DE2526092C2 - Aminobenzoesäurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel - Google Patents
Aminobenzoesäurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende ArzneimittelInfo
- Publication number
- DE2526092C2 DE2526092C2 DE2526092A DE2526092A DE2526092C2 DE 2526092 C2 DE2526092 C2 DE 2526092C2 DE 2526092 A DE2526092 A DE 2526092A DE 2526092 A DE2526092 A DE 2526092A DE 2526092 C2 DE2526092 C2 DE 2526092C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- chloranthranilic
- compounds
- carboxy
- carboxyphenyl
- 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
- 150000005417 aminobenzoic acid derivatives Chemical class 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 title description 28
- 238000000034 method Methods 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 4
- 239000003814 drug Substances 0.000 title description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 238000012360 testing method Methods 0.000 description 19
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 18
- ATCRIUVQKHMXSH-UHFFFAOYSA-N 2,4-dichlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1Cl ATCRIUVQKHMXSH-UHFFFAOYSA-N 0.000 description 14
- 241000700159 Rattus Species 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 10
- 210000004185 liver Anatomy 0.000 description 10
- 206010070834 Sensitisation Diseases 0.000 description 9
- 210000004369 blood Anatomy 0.000 description 9
- 239000008280 blood Substances 0.000 description 9
- 230000008313 sensitization Effects 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 description 7
- -1 alkali metal salts Chemical class 0.000 description 7
- 239000002504 physiological saline solution Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UGDPYGKWIHHBMB-UHFFFAOYSA-N lobenzarit Chemical compound OC(=O)C1=CC=CC=C1NC1=CC(Cl)=CC=C1C(O)=O UGDPYGKWIHHBMB-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 5
- MOFVSTNWEDAEEK-UHFFFAOYSA-M indocyanine green Chemical compound [Na+].[O-]S(=O)(=O)CCCCN1C2=CC=C3C=CC=CC3=C2C(C)(C)C1=CC=CC=CC=CC1=[N+](CCCCS([O-])(=O)=O)C2=CC=C(C=CC=C3)C3=C2C1(C)C MOFVSTNWEDAEEK-UHFFFAOYSA-M 0.000 description 5
- 229960004657 indocyanine green Drugs 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 5
- BIECFEMCDBQPTL-UHFFFAOYSA-N 2-(chloroamino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NCl BIECFEMCDBQPTL-UHFFFAOYSA-N 0.000 description 4
- VEXDRERIMPLZLU-UHFFFAOYSA-N 3-hydroxy-2-methylbutanoic acid Chemical compound CC(O)C(C)C(O)=O VEXDRERIMPLZLU-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000005415 aminobenzoic acids Chemical class 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- GHAFORRTMVIXHS-UHFFFAOYSA-L bromosulfophthalein sodium Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(O)=CC=C1C1(C=2C=C(C(O)=CC=2)S([O-])(=O)=O)C(C(Br)=C(Br)C(Br)=C2Br)=C2C(=O)O1 GHAFORRTMVIXHS-UHFFFAOYSA-L 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229960001734 sulfobromophthalein Drugs 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 210000003462 vein Anatomy 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000013223 sprague-dawley female rat Methods 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- WCQWHIQTMOQESA-UHFFFAOYSA-N 2-(2-carboxy-5-chloroanilino)-3,6-dimethylbenzoic acid Chemical compound CC1=CC=C(C)C(C(O)=O)=C1NC1=CC(Cl)=CC=C1C(O)=O WCQWHIQTMOQESA-UHFFFAOYSA-N 0.000 description 2
- XKWSWTGIYFVVHP-UHFFFAOYSA-N 2-(2-carboxy-5-chloroanilino)-3-methylbenzoic acid Chemical compound CC1=CC=CC(C(O)=O)=C1NC1=CC(Cl)=CC=C1C(O)=O XKWSWTGIYFVVHP-UHFFFAOYSA-N 0.000 description 2
- BRZWMBWCBDGKTP-UHFFFAOYSA-N 2-(2-carboxy-5-chloroanilino)-5-methylbenzoic acid Chemical compound OC(=O)C1=CC(C)=CC=C1NC1=CC(Cl)=CC=C1C(O)=O BRZWMBWCBDGKTP-UHFFFAOYSA-N 0.000 description 2
- WNAJXPYVTFYEST-UHFFFAOYSA-N 2-Amino-3-methylbenzoate Chemical compound CC1=CC=CC(C(O)=O)=C1N WNAJXPYVTFYEST-UHFFFAOYSA-N 0.000 description 2
- PFKMPZBEUUAELA-UHFFFAOYSA-N 2-amino-3,6-dimethylbenzoic acid Chemical compound CC1=CC=C(C)C(C(O)=O)=C1N PFKMPZBEUUAELA-UHFFFAOYSA-N 0.000 description 2
