DE1292141B - Trisubstituierte Acrylsaeuren, deren Alkalisalze und ein Verfahren zu deren Herstellung - Google Patents
Trisubstituierte Acrylsaeuren, deren Alkalisalze und ein Verfahren zu deren HerstellungInfo
- Publication number
- DE1292141B DE1292141B DEG46251A DEG0046251A DE1292141B DE 1292141 B DE1292141 B DE 1292141B DE G46251 A DEG46251 A DE G46251A DE G0046251 A DEG0046251 A DE G0046251A DE 1292141 B DE1292141 B DE 1292141B
- Authority
- DE
- Germany
- Prior art keywords
- group
- trisubstituted
- ethyl
- alkali salts
- 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.)
- Pending
Links
- 150000001253 acrylic acids Chemical class 0.000 title claims description 9
- 150000001447 alkali salts Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 239000002253 acid Substances 0.000 claims description 9
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 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 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropanol Chemical compound CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 10
- -1 hydroxy acid esters Chemical class 0.000 description 9
- 230000000694 effects Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000000731 choleretic agent Substances 0.000 description 4
- 230000001989 choleretic effect Effects 0.000 description 4
- 229930016911 cinnamic acid Natural products 0.000 description 4
- 235000013985 cinnamic acid Nutrition 0.000 description 4
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- LGCMKPRGGJRYGM-UHFFFAOYSA-N Osalmid Chemical compound C1=CC(O)=CC=C1NC(=O)C1=CC=CC=C1O LGCMKPRGGJRYGM-UHFFFAOYSA-N 0.000 description 3
- 210000000941 bile Anatomy 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- ORCSAOZKNHLRPF-UHFFFAOYSA-N 2,3-diethylpent-2-enoic acid Chemical compound CCC(CC)=C(CC)C(O)=O ORCSAOZKNHLRPF-UHFFFAOYSA-N 0.000 description 2
- UGUZFCMQAVJQRO-UHFFFAOYSA-N 2-ethyl-3-phenylbut-2-enoic acid Chemical compound CCC(C(O)=O)=C(C)C1=CC=CC=C1 UGUZFCMQAVJQRO-UHFFFAOYSA-N 0.000 description 2
- 208000008599 Biliary fistula Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 1
- 239000004381 Choline salt Substances 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 241000723347 Cinnamomum Species 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000010234 biliary secretion Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000019417 choline salt Nutrition 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000001096 cystic duct Anatomy 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 231100000926 not very toxic Toxicity 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/42—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gastroenterology & Hepatology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Medicinal Preparation (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEG46251A DE1292141B (de) | 1966-03-08 | 1966-03-08 | Trisubstituierte Acrylsaeuren, deren Alkalisalze und ein Verfahren zu deren Herstellung |
| DEG46250A DE1292646B (de) | 1966-03-08 | 1966-03-08 | 2-Alkyl-3, 3-diphenylacrylsaeuren, deren Alkalisalze und ein Verfahren zu deren Herstellung |
| AT177767A AT271448B (de) | 1966-03-08 | 1967-02-23 | Verfahren zur Herstellung von neuen trisubstituierten Acrylsäuren und deren Salzen |
| ES337591A ES337591A1 (es) | 1966-03-08 | 1967-03-04 | Procedimiento de obtencion de acidos acrilicos transusti- tuidos y sus sales, de efecto coleretico. |
| ES337590A ES337590A1 (es) | 1966-03-08 | 1967-03-04 | Procedimiento de obtencion de 2-alquilo-3,3-difenilacrila- cido y sus sales, de efecto coleretico. |
| NL676703539A NL146783B (nl) | 1966-03-08 | 1967-03-06 | Werkwijze voor de bereiding van choleretisch werkzame verbindingen. |
| NL676703538A NL146484B (nl) | 1966-03-08 | 1967-03-06 | Werkwijze voor de bereiding van choleretisch werkzame verbindingen. |
| BE695050D BE695050A (enExample) | 1966-03-08 | 1967-03-06 | |
| BE695051D BE695051A (enExample) | 1966-03-08 | 1967-03-06 | |
| DK114967AA DK117559B (da) | 1966-03-08 | 1967-03-06 | Fremgangsmåde til fremstilling af køleretisk virkende 2-alkyl-3,3-diphenylakrylsyrer eller disses salte. |
| CH328967A CH472356A (de) | 1966-03-08 | 1967-03-07 | Verfahren zur Herstellung von 2-Alkyl-3,3-diphenylacrylsäuren |
| FR48366A FR1536211A (fr) | 1966-03-08 | 1967-03-07 | Procédé de préparation d'acides 2-alcoyl-3, 3-diphényl-acryliques et leurs sels |
| DK116767AA DK117485B (da) | 1966-03-08 | 1967-03-07 | Fremgangsmåde til fremstilling af koleretisk virkende trisubstituerede akrylsyrer og deres salte. |
| FR48366A FR1536212A (fr) | 1966-03-08 | 1967-03-07 | Procédé de préparation d'acides acryliques trisubstitués et leurs sels |
| CH329067A CH477390A (de) | 1966-03-08 | 1967-03-07 | Verfahren zur Herstellung von trisubstituierter Acrylsäure |
