ES2298798T3 - Imidazopirimidinas sustituidas para la prevencion y el tratamiento del cancer. - Google Patents
Imidazopirimidinas sustituidas para la prevencion y el tratamiento del cancer. Download PDFInfo
- Publication number
- ES2298798T3 ES2298798T3 ES04763583T ES04763583T ES2298798T3 ES 2298798 T3 ES2298798 T3 ES 2298798T3 ES 04763583 T ES04763583 T ES 04763583T ES 04763583 T ES04763583 T ES 04763583T ES 2298798 T3 ES2298798 T3 ES 2298798T3
- Authority
- ES
- Spain
- Prior art keywords
- pyrimidine
- methylsulfanylphenyl
- imidazo
- alkyl
- methoxyphenyl
- 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 - Lifetime
Links
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- 239000000203 mixture Substances 0.000 claims description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
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- QNEGJEZWIOXARM-UHFFFAOYSA-N 2-(4-bromophenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=CC(Br)=CC=2)N=C2N1C=CC=N2 QNEGJEZWIOXARM-UHFFFAOYSA-N 0.000 claims description 2
- MKOZDXHSRDZEPA-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-(3-methyl-4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(C)C(SC)=CC=2)N2C=CC=NC2=N1 MKOZDXHSRDZEPA-UHFFFAOYSA-N 0.000 claims description 2
- BNIUKULMJGZVCF-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC=NC2=N1 BNIUKULMJGZVCF-UHFFFAOYSA-N 0.000 claims description 2
- CQGADDAMYKKHBF-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-(4-propan-2-ylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC(C)C)=CC=2)N2C=CC=NC2=N1 CQGADDAMYKKHBF-UHFFFAOYSA-N 0.000 claims description 2
- JKDLHBFPHMCREW-UHFFFAOYSA-N 2-(4-methoxyphenyl)-7-methyl-3-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(SC)=CC=2)N2C=CC(C)=NC2=N1 JKDLHBFPHMCREW-UHFFFAOYSA-N 0.000 claims description 2
- XMIGNTPKVGZDLI-UHFFFAOYSA-N 3-(3-bromo-4-methylsulfanylphenyl)-2-(3-methylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Br)C(SC)=CC=C1C1=C(C=2C=C(C)C=CC=2)N=C2N1C=CC=N2 XMIGNTPKVGZDLI-UHFFFAOYSA-N 0.000 claims description 2
- NWHHTSQOKQTUBY-UHFFFAOYSA-N 3-(3-bromo-4-methylsulfanylphenyl)-2-(4-chlorophenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Br)C(SC)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)N=C2N1C=CC=N2 NWHHTSQOKQTUBY-UHFFFAOYSA-N 0.000 claims description 2
- CMDHZEHXDUCYLT-UHFFFAOYSA-N 3-(3-chloro-4-methylsulfanylphenyl)-2-(4-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Cl)C(SC)=CC=2)N2C=CC(C)=NC2=N1 CMDHZEHXDUCYLT-UHFFFAOYSA-N 0.000 claims description 2
- IRMVAYWYPYRLQU-UHFFFAOYSA-N 3-(3-chloro-4-methylsulfanylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Cl)C(SC)=CC=2)N2C=CC=NC2=N1 IRMVAYWYPYRLQU-UHFFFAOYSA-N 0.000 claims description 2
- YXZQHTDRNOAXGO-UHFFFAOYSA-N 3-(3-chloro-4-methylsulfanylphenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(Cl)C(SC)=CC=2)N2C=CC=NC2=N1 YXZQHTDRNOAXGO-UHFFFAOYSA-N 0.000 claims description 2
- HGHKJDLMPVJKEP-UHFFFAOYSA-N 3-(3-chloro-4-methylsulfinylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=C(Cl)C(=CC=2)S(C)=O)N2C=CC=NC2=N1 HGHKJDLMPVJKEP-UHFFFAOYSA-N 0.000 claims description 2
- VZVRDRXCBUFAEG-UHFFFAOYSA-N 3-(3-chloro-4-propan-2-ylsulfanylphenyl)-2-(4-methylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(SC(C)C)=CC=C1C1=C(C=2C=CC(C)=CC=2)N=C2N1C=CC=N2 VZVRDRXCBUFAEG-UHFFFAOYSA-N 0.000 claims description 2
- JEVNUDGHTSWDIL-UHFFFAOYSA-N 3-(3-chloro-4-propan-2-ylsulfanylphenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(Cl)C(SC(C)C)=CC=2)N2C=CC=NC2=N1 JEVNUDGHTSWDIL-UHFFFAOYSA-N 0.000 claims description 2
- WQBLNMCUYHVYKT-UHFFFAOYSA-N 3-(3-chloro-4-propylsulfanylphenyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=C(Cl)C(SCCC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)N=C2N1C=CC=N2 WQBLNMCUYHVYKT-UHFFFAOYSA-N 0.000 claims description 2
- IKTHOCNOZUJIQV-UHFFFAOYSA-N 3-(3-methyl-4-methylsulfanylphenyl)-2-(4-methylsulfanylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(SC)=CC=C1C1=C(C=2C=C(C)C(SC)=CC=2)N2C=CC=NC2=N1 IKTHOCNOZUJIQV-UHFFFAOYSA-N 0.000 claims description 2
- MTHXCZAWVDJHQH-UHFFFAOYSA-N 7-methyl-3-(4-methylphenyl)-2-(4-methylsulfonylphenyl)imidazo[1,2-a]pyrimidine Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC(=CC=2)S(C)(=O)=O)N=C2N1C=CC(C)=N2 MTHXCZAWVDJHQH-UHFFFAOYSA-N 0.000 claims description 2
- 101100162200 Aspergillus parasiticus (strain ATCC 56775 / NRRL 5862 / SRRC 143 / SU-1) aflD gene Proteins 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P13/10—Drugs for disorders of the urinary system of the bladder
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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Landscapes
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
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- Veterinary Medicine (AREA)
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- Pharmacology & Pharmacy (AREA)
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- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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| WO2007096764A2 (en) * | 2006-02-27 | 2007-08-30 | Glenmark Pharmaceuticals S.A. | Bicyclic heteroaryl derivatives as cannabinoid receptor modulators |
| TW200817410A (en) | 2006-08-07 | 2008-04-16 | Incyte Corp | Triazolotriazines as kinase inhibitors |
| EP2497470B8 (en) | 2006-11-22 | 2015-12-02 | Incyte Holdings Corporation | Imidazotriazines and imidazopyrimidines as kinase inhibitors |
| PA8793301A1 (es) | 2007-08-14 | 2009-04-23 | Bayer Schering Pharma Ag | Imidazoles bicíclicos fusionados |
| EP2062893A1 (en) * | 2007-10-18 | 2009-05-27 | Bayer Schering Pharma AG | Fused imidazoles for cancer treatment |
| NZ589622A (en) | 2008-05-21 | 2012-10-26 | Incyte Corp | Salts of 2-fluoro-N-methyl-4-[7-(quinolin-6-yl-methyl)-imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide and processes related to preparing the same |
| NZ599289A (en) | 2009-10-16 | 2014-11-28 | Melinta Therapeutics Inc | Antimicrobial compounds and methods of making and using the same |
| KR101870878B1 (ko) | 2010-02-03 | 2018-06-25 | 인사이트 홀딩스 코포레이션 | Ｃ―ＭＥＴ 억제제로서의 이미다조〔１，２―ｂ〕〔１，２，４〕트리아진 |
| US8410117B2 (en) * | 2010-03-26 | 2013-04-02 | Hoffmann-La Roche Inc. | Imidazopyrimidine derivatives |
| AU2012238589B2 (en) | 2011-04-07 | 2017-02-16 | Bayer Intellectual Property Gmbh | Imidazopyridazines as Akt kinase inhibitors |
| CN102796103A (zh) * | 2011-05-23 | 2012-11-28 | 南京英派药业有限公司 | 6-（芳基甲酰）咪唑并[1,2-a]嘧啶和6-（芳基甲酰）[1,2,4]三唑并[4,3-a]嘧啶作为Hedgehog抑制剂及其应用 |
| US9186361B2 (en) | 2013-03-15 | 2015-11-17 | Novartis Ag | Compounds and compositions for the treatment of parasitic diseases |
| UY35400A (es) * | 2013-03-15 | 2014-10-31 | Novartis Ag | Compuestos y composiciones para el tratamiento de enfermedades parasitarias |
| US9296754B2 (en) | 2013-03-15 | 2016-03-29 | Novartis Ag | Compounds and compositions for the treatment of parasitic diseases |
| WO2014151630A2 (en) | 2013-03-15 | 2014-09-25 | Irm Llc | Compounds and compositions for the treatment of parasitic diseases |
| PE20160865A1 (es) | 2013-12-19 | 2016-09-03 | Novartis Ag | Derivados de [1,2,4] triazolo [1,5-a]pirimidina como inhibidores de proteasoma para el tratamiento de enfermedades parasitarias tales como leishmaniasis |
| JP2018507881A (ja) | 2015-03-11 | 2018-03-22 | メリンタ セラピューティクス，インコーポレイテッド | 抗微生物化合物ならびにこれらを作製および使用する方法 |
| CA3023317A1 (en) | 2016-05-06 | 2017-11-09 | Melinta Therapeutics, Inc. | Antimicrobials and methods of making and using same |
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| US3455924A (en) * | 1967-02-08 | 1969-07-15 | Upjohn Co | Dianisylimidazoles |
| US5700826A (en) * | 1995-06-07 | 1997-12-23 | Ontogen Corporation | 1,2,4,5-tetra substituted imidazoles as modulators of multi-drug resistance |
| ES2140354B1 (es) * | 1998-08-03 | 2000-11-01 | S A L V A T Lab Sa | Imidazo (1,2a) azinas sustituidas como inhibidores selectivos de la cox-2. |
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2004
- 2004-07-29 KR KR1020067001923A patent/KR20060034303A/ko not_active Withdrawn
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- 2004-07-29 ZA ZA200601706A patent/ZA200601706B/en unknown
- 2004-07-29 AT AT04763583T patent/ATE380816T1/de not_active IP Right Cessation
- 2004-07-29 CN CNA2004800279669A patent/CN1860121A/zh active Pending
- 2004-07-29 AU AU2004263297A patent/AU2004263297A1/en not_active Abandoned
- 2004-07-29 EA EA200600330A patent/EA009038B1/ru not_active IP Right Cessation
- 2004-07-29 ES ES04763583T patent/ES2298798T3/es not_active Expired - Lifetime
- 2004-07-29 WO PCT/EP2004/008476 patent/WO2005014598A1/en not_active Ceased
-
2006
- 2006-01-27 US US11/340,856 patent/US20060189631A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2004263297A1 (en) | 2005-02-17 |
| CA2534292A1 (en) | 2005-02-17 |
| JP2007500160A (ja) | 2007-01-11 |
| ATE380816T1 (de) | 2007-12-15 |
| DE602004010680D1 (de) | 2008-01-24 |
| DE602004010680T2 (de) | 2009-01-02 |
| EA009038B1 (ru) | 2007-10-26 |
| EP1660500B1 (en) | 2007-12-12 |
| ZA200601706B (en) | 2007-09-26 |
| KR20060034303A (ko) | 2006-04-21 |
| CN1860121A (zh) | 2006-11-08 |
| EA200600330A1 (ru) | 2006-08-25 |
| US20060189631A1 (en) | 2006-08-24 |
| EP1660500A1 (en) | 2006-05-31 |
| WO2005014598A1 (en) | 2005-02-17 |
| BRPI0412636A (pt) | 2006-09-26 |
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