DE2728315A1 - Glycerin-1,2-bis-(aminoalkylaether), verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate - Google Patents
Glycerin-1,2-bis-(aminoalkylaether), verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparateInfo
- Publication number
- DE2728315A1 DE2728315A1 DE19772728315 DE2728315A DE2728315A1 DE 2728315 A1 DE2728315 A1 DE 2728315A1 DE 19772728315 DE19772728315 DE 19772728315 DE 2728315 A DE2728315 A DE 2728315A DE 2728315 A1 DE2728315 A1 DE 2728315A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- compound
- bis
- compounds
- glycerol
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 41
- 238000000034 method Methods 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 229940126601 medicinal product Drugs 0.000 title 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- -1 aminoalkyl ether Chemical compound 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 159000000000 sodium salts Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229940066768 systemic antihistamines aminoalkyl ethers Drugs 0.000 claims description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- YFBMUIMQJYESPZ-UHFFFAOYSA-N 3-phenoxy-1,2-propanediol Natural products C1C(OC(C)=O)CCC2(C)C3=CCC4(C)C(C(C)CCC(CC)C(C)C)CCC4(C)C3CCC21 YFBMUIMQJYESPZ-UHFFFAOYSA-N 0.000 claims description 2
- FNQIYTUXOKTMDM-UHFFFAOYSA-N 3-phenoxypropane-1,2-diol Chemical compound OCC(O)COC1=CC=CC=C1 FNQIYTUXOKTMDM-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- JHWQMXKQJVAWKI-UHFFFAOYSA-N UNPD187286 Natural products OCC(O)CC1=CC=CC=C1 JHWQMXKQJVAWKI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 150000004683 dihydrates Chemical class 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000001294 propane Substances 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 5
- 229960004194 lidocaine Drugs 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 230000003288 anthiarrhythmic effect Effects 0.000 description 4
- 125000002474 dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 206010003119 arrhythmia Diseases 0.000 description 3
- 230000006793 arrhythmia Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000003589 local anesthetic agent Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- XFSBVAOIAHNAPC-XTHSEXKGSA-N 16-Ethyl-1alpha,6alpha,19beta-trimethoxy-4-(methoxymethyl)-aconitane-3alpha,8,10alpha,11,18alpha-pentol, 8-acetate 10-benzoate Chemical compound O([C@H]1[C@]2(O)C[C@H]3[C@@]45C6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)[C@@H]4[C@]([C@@H](C[C@@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-XTHSEXKGSA-N 0.000 description 2
- CJDRUOGAGYHKKD-RQBLFBSQSA-N 1pon08459r Chemical compound CN([C@H]1[C@@]2(C[C@@]3([H])[C@@H]([C@@H](O)N42)CC)[H])C2=CC=CC=C2[C@]11C[C@@]4([H])[C@H]3[C@H]1O CJDRUOGAGYHKKD-RQBLFBSQSA-N 0.000 description 2
- XFSBVAOIAHNAPC-UHFFFAOYSA-N Aconitin Natural products CCN1CC(C(CC2OC)O)(COC)C3C(OC)C(C(C45)(OC(C)=O)C(O)C6OC)C1C32C4CC6(O)C5OC(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CJDRUOGAGYHKKD-UHFFFAOYSA-N Iso-ajmalin Natural products CN1C2=CC=CC=C2C2(C(C34)O)C1C1CC3C(CC)C(O)N1C4C2 CJDRUOGAGYHKKD-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 244000061121 Rauvolfia serpentina Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229940039750 aconitine Drugs 0.000 description 2
- STDXGNLCJACLFY-UHFFFAOYSA-N aconitine Natural products CCN1CC2(COC)C(O)CC(O)C34C5CC6(O)C(OC)C(O)C(OC(=O)C)(C5C6OC(=O)c7ccccc7)C(C(OC)C23)C14 STDXGNLCJACLFY-UHFFFAOYSA-N 0.000 description 2
- 229960004332 ajmaline Drugs 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000033764 rhythmic process Effects 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- RKBUSASMODUQSK-UHFFFAOYSA-N 1-(2,6-dimethylphenoxy)propane-1,2,3-triol Chemical compound CC1=C(OC(O)C(O)CO)C(=CC=C1)C RKBUSASMODUQSK-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
- 208000020446 Cardiac disease 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