- JYYLQSCZISREGY-UHFFFAOYSA-N 2-amino-4-chlorobenzoic acid Chemical compound NC1=CC(Cl)=CC=C1C(O)=O JYYLQSCZISREGY-UHFFFAOYSA-N 0.000 description 2
- NBUUUJWWOARGNW-UHFFFAOYSA-N 2-amino-5-methylbenzoic acid Chemical compound CC1=CC=C(N)C(C(O)=O)=C1 NBUUUJWWOARGNW-UHFFFAOYSA-N 0.000 description 2
- UAGUNISKDDCZSS-UHFFFAOYSA-N 3-chloro-2,1-benzoxazole Chemical compound C1=CC=CC2=C(Cl)ON=C21 UAGUNISKDDCZSS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 206010018910 Haemolysis Diseases 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
- YTGJWQPHMWSCST-UHFFFAOYSA-N Tiopronin Chemical compound CC(S)C(=O)NCC(O)=O YTGJWQPHMWSCST-UHFFFAOYSA-N 0.000 description 2
- 108010058907 Tiopronin Proteins 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 210000000941 bile Anatomy 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000008588 hemolysis Effects 0.000 description 2
- 230000000091 immunopotentiator Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- NAGGYODWMPFKJQ-UHFFFAOYSA-N 2,4-dibromobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1Br NAGGYODWMPFKJQ-UHFFFAOYSA-N 0.000 description 1
- HLDPGVRFMBHZCE-UHFFFAOYSA-N 2-(2-carboxy-4-chloroanilino)-4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=C(Cl)C=C1C(O)=O HLDPGVRFMBHZCE-UHFFFAOYSA-N 0.000 description 1
- ZWFJUPLDDJOCRG-UHFFFAOYSA-N 2-(2-carboxy-5-chloroanilino)-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C(NC=2C(=CC=C(Cl)C=2)C(O)=O)=C1 ZWFJUPLDDJOCRG-UHFFFAOYSA-N 0.000 description 1
- OFIKQKCNUVWFGP-UHFFFAOYSA-N 2-(2-carboxyanilino)-4-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC(C(F)(F)F)=CC=C1C(O)=O OFIKQKCNUVWFGP-UHFFFAOYSA-N 0.000 description 1
- QOEXHMFHEJIEFH-UHFFFAOYSA-N 2-(2-carboxyanilino)-4-chloro-3-methylbenzoic acid Chemical compound CC1=C(Cl)C=CC(C(O)=O)=C1NC1=CC=CC=C1C(O)=O QOEXHMFHEJIEFH-UHFFFAOYSA-N 0.000 description 1
- KYVWNCQWQGNPFL-UHFFFAOYSA-N 2-(2-carboxyanilino)-5-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=C(Cl)C=C1C(O)=O KYVWNCQWQGNPFL-UHFFFAOYSA-N 0.000 description 1
- KLVTUYAKQNFRLK-UHFFFAOYSA-N 2-(2-carboxyanilino)-5-methylbenzoic acid Chemical compound OC(=O)C1=CC(C)=CC=C1NC1=CC=CC=C1C(O)=O KLVTUYAKQNFRLK-UHFFFAOYSA-N 0.000 description 1
- WZRGSAMJPMZXCO-UHFFFAOYSA-N 2-(3-carboxyanilino)-4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(NC=2C(=CC=C(Cl)C=2)C(O)=O)=C1 WZRGSAMJPMZXCO-UHFFFAOYSA-N 0.000 description 1
- AYFCJSDUMVUODG-UHFFFAOYSA-N 2-(4-carboxyanilino)-4-chlorobenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=CC(Cl)=CC=C1C(O)=O AYFCJSDUMVUODG-UHFFFAOYSA-N 0.000 description 1
- UJRYLIKAXUSWFS-UHFFFAOYSA-N 2-amino-4-chloro-3-methylbenzoic acid Chemical compound CC1=C(Cl)C=CC(C(O)=O)=C1N UJRYLIKAXUSWFS-UHFFFAOYSA-N 0.000 description 1
- IFXKXCLVKQVVDI-UHFFFAOYSA-N 2-amino-5-chlorobenzoic acid Chemical compound NC1=CC=C(Cl)C=C1C(O)=O IFXKXCLVKQVVDI-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 208000009386 Experimental Arthritis Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 241001494479 Pecora Species 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- 230000000240 adjuvant effect Effects 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000007969 cellular immunity Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940116318 copper carbonate Drugs 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000016784 immunoglobulin production Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000528 statistical test Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2526092A DE2526092C2 (de) | 1975-06-11 | 1975-06-11 | Aminobenzoesäurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| JP51041041A JPS606355B2 (ja) | 1975-06-11 | 1976-04-12 | 新規アミノ安息香酸誘導体、その製法及び医薬組成物 |
| US05/691,432 US4092426A (en) | 1975-06-11 | 1976-06-01 | Novel aminobenzoic acid derivatives, process for preparing the same and pharmaceutical composition containing the same |
