SK8642002A3 - Farnesyl transferase inhibitors, process for their preparation and pharmaceutical compositions containing them - Google Patents
Farnesyl transferase inhibitors, process for their preparation and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- SK8642002A3 SK8642002A3 SK864-2002A SK8642002A SK8642002A3 SK 8642002 A3 SK8642002 A3 SK 8642002A3 SK 8642002 A SK8642002 A SK 8642002A SK 8642002 A3 SK8642002 A3 SK 8642002A3
- Authority
- SK
- Slovakia
- Prior art keywords
- compound
- formula
- optionally substituted
- ester
- carbon atoms
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title abstract description 34
- 238000002360 preparation method Methods 0.000 title description 16
- 239000003528 protein farnesyltransferase inhibitor Substances 0.000 title description 5
- 230000008569 process Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 175
- -1 cycloalkyl ester Chemical class 0.000 claims description 74
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 15
- 229940002612 prodrug Drugs 0.000 claims description 12
- 239000000651 prodrug Chemical group 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 7
- 239000003814 drug Substances 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 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000005633 phthalidyl group Chemical group 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 150000002545 isoxazoles Chemical class 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000005942 tetrahydropyridyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- INVALIZXSWWKSV-UHFFFAOYSA-N 2-amino-3-[2-(4-fluorophenyl)ethyl]benzoic acid Chemical compound C1=CC=C(C(O)=O)C(N)=C1CCC1=CC=C(F)C=C1 INVALIZXSWWKSV-UHFFFAOYSA-N 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 19
- 201000011510 cancer Diseases 0.000 abstract description 13
- 230000006126 farnesylation Effects 0.000 abstract description 11
- 201000010099 disease Diseases 0.000 abstract description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 8
- 102000004190 Enzymes Human genes 0.000 abstract description 5
- 108090000790 Enzymes Proteins 0.000 abstract description 5
- 230000001404 mediated effect Effects 0.000 abstract description 5
- 108090000623 proteins and genes Proteins 0.000 abstract description 5
- 102000004357 Transferases Human genes 0.000 abstract description 4
- 108090000992 Transferases Proteins 0.000 abstract description 4
- 230000005764 inhibitory process Effects 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000005481 NMR spectroscopy Methods 0.000 description 16
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- 102000016914 ras Proteins Human genes 0.000 description 16
- 108010014186 ras Proteins Proteins 0.000 description 16
- 238000011282 treatment Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 125000006239 protecting group Chemical group 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 10
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 238000010561 standard procedure Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000443 aerosol Substances 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 230000036961 partial effect Effects 0.000 description 8
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 8
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- 239000002253 acid Substances 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 7
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- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000003102 growth factor Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000003755 preservative agent Substances 0.000 description 6
- 239000003765 sweetening agent Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 6
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000010511 deprotection reaction Methods 0.000 description 5
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000000375 suspending agent Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- YUHZIUAREWNXJT-UHFFFAOYSA-N (2-fluoropyridin-3-yl)boronic acid Chemical class OB(O)C1=CC=CN=C1F YUHZIUAREWNXJT-UHFFFAOYSA-N 0.000 description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
- VWFJDQUYCIWHTN-YFVJMOTDSA-N 2-trans,6-trans-farnesyl diphosphate Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CO[P@](O)(=O)OP(O)(O)=O VWFJDQUYCIWHTN-YFVJMOTDSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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- 239000004338 Dichlorodifluoromethane Substances 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
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- 239000004147 Sorbitan trioleate Substances 0.000 description 4
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 4
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 4
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- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Oncology (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9930318.2A GB9930318D0 (en) | 1999-12-22 | 1999-12-22 | Novel compounds |
