CA2249604A1 - Inhibiteurs de farnesyl-proteine transferase - Google Patents
Inhibiteurs de farnesyl-proteine transferase Download PDFInfo
- Publication number
- CA2249604A1 CA2249604A1 CA002249604A CA2249604A CA2249604A1 CA 2249604 A1 CA2249604 A1 CA 2249604A1 CA 002249604 A CA002249604 A CA 002249604A CA 2249604 A CA2249604 A CA 2249604A CA 2249604 A1 CA2249604 A1 CA 2249604A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- alkyl
- aryl
- cycloalkyl
- unsubstituted
- 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.)
- Abandoned
Links
- 102000004357 Transferases Human genes 0.000 title claims abstract description 32
- 108090000992 Transferases Proteins 0.000 title claims abstract description 32
- 239000003112 inhibitor Substances 0.000 title description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 91
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 22
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims description 106
- 125000000623 heterocyclic group Chemical group 0.000 claims description 89
- 229910052739 hydrogen Inorganic materials 0.000 claims description 80
- 239000001257 hydrogen Substances 0.000 claims description 79
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 63
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 56
- 102200160920 rs35304565 Human genes 0.000 claims description 48
- 150000002431 hydrogen Chemical class 0.000 claims description 46
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 44
- -1 or h) SR6a Chemical group 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 24
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 23
- 229910052731 fluorine Inorganic materials 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 16
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000002950 monocyclic group Chemical group 0.000 claims description 15
- 241000124008 Mammalia Species 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000002883 imidazolyl group Chemical group 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 10
- 201000011510 cancer Diseases 0.000 claims description 9
- 125000005002 aryl methyl group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001041 indolyl group Chemical group 0.000 claims description 8
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000005494 pyridonyl group Chemical group 0.000 claims description 6
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
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- 108010085793 Neurofibromin 1 Proteins 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- JBFAUZOIZNFKFR-UHFFFAOYSA-N 4-[[5-[(4-benzyl-2,5-dioxopiperazin-1-yl)methyl]imidazol-1-yl]methyl]benzonitrile Chemical compound O=C1CN(CC=2N(C=NC=2)CC=2C=CC(=CC=2)C#N)C(=O)CN1CC1=CC=CC=C1 JBFAUZOIZNFKFR-UHFFFAOYSA-N 0.000 claims description 3
- 208000005331 Hepatitis D Diseases 0.000 claims description 3
- 208000037262 Hepatitis delta Diseases 0.000 claims description 3
- 241000700605 Viruses Species 0.000 claims description 3
- 125000003435 aroyl group Chemical group 0.000 claims description 3
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- 230000002062 proliferating effect Effects 0.000 claims description 3
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- 125000004802 cyanophenyl group Chemical group 0.000 claims description 2
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- 208000037803 restenosis Diseases 0.000 claims description 2
- 230000004276 retinal vascularization Effects 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 12
- 102220389089 c.33G>T Human genes 0.000 claims 8
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- BNROHCXPQWOXDO-UHFFFAOYSA-N C(#N)C1=CC=C(CN2C=NC=C2CN2CC(N(CC2=O)C2=CC=CC=C2)=O)C=C1.ClC=1C=C(C=CC1)N1C(CN(C(C1)=O)CC1=C(C=NC=C1)CC1=CC=C(C=C1)C#N)=O Chemical compound C(#N)C1=CC=C(CN2C=NC=C2CN2CC(N(CC2=O)C2=CC=CC=C2)=O)C=C1.ClC=1C=C(C=CC1)N1C(CN(C(C1)=O)CC1=C(C=NC=C1)CC1=CC=C(C=C1)C#N)=O BNROHCXPQWOXDO-UHFFFAOYSA-N 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
- 230000006126 farnesylation Effects 0.000 abstract description 6
- 108700020796 Oncogene Proteins 0.000 abstract description 4
- 102000043276 Oncogene Human genes 0.000 abstract description 4
- 230000000973 chemotherapeutic effect Effects 0.000 abstract description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 55
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 38
- 239000000047 product Substances 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 30
- 102000016914 ras Proteins Human genes 0.000 description 26
- 108010014186 ras Proteins Proteins 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
- 235000019439 ethyl acetate Nutrition 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 18
- 238000003556 assay Methods 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 12
- 108090000623 proteins and genes Proteins 0.000 description 12
- 150000001299 aldehydes Chemical class 0.000 description 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 11
- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 229910001868 water Inorganic materials 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000012267 brine Substances 0.000 description 10
- 230000005764 inhibitory process Effects 0.000 description 10
- BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical compound O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 description 10
- 235000018102 proteins Nutrition 0.000 description 10
- 102000004169 proteins and genes Human genes 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 9
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- 238000000746 purification Methods 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 150000003573 thiols Chemical class 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 6
- 235000001014 amino acid Nutrition 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 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 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
- VWFJDQUYCIWHTN-UHFFFAOYSA-N Farnesyl pyrophosphate Natural products CC(C)=CCCC(C)=CCCC(C)=CCOP(O)(=O)OP(O)(O)=O VWFJDQUYCIWHTN-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
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- 230000015572 biosynthetic process Effects 0.000 description 5
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- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000004030 farnesyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 230000002265 prevention Effects 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 4
- 235000018417 cysteine Nutrition 0.000 description 4
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 4
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
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- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 2
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- 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 2
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- 159000000000 sodium salts Chemical class 0.000 description 1
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- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
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- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
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
- C07D401/06—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- C07D403/06—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 linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Ophthalmology & Optometry (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
L'invention concerne des composés qui inhibent la farnésyl-protéine transférase (FTase) et la farnésylation de la protéine ras oncogène. L'invention a en outre pour objet des compositions chimiothérapeutiques contenant les composés de cette invention et des procédés pour inhiber la farnésyl-protéine transférase et la farnésylation de la protéine Ras oncogène.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1458796P | 1996-04-03 | 1996-04-03 | |
| US60/014,587 | 1996-04-03 | ||
| GB9613461.4 | 1996-06-27 | ||
| GBGB9613461.4A GB9613461D0 (en) | 1996-06-27 | 1996-06-27 | Inhibitors of farnesyl-protein transferase |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2249604A1 true CA2249604A1 (fr) | 1997-10-09 |
Family
ID=26309576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002249604A Abandoned CA2249604A1 (fr) | 1996-04-03 | 1997-03-27 | Inhibiteurs de farnesyl-proteine transferase |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0891349A4 (fr) |
| JP (1) | JP2000507576A (fr) |
| AU (1) | AU715667B2 (fr) |
| CA (1) | CA2249604A1 (fr) |
| WO (1) | WO1997036888A1 (fr) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2336475A1 (fr) | 1998-07-02 | 2000-01-13 | Christopher J. Dinsmore | Inhibiteurs de prenyl-proteine transferase |
| USRE39921E1 (en) | 1999-10-07 | 2007-11-13 | Smithkline Beecham Corporation | Chemical compounds |
| GB9923748D0 (en) | 1999-10-07 | 1999-12-08 | Glaxo Group Ltd | Chemical compounds |
| DK1311269T3 (da) | 2000-08-04 | 2012-03-26 | Dmi Biosciences Inc | Fremgangsmåde til anvendelse af diketopiperaziner og sammensætning, som indeholder dem |
| GB2382346B (en) | 2000-08-04 | 2004-08-11 | Dmi Biosciences Inc | Method of synthesizing diketopiperazines |
| GB0025354D0 (en) | 2000-10-17 | 2000-11-29 | Glaxo Group Ltd | Chemical compounds |
| EP1472222A1 (fr) | 2002-02-08 | 2004-11-03 | Glaxo Group Limited | Derives piperidylcarboxamide, et leur utilisation dans le traitement des maladies dont la mediation est assuree par les tachykinines |
| GB0203020D0 (en) | 2002-02-08 | 2002-03-27 | Glaxo Group Ltd | Chemical compounds |
| GB0203022D0 (en) | 2002-02-08 | 2002-03-27 | Glaxo Group Ltd | Chemical compounds |
| ATE520981T1 (de) | 2002-10-02 | 2011-09-15 | Dmi Biosciences Inc | Diagnose und überwachung von krankheiten |
| NZ542886A (en) | 2003-05-15 | 2009-06-26 | Dmi Biosciences Inc | Treatment of T-cell mediated diseases |
| WO2009146320A1 (fr) | 2008-05-27 | 2009-12-03 | Dmi Life Sciences, Inc. | Procédés et composés thérapeutiques |
| EP2613786A4 (fr) | 2010-09-07 | 2013-10-23 | Dmi Acquisition Corp | Traitement de maladies |
| MX362164B (es) | 2011-10-10 | 2019-01-07 | Ampio Pharmaceuticals Inc | Tratamiento de enfermedad de articulacion degenerativa. |
| EP2765968A4 (fr) | 2011-10-10 | 2015-01-21 | Ampio Pharmaceuticals Inc | Dispositifs médicaux implantables ayant une tolérance immunitaire accrue, et leurs procédés de fabrication et d'implantation |
| PH12014500715A1 (en) | 2011-10-28 | 2014-05-12 | Ampio Pharmaceuticals Inc | Treatment of rhinitis |
| SG11201506267XA (en) | 2013-03-15 | 2015-09-29 | Ampio Pharmaceuticals Inc | Compositions for the mobilization, homing, expansion and differentiation of stem cells and methods of using the same |
| WO2016028790A1 (fr) | 2014-08-18 | 2016-02-25 | Ampio Pharmaceuticals, Inc. | Traitement de pathologies articulaires |
| US11389512B2 (en) | 2015-06-22 | 2022-07-19 | Ampio Pharmaceuticals, Inc. | Use of low molecular weight fractions of human serum albumin in treating diseases |
| WO2021195265A1 (fr) | 2020-03-24 | 2021-09-30 | Ampio Pharmaceuticals, Inc. | Méthodes de traitement de maladies associées à des virus respiratoires |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54106481A (en) * | 1978-02-08 | 1979-08-21 | Toyama Chem Co Ltd | Novel 2,3-dioxopiperazine derivative and its preparation |
| US4287195A (en) * | 1978-07-14 | 1981-09-01 | Janssen Pharmaceutica, N.V. | Heterocyclic derivatives of [4-(piperazin-1-yl-phenyloxymethyl)-1,3-dioxolan-2-ylmethyl]-1H-imidazoles and 1H-1,2,4-triazoles |
| US4456605A (en) * | 1981-05-07 | 1984-06-26 | Janssen Pharmaceutica N.V. | Heterocyclic derivatives of [4-(piperazin-1-yl-phenyloxymethyl)-1,3-dioxolan-2-ylmethyl]-1H-imidazoles and 1H-1,2,4-triazoles |
| GB8507778D0 (en) * | 1985-03-26 | 1985-05-01 | Fujisawa Pharmaceutical Co | Piperazine compound |
| CA2165176A1 (fr) * | 1993-06-18 | 1995-01-05 | Samuel L. Graham | Inhibiteurs de la farnesyl-proteine transferase |
| US5728830A (en) * | 1993-09-22 | 1998-03-17 | Kyowa Hakko Kogyo Co., Ltd. | Farnesyltransferase inhibitor |
| US5478934A (en) * | 1994-11-23 | 1995-12-26 | Yuan; Jun | Certain 1-substituted aminomethyl imidazole and pyrrole derivatives: novel dopamine receptor subtype specific ligands |
-
1997
- 1997-03-27 CA CA002249604A patent/CA2249604A1/fr not_active Abandoned
- 1997-03-27 EP EP97917599A patent/EP0891349A4/fr not_active Withdrawn
- 1997-03-27 AU AU25875/97A patent/AU715667B2/en not_active Ceased
- 1997-03-27 JP JP9535347A patent/JP2000507576A/ja active Pending
- 1997-03-27 WO PCT/US1997/004711 patent/WO1997036888A1/fr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0891349A4 (fr) | 2001-01-24 |
| WO1997036888A1 (fr) | 1997-10-09 |
| EP0891349A1 (fr) | 1999-01-20 |
| AU2587597A (en) | 1997-10-22 |
| AU715667B2 (en) | 2000-02-10 |
| JP2000507576A (ja) | 2000-06-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |