DE69523462T2 - Substituierte o6-benzylguanine - Google Patents
Substituierte o6-benzylguanineInfo
- Publication number
- DE69523462T2 DE69523462T2 DE69523462T DE69523462T DE69523462T2 DE 69523462 T2 DE69523462 T2 DE 69523462T2 DE 69523462 T DE69523462 T DE 69523462T DE 69523462 T DE69523462 T DE 69523462T DE 69523462 T2 DE69523462 T2 DE 69523462T2
- Authority
- DE
- Germany
- Prior art keywords
- amino
- alkyl
- hydroxy
- benzylguanine
- group
- 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 - Fee Related
Links
- 229960005524 O6-benzylguanine Drugs 0.000 title claims description 34
- KRWMERLEINMZFT-UHFFFAOYSA-N O6-benzylguanine Chemical class C=12NC=NC2=NC(N)=NC=1OCC1=CC=CC=C1 KRWMERLEINMZFT-UHFFFAOYSA-N 0.000 title description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical group O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000011282 treatment Methods 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
- 241000124008 Mammalia Species 0.000 claims abstract description 13
- 239000002295 alkylating antineoplastic agent Substances 0.000 claims abstract description 12
- 231100000433 cytotoxic Toxicity 0.000 claims abstract description 12
- 230000001472 cytotoxic effect Effects 0.000 claims abstract description 12
- 210000004881 tumor cell Anatomy 0.000 claims abstract description 12
- 230000003902 lesion Effects 0.000 claims abstract description 11
- 230000002708 enhancing effect Effects 0.000 claims abstract description 9
- 230000000973 chemotherapeutic effect Effects 0.000 claims abstract description 8
- 239000003937 drug carrier Substances 0.000 claims abstract description 8
- -1 amino, hydroxy Chemical group 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 3
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 2
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 2
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000003441 thioacyl group Chemical group 0.000 claims description 2
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims 1
- JRHMNRMPVRXNOS-UHFFFAOYSA-N trifluoro(methoxy)methane Chemical compound COC(F)(F)F JRHMNRMPVRXNOS-UHFFFAOYSA-N 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 230000000415 inactivating effect Effects 0.000 abstract description 5
- FXXUYUZEWHFQJZ-UHFFFAOYSA-N 6-phenylmethoxy-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(OCC=2C=CC=CC=2)=N1 FXXUYUZEWHFQJZ-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
- 239000000243 solution Substances 0.000 description 36
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 27
- 206010028980 Neoplasm Diseases 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
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- 238000009472 formulation Methods 0.000 description 17
- DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 239000002502 liposome Substances 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- VPMJBCMAJPZWIC-UHFFFAOYSA-N 2-amino-6-phenylmethoxy-7,9-dihydropurin-8-one Chemical compound C=12NC(O)=NC2=NC(N)=NC=1OCC1=CC=CC=C1 VPMJBCMAJPZWIC-UHFFFAOYSA-N 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- 230000002779 inactivation Effects 0.000 description 11
- 239000000546 pharmaceutical excipient Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- 108010014722 Alkyl and Aryl Transferases Proteins 0.000 description 9
- 102000002226 Alkyl and Aryl Transferases Human genes 0.000 description 9
- 235000019445 benzyl alcohol Nutrition 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
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- 229930195729 fatty acid Natural products 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 229940100198 alkylating agent Drugs 0.000 description 7
- 239000002168 alkylating agent Substances 0.000 description 7
- 238000002512 chemotherapy Methods 0.000 description 7
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- 230000002829 reductive effect Effects 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
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- 229960000583 acetic acid Drugs 0.000 description 6
- 239000002585 base Substances 0.000 description 6
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- XSQWTUFYGIMUNS-UHFFFAOYSA-N 6-chloro-8-methyl-7h-purin-2-amine Chemical compound NC1=NC(Cl)=C2NC(C)=NC2=N1 XSQWTUFYGIMUNS-UHFFFAOYSA-N 0.000 description 5
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- AAGDJEGOOJMSHL-UHFFFAOYSA-N 6-chloro-8-(trifluoromethyl)-7h-purin-2-amine Chemical compound NC1=NC(Cl)=C2NC(C(F)(F)F)=NC2=N1 AAGDJEGOOJMSHL-UHFFFAOYSA-N 0.000 description 4
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
- C07D251/52—Two nitrogen atoms with an oxygen or sulfur atom attached to the third ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/283,953 US5525606A (en) | 1994-08-01 | 1994-08-01 | Substituted 06-benzylguanines and 6(4)-benzyloxypyrimidines |
| PCT/US1995/009702 WO1996004281A1 (en) | 1994-08-01 | 1995-07-31 | Substituted o6-benzylguanines and 6(4)-benzyloxypyrimidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69523462D1 DE69523462D1 (de) | 2001-11-29 |
| DE69523462T2 true DE69523462T2 (de) | 2002-07-11 |
Family
ID=23088285
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69523462T Expired - Fee Related DE69523462T2 (de) | 1994-08-01 | 1995-07-31 | Substituierte o6-benzylguanine |
| DE69533900T Expired - Fee Related DE69533900T2 (de) | 1994-08-01 | 1995-07-31 | Substituierte 6(4)-Benzyloxypyrimidine |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69533900T Expired - Fee Related DE69533900T2 (de) | 1994-08-01 | 1995-07-31 | Substituierte 6(4)-Benzyloxypyrimidine |
Country Status (10)
| Country | Link |
|---|---|
| US (8) | US5525606A (enExample) |
| EP (3) | EP0775142B1 (enExample) |
| JP (2) | JP3981407B2 (enExample) |
| AT (2) | ATE286054T1 (enExample) |
| CA (2) | CA2632452A1 (enExample) |
| DE (2) | DE69523462T2 (enExample) |
| DK (2) | DK0775142T3 (enExample) |
| ES (2) | ES2167451T3 (enExample) |
| PT (2) | PT1142893E (enExample) |
| WO (1) | WO1996004281A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10307928A1 (de) * | 2003-02-25 | 2004-09-16 | Faustus Forschungs Cie. Translational Cancer Research Gmbh | Verwendung von 1-(2-Chlorethyl)-1-nitroso-3-(2-hydroxyethyl)-urea zur Behandlung von Pankreaskarzinomen, Weichteilsarkomen, Hodentumoren, Lymphomen, Thymomen, Wilms Tumoren, Nierenkarzinomen, Melanomen, Lungentumoren, intracerebralen Metastasen, Tumoren im Kopf- und Halsbereich, und Mamma-Karzinomen |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6043228A (en) * | 1993-06-08 | 2000-03-28 | Cancer Research Campaign Technology Limited | O6 -substituted guanine derivatives, a process for their preparation and their use in treating tumor cells |
| US5929046A (en) * | 1994-06-08 | 1999-07-27 | Cancer Research Campaign Technology Limited | Pyrimidine and purine derivatives and their use in treating tumour cells |
| US5525606A (en) | 1994-08-01 | 1996-06-11 | The United States Of America As Represented By The Department Of Health And Human Services | Substituted 06-benzylguanines and 6(4)-benzyloxypyrimidines |
| US6794390B2 (en) * | 1996-08-02 | 2004-09-21 | Cv Therapeutics, Inc. | Purine inhibitors of cyclin dependent kinase 2 & ikappabalpha |
| DE19653646A1 (de) * | 1996-12-20 | 1998-06-25 | Hoechst Ag | Substituierte Purinderivate, Verfahren zu deren Herstellung, sie enthaltende Mittel und deren Verwendung |
| ES2253821T3 (es) * | 1997-07-12 | 2006-06-01 | Cancer Research Technology Limited | Derivados de purina inhibidores de quinasa que depende de ciclina. |
| US6060458A (en) * | 1998-02-13 | 2000-05-09 | The United States Of America As Represented By The Department Of Health And Human Services | Oligodeoxyribonucleotides comprising O6 -benzylguanine and their use |
| GB9806739D0 (en) * | 1998-03-28 | 1998-05-27 | Univ Newcastle Ventures Ltd | Cyclin dependent kinase inhibitors |
