DE69711081T2 - Farnesyl transferase inhibitoren - Google Patents
Farnesyl transferase inhibitorenInfo
- Publication number
- DE69711081T2 DE69711081T2 DE69711081T DE69711081T DE69711081T2 DE 69711081 T2 DE69711081 T2 DE 69711081T2 DE 69711081 T DE69711081 T DE 69711081T DE 69711081 T DE69711081 T DE 69711081T DE 69711081 T2 DE69711081 T2 DE 69711081T2
- Authority
- DE
- Germany
- Prior art keywords
- methoxyphenyl
- 3ars
- 9ars
- benzo
- isoindole
- 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
- 239000003528 protein farnesyltransferase inhibitor Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 215
- -1 alkyl radicals Chemical class 0.000 claims description 180
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 145
- 125000003118 aryl group Chemical group 0.000 claims description 127
- 238000002360 preparation method Methods 0.000 claims description 111
- 238000010992 reflux Methods 0.000 claims description 95
- 239000011541 reaction mixture Substances 0.000 claims description 68
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 67
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 65
- 125000004432 carbon atom Chemical group C* 0.000 claims description 52
- 150000003857 carboxamides Chemical class 0.000 claims description 52
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 47
- 150000003254 radicals Chemical class 0.000 claims description 46
- 239000002253 acid Substances 0.000 claims description 45
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 45
- 239000003960 organic solvent Substances 0.000 claims description 40
- 230000009471 action Effects 0.000 claims description 34
- 238000011282 treatment Methods 0.000 claims description 30
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 25
- 230000003287 optical effect Effects 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000006239 protecting group Chemical group 0.000 claims description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
- OMXJXAHPPQYWRS-UHFFFAOYSA-N COC1=CC=CC=C1C(=C)C(=O)N1CC(C(O)=O)(C2C3=CC=CC=C3C3(C=4C=CC(C)=CC=4)CC2)C3C1 Chemical compound COC1=CC=CC=C1C(=C)C(=O)N1CC(C(O)=O)(C2C3=CC=CC=C3C3(C=4C=CC(C)=CC=4)CC2)C3C1 OMXJXAHPPQYWRS-UHFFFAOYSA-N 0.000 claims description 19
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 18
- 150000001412 amines Chemical group 0.000 claims description 17
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 206010028980 Neoplasm Diseases 0.000 claims description 15
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 15
- 150000008064 anhydrides Chemical class 0.000 claims description 15
- 108010007508 Farnesyltranstransferase Proteins 0.000 claims description 14
- 102000007317 Farnesyltranstransferase Human genes 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 11
- 201000011510 cancer Diseases 0.000 claims description 10
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- 125000005843 halogen group Chemical group 0.000 claims description 10
- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims description 10
- 230000004663 cell proliferation Effects 0.000 claims description 9
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
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- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 208000029742 colonic neoplasm Diseases 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- YOUFEADCSHUSQK-UHFFFAOYSA-N 1-(4-methoxyphenyl)-11-[2-(2-methoxyphenyl)prop-2-enoyl]-8-methyl-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1(C2CN(CC22C(O)=O)C(=O)C(=C)C=3C(=CC=CC=3)OC)C3=CC=CC=C3C2(C)CC1 YOUFEADCSHUSQK-UHFFFAOYSA-N 0.000 claims description 7
- 206010009944 Colon cancer Diseases 0.000 claims description 7
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 7
- 102000004169 proteins and genes Human genes 0.000 claims description 7
- 108090000623 proteins and genes Proteins 0.000 claims description 7
- 239000002841 Lewis acid Substances 0.000 claims description 6
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- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 6
- OZABRLSRWAKWOC-UHFFFAOYSA-N 1-(3-methoxyphenyl)-11-[2-(2-methoxyphenyl)acetyl]-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC(C23C4=CC=CC=C4C(CC2)C2(C3CN(C2)C(=O)CC=2C(=CC=CC=2)OC)C(O)=O)=C1 OZABRLSRWAKWOC-UHFFFAOYSA-N 0.000 claims description 5
- HNRHTONLHGQAAB-UHFFFAOYSA-N 6-methoxy-11-[2-(2-methoxyphenyl)prop-2-enoyl]-1-(4-methylphenyl)-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC=C1C(=C)C(=O)N1CC(C(O)=O)(C2C3=C(OC)C=CC=C3C3(C=4C=CC(C)=CC=4)CC2)C3C1 HNRHTONLHGQAAB-UHFFFAOYSA-N 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 150000001543 aryl boronic acids Chemical class 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- GHXZPUGJZVBLGC-UHFFFAOYSA-N iodoethene Chemical group IC=C GHXZPUGJZVBLGC-UHFFFAOYSA-N 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- 150000004702 methyl esters Chemical class 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- 230000009466 transformation Effects 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- QZVKNNFTCQKJKD-UHFFFAOYSA-N 1-(4-bromophenyl)-11-[2-(2-methoxyphenyl)prop-2-enoyl]-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC=C1C(=C)C(=O)N1CC(C(O)=O)(C2C3=CC=CC=C3C3(C=4C=CC(Br)=CC=4)CC2)C3C1 QZVKNNFTCQKJKD-UHFFFAOYSA-N 0.000 claims description 4
- URZSOMZSASLCGC-UHFFFAOYSA-N 1-(4-chlorophenyl)-11-[2-(2-methoxyphenyl)prop-2-enoyl]-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC=C1C(=C)C(=O)N1CC(C(O)=O)(C2C3=CC=CC=C3C3(C=4C=CC(Cl)=CC=4)CC2)C3C1 URZSOMZSASLCGC-UHFFFAOYSA-N 0.000 claims description 4
- LXRKXFHCZGPPHO-UHFFFAOYSA-N 11-[2-(2-methoxyphenyl)acetyl]-1-(3-methylphenyl)-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC=C1CC(=O)N1CC(C(O)=O)(C2C3=CC=CC=C3C3(C=4C=C(C)C=CC=4)CC2)C3C1 LXRKXFHCZGPPHO-UHFFFAOYSA-N 0.000 claims description 4
- UDZZWRKBCUBIFJ-UHFFFAOYSA-N 11-[2-(2-methoxyphenyl)prop-2-enoyl]-1-naphthalen-2-yl-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC=C1C(=C)C(=O)N1CC(C(O)=O)(C2C3=CC=CC=C3C3(C=4C=C5C=CC=CC5=CC=4)CC2)C3C1 UDZZWRKBCUBIFJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- MUZFJXCDFUSGGD-UHFFFAOYSA-N N-hydroxy-11-[2-(2-methoxyphenyl)prop-2-enoyl]-1-(4-methylphenyl)-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxamide Chemical compound COC1=CC=CC=C1C(=C)C(=O)N1CC(C(=O)NO)(C2C3=CC=CC=C3C3(C=4C=CC(C)=CC=4)CC2)C3C1 MUZFJXCDFUSGGD-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 210000000056 organ Anatomy 0.000 claims description 4
- ACKHCMSNGJBQJU-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-11-[2-(2-methoxyphenyl)prop-2-enoyl]-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC=C1C(=C)C(=O)N1CC(C(O)=O)(C2C3=CC=CC=C3C3(C=4C=C5OCCOC5=CC=4)CC2)C3C1 ACKHCMSNGJBQJU-UHFFFAOYSA-N 0.000 claims description 3
- DJPCBHJJHPRFMH-UHFFFAOYSA-N 1-(4-methoxy-3-methylphenyl)-11-[2-(2-methoxyphenyl)prop-2-enoyl]-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound C1=C(C)C(OC)=CC=C1C1(C2CN(CC22C(O)=O)C(=O)C(=C)C=3C(=CC=CC=3)OC)C3=CC=CC=C3C2CC1 DJPCBHJJHPRFMH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
- YHKLNWJNQGVQGC-UHFFFAOYSA-N 11-[2-(2-methoxyphenyl)prop-2-enoyl]-1-[4-(trifluoromethyl)phenyl]-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC=C1C(=C)C(=O)N1CC(C(O)=O)(C2C3=CC=CC=C3C3(C=4C=CC(=CC=4)C(F)(F)F)CC2)C3C1 YHKLNWJNQGVQGC-UHFFFAOYSA-N 0.000 claims description 3
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- VNKZFVXPTIEJGQ-UHFFFAOYSA-N C(N)(=O)C12C3C4=C(C(C2CN(C1)C(C(=C)C1=C(C=CC=C1)OC)=O)(CC3)C1=CC=C(C=C1)C)C=CC=C4 Chemical compound C(N)(=O)C12C3C4=C(C(C2CN(C1)C(C(=C)C1=C(C=CC=C1)OC)=O)(CC3)C1=CC=C(C=C1)C)C=CC=C4 VNKZFVXPTIEJGQ-UHFFFAOYSA-N 0.000 claims description 3
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- QVKNYHOTHOBIEG-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-11-[2-(2-methoxyphenyl)prop-2-enoyl]-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC=C1C(=C)C(=O)N1CC(C(O)=O)(C2C3=CC=CC=C3C3(C=4C=C(Cl)C(Cl)=CC=4)CC2)C3C1 QVKNYHOTHOBIEG-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- 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
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- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/72—4,7-Endo-alkylene-iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9616206A FR2757855B1 (fr) | 1996-12-30 | 1996-12-30 | Nouveaux inhibiteurs de farnesyl transferase, leur preparation et les compositions pharmaceutiques qui les contiennent |
| PCT/FR1997/002407 WO1998029390A1 (fr) | 1996-12-30 | 1997-12-23 | Inhibiteurs de farnesyle transferase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69711081D1 DE69711081D1 (de) | 2002-04-18 |
| DE69711081T2 true DE69711081T2 (de) | 2002-08-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69711081T Expired - Fee Related DE69711081T2 (de) | 1996-12-30 | 1997-12-23 | Farnesyl transferase inhibitoren |
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| FR (1) | FR2757855B1 (enExample) |
| HU (1) | HUP0001747A3 (enExample) |
| ID (1) | ID22922A (enExample) |
| IL (1) | IL130453A0 (enExample) |
| MA (1) | MA26460A1 (enExample) |
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| NZ (1) | NZ336042A (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2787327B1 (fr) * | 1998-12-21 | 2003-01-17 | Aventis Pharma Sa | Compositions contenant des inhibiteurs de farnesyle transferase |
| FR2796640A1 (fr) * | 1999-07-22 | 2001-01-26 | Aventis Pharma Sa | Nouveaux inhibiteurs de farnesyle transferase, leur preparation, les compositions pharmaceutiques qui les contiennent et leur utilisation pour la preparation de medicaments |
| FR2796641B1 (fr) * | 1999-07-22 | 2001-09-21 | Aventis Pharma Sa | Nouveau procede de preparation de composes benzoperhydroisoindole |
| FR2845994B1 (fr) * | 2002-10-18 | 2006-05-19 | Servier Lab | Nouveaux derives de benzo[e][1,4]oxazino[3,2-g]isoindole substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CA2559221A1 (en) * | 2004-03-18 | 2005-09-29 | Brigham And Women's Hospital, Inc. | Methods for the treatment of synucleinopathies |
| KR20260019479A (ko) | 2023-05-04 | 2026-02-10 | 레볼루션 메디슨즈, 인크. | Ras 관련 질환 또는 장애를 위한 병용 요법 |
| AU2024360465A1 (en) | 2023-10-12 | 2026-04-09 | Revolution Medicines, Inc. | Macrocyclic ras inhibitors |
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| US20250375445A1 (en) | 2024-06-07 | 2025-12-11 | Revolution Medicines, Inc. | Methods of treating a ras protein-related disease or disorder |
| WO2025265060A1 (en) | 2024-06-21 | 2025-12-26 | Revolution Medicines, Inc. | Therapeutic compositions and methods for managing treatment-related effects |
| WO2026006747A1 (en) | 2024-06-28 | 2026-01-02 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2026015801A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Methods of treating a ras related disease or disorder |
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| WO2026015790A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Methods of treating a ras related disease or disorder |
