FR2479218A2 - Nouvelles phenoxyamines heterocycliques substituees, leur methode de preparation et leur application comme anesthesiques locaux - Google Patents
Nouvelles phenoxyamines heterocycliques substituees, leur methode de preparation et leur application comme anesthesiques locaux Download PDFInfo
- Publication number
- FR2479218A2 FR2479218A2 FR8007352A FR8007352A FR2479218A2 FR 2479218 A2 FR2479218 A2 FR 2479218A2 FR 8007352 A FR8007352 A FR 8007352A FR 8007352 A FR8007352 A FR 8007352A FR 2479218 A2 FR2479218 A2 FR 2479218A2
- Authority
- FR
- France
- Prior art keywords
- sep
- compounds according
- compounds
- formula
- general 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.)
- Granted
Links
- 229960005015 local anesthetics Drugs 0.000 title description 4
- 150000005171 halobenzenes Chemical class 0.000 title 1
- -1 1-cyclohexenylmethyl Chemical group 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000003589 local anesthetic agent Substances 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000003444 anaesthetic effect Effects 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- QRGDLBSYQCSXHU-WLHGVMLRSA-N COC1=C(OCCC2NCCC2)C=C(C=C1Cl)Cl.C(\C=C\C(=O)O)(=O)O Chemical compound COC1=C(OCCC2NCCC2)C=C(C=C1Cl)Cl.C(\C=C\C(=O)O)(=O)O QRGDLBSYQCSXHU-WLHGVMLRSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 239000002547 new drug Substances 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims 1
- 229940031826 phenolate Drugs 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 206010002091 Anaesthesia Diseases 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000037005 anaesthesia Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- HWMNZNJLDKPDHA-WLHGVMLRSA-N (e)-but-2-enedioic acid;1-(cyclopropylmethyl)-2-[2-(3,5-dichloro-2-methoxyphenoxy)ethyl]pyrrolidine Chemical compound OC(=O)\C=C\C(O)=O.COC1=C(Cl)C=C(Cl)C=C1OCCC1N(CC2CC2)CCC1 HWMNZNJLDKPDHA-WLHGVMLRSA-N 0.000 description 1
- KYXPXJMQAUNAHE-UHFFFAOYSA-N 1-(cyclopropylmethyl)-2-[2-(3,5-dichloro-2-methoxyphenoxy)ethyl]pyrrolidine Chemical compound COC1=C(Cl)C=C(Cl)C=C1OCCC1N(CC2CC2)CCC1 KYXPXJMQAUNAHE-UHFFFAOYSA-N 0.000 description 1
- AYGSYTYAZVTIFR-UHFFFAOYSA-N 1-(cyclopropylmethyl)-4-(3,5-dichloro-2-methoxyphenoxy)azepane Chemical compound COC1=C(Cl)C=C(Cl)C=C1OC1CCN(CC2CC2)CCC1 AYGSYTYAZVTIFR-UHFFFAOYSA-N 0.000 description 1
- MEMQECHNVMLWST-UHFFFAOYSA-N 2-(2-chloroethyl)-1-(cyclopropylmethyl)pyrrolidine Chemical compound ClCCC1CCCN1CC1CC1 MEMQECHNVMLWST-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 0 COc(cc(*)cc1*)c1N Chemical compound COc(cc(*)cc1*)c1N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
- C07D223/08—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (57)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8007352A FR2479218A2 (fr) | 1980-04-01 | 1980-04-01 | Nouvelles phenoxyamines heterocycliques substituees, leur methode de preparation et leur application comme anesthesiques locaux |
| US06/162,796 US4379161A (en) | 1979-06-07 | 1980-06-25 | Novel substituted heterocyclic phenoxyamines, the method of preparation thereof and the use thereof as local anaesthetics |
| DE8080400999T DE3069789D1 (en) | 1979-07-06 | 1980-07-01 | Substituted heterocyclic phenoxy amines, their preparation method and their use as local anaesthetics |
