ATE357431T1 - Herstellung von retinoiden - Google Patents

Herstellung von retinoiden

Info

Publication number: ATE357431T1
Authority: AT; Austria
Prior art keywords: derivative; retinal; trimethyl; cyclohex; enyl
Prior art date: 2001-10-31

Application number

AT02779506T

Other languages

English (en)

Inventor

Alexander Radspieler

August Ruettimann

Original Assignee

Dsm Ip Assets Bv

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.)

2001-10-31

Filing date

2002-10-24

Publication date

2007-04-15

2002-10-24 Application filed by Dsm Ip Assets Bv filed Critical Dsm Ip Assets Bv

2007-04-15 Application granted granted Critical

2007-04-15 Publication of ATE357431T1 publication Critical patent/ATE357431T1/de

Links

238000004519 manufacturing process Methods 0.000 title abstract 2
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 abstract 6
230000002207 retinal effect Effects 0.000 abstract 6
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 abstract 3
VBRPATNPOOHKOF-UHFFFAOYSA-N 1,3,3-trimethyl-2-pent-4-en-1-ynylcyclohexene Chemical class CC1=C(C#CCC=C)C(C)(C)CCC1 VBRPATNPOOHKOF-UHFFFAOYSA-N 0.000 abstract 2
QPZSEXPGYPZJTN-UHFFFAOYSA-N 1,3,3-trimethyl-2-penta-1,4-dienylcyclohexene Chemical class CC1=C(C=CCC=C)C(C)(C)CCC1 QPZSEXPGYPZJTN-UHFFFAOYSA-N 0.000 abstract 2
HYYJILCKVXLAOV-UHFFFAOYSA-N 1,5,5-trimethyl-6-pent-4-en-1-ynylcyclohexene Chemical class CC1=CCCC(C)(C)C1C#CCC=C HYYJILCKVXLAOV-UHFFFAOYSA-N 0.000 abstract 2
OPCBOZPVSVXKFI-UHFFFAOYSA-N 1,5,5-trimethyl-6-pent-4-enylidenecyclohexene Chemical class CC1=CCCC(C)(C)C1=CCCC=C OPCBOZPVSVXKFI-UHFFFAOYSA-N 0.000 abstract 2
LWWWYGJHLHEITJ-UHFFFAOYSA-N 1,5,5-trimethyl-6-penta-1,4-dienylcyclohexene Chemical class CC1=CCCC(C)(C)C1C=CCC=C LWWWYGJHLHEITJ-UHFFFAOYSA-N 0.000 abstract 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 2
230000002378 acidificating effect Effects 0.000 abstract 2
235000019169 all-trans-retinol Nutrition 0.000 abstract 2
239000011717 all-trans-retinol Substances 0.000 abstract 2
230000015572 biosynthetic process Effects 0.000 abstract 2
238000000034 method Methods 0.000 abstract 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 1
239000002253 acid Substances 0.000 abstract 1
239000000654 additive Substances 0.000 abstract 1
239000003054 catalyst Substances 0.000 abstract 1
150000001875 compounds Chemical class 0.000 abstract 1
210000000987 immune system Anatomy 0.000 abstract 1
239000002184 metal Substances 0.000 abstract 1
239000000203 mixture Substances 0.000 abstract 1
239000002243 precursor Substances 0.000 abstract 1
238000002360 preparation method Methods 0.000 abstract 1
229960003471 retinol Drugs 0.000 abstract 1
235000020944 retinol Nutrition 0.000 abstract 1
239000011607 retinol Substances 0.000 abstract 1
239000007858 starting material Substances 0.000 abstract 1
239000000126 substance Substances 0.000 abstract 1
238000003786 synthesis reaction Methods 0.000 abstract 1
150000002266 vitamin A derivatives Chemical class 0.000 abstract 1
230000036642 wellbeing Effects 0.000 abstract 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
- C07C403/14—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 doubly-bound oxygen atoms
- 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
- C07C403/04—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 halogen atoms
- 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
- C07C403/08—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 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
- C07C403/06—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
- C07C403/10—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 etherified 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
- C07C403/06—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
- C07C403/22—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 sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
- 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)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

AT02779506T 2001-10-31 2002-10-24 Herstellung von retinoiden ATE357431T1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP01125965		2001-10-31

Publications (1)

Publication Number	Publication Date
ATE357431T1 true ATE357431T1 (de)	2007-04-15

Family

ID=8179126

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AT02779506T ATE357431T1 (de)	2001-10-31	2002-10-24	Herstellung von retinoiden

Country Status (9)

Country	Link
US (1)	US7067703B2 (de)
EP (1)	EP1442014B1 (de)
KR (1)	KR100939397B1 (de)
CN (1)	CN1261411C (de)
AT (1)	ATE357431T1 (de)
DE (1)	DE60219053T2 (de)
ES (1)	ES2282480T3 (de)
RU (1)	RU2318805C2 (de)
WO (1)	WO2003037856A1 (de)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2200699B1 (es)	2002-07-12	2005-10-01	Ragactives, S.L	Procedimiento para la separacion de r(-) y s(+)-5-(2-((2-(etoxifenoxi)etil)amino)propil-2-metoxibenceno-sulfonamida.
FR2894577B1 (fr) *	2005-12-14	2008-02-22	Fabre Pierre Dermo Cosmetique	Nouveaux composes polyinsatures, leur procede de preparation et les compositions les contenant.
RU2417983C1 (ru) *	2009-10-30	2011-05-10	Российская Федерация, От Имени Которой Выступает Министерство Образования И Науки Российской Федерации	Способ получения 11-цис-изомера ретиналя
CN113242852A (zh) *	2018-12-20	2021-08-10	帝斯曼知识产权资产管理有限公司	特定的α,β-不饱和羧酸酯
WO2020127158A1 (en) *	2018-12-20	2020-06-25	Dsm Ip Assets B.V.	Improved process to produce specific a,b-unsaturated carboxylates
WO2020212164A1 (en) *	2019-04-15	2020-10-22	Dsm Ip Assets B.V.	New process for the production of retinal
BR112022012342A2 (pt) *	2019-12-23	2022-09-06	Dsm Ip Assets Bv	Processo de desidrogenação
US12410117B2 (en) *	2020-03-31	2025-09-09	Dsm Ip Assets B.V.	Process for production of vitamin A
JP2023520137A (ja) *	2020-03-31	2023-05-16	ディーエスエムアイピーアセッツビー．ブイ．	テルペノイド中間体の生成方法
EP4168420B1 (de) *	2020-06-19	2024-11-13	DSM IP Assets B.V.	Verbessertes verfahren zur herstellung von spezifischen alpha,beta-ungesättigten carboxylaten
CN114907246B (zh) *	2021-02-08	2024-02-06	复旦大学	一种维生素a及其衍生物与其氘代化合物的全合成方法

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA677178A (en) *		1963-12-31	Eiter Karl	Process for the production of 6-(2',6',6'-trimethylcyclohexenyl-1')-4-methyl-hexa-3,5-diene-1-yne
SU93422A1 (ru) *	1951-07-05	1951-11-30	Г.С. Гусакова	Способ получени соединени 5-метил-7(1', 2', 3'-триметилциклогексен-2'-ил-2') гептатриен (2, 4, 6) карбоновой кислоты
US2834813A (en) *	1953-04-21	1958-05-13	Ortho Pharma Corp	Synthesis of vitamin a
US2945876A (en) *	1957-09-04	1960-07-19	Nopco Chem Co	Vitamin a intermediates and process for obtaining same
US3013081A (en)	1958-04-03	1961-12-12	Celanese Corp	Purification of ketones
FR1291622A (fr) *	1961-03-14	1962-04-27	Aec Chim Organ Biolog	Procédé de conversion d'un mélange de rétinènes isomères en aldéhyde de la vitamine a trans, trans-2, 6
GB1381437A (en) *	1972-04-24	1975-01-22	Scm Corp	Process for preparing vitamin
FR2622580B1 (fr) *	1987-10-29	1990-01-19	Centre Nat Rech Scient	Procede de preparation du retinal
FR2710911B1 (fr)	1993-10-07	1995-12-01	Rhone Poulenc Nutrition Animal	Nouveaux intermédiaires de préparation de la vitamine A et des caroténoïdes et leur procédé de préparation.
US5929288A (en)	1996-06-28	1999-07-27	Roche Vitamins Inc.	Process for manufacturing polyene aldehydes
FR2780970B1 (fr)	1998-07-10	2000-08-18	Rhone Poulenc Nutrition Animal	Procede de preparation de la vitamine a
ES2255206T3 (es) *	1998-08-05	2006-06-16	Dsm Ip Assets B.V.	Preparacion de 4,4'-diceto-carotenoides.