| US6677345B1 (en) * | 1998-03-28 | 2004-01-13 | Cancer Research Campaign Technology Limited | Cyclin dependent kinase inhibitors |
| US6303607B1 (en) * | 1998-09-10 | 2001-10-16 | Cv Therapeutics, Inc. | Method for administering a sustained release ranolanolazine formulation |
| KR100368515B1 (ko) * | 1999-02-03 | 2003-01-24 | 주식회사 엘지생명과학 | 싸이클린 의존 키나아제 저해제 및 그의 제조 방법 |
| US8791081B2 (en) * | 1999-08-13 | 2014-07-29 | Case Western Reserve University | MGMT inhibitor combination for the treatment of neoplastic disorders |
| US6376514B1 (en) * | 2000-10-17 | 2002-04-23 | The Procter & Gamble Co. | Substituted six-membered heterocyclic compounds useful for treating multidrug resistance and compositions and methods thereof |
| US6693099B2 (en) | 2000-10-17 | 2004-02-17 | The Procter & Gamble Company | Substituted piperazine compounds optionally containing a quinolyl moiety for treating multidrug resistance |
| AU2002216650A1 (en) * | 2000-10-31 | 2002-05-15 | Lynn Bonham | Triazine derivatives as lpaat-b inhibitors and uses thereof |
| GB0101686D0 (en) * | 2001-01-23 | 2001-03-07 | Cancer Res Campaign Tech | Cyclin dependent kinase inhibitors |
| CA2438099A1 (en) * | 2001-02-08 | 2002-12-12 | Memory Pharmaceuticals Corporation | Trifluoromethylpurines as phosphodiesterase 4 inhibitors |
| EP1554572B1 (en) | 2001-07-25 | 2009-10-14 | Raptor Pharmaceutical Inc. | Compositions and methods for modulating blood-brain barrier transport |
| US20070129334A1 (en) * | 2001-10-30 | 2007-06-07 | Conforma Therapeutics Corporation | Orally Active Purine-Based Inhibitors of Heat Shock Protein 90 |
| US7241890B2 (en) * | 2001-10-30 | 2007-07-10 | Conforma Therapeutics Corporation | Purine analogs having HSP90-inhibiting activity |
| JP2005538134A (ja) * | 2002-08-08 | 2005-12-15 | メモリー・ファーマシューティカルズ・コーポレイション | ホスホジエステラーゼ４阻害剤 |
| AU2003261418B2 (en) * | 2002-08-08 | 2010-05-27 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors |
| GB0219746D0 (en) | 2002-08-23 | 2002-10-02 | Inst Of Ex Botany Ascr | Azapurine derivatives |
| EP2145888A1 (en) * | 2003-09-18 | 2010-01-20 | Conforma Therapeutics Corporation | Deazapurine derivatives as HSP90-Inhibitors |
| EP1701957A1 (en) * | 2004-01-06 | 2006-09-20 | THE GOVERNMENT OF THE UNITED STATES OF AMERICA, represented by THE DEPARTMENT OF HEALTH & HUMAN SERVICES | 2-amino-o4-substituted pteridines and their use as inactivators of o6-alkylguanine-dna alkyltransferase |
| CA2566424A1 (en) * | 2004-05-12 | 2005-11-17 | Bayer Cropscience Gmbh | Plant growth regulation |
| US7825096B2 (en) * | 2004-09-08 | 2010-11-02 | The United States Of America As Represented By The Department Of Health And Human Services | O6-alkylguanine-DNA alkyltransferase inactivators and beta-glucuronidase cleavable prodrugs |
| WO2006029065A1 (en) * | 2004-09-08 | 2006-03-16 | Goverment Of The United States Of America Represented By The Secretary, Department Of Health And Human Services | Beta-gluguronidase cleavable prodrugs of o6-alkylguanine-dna alkyltransferase inactivators |
| CN100386115C (zh) * | 2004-10-14 | 2008-05-07 | 孔庆忠 | 一种抗癌药物组合物 |
| GB0502573D0 (en) * | 2005-02-08 | 2005-03-16 | Topotarget As | Therapeutic compounds |
| BRPI0609509A2 (pt) * | 2005-03-30 | 2010-04-13 | Conforma Therapeutics Corp | composto ou um polimorfo, solvato, tautÈmero, enanciÈmero, pró-droga ou sal farmaceuticamente aceitável do mesmo, composição farmacêutica, e, uso do composto, polimorfo, solvato, tautÈmero, enanciÈmero, pró-droga ou sal farmaceuticamente aceitável |
| WO2006114409A1 (en) * | 2005-04-27 | 2006-11-02 | Covalys Biosciences Ag | Pyrimidines reacting with o6-alkylguanine-dna alkyltransferase |
| DK1889198T3 (da) | 2005-04-28 | 2015-02-09 | Proteus Digital Health Inc | Farma-informatiksystem |
| ES2577514T3 (es) | 2005-08-22 | 2016-07-15 | The Regents Of The University Of California | Antagonistas de TLR |
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1994
