LU87860A1 - Derives du glycerol,un procede de preparation de ces derives et des compositions therapeutiques les contenant - Google Patents
Derives du glycerol,un procede de preparation de ces derives et des compositions therapeutiques les contenant Download PDFInfo
- Publication number
- LU87860A1 LU87860A1 LU87860A LU87860A LU87860A1 LU 87860 A1 LU87860 A1 LU 87860A1 LU 87860 A LU87860 A LU 87860A LU 87860 A LU87860 A LU 87860A LU 87860 A1 LU87860 A1 LU 87860A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- compound
- methyl
- methoxy
- carbon atoms
- octadecylamino
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 19
- 230000001225 therapeutic effect Effects 0.000 title claims description 5
- 238000000034 method Methods 0.000 title description 19
- 238000002360 preparation method Methods 0.000 title description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical class OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 67
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000002314 glycerols Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 111
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 61
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 54
- -1 alkyl radical Chemical class 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- DHILWXDGDAHFPS-UHFFFAOYSA-N 1-methoxy-3-[methyl(octadecyl)amino]propan-2-ol Chemical compound CCCCCCCCCCCCCCCCCCN(C)CC(O)COC DHILWXDGDAHFPS-UHFFFAOYSA-N 0.000 description 15
- 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 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 239000003480 eluent Substances 0.000 description 11
- 239000001294 propane Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 10
- AOLMUHFESNSJEE-UHFFFAOYSA-N 1-methoxy-3-phenylmethoxypropan-2-ol Chemical compound COCC(O)COCC1=CC=CC=C1 AOLMUHFESNSJEE-UHFFFAOYSA-N 0.000 description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
- 101150041968 CDC13 gene Proteins 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 9
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- 239000000243 solution Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- YHHSONZFOIEMCP-UHFFFAOYSA-O phosphocholine Chemical compound C[N+](C)(C)CCOP(O)(O)=O YHHSONZFOIEMCP-UHFFFAOYSA-O 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- PHVXTQIROLEEDB-UHFFFAOYSA-N n-[2-(2-chlorophenyl)ethyl]-4-[[3-(2-methylphenyl)piperidin-1-yl]methyl]-n-pyrrolidin-3-ylbenzamide Chemical compound CC1=CC=CC=C1C1CN(CC=2C=CC(=CC=2)C(=O)N(CCC=2C(=CC=CC=2)Cl)C2CNCC2)CCC1 PHVXTQIROLEEDB-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- TZYWCYJVHRLUCT-VABKMULXSA-N N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal Chemical compound CC(C)C[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1 TZYWCYJVHRLUCT-VABKMULXSA-N 0.000 description 3
- YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 3
- SZEGKVHRCLBFKJ-UHFFFAOYSA-N n-methyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNC SZEGKVHRCLBFKJ-UHFFFAOYSA-N 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 3
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- 206010058467 Lung neoplasm malignant Diseases 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- HPKJGHVHQWJOOT-ZJOUEHCJSA-N N-[(2S)-3-cyclohexyl-1-oxo-1-({(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}amino)propan-2-yl]-1H-indole-2-carboxamide Chemical compound C1C(CCCC1)C[C@H](NC(=O)C=1NC2=CC=CC=C2C=1)C(=O)N[C@@H](C[C@H]1C(=O)NCC1)C=O HPKJGHVHQWJOOT-ZJOUEHCJSA-N 0.000 description 2
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- 125000003277 amino group Chemical group 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- OSVHLUXLWQLPIY-KBAYOESNSA-N butyl 2-[(6aR,9R,10aR)-1-hydroxy-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl]-2-methylpropanoate Chemical compound C(CCC)OC(C(C)(C)C1=CC(=C2[C@H]3[C@H](C(OC2=C1)(C)C)CC[C@H](C3)CO)O)=O OSVHLUXLWQLPIY-KBAYOESNSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
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- 235000019256 formaldehyde Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 201000005296 lung carcinoma Diseases 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/10—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with one amino group and at least two hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Furan Compounds (AREA)
- Steroid Compounds (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898929074A GB8929074D0 (en) | 1989-12-22 | 1989-12-22 | Glycerol derivatives |
| GB898929075A GB8929075D0 (en) | 1989-12-22 | 1989-12-22 | Glycerol derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU87860A1 true LU87860A1 (fr) | 1991-05-07 |
Family
ID=26296423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU87860A LU87860A1 (fr) | 1989-12-22 | 1990-12-14 | Derives du glycerol,un procede de preparation de ces derives et des compositions therapeutiques les contenant |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US5116992A (ja) |
| JP (1) | JP2648730B2 (ja) |
