FR2460935A1 - Nouvelles phenoxyamines heterocycliques substituees, leur methode de preparation et leur application comme anesthetiques locaux - Google Patents
Nouvelles phenoxyamines heterocycliques substituees, leur methode de preparation et leur application comme anesthetiques locaux Download PDFInfo
- Publication number
- FR2460935A1 FR2460935A1 FR7917610A FR7917610A FR2460935A1 FR 2460935 A1 FR2460935 A1 FR 2460935A1 FR 7917610 A FR7917610 A FR 7917610A FR 7917610 A FR7917610 A FR 7917610A FR 2460935 A1 FR2460935 A1 FR 2460935A1
- Authority
- FR
- France
- Prior art keywords
- sep
- pyrrolidine
- methoxy
- dichlorophenoxyethyl
- compounds
- 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 3
- 150000005171 halobenzenes Chemical class 0.000 title 1
- -1 1-cyclohexenylmethyl Chemical group 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims description 50
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 46
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 25
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 11
- RTLULEZPCUMDKR-UHFFFAOYSA-N 2-[2-(3,5-dichloro-2-methoxyphenoxy)ethyl]-1-methylpyrrolidine Chemical compound COC1=C(Cl)C=C(Cl)C=C1OCCC1N(C)CCC1 RTLULEZPCUMDKR-UHFFFAOYSA-N 0.000 claims description 7
- 230000003444 anaesthetic effect Effects 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- MWFCGPKABKLWSH-UHFFFAOYSA-N 2-[2-(3,5-dichloro-2-methoxyphenoxy)ethyl]-1-ethylpyrrolidine;hydrochloride Chemical compound Cl.CCN1CCCC1CCOC1=CC(Cl)=CC(Cl)=C1OC MWFCGPKABKLWSH-UHFFFAOYSA-N 0.000 claims description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- LQUOOBUMUREJOX-UHFFFAOYSA-N 2-[2-(3,5-dichlorophenoxy)ethyl]-1-ethylpyrrolidine Chemical compound CCN1CCCC1CCOC1=CC(Cl)=CC(Cl)=C1 LQUOOBUMUREJOX-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- PGUUVUHWEJYLKT-UHFFFAOYSA-N 2-[2-(3,5-dichloro-2-ethoxyphenoxy)ethyl]-1-ethylpyrrolidine;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.CCOC1=C(Cl)C=C(Cl)C=C1OCCC1N(CC)CCC1 PGUUVUHWEJYLKT-UHFFFAOYSA-N 0.000 claims description 2
- FCLZCOCSZQNREK-UHFFFAOYSA-N Pyrrolidine, hydrochloride Chemical compound Cl.C1CCNC1 FCLZCOCSZQNREK-UHFFFAOYSA-N 0.000 claims description 2
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- RASPWLYDBYZRCR-UHFFFAOYSA-N pyrrolidin-1-ium-2-one;chloride Chemical compound Cl.O=C1CCCN1 RASPWLYDBYZRCR-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
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- DBARMDUSHJFUOJ-UHFFFAOYSA-N 2-[2-(3,5-dichloro-2-methoxyphenoxy)ethyl]-1-ethylpyrrolidine Chemical compound CCN1CCCC1CCOC1=CC(Cl)=CC(Cl)=C1OC DBARMDUSHJFUOJ-UHFFFAOYSA-N 0.000 description 3
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- 208000000856 Postphlebitic Syndrome Diseases 0.000 description 1
- 208000035999 Recurrence Diseases 0.000 description 1
- 206010040914 Skin reaction Diseases 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 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
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000014306 Trophic disease Diseases 0.000 description 1
- FKCMADOPPWWGNZ-YUMQZZPRSA-N [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O FKCMADOPPWWGNZ-YUMQZZPRSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 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
- 229940035674 anesthetics Drugs 0.000 description 1
- 229960004543 anhydrous citric acid Drugs 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
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- 235000019789 appetite Nutrition 0.000 description 1
- ANHCOYQSQBAJKK-UHFFFAOYSA-N azane;2-phenylethanol Chemical compound N.OCCC1=CC=CC=C1 ANHCOYQSQBAJKK-UHFFFAOYSA-N 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
- 230000001680 brushing effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- PIQVDUKEQYOJNR-VZXSFKIWSA-N cocaine hydrochloride Chemical compound [Cl-].O([C@H]1C[C@@H]2CC[C@@H]([NH+]2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 PIQVDUKEQYOJNR-VZXSFKIWSA-N 0.000 description 1
- 229960003771 cocaine hydrochloride Drugs 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000000245 forearm Anatomy 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- VRIVJOXICYMTAG-IYEMJOQQSA-L iron(ii) gluconate Chemical compound [Fe+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O VRIVJOXICYMTAG-IYEMJOQQSA-L 0.000 description 1
- 230000007803 itching Effects 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- CEQFOVLGLXCDCX-WUKNDPDISA-N methyl red Chemical compound C1=CC(N(C)C)=CC=C1\N=N\C1=CC=CC=C1C(O)=O CEQFOVLGLXCDCX-WUKNDPDISA-N 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000000422 nocturnal effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000399 orthopedic effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- AVTYONGGKAJVTE-OLXYHTOASA-L potassium L-tartrate Chemical compound [K+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O AVTYONGGKAJVTE-OLXYHTOASA-L 0.000 description 1
- 239000001472 potassium tartrate Substances 0.000 description 1
- 229940111695 potassium tartrate Drugs 0.000 description 1
- 235000011005 potassium tartrates Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 230000035483 skin reaction Effects 0.000 description 1
- 231100000430 skin reaction Toxicity 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 210000002303 tibia Anatomy 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 229940072358 xylocaine Drugs 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 (58)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7917610A FR2460935A1 (fr) | 1979-07-06 | 1979-07-06 | Nouvelles phenoxyamines heterocycliques substituees, leur methode de preparation et leur application comme anesthetiques 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 |
| BG062115A BG35746A3 (bg) | 1979-07-06 | 1980-07-01 | Метод за получаване на 1-циклохексенилметил прдукти |
| DE8383105420T DE3071314D1 (en) | 1979-07-06 | 1980-07-01 | 1-(1-cyclohexanyl-methyl) pyrrolidine derivatives, and process for their preparation |
| EP83105420A EP0094102B1 (fr) | 1979-07-06 | 1980-07-01 | Nouveaux dérivés de 1-(1-cyclohexénylméthyl) pyrrolidine et leur procédé de préparation |
| DE8080400999T DE3069789D1 (en) | 1979-07-06 | 1980-07-01 | Substituted heterocyclic phenoxy amines, their preparation method and their use as local anaesthetics |
| AT83105420T ATE17119T1 (de) | 1979-07-06 | 1980-07-01 | 1-(1-cyclohexenylmethyl)pyrrolidin-derivate und verfahren zu deren herstellung. |
| YU1710/80A YU42344B (en) | 1979-07-06 | 1980-07-01 | Process for obtaining new substituted heterocyclic phenoxyamines |
| OA57149A OA06561A (fr) | 1979-07-06 | 1980-07-01 | Nouvelles phénoxyamines hétérocycliques substituées, leur méthode de préparation et leur application comme anesthésiques locaux. |
| EP80400999A EP0024960B1 (fr) | 1979-07-06 | 1980-07-01 | Nouvelles phénoxyamines hétérocycliques substituées, procédé pour leur préparation et leur application comme anesthésiques locaux |
| AT80400999T ATE10739T1 (de) | 1979-07-06 | 1980-07-01 | Substituierte heterocyclische phenoxyamine, verfahren zu ihrer herstellung und ihre verwendung als mittel fuer lokale anaesthesie. |
| BG048341A BG35039A3 (bg) | 1979-07-06 | 1980-07-01 | Метод за получаване на заместени хетероциклични феноксиамини |
| CS804693A CS216933B2 (en) | 1979-07-06 | 1980-07-01 | Method of making the heterocyclic phenoxyemines |
| SU802938255A SU1085507A3 (ru) | 1979-07-06 | 1980-07-01 | Способ получени производных гетероциклических феноксиаминов |
| AU60028/80A AU536482B2 (en) | 1979-07-06 | 1980-07-02 | Pyrrolidine and hexamethyleneimine derivatives |
| 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 |
| IL60472A IL60472A (en) | 1979-07-06 | 1980-07-02 | Substituted heterocyclic phenoxyamines,their preparation and pharmaceutical compositions containing them |
| NZ194230A NZ194230A (en) | 1979-07-06 | 1980-07-03 | Phenoxy-(alkyl)-heterocyclic compounds intermediates pharmaceutical compositions |
| RO110029A RO85323B (ro) | 1979-07-06 | 1980-07-03 | Procedeu pentru prepararea unor fenoxiamine heterociclice |
| RO101590A RO81532B (ro) | 1979-07-06 | 1980-07-03 | Procedeu de preparare a 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 |
| AR281635A AR224012A1 (es) | 1979-07-06 | 1980-07-03 | Un procedimiento para la preparacion de nuevas fenoxiaminas heterociclicas sustituidas |
| HU80801658A HU181147B (en) | 1979-07-06 | 1980-07-03 | Process for preparing substituted heterocyclin phenoxamines |
| CH5684/84A CH655100A5 (fr) | 1979-07-06 | 1980-07-04 | 1-cyclohexenyl-2-(hydroxy- ou chloro-)ethyl-pyrrolidine et procede pour sa preparation. |
| GR62381A GR69638B (Direct) | 1979-07-06 | 1980-07-04 | |
| MX80100439U MX6366E (es) | 1979-07-06 | 1980-07-04 | Procedimiento para la preparacion de fenoxiaminas heterociclicas substituidas |
| MA19091A MA18893A1 (fr) | 1979-07-06 | 1980-07-04 | Nouvelles phenoxyamines heterocycliques substituees,leur methode de preparation et leur application comme anesthesiques locaux |
| IE1392/80A IE50060B1 (en) | 1979-07-06 | 1980-07-04 | Substituted heterocyclic phenoxyamines,method of preparation thereof and the use thereof as local anaesthetics |
| ZA00804035A ZA804035B (en) | 1979-07-06 | 1980-07-04 | Novel substituted heterocyclic phenoxyamines, the method of preparation thereof and the use thereof as local anaesthetics |
| MX8011334U MX7642E (es) | 1979-07-06 | 1980-07-04 | Procedimiento para preparar la 1-ciclo-hexenilmentil-2-cloroetil pirrolidina |
| IT49163/80A IT1188985B (it) | 1979-07-06 | 1980-07-04 | Fenossiammine eterocicliche sostituite procedimento per prepararle e composizioni farmaceutiche che le contengono |
| LU82584A LU82584A1 (fr) | 1979-07-06 | 1980-07-04 | Nouvelles phenoxyamines heterocycliques substituees,leur methode de preparation et leur application comme anesthesiques locaux |
| IE1653/85A IE50061B1 (en) | 1979-07-06 | 1980-07-04 | 1-(1-cyclohexenylmethyl)pyrrolidine derivatives and process for their preparation |
| NO802027A NO156086C (no) | 1979-07-06 | 1980-07-04 | Analogifremgangsmaate for fremstilling av substituerte heterocykliske fenoksyaminer. |
| ES493111A ES8103049A1 (es) | 1979-07-06 | 1980-07-04 | Un procedimiento de preparacion de nuevas fenoxiaminas hete-rociclicas |
| 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 |
| CH5169/80A CH648827A5 (fr) | 1979-07-06 | 1980-07-04 | Phenoxyamines heterocycliques substituees, leur preparation et medicaments consistant de ou comprenant ces composes. |
| PL1980225473A PL127393B1 (en) | 1979-07-06 | 1980-07-04 | Method of obtaining new substituted heterocyclic phenoxyamines |
| FI872955A FI872955A0 (fi) | 1979-07-06 | 1980-07-04 | 1-cyklohexenylmetyletyl-pyrrolidinderivat. |
| 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 |
| FI802156A FI74274C (fi) | 1979-07-06 | 1980-07-04 | Foerfarande foer framstaellning av nya, saosom lokalanestetika anvaendbara substituerade heterocykliska fenoxiaminer. |
| IN779/CAL/80A IN153037B (Direct) | 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. |
| 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 |
| 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 |
| 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 (Direct) | 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. |
| HK558/89A HK55889A (en) | 1979-07-06 | 1989-07-13 | 1-(1-cyclohexanyl-methyl)pyrrolidine derivatives,and process for their preparation |
| HK556/89A HK55689A (en) | 1979-07-06 | 1989-07-13 | Substituted heterocyclic phenoxy amines,their preparation method and their use as local anaesthetics |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7917610A FR2460935A1 (fr) | 1979-07-06 | 1979-07-06 | Nouvelles phenoxyamines heterocycliques substituees, leur methode de preparation et leur application comme anesthetiques locaux |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2460935A1 true FR2460935A1 (fr) | 1981-01-30 |
| FR2460935B1 FR2460935B1 (Direct) | 1982-12-03 |
Family
ID=9227617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7917610A Granted FR2460935A1 (fr) | 1979-06-07 | 1979-07-06 | Nouvelles phenoxyamines heterocycliques substituees, leur methode de preparation et leur application comme anesthetiques locaux |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR2460935A1 (Direct) |
| ZA (1) | ZA804035B (Direct) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE543876C (de) * | 1928-04-25 | 1932-02-11 | C H Boehringer Sohn Akt Ges | Verfahren zur Darstellung von Piperidinalkinen |
| 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 |
-
1979
- 1979-07-06 FR FR7917610A patent/FR2460935A1/fr active Granted
-
1980
- 1980-07-04 ZA ZA00804035A patent/ZA804035B/xx unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE543876C (de) * | 1928-04-25 | 1932-02-11 | C H Boehringer Sohn Akt Ges | Verfahren zur Darstellung von Piperidinalkinen |
| 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 |
|---|---|
| ZA804035B (en) | 1981-06-24 |
| FR2460935B1 (Direct) | 1982-12-03 |
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