- 1994-08-01 US US08/283,953 patent/US5525606A/en not_active Expired - Lifetime
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1995
- 1995-07-31 EP EP95928237A patent/EP0775142B1/en not_active Expired - Lifetime
- 1995-07-31 PT PT01108585T patent/PT1142893E/pt unknown
- 1995-07-31 DE DE69523462T patent/DE69523462T2/de not_active Expired - Fee Related
- 1995-07-31 WO PCT/US1995/009702 patent/WO1996004281A1/en not_active Ceased
- 1995-07-31 CA CA002632452A patent/CA2632452A1/en not_active Abandoned
- 1995-07-31 CA CA002195856A patent/CA2195856C/en not_active Expired - Fee Related
- 1995-07-31 ES ES95928237T patent/ES2167451T3/es not_active Expired - Lifetime
- 1995-07-31 DK DK95928237T patent/DK0775142T3/da active
- 1995-07-31 AT AT01108585T patent/ATE286054T1/de not_active IP Right Cessation
- 1995-07-31 EP EP01108585A patent/EP1142893B1/en not_active Expired - Lifetime
- 1995-07-31 DK DK01108585T patent/DK1142893T3/da active
- 1995-07-31 JP JP50669496A patent/JP3981407B2/ja not_active Expired - Lifetime
- 1995-07-31 AT AT95928237T patent/ATE207490T1/de not_active IP Right Cessation
- 1995-07-31 EP EP04030121A patent/EP1518854A1/en not_active Withdrawn
- 1995-07-31 DE DE69533900T patent/DE69533900T2/de not_active Expired - Fee Related
- 1995-07-31 ES ES01108585T patent/ES2233513T3/es not_active Expired - Lifetime
- 1995-07-31 PT PT95928237T patent/PT775142E/pt unknown
- 1995-07-31 US US08/849,223 patent/US5958932A/en not_active Expired - Fee Related
-
1996
- 1996-06-11 US US08/661,923 patent/US5753668A/en not_active Expired - Lifetime
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1997
- 1997-09-11 US US08/927,846 patent/US5916894A/en not_active Expired - Fee Related
-
1999
- 1999-05-25 US US09/318,238 patent/US6172070B1/en not_active Expired - Fee Related
- 1999-06-15 US US09/333,047 patent/US6333331B1/en not_active Expired - Fee Related
-
2000
- 2000-06-09 US US09/590,187 patent/US6303604B1/en not_active Expired - Fee Related
-
2001
- 2001-08-14 US US09/928,410 patent/US6436945B2/en not_active Expired - Fee Related
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2006
- 2006-10-04 JP JP2006273447A patent/JP2007077157A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10307928A1 (de) * | 2003-02-25 | 2004-09-16 | Faustus Forschungs Cie. Translational Cancer Research Gmbh | Verwendung von 1-(2-Chlorethyl)-1-nitroso-3-(2-hydroxyethyl)-urea zur Behandlung von Pankreaskarzinomen, Weichteilsarkomen, Hodentumoren, Lymphomen, Thymomen, Wilms Tumoren, Nierenkarzinomen, Melanomen, Lungentumoren, intracerebralen Metastasen, Tumoren im Kopf- und Halsbereich, und Mamma-Karzinomen |
Also Published As
| Publication number | Publication date |
|---|---|
| US5916894A (en) | 1999-06-29 |
| EP1518854A1 (en) | 2005-03-30 |
| ATE207490T1 (de) | 2001-11-15 |
| ES2233513T3 (es) | 2005-06-16 |
| EP0775142B1 (en) | 2001-10-24 |
| DK1142893T3 (da) | 2005-03-29 |
| PT775142E (pt) | 2002-04-29 |
| AU3207995A (en) | 1996-03-04 |
| US20020013299A1 (en) | 2002-01-31 |
| JPH10508288A (ja) | 1998-08-18 |
| US6303604B1 (en) | 2001-10-16 |
| EP1142893A1 (en) | 2001-10-10 |
| DE69523462D1 (de) | 2001-11-29 |
| US6436945B2 (en) | 2002-08-20 |
| JP2007077157A (ja) | 2007-03-29 |
| CA2195856C (en) | 2008-09-30 |
| DE69533900T2 (de) | 2005-12-29 |
| DE69533900D1 (de) | 2005-02-03 |
| EP0775142A1 (en) | 1997-05-28 |
| JP3981407B2 (ja) | 2007-09-26 |
| AU702711B2 (en) | 1999-03-04 |
| CA2632452A1 (en) | 1996-02-15 |
| US6172070B1 (en) | 2001-01-09 |
| US5753668A (en) | 1998-05-19 |
| US6333331B1 (en) | 2001-12-25 |
| CA2195856A1 (en) | 1996-02-15 |
| ES2167451T3 (es) | 2002-05-16 |
| PT1142893E (pt) | 2005-04-29 |
| EP1142893B1 (en) | 2004-12-29 |
| ATE286054T1 (de) | 2005-01-15 |
| US5525606A (en) | 1996-06-11 |
| DK0775142T3 (da) | 2002-02-18 |
| US5958932A (en) | 1999-09-28 |
| WO1996004281A1 (en) | 1996-02-15 |
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