DE3010599C2 - - Google Patents
Info
- Publication number
- DE3010599C2 DE3010599C2 DE3010599A DE3010599A DE3010599C2 DE 3010599 C2 DE3010599 C2 DE 3010599C2 DE 3010599 A DE3010599 A DE 3010599A DE 3010599 A DE3010599 A DE 3010599A DE 3010599 C2 DE3010599 C2 DE 3010599C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- amino
- acetamide
- pentylamino
- oxoethyl
- 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.)
- Expired
Links
- -1 2 - [(2-phenylethyl) amino] -acetamide 2 - [(3-phenylpropyl) amino] -acetamide Chemical compound 0.000 claims description 17
- 150000001413 amino acids Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 2
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 230000000694 effects Effects 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000000126 substance Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 229940024606 amino acid Drugs 0.000 description 13
- 235000001014 amino acid Nutrition 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- IYGYMKDQCDOMRE-QRWMCTBCSA-N Bicculine Chemical compound O([C@H]1C2C3=CC=4OCOC=4C=C3CCN2C)C(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-QRWMCTBCSA-N 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 10
- IYGYMKDQCDOMRE-UHFFFAOYSA-N d-Bicucullin Natural products CN1CCC2=CC=3OCOC=3C=C2C1C1OC(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- AACMFFIUYXGCOC-UHFFFAOYSA-N bicuculline Natural products CN1CCc2cc3OCOc3cc2C1C4OCc5c6OCOc6ccc45 AACMFFIUYXGCOC-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 9
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 102000008214 Glutamate decarboxylase Human genes 0.000 description 6
- 108091022930 Glutamate decarboxylase Proteins 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 208000007101 Muscle Cramp Diseases 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- GJNNXIYZWIZFRH-UHFFFAOYSA-N 2-(pentylamino)acetamide Chemical compound CCCCCNCC(N)=O GJNNXIYZWIZFRH-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 208000005392 Spasm Diseases 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- QEJUSMMBSMNFBF-UHFFFAOYSA-N 2-(hexylamino)acetamide Chemical compound CCCCCCNCC(N)=O QEJUSMMBSMNFBF-UHFFFAOYSA-N 0.000 description 3
- HLDVEZAGFUBIFC-UHFFFAOYSA-N 2-(hexylamino)acetonitrile Chemical compound CCCCCCNCC#N HLDVEZAGFUBIFC-UHFFFAOYSA-N 0.000 description 3
- 108010060511 4-Aminobutyrate Transaminase Proteins 0.000 description 3
- 102100035923 4-aminobutyrate aminotransferase, mitochondrial Human genes 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 206010002660 Anoxia Diseases 0.000 description 3
- 241000976983 Anoxia Species 0.000 description 3
- 206010010904 Convulsion Diseases 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 102000005915 GABA Receptors Human genes 0.000 description 3
- 108010005551 GABA Receptors Proteins 0.000 description 3
- 206010021143 Hypoxia Diseases 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 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 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000007953 anoxia Effects 0.000 description 3
- 230000006399 behavior Effects 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 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
- 239000008120 corn starch Substances 0.000 description 3
- 230000037149 energy metabolism Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
- BKCWSIQDMQGRQU-UHFFFAOYSA-N 2-(octylamino)acetamide Chemical compound CCCCCCCCNCC(N)=O BKCWSIQDMQGRQU-UHFFFAOYSA-N 0.000 description 2
- MXZGULOAVBFAHP-UHFFFAOYSA-N 2-(pentylamino)butanenitrile Chemical compound CCCCCNC(CC)C#N MXZGULOAVBFAHP-UHFFFAOYSA-N 0.000 description 2
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 2
