SI9300365B - Novi alkilni ali alkenski fosfati, postopek za njihovo pripravo in njihova uporaba kot zdravilnega sredstva - Google Patents
Novi alkilni ali alkenski fosfati, postopek za njihovo pripravo in njihova uporaba kot zdravilnega sredstva Download PDFInfo
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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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- compounds according
- phosphate
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- 239000003814 drug Substances 0.000 title claims abstract 10
- 238000002360 preparation method Methods 0.000 title claims abstract 9
- 238000000034 method Methods 0.000 title claims 6
- 150000001337 aliphatic alkines Chemical class 0.000 title 1
- 150000001336 alkenes Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 19
- 239000013543 active substance Substances 0.000 claims 7
- 229910019142 PO4 Inorganic materials 0.000 claims 6
- 239000010452 phosphate Substances 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 210000001185 bone marrow Anatomy 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 150000002500 ions Chemical class 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 208000004554 Leishmaniasis Diseases 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 208000031888 Mycoses Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 239000012050 conventional carrier Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000000824 cytostatic agent Substances 0.000 claims 1
- 230000001085 cytostatic effect Effects 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 125000004437 phosphorous atom Chemical group 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims 1
- 150000003904 phospholipids Chemical class 0.000 abstract 1
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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- 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
- C07F9/106—Adducts, complexes, salts of phosphatides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- 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
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
- C07F9/547—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
- C07F9/5532—Seven-(or more) membered rings
-
- 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
- C07F9/547—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
- C07F9/572—Five-membered rings
-
- 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
- C07F9/547—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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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Physical Education & Sports Medicine (AREA)
- Tropical Medicine & Parasitology (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- AIDS & HIV (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
Claims (16)
- - 1 - PATENTNI ZAHTEVKI 1. Spojine s splošno formulo I O (CH2)m) R-Χ-Α-Ρ-Ο- (CH2)y-CH. O (CH2)nR2 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 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.
- 2. Spojine po zahtevku 1, označene s tem, da X pomeni kisikov atom.
- 3. Spojine po zahtevkih 1 ali 2, označene s tem, da A pomeni enostavno vez.
- 4. Spojine po zahtevkih 1 do 3, označene s tem, da sta R1 in R2 vsakokrat metilni skupini. - 3 -
- 5. Oktadecil - (1,1-dimetilpiperidin - 4- il) - fosfat, oktadecil - (1,1-dimetilheksahidroazepino - 4- il) - fosfat.
- 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 - CH(CH2 )m(CH2 )ny- (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)nN- 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.
- 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.
- 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 -
- 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.
- 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.
- 11. Uporaba spojin po zahtevkih od 1 do 5 za pripravo zdravil za zatiranje tumorjev.
- 12. Uporaba spojin po zahtevkih od 1 do 5 za pripravo zdravil za zatiranje protozojskih in glivičnih obolenj, zlasti leishmaniaze
- 13. Uporaba spojin po zahtevkih od 1 do 5 za pripravo zdravil za terapijo avtoimunskih bolezni, zlasti multiple skleroze. 6-
- 14. Uporaba spojin po zahtevkih od 1 do 5 za pripravo zdravil za terapijo kožnih obolenj, zlasti psoriaze.
- 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.
- 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.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4222910A DE4222910A1 (de) | 1992-07-11 | 1992-07-11 | Neue Phospholipidderivate |
Publications (2)
Publication Number | Publication Date |
---|---|
SI9300365A SI9300365A (en) | 1994-03-31 |
SI9300365B true SI9300365B (sl) | 2002-02-28 |
Family
ID=6463031
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SI9300365A SI9300365B (sl) | 1992-07-11 | 1993-07-09 | Novi alkilni ali alkenski fosfati, postopek za njihovo pripravo in njihova uporaba kot zdravilnega sredstva |
Country Status (31)
Country | Link |
---|---|
EP (1) | EP0579939B1 (sl) |
JP (1) | JP3311431B2 (sl) |
KR (1) | KR100297180B1 (sl) |
CN (1) | CN1039012C (sl) |
AT (1) | ATE176477T1 (sl) |
AU (1) | AU664101B2 (sl) |
BR (1) | BR9302809A (sl) |
CA (2) | CA2511753C (sl) |
CZ (1) | CZ290863B6 (sl) |
DE (2) | DE4222910A1 (sl) |
DK (1) | DK0579939T3 (sl) |
EE (1) | EE03140B1 (sl) |
ES (1) | ES2129053T3 (sl) |
FI (1) | FI111262B (sl) |
GR (1) | GR3029602T3 (sl) |
HR (1) | HRP931046B1 (sl) |
HU (1) | HU218783B (sl) |
IL (1) | IL106289A (sl) |
LT (1) | LT3113B (sl) |
LV (1) | LV10870B (sl) |
MX (1) | MX9304133A (sl) |
NO (1) | NO306468B1 (sl) |
PL (3) | PL175607B1 (sl) |
RU (1) | RU2108336C1 (sl) |
SG (1) | SG46249A1 (sl) |
SI (1) | SI9300365B (sl) |
SK (1) | SK283827B6 (sl) |
TW (1) | TW304956B (sl) |
UA (1) | UA40567C2 (sl) |
YU (1) | YU49079B (sl) |
ZA (1) | ZA934971B (sl) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2006207321B2 (en) | 2005-01-21 | 2012-09-06 | Astex Therapeutics Limited | Pharmaceutical compounds |
EP1800684A1 (en) * | 2005-12-20 | 2007-06-27 | Zentaris GmbH | Novel alkyl phospholipid derivatives and uses thereof |
WO2007071658A2 (en) * | 2005-12-19 | 2007-06-28 | Æterna Zentaris Gmbh | Alkyl phospholipid derivatives with reduced cytotoxicity and uses thereof |
EP1869981A1 (de) * | 2006-06-21 | 2007-12-26 | Staatliches Weinbauinstitut Freiburg | Alkylphospholipide und Lyso-Phospholipide zur Bekämpfung von Pflanzenpathogenen |
JP5528807B2 (ja) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | 複合薬剤 |
JP5528806B2 (ja) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | 複合薬剤 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0050327B1 (de) * | 1980-10-21 | 1984-06-20 | Roche Diagnostics GmbH | Neue schwefelhaltige Phospholipide, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
JPS5984824A (ja) * | 1982-11-08 | 1984-05-16 | Takeda Chem Ind Ltd | 抗腫瘍剤 |
DE3530767A1 (de) * | 1985-08-28 | 1987-03-12 | Max Planck Gesellschaft | Mittel gegen multiple sklerose |
IE59777B1 (en) * | 1985-12-04 | 1994-04-06 | Max Planck Gesellschaft | Medicaments |
JP2512311B2 (ja) * | 1986-07-14 | 1996-07-03 | 日本ケミファ株式会社 | 新規なグリセリン誘導体及び血圧降下剤 |
DE3881925T2 (de) * | 1987-03-24 | 1994-01-27 | Nippon Chemiphar Co | Glycerol-Derivate und anti-hypertensives Mittel. |
DE3906952A1 (de) * | 1989-03-04 | 1990-09-06 | Boehringer Mannheim Gmbh | (3-(c(pfeil abwaerts)1(pfeil abwaerts)(pfeil abwaerts)6(pfeil abwaerts)-c(pfeil abwaerts)1(pfeil abwaerts)(pfeil abwaerts)8(pfeil abwaerts))alkansulfinyl- und sulfonyl-2-methoxymethyl-propyl)-(2-trimethylammonio-ethyl) phosphate, verfahren zu deren herstellung diese verbindungen enthaltende arzneimittel |
DE3942933A1 (de) * | 1989-12-23 | 1991-06-27 | Boehringer Mannheim Gmbh | Verwendung von alkylphospholipiden als antivirale arzneimittel und neue phospholipid-derivate |
DE4114586A1 (de) * | 1991-05-04 | 1992-11-05 | Boehringer Mannheim Gmbh | Arzneimittel enthaltend azacyclodiphosphonsaeurederivate, neue azacyclodiphosphonsaeurederivate sowie verfahren zu deren herstellung |
-
1992
- 1992-07-11 DE DE4222910A patent/DE4222910A1/de not_active Ceased
-
1993
- 1993-06-01 TW TW082104345A patent/TW304956B/zh not_active IP Right Cessation
- 1993-06-03 DE DE59309355T patent/DE59309355D1/de not_active Expired - Lifetime
- 1993-06-03 ES ES93108904T patent/ES2129053T3/es not_active Expired - Lifetime
- 1993-06-03 AT AT93108904T patent/ATE176477T1/de active
- 1993-06-03 DK DK93108904T patent/DK0579939T3/da active
- 1993-06-03 EP EP93108904A patent/EP0579939B1/de not_active Expired - Lifetime
- 1993-06-03 SG SG1996001626A patent/SG46249A1/en unknown
- 1993-06-04 LT LTIP620A patent/LT3113B/lt not_active IP Right Cessation
- 1993-06-23 CZ CZ19931249A patent/CZ290863B6/cs not_active IP Right Cessation
- 1993-06-28 SK SK670-93A patent/SK283827B6/sk not_active IP Right Cessation
- 1993-07-06 YU YU47393A patent/YU49079B/sh unknown
- 1993-07-08 PL PL93318680A patent/PL175607B1/pl unknown
- 1993-07-08 PL PL93318679A patent/PL177811B1/pl unknown
- 1993-07-08 NO NO932502A patent/NO306468B1/no not_active IP Right Cessation
- 1993-07-08 PL PL93299624A patent/PL173388B1/pl unknown
- 1993-07-08 JP JP16911493A patent/JP3311431B2/ja not_active Expired - Lifetime
- 1993-07-09 IL IL10628993A patent/IL106289A/xx not_active IP Right Cessation
- 1993-07-09 HR HR931046A patent/HRP931046B1/xx not_active IP Right Cessation
- 1993-07-09 RU RU93047049A patent/RU2108336C1/ru active
- 1993-07-09 CA CA002511753A patent/CA2511753C/en not_active Expired - Lifetime
- 1993-07-09 SI SI9300365A patent/SI9300365B/sl unknown
- 1993-07-09 ZA ZA934971A patent/ZA934971B/xx unknown
- 1993-07-09 MX MX9304133A patent/MX9304133A/es active IP Right Grant
- 1993-07-09 UA UA93002052A patent/UA40567C2/uk unknown
- 1993-07-09 BR BR9302809A patent/BR9302809A/pt not_active Application Discontinuation
- 1993-07-09 AU AU41864/93A patent/AU664101B2/en not_active Expired
- 1993-07-09 CA CA002100228A patent/CA2100228C/en not_active Expired - Lifetime
- 1993-07-09 HU HU9301992A patent/HU218783B/hu unknown
- 1993-07-09 FI FI933165A patent/FI111262B/fi not_active IP Right Cessation
- 1993-07-10 KR KR1019930012980A patent/KR100297180B1/ko not_active IP Right Cessation
- 1993-07-10 CN CN93108564A patent/CN1039012C/zh not_active Expired - Lifetime
- 1993-07-12 LV LVP-93-988A patent/LV10870B/lv unknown
-
1994
- 1994-10-25 EE EE9400199A patent/EE03140B1/xx unknown
-
1999
- 1999-03-08 GR GR990400689T patent/GR3029602T3/el unknown
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