FR2530245A1 - Nouveaux 1-(2-carbalkoxy 4-(thienyl-alkylamido)phenoxy) 3-amino 2-propanols, leur preparation et leurs applications en therapeutique - Google Patents
Nouveaux 1-(2-carbalkoxy 4-(thienyl-alkylamido)phenoxy) 3-amino 2-propanols, leur preparation et leurs applications en therapeutique Download PDFInfo
- Publication number
- FR2530245A1 FR2530245A1 FR8212499A FR8212499A FR2530245A1 FR 2530245 A1 FR2530245 A1 FR 2530245A1 FR 8212499 A FR8212499 A FR 8212499A FR 8212499 A FR8212499 A FR 8212499A FR 2530245 A1 FR2530245 A1 FR 2530245A1
- Authority
- FR
- France
- Prior art keywords
- sep
- formula
- phenoxy
- carbethoxy
- propanol
- 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
- 238000002360 preparation method Methods 0.000 title claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 title description 19
- 238000002560 therapeutic procedure Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 230000001882 diuretic effect Effects 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 claims description 7
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000002876 beta blocker Substances 0.000 abstract 1
- 229940097320 beta blocking agent Drugs 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 150000001408 amides Chemical class 0.000 description 13
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 150000002924 oxiranes Chemical class 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- 229960004592 isopropanol Drugs 0.000 description 5
- -1 1- [2-Carbethoxy-4- (3-thienylacetamido) phenoxy] 2,3-epoxy propene Chemical compound 0.000 description 4
- RNFDZDMIFOFNMC-UHFFFAOYSA-N 1-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(C)O RNFDZDMIFOFNMC-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 4
- AYNBYSNISOAOHW-UHFFFAOYSA-N 1-(tert-butylamino)propan-2-ol Chemical compound CC(O)CNC(C)(C)C AYNBYSNISOAOHW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 3
- 229940011051 isopropyl acetate Drugs 0.000 description 3
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- LYMWJSSXZZSVGC-UHFFFAOYSA-N ethyl 2-[2-hydroxy-3-(propan-2-ylamino)propoxy]-5-[(2-thiophen-3-ylacetyl)amino]benzoate Chemical compound C1=C(OCC(O)CNC(C)C)C(C(=O)OCC)=CC(NC(=O)CC2=CSC=C2)=C1 LYMWJSSXZZSVGC-UHFFFAOYSA-N 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- UUPZTFTUZUQRQT-UHFFFAOYSA-N 2-thiophen-2-ylacetamide Chemical compound NC(=O)CC1=CC=CS1 UUPZTFTUZUQRQT-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 0 C*NS(CC1C)(C=*[C@]1OC)=C Chemical compound C*NS(CC1C)(C=*[C@]1OC)=C 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- OTCCIMWXFLJLIA-UHFFFAOYSA-N N-acetyl-DL-aspartic acid Natural products CC(=O)NC(C(O)=O)CC(O)=O OTCCIMWXFLJLIA-UHFFFAOYSA-N 0.000 description 1
- OTCCIMWXFLJLIA-BYPYZUCNSA-N N-acetyl-L-aspartic acid Chemical compound CC(=O)N[C@H](C(O)=O)CC(O)=O OTCCIMWXFLJLIA-BYPYZUCNSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 238000007796 conventional method Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- AOUOIOUVNQVJDV-UHFFFAOYSA-N ethyl 2-(oxiran-2-ylmethoxy)-5-[(2-thiophen-2-ylacetyl)amino]benzoate Chemical compound C=1C=C(OCC2OC2)C(C(=O)OCC)=CC=1NC(=O)CC1=CC=CS1 AOUOIOUVNQVJDV-UHFFFAOYSA-N 0.000 description 1
- ZZPLGDOZCVZNNW-UHFFFAOYSA-N ethyl 2-hydroxy-5-[(2-thiophen-2-ylacetyl)amino]benzoate Chemical compound C1=C(O)C(C(=O)OCC)=CC(NC(=O)CC=2SC=CC=2)=C1 ZZPLGDOZCVZNNW-UHFFFAOYSA-N 0.000 description 1
- ZKFFZXDUSRQDLL-UHFFFAOYSA-N ethyl 2-hydroxy-5-[(2-thiophen-3-ylacetyl)amino]benzoate Chemical compound C1=C(O)C(C(=O)OCC)=CC(NC(=O)CC2=CSC=C2)=C1 ZKFFZXDUSRQDLL-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000006263 metalation reaction Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 231100000926 not very toxic Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000003451 thiazide diuretic agent Substances 0.000 description 1
- 229940124591 thiazide-type diuretic Drugs 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8212499A FR2530245A1 (fr) | 1982-07-16 | 1982-07-16 | Nouveaux 1-(2-carbalkoxy 4-(thienyl-alkylamido)phenoxy) 3-amino 2-propanols, leur preparation et leurs applications en therapeutique |
| IE1496/83A IE56108B1 (en) | 1982-07-16 | 1983-06-27 | 1-(2-carbalkoxy-4-(thienylcarboxamido)phenoxy)-3-amino 2-propanols,their preparation and applications thereof in therapeutics |
| ZA834797A ZA834797B (en) | 1982-07-16 | 1983-06-30 | New 1-(2-carbalkoxy-4-(thienyl-alkyl-amido)phenoxy)3-amino 2-propanols,their preparation and applications thereof in therapeutics |
| GR71869A GR79194B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-07-16 | 1983-07-05 | |
| AT83401450T ATE23335T1 (de) | 1982-07-16 | 1983-07-13 | 1-(2-carbalkoxy-4-(thienylalkylamido)phenoxy)-3 amino-2-propanole, ihre herstellung und ihre verwendungen in therapie. |
| EP83401450A EP0099822B1 (fr) | 1982-07-16 | 1983-07-13 | Nouveaux 1-(2-carbalkoxy 4-(thiénylalkylamido)phénoxy) 3-amino 2-propanols, leur préparation et leurs applications en thérapeutique |
| DE8383401450T DE3367389D1 (en) | 1982-07-16 | 1983-07-13 | 1-(2-carbalkoxy-4-(thienylalkylamido)phenoxy)-3-amino-2-propanols, their preparation and their uses in therapy |
| ES524103A ES8407485A1 (es) | 1982-07-16 | 1983-07-14 | Un procedimiento de preparacion de nuevos 1(2-carbalcoxi-4-(tienilalquilamido) fenoxi)3-amino 2-propanoles utilizables en terapeutica. |
| PT77031A PT77031B (fr) | 1982-07-16 | 1983-07-14 | Procede de preparation de nouveaux 1-<2-carbalcoxy 4-(thienylalkylamido)phenoxy>3-amino 2-propanols utilisables en therapeutique |
| CA000432423A CA1205478A (en) | 1982-07-16 | 1983-07-14 | 1-¬2-carbalkoxy 4-(thienyl-alkyl-amido)phenoxy| 3- amino 2-propanols, their preparation and applications thereof in therapeutics |
| AU16868/83A AU566089B2 (en) | 1982-07-16 | 1983-07-15 | N-phenyl thiophene (and thiophene methyl) carboxamide derivatives |
| DK326883A DK164552C (da) | 1982-07-16 | 1983-07-15 | Analogifremgangsmaade til fremstilling af 1-oe2-carbalkoxy-4-(thienylcarboxamido)-phenoxyaa-3-amino-2-propanoler eller syreadditionssalte deraf |
| JP58128050A JPS5973582A (ja) | 1982-07-16 | 1983-07-15 | チオフエン系化合物およびその製造方法並びに医薬 |
| US06/814,077 US4668801A (en) | 1982-07-16 | 1985-12-23 | 1-(2-carboalkoxy 4-(thienyl-alkyl-amido) phenyoxyl 30 amino 20 propanols, their preparation and applications thereof in therapeutics |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8212499A FR2530245A1 (fr) | 1982-07-16 | 1982-07-16 | Nouveaux 1-(2-carbalkoxy 4-(thienyl-alkylamido)phenoxy) 3-amino 2-propanols, leur preparation et leurs applications en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2530245A1 true FR2530245A1 (fr) | 1984-01-20 |
| FR2530245B1 FR2530245B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-04-19 |
Family
ID=9276043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8212499A Granted FR2530245A1 (fr) | 1982-07-16 | 1982-07-16 | Nouveaux 1-(2-carbalkoxy 4-(thienyl-alkylamido)phenoxy) 3-amino 2-propanols, leur preparation et leurs applications en therapeutique |
Country Status (3)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5268389A (en) * | 1989-10-16 | 1993-12-07 | Uniroyal Chemical Company, Inc. | Thiocarboxylate ester compounds compositions containing the same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1543689A (fr) * | 1966-11-03 | 1968-10-25 | Ici Ltd | Procédé de fabrication de nouvelles alcanolamines et de leurs dérivés |
| FR2291741A1 (fr) * | 1974-11-20 | 1976-06-18 | Pharmacia As | Nouvelles phenylethanolamines |
| FR2458548A1 (fr) * | 1979-06-12 | 1981-01-02 | Nattermann A & Cie | Anilides d'acides furranne-2-carboxyliques substitues, leur preparation et leurs utilisations therapeutiques |
-
1982
- 1982-07-16 FR FR8212499A patent/FR2530245A1/fr active Granted
-
1983
- 1983-06-30 ZA ZA834797A patent/ZA834797B/xx unknown
- 1983-07-15 JP JP58128050A patent/JPS5973582A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1543689A (fr) * | 1966-11-03 | 1968-10-25 | Ici Ltd | Procédé de fabrication de nouvelles alcanolamines et de leurs dérivés |
| FR2291741A1 (fr) * | 1974-11-20 | 1976-06-18 | Pharmacia As | Nouvelles phenylethanolamines |
| FR2458548A1 (fr) * | 1979-06-12 | 1981-01-02 | Nattermann A & Cie | Anilides d'acides furranne-2-carboxyliques substitues, leur preparation et leurs utilisations therapeutiques |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA834797B (en) | 1984-03-28 |
| JPH024225B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-01-26 |
| JPS5973582A (ja) | 1984-04-25 |
| FR2530245B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-04-19 |
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