| GB10755/67A GB1139993A (en) | 1966-03-08 | 1967-03-07 | Novel acrylic acid derivatives and process for the preparation thereof |
| JP42014661A JPS4917254B1 (enExample) | 1966-03-08 | 1967-03-08 | |
| JP42014660A JPS5017468B1 (enExample) | 1966-03-08 | 1967-03-08 | |
| SE3171/67A SE315879B (enExample) | 1966-03-08 | 1967-03-08 | |
| SE3172/67A SE315880B (enExample) | 1966-03-08 | 1967-03-08 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEG46250A DE1292646B (de) | 1966-03-08 | 1966-03-08 | 2-Alkyl-3, 3-diphenylacrylsaeuren, deren Alkalisalze und ein Verfahren zu deren Herstellung |
| DEG46251A DE1292141B (de) | 1966-03-08 | 1966-03-08 | Trisubstituierte Acrylsaeuren, deren Alkalisalze und ein Verfahren zu deren Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1292141B true DE1292141B (de) | 1969-04-10 |
Family
ID=25978778
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG46251A Pending DE1292141B (de) | 1966-03-08 | 1966-03-08 | Trisubstituierte Acrylsaeuren, deren Alkalisalze und ein Verfahren zu deren Herstellung |
| DEG46250A Pending DE1292646B (de) | 1966-03-08 | 1966-03-08 | 2-Alkyl-3, 3-diphenylacrylsaeuren, deren Alkalisalze und ein Verfahren zu deren Herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG46250A Pending DE1292646B (de) | 1966-03-08 | 1966-03-08 | 2-Alkyl-3, 3-diphenylacrylsaeuren, deren Alkalisalze und ein Verfahren zu deren Herstellung |
Country Status (10)
| Country | Link |
|---|---|
| JP (2) | JPS4917254B1 (enExample) |
| BE (2) | BE695051A (enExample) |
| CH (2) | CH472356A (enExample) |
| DE (2) | DE1292141B (enExample) |
| DK (2) | DK117559B (enExample) |
| ES (2) | ES337591A1 (enExample) |
| FR (2) | FR1536212A (enExample) |
| GB (1) | GB1139993A (enExample) |
| NL (2) | NL146484B (enExample) |
| SE (2) | SE315879B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50118964U (enExample) * | 1974-03-09 | 1975-09-29 | ||
| JPS51103966U (enExample) * | 1975-02-19 | 1976-08-20 | ||
| JPS5220863U (enExample) * | 1975-08-01 | 1977-02-15 | ||
| JPS54163400U (enExample) * | 1978-05-08 | 1979-11-15 | ||
| JPS58225039A (ja) * | 1982-06-22 | 1983-12-27 | Eisai Co Ltd | ポリプレニル系化合物 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1136705B (de) * | 1959-02-20 | 1962-09-20 | Wallace & Tiernan Inc | Verfahren zur Herstellung von 2-(4'-Acetylpiperazino)-5-nitrothiazol |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1136703B (de) * | 1958-11-25 | 1962-09-20 | Zambon & C S P A G | Verfahren zur Herstellung von choleretisch wirksamen Phenyl-aethylcarbinol-carbonsaeureestern |
-
1966
- 1966-03-08 DE DEG46251A patent/DE1292141B/de active Pending
- 1966-03-08 DE DEG46250A patent/DE1292646B/de active Pending
-
1967
- 1967-03-04 ES ES337591A patent/ES337591A1/es not_active Expired
- 1967-03-04 ES ES337590A patent/ES337590A1/es not_active Expired
- 1967-03-06 BE BE695051D patent/BE695051A/xx unknown
- 1967-03-06 NL NL676703538A patent/NL146484B/xx unknown
- 1967-03-06 BE BE695050D patent/BE695050A/xx unknown
- 1967-03-06 NL NL676703539A patent/NL146783B/xx unknown
- 1967-03-06 DK DK114967AA patent/DK117559B/da unknown
- 1967-03-07 DK DK116767AA patent/DK117485B/da unknown
- 1967-03-07 FR FR48366A patent/FR1536212A/fr not_active Expired
- 1967-03-07 CH CH328967A patent/CH472356A/de not_active IP Right Cessation
- 1967-03-07 CH CH329067A patent/CH477390A/de not_active IP Right Cessation
- 1967-03-07 GB GB10755/67A patent/GB1139993A/en not_active Expired
- 1967-03-07 FR FR48366A patent/FR1536211A/fr not_active Expired
- 1967-03-08 SE SE3171/67A patent/SE315879B/xx unknown
- 1967-03-08 JP JP42014661A patent/JPS4917254B1/ja active Pending
- 1967-03-08 SE SE3172/67A patent/SE315880B/xx unknown
- 1967-03-08 JP JP42014660A patent/JPS5017468B1/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1136705B (de) * | 1959-02-20 | 1962-09-20 | Wallace & Tiernan Inc | Verfahren zur Herstellung von 2-(4'-Acetylpiperazino)-5-nitrothiazol |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1292646B (de) | 1969-04-17 |
| CH472356A (de) | 1969-05-15 |
| BE695051A (enExample) | 1967-08-14 |
| NL6703538A (enExample) | 1967-09-11 |
| ES337590A1 (es) | 1968-03-01 |
| NL146484B (nl) | 1975-07-15 |
| SE315880B (enExample) | 1969-10-13 |
| GB1139993A (en) | 1969-01-15 |
| JPS4917254B1 (enExample) | 1974-04-27 |
| BE695050A (enExample) | 1967-08-14 |
| SE315879B (enExample) | 1969-10-13 |
| NL146783B (nl) | 1975-08-15 |
| DK117485B (da) | 1970-05-04 |
| NL6703539A (enExample) | 1967-09-11 |
| JPS5017468B1 (enExample) | 1975-06-20 |
| DK117559B (da) | 1970-05-11 |
| FR1536212A (fr) | 1968-08-16 |
| CH477390A (de) | 1969-08-31 |
| ES337591A1 (es) | 1968-03-01 |
| FR1536211A (fr) | 1968-08-16 |
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