FR2475546A1 - Phenoxyisobutyrates de moroxydine et medicaments les contenant - Google Patents
Phenoxyisobutyrates de moroxydine et medicaments les contenant Download PDFInfo
- Publication number
- FR2475546A1 FR2475546A1 FR8002927A FR8002927A FR2475546A1 FR 2475546 A1 FR2475546 A1 FR 2475546A1 FR 8002927 A FR8002927 A FR 8002927A FR 8002927 A FR8002927 A FR 8002927A FR 2475546 A1 FR2475546 A1 FR 2475546A1
- Authority
- FR
- France
- Prior art keywords
- sep
- moroxydine
- salt
- iii
- clofibrate
- 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
- 229960005389 moroxydine Drugs 0.000 title claims abstract description 23
- KJHOZAZQWVKILO-UHFFFAOYSA-N N-(diaminomethylidene)-4-morpholinecarboximidamide Chemical compound NC(N)=NC(=N)N1CCOCC1 KJHOZAZQWVKILO-UHFFFAOYSA-N 0.000 title claims abstract description 21
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 title claims description 13
- 229960001214 clofibrate Drugs 0.000 title claims description 13
- 230000000879 anti-atherosclerotic effect Effects 0.000 title description 2
- UYZDMKTZZHEOAM-UHFFFAOYSA-N 3-chloro-2-methyl-4-oxo-2-phenoxy-4-phenylbutanoic acid Chemical compound C=1C=CC=CC=1C(=O)C(Cl)C(C(O)=O)(C)OC1=CC=CC=C1 UYZDMKTZZHEOAM-UHFFFAOYSA-N 0.000 title 1
- 230000002785 anti-thrombosis Effects 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- -1 Moroxydine phenoxyisobutyrates Chemical class 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 239000003814 drug Substances 0.000 claims abstract description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000003456 ion exchange resin Substances 0.000 claims abstract 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract 2
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- WRSHXWJSBPKQIS-UHFFFAOYSA-N phenyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC1=CC=CC=C1 WRSHXWJSBPKQIS-UHFFFAOYSA-N 0.000 claims 2
- LFHCHPXROVDFHT-UHFFFAOYSA-N 2-methyl-3-phenoxypropanoic acid Chemical compound OC(=O)C(C)COC1=CC=CC=C1 LFHCHPXROVDFHT-UHFFFAOYSA-N 0.000 claims 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 5
- 102000008946 Fibrinogen Human genes 0.000 abstract description 4
- 108010049003 Fibrinogen Proteins 0.000 abstract description 4
- 229940012952 fibrinogen Drugs 0.000 abstract description 4
- 230000002218 hypoglycaemic effect Effects 0.000 abstract description 3
- 229910052700 potassium Inorganic materials 0.000 abstract description 2
- 229910052708 sodium Inorganic materials 0.000 abstract description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 abstract description 2
- 201000001320 Atherosclerosis Diseases 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 208000007536 Thrombosis Diseases 0.000 abstract 1
- 239000008280 blood Substances 0.000 abstract 1
- 210000004369 blood Anatomy 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 231100000053 low toxicity Toxicity 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- 239000000047 product Substances 0.000 description 7
- 241000700159 Rattus Species 0.000 description 5
- 235000012000 cholesterol Nutrition 0.000 description 4
- 239000003315 2-(4-chlorophenoxy)-2-methylpropanoic acid Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 description 3
- 229950008441 clofibric acid Drugs 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 208000010201 Exanthema Diseases 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 201000005884 exanthem Diseases 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 235000021590 normal diet Nutrition 0.000 description 2
- 206010037844 rash Diseases 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- BITDLWAQPKSXTF-UHFFFAOYSA-M 1-[(3-nitrophenyl)methoxymethyl]pyridin-1-ium;chloride Chemical compound [Cl-].[O-][N+](=O)C1=CC=CC(COC[N+]=2C=CC=CC=2)=C1 BITDLWAQPKSXTF-UHFFFAOYSA-M 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010019851 Hepatotoxicity Diseases 0.000 description 1
- 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 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102000003929 Transaminases Human genes 0.000 description 1
- 108090000340 Transaminases Proteins 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 206010047249 Venous thrombosis Diseases 0.000 description 1
- RKFMOTBTFHXWCM-UHFFFAOYSA-M [AlH2]O Chemical compound [AlH2]O RKFMOTBTFHXWCM-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000002744 anti-aggregatory effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 230000003143 atherosclerotic effect Effects 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RSMSFENOAKAUJU-UHFFFAOYSA-L bis[[2-(4-chlorophenoxy)-2-methylpropanoyl]oxy]aluminum;hydrate Chemical compound O.C=1C=C(Cl)C=CC=1OC(C)(C)C(=O)O[Al]OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 RSMSFENOAKAUJU-UHFFFAOYSA-L 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 238000009534 blood test Methods 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000007686 hepatotoxicity Effects 0.000 description 1
- 231100000304 hepatotoxicity Toxicity 0.000 description 1
- 230000000055 hyoplipidemic effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 201000002364 leukopenia Diseases 0.000 description 1
- 231100001022 leukopenia Toxicity 0.000 description 1
