN1CCCC1)COC2(CCCCC2)C#C WJYHOGKFWPZPJY-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010049694 Left Ventricular Dysfunction Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- OJYGBLRPYBAHRT-IPQSZEQASA-N chloralose Chemical compound O1[C@H](C(Cl)(Cl)Cl)O[C@@H]2[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]21 OJYGBLRPYBAHRT-IPQSZEQASA-N 0.000 description 1
- 229950009941 chloralose Drugs 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000010247 heart contraction Effects 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229960003712 propranolol Drugs 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 208000019553 vascular disease Diseases 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
- C07D295/08—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 bound oxygen or sulfur atoms
- C07D295/084—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7932008A FR2472567A1 (fr) | 1979-12-28 | 1979-12-28 | Ethers de 1- (2-propynyloxy)-2-amino-3-propanol, leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU180644B true HU180644B (en) | 1983-03-28 |
Family
ID=9233299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU80803126A HU180644B (en) | 1979-12-28 | 1980-12-28 | Process for preparing 1-/2-propynyl-oxy-/2-amino-3-propanol esters |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4430332A (en, 2012) |
| EP (1) | EP0031771B1 (en, 2012) |
| JP (1) | JPS56103140A (en, 2012) |
| AT (1) | ATE2786T1 (en, 2012) |
| AU (1) | AU531550B2 (en, 2012) |
| CA (1) | CA1142926A (en, 2012) |
| DE (1) | DE3062375D1 (en, 2012) |
| DK (1) | DK155519C (en, 2012) |
| ES (1) | ES498150A0 (en, 2012) |
| FI (1) | FI71137C (en, 2012) |
| FR (1) | FR2472567A1 (en, 2012) |
| GR (1) | GR72514B (en, 2012) |
| HU (1) | HU180644B (en, 2012) |
| IE (1) | IE50639B1 (en, 2012) |
| PT (1) | PT72244B (en, 2012) |
| YU (1) | YU327980A (en, 2012) |
| ZA (1) | ZA807711B (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3363743D1 (en) * | 1982-07-22 | 1986-07-03 | Pfizer Ltd | Dihydropyridine anti-ischaemic and antihypertensive agents |
Family Cites Families (4)
| 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 |
| FR2173869B1 (en, 2012) * | 1972-04-13 | 1975-12-26 | Cerm Cent Europ Rech Mauvernay | |
| US4060613A (en) | 1976-05-19 | 1977-11-29 | Ayerst Mckenna And Harrison Ltd. | 3-Aryloxy-2(4-loweralkyl-1-piperazinyl)propanols, their alkylethers, and use thereof |
| CA1085841A (en) * | 1976-05-19 | 1980-09-16 | Jean-Marie Ferland | Aryloxy proplamines, their preparation and use thereof |
-
1979
- 1979-12-28 FR FR7932008A patent/FR2472567A1/fr active Granted
-
1980
- 1980-12-09 ZA ZA00807711A patent/ZA807711B/xx unknown
- 1980-12-15 AU AU65394/80A patent/AU531550B2/en not_active Ceased
- 1980-12-19 EP EP80401829A patent/EP0031771B1/fr not_active Expired
- 1980-12-19 AT AT80401829T patent/ATE2786T1/de not_active IP Right Cessation
- 1980-12-19 DK DK544480A patent/DK155519C/da not_active IP Right Cessation
- 1980-12-19 US US06/218,176 patent/US4430332A/en not_active Expired - Fee Related
- 1980-12-19 PT PT72244A patent/PT72244B/pt not_active IP Right Cessation
- 1980-12-19 DE DE8080401829T patent/DE3062375D1/de not_active Expired
- 1980-12-22 FI FI803996A patent/FI71137C/fi not_active IP Right Cessation
- 1980-12-23 CA CA000367499A patent/CA1142926A/en not_active Expired
- 1980-12-23 IE IE2727/80A patent/IE50639B1/en not_active IP Right Cessation
- 1980-12-24 GR GR63760A patent/GR72514B/el unknown
- 1980-12-24 ES ES498150A patent/ES498150A0/es active Granted
- 1980-12-25 YU YU03279/80A patent/YU327980A/xx unknown
- 1980-12-26 JP JP18932180A patent/JPS56103140A/ja active Granted
- 1980-12-28 HU HU80803126A patent/HU180644B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK544480A (da) | 1981-06-29 |
| DK155519C (da) | 1989-09-04 |
| JPS56103140A (en) | 1981-08-18 |
| AU531550B2 (en) | 1983-08-25 |
| FI803996L (fi) | 1981-06-29 |
| PT72244B (en) | 1981-11-05 |
| IE50639B1 (en) | 1986-05-28 |
| CA1142926A (en) | 1983-03-15 |
| DE3062375D1 (en) | 1983-04-21 |
| DK155519B (da) | 1989-04-17 |
| EP0031771A1 (fr) | 1981-07-08 |
| FR2472567A1 (fr) | 1981-07-03 |
| GR72514B (en, 2012) | 1983-11-16 |
| ATE2786T1 (de) | 1983-04-15 |
| FR2472567B1 (en, 2012) | 1983-03-11 |
| AU6539480A (en) | 1981-07-02 |
| EP0031771B1 (fr) | 1983-03-16 |
| ES8203869A1 (es) | 1982-04-16 |
| US4430332A (en) | 1984-02-07 |
| ES498150A0 (es) | 1982-04-16 |
| PT72244A (en) | 1981-01-01 |
| FI71137C (fi) | 1986-11-24 |
| FI71137B (fi) | 1986-08-14 |
| IE802727L (en) | 1981-06-28 |
| JPS6313426B2 (en, 2012) | 1988-03-25 |
| ZA807711B (en) | 1981-12-30 |
| YU327980A (en) | 1983-02-28 |
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