| WO2026015796A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Methods of treating a ras related disease or disorder |
| WO2026050446A1 (en) | 2024-08-29 | 2026-03-05 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2026072904A2 (en) | 2024-09-26 | 2026-04-02 | Revolution Medicines, Inc. | Compositions and methods for treating lung cancer |
| WO2026090116A2 (en) | 2024-10-21 | 2026-04-30 | Revolution Medicines, Inc. | Ras inhibitors |
| US20260108528A1 (en) | 2024-10-22 | 2026-04-23 | Revolution Medicines, Inc. | Methods of treating a ras protein-related disease or disorder |
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| WO2026106912A1 (en) | 2024-11-12 | 2026-05-21 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2026112260A1 (en) | 2024-11-21 | 2026-05-28 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2026122764A2 (en) | 2024-12-06 | 2026-06-11 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2026128688A2 (en) | 2024-12-13 | 2026-06-18 | Revolution Medicines, Inc. | Ras inhibitors |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100362338B1 (ko) * | 1993-11-05 | 2003-04-08 | 워너-램버트 캄파니 | 단백질:파르네실트랜스퍼라아제의치환디-및트리펩티드억제제 |
| FR2736641B1 (fr) * | 1995-07-10 | 1997-08-22 | Rhone Poulenc Rorer Sa | Nouveaux inhibiteurs de farnesyl transferase, leur preparation et les compositions pharmaceutiques qui les contiennent |
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1996
- 1996-12-30 FR FR9616206A patent/FR2757855B1/fr not_active Expired - Fee Related
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1997
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- 1997-12-23 KR KR1019997005966A patent/KR20000062391A/ko not_active Ceased
- 1997-12-23 JP JP52968698A patent/JP2001509147A/ja not_active Ceased
- 1997-12-23 ES ES97953000T patent/ES2172033T3/es not_active Expired - Lifetime
- 1997-12-23 SK SK883-99A patent/SK88399A3/sk unknown
- 1997-12-23 AT AT97953000T patent/ATE214367T1/de not_active IP Right Cessation
- 1997-12-23 PL PL97334345A patent/PL334345A1/xx unknown
- 1997-12-23 EP EP97953000A patent/EP0948483B1/fr not_active Expired - Lifetime
- 1997-12-23 BR BR9714498A patent/BR9714498A/pt not_active IP Right Cessation
- 1997-12-23 IL IL13045397A patent/IL130453A0/xx unknown
- 1997-12-23 TR TR1999/01502T patent/TR199901502T2/xx unknown
- 1997-12-23 YU YU30299A patent/YU30299A/sh unknown
- 1997-12-23 AU AU56694/98A patent/AU741921B2/en not_active Ceased
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- 1997-12-23 EA EA199900608A patent/EA002114B1/ru not_active IP Right Cessation
- 1997-12-23 CA CA002275943A patent/CA2275943A1/fr not_active Abandoned
- 1997-12-23 DE DE69711081T patent/DE69711081T2/de not_active Expired - Fee Related
- 1997-12-23 CZ CZ992335A patent/CZ233599A3/cs unknown
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- 1997-12-23 DK DK97953000T patent/DK0948483T3/da active
- 1997-12-23 HU HU0001747A patent/HUP0001747A3/hu unknown
- 1997-12-23 PT PT97953000T patent/PT948483E/pt unknown
- 1997-12-23 WO PCT/FR1997/002407 patent/WO1998029390A1/fr not_active Ceased
- 1997-12-26 MA MA24915A patent/MA26460A1/fr unknown
- 1997-12-26 TN TNTNSN97214A patent/TNSN97214A1/fr unknown
- 1997-12-27 DZ DZ970239A patent/DZ2389A1/xx active
- 1997-12-29 CO CO97075391A patent/CO4920252A1/es unknown
- 1997-12-30 UY UY24832A patent/UY24832A1/es not_active Application Discontinuation
- 1997-12-30 ZA ZA9711734A patent/ZA9711734B/xx unknown
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1999
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