NO135934B - - Google Patents
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- Publication number
- NO135934B NO135934B NO4669/71A NO466971A NO135934B NO 135934 B NO135934 B NO 135934B NO 4669/71 A NO4669/71 A NO 4669/71A NO 466971 A NO466971 A NO 466971A NO 135934 B NO135934 B NO 135934B
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- ether
- reacted
- mol
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 40
- 239000003589 local anesthetic agent Substances 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 90
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 47
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 150000001408 amides Chemical class 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 18
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000000126 substance Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000012259 ether extract Substances 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 229960005015 local anesthetics Drugs 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 210000001519 tissue Anatomy 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 230000007794 irritation Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 206010042674 Swelling Diseases 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 230000007059 acute toxicity Effects 0.000 description 4
- 231100000403 acute toxicity Toxicity 0.000 description 4
- 230000003444 anaesthetic effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- -1 iodine ions Chemical class 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LEBVLXFERQHONN-UHFFFAOYSA-N 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide Chemical compound CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical group CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 229960003150 bupivacaine Drugs 0.000 description 2
- SIEYLFHKZGLBNX-UHFFFAOYSA-N bupivacaine hydrochloride (anhydrous) Chemical compound [Cl-].CCCC[NH+]1CCCCC1C(=O)NC1=C(C)C=CC=C1C SIEYLFHKZGLBNX-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 231100000517 death Toxicity 0.000 description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
- 229940008406 diethyl sulfate Drugs 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- AATGHKSFEUVOPF-UHFFFAOYSA-N diethylazanium;bromide Chemical compound [Br-].CC[NH2+]CC AATGHKSFEUVOPF-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 229940106885 marcaine Drugs 0.000 description 2
- INWLQCZOYSRPNW-UHFFFAOYSA-N mepivacaine Chemical compound CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C INWLQCZOYSRPNW-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- MVFGUOIZUNYYSO-UHFFFAOYSA-N prilocaine Chemical compound CCCNC(C)C(=O)NC1=CC=CC=C1C MVFGUOIZUNYYSO-UHFFFAOYSA-N 0.000 description 2
- OYCGKECKIVYHTN-UHFFFAOYSA-N pyrrocaine Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCCC1 OYCGKECKIVYHTN-UHFFFAOYSA-N 0.000 description 2
- 229960001367 tartaric acid Drugs 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 150000003892 tartrate salts Chemical class 0.000 description 2
- 229940072358 xylocaine Drugs 0.000 description 2
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- YAQLSKVCTLCIIE-UHFFFAOYSA-N 2-bromobutyric acid Chemical compound CCC(Br)C(O)=O YAQLSKVCTLCIIE-UHFFFAOYSA-N 0.000 description 1
- CSFUYRGXBNPTSR-UHFFFAOYSA-N 2-bromohexanoyl bromide Chemical compound CCCCC(Br)C(Br)=O CSFUYRGXBNPTSR-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- VTUSIVBDOCDNHS-UHFFFAOYSA-N Etidocaine Chemical compound CCCN(CC)C(CC)C(=O)NC1=C(C)C=CC=C1C VTUSIVBDOCDNHS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010021118 Hypotonia Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000786363 Rhampholeon spectrum Species 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000003461 brachial plexus Anatomy 0.000 description 1
- 229940105270 carbocaine Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229940097598 citanest Drugs 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960001270 d- tartaric acid Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 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
- 229960005139 epinephrine Drugs 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 230000006203 ethylation Effects 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960004194 lidocaine Drugs 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229960002409 mepivacaine Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- FFJMLWSZNCJCSZ-UHFFFAOYSA-N n-methylmethanamine;hydrobromide Chemical compound Br.CNC FFJMLWSZNCJCSZ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229960001807 prilocaine Drugs 0.000 description 1
- 229950000332 pyrrocaine Drugs 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000011477 surgical intervention Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/38—Acyl halides
- C07C53/46—Acyl halides containing halogen outside the carbonyl halide group
- C07C53/50—Acyl halides containing halogen outside the carbonyl halide group of acids containing three or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10077770A | 1970-12-22 | 1970-12-22 | |
| US00164022A US3812147A (en) | 1970-12-22 | 1971-07-19 | Acylxylidide local anaesthetics |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135934B true NO135934B (fi) | 1977-03-21 |
| NO135934C NO135934C (fi) | 1977-06-29 |
Family
ID=26797539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4669/71A NO135934C (fi) | 1970-12-22 | 1971-12-17 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3812147A (fi) |
| JP (1) | JPS5644063B1 (fi) |
| AR (1) | AR193840A1 (fi) |
| AT (1) | AT319205B (fi) |
| AU (1) | AU468489B2 (fi) |
| BE (1) | BE776656A (fi) |
| BR (1) | BR7108466D0 (fi) |
| CA (1) | CA943966A (fi) |
| DD (1) | DD99779A5 (fi) |
| DE (1) | DE2162744C3 (fi) |
| DK (1) | DK139814B (fi) |
| ES (2) | ES398210A1 (fi) |
| FI (1) | FI55027C (fi) |
| FR (1) | FR2118985B1 (fi) |
| GB (1) | GB1369259A (fi) |
| HU (1) | HU163373B (fi) |
| IE (1) | IE35909B1 (fi) |
| IT (1) | IT1066334B (fi) |
| NL (2) | NL172149C (fi) |
| NO (1) | NO135934C (fi) |
| PL (1) | PL83097B1 (fi) |
| SE (1) | SE393374B (fi) |
| SU (1) | SU419023A3 (fi) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4237068A (en) * | 1971-07-28 | 1980-12-02 | Astra Pharmaceutical Products, Inc. | Primary aminoacylanilides |
| US3966934A (en) * | 1971-12-08 | 1976-06-29 | Astra Pharmaceutical Products, Inc. | Synergistic local anesthetic compositions |
| US3957996A (en) * | 1971-12-08 | 1976-05-18 | Astra Pharmaceutical Products, Inc. | Pharmaceutical local anesthetic compositions |
| US3975443A (en) * | 1972-06-06 | 1976-08-17 | Allen & Hanburys Limited | 1-(3,4-dichlorobenzamidomethyl)-cyclohexyldimethylamine |
| JPS598269B2 (ja) * | 1975-08-22 | 1984-02-23 | 萬有製薬株式会社 | オメガ − アミノアルカンサンアリ−ルアミドノ セイホウ |
| JPS57176939A (en) * | 1981-04-03 | 1982-10-30 | Goodrich Co B F | Improved synthesis of hindered amine stabilizer for high polymer materials |
| US4891058A (en) * | 1988-07-18 | 1990-01-02 | Ici Americas Inc. | 1-alkyl-3-aryl imidazolidine-2,4-diones and herbicidal use |
| SE8900685D0 (sv) * | 1989-02-28 | 1989-02-28 | Astra Ab | New compounds |
| US5153226A (en) * | 1989-08-31 | 1992-10-06 | Warner-Lambert Company | Acat inhibitors for treating hypocholesterolemia |
| KR20090082507A (ko) | 2006-11-20 | 2009-07-30 | 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 | 통증 및 소양증 치료용 방법, 조성물 및 키트 |
| CA3027255C (en) | 2009-07-10 | 2022-06-21 | The General Hospital Corporation | Permanently charged sodium and calcium channel blockers as anti-inflammatory agents |
| JP6833811B2 (ja) | 2015-08-03 | 2021-02-24 | プレジデント アンド フェローズ オブ ハーバード カレッジ | 荷電イオンチャネル遮断薬及び使用方法 |
| US10968179B2 (en) | 2019-03-11 | 2021-04-06 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| MA55320A (fr) | 2019-03-11 | 2022-01-19 | Nocion Therapeutics Inc | Bloqueurs de canaux ioniques substitués par un ester et méthodes d'utilisation |
| EP3937945A4 (en) | 2019-03-11 | 2023-01-04 | Nocion Therapeutics, Inc. | CHARGED ION CHANNEL BLOCKERS AND METHODS OF USE |
| US10780083B1 (en) | 2019-03-11 | 2020-09-22 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10786485B1 (en) | 2019-03-11 | 2020-09-29 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| WO2021091585A1 (en) | 2019-11-06 | 2021-05-14 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10933055B1 (en) | 2019-11-06 | 2021-03-02 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| AU2021236130A1 (en) | 2020-03-11 | 2022-09-22 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1124837A (en) * | 1966-06-03 | 1968-08-21 | Wyeth John & Brother Ltd | Substituted anilides |
-
1971
- 1971-07-19 US US00164022A patent/US3812147A/en not_active Expired - Lifetime
- 1971-12-07 SE SE7115656A patent/SE393374B/xx unknown
- 1971-12-14 BE BE776656A patent/BE776656A/xx not_active IP Right Cessation
- 1971-12-15 SU SU1726195A patent/SU419023A3/ru active
- 1971-12-16 HU HUAA690A patent/HU163373B/hu unknown
- 1971-12-17 NO NO4669/71A patent/NO135934C/no unknown
- 1971-12-17 DE DE2162744A patent/DE2162744C3/de not_active Expired
- 1971-12-17 DK DK619771AA patent/DK139814B/da not_active IP Right Cessation
- 1971-12-18 IT IT54845/71A patent/IT1066334B/it active
- 1971-12-20 AT AT1089671A patent/AT319205B/de not_active IP Right Cessation
- 1971-12-20 AU AU37099/71A patent/AU468489B2/en not_active Expired
- 1971-12-20 IE IE1609/71A patent/IE35909B1/xx unknown
- 1971-12-21 ES ES398210A patent/ES398210A1/es not_active Expired
- 1971-12-21 BR BR8466/71A patent/BR7108466D0/pt unknown
- 1971-12-21 DD DD159785A patent/DD99779A5/xx unknown
- 1971-12-21 PL PL1971152331A patent/PL83097B1/pl unknown
- 1971-12-21 FR FR7145983A patent/FR2118985B1/fr not_active Expired
- 1971-12-21 GB GB5937771A patent/GB1369259A/en not_active Expired
- 1971-12-21 AR AR239721A patent/AR193840A1/es active
- 1971-12-21 CA CA130,662A patent/CA943966A/en not_active Expired
- 1971-12-22 NL NLAANVRAGE7117644,A patent/NL172149C/xx not_active IP Right Cessation
- 1971-12-22 FI FI3658/71A patent/FI55027C/fi active
- 1971-12-22 JP JP10453571A patent/JPS5644063B1/ja active Pending
-
1974
- 1974-04-24 ES ES425626A patent/ES425626A1/es not_active Expired
-
1982
- 1982-10-26 NL NL8204126A patent/NL8204126A/nl not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ES398210A1 (es) | 1975-03-16 |
| FI55027C (fi) | 1979-05-10 |
| IE35909L (en) | 1972-06-22 |
| GB1369259A (en) | 1974-10-23 |
| NL8204126A (nl) | 1983-02-01 |
| JPS5644063B1 (fi) | 1981-10-16 |
| DE2162744B2 (de) | 1981-07-02 |
| DE2162744A1 (de) | 1972-07-06 |
| ES425626A1 (es) | 1976-06-16 |
| AR193840A1 (es) | 1973-05-31 |
| CA943966A (en) | 1974-03-19 |
| FR2118985A1 (fi) | 1972-08-04 |
| AU3709971A (en) | 1973-06-28 |
| IT1066334B (it) | 1985-03-04 |
| HU163373B (fi) | 1973-08-28 |
| DE2162744C3 (de) | 1982-04-15 |
| NO135934C (fi) | 1977-06-29 |
| US3812147A (en) | 1974-05-21 |
| NL7117644A (fi) | 1972-06-26 |
| NL172149C (nl) | 1983-07-18 |
| FR2118985B1 (fi) | 1975-12-26 |
| PL83097B1 (fi) | 1975-12-31 |
| DK139814C (fi) | 1979-10-01 |
| IE35909B1 (en) | 1976-06-23 |
| BR7108466D0 (pt) | 1973-06-14 |
| DK139814B (da) | 1979-04-23 |
| AT319205B (de) | 1974-12-10 |
| BE776656A (fr) | 1972-06-14 |
| AU468489B2 (en) | 1976-01-15 |
| NL172149B (nl) | 1983-02-16 |
| SU419023A3 (ru) | 1974-03-05 |
| DD99779A5 (fi) | 1973-08-20 |
| FI55027B (fi) | 1979-01-31 |
| SE393374B (sv) | 1977-05-09 |
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