LU82584A1 - 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
- LU82584A1 LU82584A1 LU82584A LU82584A LU82584A1 LU 82584 A1 LU82584 A1 LU 82584A1 LU 82584 A LU82584 A LU 82584A LU 82584 A LU82584 A LU 82584A LU 82584 A1 LU82584 A1 LU 82584A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- pyrrolidine
- methoxy
- ethyl
- methyl
- dichlorophenoxyethyl
- Prior art date
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- 239000003589 local anesthetic agent Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 6
- 229960005015 local anesthetics Drugs 0.000 title description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 53
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 52
- -1 heterocyclic phenoxyamines Chemical class 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 230000000694 effects Effects 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- JZXVADSBLRIAIB-UHFFFAOYSA-N 2-pyrrolidin-2-ylethanol Chemical compound OCCC1CCCN1 JZXVADSBLRIAIB-UHFFFAOYSA-N 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- FCLZCOCSZQNREK-UHFFFAOYSA-N Pyrrolidine, hydrochloride Chemical compound Cl.C1CCNC1 FCLZCOCSZQNREK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- ZDXGQBUWNMFNIU-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-[2-(3,5-dichloro-2-methoxyphenoxy)ethyl]-1-methylpyrrolidine Chemical compound OC(=O)\C=C\C(O)=O.COC1=C(Cl)C=C(Cl)C=C1OCCC1N(C)CCC1 ZDXGQBUWNMFNIU-WLHGVMLRSA-N 0.000 claims description 2
- 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
- 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 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- KBSDLBVPAHQCRY-UHFFFAOYSA-N 307496-19-1 Chemical group C1CC=CCC1CC[Si](O1)(O2)O[Si](O3)(C4CCCC4)O[Si](O4)(C5CCCC5)O[Si]1(C1CCCC1)O[Si](O1)(C5CCCC5)O[Si]2(C2CCCC2)O[Si]3(C2CCCC2)O[Si]41C1CCCC1 KBSDLBVPAHQCRY-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000005340 bisphosphate group Chemical group 0.000 claims description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000006038 hexenyl group Chemical group 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims 2
- RMGFLMXDCGQKPS-UHFFFAOYSA-N 1-(2-chloroethyl)pyrrolidine Chemical compound ClCCN1CCCC1 RMGFLMXDCGQKPS-UHFFFAOYSA-N 0.000 claims 1
- PDKVWCYJNKLAGE-UHFFFAOYSA-N 1-(bromomethyl)cyclohexene Chemical compound BrCC1=CCCCC1 PDKVWCYJNKLAGE-UHFFFAOYSA-N 0.000 claims 1
- CCOFNTSQLIKTTQ-UHFFFAOYSA-N 1-(cyclohexen-1-ylmethyl)-2-[2-(3,5-dichloro-2-methoxyphenoxy)ethyl]pyrrolidine Chemical compound COC1=C(Cl)C=C(Cl)C=C1OCCC1N(CC=2CCCCC=2)CCC1 CCOFNTSQLIKTTQ-UHFFFAOYSA-N 0.000 claims 1
- CRPKIZXDTOMBDB-UHFFFAOYSA-N 1-[1-chloro-3-(cyclohexen-1-yl)propan-2-yl]pyrrolidine Chemical compound C1CCCN1C(CCl)CC1=CCCCC1 CRPKIZXDTOMBDB-UHFFFAOYSA-N 0.000 claims 1
- CTINRKGSNIHQMR-UHFFFAOYSA-N 2-(2-methylpyrrolidin-1-yl)ethanol Chemical compound CC1CCCN1CCO CTINRKGSNIHQMR-UHFFFAOYSA-N 0.000 claims 1
- 125000005336 allyloxy group Chemical group 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 239000002547 new drug Substances 0.000 claims 1
- UOKZUTXLHRTLFH-UHFFFAOYSA-N o-phenylhydroxylamine Chemical compound NOC1=CC=CC=C1 UOKZUTXLHRTLFH-UHFFFAOYSA-N 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 80
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 80
- 239000000243 solution Substances 0.000 description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- 239000000047 product Substances 0.000 description 39
