WO1991009602A3 - Use of alkyl phospholipids as antiviral drugs, as well as new compounds - Google Patents
Use of alkyl phospholipids as antiviral drugs, as well as new compounds Download PDFInfo
- Publication number
- WO1991009602A3 WO1991009602A3 PCT/EP1990/002100 EP9002100W WO9109602A3 WO 1991009602 A3 WO1991009602 A3 WO 1991009602A3 EP 9002100 W EP9002100 W EP 9002100W WO 9109602 A3 WO9109602 A3 WO 9109602A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- alkane
- alkoxy
- chain
- antiviral drugs
- Prior art date
Links
- 239000003443 antiviral agent Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 title abstract 2
- -1 alkyl phospholipids Chemical class 0.000 title 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 5
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 150000002825 nitriles Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 206010038997 Retroviral infections Diseases 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 208000036142 Viral infection Diseases 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 150000003904 phospholipids Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 230000003612 virological effect Effects 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/683—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols
- A61K31/685—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols one of the hydroxy compounds having nitrogen atoms, e.g. phosphatidylserine, lecithin
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to the use of compounds of formula (I), where R1 is a straight-chain or branched, saturated or unsaturated aliphatic residue, in particular an alkyl residue, with 9 to 30 carbon atoms, which can also be part of a C¿5?-C7 cycloalkane ring and may be substituted with one or more hydroxy, halogen, nitrile, a C5-C7 cycloalkyl, phenyl, C1-C20 alkoxy carbonyl, C1-C20 alkyl carbonyl, C1-C20 alkyl carbamoyl, C1-C20 alkyl mercapto, C1-C20 alkane sulphinyl, C1-C20 alkane sulphonyl, C1-C20 acyl amino groups or by C1-C20 alkoxy which in turn can be substituted by phenyl, C1-C20 alkyl mercapto, C1-C20 alkane sulphinyl, C1-C20 alkane sulphonyl, C1-C20 acyl amino, C1-C20 alkoxy carbonyl, nitrile, hydroxy, C1-C20 alkoxy or C1-C20 alkyl carbamoyl, R?2¿ is a straight-chain or branched alkylene chain with 2 to 6, preferably 2 to 4, carbon atoms, R3 is hydrogen or a C¿1?-C6 alkyl group, and Y is an oxygen or a sulphur atom. The invention also relates to their pharmacologically acceptable salts and optical isomers for manufacturing antiviral drugs. Also described are selected new phospholipids and their use to manufacture drugs, in particular for treating viral or retroviral infections.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT91900254T ATE103177T1 (en) | 1989-12-23 | 1990-12-05 | USE OF ALKYLPHOSPHOLIPIDS AS ANTIVIRAL DRUGS, AND NEW COMPOUNDS. |
| DE91900254T DE59005139D1 (en) | 1989-12-23 | 1990-12-05 | USE OF ALKYLPHOSPHOLIPIDES AS ANTIVIRAL MEDICINAL PRODUCTS AND NEW COMPOUNDS. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3942933.4 | 1989-12-23 | ||
| DE3942933A DE3942933A1 (en) | 1989-12-23 | 1989-12-23 | USE OF ALKYLPHOSPHOLIPIDES AS ANTIVIRAL MEDICINAL PRODUCTS AND NEW PHOSPHOLIPID DERIVATIVES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1991009602A2 WO1991009602A2 (en) | 1991-07-11 |
| WO1991009602A3 true WO1991009602A3 (en) | 1992-12-10 |
Family
ID=6396421
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1990/002100 WO1991009602A2 (en) | 1989-12-23 | 1990-12-05 | Use of alkyl phospholipids as antiviral drugs, as well as new compounds |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0506704B1 (en) |
| AT (1) | ATE103177T1 (en) |
| AU (1) | AU8004291A (en) |
| DE (2) | DE3942933A1 (en) |
| WO (1) | WO1991009602A2 (en) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6599887B2 (en) | 1988-07-07 | 2003-07-29 | Chimerix, Inc. | Methods of treating viral infections using antiviral liponucleotides |
| US6252060B1 (en) | 1988-07-07 | 2001-06-26 | Nexstar Pharmaceuticals, Inc. | Antiviral liponucleosides: treatment of hepatitis B |
| US5817638A (en) * | 1988-07-07 | 1998-10-06 | Nexstar Pharmaceuticals, Inc. | Antiviral liponucleosides: treatment of hepatitis B |
| CA2001401A1 (en) * | 1988-10-25 | 1990-04-25 | Claude Piantadosi | Quaternary amine containing ether or ester lipid derivatives and therapeutic compositions |
| DE4222910A1 (en) * | 1992-07-11 | 1994-01-13 | Asta Medica Ag | New phospholipid derivatives |
| US6172050B1 (en) | 1992-07-11 | 2001-01-09 | Asta Medica Aktiengesellschaft | Phospholipid derivatives |
| DE4233044A1 (en) * | 1992-10-01 | 1994-04-07 | Asta Medica Ag | Phospholipid derivatives that contain higher elements of the 5th main group |
| US5958906A (en) * | 1992-10-01 | 1999-09-28 | Asta-Medica Aktiengesellschaft | Phospholipid derivatives containing higher elements of the fifth main group |
| DE69431596T4 (en) * | 1993-06-10 | 2003-10-30 | University Of North Carolina At Chapel Hill, Chapel Hill | (PHOSPHO) LIPIDS TO COMBAT HEPATITIS B INFECTION |
| DE4404085B4 (en) * | 1994-02-09 | 2006-09-21 | Rhône-Poulenc Rorer GmbH | Pharmaceutical and / or cosmetic composition |
| DE4416166C2 (en) * | 1994-05-06 | 1997-11-20 | Immuno Ag | Stable preparation for the treatment of blood clotting disorders |
| US6017891A (en) * | 1994-05-06 | 2000-01-25 | Baxter Aktiengesellschaft | Stable preparation for the treatment of blood coagulation disorders |
| US7135584B2 (en) | 1995-08-07 | 2006-11-14 | Wake Forest University | Lipid analogs for treating viral infections |
| DE69535758D1 (en) | 1994-08-29 | 2008-07-03 | Univ Wake Forest | LIPID ANALOGUE FOR THE TREATMENT OF VIRAL INFECTIONS |
| US7026469B2 (en) | 2000-10-19 | 2006-04-11 | Wake Forest University School Of Medicine | Compositions and methods of double-targeting virus infections and cancer cells |
| US7309696B2 (en) | 2000-10-19 | 2007-12-18 | Wake Forest University | Compositions and methods for targeting cancer cells |
| CN100469131C (en) | 2001-08-31 | 2009-03-11 | 汤姆森许可公司 | Sequence counter for an audio visual stream |
| JP2008538354A (en) | 2005-04-08 | 2008-10-23 | キメリクス，インコーポレイテッド | Compounds, compositions and methods for treating viral infections and other medical diseases |
| EP1800684A1 (en) * | 2005-12-20 | 2007-06-27 | Zentaris GmbH | Novel alkyl phospholipid derivatives and uses thereof |
| EP1962862B1 (en) * | 2005-12-19 | 2013-09-04 | Æterna Zentaris GmbH | Alkyl phospholipid derivatives with reduced cytotoxicity and uses therof |
| EP3085377A1 (en) | 2008-01-25 | 2016-10-26 | Chimerix, Inc. | Methods of treating viral infections |
| PT2534150T (en) | 2010-02-12 | 2017-05-02 | Chimerix Inc | Methods of treating viral infection |
| US9278135B2 (en) | 2010-04-26 | 2016-03-08 | Chimerix Inc. | Methods of treating retroviral infections and related dosage regimes |
| MX2022013280A (en) | 2020-04-30 | 2022-11-30 | Dow Global Technologies Llc | Ziegler-natta (pro)catalyst systems made with azaheterocyclic compound. |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0108565A2 (en) * | 1982-11-08 | 1984-05-16 | Takeda Chemical Industries, Ltd. | Phospholipids, their production and use thereof |
| WO1987001592A1 (en) * | 1985-09-17 | 1987-03-26 | Yeda Research And Development Company, Ltd. | Virus inactivation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62126108A (en) * | 1985-11-28 | 1987-06-08 | Pola Chem Ind Inc | External drug for skin |
-
1989
- 1989-12-23 DE DE3942933A patent/DE3942933A1/en not_active Withdrawn
-
1990
- 1990-12-05 WO PCT/EP1990/002100 patent/WO1991009602A2/en active IP Right Grant
- 1990-12-05 EP EP91900254A patent/EP0506704B1/en not_active Expired - Lifetime
- 1990-12-05 DE DE91900254T patent/DE59005139D1/en not_active Expired - Fee Related
- 1990-12-05 AU AU80042/91A patent/AU8004291A/en not_active Abandoned
- 1990-12-05 AT AT91900254T patent/ATE103177T1/en not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0108565A2 (en) * | 1982-11-08 | 1984-05-16 | Takeda Chemical Industries, Ltd. | Phospholipids, their production and use thereof |
| WO1987001592A1 (en) * | 1985-09-17 | 1987-03-26 | Yeda Research And Development Company, Ltd. | Virus inactivation |
Non-Patent Citations (3)
| Title |
|---|
| Microbios, Band 51, 1987, The Faculty Press, (Cambridge, GB), G. Menzel et al.: "Activity of alkyl phospholipids in virus-host systems", Seiten 15-21 * |
| Patent Abstracts of Japan, Band 11, Nr. 353 (C-457)(2800), 18. November 1987; & JP-A-62126108 (POLA CHEM. IND. INC.) 8 Juni 1987 * |
| Pharmazie, Band 41, Nr. 6, 1986, D. Sandow et al.: "Antivirale Wirkung von lysolecithin Analoga auf humanpathogene Viren", Seiten 404-406 * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU8004291A (en) | 1991-07-24 |
| DE3942933A1 (en) | 1991-06-27 |
| DE59005139D1 (en) | 1994-04-28 |
| WO1991009602A2 (en) | 1991-07-11 |
| EP0506704B1 (en) | 1994-03-23 |
| ATE103177T1 (en) | 1994-04-15 |
| EP0506704A1 (en) | 1992-10-07 |
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