DE3202065A1 - Substituierte n-(tetrazol-5-yl)-benzoesaeureamide, ihre herstellung und diese enthaltende pharmazeutische zubereitungen - Google Patents
Substituierte n-(tetrazol-5-yl)-benzoesaeureamide, ihre herstellung und diese enthaltende pharmazeutische zubereitungenInfo
- Publication number
- DE3202065A1 DE3202065A1 DE19823202065 DE3202065A DE3202065A1 DE 3202065 A1 DE3202065 A1 DE 3202065A1 DE 19823202065 DE19823202065 DE 19823202065 DE 3202065 A DE3202065 A DE 3202065A DE 3202065 A1 DE3202065 A1 DE 3202065A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- benzoic acid
- tetrazol
- group
- vinyl
- 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.)
- Withdrawn
Links
- PLTCINJSRCMVPL-UHFFFAOYSA-N n-(2h-tetrazol-5-yl)benzamide Chemical class C=1C=CC=CC=1C(=O)NC=1N=NNN=1 PLTCINJSRCMVPL-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 10
- 206010028980 Neoplasm Diseases 0.000 abstract description 8
- 238000011282 treatment Methods 0.000 abstract description 8
- 208000002874 Acne Vulgaris Diseases 0.000 abstract description 6
- 206010000496 acne Diseases 0.000 abstract description 6
- 201000004681 Psoriasis Diseases 0.000 abstract description 4
- 208000025747 Rheumatic disease Diseases 0.000 abstract description 4
- 208000035475 disorder Diseases 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 23
- -1 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydro-naphth-7-yl Chemical group 0.000 description 16
- 229920002554 vinyl polymer Polymers 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 235000010233 benzoic acid Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000000699 topical effect Effects 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000009885 systemic effect Effects 0.000 description 4
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
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- 238000009121 systemic therapy Methods 0.000 description 3
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- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000006003 cornification Effects 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- 230000003412 degenerative effect Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000003780 keratinization Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
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- 239000002244 precipitate Substances 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
- JSDCGQYIKUYIKP-UHFFFAOYSA-N 2-(2h-tetrazol-5-yl)benzamide Chemical compound NC(=O)C1=CC=CC=C1C1=NN=NN1 JSDCGQYIKUYIKP-UHFFFAOYSA-N 0.000 description 1
- VRNHTLGHNJRHIN-UHFFFAOYSA-N 4-[2-(1,1,2,3,3,6-hexamethyl-2H-inden-5-yl)prop-1-enyl]-N-(2H-tetrazol-5-yl)benzamide Chemical compound C1=C2C(C)(C)C(C)C(C)(C)C2=CC(C)=C1C(C)=CC(C=C1)=CC=C1C(=O)NC=1N=NNN=1 VRNHTLGHNJRHIN-UHFFFAOYSA-N 0.000 description 1
- XVZQPXYEFSGPGI-UHFFFAOYSA-N 4-[2-(1,1,3,3-tetramethyl-2h-inden-5-yl)prop-1-enyl]-n-(2h-tetrazol-5-yl)benzamide Chemical compound C=1C=C(C(CC2(C)C)(C)C)C2=CC=1C(C)=CC(C=C1)=CC=C1C(=O)NC1=NN=NN1 XVZQPXYEFSGPGI-UHFFFAOYSA-N 0.000 description 1
- RXDHMEODCSIGPS-UHFFFAOYSA-N 4-[2-(5,5,8,8-tetramethyl-3-propyl-6,7-dihydronaphthalen-2-yl)prop-1-enyl]-n-(2h-tetrazol-5-yl)benzamide Chemical compound CCCC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(C)=CC(C=C1)=CC=C1C(=O)NC1=NN=NN1 RXDHMEODCSIGPS-UHFFFAOYSA-N 0.000 description 1
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000002346 musculoskeletal system Anatomy 0.000 description 1
- 230000009826 neoplastic cell growth Effects 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000004633 phorbol derivatives Chemical class 0.000 description 1
- 239000002644 phorbol ester Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940066769 systemic antihistamines substituted alkylamines Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/66—Polycyclic acids with unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
