GB1013907A - Alkene derivatives - Google Patents

Alkene derivatives

Info

Publication number
GB1013907A
GB1013907A GB34989/62A GB3498962A GB1013907A GB 1013907 A GB1013907 A GB 1013907A GB 34989/62 A GB34989/62 A GB 34989/62A GB 3498962 A GB3498962 A GB 3498962A GB 1013907 A GB1013907 A GB 1013907A
Authority
GB
United Kingdom
Prior art keywords
prepared
stands
formula
compound
alkyl
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.)
Expired
Application number
GB34989/62A
Inventor
Michael John Kennedy Harper
Dora Nellie Richardson
Arthur Leonard Walpole
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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
Priority to BE637389D priority Critical patent/BE637389A/xx
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB34989/62A priority patent/GB1013907A/en
Priority to DE19631468088 priority patent/DE1468088C/en
Priority to FR947499A priority patent/FR1502607A/en
Priority to BR152734/63A priority patent/BR6352734D0/en
Priority to DK433463AA priority patent/DK118655B/en
Priority to CH1130363A priority patent/CH441286A/en
Priority to CH277067A priority patent/CH446289A/en
Priority to FR957012A priority patent/FR3103M/en
Priority to GB30755/65A priority patent/GB1064629A/en
Publication of GB1013907A publication Critical patent/GB1013907A/en
Priority to CH405466A priority patent/CH538447A/en
Priority to BR178265/66A priority patent/BR6678265D0/en
Priority to BE678807D priority patent/BE678807A/xx
Priority to DK199466A priority patent/DK124677B/en
Priority to FR58962A priority patent/FR90418E/en
Priority to DE19661568834 priority patent/DE1568834A1/en
Priority to FR70564A priority patent/FR6841M/fr
Priority to GB18491/67A priority patent/GB1146405A/en
Priority to DK432067AA priority patent/DK117953B/en
Priority to CH507468A priority patent/CH500165A/en
Priority to FR148833A priority patent/FR95156E/en
Priority to DE19681768020 priority patent/DE1768020A1/en
Priority to FR318D priority patent/FR318F/fr
Priority to DK355571AA priority patent/DK127777B/en
Priority to US06/600,224 priority patent/US4536516A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
    • C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
    • C07C49/796—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring polycyclic

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of the formula <FORM:1013907/C2/1> and their acid addition salts, wherein the R1R2N(CH2)2O- group is borne in the m- or p-position relative to the CR3=CR4R5 group, R1 and R2 which may be the same or different, stand for C1-6 alkyl groups or the NR1R2 group stands for a nitrogen-containing heterocyclic radical, wherein n is an integer from 2 to 6, R3 and R4, which may be the same or different stand for aryl radicals, optionally substituted by one or more alkyl, alkoxy, and/or dialkylaminoalkoxy radicals and/or one or more halogen atoms and R5 stands for an alkyl, alkenyl or aralkyl radical and the preparation thereof (a) by dehydrating a compound of the formula <FORM:1013907/C2/2> where R stands for the group CR3(OH).CHR4R5 or CR3.C(OH)R4R5\h or (b) by reacting an aminoalkyl halide R1R2N(CH2)nX, wherein X is a halogen atom with a compound of the formula <FORM:1013907/C2/3> where M stands for hydrogen or an alkali metal atom. Compounds of formula II, wherein R is CR3(OH)CHR4R5 are prepared from a Grignard reagent <FORM:1013907/C2/4> and a compound R3COCHR4R5 or from a compound <FORM:1013907/C2/5> and a Grignard reagent R3MgX and Compounds II, wherein R is -CHR3C(OH)R4R5 are prepared from a Grignard R4.MgX or R5MgX with a compound of the formula <FORM:1013907/C2/6> wherein R6 stands for R5 or R4 respectively. Compounds of Formula IV and V are prepared by reaction of an aminoalkyl halide on the corresponding substituted phenol. Compounds of the Formula III where M is hydrogen are prepared through the methyl ether which in turn is prepared by reacting anisyl magnesium halide with an appropriate carbonyl compound and dehydrating the alkanol so formed. 4-Chloro-a -methyldesoxybenzoi is prepared by reaction of 4-chlorodesoxybenzoin with methyl iodide. Similarly is prepared a ,4-dimethyldesoxybenzoin, 41 - chloro - 4 - methoxy - a - methyldesoxybenzoin, a - isopropyl - a - propyl- and a - allyl - 4 - methoxydesoxybenzoins. 4-Hydroxy-a -methyldesoxybenzoin is prepared by demethylation of the methyl ether. Similarly are prepared 4-hydroxy - a - propyl-, -isopropyl- and -allyldesoxybenzoins.ALSO:Pharmaceutical and veterinary compositions, useful for the modification of endocrine status in man and animals and for the control of hormone-dependent tumours or for the management of the sexual cycle and abenations thereof, comprise compounds of the formula <FORM:1013907/A5-A6/1> or acid addition salts thereof wherein the R1R2N(CH2)n O-group is borne in the m or p position relative to the -CR3=CR4R5 group, R1 and R2, which may be the same or different, stand for C1-6 alkyl radicals or the NR1R2 group stands for a N-containing heterocyclic radical, n stands for an integer from 2 to 6, R3 and R4, which may be the same or different stand for aryl radicals optionally substituted by one or more alkyl, alkoxy, and/or dialhylamino-alkyl radicals and/or one or more halogen atoms, and R5 stands for an alkyl, alkenyl or aralkyl radical, in admixture with a pharmaceutically-acceptable carrier a diluent and optionally together with at least one compound which is known to effect the endocrine status in man and animals, e.g. a known orally active progestational agent. The compositions may be formulated as tablets, capsules solutions, suspensions, dispersible powders suitable for the preparation of liquid suspensions, mixtures with animal foodstuffs or premixes suitable for addition to animal foodstuffs, sterile solutions for injection or sterile dispersible powders suitable for the preparation of sterile liquid suspensions.
GB34989/62A 1962-09-13 1962-09-13 Alkene derivatives Expired GB1013907A (en)

Priority Applications (25)

Application Number Priority Date Filing Date Title
BE637389D BE637389A (en) 1962-09-13
GB34989/62A GB1013907A (en) 1962-09-13 1962-09-13 Alkene derivatives
DE19631468088 DE1468088C (en) 1962-09-13 1963-09-05 Triphenylalkenamino ethers and processes for their preparation
CH277067A CH446289A (en) 1962-09-13 1963-09-13 Process for the preparation of alkene derivatives
BR152734/63A BR6352734D0 (en) 1962-09-13 1963-09-13 PROCESS TO PREPARE NEW ALKENIC DERIVATIVES
FR947499A FR1502607A (en) 1962-09-13 1963-09-13 New alkenic derivatives
DK433463AA DK118655B (en) 1962-09-13 1963-09-13 Analogous process for the preparation of p-aminoalkoxyphenylalkene derivatives.
CH1130363A CH441286A (en) 1962-09-13 1963-09-13 Process for the preparation of alkene derivatives
FR957012A FR3103M (en) 1962-09-13 1963-12-12 Medicines based on alkenic derivatives.
GB30755/65A GB1064629A (en) 1962-09-13 1965-07-20 Alkene derivatives
CH405466A CH538447A (en) 1962-09-13 1966-03-21 Process for the preparation of the cis or trans isomers of alkene derivatives
BR178265/66A BR6678265D0 (en) 1962-09-13 1966-03-29 ALKENE DERIVATIVES AND PROCESS FOR THEIR PREPARATION
BE678807D BE678807A (en) 1962-09-13 1966-03-31
DK199466A DK124677B (en) 1962-09-13 1966-04-19 Analogous process for the preparation of trans isomers of p- (aminoalkoxy) phenyl-stilbene derivatives.
FR58962A FR90418E (en) 1962-09-13 1966-04-25 New alkenic derivatives
DE19661568834 DE1568834A1 (en) 1962-09-13 1966-04-28 Process for the preparation of cis and trans isomers of alkene derivatives
FR70564A FR6841M (en) 1962-09-13 1966-07-22
GB18491/67A GB1146405A (en) 1962-09-13 1967-04-21 Alkene derivatives
DK432067AA DK117953B (en) 1962-09-13 1967-08-25 Analogous process for the preparation of p-aminoalkoxyphenylalkene derivatives.
CH507468A CH500165A (en) 1962-09-13 1968-04-05 Cis and trans 1-p-b-methyl-or ethyl- -amino-ethoxyphenyl-1 2-diphenyl - prop or but -1-ene
FR148833A FR95156E (en) 1962-09-13 1968-04-19 New alkenic derivatives.
DE19681768020 DE1768020A1 (en) 1962-09-13 1968-05-21 Alkene derivatives and processes for their preparation
FR318D FR318F (en) 1962-09-13 1968-07-18
DK355571AA DK127777B (en) 1962-09-13 1971-07-19 p- (Aminoalkoxy) phenyl stilbene derivatives for use as contraceptives.
US06/600,224 US4536516A (en) 1962-09-13 1984-04-17 Alkene derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB34989/62A GB1013907A (en) 1962-09-13 1962-09-13 Alkene derivatives

Publications (1)

Publication Number Publication Date
GB1013907A true GB1013907A (en) 1965-12-22

Family

ID=10372495

Family Applications (1)

Application Number Title Priority Date Filing Date
GB34989/62A Expired GB1013907A (en) 1962-09-13 1962-09-13 Alkene derivatives

Country Status (2)

Country Link
FR (1) FR3103M (en)
GB (1) GB1013907A (en)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3121175A1 (en) 1981-05-27 1982-12-16 Klinge Pharma GmbH, 8000 München ERYTHRO-1,2,3-TRIPHENYL-1-PENTANONE DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS
US4536516A (en) * 1962-09-13 1985-08-20 Imperial Chemical Industries Plc Alkene derivatives
US4656187A (en) * 1981-08-03 1987-04-07 Eli Lilly And Company Treatment of mammary cancer
US4897503A (en) * 1986-06-16 1990-01-30 Taiho Pharmaceutical 1,1,2-triaryl-1-alkene derivatives
US4960937A (en) * 1987-10-29 1990-10-02 Klinge Pharma Gmbh Process for the preparation of trans-1,1,2-triphenyl-but-1-ene derivatives
WO1994005617A1 (en) * 1992-08-25 1994-03-17 New York University Synthesis of haloenones and aryl or alkyl substituted enones or alkenes
US5354861A (en) * 1992-11-04 1994-10-11 National University Of Singapore 2-(benzyl)-3-arylbenzofurans as antitumour and hypocholesterolemic agents
US5472962A (en) * 1991-11-15 1995-12-05 Teikoku Hormone Mfg. Co., Ltd. Benzothiophene derivative
US5525633A (en) * 1993-09-24 1996-06-11 Merrell Dow Pharmaceuticals Inc. Triaryl-ethylene derivatives
US5691384A (en) * 1994-11-29 1997-11-25 Hoechst Marion Roussel, Inc. Method of using triaryl-ethylene derivatives in the treatment and prevention of osteoporosis
US5693674A (en) * 1994-11-29 1997-12-02 Hoechst Marion Roussel, Inc. Method of using triaryl-ethylene derivatives in the treatment and prevention of osteoporosis
WO2002066415A2 (en) * 2001-02-20 2002-08-29 The Provost, Fellows And Scholars Of The College Of The Holy And Undivided Trinity Of Queen Elizabeth Near Dublin Non-steroidal modulators of estrogen receptors
US7309702B2 (en) 1997-12-16 2007-12-18 Avera Pharmaceuticals, Inc. Arylpiperazines having activity at the serotonin 1A receptor
US8377985B2 (en) 2005-07-18 2013-02-19 Bipar Sciences, Inc. Treatment of cancer

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4206234A (en) * 1977-08-22 1980-06-03 Imperial Chemical Industries Limited Triphenylbut-1-ene derivatives and pharmaceutical compositions and uses thereof
GB2042519B (en) * 1979-01-17 1983-03-23 Biorex Laboratories Ltd 1,1,2-triphenylethane and -ehylene derivatives

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4536516A (en) * 1962-09-13 1985-08-20 Imperial Chemical Industries Plc Alkene derivatives
DE3121175A1 (en) 1981-05-27 1982-12-16 Klinge Pharma GmbH, 8000 München ERYTHRO-1,2,3-TRIPHENYL-1-PENTANONE DERIVATIVES AND METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS
US4656187A (en) * 1981-08-03 1987-04-07 Eli Lilly And Company Treatment of mammary cancer
US4897503A (en) * 1986-06-16 1990-01-30 Taiho Pharmaceutical 1,1,2-triaryl-1-alkene derivatives
US4960937A (en) * 1987-10-29 1990-10-02 Klinge Pharma Gmbh Process for the preparation of trans-1,1,2-triphenyl-but-1-ene derivatives
US5472962A (en) * 1991-11-15 1995-12-05 Teikoku Hormone Mfg. Co., Ltd. Benzothiophene derivative
WO1994005617A1 (en) * 1992-08-25 1994-03-17 New York University Synthesis of haloenones and aryl or alkyl substituted enones or alkenes
US5446203A (en) * 1992-08-25 1995-08-29 New York University Synthesis of haloenones and aryl or alkyl substituted enones or alkenes
US5459139A (en) * 1992-11-04 1995-10-17 National University Of Singapore 2-(benzyl)-3-arylbenzofurans as antitumour and hypocholesterolemic agents
US5354861A (en) * 1992-11-04 1994-10-11 National University Of Singapore 2-(benzyl)-3-arylbenzofurans as antitumour and hypocholesterolemic agents
US5525633A (en) * 1993-09-24 1996-06-11 Merrell Dow Pharmaceuticals Inc. Triaryl-ethylene derivatives
US5691384A (en) * 1994-11-29 1997-11-25 Hoechst Marion Roussel, Inc. Method of using triaryl-ethylene derivatives in the treatment and prevention of osteoporosis
US5693674A (en) * 1994-11-29 1997-12-02 Hoechst Marion Roussel, Inc. Method of using triaryl-ethylene derivatives in the treatment and prevention of osteoporosis
US7309702B2 (en) 1997-12-16 2007-12-18 Avera Pharmaceuticals, Inc. Arylpiperazines having activity at the serotonin 1A receptor
CN100355714C (en) * 1997-12-16 2007-12-19 伊莱利利公司 Arylpiperazines having 5-hydroxyl-typtamine activity
WO2002066415A2 (en) * 2001-02-20 2002-08-29 The Provost, Fellows And Scholars Of The College Of The Holy And Undivided Trinity Of Queen Elizabeth Near Dublin Non-steroidal modulators of estrogen receptors
WO2002066415A3 (en) * 2001-02-20 2002-12-12 Trinity College Dublin Non-steroidal modulators of estrogen receptors
US8377985B2 (en) 2005-07-18 2013-02-19 Bipar Sciences, Inc. Treatment of cancer

Also Published As

Publication number Publication date
FR3103M (en) 1965-02-01

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