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SI9300365B - New alkyl or alkene phosphates, a process for their preparation and their use as a medicament - Google Patents

New alkyl or alkene phosphates, a process for their preparation and their use as a medicament Download PDF

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SI9300365B
SI9300365B SI9300365A SI9300365A SI9300365B SI 9300365 B SI9300365 B SI 9300365B SI 9300365 A SI9300365 A SI 9300365A SI 9300365 A SI9300365 A SI 9300365A SI 9300365 B SI9300365 B SI 9300365B
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preparation
compounds according
phosphate
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general formula
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SI9300365A
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SI9300365A (en
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Gerhard Noessner
Bernhard Kutscher
Juergen Engel
Wolfgang Schumacher
Jurij Stekar
Peter Hilgard
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Zentaris Ag
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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    • 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
    • C07F9/106—Adducts, complexes, salts of phosphatides
    • A—HUMAN NECESSITIES
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    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
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    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
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    • A—HUMAN NECESSITIES
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    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/59—Hydrogenated pyridine rings

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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Novel phospholipid derivatives, preparation processes therefor and their use as medicaments are described.

Claims (16)

- 1 - PATENTNI ZAHTEVKI 1. Spojine s splošno formulo I O (CH2)m) R-Χ-Α-Ρ-Ο- (CH2)y-CH. O (CH2)n- 1 - Claims 1. Compounds of general formula I O (CH2) m) R-Χ-Α-Ρ-Ο- (CH2) y-CH. O (CH2) n R2 v kateri je R ravnoverižni ali razvejani alkilni ostanek z 10 do 24 ogljikovimi atomi, ki lahko vsebuje tudi eno do tri dvojne ali trojne vezi, R1 in R2 neodvisno drug od drugega vsebujeta vodik ali vsak en ravnoverižen, razvejan cikličen nasičen ali nenasičen alkilni ostanek z 1 do 6 ogljikovimi atomi, ki lahko vsebujeta tudi eno skupino CI-, OH-ali NH2- in pri čemer sta dva ta ostanka lahko tudi spojena v obroč, A je enostavna vez ali ena od skupin s formulami - CH2 - CH2 - CH2 - O - (II) - CH2 - CH2 - O - (III) -CH2-CH-0- (IV) -(CH2)8-0-(V) I ch3 -CH-CH-CH2-0- l \ h2c oR 2 in which R is a straight or branched alkyl residue of 10 to 24 carbon atoms, which may also contain one to three double or triple bonds, R 1 and R 2 independently of one another contain hydrogen or each single straight, branched cyclic saturated or unsaturated alkyl residue with 1 to 6 carbon atoms, which may also contain one group C1-, OH- or NH2- and where two of these residues may also be joined in a ring, A is a simple bond or one of the groups with formulas - CH2 - CH2 - CH2 - O - (II) - CH2 - CH2 - O - (III) -CH2-CH-O- (IV) - (CH2) 8-0- (V) I ch3 -CH-CH-CH2-0- 1 \ h2c o (VI) - 2- pri čemer so skupine (II) do (VI) orientirane tako, da je kisikov atom zvezan s fosforjevim atomom vezi (I) in je X kisikov aii žveplov atom ali NH, če je A enostavna vez ali pa kisikov ali žveplov atom, če je A ena od skupin (II) do (IV), kar pomeni, da je y enako 0 ali enemu naravnemu številu med 1 in 3, m in n sta neodvisno drug od drugega naravni števili, določeni z m + n = 2 do 8.(VI) - 2- wherein groups (II) to (VI) are oriented such that the oxygen atom is bonded to the phosphorus atom of the bond (I) and X is an oxygen or a sulfur atom or NH if A is a simple bond or oxygen or a sulfur atom, if A is one of groups (II) to (IV), which means that y is equal to 0 or one natural number between 1 and 3, m and n are independently natural numbers determined by zm + n = 2 to 8. 2. Spojine po zahtevku 1, označene s tem, da X pomeni kisikov atom.Compounds according to Claim 1, characterized in that X represents an oxygen atom. 3. Spojine po zahtevkih 1 ali 2, označene s tem, da A pomeni enostavno vez.Compounds according to Claims 1 or 2, characterized in that A represents a simple bond. 4. Spojine po zahtevkih 1 do 3, označene s tem, da sta R1 in R2 vsakokrat metilni skupini. - 3 -Compounds according to Claims 1 to 3, characterized in that R 1 and R 2 are in each case methyl groups. - 3 - 5. Oktadecil - (1,1-dimetilpiperidin - 4- il) - fosfat, oktadecil - (1,1-dimetilheksahidroazepino - 4- il) - fosfat.5. Octadecyl - (1,1-dimethylpiperidin-4-yl) -phosphate, octadecyl- (1,1-dimethylhexahydroazepino-4-yl) -phosphate. 6. Postopek za pripravo spojine po enem od zahtevkov 1 do 5, označen s tem, da se doseže, da spojina splošne formule R-X-A-H (VII) v kateri imajo R, X in A v. zahtevku 1.navedene pomene, reagira s fosforoksitrikloridom v navzočnosti primerne pomožne baze za reakcijo z ali brez topila in se nato s spojino splošne formule HO - (CH2)y - CHProcess for the preparation of a compound according to one of Claims 1 to 5, characterized in that it is achieved that the compound of the general formula R-X-A-H (VII) in which R, X and A have v. claim 1, said reaction with phosphoroxytrichloride in the presence of a suitable auxiliary base for reaction with or without a solvent and then with a compound of general formula HO - (CH2) y - CH (CH2 )m(CH2) m (CH2 )n(CH2) n y- (Vlil) v kateri imajo R1 in R2, y, m in n pomene, navedene v zahtevku 1 in y-pomeni halogenid, mesilat ali tosilat pretvori v spojino s splošno formulo I, na primer so lahko spojine s splošno formulo (CH2) HO - (CH2)y - CH (CH2)ny- (V1yl) in which R1 and R2, y, m and n have the meanings given in claim 1 and y-means convert the halide, mesylate or tosylate to a compound of general formula I, for example compounds of general formula (CH2) ) HO - (CH2) y - CH (CH2) n N- R (IX) - 4 - v kateri imajo R1, y, m in n pomene, navedene v zahtevku 1, pretvorjene, pri čemer se spojine s splošno formulo (I), pri katerih sta R1 in/ali R2 vodika, z alkilirnimi sredstvi R2-Y, pri katerih ima R2 pomen, naveden v zahtevku 1 in je Y Cl, brom, jod, tosil ali mesil, pretvorijo na svoj poznani način.N- R (IX) - 4 - in which R1, y, m and n have the meanings given in claim 1, converted, the compounds of general formula (I) in which R1 and / or R2 are hydrogen, with alkylating agents R2-Y, in which R2 has the meaning given in claim 1 and Y is Cl, bromine, iodine, tosyl or mesyl, are converted in their known manner. 7. Postopek čiščenja spojin s formulo I, označen s tem, da se raztopina spojine, primerna formuli I, oziroma pripravljena po poznanemu postopku oziroma primerno postopku, primernemu zahtevku 5, obdela v organskem topilu z ionskim izmenjevalcem v mešalnem sloju oziroma eden za drugim ali istočasno s kislim ali bazičnim ionskim izmenjevalcem.Process for the purification of compounds of formula I, characterized in that the solution of the compound suitable for formula I, or prepared according to a known method or a suitable process according to claim 5, is treated in an organic solvent with an ion exchanger in the mixing layer or one after the other. simultaneously with an acidic or basic ion exchanger. 8. Zdravilno sredstvo, označeno s tem, da kot aktivno substanco vsebuje eno ali več spojin po enem od zahtevkov 1 do 5 oziroma farmacevtsko primerno sol iz ene od njih, na primer skupaj s farmacevtsko običajnimi nosilnimi, pomagalnimi, polnilnimi in razredčilnimi sredstvi, pri čemer je količina aktivne substance med 50 mg in 250 mg. ' 5 -Medicament, characterized in that it contains as active substance one or more compounds according to one of Claims 1 to 5, or a pharmaceutically acceptable salt thereof, for example together with pharmaceutically customary carriers, excipients, fillers and diluents, in wherein the amount of active substance is between 50 mg and 250 mg. '5 - 9. Zdravilno sredstvo po zahtevku 7, označeno s tem, da kot aktivno sredstvo vsebuje oktadecil-(1,1 -dimetilpiperidin-4-il)-fosfat, oktadecil-(1,1-dimetilhidroazepino-4-il)-fosfat, erucil-(1,1-dimetilpiperidin-4-il)-fosfat ali erucil-(1,1 -dimetilperhidroazepinio-4-il) fosfat, pri čemer je količina aktivnega sredstva med 50 mg in 250 mg.Medicament according to Claim 7, characterized in that it contains as active agent octadecyl- (1,1-dimethylpiperidin-4-yl) -phosphate, octadecyl- (1,1-dimethylhydroazepino-4-yl) -phosphate, erucil - (1,1-dimethylpiperidin-4-yl) -phosphate or erucyl- (1,1-dimethylperhydroazepinio-4-yl) phosphate, the amount of active agent being between 50 mg and 250 mg. 10. Zdravilno sredstvo po zahtevku 8, označeno s tem, da kot aktivno substanco vsebuje oktadecil-(1.1 -dimetilpiperidin-4-il) fosfat, pri čemer je količina aktivnega sredstva med 50 mg in 250 mg.Medicament according to Claim 8, characterized in that it contains octadecyl- (1,1-dimethylpiperidin-4-yl) phosphate as active substance, the amount of active agent being between 50 mg and 250 mg. 11. Uporaba spojin po zahtevkih od 1 do 5 za pripravo zdravil za zatiranje tumorjev.Use of compounds according to claims 1 to 5 for the preparation of medicaments for the suppression of tumors. 12. Uporaba spojin po zahtevkih od 1 do 5 za pripravo zdravil za zatiranje protozojskih in glivičnih obolenj, zlasti leishmaniazeUse of compounds according to claims 1 to 5 for the preparation of medicaments for the control of protozoal and fungal diseases, in particular leishmaniasis 13. Uporaba spojin po zahtevkih od 1 do 5 za pripravo zdravil za terapijo avtoimunskih bolezni, zlasti multiple skleroze. 6-Use of compounds according to claims 1 to 5 for the preparation of medicaments for the therapy of autoimmune diseases, in particular multiple sclerosis. 6- 14. Uporaba spojin po zahtevkih od 1 do 5 za pripravo zdravil za terapijo kožnih obolenj, zlasti psoriaze.Use of compounds according to claims 1 to 5 for the preparation of medicaments for the treatment of skin diseases, in particular psoriasis. 15. Uporaba spojin po zahtevkih od 1 do 5 za pripravo zdravil za terapijo poškodb kostnega mozga zaradi zdravljenja s citostatiki in drugimi učinkovinami, škodljivimi za kostni mozeg.Use of compounds according to claims 1 to 5 for the preparation of medicaments for the treatment of bone marrow injuries due to treatment with cytostatics and other active substances harmful to the bone marrow. 16. Postopek za pripravo antitumorskega sredstva, označen s tem, da pripravimo formulacijo, ki kot učinkovino vsebuje eno ali več spojin po enem od zahtevkov 1 do 5, po izibiri skupaj s farmacevtsko običajnimi nosilnimi, pomožnimi, polnilnimi in razredčilnimi sredstvi.Process for the preparation of an antitumor agent, characterized in that a formulation containing as active ingredient one or more compounds according to one of Claims 1 to 5 is prepared, optionally together with pharmaceutically conventional carrier, auxiliary, filling and diluent agents.
SI9300365A 1992-07-11 1993-07-09 New alkyl or alkene phosphates, a process for their preparation and their use as a medicament SI9300365B (en)

