DE1957750C - - Google Patents
Info
- Publication number
- DE1957750C DE1957750C DE19691957750 DE1957750A DE1957750C DE 1957750 C DE1957750 C DE 1957750C DE 19691957750 DE19691957750 DE 19691957750 DE 1957750 A DE1957750 A DE 1957750A DE 1957750 C DE1957750 C DE 1957750C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- water
- hydroxycrotonic
- solution
- salt
- 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
- 239000004480 active ingredient Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- RTWLEDIMOQVWDF-IHWYPQMZSA-N (z)-2-hydroxybut-2-enoic acid Chemical class C\C=C(/O)C(O)=O RTWLEDIMOQVWDF-IHWYPQMZSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 8
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 8
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 8
- 229920002261 Corn starch Polymers 0.000 description 7
- 239000008120 corn starch Substances 0.000 description 7
- 235000019359 magnesium stearate Nutrition 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 239000008298 dragée Substances 0.000 description 6
- 229910002012 Aerosil® Inorganic materials 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000829 suppository Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- DKSZLDSPXIWGFO-BLOJGBSASA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;phosphoric acid;hydrate Chemical compound O.OP(O)(O)=O.OP(O)(O)=O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC DKSZLDSPXIWGFO-BLOJGBSASA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000000954 anitussive effect Effects 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229960004415 codeine phosphate Drugs 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- -1 biphenyl diazonium tetrafluoroborate Chemical compound 0.000 description 3
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 3
- 150000003946 cyclohexylamines Chemical class 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229960001462 sodium cyclamate Drugs 0.000 description 3
- TYLDGEVEWDNUTE-ZHACJKMWSA-N (e)-4-hydroxy-4-(4-phenylphenyl)but-2-enoic acid Chemical compound C1=CC(C(\C=C\C(O)=O)O)=CC=C1C1=CC=CC=C1 TYLDGEVEWDNUTE-ZHACJKMWSA-N 0.000 description 2
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 2
- 229910000761 Aluminium amalgam Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 235000013871 bee wax Nutrition 0.000 description 2
- 239000012166 beeswax Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 150000004074 biphenyls Chemical class 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 2
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 150000002780 morpholines Chemical class 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KLECYOQFQXJYBC-UHFFFAOYSA-N 1-fluoro-2-phenylbenzene Chemical group FC1=CC=CC=C1C1=CC=CC=C1 KLECYOQFQXJYBC-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- UMPNMJHTRNHHAL-UHFFFAOYSA-N 2-benzoyl-3-phenylprop-2-enoic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(=O)O)=CC1=CC=CC=C1 UMPNMJHTRNHHAL-UHFFFAOYSA-N 0.000 description 1
- CYPQRTFAWYCOQE-UHFFFAOYSA-N 4-[4-(2-fluorophenyl)phenyl]-4-oxobut-2-enoic acid Chemical compound C1=CC(C(=O)C=CC(=O)O)=CC=C1C1=CC=CC=C1F CYPQRTFAWYCOQE-UHFFFAOYSA-N 0.000 description 1
- KFQGOLUWWNZVAS-UHFFFAOYSA-N 4-oxo-4-(4-phenylphenyl)but-2-enoic acid Chemical compound C1=CC(C(=O)C=CC(=O)O)=CC=C1C1=CC=CC=C1 KFQGOLUWWNZVAS-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 238000003612 Meerwein-Ponndorf-Verley reduction reaction Methods 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 240000008790 Musa x paradisiaca Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000002322 anti-exudative effect Effects 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical class N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- MRVZZQOTPSZIJV-UHFFFAOYSA-N cyclohexanamine Chemical compound NC1CCCCC1.NC1CCCCC1 MRVZZQOTPSZIJV-UHFFFAOYSA-N 0.000 description 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