- 229950003865 magnesium clofibrate Drugs 0.000 description 1
- SYMULEBHDFQHNX-UHFFFAOYSA-L magnesium;2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound [Mg+2].[O-]C(=O)C(C)(C)OC1=CC=C(Cl)C=C1.[O-]C(=O)C(C)(C)OC1=CC=C(Cl)C=C1 SYMULEBHDFQHNX-UHFFFAOYSA-L 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 229960003105 metformin Drugs 0.000 description 1
- 229960002581 moroxydine hydrochloride Drugs 0.000 description 1
- 238000009519 pharmacological trial Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 231100000046 skin rash Toxicity 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 238000005303 weighing Methods 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
- C07D295/16—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
- C07D295/20—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 carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8002927A FR2475546A1 (fr) | 1980-02-11 | 1980-02-11 | Phenoxyisobutyrates de moroxydine et medicaments les contenant |
| BE1/10121A BE887337A (fr) | 1980-02-11 | 1981-02-02 | Phenoxyisobutyrates de moroxydine et medicaments les contenant |
| NL8120018A NL8120018A (nl) | 1980-02-11 | 1981-02-05 | Moroxydinefenoxy-isobutyraten, en deze stoffen bevattende geneesmiddelen. |
| PCT/FR1981/000012 WO1981002295A1 (fr) | 1980-02-11 | 1981-02-05 | Phenoxyisobutyrates de moroxydine et medicaments les contenant |
| HU125681A HU182708B (en) | 1980-02-11 | 1981-02-05 | Process for preparing moroxydine-phenoxy-izobutyric acid derivatives |
| US06/308,546 US4372954A (en) | 1980-02-11 | 1981-02-05 | Moroxydine phenoxyisobutyrates and method of use |
| CH6673/81A CH651032A5 (fr) | 1980-02-11 | 1981-02-05 | Phenoxyisobutyrates de moroxydine et medicaments les contenant. |
| JP56500556A JPS57500285A (enExample) | 1980-02-11 | 1981-02-05 | |
| AU67702/81A AU538374B2 (en) | 1980-02-11 | 1981-02-05 | Phenoxyisobutyrates of moroxydin and drugs containing them |
| GB8129425A GB2080809B (en) | 1980-02-11 | 1981-02-05 | Phenoxyisobutyrates of moroxydin and drugs containing them |
| DE19813134452 DE3134452A1 (de) | 1980-02-11 | 1981-02-05 | Phenoxyisobutyrates of moroxydin and drugs containing them |
| IT19652/81A IT1135410B (it) | 1980-02-11 | 1981-02-11 | Fenossiisobutirrati di moroxidina e medicamenti contenenti gli stessi |
| SE8105929A SE8105929L (sv) | 1980-02-11 | 1981-10-07 | Moroxydinfenoxiisobutyrat och lekemedel innehallande dem |
| DK449881A DK449881A (da) | 1980-02-11 | 1981-10-09 | Fremgangsmaade til fremstilling af moroxydinphenoxyisobutyrater |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8002927A FR2475546A1 (fr) | 1980-02-11 | 1980-02-11 | Phenoxyisobutyrates de moroxydine et medicaments les contenant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2475546A1 true FR2475546A1 (fr) | 1981-08-14 |
| FR2475546B1 FR2475546B1 (enExample) | 1982-10-01 |
Family
ID=9238435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8002927A Granted FR2475546A1 (fr) | 1980-02-11 | 1980-02-11 | Phenoxyisobutyrates de moroxydine et medicaments les contenant |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE887337A (enExample) |
| FR (1) | FR2475546A1 (enExample) |
| HU (1) | HU182708B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2497666A2 (fr) * | 1981-01-14 | 1982-07-16 | Moreau Pierre | Medicaments contenant l'acide phenoxyisobutyrique et la moroxydine |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2357875A1 (de) * | 1973-03-16 | 1974-09-19 | Hurka Wilhelm | Clofibrinsaure salze des buformins und/oder metformins, verfahren zu deren herstellung und diese salze enthaltende arzneimittel |
| FR2315917A1 (fr) * | 1975-07-02 | 1977-01-28 | Poli Ind Chimica Spa | Nouveaux sels d'acide 2-p-chlorophenoxy-2-methyl-propionique d'aminoacides basiques, leur procede de preparation et medicament les contenant |
| DE2726392A1 (de) * | 1976-06-11 | 1977-12-22 | Kabi Ab | Mittel zur bekaempfung der venoesen thrombose |
-
1980
- 1980-02-11 FR FR8002927A patent/FR2475546A1/fr active Granted
-
1981
- 1981-02-02 BE BE1/10121A patent/BE887337A/fr not_active IP Right Cessation
- 1981-02-05 HU HU125681A patent/HU182708B/hu unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2357875A1 (de) * | 1973-03-16 | 1974-09-19 | Hurka Wilhelm | Clofibrinsaure salze des buformins und/oder metformins, verfahren zu deren herstellung und diese salze enthaltende arzneimittel |
| FR2315917A1 (fr) * | 1975-07-02 | 1977-01-28 | Poli Ind Chimica Spa | Nouveaux sels d'acide 2-p-chlorophenoxy-2-methyl-propionique d'aminoacides basiques, leur procede de preparation et medicament les contenant |
| DE2726392A1 (de) * | 1976-06-11 | 1977-12-22 | Kabi Ab | Mittel zur bekaempfung der venoesen thrombose |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2497666A2 (fr) * | 1981-01-14 | 1982-07-16 | Moreau Pierre | Medicaments contenant l'acide phenoxyisobutyrique et la moroxydine |
Also Published As
| Publication number | Publication date |
|---|---|
| HU182708B (en) | 1984-03-28 |
| FR2475546B1 (enExample) | 1982-10-01 |
| BE887337A (fr) | 1981-08-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TP | Transmission of property | ||
| ST | Notification of lapse |