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)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823202065 DE3202065A1 (de) | 1982-01-23 | 1982-01-23 | Substituierte n-(tetrazol-5-yl)-benzoesaeureamide, ihre herstellung und diese enthaltende pharmazeutische zubereitungen |
| EP82111928A EP0084667B1 (de) | 1982-01-23 | 1982-12-23 | Phenylethylen-Derivate, ihre Herstellung und Verwendung als Arzneimittel |
| AT82111928T ATE15647T1 (de) | 1982-01-23 | 1982-12-23 | Phenylethylen-derivate, ihre herstellung und verwendung als arzneimittel. |
| DE8282111928T DE3266442D1 (en) | 1982-01-23 | 1982-12-23 | Phenylethylene derivatives, their preparation and use as medicines |
| IL67618A IL67618A0 (en) | 1982-01-23 | 1983-01-04 | Phenylethylene derivatives,their preparation and pharmaceutical compositions containing them |
| CA000419140A CA1183541A (en) | 1982-01-23 | 1983-01-10 | Phenylethylene derivatives, their preparation and their use as drugs |
| FI830163A FI830163A7 (fi) | 1982-01-23 | 1983-01-18 | Fenyylietyleeni-johdannaisia, niiden valmistus ja käyttö lääkeaineina. |
| JP596683A JPS58128340A (ja) | 1982-01-23 | 1983-01-19 | フェニルエチレン誘導体及びその製法 |
| AU10695/83A AU1069583A (en) | 1982-01-23 | 1983-01-21 | Phenylethylene derivatives |
| NO830202A NO830202L (no) | 1982-01-23 | 1983-01-21 | Fremgangsmaate for fremstilling av terapeutisk aktive fenyletylen-derivater |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823202065 DE3202065A1 (de) | 1982-01-23 | 1982-01-23 | Substituierte n-(tetrazol-5-yl)-benzoesaeureamide, ihre herstellung und diese enthaltende pharmazeutische zubereitungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3202065A1 true DE3202065A1 (de) | 1983-08-04 |
Family
ID=6153722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823202065 Withdrawn DE3202065A1 (de) | 1982-01-23 | 1982-01-23 | Substituierte n-(tetrazol-5-yl)-benzoesaeureamide, ihre herstellung und diese enthaltende pharmazeutische zubereitungen |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS58128340A (enrdf_load_stackoverflow) |
| DE (1) | DE3202065A1 (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0135032A1 (en) * | 1983-07-22 | 1985-03-27 | Merrell Dow Pharmaceuticals Inc. | Carbamates and oxalyl amides of amino-N-(1H-tetrazol-5-yl) benzamides |
| US4806558A (en) * | 1984-09-22 | 1989-02-21 | Basf Aktiengesellschaft | Diarylacetylenes and their use in treating acne |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6122046A (ja) * | 1984-07-07 | 1986-01-30 | Koichi Shiyudo | スチルベン誘導体 |
| JPS6122047A (ja) * | 1984-07-07 | 1986-01-30 | Koichi Shiyudo | 安息香酸誘導体 |
| JPS6176440A (ja) * | 1984-09-19 | 1986-04-18 | Koichi Shiyudo | 安息香酸誘導体 |
| DE3434942A1 (de) * | 1984-09-22 | 1986-04-03 | Basf Ag, 6700 Ludwigshafen | Tetralin-derivate, ihre herstellung und verwendung |
| CA1298309C (en) * | 1987-11-06 | 1992-03-31 | Michael Klaus | Benzocycloheptene derivatives |
| CA2611684A1 (en) * | 2005-06-30 | 2007-01-11 | Wisconsin Alumni Research Foundation | A-[(e)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-napthalenyl)-1-propenyl]benzoic acid analogs and method of manufacture and use thereof |
-
1982
- 1982-01-23 DE DE19823202065 patent/DE3202065A1/de not_active Withdrawn
-
1983
- 1983-01-19 JP JP596683A patent/JPS58128340A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0135032A1 (en) * | 1983-07-22 | 1985-03-27 | Merrell Dow Pharmaceuticals Inc. | Carbamates and oxalyl amides of amino-N-(1H-tetrazol-5-yl) benzamides |
| US4806558A (en) * | 1984-09-22 | 1989-02-21 | Basf Aktiengesellschaft | Diarylacetylenes and their use in treating acne |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0512336B2 (enrdf_load_stackoverflow) | 1993-02-17 |
| JPS58128340A (ja) | 1983-07-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |