CH619437A5 - Process for the preparation of polyene compounds. - Google Patents
Process for the preparation of polyene compounds. Download PDFInfo
- Publication number
- CH619437A5 CH619437A5 CH1090775A CH1090775A CH619437A5 CH 619437 A5 CH619437 A5 CH 619437A5 CH 1090775 A CH1090775 A CH 1090775A CH 1090775 A CH1090775 A CH 1090775A CH 619437 A5 CH619437 A5 CH 619437A5
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- reaction
- organic phase
- vitamin
- acetate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 29
- -1 polyene compounds Chemical class 0.000 title claims description 27
- 238000002360 preparation method Methods 0.000 title claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 16
- QGNJRVVDBSJHIZ-QHLGVNSISA-N retinyl acetate Chemical compound CC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C QGNJRVVDBSJHIZ-QHLGVNSISA-N 0.000 claims description 16
- 235000019173 retinyl acetate Nutrition 0.000 claims description 14
- 239000011770 retinyl acetate Substances 0.000 claims description 14
- 239000012074 organic phase Substances 0.000 claims description 13
- 229960000342 retinol acetate Drugs 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000012071 phase Substances 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 17
- 239000000203 mixture Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 3
- 150000004714 phosphonium salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QGNJRVVDBSJHIZ-AQDFTDIISA-N (2e,4e,6z,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl acetate Chemical compound CC(=O)OC\C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C QGNJRVVDBSJHIZ-AQDFTDIISA-N 0.000 description 2
- FPIPGXGPPPQFEQ-HWCYFHEPSA-N 13-cis-retinol Chemical compound OC/C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-HWCYFHEPSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- BMCARTGCDBZHOV-UHFFFAOYSA-N (3-methyl-6-oxohexa-2,4-dienyl) acetate Chemical compound CC(=O)OCC=C(C)C=CC=O BMCARTGCDBZHOV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000002905 alkanoylamido group Chemical group 0.000 description 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 150000004347 all-trans-retinol derivatives Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- YLFXEUMFBVGYEL-UHFFFAOYSA-N ethyl 3-methyl-4-oxobut-2-enoate Chemical compound CCOC(=O)C=C(C)C=O YLFXEUMFBVGYEL-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229930002330 retinoic acid Natural products 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
- C07C403/12—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1090775A CH619437A5 (en) | 1975-08-22 | 1975-08-22 | Process for the preparation of polyene compounds. |
| IT25963/76A IT1064741B (it) | 1975-08-22 | 1976-08-03 | Procedimento per la preparazione di composti polienici |
| US05/711,765 US4081470A (en) | 1975-08-22 | 1976-08-04 | Manufacture of polyene compounds via a Wittig reaction in a two phase solvent system |
| NLAANVRAGE7608973,A NL189560C (nl) | 1975-08-22 | 1976-08-12 | Werkwijze voor het bereiden van een polyeenverbinding die een 3,7-dimethyl-nona-1,3,5,7 tetraeen-1-yl-rest bevat. |
| DE2636879A DE2636879C2 (de) | 1975-08-22 | 1976-08-17 | Verfahren zur Herstellung von den 3,7-Dimethyl-nona-1,3,5,7-tetraen-1-yl-rest enthaltenden Polyenverbindungen |
| JP51098844A JPS6051457B2 (ja) | 1975-08-22 | 1976-08-20 | ポリエン化合物の製造方法 |
| FR7625321A FR2321467A1 (fr) | 1975-08-22 | 1976-08-20 | Procede pour la preparation d'un compose polyenique contenant un groupement 3,7-dimethyl-nona-1,3,5,7-tetraen-1-yle |
| AT621376A AT351682B (de) | 1975-08-22 | 1976-08-20 | Verfahren zur herstellung von polyenver- bindungen |
| GB34791/76A GB1550173A (en) | 1975-08-22 | 1976-08-20 | Process for the manufacture of polyene compounds |
| BE169947A BE845366A (fr) | 1975-08-22 | 1976-08-20 | Procede pour la preparation d'un compose polyenique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1090775A CH619437A5 (en) | 1975-08-22 | 1975-08-22 | Process for the preparation of polyene compounds. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH619437A5 true CH619437A5 (en) | 1980-09-30 |
Family
ID=4368076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1090775A CH619437A5 (en) | 1975-08-22 | 1975-08-22 | Process for the preparation of polyene compounds. |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS6051457B2 (enExample) |
| AT (1) | AT351682B (enExample) |
| BE (1) | BE845366A (enExample) |
| CH (1) | CH619437A5 (enExample) |
| DE (1) | DE2636879C2 (enExample) |
| FR (1) | FR2321467A1 (enExample) |
| GB (1) | GB1550173A (enExample) |
| IT (1) | IT1064741B (enExample) |
| NL (1) | NL189560C (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3434038A1 (de) * | 1984-09-17 | 1986-03-27 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von alkali- und erdalkalisalzen der benzaldehyd-2,4-disulfonsaeure |
| FR2872129B1 (fr) | 2004-06-23 | 2008-12-12 | Solystic Sa | Bac de stockage pour lettres et objets plats postaux |
| DE102008002302A1 (de) | 2007-06-13 | 2008-12-18 | Basf Se | Verfahren zur Hestellung von Etretinat |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1068709B (de) * | 1959-11-12 | Badische Anilin- S. Soda-Faibrik Aktiengesellschaft, Ludwigshafen/Rhein | Verfahren zur Synthese von Verbindungen der Axerophtyliden-Reihe | |
| DE1068710B (de) * | 1958-08-06 | 1959-11-12 | Badische Anilin- &. Soda-Fabrik Aktiengesellschaft, Ludwigshafen/Rhein | Verfahren zur Herstellung von Verbindungen der beta-Ionylidenäthyliden-Reihe |
| CH388300A (de) * | 1958-03-14 | 1965-02-28 | Basf Ag | Verfahren zur Herstellung von den B-Cyclogeranylidenrest tragenden Verbindungen |
| DE1259890B (de) * | 1965-12-21 | 1968-02-01 | Basf Ag | Verfahren zur Herstellung von Carbonsaeurenitrilen |
| CH585166A5 (enExample) * | 1973-03-30 | 1977-02-28 | Hoffmann La Roche |
-
1975
- 1975-08-22 CH CH1090775A patent/CH619437A5/de not_active IP Right Cessation
-
1976
- 1976-08-03 IT IT25963/76A patent/IT1064741B/it active
- 1976-08-12 NL NLAANVRAGE7608973,A patent/NL189560C/xx not_active IP Right Cessation
- 1976-08-17 DE DE2636879A patent/DE2636879C2/de not_active Expired
- 1976-08-20 BE BE169947A patent/BE845366A/xx not_active IP Right Cessation
- 1976-08-20 AT AT621376A patent/AT351682B/de not_active IP Right Cessation
- 1976-08-20 FR FR7625321A patent/FR2321467A1/fr active Granted
- 1976-08-20 GB GB34791/76A patent/GB1550173A/en not_active Expired
- 1976-08-20 JP JP51098844A patent/JPS6051457B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6051457B2 (ja) | 1985-11-14 |
| AT351682B (de) | 1979-08-10 |
| FR2321467A1 (fr) | 1977-03-18 |
| JPS5225732A (en) | 1977-02-25 |
| IT1064741B (it) | 1985-02-25 |
| GB1550173A (en) | 1979-08-08 |
| FR2321467B1 (enExample) | 1982-04-09 |
| NL189560B (nl) | 1992-12-16 |
| NL189560C (nl) | 1993-05-17 |
| NL7608973A (nl) | 1977-02-24 |
| ATA621376A (de) | 1979-01-15 |
| DE2636879A1 (de) | 1977-03-03 |
| DE2636879C2 (de) | 1985-11-28 |
| BE845366A (fr) | 1977-02-21 |
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| Date | Code | Title | Description |
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| PUE | Assignment |
Owner name: F. HOFFMANN-LA ROCHE AG |
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| PL | Patent ceased |