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- 239000002585 base Substances 0.000 description 35
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
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- 238000002844 melting Methods 0.000 description 30
- 230000008018 melting Effects 0.000 description 30
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 238000010992 reflux Methods 0.000 description 19
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 229910021529 ammonia Inorganic materials 0.000 description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 11
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 8
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- OCQAXYHNMWVLRH-UHFFFAOYSA-N 2,3-dibenzoyl-2,3-dihydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(O)(C(O)=O)C(O)(C(=O)O)C(=O)C1=CC=CC=C1 OCQAXYHNMWVLRH-UHFFFAOYSA-N 0.000 description 5
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- 238000007920 subcutaneous administration 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
- 210000000689 upper leg Anatomy 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
-
- 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
-
- 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)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7917610 | 1979-06-07 | ||
| FR7917610A FR2460935A1 (fr) | 1979-07-06 | 1979-07-06 | Nouvelles phenoxyamines heterocycliques substituees, leur methode de preparation et leur application comme anesthetiques locaux |
| FR8007352 | 1980-01-04 | ||
| FR8007352A FR2479218A2 (fr) | 1980-04-01 | 1980-04-01 | Nouvelles phenoxyamines heterocycliques substituees, leur methode de preparation et leur application comme anesthesiques locaux |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU82584A1 true LU82584A1 (fr) | 1981-02-02 |
Family
ID=26221244
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU82584A LU82584A1 (fr) | 1979-07-06 | 1980-07-04 | Nouvelles phenoxyamines heterocycliques substituees,leur methode de preparation et leur application comme anesthesiques locaux |
Country Status (37)
| Country | Link |
|---|---|
| US (1) | US4379161A (ro) |
| EP (2) | EP0024960B1 (ro) |
| JP (2) | JPS5639065A (ro) |
| AR (1) | AR224012A1 (ro) |
| AT (2) | ATE10739T1 (ro) |
| AU (2) | AU536482B2 (ro) |
| BE (1) | BE884124A (ro) |
| BG (2) | BG35746A3 (ro) |
| CA (1) | CA1163273A (ro) |
| CH (2) | CH648827A5 (ro) |
| CS (1) | CS216933B2 (ro) |
| DD (2) | DD153206A5 (ro) |
| DE (2) | DE3071314D1 (ro) |
| DK (1) | DK157538C (ro) |
| ES (1) | ES493111A0 (ro) |
| FI (2) | FI74274C (ro) |
| GR (1) | GR69638B (ro) |
| HK (2) | HK55689A (ro) |
| HU (2) | HU186539B (ro) |
| IE (2) | IE50061B1 (ro) |
| IL (2) | IL60472A (ro) |
| IN (2) | IN153037B (ro) |
| IT (1) | IT1188985B (ro) |
| JO (1) | JO1077B1 (ro) |
| LU (1) | LU82584A1 (ro) |
| MA (1) | MA18893A1 (ro) |
| MX (2) | MX6366E (ro) |
| NO (2) | NO156086C (ro) |
| NZ (1) | NZ194230A (ro) |
| OA (1) | OA06561A (ro) |
| PH (1) | PH16449A (ro) |
| PL (1) | PL127393B1 (ro) |
| PT (1) | PT71482A (ro) |
| RO (2) | RO85323B (ro) |
| SU (1) | SU1085507A3 (ro) |
| YU (2) | YU42344B (ro) |
| ZW (1) | ZW15280A1 (ro) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2586018B1 (fr) * | 1985-08-12 | 1988-03-25 | Ile De France | Nouveau benzodioxepanne, son procede de synthese et ses applications en therapeutique |
