RU98113304A - NEW PHOSPHOLIPID DERIVATIVES OF PHOSPHONOCARBOXYLIC ACIDS, THEIR PRODUCTION AND APPLICATION AS ANTI-VIRUS MEDICINES - Google Patents
NEW PHOSPHOLIPID DERIVATIVES OF PHOSPHONOCARBOXYLIC ACIDS, THEIR PRODUCTION AND APPLICATION AS ANTI-VIRUS MEDICINESInfo
- Publication number
- RU98113304A RU98113304A RU98113304/04A RU98113304A RU98113304A RU 98113304 A RU98113304 A RU 98113304A RU 98113304/04 A RU98113304/04 A RU 98113304/04A RU 98113304 A RU98113304 A RU 98113304A RU 98113304 A RU98113304 A RU 98113304A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- compounds
- butyl
- denotes
- benzyl
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims 3
- 239000002253 acid Substances 0.000 title 1
- 150000007513 acids Chemical class 0.000 title 1
- 230000002155 anti-virotic effect Effects 0.000 title 1
- 150000003904 phospholipids Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 229960004203 carnitine Drugs 0.000 claims 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims 1
- 229960001231 choline Drugs 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229940031098 ethanolamine Drugs 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- -1 phospholipid derivatives of phosphonocarboxylic acids Chemical class 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 230000001177 retroviral effect Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
Claims (8)
в которой R1 обозначает линейную или разветвленную, насыщенную или ненасыщенную алкильную цепь с 9-13 атомами углерода;
R2 обозначает линейную или разветвленную, насыщенную или ненасыщенную алкильную цепь с 8-12 атомами углepoдa;
R3 обозначает Н, линейную или разветвленную алкильную цепь с 1-6 атомами углерода, в частности, метил, этил, пропил, изопропил, бутил, изобутил, трет-бутил, пентил, гексил, неопентил, тексил или фенил, холин, этаноламин, карнитин, С5-С7-циклоалкил, бензил или одну из следующих групп
причем R4 обозначает алкил, бензил или фенил и R5, и R6 обозначают алкил и п равно 1, 2 или 3;
n равно 0, 1 или 2;
m равно 0, соответственно 1-3;
их таутомеры, оптические изомеры, рацематы, их пролекарства и их физиологически приемлемые соли неорганических и органических оснований.1. New phospholipid derivatives of phosphonocarboxylic acids of General formula I
in which R 1 denotes a linear or branched, saturated or unsaturated alkyl chain with 9-13 carbon atoms;
R 2 is a linear or branched, saturated or unsaturated alkyl chain with 8-12 carbon atoms;
R 3 is H, a linear or branched alkyl chain with 1-6 carbon atoms, in particular methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, neopentyl, texyl or phenyl, choline, ethanolamine, carnitine, C 5 -C 7 cycloalkyl, benzyl or one of the following groups
wherein R 4 is alkyl, benzyl or phenyl and R 5 and R 6 are alkyl and n is 1, 2 or 3;
n is 0, 1 or 2;
m is 0, respectively 1-3;
their tautomers, optical isomers, racemates, their prodrugs and their physiologically acceptable salts of inorganic and organic bases.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19547023.0 | 1995-12-15 | ||
| DE1995147023 DE19547023A1 (en) | 1995-12-15 | 1995-12-15 | New phosphatidyl alkanoic acid derivatives |
| DE19643416.5 | 1996-10-22 | ||
| DE1996143416 DE19643416A1 (en) | 1996-10-22 | 1996-10-22 | New phospho:lipid derived from phosphono-carboxylate and thio-glycerol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU98113304A true RU98113304A (en) | 2000-04-27 |
| RU2166508C2 RU2166508C2 (en) | 2001-05-10 |
Family
ID=26021319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU98113304/04A RU2166508C2 (en) | 1995-12-15 | 1996-12-16 | Phosphonolipids of carboxylic acids and salts thereof, and antiviral agent based thereon |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US6136797A (en) |
| EP (1) | EP0868425B1 (en) |
| JP (1) | JP2000515113A (en) |
| KR (1) | KR20000064374A (en) |
| CN (1) | CN1085672C (en) |
| AR (1) | AR005089A1 (en) |
| AT (1) | ATE278698T1 (en) |
| AU (1) | AU714236B2 (en) |
| BR (1) | BR9612133A (en) |
| CA (1) | CA2240366A1 (en) |
| CZ (1) | CZ291823B6 (en) |
| DE (1) | DE59611111D1 (en) |
| ES (1) | ES2230574T3 (en) |
| HU (1) | HUP0001534A3 (en) |
| IL (1) | IL124790A (en) |
| NO (1) | NO982754L (en) |
| NZ (1) | NZ325259A (en) |
| PL (1) | PL186402B1 (en) |
| RU (1) | RU2166508C2 (en) |
| SK (1) | SK75698A3 (en) |
| TR (1) | TR199801082T2 (en) |
| TW (1) | TW343975B (en) |
| WO (1) | WO1997022613A1 (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19547022A1 (en) * | 1995-12-15 | 1997-06-19 | Boehringer Mannheim Gmbh | Covalent lipid-phosphonocarboxylic acid conjugates, their preparation and their use as antiviral drugs |
