ZA200101173B - Alkynyl-substituted quinolin-2-one derivtives useful as anticancer agents. - Google Patents
Alkynyl-substituted quinolin-2-one derivtives useful as anticancer agents. Download PDFInfo
- Publication number
- ZA200101173B ZA200101173B ZA200101173A ZA200101173A ZA200101173B ZA 200101173 B ZA200101173 B ZA 200101173B ZA 200101173 A ZA200101173 A ZA 200101173A ZA 200101173 A ZA200101173 A ZA 200101173A ZA 200101173 B ZA200101173 B ZA 200101173B
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- ZA
- South Africa
- Prior art keywords
- cancer
- methyl
- group
- alkyl
- aryl
- Prior art date
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- ZHEXQJWSYFBWJT-UHFFFAOYSA-N 6-(4-chlorobenzoyl)-1-methyl-4-[3-(4-trityloxybut-1-ynyl)phenyl]quinolin-2-one Chemical compound C=1C(=O)N(C)C2=CC=C(C(=O)C=3C=CC(Cl)=CC=3)C=C2C=1C(C=1)=CC=CC=1C#CCCOC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZHEXQJWSYFBWJT-UHFFFAOYSA-N 0.000 claims description 2
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- 230000000694 effects Effects 0.000 description 1
- 210000004696 endometrium Anatomy 0.000 description 1
- YSMODUONRAFBET-UHNVWZDZSA-N erythro-5-hydroxy-L-lysine Chemical compound NC[C@H](O)CC[C@H](N)C(O)=O YSMODUONRAFBET-UHNVWZDZSA-N 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
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- 239000011737 fluorine Substances 0.000 description 1
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- 125000003838 furazanyl group Chemical group 0.000 description 1
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- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
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- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 description 1
- 229960002591 hydroxyproline Drugs 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
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- GXHMMDRXHUIUMN-UHFFFAOYSA-N methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O GXHMMDRXHUIUMN-UHFFFAOYSA-N 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
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- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
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- 125000003551 oxepanyl group Chemical group 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920001184 polypeptide Chemical group 0.000 description 1
- 230000034918 positive regulation of cell growth Effects 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 108090000765 processed proteins & peptides Chemical group 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 235000004252 protein component Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
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- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
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- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
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- 108700042226 ras Genes Proteins 0.000 description 1
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
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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
- C07D401/10—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 aromatic rings
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
- 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
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9814598P | 1998-08-27 | 1998-08-27 |
Publications (1)
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|---|---|
| ZA200101173B true ZA200101173B (en) | 2002-04-12 |
Family
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| Application Number | Title | Priority Date | Filing Date |
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| ZA200101173A ZA200101173B (en) | 1998-08-27 | 2001-02-12 | Alkynyl-substituted quinolin-2-one derivtives useful as anticancer agents. |
Country Status (40)
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| EP (1) | EP1107963B1 (zh) |
| JP (1) | JP3495706B2 (zh) |
| KR (1) | KR20010072991A (zh) |
| CN (1) | CN1314904A (zh) |
| AP (1) | AP2001002079A0 (zh) |
| AT (1) | ATE321037T1 (zh) |
| AU (1) | AU4925499A (zh) |
| BG (1) | BG105365A (zh) |
| BR (1) | BRPI9913138B8 (zh) |
| CA (2) | CA2578326C (zh) |
| CO (1) | CO5130017A1 (zh) |
| CZ (1) | CZ2001660A3 (zh) |
| DE (1) | DE69930518T2 (zh) |
| DZ (1) | DZ2880A1 (zh) |
| EA (1) | EA200100135A1 (zh) |
| EE (1) | EE200100118A (zh) |
| ES (1) | ES2259237T3 (zh) |
| GE (1) | GEP20033001B (zh) |
| GT (1) | GT199900140A (zh) |
| HK (1) | HK1039123A1 (zh) |
| HR (1) | HRP20010142A2 (zh) |
| HU (1) | HUP0103228A3 (zh) |
| ID (1) | ID27562A (zh) |
| IL (1) | IL141239A0 (zh) |
| IS (1) | IS5818A (zh) |
| MA (1) | MA26680A1 (zh) |
| NO (1) | NO20010964L (zh) |
| NZ (1) | NZ509372A (zh) |
| OA (1) | OA11645A (zh) |
| PA (1) | PA8480101A1 (zh) |
| PE (1) | PE20000986A1 (zh) |
| PL (1) | PL346426A1 (zh) |
| SK (1) | SK2442001A3 (zh) |
| SV (1) | SV1999000141A (zh) |
| TN (1) | TNSN99162A1 (zh) |
| TR (1) | TR200101343T2 (zh) |
| UY (1) | UY25682A1 (zh) |
| WO (1) | WO2000012499A1 (zh) |
| ZA (1) | ZA200101173B (zh) |
Families Citing this family (85)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030114503A1 (en) * | 1997-06-16 | 2003-06-19 | Pfizer Inc. | Farnesyl transferase inhibitors in combination with HMG CoA reductase inhibitors for the treatment of cancer |
| SI1094815T1 (en) * | 1998-07-06 | 2004-04-30 | Janssen Pharmaceutica N.V. | Farnesyl protein transferase inhibitors for treating arthropathies |
| EP1107962B1 (en) * | 1998-08-27 | 2005-02-23 | Pfizer Products Inc. | Quinolin-2-one derivatives useful as anticancer agents |
| CZ2001660A3 (cs) * | 1998-08-27 | 2002-05-15 | Pfizer Products Inc. | Alkynylsubstituované chinolin-2-ony, farmaceutické kompozice a způsoby léčení na jejich bázi a způsob výroby těchto sloučenin |
| AU2124800A (en) | 1999-02-11 | 2000-08-29 | Pfizer Products Inc. | Heteroaryl-substituted quinolin-2-one derivatives useful as anticancer agents |
| HN2000000266A (es) | 2000-01-21 | 2001-05-21 | Pfizer Prod Inc | Compuesto anticanceroso y metodo de separacion de enantiomeros util para sintetizar dicho compuesto. |
| ATE375794T1 (de) | 2000-02-24 | 2007-11-15 | Janssen Pharmaceutica Nv | Dosierschema enthaldend farnesyl protein transferase inhibitoren für die behandlung von krebs |
| JO2361B1 (en) | 2000-06-22 | 2006-12-12 | جانسين فارماسيوتيكا ان. في | Enaniumer 1,2-anylated quinoline inhibitor for the transporter - farnesyl |
| EP1322650B1 (en) * | 2000-09-25 | 2008-09-24 | Janssen Pharmaceutica N.V. | Farnesyl transferase inhibiting 6-heterocyclylmethyl quinoline and quinazoline derivatives |
| AU2001293826A1 (en) | 2000-09-25 | 2002-04-02 | Janssen Pharmaceutica N.V. | Farnesyl transferase inhibiting quinoline and quinazoline derivatives as farnesyl transferase inhibitors |
| US7067531B2 (en) | 2000-09-25 | 2006-06-27 | Angibaud Patrick Rene | Farnesyl transferase inhibiting 6-heterocyclylmethyl quinolinone derivatives |
| US7173040B2 (en) | 2000-09-25 | 2007-02-06 | Janssen Pharmaceutica N.V. | Farnesyl transferase inhibiting 6-[(substituted phenyl)methyl]-quinoline and quinazoline derinazoline derivatives |
| AU2002214056A1 (en) | 2000-11-21 | 2002-06-03 | Janssen Pharmaceutica N.V. | Farnesyl transferase inhibiting benzoheterocyclic derivatives |
| CA2432137C (en) | 2000-12-19 | 2010-12-21 | Pfizer Products Inc. | Crystal forms of 6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3h-imidazol-4-yl)-methyl]-4-(3-ethynyl-phenyl)-1-methyl-1h-quinolin-2-one, 2,3-dihydroxybutanedioate salts and method of production |
| ATE319704T1 (de) | 2000-12-27 | 2006-03-15 | Janssen Pharmaceutica Nv | Farnesyltransferase hemmende, in der 4-stellung substituierte chinolin- und chinazolinderivate |
| WO2002056884A2 (en) * | 2001-01-22 | 2002-07-25 | Schering Corporation | Treatment of malaria with farnesyl protein transferase inhibitors |
| EP1373255B1 (en) | 2001-03-12 | 2005-01-26 | Janssen Pharmaceutica N.V. | Process for the preparation of imidazole compounds |
| US20020151563A1 (en) * | 2001-03-29 | 2002-10-17 | Pfizer Inc. | Farnesyl transferase inhibitors in combination with HMG CoA reductase inhibitors for the inhibition of abnormal cell growth |
| AU2002257114A1 (en) * | 2001-04-06 | 2002-10-21 | Schering Corporation | Treatment of malaria with farsenyl protein transferase inhibitors |
| US20050165053A1 (en) * | 2001-06-04 | 2005-07-28 | Cytovia, Inc. | Substituted4-aryl-3-(3-aryl-1-oxo-2-propenyl)-2(1h)-quinolinones and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| WO2003000266A1 (en) | 2001-06-21 | 2003-01-03 | Ariad Pharmaceuticals, Inc. | Novel quinolines and uses thereof |
| US6740757B2 (en) | 2001-08-29 | 2004-05-25 | Pfizer Inc | Enantiomers of 6-[(4-chloro-phenyl)-hydroxy-(3-methyl-3h-imidazol-4-yl)-methyl]-4-[3-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl]-1-methyl-1h-quinolin-2-one and salts thereof, useful in the treatment of cancer |
| WO2003051880A1 (en) | 2001-12-19 | 2003-06-26 | Janssen Pharmaceutica N.V. | 1,8-annelated quinoline derivatives substituted with carbon-linked triazoles as farnesyl transferase inhibitors |
| AU2003223970B2 (en) | 2002-03-22 | 2008-03-06 | Janssen Pharmaceutica N.V. | Benzylimidazolyl substituted 2-quinoline and quinazoline derivatives for use as farnesyl transferase inhibitors |
| ATE336496T1 (de) | 2002-04-15 | 2006-09-15 | Janssen Pharmaceutica Nv | Farnesyl transferase hemmende tricyclische quinazolinederivate substitutiert mit kohlenstoff-gebundenen imidazolen oder triazolen |
| OA12977A (en) * | 2002-12-19 | 2006-10-13 | Pfizer | 2-(1H-indazol-6-ylamino)-benzamide compounds as protein kinases inhibitors useful for the treatment of ophthamic diseases. |
| WO2005051392A1 (en) | 2003-11-20 | 2005-06-09 | Children's Hospital Medical Center | Gtpase inhibitors and methods of use |
| WO2005089515A2 (en) * | 2004-03-18 | 2005-09-29 | The Brigham And Women's Hospital, Inc. | Methods for the treatment of synucleinopathies |
| WO2005094830A1 (en) * | 2004-03-30 | 2005-10-13 | Pfizer Products Inc. | Combinations of signal transduction inhibitors |
| JP2008510792A (ja) * | 2004-08-26 | 2008-04-10 | ファイザー・インク | タンパク質チロシンキナーゼ阻害剤としてのアミノヘテロアリール化合物 |
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| US5747498A (en) * | 1996-05-28 | 1998-05-05 | Pfizer Inc. | Alkynyl and azido-substituted 4-anilinoquinazolines |
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