DE1176144B - Verfahren zur Herstellung von Estern des 3-Phenyl-3-hydroxypyrrolidins und deren Salzen - Google Patents
Verfahren zur Herstellung von Estern des 3-Phenyl-3-hydroxypyrrolidins und deren SalzenInfo
- Publication number
- DE1176144B DE1176144B DEP22513A DEP0022513A DE1176144B DE 1176144 B DE1176144 B DE 1176144B DE P22513 A DEP22513 A DE P22513A DE P0022513 A DEP0022513 A DE P0022513A DE 1176144 B DE1176144 B DE 1176144B
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- ether
- hydroxypyrrolidine
- salts
- lower alkyl
- 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 11
- 238000000034 method Methods 0.000 title claims description 10
- AFQYBBFSDHKQJV-UHFFFAOYSA-N 3-phenylpyrrolidin-3-ol Chemical compound C=1C=CC=CC=1C1(O)CCNC1 AFQYBBFSDHKQJV-UHFFFAOYSA-N 0.000 title claims description 6
- 150000002148 esters Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- -1 carboxylic acid derivatives Halides Chemical class 0.000 claims description 4
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- FCLZCOCSZQNREK-UHFFFAOYSA-N Pyrrolidine, hydrochloride Chemical compound Cl.C1CCNC1 FCLZCOCSZQNREK-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 241000700159 Rattus Species 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 230000000202 analgesic effect Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XJHIXSGLTIAYLD-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;pyrrolidine Chemical compound C1CCNC1.OC(=O)C(O)C(O)C(O)=O XJHIXSGLTIAYLD-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- QGKLPGKXAVVPOJ-UHFFFAOYSA-N pyrrolidin-3-one Chemical compound O=C1CCNC1 QGKLPGKXAVVPOJ-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- ZYPZDVCEBCVJGX-UHFFFAOYSA-N (1,4-dimethyl-3-phenylpyrrolidin-3-yl) propanoate Chemical compound C=1C=CC=CC=1C1(OC(=O)CC)CN(C)CC1C ZYPZDVCEBCVJGX-UHFFFAOYSA-N 0.000 description 1
- ZBIWFRIPOVNKHR-UHFFFAOYSA-N (1,5-dimethyl-3-phenylpyrrolidin-3-yl) propanoate Chemical compound C=1C=CC=CC=1C1(OC(=O)CC)CC(C)N(C)C1 ZBIWFRIPOVNKHR-UHFFFAOYSA-N 0.000 description 1
- BLRDJWDKGIIOSB-UHFFFAOYSA-N (2-methyl-3-phenylpyrrolidin-3-yl) propanoate Chemical compound C=1C=CC=CC=1C1(OC(=O)CC)CCNC1C BLRDJWDKGIIOSB-UHFFFAOYSA-N 0.000 description 1
- BAYDLDJKTJEXLI-UHFFFAOYSA-N 1,2,4-trimethyl-3-phenylpyrrolidin-3-ol Chemical compound CN1C(C(C(C1)C)(O)C1=CC=CC=C1)C BAYDLDJKTJEXLI-UHFFFAOYSA-N 0.000 description 1
- OTRFAQOSMBFREC-UHFFFAOYSA-N 1,2-dimethyl-3-phenylpyrrolidin-3-ol Chemical compound CC1N(C)CCC1(O)C1=CC=CC=C1 OTRFAQOSMBFREC-UHFFFAOYSA-N 0.000 description 1
- XDFQFXXJLSXTQA-UHFFFAOYSA-N 1,4-dimethyl-3-phenylpyrrolidin-3-ol Chemical compound CC1CN(C)CC1(O)C1=CC=CC=C1 XDFQFXXJLSXTQA-UHFFFAOYSA-N 0.000 description 1
- UQQSVHQSPTWCGS-UHFFFAOYSA-N 1,5-dimethyl-3-phenylpyrrolidin-3-ol Chemical compound C1N(C)C(C)CC1(O)C1=CC=CC=C1 UQQSVHQSPTWCGS-UHFFFAOYSA-N 0.000 description 1
- KHKJEZHCAXTVGB-UHFFFAOYSA-N 1-methyl-3-phenylpyrrolidin-3-ol Chemical compound C1N(C)CCC1(O)C1=CC=CC=C1 KHKJEZHCAXTVGB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- QAWBXZYPFCFQLA-UHFFFAOYSA-N butanoyl bromide Chemical compound CCCC(Br)=O QAWBXZYPFCFQLA-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- LUKSBMJXPCFBKO-UHFFFAOYSA-N prodilidine Chemical compound C=1C=CC=CC=1C1(OC(=O)CC)CCN(C)C1C LUKSBMJXPCFBKO-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB10617/58A GB862513A (en) | 1958-04-02 | 1958-04-02 | Pyrrolidine compounds and methods for producing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1176144B true DE1176144B (de) | 1964-08-20 |
Family
ID=9971170
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP22513A Pending DE1176144B (de) | 1958-04-02 | 1959-04-01 | Verfahren zur Herstellung von Estern des 3-Phenyl-3-hydroxypyrrolidins und deren Salzen |
| DEP26856A Pending DE1241829B (de) | 1958-04-02 | 1959-04-01 | Verfahren zur Herstellung von Estern des 3-Phenyl-3-hydroxypyrrolidins und ihren Salzen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP26856A Pending DE1241829B (de) | 1958-04-02 | 1959-04-01 | Verfahren zur Herstellung von Estern des 3-Phenyl-3-hydroxypyrrolidins und ihren Salzen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3256297A (en, 2012) |
| CH (1) | CH392508A (en, 2012) |
| DE (2) | DE1176144B (en, 2012) |
| ES (1) | ES247911A1 (en, 2012) |
| FR (2) | FR1374302A (en, 2012) |
| GB (1) | GB862513A (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3185702A (en) * | 1959-03-16 | 1965-05-25 | Lunsford Carl Dalton | Basic esters of 3-aryl-3-pyrrolidinols |
| US3462452A (en) * | 1966-05-17 | 1969-08-19 | Parke Davis & Co | 1-phenethyl or p-aminophenethyl-3-(m-hydroxy- or alkanoyloxy-phenyl)-3-propylpyrrolidines and salts thereof |
| US4774340A (en) * | 1984-04-06 | 1988-09-27 | Miles Inc. | Method for preparing 3-hydroxy pyrroles and esters thereof |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2878264A (en) * | 1959-03-17 | Substituted amino alcohols | ||
| US2880211A (en) * | 1959-03-31 | Chcoochj | ||
| US2850500A (en) * | 1958-09-02 | Chjchzcoochj | ||
| US2824875A (en) * | 1958-02-25 | Certificate of correction | ||
| GB483258A (en) * | 1936-06-08 | 1938-04-14 | Arthur George Bloxam | Manufacture of basic esters of polyarylacetic acids |
| GB629196A (en) * | 1946-07-08 | 1949-09-14 | Roche Products Ltd | Piperidine derivatives |
| NL94071C (en, 2012) * | 1954-04-20 | |||
| US2765314A (en) * | 1954-05-12 | 1956-10-02 | Rohm & Haas | Preparation of esters |
| US2784192A (en) * | 1954-06-24 | 1957-03-05 | Rohm & Haas | Preparation of 4-hydroxypiperidines |
| US2846437A (en) * | 1955-09-12 | 1958-08-05 | Sterling Drug Inc | Lower alkyl 4-phenyl-1-(substituted-alkyl) piperidine-4-carboxylates and preparationthereof |
-
1958
- 1958-04-02 GB GB10617/58A patent/GB862513A/en not_active Expired
-
1959
- 1959-03-14 ES ES0247911A patent/ES247911A1/es not_active Expired
- 1959-03-20 US US800643A patent/US3256297A/en not_active Expired - Lifetime
- 1959-03-31 CH CH7139059A patent/CH392508A/fr unknown
- 1959-03-31 FR FR790838A patent/FR1374302A/fr not_active Expired
- 1959-04-01 DE DEP22513A patent/DE1176144B/de active Pending
- 1959-04-01 DE DEP26856A patent/DE1241829B/de active Pending
-
1960
- 1960-08-31 FR FR837391A patent/FR594M/fr active Active
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB862513A (en) | 1961-03-08 |
| FR594M (en, 2012) | 1961-06-12 |
| US3256297A (en) | 1966-06-14 |
| FR1374302A (fr) | 1964-10-09 |
| CH392508A (fr) | 1965-05-31 |
| ES247911A1 (es) | 1959-08-16 |
| DE1241829B (de) | 1967-06-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2414680C2 (de) | Substituierte 2-Furancarbonsäuren und 2-Furancarbonsäureester, Verfahren zu ihrer Herstellung und Arzneimittel, die diese Verbindungen enthalten | |
| DE2265138B2 (de) | Vincaminsäure-benzylester, dessen Salze mit Säuren, ein Verfahren zu ihrer Herstellung und pharmazeutische Mittel | |
| DE1176144B (de) | Verfahren zur Herstellung von Estern des 3-Phenyl-3-hydroxypyrrolidins und deren Salzen | |
| DE2829471C2 (en, 2012) | ||
| DE1695752A1 (de) | Verfahren zur Herstellung von Derivaten des 1,6-Dimethyl-10alpha-ergolins | |
| DE2123111A1 (de) | Penicillansäure-Derivate | |
| DE1470123B2 (de) | 4-(2,6-Dioxo-3-phenyl-3-piperidyl)piperidine, deren pharmakologisch verträgliche Säureadditionssalze und Verfahren zu ihrer Herstellung | |
| DE3414801A1 (de) | 4-(nitrophenyl)-tetrahydropyridine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel | |
| DE1294968B (de) | Phloroglucinverbindungen und Verfahren zu ihrer Herstellung | |
| DD150060A5 (de) | Verfahren zur herstellung von neuen phenthiazin-derivaten | |
| DE2418805C3 (de) | 16β -Carboxy-11,17α -dimethoxy-18β -benzoyloxy-yohimbanderivate und Verfahren zu deren Herstellung | |
| DE2338350A1 (de) | Beta-(3,4-dialkanoyloxyphenyl)-lalanin-ester | |
| DE1470013A1 (de) | Verfahren zur Herstellung von Tetracyclin-Derivaten | |
| CH627169A5 (en, 2012) | ||
| DE716579C (de) | Verfahren zur Herstellung von Esteramiden der Mandelsaeure | |
| DE959015C (de) | Verfahren zur Herstellung von neuen pharmakologisch wirksamen basischen Estern und ihren Salzen | |
| DE1812937C3 (de) | 4-(Ammoäthansulfonylamino)-antipyrine und Aminoäthansulfonyl-p-phenetidine sowie Verfahren zu ihrer Herstellung | |
| DE1795713C3 (de) | a-Aminobenzylpenicillinsäureester | |
| DE1620436C (de) | Carboxamidoalkyl 1,3 benzoxazin 2 on derivate und Verfahren zu deren Her stellung | |
| AT242868B (de) | Verfahren zur Herstellung neuer 18-Azido-18-desoxy-reserpsäureester und deren Salzen | |
| DE1793690C3 (de) | 1 S-Hydroxy-9-oxoprosta-5-cis-10,13trans-triensäure und deren Salze sowie Verfahren zu ihrer Herstellung | |
| DE1545764C (de) | p Chlorphenvhsopropylcarbinol nico tinsaureester | |
| AT319463B (de) | Röntgenkontrastmittel | |
| DE2432322A1 (de) | Neues pyridinderivat und seine additionssalze, herstellungsverfahren dafuer sowie pharmazeutische zusammensetzungen | |
| DE2159679C3 (de) | Isonipecotinsäurederivate |