CA1094455A - Tumor antidote - Google Patents
Tumor antidoteInfo
- Publication number
- CA1094455A CA1094455A CA277,458A CA277458A CA1094455A CA 1094455 A CA1094455 A CA 1094455A CA 277458 A CA277458 A CA 277458A CA 1094455 A CA1094455 A CA 1094455A
- Authority
- CA
- Canada
- Prior art keywords
- tumor
- formula
- antidote
- carbon atoms
- compound
- 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.)
- Expired
Links
- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 29
- 239000000729 antidote Substances 0.000 title claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- SUHOOTKUPISOBE-UHFFFAOYSA-N O-phosphoethanolamine Chemical compound NCCOP(O)(O)=O SUHOOTKUPISOBE-UHFFFAOYSA-N 0.000 claims 2
- NJNWCIAPVGRBHO-UHFFFAOYSA-N 2-hydroxyethyl-dimethyl-[(oxo-$l^{5}-phosphanylidyne)methyl]azanium Chemical class OCC[N+](C)(C)C#P=O NJNWCIAPVGRBHO-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical class CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 abstract description 4
- 229940075522 antidotes Drugs 0.000 abstract description 2
- 241001465754 Metazoa Species 0.000 description 12
- MHFRGQHAERHWKZ-HHHXNRCGSA-N (R)-edelfosine Chemical compound CCCCCCCCCCCCCCCCCCOC[C@@H](OC)COP([O-])(=O)OCC[N+](C)(C)C MHFRGQHAERHWKZ-HHHXNRCGSA-N 0.000 description 7
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 230000004083 survival effect Effects 0.000 description 4
- 210000004881 tumor cell Anatomy 0.000 description 4
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 238000010253 intravenous injection Methods 0.000 description 3
- 206010035226 Plasma cell myeloma Diseases 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- -1 lysolecithin com-pounds Chemical class 0.000 description 2
- 201000000050 myeloid neoplasm Diseases 0.000 description 2
- 230000004614 tumor growth Effects 0.000 description 2
- 206010003445 Ascites Diseases 0.000 description 1
- 238000011735 C3H mouse Methods 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 208000003468 Ehrlich Tumor Carcinoma Diseases 0.000 description 1
- PPQNQXQZIWHJRB-UHFFFAOYSA-N Methylcholanthrene Chemical compound C1=CC=C2C3=CC4=CC=C(C)C(CC5)=C4C5=C3C=CC2=C1 PPQNQXQZIWHJRB-UHFFFAOYSA-N 0.000 description 1
- 206010057249 Phagocytosis Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 210000003024 peritoneal macrophage Anatomy 0.000 description 1
- 230000008782 phagocytosis Effects 0.000 description 1
- YHHSONZFOIEMCP-UHFFFAOYSA-O phosphocholine Chemical compound C[N+](C)(C)CCOP(O)(O)=O YHHSONZFOIEMCP-UHFFFAOYSA-O 0.000 description 1
- 229950004354 phosphorylcholine Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 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
- C07F9/06—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2619686A DE2619686C2 (de) | 1976-05-04 | 1976-05-04 | Verwendung eines Lysolecithins zur Tumorbehandlung |
| DEP2619686.1 | 1976-05-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1094455A true CA1094455A (en) | 1981-01-27 |
Family
ID=5977045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA277,458A Expired CA1094455A (en) | 1976-05-04 | 1977-05-03 | Tumor antidote |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS52134027A (nl) |
| AU (1) | AU517586B2 (nl) |
| BE (1) | BE854270A (nl) |
| CA (1) | CA1094455A (nl) |
| DE (1) | DE2619686C2 (nl) |
| FR (1) | FR2364656A1 (nl) |
| GB (1) | GB1583661A (nl) |
| IE (1) | IE44927B1 (nl) |
| IL (1) | IL51988A (nl) |
| IT (1) | IT1071329B (nl) |
| LU (1) | LU77248A1 (nl) |
| NL (1) | NL189672C (nl) |
| NZ (1) | NZ183981A (nl) |
| SE (1) | SE7705071L (nl) |
| ZA (1) | ZA772649B (nl) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5396311A (en) * | 1977-01-29 | 1978-08-23 | Toyama Chem Co Ltd | Anti-cander drugs containing lysolecithins |
| JPS5528955A (en) * | 1978-08-24 | 1980-02-29 | Toyama Chem Co Ltd | Novel glycerophosphoric acid derivative, its salt, their preparation, and carcinostatic agent containing the same. |