| DE8383105420T DE3071314D1 (en) | 1979-07-06 | 1980-07-01 | 1-(1-cyclohexanyl-methyl) pyrrolidine derivatives, and process for their preparation |
| BG048341A BG35039A3 (bg) | 1979-07-06 | 1980-07-01 | Метод за получаване на заместени хетероциклични феноксиамини |
| BG062115A BG35746A3 (bg) | 1979-07-06 | 1980-07-01 | Метод за получаване на 1-циклохексенилметил прдукти |
| AT80400999T ATE10739T1 (de) | 1979-07-06 | 1980-07-01 | Substituierte heterocyclische phenoxyamine, verfahren zu ihrer herstellung und ihre verwendung als mittel fuer lokale anaesthesie. |
| AT83105420T ATE17119T1 (de) | 1979-07-06 | 1980-07-01 | 1-(1-cyclohexenylmethyl)pyrrolidin-derivate und verfahren zu deren herstellung. |
| EP83105420A EP0094102B1 (fr) | 1979-07-06 | 1980-07-01 | Nouveaux dérivés de 1-(1-cyclohexénylméthyl) pyrrolidine et leur procédé de préparation |
| OA57149A OA06561A (fr) | 1979-07-06 | 1980-07-01 | Nouvelles phénoxyamines hétérocycliques substituées, leur méthode de préparation et leur application comme anesthésiques locaux. |
| SU802938255A SU1085507A3 (ru) | 1979-07-06 | 1980-07-01 | Способ получени производных гетероциклических феноксиаминов |
| EP80400999A EP0024960B1 (fr) | 1979-07-06 | 1980-07-01 | Nouvelles phénoxyamines hétérocycliques substituées, procédé pour leur préparation et leur application comme anesthésiques locaux |
| YU1710/80A YU42344B (en) | 1979-07-06 | 1980-07-01 | Process for obtaining new substituted heterocyclic phenoxyamines |
| CS804693A CS216933B2 (en) | 1979-07-06 | 1980-07-01 | Method of making the heterocyclic phenoxyemines |
| AU60028/80A AU536482B2 (en) | 1979-07-06 | 1980-07-02 | Pyrrolidine and hexamethyleneimine derivatives |
| IL60472A IL60472A (en) | 1979-07-06 | 1980-07-02 | Substituted heterocyclic phenoxyamines,their preparation and pharmaceutical compositions containing them |
| BE1/9873A BE884124A (fr) | 1979-07-06 | 1980-07-02 | Nouvelles phenoxyamines heterocycliques substituees, leur methode de preparation et leur application comme anesthesiques locaux |
| PT71482A PT71482A (fr) | 1979-07-06 | 1980-07-02 | Procede de preparation de nouvelles phenoxyamines heterocycliques substituees utilisees a titre de medicaments nouveaux a activite anesthesique locale des formes optiquement actives et ainsi comme des produits intermediaires pour les memes composes |
| RO110029A RO85323B (ro) | 1979-07-06 | 1980-07-03 | Procedeu pentru prepararea unor fenoxiamine heterociclice |
| HU822217A HU186539B (en) | 1979-07-06 | 1980-07-03 | Process for producing 1-bracket-1-cyclohexenyl-methyl-bracket closed-2-bracket-2-chloroethyl-bracket closed-pyrrolidine |
| NZ194230A NZ194230A (en) | 1979-07-06 | 1980-07-03 | Phenoxy-(alkyl)-heterocyclic compounds intermediates pharmaceutical compositions |
| HU80801658A HU181147B (en) | 1979-07-06 | 1980-07-03 | Process for preparing substituted heterocyclin phenoxamines |
| AR281635A AR224012A1 (es) | 1979-07-06 | 1980-07-03 | Un procedimiento para la preparacion de nuevas fenoxiaminas heterociclicas sustituidas |
| RO101590A RO81532B (ro) | 1979-07-06 | 1980-07-03 | Procedeu de preparare a unor fenoxiamine heterociclice |
| IE1653/85A IE50061B1 (en) | 1979-07-06 | 1980-07-04 | 1-(1-cyclohexenylmethyl)pyrrolidine derivatives and process for their preparation |
| FI872955A FI872955A7 (fi) | 1979-07-06 | 1980-07-04 | 1-sykloheksenyylimetyylietyyli -pyrrolidiinijohdannaisia. |