| WO1990012004A1 (en) * | 1989-04-07 | 1990-10-18 | Fujisawa Pharmaceutical Co., Ltd. | New naphthalene compounds and method of producing the same |
| EP0471941A3 (en) * | 1990-08-16 | 1992-10-14 | American Cyanamid Company | An improved process for the preparation of 5-bromo-2-methoxyresorcinol |
| US5472958A (en) * | 1994-08-29 | 1995-12-05 | Abbott Laboratories | 2-((nitro)phenoxymethyl) heterocyclic compounds that enhance cognitive function |
| US7799337B2 (en) | 1997-07-21 | 2010-09-21 | Levin Bruce H | Method for directed intranasal administration of a composition |
| EP1034174B1 (en) * | 1997-11-05 | 2003-08-13 | Neurosearch A/S | Azaring-ether derivatives and their use as nicotinic ach receptor modulators |
| US8473062B2 (en) * | 2008-05-01 | 2013-06-25 | Autonomic Technologies, Inc. | Method and device for the treatment of headache |
| US8412336B2 (en) * | 2008-12-29 | 2013-04-02 | Autonomic Technologies, Inc. | Integrated delivery and visualization tool for a neuromodulation system |
| US9320908B2 (en) * | 2009-01-15 | 2016-04-26 | Autonomic Technologies, Inc. | Approval per use implanted neurostimulator |
| US8494641B2 (en) | 2009-04-22 | 2013-07-23 | Autonomic Technologies, Inc. | Implantable neurostimulator with integral hermetic electronic enclosure, circuit substrate, monolithic feed-through, lead assembly and anchoring mechanism |
| US20100185249A1 (en) * | 2009-01-22 | 2010-07-22 | Wingeier Brett M | Method and Devices for Adrenal Stimulation |
| CN111205015B (zh) * | 2020-01-20 | 2021-11-26 | 东南大学 | 一种高稳定泡沫混凝土发泡剂的制备方法 |
Family Cites Families (11)
| 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 |
| US3117976A (en) * | 1958-11-12 | 1964-01-14 | Beecham Res Lab | Nu-alkyl-pyrrolidine-2-methanol, alpha cyclohexyl mandelates |
| FR1342756A (fr) * | 1958-11-21 | 1963-11-15 | Beecham Res Lab | Esters basiques et leur procédé de préparation, notamment le phényl-cyclohexyl-glycolate de (1-méthyl-2-pyrrolidyl) méthyle et ses sels d'addition |
| GB1096441A (en) * | 1964-01-15 | 1967-12-29 | Bristol Myers Co | Ethers of benzyl phenols and a process for the preparation thereof |
| US3904622A (en) * | 1968-02-16 | 1975-09-09 | Ile De France | Dialkylaminoalkyl ethers of 2-alkoxy-3,5-dihalobenzene |
| GB1268951A (en) * | 1969-06-12 | 1972-03-29 | Pfizer Ltd | Phenoxy-amines |
| FR2155927A1 (en) * | 1971-10-15 | 1973-05-25 | Synthelabo | 1-phenylcyclo hexane carboxylic acid esters - with antispasmodic and anticholinergic activity |
| JPS5139661A (en) * | 1974-09-27 | 1976-04-02 | Nippon Kayaku Kk | Kogakukatsusei 11 mechiru 22 * beetaaa hidorokishechiru * pirorijin oyobisono chukantaino seizoho |
| JPS5251362A (en) * | 1975-10-20 | 1977-04-25 | Teijin Ltd | Preparation of optically active pyrrolidine derivatives |
| LU78625A1 (de) * | 1977-12-02 | 1979-06-13 | Byk Gulden Lomberg Chem Fab | Substituierte 1-phenyl-2-pyrrolidin-2-yl-ethanole,verfahren zu ihrer herstellung,ihre verwendung und sie enthaltende arzneimittel |
| DE2811952A1 (de) * | 1978-03-18 | 1979-10-31 | Merck Patent Gmbh | Phenoxyalkylamine und verfahren zu ihrer herstellung |
-
1980
- 1980-06-25 US US06/162,796 patent/US4379161A/en not_active Expired - Lifetime
- 1980-07-01 EP EP80400999A patent/EP0024960B1/fr not_active Expired
- 1980-07-01 BG BG8362115A patent/BG35746A3/xx unknown