| US7915238B2 (en) * | 1999-02-01 | 2011-03-29 | Eisai R & D Management Co., Ltd. | Immunomodulatory compounds and methods of use thereof |
| US20040006242A1 (en) | 1999-02-01 | 2004-01-08 | Hawkins Lynn D. | Immunomodulatory compounds and method of use thereof |
| US6835721B2 (en) | 1999-02-01 | 2004-12-28 | Eisai Co., Ltd. | Immunomodulatory compounds and methods of use thereof |
| US6551600B2 (en) * | 1999-02-01 | 2003-04-22 | Eisai Co., Ltd. | Immunological adjuvant compounds compositions and methods of use thereof |
| US6818057B2 (en) | 1999-03-02 | 2004-11-16 | Construction Research & Technology Gmbh | Retarder for calcium sulfoaluminate cements |
| RU2265439C2 (en) * | 2000-01-04 | 2005-12-10 | Де Риджентс Ов Де Юниверсити Ов Калифорния | Treatment of hiv infection at medicinal resistance |
| RU2240792C2 (en) * | 2002-07-30 | 2004-11-27 | Государственное учреждение Научно-исследовательский институт вирусологии им. Д.И. Ивановского РАМН | Combinations based on netropsin or its bis-derivative eliciting anti-herpetic activity |
| US20040172288A1 (en) * | 2003-02-27 | 2004-09-02 | Korn Lawrence D. | Method for disseminating medical alert information |
| WO2006116423A2 (en) | 2005-04-26 | 2006-11-02 | Eisai Co., Ltd | Compositions and methods for cancer immunotherapy |
| US20070292418A1 (en) * | 2005-04-26 | 2007-12-20 | Eisai Co., Ltd. | Compositions and methods for immunotherapy |
| JP5752599B2 (en) * | 2008-11-06 | 2015-07-22 | ヴァスキュラー バイオジェニックス リミテッド | Oxidized lipid compounds and uses thereof |
| EP2876094A1 (en) | 2014-04-03 | 2015-05-27 | Basf Se | Cement and calcium sulphate based binder composition |
| KR101658048B1 (en) | 2014-06-25 | 2016-09-20 | 한국생명공학연구원 | Anti-viral composition comprising compounds related to phosphatidylcholine synthetic pathway |
| EP3813839A4 (en) * | 2018-06-26 | 2022-07-20 | TSRL, Inc. | METABOLICLY STABLE PRODRUGS |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3164332D1 (en) * | 1980-10-21 | 1984-07-26 | Boehringer Mannheim Gmbh | Phospholipids that contain sulphur, process for their preparation and medicines containing these compounds |
| US5194654A (en) * | 1989-11-22 | 1993-03-16 | Vical, Inc. | Lipid derivatives of phosphonoacids for liposomal incorporation and method of use |
| DE3929217A1 (en) * | 1989-09-02 | 1991-03-07 | Boehringer Mannheim Gmbh | USE OF PHOSPHOLIPID DERIVATIVES AS ANTIVIRAL MEDICINAL PRODUCTS AND NEW PHOSPHOLIPIDES |
| DE4026265A1 (en) * | 1990-08-20 | 1992-02-27 | Boehringer Mannheim Gmbh | NEW PHOSPHOLIPID DERIVATIVES OF NUCLEOSIDES, THEIR PRODUCTION AND THEIR USE AS ANTIVIRAL MEDICINAL PRODUCTS |
| US5696277A (en) * | 1994-11-15 | 1997-12-09 | Karl Y. Hostetler | Antiviral prodrugs |
| DE19547022A1 (en) * | 1995-12-15 | 1997-06-19 | Boehringer Mannheim Gmbh | Covalent lipid-phosphonocarboxylic acid conjugates, their preparation and their use as antiviral drugs |
-
1996
- 1996-12-14 TW TW085115475A patent/TW343975B/en active
- 1996-12-16 AR ARP960105701A patent/AR005089A1/en not_active Application Discontinuation
- 1996-12-16 TR TR1998/01082T patent/TR199801082T2/en unknown
- 1996-12-16 WO PCT/EP1996/005647 patent/WO1997022613A1/en not_active Ceased
- 1996-12-16 BR BR9612133A patent/BR9612133A/en not_active IP Right Cessation
- 1996-12-16 US US09/077,891 patent/US6136797A/en not_active Expired - Fee Related
- 1996-12-16 CZ CZ19981810A patent/CZ291823B6/en not_active IP Right Cessation
- 1996-12-16 KR KR1019980704352A patent/KR20000064374A/en not_active Ceased
- 1996-12-16 EP EP96943972A patent/EP0868425B1/en not_active Expired - Lifetime
- 1996-12-16 IL IL12479096A patent/IL124790A/en not_active IP Right Cessation
- 1996-12-16 SK SK756-98A patent/SK75698A3/en unknown
- 1996-12-16 CN CN96180011A patent/CN1085672C/en not_active Expired - Fee Related
- 1996-12-16 ES ES96943972T patent/ES2230574T3/en not_active Expired - Lifetime
- 1996-12-16 DE DE59611111T patent/DE59611111D1/en not_active Expired - Fee Related
- 1996-12-16 CA CA002240366A patent/CA2240366A1/en not_active Abandoned
- 1996-12-16 NZ NZ325259A patent/NZ325259A/en unknown
- 1996-12-16 HU HU0001534A patent/HUP0001534A3/en unknown
- 1996-12-16 PL PL96327173A patent/PL186402B1/en not_active IP Right Cessation
- 1996-12-16 RU RU98113304/04A patent/RU2166508C2/en not_active IP Right Cessation
- 1996-12-16 AT AT96943972T patent/ATE278698T1/en not_active IP Right Cessation
- 1996-12-16 AU AU13730/97A patent/AU714236B2/en not_active Ceased
- 1996-12-16 JP JP09522501A patent/JP2000515113A/en not_active Ceased
-
1998
- 1998-06-15 NO NO982754A patent/NO982754L/en not_active Application Discontinuation
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