DE2132987A1 - N-Benzyl-3-sulfamoylebenzamide und deren pharmakologisch vertraegliche Salze - Google Patents
N-Benzyl-3-sulfamoylebenzamide und deren pharmakologisch vertraegliche SalzeInfo
- Publication number
- DE2132987A1 DE2132987A1 DE19712132987 DE2132987A DE2132987A1 DE 2132987 A1 DE2132987 A1 DE 2132987A1 DE 19712132987 DE19712132987 DE 19712132987 DE 2132987 A DE2132987 A DE 2132987A DE 2132987 A1 DE2132987 A1 DE 2132987A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- methyl
- methylbenzyl
- solution
- room temperature
- 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.)
- Pending
Links
- 150000003839 salts Chemical class 0.000 title claims description 5
- -1 methyl sulfamoyl Chemical group 0.000 claims description 24
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 229910052801 chlorine Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- 239000000203 mixture Substances 0.000 description 35
- 239000000243 solution Substances 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000007787 solid Substances 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- NAETXYOXMDYNLE-UHFFFAOYSA-N 3-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC=CC(C(O)=O)=C1 NAETXYOXMDYNLE-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 241000700605 Viruses Species 0.000 description 6
- 239000012265 solid product Substances 0.000 description 6
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 5
- WECBWHORECBJKQ-UHFFFAOYSA-N 4-bromo-3-(methylsulfamoyl)benzoic acid Chemical compound CNS(=O)(=O)C1=CC(C(O)=O)=CC=C1Br WECBWHORECBJKQ-UHFFFAOYSA-N 0.000 description 5
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 5
- 230000000120 cytopathologic effect Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- OWBBPHXIAFVUMO-UHFFFAOYSA-N 3-chlorosulfonyl-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1S(Cl)(=O)=O OWBBPHXIAFVUMO-UHFFFAOYSA-N 0.000 description 4
- 241000709661 Enterovirus Species 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XVAASXODNQTGCP-UHFFFAOYSA-N 3-chlorosulfonyl-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1S(Cl)(=O)=O XVAASXODNQTGCP-UHFFFAOYSA-N 0.000 description 3
- CKCJWLSXMXMIQO-UHFFFAOYSA-N 4-methoxy-3-sulfamoylbenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1S(N)(=O)=O CKCJWLSXMXMIQO-UHFFFAOYSA-N 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- UVXUVTAWEUNUAK-UHFFFAOYSA-N n-benzyl-3-sulfamoylbenzamide Chemical class NS(=O)(=O)C1=CC=CC(C(=O)NCC=2C=CC=CC=2)=C1 UVXUVTAWEUNUAK-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- MDITWYHGSGANSP-UHFFFAOYSA-N 4-bromo-3-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C(S(Cl)(=O)=O)=C1 MDITWYHGSGANSP-UHFFFAOYSA-N 0.000 description 2
- SHSGDXCJYVZFTP-UHFFFAOYSA-N 4-ethoxybenzoic acid Chemical compound CCOC1=CC=C(C(O)=O)C=C1 SHSGDXCJYVZFTP-UHFFFAOYSA-N 0.000 description 2
- LAWXHQQGKPFVPA-UHFFFAOYSA-N 4-methoxy-3-(methylsulfamoyl)benzamide Chemical compound CNS(=O)(=O)C1=CC(C(N)=O)=CC=C1OC LAWXHQQGKPFVPA-UHFFFAOYSA-N 0.000 description 2
- XKBCISMVWOJEGS-UHFFFAOYSA-N 4-methoxy-3-(methylsulfamoyl)benzoic acid Chemical compound CNS(=O)(=O)C1=CC(C(O)=O)=CC=C1OC XKBCISMVWOJEGS-UHFFFAOYSA-N 0.000 description 2
- CSCIPOYOCZTZBR-UHFFFAOYSA-N 4-methyl-2-(methylsulfamoyl)benzoic acid Chemical compound CNS(=O)(=O)C1=CC(C)=CC=C1C(O)=O CSCIPOYOCZTZBR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- 239000002831 pharmacologic agent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- LMRKXSDOAFUINK-UHFFFAOYSA-N 3-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=CC=CC(S(Cl)(=O)=O)=C1 LMRKXSDOAFUINK-UHFFFAOYSA-N 0.000 description 1
- CLICAYDHIJRPTL-UHFFFAOYSA-N 3-sulfamoylbenzoyl chloride Chemical class NS(=O)(=O)C1=CC=CC(C(Cl)=O)=C1 CLICAYDHIJRPTL-UHFFFAOYSA-N 0.000 description 1
- GIMVMSKAMDJCOO-UHFFFAOYSA-N 4-bromo-3-(methylsulfamoyl)benzoyl chloride Chemical compound BrC1=C(C=C(C(=O)Cl)C=C1)S(NC)(=O)=O GIMVMSKAMDJCOO-UHFFFAOYSA-N 0.000 description 1
- MJTAWGWKLXMOCO-UHFFFAOYSA-N 4-bromo-3-sulfamoylbenzoyl chloride Chemical compound NS(=O)(=O)C1=CC(C(Cl)=O)=CC=C1Br MJTAWGWKLXMOCO-UHFFFAOYSA-N 0.000 description 1
- TUXYZHVUPGXXQG-UHFFFAOYSA-N 4-bromobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-N 0.000 description 1
- GUCPYIYFQVTFSI-UHFFFAOYSA-N 4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1 GUCPYIYFQVTFSI-UHFFFAOYSA-N 0.000 description 1
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000034712 Rickettsia Infections Diseases 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 229940054066 benzamide antipsychotics Drugs 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- SJYZEMGBGPSNNJ-UHFFFAOYSA-N n-(methylsulfamoyl)benzamide Chemical compound CNS(=O)(=O)NC(=O)C1=CC=CC=C1 SJYZEMGBGPSNNJ-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- NASFKTWZWDYFER-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na] NASFKTWZWDYFER-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000013026 undiluted sample Substances 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5268870A | 1970-07-06 | 1970-07-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2132987A1 true DE2132987A1 (de) | 1972-01-20 |
Family
ID=21979259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712132987 Pending DE2132987A1 (de) | 1970-07-06 | 1971-07-02 | N-Benzyl-3-sulfamoylebenzamide und deren pharmakologisch vertraegliche Salze |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5220990B1 (https=) |
| DE (1) | DE2132987A1 (https=) |
| FR (1) | FR2100862B1 (https=) |
| GB (1) | GB1328169A (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0636458U (ja) * | 1992-10-23 | 1994-05-17 | 株式会社トヨハン | 生花支持器具 |
| WO2006044645A2 (en) * | 2004-10-13 | 2006-04-27 | Adolor Corporation | Sulfamoyl benzamides and methods of their use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1267777A (fr) * | 1959-03-03 | 1961-07-28 | Geigy Ag J R | Nouveaux sulfamyl-benzamides et leur préparation |
| FR1450358A (fr) * | 1960-09-03 | 1966-06-24 | Parke Davis & Co | Production de 4-halogéno-3-sulfamylbenzamides nouvelles |
-
1971
- 1971-07-02 FR FR7124309A patent/FR2100862B1/fr not_active Expired
- 1971-07-02 JP JP46048158A patent/JPS5220990B1/ja active Pending
- 1971-07-02 GB GB3119971A patent/GB1328169A/en not_active Expired
- 1971-07-02 DE DE19712132987 patent/DE2132987A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5220990B1 (https=) | 1977-06-07 |
| FR2100862A1 (https=) | 1972-03-24 |
| FR2100862B1 (https=) | 1974-12-06 |
| GB1328169A (en) | 1973-08-30 |
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