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DE4222910A DE4222910A1 (en) 1992-07-11 1992-07-11 New phospholipid derivatives

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JP5475234B2 (en) 2005-01-21 2014-04-16 アステックス・セラピューティクス・リミテッド Pharmaceutical compounds
EP1800684A1 (en) * 2005-12-20 2007-06-27 Zentaris GmbH Novel alkyl phospholipid derivatives and uses thereof
PL1962862T3 (en) 2005-12-19 2014-01-31 Aeterna Zentaris Gmbh Alkyl phospholipid derivatives with reduced cytotoxicity and uses therof
EP1869981A1 (en) * 2006-06-21 2007-12-26 Staatliches Weinbauinstitut Freiburg Alkylphospholipids and lysophospholipids for controlling plant pathogens
US8883790B2 (en) 2006-10-12 2014-11-11 Astex Therapeutics Limited Pharmaceutical combinations
WO2008044041A1 (en) 2006-10-12 2008-04-17 Astex Therapeutics Limited Pharmaceutical combinations

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LTIP620A (en) 1994-07-15
HRP931046B1 (en) 2000-06-30
NO932502L (en) 1994-01-12
YU49079B (en) 2003-08-29
YU47393A (en) 1997-08-22
HU218783B (en) 2000-12-28
DK0579939T3 (en) 1999-09-20
UA40567C2 (en) 2001-08-15
CA2511753C (en) 2007-09-25
NO932502D0 (en) 1993-07-08
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SK67093A3 (en) 1995-03-08
CA2100228C (en) 2006-01-24
AU664101B2 (en) 1995-11-02
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PL299624A1 (en) 1994-02-21
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HUT64548A (en) 1994-01-28
HRP931046A2 (en) 1997-04-30
SG46249A1 (en) 1998-02-20
ES2129053T3 (en) 1999-06-01
RU2108336C1 (en) 1998-04-10
HU9301992D0 (en) 1993-09-28
IL106289A0 (en) 1994-04-12
JP3311431B2 (en) 2002-08-05
PL173388B1 (en) 1998-02-27
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FI933165A0 (en) 1993-07-09
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EE03140B1 (en) 1998-12-15
GR3029602T3 (en) 1999-06-30
PL175607B1 (en) 1999-01-29
MX9304133A (en) 1994-04-29
BR9302809A (en) 1994-03-15
DE59309355D1 (en) 1999-03-18
SI9300365A (en) 1994-03-31
AU4186493A (en) 1994-01-13
LV10870B (en) 1996-06-20
LT3113B (en) 1994-12-27
SK283827B6 (en) 2004-02-03
EP0579939B1 (en) 1999-02-03
CN1039012C (en) 1998-07-08
CA2511753A1 (en) 1994-01-12
ZA934971B (en) 1994-02-01
LV10870A (en) 1995-10-20
CZ124993A3 (en) 1995-03-15
CA2100228A1 (en) 1994-01-12
KR940002265A (en) 1994-02-17
EP0579939A1 (en) 1994-01-26
FI933165A7 (en) 1994-01-12
IL106289A (en) 2000-06-01
KR100297180B1 (en) 2001-11-30
NO306468B1 (en) 1999-11-08
DE4222910A1 (en) 1994-01-13
JPH0733791A (en) 1995-02-03

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