JP2010077131A - アゾリル基を有するキノリン誘導体およびキナゾリン誘導体 - Google Patents
アゾリル基を有するキノリン誘導体およびキナゾリン誘導体 Download PDFInfo
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- JP2010077131A JP2010077131A JP2009242477A JP2009242477A JP2010077131A JP 2010077131 A JP2010077131 A JP 2010077131A JP 2009242477 A JP2009242477 A JP 2009242477A JP 2009242477 A JP2009242477 A JP 2009242477A JP 2010077131 A JP2010077131 A JP 2010077131A
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- 125000003943 azolyl group Chemical group 0.000 title claims description 13
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title abstract 2
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
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- 239000012453 solvate Substances 0.000 claims abstract description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 587
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 59
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 49
- 125000003277 amino group Chemical group 0.000 claims description 49
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- 125000005843 halogen group Chemical group 0.000 claims description 31
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
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- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 10
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- SPMVMDHWKHCIDT-UHFFFAOYSA-N 1-[2-chloro-4-[(6,7-dimethoxy-4-quinolinyl)oxy]phenyl]-3-(5-methyl-3-isoxazolyl)urea Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1Cl)=CC=C1NC(=O)NC=1C=C(C)ON=1 SPMVMDHWKHCIDT-UHFFFAOYSA-N 0.000 claims description 3
- ZIYRESLEDFVZIW-UHFFFAOYSA-N 1-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]-3-(1,3-thiazol-2-yl)urea Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NC(=O)NC1=NC=CS1 ZIYRESLEDFVZIW-UHFFFAOYSA-N 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
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- GNOMMUQGOOPKSZ-UHFFFAOYSA-N 1-[2-chloro-4-(6,7-dimethoxyquinazolin-4-yl)oxyphenyl]-3-(1,3-thiazol-2-yl)urea Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1OC(C=C1Cl)=CC=C1NC(=O)NC1=NC=CS1 GNOMMUQGOOPKSZ-UHFFFAOYSA-N 0.000 claims description 2
- KDDTWIVRCCWDFL-UHFFFAOYSA-N 1-[4-(6,7-dimethoxyquinolin-4-yl)oxy-2-fluorophenyl]-3-(4-methyl-1,3-thiazol-2-yl)urea Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1F)=CC=C1NC(=O)NC1=NC(C)=CS1 KDDTWIVRCCWDFL-UHFFFAOYSA-N 0.000 claims description 2
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 48
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
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- 229910052739 hydrogen Inorganic materials 0.000 description 13
- -1 methoxy, ethoxy, n- propoxy, i- propoxy, n- butoxy, i- butoxy, s- butoxy, t- butoxy Chemical group 0.000 description 13
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- QXTRPGAMVIONMK-UHFFFAOYSA-N 2-amino-5-ethyl-1,3,4-thiadiazole Chemical compound CCC1=NN=C(N)S1 QXTRPGAMVIONMK-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
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- XMXLBDNVSIHRRA-UHFFFAOYSA-N 2-amino-4,5-dimethyl-thiazole Natural products CC=1N=C(N)SC=1C XMXLBDNVSIHRRA-UHFFFAOYSA-N 0.000 description 7
- FNXYWHTZDAVRTB-UHFFFAOYSA-N 3-methyl-1,2-oxazol-5-amine Chemical compound CC=1C=C(N)ON=1 FNXYWHTZDAVRTB-UHFFFAOYSA-N 0.000 description 7
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- FKPXGNGUVSHWQQ-UHFFFAOYSA-N 5-methyl-1,2-oxazol-3-amine Chemical compound CC1=CC(N)=NO1 FKPXGNGUVSHWQQ-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- 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
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- C07D403/12—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 chain containing hetero atoms as chain links
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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| JP2009242477A JP2010077131A (ja) | 2001-04-27 | 2009-10-21 | アゾリル基を有するキノリン誘導体およびキナゾリン誘導体 |
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| JP2001132775 | 2001-04-27 | ||
| JP2009242477A JP2010077131A (ja) | 2001-04-27 | 2009-10-21 | アゾリル基を有するキノリン誘導体およびキナゾリン誘導体 |
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| WO2024110606A1 (en) * | 2022-11-25 | 2024-05-30 | Synthon B.V. | A process for preparation of cabozantinib or tivozanib |
| WO2025120654A1 (en) * | 2023-12-05 | 2025-06-12 | Natco Pharma Limited | An improved process for the preparation of tivozanib hydrochloride hydrate |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2728878B2 (ja) | 1987-12-15 | 1998-03-18 | 大倉工業株式会社 | 中空押出成形板 |
| GB9000644D0 (en) * | 1990-01-11 | 1990-03-14 | Erba Carlo Spa | New ureido derivatives of poly-4-amino-2-carboxy-1-methyl compounds |
| EP0860433B1 (en) * | 1995-11-07 | 2002-07-03 | Kirin Beer Kabushiki Kaisha | Quinoline derivatives and quinazoline derivatives inhibiting autophosphorylation of growth factor receptor originating in platelet and pharmaceutical compositions containing the same |
| JP4194678B2 (ja) | 1997-11-28 | 2008-12-10 | キリンファーマ株式会社 | キノリン誘導体およびそれを含む医薬組成物 |
| ATE529109T1 (de) * | 1997-12-22 | 2011-11-15 | Bayer Healthcare Llc | Hemmung der p38 kinase aktivität durch substituierte heterocyclische harnstoffe |
| NZ505844A (en) * | 1997-12-22 | 2003-10-31 | Bayer Ag | Inhibition of raf kinase using substituted heterocyclic ureas |
| ATE253051T1 (de) | 1999-01-22 | 2003-11-15 | Kirin Brewery | Chinolinderivate und chinazolinderivate |
| AU2223201A (en) | 1999-12-24 | 2001-07-09 | Kirin Beer Kabushiki Kaisha | Quinoline and quinazoline derivatives and drugs containing the same |
| JP2002030083A (ja) | 2000-07-18 | 2002-01-29 | Kirin Brewery Co Ltd | Ｎ−（２−クロロ−４−｛［６−メトキシ−７−（３−ピリジルメトキシ）−４−キノリル］オキシ｝フェニル）−ｎ’−プロピルウレアの二塩酸塩 |
| WO2002032872A1 (fr) * | 2000-10-20 | 2002-04-25 | Eisai Co., Ltd. | Composes a noyau aromatique azote |
| PL209822B1 (pl) * | 2001-04-27 | 2011-10-31 | Kirin Pharma Kk | Pochodna chinoliny lub chinazoliny, zawierająca ją kompozycja farmaceutyczna i zastosowanie |
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