- 230000001151 other effect Effects 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
- 238000002360 preparation method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
Priority Applications (22)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE759053D BE759053A (fr) | 1969-11-17 | Nouveaux acides hydroxycrotoniques et procedes pour les fabriquer | |
| DE19691957750 DE1957750A1 (de) | 1969-11-17 | 1969-11-17 | Neue Hydroxycrotonsaeuren |
| FI702874A FI52334C (fi) | 1969-11-17 | 1970-10-26 | Menetelmä uusien tulehduksen vastaisten hydroksikrotomihappojen valmis tamiseksi. |
| BG16005A BG20561A3 (enrdf_load_stackoverflow) | 1969-11-17 | 1970-11-09 | |
| DK570770AA DK126644B (da) | 1969-11-17 | 1970-11-10 | Analogifremgangsmåde til fremstilling af racemiske eller optisk aktive hydroxycrotonsyrer eller salte deraf med uorganiske eller organiske baser. |
| CH1678070A CH537895A (de) | 1969-11-17 | 1970-11-12 | Verfahren zur Herstellung neuer Hydroxycrotonsäuren |
| US88983A US3655743A (en) | 1969-11-17 | 1970-11-12 | Substituted 4 - biphenyl-4-hydroxy crotonic acids and salts thereof |
| SU1490935A SU474134A3 (ru) | 1969-11-17 | 1970-11-13 | Способ получени замещенных оксикротоновых кислот |
| ES385588A ES385588A1 (es) | 1969-11-17 | 1970-11-16 | Procedimiento para la preparacion de nuevos acidos hidroxi-crotonicos. |
| SE15497/70A SE360649B (enrdf_load_stackoverflow) | 1969-11-17 | 1970-11-16 | |
| GB5447470A GB1322370A (en) | 1969-11-17 | 1970-11-16 | Hydroxycrotonic acid derivatives their preparation and compositions containing them and intermediates for the preparation of the same |
| NL7016745A NL7016745A (enrdf_load_stackoverflow) | 1969-11-17 | 1970-11-16 | |
| JP45100955A JPS4948311B1 (enrdf_load_stackoverflow) | 1969-11-17 | 1970-11-16 | |
| PL14445570A PL81263B1 (enrdf_load_stackoverflow) | 1969-11-17 | 1970-11-16 | |
| RO6498770A RO61973A (fr) | 1969-11-17 | 1970-11-16 | Procede pour la prapartion des acides hydroxycrotoniques |
| CS7726A CS178073B2 (enrdf_load_stackoverflow) | 1969-11-17 | 1970-11-16 | |
| IL35656A IL35656A (en) | 1969-11-17 | 1970-11-16 | Substituted hydroxycrotonic acids and their salts,their preparation and pharmaceutical compositions containing them |
| NO4359/70A NO134462C (enrdf_load_stackoverflow) | 1969-11-17 | 1970-11-16 | |
| IE1481/70A IE34744B1 (en) | 1969-11-17 | 1970-11-17 | Novel hydroxycrotonic acid derivatives,their preparation and compositions containing them and novel intermediates for the preparation of the same |
| FR7041115A FR2073368B1 (enrdf_load_stackoverflow) | 1969-11-17 | 1970-11-17 | |
| AT1036770A AT303018B (de) | 1969-11-17 | 1970-11-17 | Verfahren zur Herstellung von neuen Hydroxycrotonsäuren |
| CA098,303A CA984408A (en) | 1969-11-17 | 1970-11-17 | Hydroxycrotonic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691957750 DE1957750A1 (de) | 1969-11-17 | 1969-11-17 | Neue Hydroxycrotonsaeuren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1957750A1 DE1957750A1 (de) | 1971-06-03 |
| DE1957750C true DE1957750C (enrdf_load_stackoverflow) | 1973-05-24 |
Family
ID=5751347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691957750 Granted DE1957750A1 (de) | 1969-11-17 | 1969-11-17 | Neue Hydroxycrotonsaeuren |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1957750A1 (enrdf_load_stackoverflow) |
| PL (1) | PL81263B1 (enrdf_load_stackoverflow) |
-
1969
- 1969-11-17 DE DE19691957750 patent/DE1957750A1/de active Granted
-
1970
- 1970-11-16 PL PL14445570A patent/PL81263B1/pl unknown
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