| PCT/GB2000/004856 WO2001046137A1 (en) | 1999-12-22 | 2000-12-18 | Farnesyl transferase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK8642002A3 true SK8642002A3 (en) | 2002-12-03 |
Family
ID=10866834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK864-2002A SK8642002A3 (en) | 1999-12-22 | 2000-12-18 | Farnesyl transferase inhibitors, process for their preparation and pharmaceutical compositions containing them |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7101897B2 (https=) |
| EP (1) | EP1255733B1 (https=) |
| JP (1) | JP3742593B2 (https=) |
| KR (1) | KR20020063251A (https=) |
| CN (2) | CN1680313A (https=) |
| AR (1) | AR029460A1 (https=) |
| AT (1) | ATE316074T1 (https=) |
| AU (1) | AU776003B2 (https=) |
| BR (1) | BR0016669A (https=) |
| CA (1) | CA2387579A1 (https=) |
| CO (1) | CO5360641A1 (https=) |
| CZ (1) | CZ20022125A3 (https=) |
| DE (1) | DE60025650D1 (https=) |
| EE (1) | EE200200206A (https=) |
| GB (1) | GB9930318D0 (https=) |
| HU (1) | HUP0204135A3 (https=) |
| IL (1) | IL149871A0 (https=) |
| IS (1) | IS6358A (https=) |
| MX (1) | MXPA02005981A (https=) |
| MY (1) | MY133606A (https=) |
| NO (1) | NO20022924D0 (https=) |
| NZ (1) | NZ518341A (https=) |
| PL (1) | PL355887A1 (https=) |
| RU (1) | RU2259997C2 (https=) |
| SK (1) | SK8642002A3 (https=) |
| WO (1) | WO2001046137A1 (https=) |
| ZA (1) | ZA200202694B (https=) |
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| WO2005117864A1 (en) * | 2004-05-28 | 2005-12-15 | Astrazeneca Ab | Combination product comprising anastrozole and a dual prenyl transferase inhibitor |
| EP1813620A4 (en) * | 2004-10-08 | 2009-12-30 | Kotobuki Pharmaceutical Co Ltd | PHOSPHONIC ACID DERIVATIVE AND THERAPEUTIC AGENT AGAINST DISEASES ASSOCIATED WITH HIGH PHOSPHAT MIRRORS IN THE BLOOD |
| US20110136867A1 (en) * | 2006-02-02 | 2011-06-09 | Justman Craig J | Treatment of Synucleinopathies |
| WO2009151683A2 (en) | 2008-03-12 | 2009-12-17 | Link Medicine Corporation | Quinolinone farnesyl transferase inhibitors for the treatment of synucleinopathies and other indications |
| NZ593090A (en) | 2008-11-13 | 2013-06-28 | Link Medicine Corp | Azaquinolinone derivatives and uses thereof |
| EP2408449A4 (en) | 2009-03-18 | 2012-08-08 | Univ Leland Stanford Junior | METHOD AND COMPOSITIONS FOR TREATING FLAVIVIRIDAE VIRUS INFECTIONS |
| WO2011088126A2 (en) * | 2010-01-13 | 2011-07-21 | Eiger Biopharmaceuticals, Inc. | Treatment of viral infection with prenyltransferase inhibitors |
| WO2018132791A1 (en) | 2017-01-16 | 2018-07-19 | The Regents Of The University Of California | Treatment of neurodegenerative conditions by disruption of rhes |
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-
1999
- 1999-12-22 GB GBGB9930318.2A patent/GB9930318D0/en not_active Ceased
-
2000
- 2000-12-18 AU AU22013/01A patent/AU776003B2/en not_active Ceased
- 2000-12-18 US US10/110,690 patent/US7101897B2/en not_active Expired - Fee Related
- 2000-12-18 CA CA002387579A patent/CA2387579A1/en not_active Abandoned
- 2000-12-18 BR BR0016669-3A patent/BR0016669A/pt not_active IP Right Cessation
- 2000-12-18 WO PCT/GB2000/004856 patent/WO2001046137A1/en not_active Ceased
- 2000-12-18 SK SK864-2002A patent/SK8642002A3/sk unknown
- 2000-12-18 KR KR1020027008034A patent/KR20020063251A/ko not_active Ceased
- 2000-12-18 EP EP00985605A patent/EP1255733B1/en not_active Expired - Lifetime
- 2000-12-18 NZ NZ518341A patent/NZ518341A/xx unknown
- 2000-12-18 MX MXPA02005981A patent/MXPA02005981A/es unknown
- 2000-12-18 IL IL14987100A patent/IL149871A0/xx unknown
- 2000-12-18 HU HU0204135A patent/HUP0204135A3/hu unknown
- 2000-12-18 DE DE60025650T patent/DE60025650D1/de not_active Expired - Lifetime
- 2000-12-18 EE EEP200200206A patent/EE200200206A/xx unknown
- 2000-12-18 PL PL00355887A patent/PL355887A1/xx not_active Application Discontinuation
- 2000-12-18 RU RU2002119405/04A patent/RU2259997C2/ru not_active IP Right Cessation
- 2000-12-18 CN CNA2005100563322A patent/CN1680313A/zh active Pending
- 2000-12-18 CN CNB008174202A patent/CN1229344C/zh not_active Expired - Fee Related
- 2000-12-18 JP JP2001547048A patent/JP3742593B2/ja not_active Expired - Fee Related
- 2000-12-18 CZ CZ20022125A patent/CZ20022125A3/cs unknown
- 2000-12-18 AT AT00985605T patent/ATE316074T1/de not_active IP Right Cessation
- 2000-12-20 MY MYPI20006011A patent/MY133606A/en unknown
- 2000-12-21 AR ARP000106845A patent/AR029460A1/es not_active Application Discontinuation
- 2000-12-22 CO CO00097282A patent/CO5360641A1/es not_active Application Discontinuation
-
2002
- 2002-04-05 ZA ZA200202694A patent/ZA200202694B/en unknown
- 2002-04-23 IS IS6358A patent/IS6358A/is unknown
- 2002-06-18 NO NO20022924A patent/NO20022924D0/no unknown
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