| NO802027A NO156086C (no) | 1979-07-06 | 1980-07-04 | Analogifremgangsmaate for fremstilling av substituerte heterocykliske fenoksyaminer. |
| PL1980225473A PL127393B1 (en) | 1979-07-06 | 1980-07-04 | Method of obtaining new substituted heterocyclic phenoxyamines |
| IT49163/80A IT1188985B (it) | 1979-07-06 | 1980-07-04 | Fenossiammine eterocicliche sostituite procedimento per prepararle e composizioni farmaceutiche che le contengono |
| CH5169/80A CH648827A5 (fr) | 1979-07-06 | 1980-07-04 | Phenoxyamines heterocycliques substituees, leur preparation et medicaments consistant de ou comprenant ces composes. |
| MA19091A MA18893A1 (fr) | 1979-07-06 | 1980-07-04 | Nouvelles phenoxyamines heterocycliques substituees,leur methode de preparation et leur application comme anesthesiques locaux |
| MX8011334U MX7642E (es) | 1979-07-06 | 1980-07-04 | Procedimiento para preparar la 1-ciclo-hexenilmentil-2-cloroetil pirrolidina |
| CH5684/84A CH655100A5 (fr) | 1979-07-06 | 1980-07-04 | 1-cyclohexenyl-2-(hydroxy- ou chloro-)ethyl-pyrrolidine et procede pour sa preparation. |
| FI802156A FI74274C (fi) | 1979-07-06 | 1980-07-04 | Foerfarande foer framstaellning av nya, saosom lokalanestetika anvaendbara substituerade heterocykliska fenoxiaminer. |
| ES493111A ES493111A0 (es) | 1979-07-06 | 1980-07-04 | Un procedimiento de preparacion de nuevas fenoxiaminas hete-rociclicas |
| DK289580A DK157538C (da) | 1979-07-06 | 1980-07-04 | Analogifremgangsmaade til fremstilling af heterocycliske phenoxyaminer samt 1-cyclohexenylmethyl-pyrrolidiner til anvendelse som mellemprodukt ved fremgangsmaaden |
| GR62381A GR69638B (OSRAM) | 1979-07-06 | 1980-07-04 | |
| ZW152/80A ZW15280A1 (en) | 1979-07-06 | 1980-07-04 | Novel substituted heterocyclic phenoxyamines the method of preparation thereof and the use thereof as local anaestheetics |
| MX80100439U MX6366E (es) | 1979-07-06 | 1980-07-04 | Procedimiento para la preparacion de fenoxiaminas heterociclicas substituidas |
| IE1392/80A IE50060B1 (en) | 1979-07-06 | 1980-07-04 | Substituted heterocyclic phenoxyamines,method of preparation thereof and the use thereof as local anaesthetics |
| LU82584A LU82584A1 (fr) | 1979-07-06 | 1980-07-04 | Nouvelles phenoxyamines heterocycliques substituees,leur methode de preparation et leur application comme anesthesiques locaux |
| IN779/CAL/80A IN153037B (OSRAM) | 1979-07-06 | 1980-07-05 | |
| JO19801077A JO1077B1 (en) | 1979-07-06 | 1980-07-05 | New heterocyclic derivatives of phenoxiamine, methods of preparation and use as a local anesthetic. |
| DD222455A DD153206A5 (de) | 1979-07-06 | 1980-07-07 | Verfahren zur herstellung neuer substituierter heterozyklischer phenoxyamine |
| DD80234984A DD201141A5 (de) | 1979-07-06 | 1980-07-07 | Verfahren zur herstellung neuer substituierten heterozyklischer phenoxyamine |
| PH24248A PH16449A (en) | 1979-07-06 | 1980-07-07 | Novel substituted heterocyclic phenoxyamines and their use thereof as local anaesthetic |
| JP9321680A JPS5639065A (en) | 1979-07-06 | 1980-07-07 | Novel phenoxy heterocyclic amine* its manufacture and local narcotic as active component thereof |
| JP13751280A JPS5649351A (en) | 1979-07-06 | 1980-09-30 | Heterocyclic amine and its manufacture |
| CA000417963A CA1163273A (fr) | 1979-07-06 | 1982-12-16 | Phenoxyamines heterocycliques substituees, leur methode de preparation et leur application comme anesthesiques locaux |
| YU2801/82A YU42824B (en) | 1979-07-06 | 1982-12-17 | Process for obtaining new substituted pyrolidines |
| US06/456,523 US4594428A (en) | 1979-07-06 | 1983-01-07 | Novel substituted heterocyclic amines and methods of preparation thereof |
| IL68854A IL68854A0 (en) | 1979-07-06 | 1983-06-01 | Substituted 1-cyclohexenylmethyl 2-ethyl pyrrolidines and their preparation |
| IN1246/CAL/83A IN158706B (OSRAM) | 1979-07-06 | 1983-10-10 | |
| AU25260/84A AU563009B2 (en) | 1979-07-06 | 1984-03-02 | 1-(cyclohexenylmethylene)-pyrrolidine derivatives |
| NO861988A NO861988L (no) | 1979-07-06 | 1986-05-20 | Mellomprodukter for fremstilling av nye substituerte heterocykliske fenoksyaminer og fremgangsmaate for fremstilling derav. |
| HK556/89A HK55689A (en) | 1979-07-06 | 1989-07-13 | Substituted heterocyclic phenoxy amines,their preparation method and their use as local anaesthetics |
| HK558/89A HK55889A (en) | 1979-07-06 | 1989-07-13 | 1-(1-cyclohexanyl-methyl)pyrrolidine derivatives,and process for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8007352A FR2479218A2 (fr) | 1980-04-01 | 1980-04-01 | Nouvelles phenoxyamines heterocycliques substituees, leur methode de preparation et leur application comme anesthesiques locaux |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2479218A2 true FR2479218A2 (fr) | 1981-10-02 |
| FR2479218B2 FR2479218B2 (OSRAM) | 1983-07-08 |
Family
ID=9240420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8007352A Granted FR2479218A2 (fr) | 1979-06-07 | 1980-04-01 | Nouvelles phenoxyamines heterocycliques substituees, leur methode de preparation et leur application comme anesthesiques locaux |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2479218A2 (OSRAM) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1096441A (en) * | 1964-01-15 | 1967-12-29 | Bristol Myers Co | Ethers of benzyl phenols and a process for the preparation thereof |
| DE2026688A1 (de) * | 1969-06-12 | 1970-12-17 | Pfizer Corp., Colon (Panama) | Orthosubstituierte Phenoxyamine mit antihistaminischer Wirkung |
| EP0002672A2 (de) * | 1977-12-02 | 1979-07-11 | Byk Gulden Lomberg Chemische Fabrik GmbH | Substituierte Pyrrolidine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
| EP0004288A2 (de) * | 1978-03-18 | 1979-10-03 | MERCK PATENT GmbH | Phenoxyalkylamine, diese enthaltende pharmazeutische Zubereitungen und Verfahren zu ihrer Herstellung |
-
1980
- 1980-04-01 FR FR8007352A patent/FR2479218A2/fr active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1096441A (en) * | 1964-01-15 | 1967-12-29 | Bristol Myers Co | Ethers of benzyl phenols and a process for the preparation thereof |
| DE2026688A1 (de) * | 1969-06-12 | 1970-12-17 | Pfizer Corp., Colon (Panama) | Orthosubstituierte Phenoxyamine mit antihistaminischer Wirkung |
| EP0002672A2 (de) * | 1977-12-02 | 1979-07-11 | Byk Gulden Lomberg Chemische Fabrik GmbH | Substituierte Pyrrolidine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
| EP0004288A2 (de) * | 1978-03-18 | 1979-10-03 | MERCK PATENT GmbH | Phenoxyalkylamine, diese enthaltende pharmazeutische Zubereitungen und Verfahren zu ihrer Herstellung |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2479218B2 (OSRAM) | 1983-07-08 |
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