| HU76CU152A HU176505B (en) | 1975-06-11 | 1976-06-03 | Process for producing new n-bracket-2-comma above-carboxy-phenyl-bracket closed-4-chloro-antranylic acid derivatives |
| GB23299/76A GB1520179A (en) | 1975-06-11 | 1976-06-04 | Aminobenzoic acid derivatives process for preparing the same and pharmaceutical composition containing the same |
| SE7606592A SE412907B (sv) | 1975-06-11 | 1976-06-10 | Forfarande for framstellning av nya n-2'-karboxifenyl-4-klorantranilsyror |
| CH738076A CH630605A5 (de) | 1975-06-11 | 1976-06-10 | Verfahren zur herstellung von neuen aminobenzoesaeure-derivaten und so hergestellte aminobenzoesaeure-derivate. |
| ES448761A ES448761A1 (es) | 1975-06-11 | 1976-06-10 | Un procedimiento para la preparacion de un derivado de acidoaminobenzoico. |
| CA254,544A CA1066303A (en) | 1975-06-11 | 1976-06-10 | Aminobenzoic acid derivatives, process for preparing the same and pharmaceutical composition containing the same |
| BE2055116A BE842832A (fr) | 1975-06-11 | 1976-06-11 | Nouveaux derives de l'acide aminobenzoique, procede pour leur preparation et composition pharmaceutique en contenant |
| FR7617799A FR2313921A1 (fr) | 1975-06-11 | 1976-06-11 | Nouveaux derives de l'acide aminobenzoique, leur procede de preparation et leur application |
| FI761677A FI62283C (fi) | 1975-06-11 | 1976-06-11 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara n-2'-karboxifenyl-4-klorantranilsyraderivat |
| CS763889A CS210659B2 (en) | 1975-06-11 | 1976-06-11 | Method of preparation of amidobenzoic acid derivatives |
| NLAANVRAGE7606309,A NL185405C (nl) | 1975-06-11 | 1976-06-11 | Werkwijze voor de bereiding van een farmaceutisch preparaat, alsmede werkwijze voor de bereiding van een 2-(2-carboxyfenylamino)benzoezuur derivaat. |
| AR21281478D AR212814A1 (es) | 1975-06-11 | 1978-01-01 | Procedimiento de preparacion de derivados de acido n-2'-carboxifenil-4-cloroantranilico |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2526092A DE2526092C2 (de) | 1975-06-11 | 1975-06-11 | Aminobenzoesäurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2526092A1 DE2526092A1 (de) | 1976-12-30 |
| DE2526092C2 true DE2526092C2 (de) | 1983-12-01 |
Family
ID=5948845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2526092A Expired DE2526092C2 (de) | 1975-06-11 | 1975-06-11 | Aminobenzoesäurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS606355B2 (cs) |
| BE (1) | BE842832A (cs) |
| CS (1) | CS210659B2 (cs) |
| DE (1) | DE2526092C2 (cs) |
| HU (1) | HU176505B (cs) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5791914A (en) | 1980-11-28 | 1982-06-08 | Chugai Pharmaceut Co Ltd | Peptic unti-ulcer |
| JPS57123152A (en) * | 1981-01-26 | 1982-07-31 | Chugai Pharmaceut Co Ltd | Novel aminobenzoic acid derivative and drug composition |
| HU184479B (en) * | 1981-08-28 | 1984-08-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing n-bracket-2-carboxyphenyl-bracket closed-4-chloro-anthranylis acid |
| JPH0370342A (ja) * | 1989-08-10 | 1991-03-26 | Sanyo Electric Co Ltd | 無線電話装置 |
| DE19532054A1 (de) * | 1995-08-31 | 1997-03-06 | Hoechst Ag | Verfahren zur Herstellung von N-Carboxymethylen-4-chlor-anthranilsäure, sowie deren Dialkylestern |
| JP4190019B2 (ja) | 2006-09-12 | 2008-12-03 | 日本航空電子工業株式会社 | コネクタ |
| JP5838055B2 (ja) | 2011-07-27 | 2015-12-24 | 矢崎総業株式会社 | レセプタクルコネクタ |
-
1975
- 1975-06-11 DE DE2526092A patent/DE2526092C2/de not_active Expired
-
1976
- 1976-04-12 JP JP51041041A patent/JPS606355B2/ja not_active Expired
- 1976-06-03 HU HU76CU152A patent/HU176505B/hu unknown
- 1976-06-11 CS CS763889A patent/CS210659B2/cs unknown
- 1976-06-11 BE BE2055116A patent/BE842832A/xx not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| HU176505B (en) | 1981-03-28 |
| JPS606355B2 (ja) | 1985-02-18 |
| JPS5212141A (en) | 1977-01-29 |
| DE2526092A1 (de) | 1976-12-30 |
| CS210659B2 (en) | 1982-01-29 |
| BE842832A (fr) | 1976-10-01 |
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Ipc: C07C101/54 |
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