FR2472567A1 - Ethers de 1- (2-propynyloxy)-2-amino-3-propanol, leur preparation et leur application en therapeutique - Google Patents
Ethers de 1- (2-propynyloxy)-2-amino-3-propanol, leur preparation et leur application en therapeutique Download PDFInfo
- Publication number
- FR2472567A1 FR2472567A1 FR7932008A FR7932008A FR2472567A1 FR 2472567 A1 FR2472567 A1 FR 2472567A1 FR 7932008 A FR7932008 A FR 7932008A FR 7932008 A FR7932008 A FR 7932008A FR 2472567 A1 FR2472567 A1 FR 2472567A1
- Authority
- FR
- France
- Prior art keywords
- radical
- phenyl
- pyrrolidinyl
- compounds
- lower alkyl
- 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.)
- Granted
Links
- -1 1- (2-PROPYNYLOXY) -2-AMINO-3-PROPANOL ETHERS Chemical class 0.000 title claims abstract description 30
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 229910052799 carbon Inorganic materials 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 4
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 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
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- BFXRCMJRKTUNIQ-UHFFFAOYSA-N 1-[1-(2-methylpropoxy)-3-(2-phenylbut-3-yn-2-yloxy)propan-2-yl]pyrrolidine Chemical compound C1CCCN1C(COCC(C)C)COC(C)(C#C)C1=CC=CC=C1 BFXRCMJRKTUNIQ-UHFFFAOYSA-N 0.000 claims description 2
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical compound CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 claims description 2
- 208000020446 Cardiac disease Diseases 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 208000019622 heart disease Diseases 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 238000006276 transfer reaction Methods 0.000 claims description 2
- FITWYAUFKJXWPL-UHFFFAOYSA-N 1-[1-(2-methylpropoxy)-3-(1-prop-1-ynylcyclohexyl)oxypropan-2-yl]pyrrolidine Chemical compound C1CCCN1C(COCC(C)C)COC1(C#CC)CCCCC1 FITWYAUFKJXWPL-UHFFFAOYSA-N 0.000 claims 1
- OORYZQGIBKAMPQ-UHFFFAOYSA-N 2-amino-3-prop-2-ynoxypropan-1-ol Chemical compound OCC(N)COCC#C OORYZQGIBKAMPQ-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 229940105847 calamine Drugs 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910052864 hemimorphite Inorganic materials 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 235000014692 zinc oxide Nutrition 0.000 claims 1
- 239000011787 zinc oxide Substances 0.000 claims 1
- CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-UHFFFAOYSA-N 0.000 claims 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000047 product Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
- 238000003756 stirring Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 208000001871 Tachycardia Diseases 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- PMZSDQGYELHPDH-UHFFFAOYSA-N but-3-yn-2-ylbenzene Chemical compound C#CC(C)C1=CC=CC=C1 PMZSDQGYELHPDH-UHFFFAOYSA-N 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
- 101150035983 str1 gene Proteins 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000006794 tachycardia Effects 0.000 description 2
- 238000012546 transfer 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
- 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
- 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
- UALAADHAOONBKD-UHFFFAOYSA-N 1-ethynyl-1-propoxycyclohexane Chemical compound CCCOC1(C#C)CCCCC1 UALAADHAOONBKD-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- YGZQJYIITOMTMD-UHFFFAOYSA-N 1-propoxybutane Chemical compound CCCCOCCC YGZQJYIITOMTMD-UHFFFAOYSA-N 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 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 1
- ZLTRGJLBUGKEDQ-UHFFFAOYSA-N 3-amino-2-chloropropan-1-ol Chemical class NCC(Cl)CO ZLTRGJLBUGKEDQ-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 230000000747 cardiac effect Effects 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
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 230000002650 habitual effect Effects 0.000 description 1
- 230000010247 heart contraction Effects 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003601 intercostal effect Effects 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000020075 ouzo Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- DSNYFFJTZPIKFZ-UHFFFAOYSA-N propoxybenzene Chemical compound CCCOC1=CC=CC=C1 DSNYFFJTZPIKFZ-UHFFFAOYSA-N 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
- 230000009257 reactivity Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000002861 ventricular Effects 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)
Priority Applications (17)
| 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 |
| ZA00807711A ZA807711B (en) | 1979-12-28 | 1980-12-09 | Ethers of 1-(2-propynyloxy)-2-amino-3-propanol |
| AU65394/80A AU531550B2 (en) | 1979-12-28 | 1980-12-15 | Ethers of 1-(2-propynyloxy)-2-amino-3-propanol |
| AT80401829T ATE2786T1 (de) | 1979-12-28 | 1980-12-19 | 1-(2-propynyloxy)-2-amino-3-propanol-aether, ihre herstellung und sie enthaltende pharmazeutische zusammensetzung. |
| EP80401829A EP0031771B1 (fr) | 1979-12-28 | 1980-12-19 | Ethers de 1-(2-propynyloxy)-2-amino-3-propanol, leur préparation et une composition pharmaceutique les contenant |
| DK544480A DK155519C (da) | 1979-12-28 | 1980-12-19 | Analogifremgangsmaade til fremstilling af ethere af 1-(2-propynyloxy)-2-amino-3-propanoler |
| DE8080401829T DE3062375D1 (en) | 1979-12-28 | 1980-12-19 | 1-(2-propynyloxy)-2-amino-3-propanol ethers, their preparation and pharmaceutical composition containing them |
| US06/218,176 US4430332A (en) | 1979-12-28 | 1980-12-19 | Ethers of 1-(2-propynyloxy)-2-amino-3-propanol |
| PT72244A PT72244B (en) | 1979-12-28 | 1980-12-19 | Ethers of 1-(2-propynyloxy)-2-amino-3-propanol |
| FI803996A FI71137C (fi) | 1979-12-28 | 1980-12-22 | Foerfarande foer framstaellning av nya cardiovasculaert aktiva1-(2-propynyloxi)-2-amino-3-propanoleterderivat |
| IE2727/80A IE50639B1 (en) | 1979-12-28 | 1980-12-23 | Ethers of 1-(2-propynyloxy)-2-amino-3-propanol |
| CA000367499A CA1142926A (en) | 1979-12-28 | 1980-12-23 | Ethers of 1-(2-propynyloxy) 2-amino-3-propanol |
| GR63760A GR72514B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-12-28 | 1980-12-24 | |
| ES498150A ES8203869A1 (es) | 1979-12-28 | 1980-12-24 | Un procedimiento para la preparacion de nuevos eteres de 1-(2-propiniloxi)-2-amino-3-propanol. |
| YU03279/80A YU327980A (en) | 1979-12-28 | 1980-12-25 | Process for preparing new 1-(2-propinyloxy)-2-amino-3-propanol ethers |
| JP18932180A JPS56103140A (en) | 1979-12-28 | 1980-12-26 | Novel ethers* manufacture and medicinal composition containing them |
| HU80803126A HU180644B (en) | 1979-12-28 | 1980-12-28 | Process for preparing 1-/2-propynyl-oxy-/2-amino-3-propanol esters |
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 (2)
| Publication Number | Publication Date |
|---|---|
| FR2472567A1 true FR2472567A1 (fr) | 1981-07-03 |
| FR2472567B1 FR2472567B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-03-11 |
Family
ID=9233299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7932008A Granted FR2472567A1 (fr) | 1979-12-28 | 1979-12-28 | Ethers de 1- (2-propynyloxy)-2-amino-3-propanol, leur preparation et leur application en therapeutique |
Country Status (17)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0100189B1 (en) * | 1982-07-22 | 1986-05-28 | Pfizer Limited | Dihydropyridine anti-ischaemic and antihypertensive agents |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2173869A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-04-13 | 1973-10-12 | Cerm Cent Europ Rech Mauvernay |
Family Cites Families (3)
| 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 |
| 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 DE DE8080401829T patent/DE3062375D1/de 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 PT PT72244A patent/PT72244B/pt not_active IP Right Cessation
- 1980-12-19 US US06/218,176 patent/US4430332A/en not_active Expired - Fee Related
- 1980-12-19 EP EP80401829A patent/EP0031771B1/fr 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/ES8203869A1/es not_active Expired
- 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
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2173869A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-04-13 | 1973-10-12 | Cerm Cent Europ Rech Mauvernay |
Also Published As
| Publication number | Publication date |
|---|---|
| GR72514B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-11-16 |
| EP0031771A1 (fr) | 1981-07-08 |
| AU531550B2 (en) | 1983-08-25 |
| FR2472567B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-03-11 |
| FI71137C (fi) | 1986-11-24 |
| DE3062375D1 (en) | 1983-04-21 |
| YU327980A (en) | 1983-02-28 |
| CA1142926A (en) | 1983-03-15 |
| JPS56103140A (en) | 1981-08-18 |
| US4430332A (en) | 1984-02-07 |
| ZA807711B (en) | 1981-12-30 |
| DK544480A (da) | 1981-06-29 |
| DK155519B (da) | 1989-04-17 |
| HU180644B (en) | 1983-03-28 |
| AU6539480A (en) | 1981-07-02 |
| PT72244B (en) | 1981-11-05 |
| IE50639B1 (en) | 1986-05-28 |
| IE802727L (en) | 1981-06-28 |
| FI71137B (fi) | 1986-08-14 |
| PT72244A (en) | 1981-01-01 |
| ES498150A0 (es) | 1982-04-16 |
| FI803996L (fi) | 1981-06-29 |
| JPS6313426B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-03-25 |
| DK155519C (da) | 1989-09-04 |
| ATE2786T1 (de) | 1983-04-15 |
| EP0031771B1 (fr) | 1983-03-16 |
| ES8203869A1 (es) | 1982-04-16 |
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