- 1980-07-01 YU YU1710/80A patent/YU42344B/xx unknown
- 1980-07-01 OA OA57149A patent/OA06561A/xx unknown
- 1980-07-01 AT AT80400999T patent/ATE10739T1/de not_active IP Right Cessation
- 1980-07-01 DE DE8383105420T patent/DE3071314D1/de not_active Expired
- 1980-07-01 DE DE8080400999T patent/DE3069789D1/de not_active Expired
- 1980-07-01 SU SU802938255A patent/SU1085507A3/ru active
- 1980-07-01 EP EP83105420A patent/EP0094102B1/fr not_active Expired
- 1980-07-01 CS CS804693A patent/CS216933B2/cs unknown
- 1980-07-01 AT AT83105420T patent/ATE17119T1/de not_active IP Right Cessation
- 1980-07-01 BG BG8048341A patent/BG35039A3/xx unknown
- 1980-07-02 AU AU60028/80A patent/AU536482B2/en not_active Ceased
- 1980-07-02 PT PT71482A patent/PT71482A/pt unknown
- 1980-07-02 BE BE1/9873A patent/BE884124A/fr not_active IP Right Cessation
- 1980-07-02 IL IL60472A patent/IL60472A/xx unknown
- 1980-07-03 RO RO110029A patent/RO85323B/ro unknown
- 1980-07-03 RO RO101590A patent/RO81532B/ro unknown
- 1980-07-03 NZ NZ194230A patent/NZ194230A/xx unknown
- 1980-07-03 HU HU822217A patent/HU186539B/hu not_active IP Right Cessation
- 1980-07-03 HU HU80801658A patent/HU181147B/hu not_active IP Right Cessation
- 1980-07-03 AR AR281635A patent/AR224012A1/es active
- 1980-07-04 MX MX80100439U patent/MX6366E/es unknown
- 1980-07-04 FI FI802156A patent/FI74274C/fi not_active IP Right Cessation
- 1980-07-04 GR GR62381A patent/GR69638B/el unknown
- 1980-07-04 LU LU82584A patent/LU82584A1/fr unknown
- 1980-07-04 MX MX8011334U patent/MX7642E/es unknown
- 1980-07-04 CH CH5169/80A patent/CH648827A5/fr not_active IP Right Cessation
- 1980-07-04 MA MA19091A patent/MA18893A1/fr unknown
- 1980-07-04 ZW ZW152/80A patent/ZW15280A1/xx unknown
- 1980-07-04 CH CH5684/84A patent/CH655100A5/fr not_active IP Right Cessation
- 1980-07-04 ES ES493111A patent/ES493111A0/es active Granted
- 1980-07-04 NO NO802027A patent/NO156086C/no unknown
- 1980-07-04 PL PL1980225473A patent/PL127393B1/pl unknown
- 1980-07-04 IT IT49163/80A patent/IT1188985B/it active
- 1980-07-04 IE IE1653/85A patent/IE50061B1/en not_active IP Right Cessation
- 1980-07-04 DK DK289580A patent/DK157538C/da not_active IP Right Cessation
- 1980-07-04 IE IE1392/80A patent/IE50060B1/en not_active IP Right Cessation
- 1980-07-05 IN IN779/CAL/80A patent/IN153037B/en unknown
- 1980-07-05 JO JO19801077A patent/JO1077B1/en active
- 1980-07-07 DD DD222455A patent/DD153206A5/de unknown
- 1980-07-07 DD DD80234984A patent/DD201141A5/de not_active IP Right Cessation
- 1980-07-07 JP JP9321680A patent/JPS5639065A/ja active Granted
- 1980-07-07 PH PH24248A patent/PH16449A/en unknown
- 1980-09-30 JP JP13751280A patent/JPS5649351A/ja active Granted
-
1982
- 1982-12-16 CA CA000417963A patent/CA1163273A/fr not_active Expired
- 1982-12-17 YU YU2801/82A patent/YU42824B/xx unknown
-
1983
- 1983-06-01 IL IL68854A patent/IL68854A0/xx not_active IP Right Cessation
- 1983-10-10 IN IN1246/CAL/83A patent/IN158706B/en unknown
-
1984
- 1984-03-02 AU AU25260/84A patent/AU563009B2/en not_active Ceased
-
1986
- 1986-05-20 NO NO861988A patent/NO861988L/no unknown
-
1987
- 1987-07-03 FI FI872955A patent/FI872955A/fi not_active Application Discontinuation
-
1989
- 1989-07-13 HK HK556/89A patent/HK55689A/xx unknown
- 1989-07-13 HK HK558/89A patent/HK55889A/xx unknown
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