FR2285863A1 - Polyenes used against neoplasias and dermatosis - prepdby coupling 3 methyl-5 (substd. phenyl) pentenal and substd. phosphonomethylbutenoic acid ester - Google Patents

Polyenes used against neoplasias and dermatosis - prepdby coupling 3 methyl-5 (substd. phenyl) pentenal and substd. phosphonomethylbutenoic acid ester

Info

Publication number
FR2285863A1
FR2285863A1 FR7529225A FR7529225A FR2285863A1 FR 2285863 A1 FR2285863 A1 FR 2285863A1 FR 7529225 A FR7529225 A FR 7529225A FR 7529225 A FR7529225 A FR 7529225A FR 2285863 A1 FR2285863 A1 FR 2285863A1
Authority
FR
France
Prior art keywords
substd
halogen
alkyl
dermatosis
used against
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
FR7529225A
Other languages
French (fr)
Other versions
FR2285863B1 (en
Inventor
Werner Bollag
Rudolf Ruegg
Gottlieb Ryser
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of FR2285863A1 publication Critical patent/FR2285863A1/en
Application granted granted Critical
Publication of FR2285863B1 publication Critical patent/FR2285863B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4015—Esters of acyclic unsaturated acids
    • 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
    • C07C45/67—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
    • C07C45/68—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 increase in the number of carbon atoms
    • C07C45/72—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 increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—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 increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • 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
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
    • C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Polyenes of formula (I) (in which one of R1 and R2 = halogen or lower alkyl the other = halogen or lower alkoxy; R3 and R5 = H, lower alkyl or halogen; R4 = lower alkoxy, amino mono-or di(lower) alkyl-amino or halogen; R6 = formul, hydroxymethyl, alkoxymethyl, alkanoyloxymethyl, carboxyl, alkoxycarbonyl, alkenoxycarbonyl, alkinoxycarbonyl, carbamoyl, mono- or di-(lower)alkylcarbamoyl or N-heterocyclylcarbonyl), may be used for topical and systemic therapy and prophylaxis of benign and malignant neoplasias and pre-malignant lesions. They may also be used for topical and systemic therapy of acne. psoriasis and other dermatosis connected with increased or pathologically-altered cornification and of inflamed and allergic dermatological affections. (I) may also be used against disorders of mucus membranes with inflamed, degenerative or metaplastic alterations. The toxicity of (I) is ver low and tumor-inhibitory activity is significant. Dimethylanthracene- and croton oil-induced tumors regress in the papilloma test. Cpds. (I) are prepd. by reacting cpds. (II) and (III) in which one of A and B = oxo, the other either -P Y 3+Z- or Y = aryl; Z = the anion of an inorganic or org. acid; X = alkoxy; R7 (when B = oxo) = alkoxymethyl, dialkoxymethyl, alkanoyloxymethyl, alkoxycarbonyl, alkenoxycarbonyl or alkinoxycarbonyl. (II) and (III) are coupled using Witting reaction in the presence of acid-binding agent or an opt. alkyl-substd. alkeneoxide and opt. in solvent. Alternatively a Hormer reaction may be used with base and inert solvent. Carboxylic acids obtd. may be esterified or amidated, esters may be hydrolysed or either may be reduced to alcohols which may be etherified or esterified, then either saponified or oxidised.
FR7529225A 1974-09-26 1975-09-24 Polyenes used against neoplasias and dermatosis - prepdby coupling 3 methyl-5 (substd. phenyl) pentenal and substd. phosphonomethylbutenoic acid ester Granted FR2285863A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1303474 1974-09-26

Publications (2)

Publication Number Publication Date
FR2285863A1 true FR2285863A1 (en) 1976-04-23
FR2285863B1 FR2285863B1 (en) 1978-07-28

Family

ID=4388698

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7529225A Granted FR2285863A1 (en) 1974-09-26 1975-09-24 Polyenes used against neoplasias and dermatosis - prepdby coupling 3 methyl-5 (substd. phenyl) pentenal and substd. phosphonomethylbutenoic acid ester

Country Status (3)

Country Link
JP (1) JPS51125235A (en)
DE (1) DE2542600A1 (en)
FR (1) FR2285863A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2390428A1 (en) * 1977-05-04 1978-12-08 Hoffmann La Roche NEW POLYENE COMPOUNDS, THEIR PREPARATION AND THEIR APPLICATION AS MEDICINAL PRODUCTS

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4642318A (en) * 1982-11-17 1987-02-10 Klaus Wolff Method for decreasing radiation load in PUVA therapy

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2241298A1 (en) * 1973-08-24 1975-03-21 Hoffmann La Roche

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2241298A1 (en) * 1973-08-24 1975-03-21 Hoffmann La Roche

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2390428A1 (en) * 1977-05-04 1978-12-08 Hoffmann La Roche NEW POLYENE COMPOUNDS, THEIR PREPARATION AND THEIR APPLICATION AS MEDICINAL PRODUCTS

Also Published As

Publication number Publication date
FR2285863B1 (en) 1978-07-28
JPS51125235A (en) 1976-11-01
DE2542600A1 (en) 1976-04-22

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Legal Events

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ST Notification of lapse