CH619437A5 - Process for the preparation of polyene compounds. - Google Patents

Process for the preparation of polyene compounds. Download PDF

Info

Publication number: CH619437A5
Authority: CH; Switzerland
Prior art keywords: water; reaction; organic phase; vitamin; acetate
Prior art date: 1975-08-22

Application number

CH1090775A

Other languages

German (de)

English (en)

Inventor

Kuno Dr Schleich

Hansjoerg Dr Stoller

Original Assignee

Hoffmann La Roche

Priority date (The priority date 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 date listed.)

1975-08-22

Filing date

1975-08-22

Publication date

1980-09-30

1975-08-22 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1975-08-22 Priority to CH1090775A priority Critical patent/CH619437A5/de

1976-08-03 Priority to IT25963/76A priority patent/IT1064741B/it

1976-08-04 Priority to US05/711,765 priority patent/US4081470A/en

1976-08-12 Priority to NLAANVRAGE7608973,A priority patent/NL189560C/xx

1976-08-17 Priority to DE2636879A priority patent/DE2636879C2/de

1976-08-20 Priority to JP51098844A priority patent/JPS6051457B2/ja

1976-08-20 Priority to GB34791/76A priority patent/GB1550173A/en

1976-08-20 Priority to AT621376A priority patent/AT351682B/de

1976-08-20 Priority to FR7625321A priority patent/FR2321467A1/fr

1976-08-20 Priority to BE169947A priority patent/BE845366A/fr

1980-09-30 Publication of CH619437A5 publication Critical patent/CH619437A5/de

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)

CH1090775A 1975-08-22 1975-08-22 Process for the preparation of polyene compounds. CH619437A5 (en)

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
GB34791/76A GB1550173A (en)	1975-08-22	1976-08-20	Process for the manufacture of polyene compounds
AT621376A AT351682B (de)	1975-08-22	1976-08-20	Verfahren zur herstellung von polyenver- bindungen
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
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 (fr)
AT (1)	AT351682B (fr)
BE (1)	BE845366A (fr)
CH (1)	CH619437A5 (fr)
DE (1)	DE2636879C2 (fr)
FR (1)	FR2321467A1 (fr)
GB (1)	GB1550173A (fr)
IT (1)	IT1064741B (fr)
NL (1)	NL189560C (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 (fr) *	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 FR FR7625321A patent/FR2321467A1/fr active Granted
- 1976-08-20 GB GB34791/76A patent/GB1550173A/en not_active Expired
- 1976-08-20 BE BE169947A patent/BE845366A/fr not_active IP Right Cessation
- 1976-08-20 AT AT621376A patent/AT351682B/de not_active IP Right Cessation
- 1976-08-20 JP JP51098844A patent/JPS6051457B2/ja not_active Expired

Also Published As

Publication number	Publication date
DE2636879A1 (de)	1977-03-03
GB1550173A (en)	1979-08-08
NL189560C (nl)	1993-05-17
JPS6051457B2 (ja)	1985-11-14
IT1064741B (it)	1985-02-25
ATA621376A (de)	1979-01-15
DE2636879C2 (de)	1985-11-28
NL7608973A (nl)	1977-02-24
JPS5225732A (en)	1977-02-25
FR2321467A1 (fr)	1977-03-18
NL189560B (nl)	1992-12-16
BE845366A (fr)	1977-02-21
AT351682B (de)	1979-08-10
FR2321467B1 (fr)	1982-04-09

Legal Events

Date	Code	Title	Description
1990-02-15	PUE	Assignment	Owner name: F. HOFFMANN-LA ROCHE AG
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2505869C3 (de)	1978-05-18	Verfahren zur Herstellung von symmetrischen Carotinoiden
EP0298404B1 (fr)	1994-01-12	Polyènes sulfoniques
EP0004621B1 (fr)	1984-05-09	Procédé de préparation en plusieurs étapes de la zéaxanthine et de l'alloxanthine à partir de dérivés de la cyclohexanone ou du cyclohexanol; dérivés de la cyclohexanone et du cyclohexanol
DE10164041B4 (de)	2008-10-23	Verfahren zur Herstellung von Vitamin-A-Estern
EP0015436B1 (fr)	1982-02-03	Procédé de fabrication stéréospécifique de composés appartenant à la famille des vitamines K1 et K2 ainsi que des produits de départ pour ce procédé
EP0005749A2 (fr)	1979-12-12	Dérivés de la cyclohexéne, procédé de leur préparation, ainsi que leur utilisation
DE60103179T2 (de)	2005-05-04	Synthese von r-(+)-alpha-liponsäure
DE2548883B2 (de)	1981-08-06	Verfahren zur photochemischen Isomerisierung von Vitamin A-Verbindungen
DE2636879A1 (de)	1977-03-03	Verfahren zur herstellung von polyenverbindungen
EP0031875B1 (fr)	1983-05-18	Procédé pour la préparation de dérivés de cyclohexène
DE2439860A1 (de)	1975-03-06	Isomerisierung von vitamin a, von analogen und derivaten hiervon
DE3120969C2 (fr)	1989-01-05
DE1026745B (de)	1958-03-27	Verfahren zur Herstellung von Vitamin-A-Saeure bzw. ihren Estern
DE1068709B (de)	1959-11-12	Verfahren zur Synthese von Verbindungen der Axerophtyliden-Reihe
EP0110245A1 (fr)	1984-06-13	Procédé de préparation du 1,3-diacétoxy-2-méthylène-propane
EP0454002A2 (fr)	1991-10-30	Procédé de déshydratation
EP0294557B1 (fr)	1992-07-08	Procédé de préparation du 3-phényl-2-méthylpropanol et de ses dérivés alkyliques para-substitués
DE2319518C3 (de)	1977-03-10	Terpenische 2-methylbutadienylsulfone
DE2829346A1 (de)	1979-01-25	Verfahren zur herstellung von substituierten benzaldehyden
DE1618782A1 (de)	1971-01-28	Neue tricyclische Verbindungen und Verfahren zur Herstellung von tricyclischen Verbindungen
DE2534859C2 (de)	1982-12-30	Verfahren zur Herstellung von 2(E)-,4(Z)- ungesättigten Estern
EP0109625B1 (fr)	1986-10-08	Procédé pour la préparation de la dihydro-4,4-diméthyl-2,3-furannedione
AT319909B (de)	1975-01-10	Verfahren zur Herstellung von neuen Carbonylverbindungen
US4452992A (en)	1984-06-05	Process for the production of ethoxycarbonylmethyl 5-(2,6-dichloro-4-trifluoro-methylphenoxy)-2-nitro-α-phenoxy-propionate
CH635317A5 (de)	1983-03-31	Derivate des 8-dehydro-vitamins-a sowie verfahren zu deren herstellung.