CN1680313A - 法尼基转移酶抑制剂 - Google Patents
法尼基转移酶抑制剂 Download PDFInfo
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- CN1680313A CN1680313A CNA2005100563322A CN200510056332A CN1680313A CN 1680313 A CN1680313 A CN 1680313A CN A2005100563322 A CNA2005100563322 A CN A2005100563322A CN 200510056332 A CN200510056332 A CN 200510056332A CN 1680313 A CN1680313 A CN 1680313A
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- 239000003528 protein farnesyltransferase inhibitor Substances 0.000 title description 6
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 154
- 238000000034 method Methods 0.000 abstract description 44
- 206010028980 Neoplasm Diseases 0.000 abstract description 16
- 201000011510 cancer Diseases 0.000 abstract description 12
- 230000006126 farnesylation Effects 0.000 abstract description 12
- 201000010099 disease Diseases 0.000 abstract description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 8
- 102000004190 Enzymes Human genes 0.000 abstract description 4
- 108090000790 Enzymes Proteins 0.000 abstract description 4
- 102000004357 Transferases Human genes 0.000 abstract description 4
- 108090000992 Transferases Proteins 0.000 abstract description 4
- 108090000623 proteins and genes Proteins 0.000 abstract description 4
- 230000005764 inhibitory process Effects 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 230000001404 mediated effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- -1 heterocyclic radical Chemical class 0.000 description 63
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
- 238000002360 preparation method Methods 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
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- 239000000243 solution Substances 0.000 description 15
- 238000011282 treatment Methods 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 13
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical group [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 230000008859 change Effects 0.000 description 7
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- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 6
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- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 5
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 5
- 229940124226 Farnesyltransferase inhibitor Drugs 0.000 description 5
- 108090000723 Insulin-Like Growth Factor I Proteins 0.000 description 5
- 239000005642 Oleic acid Substances 0.000 description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
- 102000013275 Somatomedins Human genes 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 5
- 150000002632 lipids Chemical class 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 5
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
- 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 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
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- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
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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
- C07D401/12—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
-
- 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
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| GBGB9930318.2A GB9930318D0 (en) | 1999-12-22 | 1999-12-22 | Novel compounds |
| GB9930318.2 | 1999-12-22 |
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| CNB008174202A Division CN1229344C (zh) | 1999-12-22 | 2000-12-18 | 法尼基转移酶抑制剂 |
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| CNA2005100563322A Pending CN1680313A (zh) | 1999-12-22 | 2000-12-18 | 法尼基转移酶抑制剂 |
| CNB008174202A Expired - Fee Related CN1229344C (zh) | 1999-12-22 | 2000-12-18 | 法尼基转移酶抑制剂 |
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| CNB008174202A Expired - Fee Related CN1229344C (zh) | 1999-12-22 | 2000-12-18 | 法尼基转移酶抑制剂 |
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| US (1) | US7101897B2 (https=) |
| EP (1) | EP1255733B1 (https=) |
| JP (1) | JP3742593B2 (https=) |
| KR (1) | KR20020063251A (https=) |
| CN (2) | CN1680313A (https=) |
| AR (1) | AR029460A1 (https=) |
| AT (1) | ATE316074T1 (https=) |