2002
- 2002-10-24 EP EP02779506A patent/EP1442014B1/de not_active Expired - Lifetime
- 2002-10-24 RU RU2004116696/04A patent/RU2318805C2/ru not_active IP Right Cessation
- 2002-10-24 DE DE60219053T patent/DE60219053T2/de not_active Expired - Lifetime
- 2002-10-24 US US10/494,079 patent/US7067703B2/en not_active Expired - Fee Related
- 2002-10-24 KR KR1020047006343A patent/KR100939397B1/ko not_active Expired - Fee Related
- 2002-10-24 AT AT02779506T patent/ATE357431T1/de not_active IP Right Cessation
- 2002-10-24 CN CNB028218841A patent/CN1261411C/zh not_active Expired - Fee Related
- 2002-10-24 ES ES02779506T patent/ES2282480T3/es not_active Expired - Lifetime
- 2002-10-24 WO PCT/EP2002/011878 patent/WO2003037856A1/en not_active Ceased

Also Published As

Publication number	Publication date
RU2004116696A (ru)	2005-05-27
WO2003037856A1 (en)	2003-05-08
RU2318805C2 (ru)	2008-03-10
KR100939397B1 (ko)	2010-01-28
DE60219053T2 (de)	2007-12-13
US20050014976A1 (en)	2005-01-20
DE60219053D1 (de)	2007-05-03
ES2282480T3 (es)	2007-10-16
EP1442014A1 (de)	2004-08-04
KR20050039711A (ko)	2005-04-29
CN1582273A (zh)	2005-02-16
EP1442014B1 (de)	2007-03-21
CN1261411C (zh)	2006-06-28
US7067703B2 (en)	2006-06-27

Legal Events

Date	Code	Title	Description
2007-09-15	RER	Ceased as to paragraph 5 lit. 3 law introducing patent treaties

Publication	Publication Date	Title
Negishi et al.	1991	Highly selective synthesis of vitamin A and its derivatives. Critical comparison of some known palladium-catalyzed alkenyl-alkenyl coupling reactions
DE60219053D1 (de)	2007-05-03	Herstellung von retinoiden
Trost et al.	1986	Chemo-, regio-, and diastereoselective alkylation via Lewis acid promoted substitutions of sulfones
Jurenka et al.	1989	Structural correlation between cuticular hydrocarbons and female contact sex pheromone of German cockroach Blattella germanica (L.)
Mori	2004	Pheromone synthesis
EP0996615B1 (de)	2002-09-11	Verbesserung der pigmentierungseffizienz eines natürlichen xanthophylls mittels isomerisierung
DE60230930D1 (de)	2009-03-05	An trans-lutein angereicherte xanthophyllesterkonzentrate und verfahren zu deren herstellung
US5747302A (en)	1998-05-05	Preparation of thiols with food-acceptable micro-organisms
WO2002034710A2 (fr)	2002-05-02	Intermediaires utiles pour la synthese de retinoides
Klaerner et al.	1988	Stereochemistry of the thermal rearrangement of bicyclo [3.2. 0] hept-2-ene to bicyclo [2.2. 1] hept-2-ene (norbornene).[1, 3] Carbon migration with predominant inversion
Rüttimann	1986	Recent advances in the synthesis of K-vitamins
US3558712A (en)	1971-01-26	Method for the synthesis of zeaxanthins,xanthophylis,and 3-oxo-beta carotene
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HUITRIC et al.	1962	Proton Magnetic Resonance Spectra, Stereochemistry, and Synthesis of 2-(Chlorophenyl) cyclohexanols1
Tashiro et al.	2008	Syntheses of 2-isopropyl-4, 5-dihydrothiazole and 6-hydroxy-6-methyl-3-heptanone, pheromone components of the male mouse, Mus musculus
Paruch et al.	1997	Lactones, 2. Synthesis of Enantiomeric pairs of lactones with the Pinane or the Fenchane system
CN109665977B (zh)	2021-06-15	高效的紫罗兰酮-α羟基磺酸钠加成物的生产方法
Kemmerer et al.	1944	Nature of carotenes in alfalfa
ITMI981093A1 (it)	1999-11-19	Procedimento per la preparazione dell'acido 13-cis-retinoico
US2894040A (en)	1959-07-07	Isomerization of terpenic alcohols
ES2158504T3 (es)	2001-09-01	Procedimiento para la obtencion de sales metalicas alcalinoterreas de beta-cetocompuestos alifaticos.
US3014052A (en)	1961-12-19	Polyenecarboxylic acids, esters and process of making same
Lopez-Sanchez et al.	2009	A convenient cross-Metathesis approach to trisporins