IL123567A - History of 2 quinolones inhibiting frenzyl transferase, the process for their preparation and the pharmaceutical preparations containing them - Google Patents
History of 2 quinolones inhibiting frenzyl transferase, the process for their preparation and the pharmaceutical preparations containing themInfo
- Publication number
- IL123567A IL123567A IL12356796A IL12356796A IL123567A IL 123567 A IL123567 A IL 123567A IL 12356796 A IL12356796 A IL 12356796A IL 12356796 A IL12356796 A IL 12356796A IL 123567 A IL123567 A IL 123567A
- Authority
- IL
- Israel
- Prior art keywords
- alkyl
- formula
- compound
- hydrogen
- alkyloxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 15
- 230000002401 inhibitory effect Effects 0.000 title claims description 13
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title claims description 13
- 230000008569 process Effects 0.000 title claims description 5
- 102000007317 Farnesyltranstransferase Human genes 0.000 title 1
- 108010007508 Farnesyltranstransferase Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 130
- -1 amino, hydroxycarbonyl Chemical group 0.000 claims abstract description 63
- 239000001257 hydrogen Substances 0.000 claims abstract description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 49
- 239000002253 acid Substances 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000001301 oxygen Substances 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052717 sulfur Chemical group 0.000 claims abstract description 7
- 239000011593 sulfur Chemical group 0.000 claims abstract description 7
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims abstract description 3
- 125000004951 trihalomethoxy group Chemical group 0.000 claims abstract description 3
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 11
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims abstract 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 239000002585 base Substances 0.000 claims description 24
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 20
- 239000003153 chemical reaction reagent Substances 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 claims description 7
- 230000010261 cell growth Effects 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 229930185107 quinolinone Natural products 0.000 claims description 6
- 230000002159 abnormal effect Effects 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 230000004614 tumor growth Effects 0.000 claims description 5
- 150000004682 monohydrates Chemical class 0.000 claims description 4
- 150000003248 quinolines Chemical class 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 230000008707 rearrangement Effects 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 239000011260 aqueous acid Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 230000001131 transforming effect Effects 0.000 claims description 2
- 241000283160 Inia Species 0.000 claims 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 4
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 abstract 3
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 113
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 82
- 239000000543 intermediate Substances 0.000 description 79
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 61
- 239000000243 solution Substances 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- 210000004027 cell Anatomy 0.000 description 36
- 229910001868 water Inorganic materials 0.000 description 36
- 239000012044 organic layer Substances 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 32
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 239000002904 solvent Substances 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- 239000003480 eluent Substances 0.000 description 24
- 238000004440 column chromatography Methods 0.000 description 23
- 239000000741 silica gel Substances 0.000 description 23
- 229910002027 silica gel Inorganic materials 0.000 description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
- 125000001309 chloro group Chemical group Cl* 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 18
- 238000012360 testing method Methods 0.000 description 16
- 206010028980 Neoplasm Diseases 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229910000027 potassium carbonate Inorganic materials 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 102000004357 Transferases Human genes 0.000 description 14
- 108090000992 Transferases Proteins 0.000 description 14
- 125000005843 halogen group Chemical group 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 108700042226 ras Genes Proteins 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 10
- 235000015320 potassium carbonate Nutrition 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
- 235000011114 ammonium hydroxide Nutrition 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 239000000872 buffer Substances 0.000 description 7
- 108010037444 diisopropylglutathione ester Proteins 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
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- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
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- 238000007126 N-alkylation reaction Methods 0.000 description 6
- 108700020796 Oncogene Proteins 0.000 description 6
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- 230000035772 mutation Effects 0.000 description 6
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- 125000001424 substituent group Chemical group 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 102000043276 Oncogene Human genes 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000000502 dialysis Methods 0.000 description 5
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- 229910052700 potassium Inorganic materials 0.000 description 5
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- 229940093956 potassium carbonate Drugs 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
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- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
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- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
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- RSJLWBUYLGJOBD-UHFFFAOYSA-M diphenyliodanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[I+]C1=CC=CC=C1 RSJLWBUYLGJOBD-UHFFFAOYSA-M 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP95202945 | 1995-10-31 | ||
| PCT/EP1996/004661 WO1997016443A1 (en) | 1995-10-31 | 1996-10-25 | Farnesyl transferase inhibiting 2-quinolone derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL123567A0 IL123567A0 (en) | 1998-10-30 |
| IL123567A true IL123567A (en) | 2002-11-10 |
Family
ID=8220785
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12356796A IL123567A (en) | 1995-10-31 | 1996-10-25 | History of 2 quinolones inhibiting frenzyl transferase, the process for their preparation and the pharmaceutical preparations containing them |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US5968952A (no) |
| EP (2) | EP1019395B1 (no) |
| JP (1) | JP4257869B2 (no) |
| KR (1) | KR100417620B1 (no) |
| CN (1) | CN1101391C (no) |
| AR (1) | AR004699A1 (no) |
| AT (2) | ATE269322T1 (no) |
| AU (1) | AU712435B2 (no) |
| CA (1) | CA2231143C (no) |
| CY (1) | CY2287B1 (no) |
| CZ (1) | CZ290954B6 (no) |
| DE (2) | DE69632751T2 (no) |
| DK (1) | DK1019395T3 (no) |
| EA (1) | EA000719B1 (no) |
| ES (2) | ES2233557T3 (no) |
| HK (2) | HK1027576A1 (no) |
| HU (1) | HU224032B1 (no) |
| IL (1) | IL123567A (no) |
| MY (1) | MY116577A (no) |
| NO (1) | NO314037B1 (no) |
| NZ (1) | NZ321576A (no) |
| PL (1) | PL184168B1 (no) |
| PT (1) | PT1019395E (no) |
| SI (1) | SI1019395T1 (no) |
| SK (1) | SK282642B6 (no) |
| TR (1) | TR199800720T2 (no) |
| TW (1) | TW349948B (no) |
| WO (1) | WO1997016443A1 (no) |
| ZA (1) | ZA969087B (no) |
Families Citing this family (91)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4209472B2 (ja) | 1997-06-02 | 2009-01-14 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 平滑筋細胞増殖のインヒビターとしての（イミダゾール−５−イル）メチル−２−キノリノン誘導体 |
| US6565831B1 (en) | 1999-02-24 | 2003-05-20 | Oncolytics Biotech Inc. | Methods for preventing reovirus recognition for the treatment of cellular proliferative disorders |
| US6136307A (en) | 1997-08-13 | 2000-10-24 | Oncolytics Biotech Inc. | Reovirus for the treatment of cellular proliferative disorders |
| US6110461A (en) | 1997-08-13 | 2000-08-29 | Oncolytics Biotech Inc. | Reovirus for the treatment of neoplasia |
| CA2312720A1 (en) | 1997-12-11 | 1999-06-17 | Janssen-Cilag S.A. | Retinoic acid mimetic anilides |
| WO1999065898A1 (en) * | 1998-06-16 | 1999-12-23 | Societe De Conseils De Recherches Et D'applications Scientifiques Sas | Imidazolyl derivatives |
| US6420555B1 (en) | 1998-06-16 | 2002-07-16 | Societe De Conseils De Recherches Et D'applications Scientifiques, S.A.S. | Imidazolyl derivatives |
| AU762423B2 (en) * | 1998-07-06 | 2003-06-26 | Janssen Pharmaceutica N.V. | Farnesyl protein transferase inhibitors with In Vivo radiosensitizing properties |
| SI1094815T1 (en) | 1998-07-06 | 2004-04-30 | Janssen Pharmaceutica N.V. | Farnesyl protein transferase inhibitors for treating arthropathies |
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