| AU (1) | AU776003B2 (https=) |
| BR (1) | BR0016669A (https=) |
| CA (1) | CA2387579A1 (https=) |
| CO (1) | CO5360641A1 (https=) |
| CZ (1) | CZ20022125A3 (https=) |
| DE (1) | DE60025650D1 (https=) |
| EE (1) | EE200200206A (https=) |
| GB (1) | GB9930318D0 (https=) |
| HU (1) | HUP0204135A3 (https=) |
| IL (1) | IL149871A0 (https=) |
| IS (1) | IS6358A (https=) |
| MX (1) | MXPA02005981A (https=) |
| MY (1) | MY133606A (https=) |
| NO (1) | NO20022924L (https=) |
| NZ (1) | NZ518341A (https=) |
| PL (1) | PL355887A1 (https=) |
| RU (1) | RU2259997C2 (https=) |
| SK (1) | SK8642002A3 (https=) |
| WO (1) | WO2001046137A1 (https=) |
| ZA (1) | ZA200202694B (https=) |
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| WO2005117864A1 (en) * | 2004-05-28 | 2005-12-15 | Astrazeneca Ab | Combination product comprising anastrozole and a dual prenyl transferase inhibitor |
| JP4880473B2 (ja) * | 2004-10-08 | 2012-02-22 | 壽製薬株式会社 | ホスホン酸誘導体及び血中の高リン酸が関与する疾患の治療剤 |
| WO2007092285A2 (en) * | 2006-02-02 | 2007-08-16 | Link Medicine Corporation | Treatment of synucleinopathies |
| WO2009151683A2 (en) | 2008-03-12 | 2009-12-17 | Link Medicine Corporation | Quinolinone farnesyl transferase inhibitors for the treatment of synucleinopathies and other indications |
| JP2012508768A (ja) | 2008-11-13 | 2012-04-12 | リンク・メディスン・コーポレーション | アザキノリノン誘導体及びその使用 |
| WO2010107739A2 (en) | 2009-03-18 | 2010-09-23 | The Board Of Trustees Of The Leland Stanford Junior University | Methods and compositions of treating a flaviviridae family viral infection |
| WO2011088126A2 (en) * | 2010-01-13 | 2011-07-21 | Eiger Biopharmaceuticals, Inc. | Treatment of viral infection with prenyltransferase inhibitors |
| WO2018132791A1 (en) | 2017-01-16 | 2018-07-19 | The Regents Of The University Of California | Treatment of neurodegenerative conditions by disruption of rhes |
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| SU422723A1 (ru) * | 1972-03-29 | 1974-04-05 | Б. В. Салов, Т. А. Губенкова , И. В. Быховска | Способ получения 5-нитро-2-аминобензойнойкислоты |
| CA1283906C (en) | 1983-05-09 | 1991-05-07 | Makoto Sunagawa | .beta.-LACTAM COMPOUNDS AND PRODUCTION THEREOF |
| JPS60233076A (ja) | 1984-05-03 | 1985-11-19 | Sumitomo Chem Co Ltd | 新規なβ−ラクタム化合物およびその製造法 |
| EP0182213B1 (en) | 1984-11-08 | 1990-09-26 | Sumitomo Pharmaceuticals Company, Limited | Carbapenem compounds and production thereof |
| KR880006244A (ko) | 1986-11-24 | 1988-07-22 | 후지사와 도모 기찌 로 | 3-피롤리디닐티오-1-아자바이스클로[3.2.0]햅트2-엔-2-카르복실산 화합물 및 이의 제조방법 |
| GB8921635D0 (en) | 1989-09-25 | 1989-11-08 | Fujisawa Pharmaceutical Co | 3-pyrrolidinylthio-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid derivatives |
| CA2036163C (en) | 1990-02-14 | 2001-06-19 | Makoto Sunagawa | Novel beta-lactam compounds and their production |
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-
1999
- 1999-12-22 GB GBGB9930318.2A patent/GB9930318D0/en not_active Ceased
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2000
- 2000-12-18 CN CNA2005100563322A patent/CN1680313A/zh active Pending
- 2000-12-18 EP EP00985605A patent/EP1255733B1/en not_active Expired - Lifetime
- 2000-12-18 CA CA002387579A patent/CA2387579A1/en not_active Abandoned
- 2000-12-18 EE EEP200200206A patent/EE200200206A/xx unknown
- 2000-12-18 KR KR1020027008034A patent/KR20020063251A/ko not_active Ceased
- 2000-12-18 RU RU2002119405/04A patent/RU2259997C2/ru not_active IP Right Cessation
- 2000-12-18 CN CNB008174202A patent/CN1229344C/zh not_active Expired - Fee Related
- 2000-12-18 HU HU0204135A patent/HUP0204135A3/hu unknown
- 2000-12-18 BR BR0016669-3A patent/BR0016669A/pt not_active IP Right Cessation
- 2000-12-18 PL PL00355887A patent/PL355887A1/xx not_active Application Discontinuation
- 2000-12-18 WO PCT/GB2000/004856 patent/WO2001046137A1/en not_active Ceased
- 2000-12-18 AT AT00985605T patent/ATE316074T1/de not_active IP Right Cessation
- 2000-12-18 DE DE60025650T patent/DE60025650D1/de not_active Expired - Lifetime
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- 2000-12-21 AR ARP000106845A patent/AR029460A1/es not_active Application Discontinuation
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