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 208000012661 Dyskinesia Diseases 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 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
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LHNKBXRFNPMIBR-UHFFFAOYSA-N Picrotoxin Natural products CC(C)(O)C1(O)C2OC(=O)C1C3(O)C4OC4C5C(=O)OC2C35C LHNKBXRFNPMIBR-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000001409 amidines Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 206010015037 epilepsy Diseases 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 230000003371 gabaergic effect Effects 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 235000013922 glutamic acid Nutrition 0.000 description 2
- 239000004220 glutamic acid Substances 0.000 description 2
- 229960002989 glutamic acid Drugs 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
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- VJKUPQSHOVKBCO-AHMKVGDJSA-N picrotoxin Chemical compound O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(=C)C)[C@@H]1C(=O)O2.O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(C)(O)C)[C@@H]1C(=O)O2 VJKUPQSHOVKBCO-AHMKVGDJSA-N 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 230000002295 serotoninergic effect Effects 0.000 description 2
- AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
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- 239000000454 talc Substances 0.000 description 2
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- 231100001274 therapeutic index Toxicity 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
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
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- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- DNISEZBAYYIQFB-PHDIDXHHSA-N (2r,3r)-2,3-diacetyloxybutanedioic acid Chemical compound CC(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(C)=O DNISEZBAYYIQFB-PHDIDXHHSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- YPKAPAZIJBPYCQ-UHFFFAOYSA-N 2-(heptylamino)acetamide Chemical compound CCCCCCCNCC(N)=O YPKAPAZIJBPYCQ-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- 239000003148 4 aminobutyric acid receptor blocking agent Substances 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 206010000117 Abnormal behaviour Diseases 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
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- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU81069A LU81069A1 (fr) | 1979-03-22 | 1979-03-22 | Derive de glycinamide, preparation de ce derive, son utilisation ainsi que composition contenant ce derive |
| LU81068A LU81068A1 (fr) | 1979-03-22 | 1979-03-22 | Derives de la glycinamide, leur preparation et utilisation, ainsi que compositions contenant ces derives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3010599A1 DE3010599A1 (de) | 1980-10-09 |
| DE3010599C2 true DE3010599C2 (en, 2012) | 1989-03-02 |
Family
ID=26640253
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3050800A Expired DE3050800C2 (en, 2012) | 1979-03-22 | 1980-03-20 | |
| DE19803010599 Granted DE3010599A1 (de) | 1979-03-22 | 1980-03-20 | Derivate von glycinamid, deren herstellung und verwendung |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3050800A Expired DE3050800C2 (en, 2012) | 1979-03-22 | 1980-03-20 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4639468A (en, 2012) |
| AT (1) | AT381302B (en, 2012) |
| AU (1) | AU536499B2 (en, 2012) |
| CA (1) | CA1184567A (en, 2012) |
| CH (1) | CH645091A5 (en, 2012) |
| DE (2) | DE3050800C2 (en, 2012) |
| DK (1) | DK162714C (en, 2012) |
| ES (1) | ES490536A0 (en, 2012) |
| FI (1) | FI82033C (en, 2012) |
| FR (1) | FR2451913A1 (en, 2012) |
| GB (1) | GB2048852B (en, 2012) |
| GR (1) | GR68005B (en, 2012) |
