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WO1992019627A3 - Phosphonates and phosphinates as anti-cancer, -inflammatory, -allergy and -myocarditis agents - Google Patents

Phosphonates and phosphinates as anti-cancer, -inflammatory, -allergy and -myocarditis agents Download PDF

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Publication number
WO1992019627A3
WO1992019627A3 PCT/CA1992/000165 CA9200165W WO9219627A3 WO 1992019627 A3 WO1992019627 A3 WO 1992019627A3 CA 9200165 W CA9200165 W CA 9200165W WO 9219627 A3 WO9219627 A3 WO 9219627A3
Authority
WO
WIPO (PCT)
Prior art keywords
group
head group
allergy
inflammatory
cancer
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.)
Ceased
Application number
PCT/CA1992/000165
Other languages
French (fr)
Other versions
WO1992019627A2 (en
Inventor
Hassan Salari
Robert Bittman
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.)
University of British Columbia
Original Assignee
University of British Columbia
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 University of British Columbia filed Critical University of British Columbia
Publication of WO1992019627A2 publication Critical patent/WO1992019627A2/en
Publication of WO1992019627A3 publication Critical patent/WO1992019627A3/en
Anticipated expiration legal-status Critical
Ceased 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
    • C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4081—Esters with cycloaliphatic alcohols
    • 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
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
    • 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
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/303—Cycloaliphatic acids
    • 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
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
    • 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
    • C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4075—Esters with hydroxyalkyl compounds

Landscapes

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

Abstract

This invention pertains to the synthesis and use as therapeutic agents of a group of substances with a glycerol backbone or aliphatic chain structure linked to a phosphorus atom and a polar head group. Depending on the polar head group, the substance has anti-cancer, anti-inflammatory, anti-allergy or anti-cardiovascular disease properties. Compounds of formulas (I) and (II), wherein n is O to 14 and R1 is an alkyl group of C12-C20, R2 is a methyl group, and wherein R3 is an inositol analog head group, a (CH2)mN+(CH3)3 group with m = 2 to 10, a serine head group, or an ethanolamine head group, or of formula (III), wherein R1 and R2 are as described above, n = 0 or 1, and R3 is (CH2)mN+(CH3)3 (m=2-10) are claimed. This invention also pertains to the synthesis and use as therapeutic agents of a group of substances that have no glycerol backbone but have an aliphatic chain structure linked directly to a phosphorus atom of the general formula R-P(0)(0-)OR' wherein R is a long-chain alkyl group such as hexadecyl or octadecyl and R' is a head group such as choline, glycerol, inositol, ethanolamine, or serine.
PCT/CA1992/000165 1991-04-25 1992-04-21 Phosphonates and phosphinates as anti-cancer, -inflammatory, -allergy and -myocarditis agents Ceased WO1992019627A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US69245291A 1991-04-25 1991-04-25
US692,452 1991-04-25

Publications (2)

Publication Number Publication Date
WO1992019627A2 WO1992019627A2 (en) 1992-11-12
WO1992019627A3 true WO1992019627A3 (en) 1993-05-13

Family

ID=24780645

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA1992/000165 Ceased WO1992019627A2 (en) 1991-04-25 1992-04-21 Phosphonates and phosphinates as anti-cancer, -inflammatory, -allergy and -myocarditis agents

Country Status (2)

Country Link
EP (1) EP0581793A1 (en)
WO (1) WO1992019627A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE9600194D0 (en) * 1996-01-19 1996-01-19 Perstorp Ab A new chemical compound
CA2438414A1 (en) * 2001-02-21 2002-09-06 The Research Foundation Of The City University Of New York Enantiomers of unsaturated alkyllysophosphonocholines and use as anti-neoplastics
WO2004062594A2 (en) * 2003-01-09 2004-07-29 Zeneus Pharma Limited Antineoplastic ether lipid compounds with modifications at the sn-3 carbon

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2619686A1 (en) * 1976-05-04 1977-11-24 Max Planck Gesellschaft ANTI-TUMOR AGENTS
EP0092190A2 (en) * 1982-04-19 1983-10-26 Fujisawa Pharmaceutical Co., Ltd. Phospholipid derivatives, process for preparation thereof and pharmaceutical composition of the same
EP0108565A2 (en) * 1982-11-08 1984-05-16 Takeda Chemical Industries, Ltd. Phospholipids, their production and use thereof
US4515722A (en) * 1982-03-30 1985-05-07 Merck & Co., Inc. Phosphatidyl inositol analogs useful as anti-inflammatory/analgesic agents
US4640913A (en) * 1983-01-10 1987-02-03 American Cyanamid Company Phosphocholine derivatives having antihypertensive action
EP0338407A1 (en) * 1988-04-19 1989-10-25 Hafslund Nycomed Pharma Aktiengesellschaft New alkylphosphonoserines, methods for preparing them, and pharmaceutical substances containing them
JPH0669088A (en) * 1992-03-26 1994-03-11 Nec Kyushu Ltd Air-conditioning system

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2619686A1 (en) * 1976-05-04 1977-11-24 Max Planck Gesellschaft ANTI-TUMOR AGENTS
US4515722A (en) * 1982-03-30 1985-05-07 Merck & Co., Inc. Phosphatidyl inositol analogs useful as anti-inflammatory/analgesic agents
EP0092190A2 (en) * 1982-04-19 1983-10-26 Fujisawa Pharmaceutical Co., Ltd. Phospholipid derivatives, process for preparation thereof and pharmaceutical composition of the same
EP0108565A2 (en) * 1982-11-08 1984-05-16 Takeda Chemical Industries, Ltd. Phospholipids, their production and use thereof
US4640913A (en) * 1983-01-10 1987-02-03 American Cyanamid Company Phosphocholine derivatives having antihypertensive action
EP0338407A1 (en) * 1988-04-19 1989-10-25 Hafslund Nycomed Pharma Aktiengesellschaft New alkylphosphonoserines, methods for preparing them, and pharmaceutical substances containing them
JPH0669088A (en) * 1992-03-26 1994-03-11 Nec Kyushu Ltd Air-conditioning system

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 114, 1991, Columbus, Ohio, US; abstract no. 82129h, BRACHWITZ, H. ET AL. page 767 ; *
CHEMICAL ABSTRACTS, vol. 117, 1992, Columbus, Ohio, US; abstract no. 90393s, RIES, U.J. ET AL. page 794 ; *
JOURNAL OF MEDICINAL CHEMISTRY vol. 34, no. 4, 1 April 1991, pages 1377 - 1383 MEYER, K.L. ET AL. *
JOURNAL OF MEDICINAL CHEMISTRY vol. 34, no. 4, 1 April 1991, pages 1408 - 1414 PIANTADOSI, C. ET AL. *
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY vol. 110, 1988, pages 2665 - 2666 YUAN, W. ET AL. *

Also Published As

Publication number Publication date
WO1992019627A2 (en) 1992-11-12
EP0581793A1 (en) 1994-02-09

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