IE41801L - Polyene compounds - Google Patents

Polyene compounds

Info

Publication number
IE41801L
IE41801L IE752098A IE209875A IE41801L IE 41801 L IE41801 L IE 41801L IE 752098 A IE752098 A IE 752098A IE 209875 A IE209875 A IE 209875A IE 41801 L IE41801 L IE 41801L
Authority
IE
Ireland
Prior art keywords
group
symbol
formula
formyl
lower alkyl
Prior art date
Application number
IE752098A
Other versions
IE41801B1 (en
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 IE41801L publication Critical patent/IE41801L/en
Publication of IE41801B1 publication Critical patent/IE41801B1/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/28Phosphorus compounds with one or more P—C bonds
    • C07F9/54Quaternary phosphonium compounds
    • C07F9/5456Arylalkanephosphonium compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/08Antiallergic agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/23Preparation of halogenated hydrocarbons by dehalogenation
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/07Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
    • C07C205/11Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
    • C07C205/12Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/13Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
    • C07C205/20Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C07C205/21Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C205/22Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring having one nitro groups bound to the ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/37Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/045Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of a group bound to the ring by nitrogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01Preparation of ethers
    • C07C41/16Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01Preparation of ethers
    • C07C41/18Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/515Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40Unsaturated compounds
    • C07C59/58Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pulmonology (AREA)
  • Immunology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Dermatology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

1514975 Preparation of polyene compounds; phosphonium compounds F HOFFMANN-LA ROCHE & CO AG 26 Sept 1975 [26 Sept 1974] 39545/75 Heading C2C Polyene compounds of the general formula wherein one of the symbols R 1 and R 2 represents a halogen atom or a lower alkyl group and the other symbol represents a halogen atom or a lower alkoxy group, the symbols R 3 and R 5 each represent a hydrogen or halogen atom or a lower alkyl group with the proviso that one of the symbols R 3 and R 5 represents other than a halogen atom, the symbol R 4 represents a halogen atom or a lower alkoxy, amino, mono- (lower alkyl)amino or di-(lower alkyl)amino group and the symbol R 6 represents a formyl, hydroxymethyl, alkoxymethyl, alkanoyloxymethyl, carboxyl, alkoxycarbonyl, alkenoxycarbonyl. alkynoxycarbonyl, carbamoyl, mono- (lower alkyl)carbamoyl, di - (lower alkyl)carbamoyl or N-hetero-cyclylcarbonyl group, and salts thereof, are prepared by reacting a compound of the general formula with a compound of the general formula wherein the symbol m stands for zero and the symbol n stands for 1 or the symbol m stands for 1 and the symbol n stands for zero, one of the symbols A and B represents the formyl group and the other symbol represents either a triarylphosphiniummethyl group of the formula in which the symbol X represents an aryl group and the symbol Y represents the anion of the organic or inorganic acid, or a dialkoxyphosphinylmethyl group of the formula in which the symbol Z represents an alkoxy group; or one of the symbols A and B represents a halomethyl, alkylsulphonyloxymethyl or arylsulphonyloxymethyl group and the other symbol represents a sulphonylmethyl group of the formula in which the symbol E represents an aryl or aralkenyl group which may carry one or more electron-repelling to electron-weakly attracting substituents; the symbol R 7 represents a carboxyl, alkoxycarbonyl, alkenoxycarbonyl, alkynoxycarbonyl, di - (lower alkyl)carbamoyl or N-heterocyclylcarbonyl group; or the symbol R 2 also represents an alkoxymethyl or alkanoyloxymethyl group when the symbol B represents the formyl group; or the symbol R 7 also represents a formyl, alkoxymethyl or alkanoyloxymethyl group when the symbol B represents a halomethyl, alkylsulphonyloxymethyl or arylsulphonyloxymethyl group; or the symbol R 7 also represents a formyl group when the symbol B represents a triarylphosphoniummethyl group, a dialkoxyphosphinylmethyl group or a sulphonylmethyl group, and cleaving off a sulphone group which may be present in the reaction product to form an additional carbon-carbon bond, and, if desired, converting an acid obtained or an amine obtained into a salt, or converting a carboxylic acid of Formula I into a carboxylic acid ester of Formula I or into an amide of Formula I, or converting a carboxylic acid ester of Formula I into a carboxylic acid of Formula I or into an amide of Formula I, or reducing a carboxylic acid of Formula I into a carboxylie acid ester of Formula I to the corresponding alcohol of Formula I and if desired etherifying or esterifying said alcohol, or saponifying an alcohol ester of Formula I, or oxidizing an alcohol or alcohol ester of Formula I to the corresponding carboxylic acid. The compounds have pharmaceutical properties. Phosphonium compound starting materials of the skeletal structure of Formula II in which A represents a triaryl phosphonium group -CH 2 -P[X]<SP>+</SP> 3 Y- in which X refers to an aryl group and Y is Cl are prepared in Examples 1 to 6. Other intermediates are 2 - chloro - 3,5,6 - trimethyl - benzene, 2- chloro - 4 - nitro - 3,5,6 - methyl benzene, 4 - amino - 2 - chloro - 3,5,6 - trimethyl benzene, 2 - chloro - 4 - hydroxy - 3,5,6 - trimethyl benzene, 2 - chloro - 4 - methoxy - 3,5,6- trimethyl benzene - 4,4<SP>1 </SP>- dimethoxy - 3- methyl - but - 1 - yne - 3 - ol 2 formyl - 4- chloro - but - 2 - ene and 7 - formyl - 3 - methylocta - 2,4,6 - triene - 1 - oio acid ethyl ester. [GB1514975A]
IE2098/75A 1974-09-26 1975-09-25 Polyene compounds, their preparation and compositions containing them IE41801B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1303274A CH605562A5 (en) 1974-09-26 1974-09-26

Publications (2)

Publication Number Publication Date
IE41801L true IE41801L (en) 1976-03-26
IE41801B1 IE41801B1 (en) 1980-03-26

Family

ID=4388688

Family Applications (1)

Application Number Title Priority Date Filing Date
IE2098/75A IE41801B1 (en) 1974-09-26 1975-09-25 Polyene compounds, their preparation and compositions containing them

Country Status (22)

Country Link
JP (1) JPS5951531B2 (en)
AR (1) AR212858A1 (en)
AT (1) AT346311B (en)
BE (1) BE833784A (en)
BR (1) BR7506154A (en)
CA (1) CA1050042A (en)
CH (1) CH605562A5 (en)
CU (1) CU34345A (en)
DD (1) DD122072A5 (en)
DE (1) DE2542612A1 (en)
FR (1) FR2285864B1 (en)
GB (1) GB1514975A (en)
HU (1) HU172958B (en)
IE (1) IE41801B1 (en)
IL (1) IL47929A (en)
LU (1) LU73452A1 (en)
NL (1) NL177913C (en)
NZ (1) NZ178425A (en)
PH (1) PH12883A (en)
SU (1) SU623515A3 (en)
YU (1) YU40124B (en)
ZA (1) ZA755208B (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4321209A (en) 1975-11-14 1982-03-23 Hoffmann-La Roche Inc. Fluorinated aromatic polyenes
US4375563A (en) 1975-11-14 1983-03-01 Hoffmann-La Roche Inc. Fluorinated aromatic 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
US4201727A (en) 1976-11-14 1980-05-06 Hoffmann-La Roche Inc. Fluorinated aromatic polyenes
US4299995A (en) 1979-05-10 1981-11-10 Hoffmann-La Roche Inc. Fluorinated polyenes
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
CA1111441A (en) 1976-12-20 1981-10-27 Werner Bollag Polyene compounds
US4200647A (en) * 1977-12-21 1980-04-29 Hoffmann-La Roche Inc. Vitamin A compositions to treat rheumatic disease
US4642318A (en) * 1982-11-17 1987-02-10 Klaus Wolff Method for decreasing radiation load in PUVA therapy
ZA854828B (en) * 1984-07-27 1986-03-26 Hoffmann La Roche Phenyl nonatetraenoic acid derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1109671B (en) * 1958-10-17 1961-06-29 Basf Ag Process for the production of ª ‡, ª ‰ -unsaturated carboxylic acid esters or the free acids

Also Published As

Publication number Publication date
IE41801B1 (en) 1980-03-26
DD122072A5 (en) 1976-09-12
NL177913C (en) 1985-12-16
ZA755208B (en) 1976-07-28
JPS51125233A (en) 1976-11-01
FR2285864B1 (en) 1980-03-28
IL47929A0 (en) 1975-11-25
HU172958B (en) 1979-01-28
JPS5951531B2 (en) 1984-12-14
ATA734775A (en) 1978-03-15
AT346311B (en) 1978-11-10
BR7506154A (en) 1976-08-03
CU34345A (en) 1979-09-08
CA1050042A (en) 1979-03-06
AR212858A1 (en) 1978-10-31
GB1514975A (en) 1978-06-21
YU228775A (en) 1983-01-21
YU40124B (en) 1985-08-31
PH12883A (en) 1979-09-28
FR2285864A1 (en) 1976-04-23
NZ178425A (en) 1978-03-06
SU623515A3 (en) 1978-09-05
AU8418775A (en) 1977-02-24
DE2542612A1 (en) 1976-04-22
DE2542612C2 (en) 1987-09-10
CH605562A5 (en) 1978-09-29
NL7510778A (en) 1976-03-30
IL47929A (en) 1978-07-31
LU73452A1 (en) 1977-05-16
BE833784A (en) 1976-03-25

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