DE626539C - Verfahren zur Darstellung von basischen Estern der Polyphenylessigsaeuren - Google Patents
Verfahren zur Darstellung von basischen Estern der PolyphenylessigsaeurenInfo
- Publication number
- DE626539C DE626539C DEG89225D DEG0089225D DE626539C DE 626539 C DE626539 C DE 626539C DE G89225 D DEG89225 D DE G89225D DE G0089225 D DEG0089225 D DE G0089225D DE 626539 C DE626539 C DE 626539C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- parts
- ester
- acids
- esters
- 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
- 150000002148 esters Chemical class 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 4
- 235000011054 acetic acid Nutrition 0.000 title 1
- 150000001243 acetic acids Chemical class 0.000 title 1
- 229920006389 polyphenyl polymer Polymers 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 15
- 150000007513 acids Chemical class 0.000 claims description 10
- -1 Benzilic acid ester Chemical class 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- MSYLETHDEIJMAF-UHFFFAOYSA-N 2,2-diphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(C(=O)Cl)C1=CC=CC=C1 MSYLETHDEIJMAF-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 2
- XGIKILRODBEJIL-UHFFFAOYSA-N 1-(ethylamino)ethanol Chemical compound CCNC(C)O XGIKILRODBEJIL-UHFFFAOYSA-N 0.000 description 2
- VBSTXRUAXCTZBQ-UHFFFAOYSA-N 1-hexyl-4-phenylpiperazine Chemical compound C1CN(CCCCCC)CCN1C1=CC=CC=C1 VBSTXRUAXCTZBQ-UHFFFAOYSA-N 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- JACRWUWPXAESPB-QMMMGPOBSA-N Tropic acid Natural products OC[C@H](C(O)=O)C1=CC=CC=C1 JACRWUWPXAESPB-QMMMGPOBSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- NWCHELUCVWSRRS-UHFFFAOYSA-N atrolactic acid Chemical compound OC(=O)C(O)(C)C1=CC=CC=C1 NWCHELUCVWSRRS-UHFFFAOYSA-N 0.000 description 2
- 229940087675 benzilic acid Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229960002510 mandelic acid Drugs 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- GBBZLMLLFVFKJM-UHFFFAOYSA-N 1,2-diiodoethane Chemical compound ICCI GBBZLMLLFVFKJM-UHFFFAOYSA-N 0.000 description 1
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 1
- UOZBNMMELVBICG-UHFFFAOYSA-N 2,2,2-triphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)Cl)C1=CC=CC=C1 UOZBNMMELVBICG-UHFFFAOYSA-N 0.000 description 1
- HZLYGAQNCRJBDT-UHFFFAOYSA-N 2-(ethylamino)propan-2-ol Chemical compound CCNC(C)(C)O HZLYGAQNCRJBDT-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
- PYYBPWSWSPMKTL-UHFFFAOYSA-N 3-(dimethylamino)cyclohexan-1-ol Chemical compound CN(C)C1CCCC(O)C1 PYYBPWSWSPMKTL-UHFFFAOYSA-N 0.000 description 1
- NIQIPYGXPZUDDP-UHFFFAOYSA-N 3-aminocyclohexan-1-ol Chemical compound NC1CCCC(O)C1 NIQIPYGXPZUDDP-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- XLEOCTUCGZANAC-UHFFFAOYSA-N 4-(diethylamino)butan-2-one Chemical compound CCN(CC)CCC(C)=O XLEOCTUCGZANAC-UHFFFAOYSA-N 0.000 description 1
- 229930003347 Atropine Natural products 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229960000396 atropine Drugs 0.000 description 1
- UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- PYPHPZOQIVEWHN-UHFFFAOYSA-N ethyl 2,2-diphenylacetate Chemical group C=1C=CC=CC=1C(C(=O)OCC)C1=CC=CC=C1 PYPHPZOQIVEWHN-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QLNWXBAGRTUKKI-UHFFFAOYSA-N metacetamol Chemical compound CC(=O)NC1=CC=CC(O)=C1 QLNWXBAGRTUKKI-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2079962X | 1934-07-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE626539C true DE626539C (de) | 1936-02-27 |
Family
ID=31994866
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG89225D Expired DE626539C (de) | 1934-07-12 | 1934-11-24 | Verfahren zur Darstellung von basischen Estern der Polyphenylessigsaeuren |
| DEG92670D Expired DE653778C (de) | 1934-07-12 | 1936-04-12 | Verfahren zur Herstellung von basischen Estern der Diphenylessigsaeure |
| DEG95279D Expired DE680662C (de) | 1934-07-12 | 1937-04-22 | Verfahren zur Darstellung neuer basischer Ester der Diphenylessigsaeure |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG92670D Expired DE653778C (de) | 1934-07-12 | 1936-04-12 | Verfahren zur Herstellung von basischen Estern der Diphenylessigsaeure |
| DEG95279D Expired DE680662C (de) | 1934-07-12 | 1937-04-22 | Verfahren zur Darstellung neuer basischer Ester der Diphenylessigsaeure |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2079962A (enrdf_load_stackoverflow) |
| DE (3) | DE626539C (enrdf_load_stackoverflow) |
| FR (1) | FR795597A (enrdf_load_stackoverflow) |
| GB (1) | GB448181A (enrdf_load_stackoverflow) |
| NL (1) | NL42150C (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE763489C (de) * | 1937-11-09 | 1951-08-09 | Friedrich Dr Luther | Verfahren zur Herstellung von ª-Aminoaethylestern substituierter Phenylessigsaeuren |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2648666A (en) * | 1953-08-11 | Quaternary ammonium salts derived | ||
| US2447395A (en) * | 1940-07-05 | 1948-08-17 | Parke Davis & Co | Morpholine substituted esters |
| US2446522A (en) * | 1940-07-08 | 1948-08-10 | Winthrop Stearns Inc | Diaryl nitrogenous heterocyclic alkylene compounds |
| US2423025A (en) * | 1942-03-31 | 1947-06-24 | American Cyanamid Co | Alkamine esters of diarylpropionic acids |
| US2419366A (en) * | 1942-04-08 | 1947-04-22 | American Cyanamid Co | Alkanol esters |
| US2475852A (en) * | 1942-04-08 | 1949-07-12 | American Cyanamid Co | Morpholinoalkanol esters |
| US2421729A (en) * | 1943-05-20 | 1947-06-03 | Burroughs Wellcome Co | Production of 3-aryl-1, 5-dibrompentane-3-carboxylic acid |
| US2474651A (en) * | 1944-02-26 | 1949-06-28 | Univ Michigan | Basic-alkyl esters and their salts |
| US2415079A (en) * | 1944-02-26 | 1947-02-04 | Regents | Basic-alkyl esters and their salts |
| US2489950A (en) * | 1944-02-26 | 1949-11-29 | Univ Michigan | Basic-alkyl esters and their salts |
| US2533084A (en) * | 1946-08-17 | 1950-12-05 | Univ Michigan | Aminoalkyl esters of dithienyl aliphatic acids |
| US2607777A (en) * | 1947-04-10 | 1952-08-19 | Searle & Co | N-alkyl piperidyl alkyl esters of diphenyl acetic acid and 9-fluorenyl carboxylic acid |
| US2589937A (en) * | 1947-05-23 | 1952-03-18 | Geigy Ag J R | Manufacture of new basic esters of 1-aryl-cyclopentane-1-monothiocarboxylic acids |
| US2662891A (en) * | 1948-01-12 | 1953-12-15 | Schering Corp | P-chlorophenyl(2-pyridyl) (beta-dimethylaminoethoxy) methane |
| US2576230A (en) * | 1948-02-20 | 1951-11-27 | Searle & Co | Aminoalkyl esters of alpha, beta, beta-triarylpropionic acids |
| US2512307A (en) * | 1948-07-24 | 1950-06-20 | Sterling Drug Inc | Esters of di-substituted acetic acids and sulfur containing tertiary amino alkanols |
| US2659725A (en) * | 1950-06-21 | 1953-11-17 | Searle & Co | Quaternary ammonium salts of heterocyclylalkanol esters of xanthene-9-carboxylic acid |
| US2918407A (en) * | 1957-04-08 | 1959-12-22 | Lakeside Lab Inc | Anti-spasmodics specific for upper gastrointestinal pain and spasm |
| US2995492A (en) * | 1957-12-23 | 1961-08-08 | Lakeside Lab Inc | Piperidine derivatives with psychotogenic activity |
| US2995560A (en) * | 1959-09-11 | 1961-08-08 | Lakeside Lab Inc | Acetates of 3-piperidinol |
| US3014913A (en) * | 1959-11-16 | 1961-12-26 | Upjohn Co | Ortho-alkanoyloxy-benzoates of n-phenylethyl-4-piperidinol |
| DE1162846B (de) * | 1961-08-17 | 1964-02-13 | C. F. Boehringer & Soehne G.m. b.H., Mannheim-Waldhof | Verfahren zur Herstellung von Estern von N-(Hydroxyalkyl)-nortropanen bzw.-norgranatanen und ihren Salzen. |
| DE1163844B (de) * | 1960-11-26 | 1964-02-27 | C F Boehrm^er S. Soehne G m bH Mannheim Wildhof | Verfahren zur Herstellung von Estern von N-(Hydroxyalkyl)-nortropanen bzw. -norgranatanen und ihren Hydrohalogeniden. |
| DE1162845B (de) * | 1961-08-16 | 1964-02-13 | C. F. Boehringer &. Soehne G.m. b.H., Mannheim-Waldhof | Verfahren zur Herstellung der Hydrohalogenide von Estern von N-(Hydroxyalkyl)-nortropanen bzw.-norgranatanen. |
| US3174994A (en) * | 1962-01-30 | 1965-03-23 | Smith Kline French Lab | Hypocholesterolemic n-oxide compositions |
| DE3544172A1 (de) * | 1985-12-13 | 1987-06-19 | Lentia Gmbh | Neue kristalline salze von aryloxy-propanolaminen, verfahren zu ihrer herstellung und ihre verwendung |
| US4973734A (en) * | 1989-03-17 | 1990-11-27 | The United States Of America As Represented By The Secretary Of The Army | Carbaphens: aprophen analogs that are binary antidotes for organophosphate poisoning |
-
1934
- 1934-11-23 GB GB33727/34A patent/GB448181A/en not_active Expired
- 1934-11-24 DE DEG89225D patent/DE626539C/de not_active Expired
-
1935
- 1935-06-26 NL NL74027A patent/NL42150C/xx active
- 1935-07-06 US US30166A patent/US2079962A/en not_active Expired - Lifetime
- 1935-07-10 FR FR795597D patent/FR795597A/fr not_active Expired
-
1936
- 1936-04-12 DE DEG92670D patent/DE653778C/de not_active Expired
-
1937
- 1937-04-22 DE DEG95279D patent/DE680662C/de not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE763489C (de) * | 1937-11-09 | 1951-08-09 | Friedrich Dr Luther | Verfahren zur Herstellung von ª-Aminoaethylestern substituierter Phenylessigsaeuren |
Also Published As
| Publication number | Publication date |
|---|---|
| GB448181A (en) | 1936-05-25 |
| DE653778C (de) | 1937-12-02 |
| US2079962A (en) | 1937-05-11 |
| FR795597A (fr) | 1936-03-17 |
| DE680662C (de) | 1939-09-06 |
| NL42150C (enrdf_load_stackoverflow) | 1937-12-15 |
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