| IE (1) | IE49751B1 (en, 2012) |
| IL (1) | IL59679A (en, 2012) |
| NL (1) | NL191508C (en, 2012) |
| NO (1) | NO157817C (en, 2012) |
| PT (1) | PT70992A (en, 2012) |
| SE (1) | SE453917B (en, 2012) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2937698A1 (de) * | 1979-09-18 | 1981-04-02 | A. Nattermann & Cie GmbH, 5000 Köln | N-propionylsarcosinanilide, deren herstellungsverfahren und arzneimittel auf deren basis |
| FI832935A7 (fi) * | 1982-08-20 | 1984-02-21 | Midit | Derivat av w-aminosyror, deras framstaellning samt dessa derivat innehaollande blandningar |
| US4798687A (en) * | 1987-02-06 | 1989-01-17 | Pennwalt Corporation | 2-Amino-N-[1,2-Diphenyl-1-(thifluoromethyl)ethyl]acetamide derivatives |
| US4904681A (en) * | 1987-12-01 | 1990-02-27 | G. D. Searle & Co. | D-cycloserine and its prodrugs as cognitive enhancers |
| US4891058A (en) * | 1988-07-18 | 1990-01-02 | Ici Americas Inc. | 1-alkyl-3-aryl imidazolidine-2,4-diones and herbicidal use |
| US5278191A (en) * | 1988-08-31 | 1994-01-11 | G. D. Searle & Co. | Diphenylmethylaminoacetamide derivatives as anti-convulsants |
| US5288905A (en) * | 1988-10-07 | 1994-02-22 | G. D. Searle & Co. | Glycyl urea derivatives as anti-convulsants |
| US4944796A (en) * | 1988-11-14 | 1990-07-31 | Ici Americas Inc. | Certain 2-(disubstituted amino) acetanilide herbicides |
| DE3915755A1 (de) * | 1989-05-13 | 1990-11-29 | Bayer Ag | Fungizide mittel sowie substituierte aminosaeureamid-derivate und deren herstellung |
| IL94466A (en) * | 1989-05-25 | 1995-01-24 | Erba Carlo Spa | Pharmaceutical preparations containing the history of A-amino carboxamide N-phenylalkyl are converted into such new compounds and their preparation |
| US5075337A (en) * | 1989-07-26 | 1991-12-24 | G. D. Searle & Co. | Alpha-deuterated 2-alkylaminoacetamide derivatives having reduced toxicity for treatment of CNS disorders |
| US5153226A (en) * | 1989-08-31 | 1992-10-06 | Warner-Lambert Company | Acat inhibitors for treating hypocholesterolemia |
| DE4102042A1 (de) * | 1991-01-24 | 1992-07-30 | Bayer Ag | Substituierte aminosaeureamid-derivate deren herstellung und verwendung als fungizide |
| US5141960A (en) * | 1991-06-25 | 1992-08-25 | G. D. Searle & Co. | Tricyclic glycinamide derivatives as anti-convulsants |
| GB9306899D0 (en) * | 1993-04-01 | 1993-05-26 | Erba Carlo Spa | Substituted (arylalkylaminobenzyl) aminopropionamide derivatives and process for their preparation |
| GB9306886D0 (en) * | 1993-04-01 | 1993-05-26 | Erba Carlo Spa | Substituted (arylakoxybenzyl) aminopropanamide derivatives and process for their preparation |
| US5585358A (en) * | 1993-07-06 | 1996-12-17 | Yissum Research Development Corporation Of The Hebrew University Of Jerusalem | Derivatives of valproic acid amides and 2-valproenoic acid amides, method of making and use thereof as anticonvulsant agents |
| HUP0100815A3 (en) * | 1996-05-31 | 2002-11-28 | Allelix Neuroscience Inc South | Pharmaceutical for treatment of neurological and neuropsychiatric disorders |
| US6191165B1 (en) * | 1996-05-31 | 2001-02-20 | Allelix Neuroscience Inc. | Pharmaceutical for treatment of neurological and neuropsychiatric disorders |
| IT1283489B1 (it) * | 1996-07-23 | 1998-04-21 | Chiesi Farma Spa | Ammidi di alfa-amminoacidi,loro preparazione e loro impiego terapeutico |
| GB9727523D0 (en) | 1997-12-31 | 1998-02-25 | Pharmacia & Upjohn Spa | Alpha-aminoamide derivatives useful as analgesic agents |
| BR9909103A (pt) * | 1998-03-26 | 2001-10-16 | Univ Saskatchewan | ácidos alifático amino carboxìlico e amino fosfÈnico, amino nitrilas e amino tetrazóis como agentes de resgate celular |
| US6984754B1 (en) | 1998-03-26 | 2006-01-10 | University Of Saskatchewan Technologies Inc. | Aliphatic amino carboxylic and amino phosphonic acids amino nitriles and amino tetrazoles as cellular rescue agents |
| WO2000046183A1 (en) * | 1999-02-08 | 2000-08-10 | Checkpoint Genetics, Inc. | N-substituted amino acids, antioxidant pharmaceutical compositions containing same and methods using same |
| CA2416821A1 (en) | 2000-07-21 | 2002-01-31 | Teva Pharmaceutical Industries, Ltd. | Use of derivatives of valproic acid and 2-valproenic acid amides for the treatment of mania in bipolar disorder |
| DK1311256T3 (da) * | 2000-08-17 | 2005-11-28 | Teva Pharma | Anvendelse af derivater af valproinsyreamider og 2-valproinsyreamider til behandling eller forebyggelse af smerter og/eller hovedpinelidelser |
| WO2002042256A2 (en) * | 2000-11-21 | 2002-05-30 | Ucb, S.A. | N-alkylated gaba compounds, processes for their preparation and their use as medicaments |
| JP2004523548A (ja) | 2001-02-16 | 2004-08-05 | アレリックス ニューロサイエンス インコーポレーテッド | ＧｌｙＴ−１阻害剤 |
| US20030035784A1 (en) * | 2001-03-05 | 2003-02-20 | Kao Corporation | Hair cosmetic, aminocarboxylic acid amide and method for producing the same |
| AU2002333374B2 (en) | 2001-09-03 | 2007-03-22 | Newron Pharmaceuticals S.P.A. | Pharmaceutical composition comprising gabapentin or an analogue thereof and an (alpha)- aminoamide and its analgesic use |
| EP1438956A1 (en) * | 2003-01-16 | 2004-07-21 | Newron Pharmaceuticals S.p.A. | Alpha-aminoamide derivatives useful as antimigraine agents |
| MX2007002713A (es) * | 2004-09-10 | 2007-05-23 | Newron Pharm Spa | Uso de las (halobenciloxi) bencilamino-propanamidas para la fabricacion de medicamentos activos como moduladores selectivos de los canales de sodio y/o calcio. |
| EP1791932A1 (en) * | 2004-09-13 | 2007-06-06 | Ciba Specialty Chemicals Holding Inc. | Alkylaminoacetamide lubricant additives |
| FR2896991A1 (fr) * | 2006-02-03 | 2007-08-10 | Inst Nat Sante Rech Med | Procede pour preparer un compose organique a l'etat solide et compositions pharmaceutiques comprenant ledit compose organique |
| CN102351733B (zh) * | 2011-07-21 | 2014-03-19 | 凯莱英医药化学（阜新）技术有限公司 | 一种制备2-氨基-n,n-二甲基乙酰胺盐酸盐的方法 |
| EP4148083A1 (en) | 2014-06-25 | 2023-03-15 | Acuitas Therapeutics Inc. | Novel lipids and lipid nanoparticle formulations for delivery of nucleic acids |
| JP6053724B2 (ja) * | 2014-06-26 | 2016-12-27 | 国立大学法人九州大学 | イオン交換樹脂及び金属の吸着分離方法 |
| IL283545B2 (en) | 2015-06-29 | 2023-09-01 | Acuitas Therapeutics Inc | Lipids and nanoparticulate lipid formulations for delivery of nucleic acids |
| PL3368507T3 (pl) | 2015-10-28 | 2023-03-27 | Acuitas Therapeutics Inc. | Nowe preparaty lipidów i nanocząstek lipidowych do dostarczania kwasów nukleinowych |
| CN106187829B (zh) * | 2016-07-29 | 2017-12-15 | 万华化学集团股份有限公司 | 一种制备乙二胺基乙磺酸盐的方法 |
| US11357856B2 (en) | 2017-04-13 | 2022-06-14 | Acuitas Therapeutics, Inc. | Lipids for delivery of active agents |
| US11820728B2 (en) | 2017-04-28 | 2023-11-21 | Acuitas Therapeutics, Inc. | Carbonyl lipids and lipid nanoparticle formulations for delivery of nucleic acids |
| US11639329B2 (en) | 2017-08-16 | 2023-05-02 | Acuitas Therapeutics, Inc. | Lipids for use in lipid nanoparticle formulations |
| US11542225B2 (en) | 2017-08-17 | 2023-01-03 | Acuitas Therapeutics, Inc. | Lipids for use in lipid nanoparticle formulations |
| US11524932B2 (en) | 2017-08-17 | 2022-12-13 | Acuitas Therapeutics, Inc. | Lipids for use in lipid nanoparticle formulations |
| ES2997124T3 (en) * | 2017-08-17 | 2025-02-14 | Acuitas Therapeutics Inc | Lipids for use in lipid nanoparticle formulations |
| WO2020061426A2 (en) | 2018-09-21 | 2020-03-26 | Acuitas Therapeutics, Inc. | Systems and methods for manufacturing lipid nanoparticles and liposomes |
| KR101953366B1 (ko) | 2018-12-26 | 2019-02-28 | 정종문 | 침향을 포함하는 기억력 및 인지능력을 향상시키는 기능성 건강식품 및 이의 제조방법 |
| SG11202106987WA (en) | 2019-01-11 | 2021-07-29 | Acuitas Therapeutics Inc | Lipids for lipid nanoparticle delivery of active agents |
| USD926577S1 (en) | 2019-09-23 | 2021-08-03 | Verdant Ventures | Tamper-resistant lid assembly |
| US11326923B2 (en) | 2019-10-08 | 2022-05-10 | Verdant Ventures | Tamper-resistant lid assembly for dispensing a premeasured amount of liquid |
| EP4182297A1 (en) | 2020-07-16 | 2023-05-24 | Acuitas Therapeutics, Inc. | Cationic lipids for use in lipid nanoparticles |
| US12129223B2 (en) | 2021-12-16 | 2024-10-29 | Acuitas Therapeutics, Inc. | Lipids for use in lipid nanoparticle formulations |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2368208A (en) * | 1940-12-16 | 1945-01-30 | Emulsol Corp | Chemical compounds and method of preparing same |
| US2781385A (en) * | 1953-09-21 | 1957-02-12 | Gefgy Chemical Corp | Diamidocarboxylic acids and certain salts thereof |
| LU43649A1 (en, 2012) * | 1962-05-09 | 1963-07-16 | ||
| JPS5319654B2 (en, 2012) | 1974-03-14 | 1978-06-22 | ||
| DE2832009A1 (de) | 1978-07-20 | 1980-01-31 | Deutsches Krebsforsch | Verwendung von sarkosin und sarkosinderivaten ls tumorhemmende wirksubstanzen |
-
1980
- 1980-03-20 DE DE3050800A patent/DE3050800C2/de not_active Expired
- 1980-03-20 DE DE19803010599 patent/DE3010599A1/de active Granted
- 1980-03-21 IL IL59679A patent/IL59679A/xx unknown
- 1980-03-21 PT PT70992A patent/PT70992A/pt active IP Right Revival
- 1980-03-21 CH CH225380A patent/CH645091A5/fr not_active IP Right Cessation
- 1980-03-21 DK DK123580A patent/DK162714C/da not_active IP Right Cessation
- 1980-03-21 NO NO800830A patent/NO157817C/no unknown
- 1980-03-21 FR FR8006390A patent/FR2451913A1/fr active Granted
- 1980-03-21 SE SE8002204A patent/SE453917B/sv not_active IP Right Cessation
- 1980-03-21 FI FI800900A patent/FI82033C/fi not_active IP Right Cessation
- 1980-03-21 ES ES490536A patent/ES490536A0/es active Granted
- 1980-03-21 AT AT0154680A patent/AT381302B/de not_active IP Right Cessation
- 1980-03-22 GR GR61512A patent/GR68005B/el unknown
- 1980-03-24 NL NL8001721A patent/NL191508C/xx not_active IP Right Cessation
- 1980-03-24 IE IE599/80A patent/IE49751B1/en not_active IP Right Cessation
- 1980-03-24 GB GB8009801A patent/GB2048852B/en not_active Expired
- 1980-03-24 AU AU56784/80A patent/AU536499B2/en not_active Expired
- 1980-03-24 CA CA000348319A patent/CA1184567A/en not_active Expired
-
1985
- 1985-08-23 US US06/768,185 patent/US4639468A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL191508C (nl) | 1995-08-21 |
| IE49751B1 (en) | 1985-12-11 |
| IL59679A (en) | 1984-11-30 |
| FI82033C (fi) | 1991-01-10 |
| FI800900A7 (fi) | 1980-09-23 |
| FR2451913B1 (en, 2012) | 1984-07-13 |
| IE800599L (en) | 1980-09-22 |
| ES8104790A1 (es) | 1981-04-16 |
| NO800830L (no) | 1980-09-23 |
| NL191508B (nl) | 1995-04-18 |
| DE3050800C2 (en, 2012) | 1989-06-22 |
| IL59679A0 (en) | 1980-06-30 |
| AU536499B2 (en) | 1984-05-10 |
| FR2451913A1 (fr) | 1980-10-17 |
| ES490536A0 (es) | 1981-04-16 |
| DK123580A (da) | 1980-09-23 |
| GB2048852B (en) | 1983-03-30 |
| NO157817C (no) | 1988-05-25 |
| CH645091A5 (fr) | 1984-09-14 |
| DK162714B (da) | 1991-12-02 |
| DE3010599A1 (de) | 1980-10-09 |
| AU5678480A (en) | 1980-09-25 |
| NL8001721A (nl) | 1980-09-24 |
| DK162714C (da) | 1992-04-21 |
| AT381302B (de) | 1986-09-25 |
| ATA154680A (de) | 1986-02-15 |
| NO157817B (no) | 1988-02-15 |
| FI82033B (fi) | 1990-09-28 |
| PT70992A (fr) | 1980-04-01 |
| US4639468A (en) | 1987-01-27 |
| SE8002204L (sv) | 1980-09-23 |
| GR68005B (en, 2012) | 1981-10-26 |
| GB2048852A (en) | 1980-12-17 |
| CA1184567A (en) | 1985-03-26 |
| SE453917B (sv) | 1988-03-14 |
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