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- YEBKCCIUOGRTML-UHFFFAOYSA-N chloro hypochlorite propane Chemical compound CCC.ClOCl YEBKCCIUOGRTML-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000001057 ionotropic effect Effects 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000002690 local anesthesia Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229960005010 orotic acid Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 210000003497 sciatic nerve Anatomy 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH921776A CH602581A5 (US08124317-20120228-C00026.png) | 1976-07-19 | 1976-07-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2728315A1 true DE2728315A1 (de) | 1978-01-26 |
| DE2728315C2 DE2728315C2 (de) | 1987-01-22 |
Family
ID=4349615
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2728315A Expired DE2728315C2 (de) | 1976-07-19 | 1977-06-23 | Glycerin-1,2-bis-(aminoalkyläther), Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneipräparate |
Country Status (17)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7799337B2 (en) | 1997-07-21 | 2010-09-21 | Levin Bruce H | Method for directed intranasal administration of a composition |
| 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 |
| 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 |
| US9320908B2 (en) | 2009-01-15 | 2016-04-26 | Autonomic Technologies, Inc. | Approval per use implanted neurostimulator |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2431126A1 (de) * | 1974-06-28 | 1976-01-15 | Christian Brunnengraeber Chem | Therapeutikum mit antiarrhythischer wirkung |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2738351A (en) * | 1952-08-02 | 1956-03-13 | Bristol Lab Inc | Substituted glycerol ethers |
| US2895995A (en) * | 1957-04-10 | 1959-07-21 | Willey George Lawrence | Quaternary ammonium salts of dialkylaminoalkyl phenyl ethers |
| GB1262785A (en) * | 1969-04-29 | 1972-02-09 | Orsymonde | Improvements in or relating to phloroglucinol derivatives |
| FR2146893B1 (US08124317-20120228-C00026.png) * | 1971-07-23 | 1974-09-06 | Crt |
-
1976
- 1976-07-19 CH CH921776A patent/CH602581A5/xx not_active IP Right Cessation
-
1977
- 1977-06-23 DE DE2728315A patent/DE2728315C2/de not_active Expired
- 1977-06-27 GB GB26786/77A patent/GB1572370A/en not_active Expired
- 1977-06-27 NL NLAANVRAGE7707088,A patent/NL187909C/xx active Search and Examination
- 1977-06-29 BE BE178897A patent/BE856258A/xx not_active IP Right Cessation
- 1977-07-05 FI FI772105A patent/FI67537C/fi not_active IP Right Cessation
- 1977-07-08 US US05/813,985 patent/US4117160A/en not_active Expired - Lifetime
- 1977-07-11 ZA ZA00774155A patent/ZA774155B/xx unknown
- 1977-07-11 CA CA282,474A patent/CA1095085A/en not_active Expired
- 1977-07-12 FR FR7721561A patent/FR2359118A1/fr active Granted
- 1977-07-14 NZ NZ184647A patent/NZ184647A/xx unknown
- 1977-07-15 AU AU27060/77A patent/AU2706077A/en active Pending
- 1977-07-16 ES ES460825A patent/ES460825A1/es not_active Expired
- 1977-07-18 DK DK324577A patent/DK158463C/da not_active IP Right Cessation
- 1977-07-18 SE SE7708299A patent/SE429755B/xx not_active IP Right Cessation
- 1977-07-18 AT AT516677A patent/AT349447B/de not_active IP Right Cessation
- 1977-07-19 JP JP8657977A patent/JPS5312828A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2431126A1 (de) * | 1974-06-28 | 1976-01-15 | Christian Brunnengraeber Chem | Therapeutikum mit antiarrhythischer wirkung |
Also Published As
| Publication number | Publication date |
|---|---|
| SE429755B (sv) | 1983-09-26 |
| ATA516677A (de) | 1978-09-15 |
| FR2359118B1 (US08124317-20120228-C00026.png) | 1979-05-11 |
| US4117160A (en) | 1978-09-26 |
| CH602581A5 (US08124317-20120228-C00026.png) | 1978-07-31 |
| JPS5312828A (en) | 1978-02-04 |
| FR2359118A1 (fr) | 1978-02-17 |
| ZA774155B (en) | 1978-05-30 |
| AU2706077A (en) | 1979-01-18 |
| SE7708299L (sv) | 1978-01-20 |
| CA1095085A (en) | 1981-02-03 |
| DK158463C (da) | 1990-10-08 |
| FI67537B (fi) | 1984-12-31 |
| DE2728315C2 (de) | 1987-01-22 |
| DK158463B (da) | 1990-05-21 |
| NL7707088A (nl) | 1978-01-23 |
| FI67537C (fi) | 1985-04-10 |
| ES460825A1 (es) | 1978-04-16 |
| BE856258A (fr) | 1977-10-17 |
| JPS6228776B2 (US08124317-20120228-C00026.png) | 1987-06-23 |
| FI772105A (US08124317-20120228-C00026.png) | 1978-01-20 |
| NZ184647A (en) | 1979-12-11 |
| DK324577A (da) | 1978-01-20 |
| GB1572370A (en) | 1980-07-30 |
| AT349447B (de) | 1979-04-10 |
| NL187909C (nl) | 1992-02-17 |
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