| KR (1) | KR950012533B1 (ja) |
| AR (1) | AR247875A1 (ja) |
| AT (1) | AT398423B (ja) |
| AU (1) | AU635991B2 (ja) |
| BE (1) | BE1004091A3 (ja) |
| CA (1) | CA2032254C (ja) |
| CH (1) | CH681225A5 (ja) |
| DE (1) | DE4041449A1 (ja) |
| DK (1) | DK171021B1 (ja) |
| ES (1) | ES2027550A6 (ja) |
| FI (1) | FI906203A (ja) |
| FR (2) | FR2656221B1 (ja) |
| GR (1) | GR1000688B (ja) |
| HK (1) | HK117993A (ja) |
| IE (1) | IE65821B1 (ja) |
| IT (1) | IT1243413B (ja) |
| LU (1) | LU87860A1 (ja) |
| NL (1) | NL9002742A (ja) |
| NO (1) | NO178698C (ja) |
| NZ (1) | NZ236483A (ja) |
| OA (1) | OA09336A (ja) |
| PT (1) | PT96322B (ja) |
| SE (1) | SE501393C2 (ja) |
| TN (1) | TNSN90153A1 (ja) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8928580D0 (en) * | 1989-12-19 | 1990-02-21 | Scras | 3-(n-methyl-n-alkylamino)-methoxymethyl-propanol phosphocholine derivatives |
| US5206027A (en) * | 1990-09-13 | 1993-04-27 | Fuji Photo Film Co., Ltd. | Amphipathic compound and liposome comprising the same |
| US5962437A (en) | 1994-08-29 | 1999-10-05 | Wake Forest University | Lipid analogs for treating viral infections |
| US7135584B2 (en) * | 1995-08-07 | 2006-11-14 | Wake Forest University | Lipid analogs for treating viral infections |
| US5707978A (en) * | 1994-11-22 | 1998-01-13 | Clarion Pharmaceuticals Inc. | Heteroaryl-substituted deoxy glycero-phosphoethanolamines |
| US5665714A (en) * | 1995-12-07 | 1997-09-09 | Clarion Pharmaceuticals Inc. | N-substituted glycerophosphoethanolamines |
| US5703062A (en) * | 1995-12-07 | 1997-12-30 | Clarion Pharmaceuticals Inc. | N-het-substituted glycerophosphoethanolamines |
| US5730157A (en) * | 1995-12-07 | 1998-03-24 | Clarion Pharmaceuticals Inc. | Method for treating viral infection |
| US5827836A (en) * | 1996-11-15 | 1998-10-27 | Clarion Pharmaceuticals Inc. | Retinoid glycerol phospholipid conjugates |
| US5891881A (en) * | 1997-11-21 | 1999-04-06 | Clarion Pharmaceuticals Inc. | Aminoheterocycle-substituted glycerols |
| US20050187192A1 (en) * | 2004-02-20 | 2005-08-25 | Kucera Pharmaceutical Company | Phospholipids for the treatment of infection by togaviruses, herpes viruses and coronaviruses |
| PL2574341T3 (pl) | 2004-03-29 | 2017-09-29 | University Of South Florida | Efektywne leczenie guzów i raka fosforanem tricyrybiny |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2820893C2 (de) * | 1978-05-12 | 1986-02-20 | A. Nattermann & Cie GmbH, 5000 Köln | Strukturanaloga von natürlichen Phospholipiden und Verfahren zur Herstellung dieser Verbindungen |
| US4562179A (en) * | 1982-04-19 | 1985-12-31 | Fujisawa Pharmaceutical Co., Ltd. | Phospholipid derivatives, and pharmaceutical composition of the same |
| DE3323871A1 (de) * | 1983-07-02 | 1985-01-03 | A. Nattermann & Cie GmbH, 5000 Köln | Neue 1-o-alkyl-3-amino-propan-1,2-diol-2-o-phospholipide, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| US4863941A (en) * | 1985-06-18 | 1989-09-05 | Hoffmann-La Roche Inc. | Glycerol derivatives |
-
1990
- 1990-12-07 GR GR900100847A patent/GR1000688B/el unknown
- 1990-12-12 SE SE9003973A patent/SE501393C2/sv unknown
- 1990-12-12 NO NO905377A patent/NO178698C/no unknown
- 1990-12-13 NL NL9002742A patent/NL9002742A/nl not_active Application Discontinuation
- 1990-12-14 LU LU87860A patent/LU87860A1/fr unknown
- 1990-12-14 CA CA002032254A patent/CA2032254C/en not_active Expired - Fee Related
- 1990-12-17 FI FI906203A patent/FI906203A/fi not_active Application Discontinuation
- 1990-12-17 CH CH4007/90A patent/CH681225A5/fr not_active IP Right Cessation
- 1990-12-17 NZ NZ236483A patent/NZ236483A/xx unknown
- 1990-12-18 AR AR90318644A patent/AR247875A1/es active
- 1990-12-18 BE BE9001220A patent/BE1004091A3/fr not_active IP Right Cessation
- 1990-12-19 FR FR909015903A patent/FR2656221B1/fr not_active Expired - Fee Related
- 1990-12-19 FR FR9015902A patent/FR2656308B1/fr not_active Expired - Fee Related
- 1990-12-19 IT IT02243990A patent/IT1243413B/it active IP Right Grant
- 1990-12-19 US US07/630,296 patent/US5116992A/en not_active Expired - Fee Related
- 1990-12-19 TN TNTNSN90153A patent/TNSN90153A1/fr unknown
- 1990-12-20 IE IE461890A patent/IE65821B1/en not_active IP Right Cessation
- 1990-12-20 AT AT0260590A patent/AT398423B/de not_active IP Right Cessation
- 1990-12-21 PT PT96322A patent/PT96322B/pt not_active IP Right Cessation
- 1990-12-21 ES ES9003271A patent/ES2027550A6/es not_active Expired - Fee Related
- 1990-12-21 DE DE4041449A patent/DE4041449A1/de not_active Ceased
- 1990-12-21 AU AU68379/90A patent/AU635991B2/en not_active Ceased
- 1990-12-21 DK DK304090A patent/DK171021B1/da not_active IP Right Cessation
- 1990-12-21 OA OA59931A patent/OA09336A/xx unknown
- 1990-12-21 KR KR1019900021354A patent/KR950012533B1/ko not_active IP Right Cessation
- 1990-12-21 JP JP2419284A patent/JP2648730B2/ja not_active Expired - Lifetime
-
1993
- 1993-11-04 HK HK1179/93A patent/HK117993A/xx not_active IP Right Cessation
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