| GB2046092B (en) * | 1979-03-05 | 1983-11-02 | Toyama Chemical Co Ltd | Pharmaceutical composition containing a lysophospholid and a phospholipid |
| US4408052A (en) * | 1980-02-27 | 1983-10-04 | Takeda Chemical Industries, Ltd. | Phospholipid carbamates |
| US4551532A (en) * | 1980-05-08 | 1985-11-05 | Takeda Chemical Industries, Ltd. | Ethylene glycol derivatives having anti-protozoan, anti-fungal and anti-tumor activity |
| EP0050327B1 (de) * | 1980-10-21 | 1984-06-20 | Roche Diagnostics GmbH | Neue schwefelhaltige Phospholipide, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| JPS5772914A (en) * | 1980-10-22 | 1982-05-07 | Takeda Chem Ind Ltd | Antitumor agent |
| EP0061872B1 (en) * | 1981-03-30 | 1985-08-07 | Takeda Chemical Industries, Ltd. | Ethyleneglycol derivatives, their production and use |
| DE3127503A1 (de) * | 1981-07-11 | 1983-02-17 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue phospholipide, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| DE3131524A1 (de) * | 1981-08-08 | 1983-02-24 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung physiologischer effektoren |
| US4562179A (en) * | 1982-04-19 | 1985-12-31 | Fujisawa Pharmaceutical Co., Ltd. | Phospholipid derivatives, and pharmaceutical composition of the same |
| DE3239817A1 (de) * | 1982-07-06 | 1984-01-12 | Max Planck Gesellschaft zur Förderung der Wissenschaften e.V., 3400 Göttingen | Neue glycerinderivate zur synthese von phospholipiden |
| DE3239858A1 (de) * | 1982-07-06 | 1984-01-12 | Max Planck Gesellschaft zur Förderung der Wissenschaften e.V., 3400 Göttingen | Neue d-mannitderivate als ausgangsprodukte zur synthese von phospholipiden |
| EP0103877B1 (en) * | 1982-09-21 | 1987-01-07 | Fujisawa Pharmaceutical Co., Ltd. | Phosphate derivatives, process for preparation thereof and pharmaceutical compositions of the same |
| US4710579A (en) * | 1984-11-09 | 1987-12-01 | Takeda Chemical Industries, Ltd. | 2-(acetoacetyloxy)-3-(octadecyloxy)propyl-3-trimethylammoniopropyl phosphate or a pharmaceutically acceptable salt thereof |
| US4761404A (en) * | 1985-07-01 | 1988-08-02 | Merck & Co., Inc. | Phospholipid analogs useful as PAF synthesis inhibitors |
| DE3662197D1 (en) | 1985-07-15 | 1989-04-06 | Takeda Chemical Industries Ltd | 2-alkanoyloxypropane derivatives, their production and use |
| JPS6294A (ja) * | 1986-05-09 | 1987-01-06 | Toyama Chem Co Ltd | 新規なグリセロリン酸誘導体およびその塩並びにそれらの製造法 |
| JP2561478B2 (ja) * | 1986-07-22 | 1996-12-11 | 武田薬品工業株式会社 | グリセリン誘導体 |
| US5036152A (en) * | 1988-03-10 | 1991-07-30 | Hoechst-Roussel Pharmaceuticals Incorporated | Alkoxycarbonylalkylphospholipids and alkylaminocarbonylalkylphospholipids |
| US4888328A (en) * | 1988-03-10 | 1989-12-19 | Hoeschst-Roussel Incorporated | Alkoxycarbonylalkylphospholipids and alkylaminocarbonylalkylphospholipids |
| 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 |
| DE3918082A1 (de) * | 1989-06-02 | 1991-01-24 | Max Planck Gesellschaft | Mittel gegen autoimmunerkrankungen |
| DE3935580C2 (de) * | 1989-10-25 | 1998-05-28 | Medmark Pharma Gmbh | Verwendung eines pharmazeutischen Wirkstoffes zur Behandlung von HIV-Infektionen |
| EP0581793A1 (en) * | 1991-04-25 | 1994-02-09 | University Of British Columbia | Phosphonates and phosphinates as anti-cancer, -inflammatory, -allergy and -myocarditis agents |
| ES2034885B1 (es) * | 1991-07-10 | 1994-03-01 | Menarini Lab | Procedimiento para la preparacion de cetoalquilglicerofosfolipidos. |
| KR100381449B1 (ko) * | 1994-10-14 | 2003-07-18 | 더 리포좀 컴퍼니, 인코퍼레이티드 | 에테르지질리포좀과이들의제약학적용도 |
| USRE39042E1 (en) * | 1996-02-16 | 2006-03-28 | The Liposome Company, Inc. | Etherlipid-containing multiple lipid liposomes |
| US5942246A (en) * | 1996-02-16 | 1999-08-24 | The Liposome Company, Inc. | Etherlipid containing multiple lipid liposomes |
| US6007839A (en) * | 1996-02-16 | 1999-12-28 | The Liposome Company, Inc. | Preparation of pharmaceutical compositions containing etherlipid-containing multiple lipid liposomes |
| US6667053B1 (en) | 1996-02-16 | 2003-12-23 | Elan Pharmaceuticals, Inc. | D and L etherlipid stereoisomers and liposomes |
| US5965159A (en) | 1996-02-16 | 1999-10-12 | The Liposome Company, Inc. | Etherlipid-containing multiple lipid liposomes |
| US6135426A (en) * | 1998-01-07 | 2000-10-24 | Briggs And Stratton Corporation | Priming system for internal combustion engines |
| EP2091520B1 (en) | 2006-11-10 | 2012-02-22 | Alphaptose Gmbh | Oral dosage form comprising tri-substituted glycerol compounds |
| CN101606061B (zh) * | 2006-11-10 | 2014-01-22 | 阿尔法普托斯有限公司 | 用于检测受体配体模拟物的方法和组合物 |
| US8637688B2 (en) * | 2006-12-20 | 2014-01-28 | Julia Diederichs | Topical dosage form comprising tri-substituted glycerol compounds |
| US20100136029A1 (en) * | 2006-12-20 | 2010-06-03 | Universitatsklinikum Hamburg-Eppendorf | Use of Tri-Substituted Glycerol Compounds for the Treatment of Hematological Malignancies |
| WO2013156630A1 (en) | 2012-04-20 | 2013-10-24 | Alphaptose Gmbh | S-enantiomer of a tri-substituted glycerol compound |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2009342C3 (de) * | 1970-02-27 | 1980-12-18 | Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften E.V., 3400 Goettingen | Verwendung von Glycerin-alkyläther-(l)-phosphorsäure-(3)-monocholinestern |
| DE2009343C3 (de) * | 1970-02-27 | 1980-10-23 | Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften E.V., 3400 Goettingen | Verwendung von Lysolecithinen als immunologische Adjuvantien |
| DE2009341C3 (de) * | 1970-02-27 | 1979-06-21 | Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften E.V., 3400 Goettingen | 3-Octadecyloxy-propanol-(l)-phosphorsäure-monocholinester und Verfahren zu dessen Herstellung |
| DE2033361C3 (de) * | 1970-07-06 | 1980-02-21 | Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften E.V., 3400 Goettingen | Acylpropandiol-(13)-phosphorsäurecholinester und Verfahren zu deren Herstellung |
-
1976
- 1976-05-04 DE DE2619686A patent/DE2619686C2/de not_active Expired
-
1977
- 1977-04-29 NL NLAANVRAGE7704723,A patent/NL189672C/nl not_active IP Right Cessation
- 1977-05-02 NZ NZ183981A patent/NZ183981A/xx unknown
- 1977-05-02 SE SE7705071A patent/SE7705071L/xx unknown
- 1977-05-02 IL IL51988A patent/IL51988A/xx unknown
- 1977-05-02 IT IT23094/77A patent/IT1071329B/it active
- 1977-05-03 IE IE888/77A patent/IE44927B1/en not_active IP Right Cessation
- 1977-05-03 ZA ZA00772649A patent/ZA772649B/xx unknown
- 1977-05-03 CA CA277,458A patent/CA1094455A/en not_active Expired
- 1977-05-03 GB GB18431/77A patent/GB1583661A/en not_active Expired
- 1977-05-03 AU AU24819/77A patent/AU517586B2/en not_active Expired
- 1977-05-03 LU LU77248A patent/LU77248A1/xx unknown
- 1977-05-04 FR FR7713522A patent/FR2364656A1/fr active Granted
- 1977-05-04 BE BE177280A patent/BE854270A/xx not_active IP Right Cessation
- 1977-05-04 JP JP5194477A patent/JPS52134027A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| LU77248A1 (nl) | 1977-12-13 |
| IL51988A (en) | 1981-05-20 |
| SE7705071L (sv) | 1977-11-05 |
| ZA772649B (en) | 1978-04-26 |
| JPS52134027A (en) | 1977-11-09 |
| DE2619686A1 (de) | 1977-11-24 |
| NZ183981A (en) | 1980-04-28 |
| IL51988A0 (en) | 1977-07-31 |
| DE2619686C2 (de) | 1986-08-07 |
| IE44927L (en) | 1977-11-04 |
| IE44927B1 (en) | 1982-05-19 |
| JPS6146455B2 (nl) | 1986-10-14 |
| IT1071329B (it) | 1985-04-02 |
| NL7704723A (nl) | 1977-11-08 |
| FR2364656A1 (fr) | 1978-04-14 |
| NL189672B (nl) | 1993-01-18 |
| NL189672C (nl) | 1993-06-16 |
| AU517586B2 (en) | 1981-08-13 |
| FR2364656B1 (nl) | 1980-03-07 |
| AU2481977A (en) | 1978-11-09 |
| GB1583661A (en) | 1981-01-28 |
| BE854270A (fr) | 1977-11-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |