SE7410758L - - Google Patents

Info

Publication number
SE7410758L
SE7410758L SE7410758A SE7410758A SE7410758L SE 7410758 L SE7410758 L SE 7410758L SE 7410758 A SE7410758 A SE 7410758A SE 7410758 A SE7410758 A SE 7410758A SE 7410758 L SE7410758 L SE 7410758L
Authority
SE
Sweden
Prior art keywords
group
alkyl
carboxylic acid
alcohol
alkenoxycarbonyl
Prior art date
Application number
SE7410758A
Other versions
SE422787B (en
Inventor
B A Pawson
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.)
Filing date
Publication date
Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of SE7410758L publication Critical patent/SE7410758L/xx
Publication of SE422787B publication Critical patent/SE422787B/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or 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
    • C07C403/08—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
    • C07C403/12—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
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/298—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with manganese derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • 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)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1442108 Polyenes F HOFFMANN-LA ROCHE & CO AG 23 Aug 1974 [24 Aug 1973] 37142/74 Heading C2C Novel compounds I wherein R 1 represents a 2,6,6-trimethyl-cyclohex-1-en-1-yl group or a phenyl group which is substituted in the 2- and 6-positions by a halogen atom or a C 1 -C 6 alkyl or C 1 -C 6 alkoxy group and in at least one of the 3-, 4- and 5-positions by a halogen atom or a hydroxy, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenoxy, C 1 -C 6 alkanoyloxy, nitro, amino, mono(C 1 -C 6 alkyl)amino, di(C 1 -C 6 alkyl)amino, C 1 -C 6 alkanoylamino or N-heterocyclic group, and R 2 represents a formyl, hydroxymethyl, alkoxymethyl, alkanoyloxymethyl, carboxyl, alkoxycarbonyl, alkenoxycarbonyl, alkynoxycarbonyl, carbamoyl, mono- (C 1 -C 6 alkyl)carbamoyl, di(C 1 -C 6 alkyl) carbamoyl or N-heterocyclylcarbonyl group, are prepared by reacting a compound II with a compound III wherein one of the two symbols A and B represents an oxo group and the other represents a triarylphosphonium group of the formula -P[Y] 3 <SP>+</SP>Z<SP>-</SP>, in which Y represents an aryl group and Z represents the anion of an inorganic or organic acid, or a dialkoxyphosphinoxy group of the formula in which X represents an alkoxy group, R 1 has the significance given above, R 3 represents an alkoxymethyl, dialkoxymethyl, alkanoyloxymethyl, alkoxycarbonyl, alkenoxycarbonyl or alkynoxycarbonyl group when B represents an oxo group, and R 3 represents a formyl, hydroxymethyl, alkoxymethyl, dialkoxymethyl, carboxyl, alkoxycarbonyl, alkenoxycarbonyl or alkynoxycarbonyl group when B represents a triarylphosphonium group or a dialkoxyphosphinoxy group, and saponifying a diacetal obtained and, in optional sequence and if desired, etherifying or amidating a carboxylic acid obtained, or hydrolysing or amidating a carboxylic acid ester obtained, or reducing a carboxylic acid obtained or a carboxylic acid ester obtained to the corresponding alcohol and if desired etherifying or esterifying the resulting alcohol, or saponifying an alcohol ester obtained or oxidizing an alcohol obtained or alcohol ester obtained to the corresponding carboxylic acid. The following intermediates and starting materials are prepared in the examples: 3- methyl - 5 - R - pent - 2 - en - 1 - als, 4 - R - butan- 2 - ones, ethyl 3 - methyl - 5 - R - pent - 2 - en- 1 - oates and 3 - methyl - 5 - R - pent - 2 - en- 1-ols where R is 4-methoxy-2,3,6-trimethylphenyl-, 3 - chloro - 4 - methoxy - 2,6 - dimethyl - phenyl- or 4 - dimethylamino - 2,6= dimethylphenyl-; 4 - (4 - dimethylamino - 2,6- dimethylphenyl) - but - 3 - en - 2 - one; and 3- carbethoxy - 4 - (3 - chloro - 4 - methoxy - 2,6- dimethylphenyl)-butan-2-one. Pharmaceutical compositions having antineoplastic, anti-inflammatory, anti-allergic and anti-dermatitis activity for oral, parenteral or topical administration, comprise a compound I together with a pharmaceutical carrier.
SE7410758A 1973-08-24 1974-08-23 PROCEDURE FOR PREPARING CERTAIN STATEMENTS 3,7-DIMETHYL-9 - ((LAGALCOXY-LAGALKYL) -PHENYL) -NONA-2,4,6-TRIEN-1 ACIDS SE422787B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1219773A CH589619A5 (en) 1973-08-24 1973-08-24

Publications (2)

Publication Number Publication Date
SE7410758L true SE7410758L (en) 1975-02-25
SE422787B SE422787B (en) 1982-03-29

Family

ID=4380795

Family Applications (1)

Application Number Title Priority Date Filing Date
SE7410758A SE422787B (en) 1973-08-24 1974-08-23 PROCEDURE FOR PREPARING CERTAIN STATEMENTS 3,7-DIMETHYL-9 - ((LAGALCOXY-LAGALKYL) -PHENYL) -NONA-2,4,6-TRIEN-1 ACIDS

Country Status (11)

Country Link
JP (1) JPS5049244A (en)
BE (1) BE819117A (en)
CA (1) CA1030153A (en)
CH (1) CH589619A5 (en)
DE (1) DE2440525A1 (en)
DK (1) DK451974A (en)
FR (1) FR2241298B1 (en)
GB (1) GB1442108A (en)
NL (1) NL7411271A (en)
SE (1) SE422787B (en)
ZA (1) ZA744884B (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51125235A (en) * 1974-09-26 1976-11-01 Hoffmann La Roche Preparation of polyene compounds
US4338253A (en) 1975-11-14 1982-07-06 Hoffmann-La Roche Inc. Fluorinated aromatic polyenes
US4335248A (en) 1975-11-14 1982-06-15 Hoffmann-La Roche Inc. Fluorinated polyenes
US4375563A (en) 1975-11-14 1983-03-01 Hoffmann-La Roche Inc. Fluorinated aromatic polyenes
US4201727A (en) 1976-11-14 1980-05-06 Hoffmann-La Roche Inc. Fluorinated aromatic polyenes
US4321209A (en) 1975-11-14 1982-03-23 Hoffmann-La Roche Inc. Fluorinated aromatic polyenes
US4299995A (en) 1979-05-10 1981-11-10 Hoffmann-La Roche Inc. Fluorinated polyenes
US4266073A (en) * 1975-11-14 1981-05-05 Hoffmann-La Roche Inc. Fluorinated aromatic polyenes
US4395575A (en) 1975-11-14 1983-07-26 Hoffmann-La Roche, Inc. 5(Halophenyl)-2-fluoro-pentadienals
CA1111441A (en) 1976-12-20 1981-10-27 Werner Bollag Polyene compounds
US4642318A (en) * 1982-11-17 1987-02-10 Klaus Wolff Method for decreasing radiation load in PUVA therapy
US4526787A (en) * 1983-03-28 1985-07-02 Sri International N-heterocyclic retinoic acid analogues

Also Published As

Publication number Publication date
ZA744884B (en) 1975-08-27
GB1442108A (en) 1976-07-07
NL7411271A (en) 1975-02-26
JPS5049244A (en) 1975-05-01
DE2440525A1 (en) 1975-03-06
AU7214474A (en) 1976-02-12
CA1030153A (en) 1978-04-25
FR2241298B1 (en) 1978-08-18
CH589619A5 (en) 1977-07-15
SE422787B (en) 1982-03-29
DK451974A (en) 1975-04-28
FR2241298A1 (en) 1975-03-21
BE819117A (en) 1975-02-24

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