DE1518125C3 - Asparaginsäure- und Glutaminsaureamide, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel - Google Patents
Asparaginsäure- und Glutaminsaureamide, Verfahren zu deren Herstellung und diese enthaltende ArzneimittelInfo
- Publication number
- DE1518125C3 DE1518125C3 DE1965R0041204 DER0041204A DE1518125C3 DE 1518125 C3 DE1518125 C3 DE 1518125C3 DE 1965R0041204 DE1965R0041204 DE 1965R0041204 DE R0041204 A DER0041204 A DE R0041204A DE 1518125 C3 DE1518125 C3 DE 1518125C3
- Authority
- DE
- Germany
- Prior art keywords
- anhydride
- acid
- stirring
- benzoyl
- glutamic acid
- 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
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 title claims description 7
- 239000004220 glutamic acid Substances 0.000 title claims description 7
- 235000013922 glutamic acid Nutrition 0.000 title claims description 7
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 title claims description 3
- 235000003704 aspartic acid Nutrition 0.000 title claims description 3
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 title claims description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 title claims 2
- 238000000034 method Methods 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 5
- 239000003814 drug Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 description 27
- 238000003756 stirring Methods 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 150000008064 anhydrides Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- WHUUTDBJXJRKMK-GSVOUGTGSA-N D-glutamic acid Chemical compound OC(=O)[C@H](N)CCC(O)=O WHUUTDBJXJRKMK-GSVOUGTGSA-N 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- 230000001262 anti-secretory effect Effects 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical group 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- LPJXPACOXRZCCP-VIFPVBQESA-N (2s)-2-benzamidopentanedioic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)NC(=O)C1=CC=CC=C1 LPJXPACOXRZCCP-VIFPVBQESA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- DCTUUCZNZUBHIZ-UHFFFAOYSA-N C1(=CC=CC=C1)CC(=O)NC1CCC(=O)OC1=O Chemical compound C1(=CC=CC=C1)CC(=O)NC1CCC(=O)OC1=O DCTUUCZNZUBHIZ-UHFFFAOYSA-N 0.000 description 5
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000002911 mydriatic effect Effects 0.000 description 5
- YSVIOFKUOBVJII-UHFFFAOYSA-N n-(2,5-dioxooxolan-3-yl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC1CC(=O)OC1=O YSVIOFKUOBVJII-UHFFFAOYSA-N 0.000 description 5
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- HOBWAPHTEJGALG-JKCMADFCSA-N [(1r,5s)-8-methyl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate;sulfate Chemical compound [O-]S([O-])(=O)=O.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1 HOBWAPHTEJGALG-JKCMADFCSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229960002028 atropine sulfate Drugs 0.000 description 3
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 230000003248 secreting effect Effects 0.000 description 3
- 231100001274 therapeutic index Toxicity 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- DJLTZJGULPLVOA-QMMMGPOBSA-N (2s)-2-benzamidobutanedioic acid Chemical group OC(=O)C[C@@H](C(O)=O)NC(=O)C1=CC=CC=C1 DJLTZJGULPLVOA-QMMMGPOBSA-N 0.000 description 2
- RFWFOJDAIRDAPK-VKHMYHEASA-N (3s)-3-aminooxane-2,6-dione Chemical compound N[C@H]1CCC(=O)OC1=O RFWFOJDAIRDAPK-VKHMYHEASA-N 0.000 description 2
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N 4-aminoantipyrine Chemical compound CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 2
- 229930003347 Atropine Natural products 0.000 description 2
- CDJDAEGLIIHJLE-UHFFFAOYSA-N C(C)(=O)N(C1CC(=O)OC1=O)C1=CC=CC=C1 Chemical compound C(C)(=O)N(C1CC(=O)OC1=O)C1=CC=CC=C1 CDJDAEGLIIHJLE-UHFFFAOYSA-N 0.000 description 2
- 229930182847 D-glutamic acid Natural products 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 208000008469 Peptic Ulcer Diseases 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229960000396 atropine Drugs 0.000 description 2
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- MYBJHWJWVVIFAO-UHFFFAOYSA-N n-(2,6-dioxooxan-3-yl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC1CCC(=O)OC1=O MYBJHWJWVVIFAO-UHFFFAOYSA-N 0.000 description 2
- MYBJHWJWVVIFAO-VIFPVBQESA-N n-[(3s)-2,6-dioxooxan-3-yl]benzamide Chemical compound C=1C=CC=CC=1C(=O)N[C@H]1CCC(=O)OC1=O MYBJHWJWVVIFAO-VIFPVBQESA-N 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- -1 phenylacetyl Chemical group 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000006340 racemization Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 1
- PTSRBZOZSRJCKX-UHFFFAOYSA-N 2-[(2-phenylacetyl)amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NC(=O)CC1=CC=CC=C1 PTSRBZOZSRJCKX-UHFFFAOYSA-N 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
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 101100162210 Aspergillus parasiticus (strain ATCC 56775 / NRRL 5862 / SRRC 143 / SU-1) aflM gene Proteins 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 101100102500 Caenorhabditis elegans ver-1 gene Proteins 0.000 description 1
- DHUZAAUGHUHIDS-ONEGZZNKSA-N Isomyristicin Chemical compound COC1=CC(\C=C\C)=CC2=C1OCO2 DHUZAAUGHUHIDS-ONEGZZNKSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
- SVFKZPQPMMZHLZ-UHFFFAOYSA-N N-Phenylacetylaspartic acid Chemical compound OC(=O)CC(C(O)=O)NC(=O)CC1=CC=CC=C1 SVFKZPQPMMZHLZ-UHFFFAOYSA-N 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- 239000008896 Opium Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
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- 208000025865 Ulcer Diseases 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
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- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- GERIGMSHTUAXSI-UHFFFAOYSA-N bis(8-methyl-8-azabicyclo[3.2.1]octan-3-yl) 4-phenyl-2,3-dihydro-1h-naphthalene-1,4-dicarboxylate Chemical compound CN1C(C2)CCC1CC2OC(=O)C(C1=CC=CC=C11)CCC1(C(=O)OC1CC2CCC(N2C)C1)C1=CC=CC=C1 GERIGMSHTUAXSI-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
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- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
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- YSVIOFKUOBVJII-QMMMGPOBSA-N n-[(3s)-2,5-dioxooxolan-3-yl]benzamide Chemical group C=1C=CC=CC=1C(=O)N[C@H]1CC(=O)OC1=O YSVIOFKUOBVJII-QMMMGPOBSA-N 0.000 description 1
- XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 1
- GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
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- 229960005439 propantheline bromide Drugs 0.000 description 1
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- 239000002904 solvent Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000002731 stomach secretion inhibitor Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- VFEDLMLHAGASHB-UHFFFAOYSA-M tridihexethyl iodide Chemical compound [I-].C=1C=CC=CC=1C(O)(CC[N+](CC)(CC)CC)C1CCCCC1 VFEDLMLHAGASHB-UHFFFAOYSA-M 0.000 description 1
- 229950008407 tridihexethyl iodide Drugs 0.000 description 1
- 230000001228 trophic effect Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1675864 | 1964-07-31 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1518125A1 DE1518125A1 (de) | 1969-06-12 |
| DE1518125B2 DE1518125B2 (de) | 1977-07-28 |
| DE1518125C3 true DE1518125C3 (de) | 1978-03-23 |
Family
ID=11149303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1965R0041204 Expired DE1518125C3 (de) | 1964-07-31 | 1965-07-30 | Asparaginsäure- und Glutaminsaureamide, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE667776A (enExample) |
| CH (1) | CH472380A (enExample) |
| DE (1) | DE1518125C3 (enExample) |
| DK (1) | DK131282B (enExample) |
| ES (1) | ES315993A1 (enExample) |
| FI (1) | FI44616C (enExample) |
| FR (2) | FR1555468A (enExample) |
| GB (1) | GB1108819A (enExample) |
| SE (1) | SE345659B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO131985C (enExample) * | 1970-06-05 | 1975-09-03 | Kyowa Hakko Kogyo Kk | |
| IT1215169B (it) * | 1985-12-17 | 1990-01-31 | Rotta Research Lab | Derivati alchil ossigenati degli acidi glutammico ed aspartico ad attivita antagonista su polipeptidi bioattivi e procedimento per la loro preparazione |
| US5105007A (en) * | 1987-10-19 | 1992-04-14 | Abbott Laboratories | Phenylacetylglutamine (PAG) analytical test |
| WO2007008994A2 (en) | 2005-07-11 | 2007-01-18 | Wyeth | Glutamate aggrecanase inhibitors |
| KR20080058436A (ko) | 2005-10-13 | 2008-06-25 | 와이어쓰 | 글루탐산 유도체의 제조 방법 |
| CN101784516B (zh) * | 2007-06-13 | 2014-07-02 | 百时美施贵宝公司 | 作为凝血因子抑制剂的二肽类似物 |
-
1965
- 1965-07-26 GB GB3190365A patent/GB1108819A/en not_active Expired
- 1965-07-28 CH CH1063665A patent/CH472380A/it not_active IP Right Cessation
- 1965-07-30 SE SE1005665A patent/SE345659B/xx unknown
- 1965-07-30 ES ES0315993A patent/ES315993A1/es not_active Expired
- 1965-07-30 FI FI185165A patent/FI44616C/fi active
- 1965-07-30 DE DE1965R0041204 patent/DE1518125C3/de not_active Expired
- 1965-07-30 DK DK394265A patent/DK131282B/da unknown
- 1965-07-31 FR FR1555468D patent/FR1555468A/fr not_active Expired
- 1965-07-31 FR FR26835A patent/FR5853M/fr not_active Expired
- 1965-08-02 BE BE667776A patent/BE667776A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR1555468A (enExample) | 1969-01-31 |
| ES315993A1 (es) | 1966-04-16 |
| DE1518125A1 (de) | 1969-06-12 |
| FI44616C (fi) | 1971-12-10 |
| DE1518125B2 (de) | 1977-07-28 |
| CH472380A (it) | 1969-05-15 |
| GB1108819A (en) | 1968-04-03 |
| DK131282B (da) | 1975-06-23 |
| DK131282C (enExample) | 1975-11-24 |
| BE667776A (enExample) | 1965-12-01 |
| FR5853M (enExample) | 1968-03-11 |
| FI44616B (enExample) | 1971-08-31 |
| SE345659B (enExample) | 1972-06-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |