JP2007506745A5 - - Google Patents
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- Publication number
- JP2007506745A5 JP2007506745A5 JP2006528080A JP2006528080A JP2007506745A5 JP 2007506745 A5 JP2007506745 A5 JP 2007506745A5 JP 2006528080 A JP2006528080 A JP 2006528080A JP 2006528080 A JP2006528080 A JP 2006528080A JP 2007506745 A5 JP2007506745 A5 JP 2007506745A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- alkyl
- compound
- pharmaceutically acceptable
- acceptable salt
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 44
- 150000003839 salts Chemical class 0.000 claims 34
- 229910052739 hydrogen Inorganic materials 0.000 claims 32
- 239000008194 pharmaceutical composition Substances 0.000 claims 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 22
- 229910052799 carbon Inorganic materials 0.000 claims 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 15
- 125000004430 oxygen atom Chemical group O* 0.000 claims 14
- 125000004434 sulfur atom Chemical group 0.000 claims 14
- 125000000623 heterocyclic group Chemical group 0.000 claims 13
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 238000000034 method Methods 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- 102000004243 Tubulin Human genes 0.000 claims 6
- 108090000704 Tubulin Proteins 0.000 claims 6
- 230000036457 multidrug resistance Effects 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 239000002585 base Substances 0.000 claims 4
- 230000005764 inhibitory process Effects 0.000 claims 4
- 239000000010 aprotic solvent Substances 0.000 claims 3
- MQLACMBJVPINKE-UHFFFAOYSA-N 10-[(3-hydroxy-4-methoxyphenyl)methylidene]anthracen-9-one Chemical compound C1=C(O)C(OC)=CC=C1C=C1C2=CC=CC=C2C(=O)C2=CC=CC=C21 MQLACMBJVPINKE-UHFFFAOYSA-N 0.000 claims 2
- DEPDDPLQZYCHOH-UHFFFAOYSA-N 1h-imidazol-2-amine Chemical compound NC1=NC=CN1 DEPDDPLQZYCHOH-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 2
- 150000008044 alkali metal hydroxides Chemical group 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 229940127089 cytotoxic agent Drugs 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 230000008029 eradication Effects 0.000 claims 2
- 150000004678 hydrides Chemical class 0.000 claims 2
- KKIKVDAHSKZQLB-UHFFFAOYSA-N imidazo[1,2-a]pyrimidin-5-amine Chemical compound NC1=CC=NC2=NC=CN12 KKIKVDAHSKZQLB-UHFFFAOYSA-N 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 230000001737 promoting effect Effects 0.000 claims 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 210000004881 tumor cell Anatomy 0.000 claims 2
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims 1
- ZMCMEOGWUXEBKP-UHFFFAOYSA-N 3-[4-(7-chloro-5-cycloheptylimidazo[1,2-a]pyrimidin-6-yl)-3,5-difluorophenoxy]-n,n-dimethylpropan-1-amine Chemical compound FC1=CC(OCCCN(C)C)=CC(F)=C1C1=C(C2CCCCCC2)N2C=CN=C2N=C1Cl ZMCMEOGWUXEBKP-UHFFFAOYSA-N 0.000 claims 1
- DJMBTNBNXQKLRN-UHFFFAOYSA-N 3-[4-(7-chloro-5-cyclohexylimidazo[1,2-a]pyrimidin-6-yl)-3,5-difluorophenoxy]-n,n-dimethylpropan-1-amine Chemical compound FC1=CC(OCCCN(C)C)=CC(F)=C1C1=C(C2CCCCC2)N2C=CN=C2N=C1Cl DJMBTNBNXQKLRN-UHFFFAOYSA-N 0.000 claims 1
- TURWXBQPPKQQIC-UHFFFAOYSA-N 4-[4-(4-oxobutylamino)butylamino]butanal Chemical compound O=CCCCNCCCCNCCCC=O TURWXBQPPKQQIC-UHFFFAOYSA-N 0.000 claims 1
- FZGFZAGRFCMQDD-UHFFFAOYSA-N 5-(azepan-1-yl)-7-chloro-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidine Chemical compound FC1=CC(F)=CC(F)=C1C1=C(N2CCCCCC2)N2C=CN=C2N=C1Cl FZGFZAGRFCMQDD-UHFFFAOYSA-N 0.000 claims 1
- NVKCYJNBXGAKLO-UHFFFAOYSA-N 7-chloro-5-piperidin-1-yl-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidine Chemical compound FC1=CC(F)=CC(F)=C1C1=C(N2CCCCC2)N2C=CN=C2N=C1Cl NVKCYJNBXGAKLO-UHFFFAOYSA-N 0.000 claims 1
- HIGJGYJOEUKNQY-UHFFFAOYSA-N 7-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-(1,1,1-trifluoropropan-2-yl)imidazo[1,2-a]pyrimidin-5-amine Chemical compound FC1=CC(OCCCNC)=CC(F)=C1C1=C(NC(C)C(F)(F)F)N2C=CN=C2N=C1Cl HIGJGYJOEUKNQY-UHFFFAOYSA-N 0.000 claims 1
- HIGJGYJOEUKNQY-SNVBAGLBSA-N 7-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]imidazo[1,2-a]pyrimidin-5-amine Chemical compound FC1=CC(OCCCNC)=CC(F)=C1C1=C(N[C@H](C)C(F)(F)F)N2C=CN=C2N=C1Cl HIGJGYJOEUKNQY-SNVBAGLBSA-N 0.000 claims 1
- HIGJGYJOEUKNQY-JTQLQIEISA-N 7-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]imidazo[1,2-a]pyrimidin-5-amine Chemical compound FC1=CC(OCCCNC)=CC(F)=C1C1=C(N[C@@H](C)C(F)(F)F)N2C=CN=C2N=C1Cl HIGJGYJOEUKNQY-JTQLQIEISA-N 0.000 claims 1
- GBQJEIAOWXKFIB-UHFFFAOYSA-N 7-chloro-6-[4-[3-(dimethylamino)propoxy]-2,6-difluorophenyl]-n-(1,1,1-trifluoropropan-2-yl)imidazo[1,2-a]pyrimidin-5-amine Chemical compound ClC1=NC2=NC=CN2C(NC(C)C(F)(F)F)=C1C1=C(F)C=C(OCCCN(C)C)C=C1F GBQJEIAOWXKFIB-UHFFFAOYSA-N 0.000 claims 1
- IARMANWKDIPJME-UHFFFAOYSA-N 7-chloro-6-[4-[3-(dimethylamino)propoxy]-2,6-difluorophenyl]-n-(2,2,2-trifluoroethyl)imidazo[1,2-a]pyrimidin-5-amine Chemical compound FC1=CC(OCCCN(C)C)=CC(F)=C1C1=C(NCC(F)(F)F)N2C=CN=C2N=C1Cl IARMANWKDIPJME-UHFFFAOYSA-N 0.000 claims 1
- GREIJPFDYMJIAK-UHFFFAOYSA-N 7-chloro-6-[4-[4-(dimethylamino)butoxy]-2,6-difluorophenyl]-n-(2,2,2-trifluoroethyl)imidazo[1,2-a]pyrimidin-5-amine Chemical compound FC1=CC(OCCCCN(C)C)=CC(F)=C1C1=C(NCC(F)(F)F)N2C=CN=C2N=C1Cl GREIJPFDYMJIAK-UHFFFAOYSA-N 0.000 claims 1
- FCECYJHHNWCQND-UHFFFAOYSA-N 7-chloro-n-(2,2,2-trifluoroethyl)-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidin-5-amine Chemical compound FC1=CC(F)=CC(F)=C1C1=C(NCC(F)(F)F)N2C=CN=C2N=C1Cl FCECYJHHNWCQND-UHFFFAOYSA-N 0.000 claims 1
- FAOGQCUBDDSLOY-UHFFFAOYSA-N C1(CCCCCC1)C1=C(C=NC=2N1C=CN2)C2=C(C=C(C=C2F)F)F Chemical compound C1(CCCCCC1)C1=C(C=NC=2N1C=CN2)C2=C(C=C(C=C2F)F)F FAOGQCUBDDSLOY-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 102000029749 Microtubule Human genes 0.000 claims 1
- 108091022875 Microtubule Proteins 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 230000012010 growth Effects 0.000 claims 1
- 210000004688 microtubule Anatomy 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000035755 proliferation Effects 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 230000004614 tumor growth Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50548603P | 2003-09-24 | 2003-09-24 | |
| US60/505,486 | 2003-09-24 | ||
| PCT/US2004/030595 WO2005030218A1 (en) | 2003-09-24 | 2004-09-17 | 6-aryl-7-halo-imidazo[1,2-a]pyrimidines as anticancer agent |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007506745A JP2007506745A (ja) | 2007-03-22 |
| JP2007506745A5 true JP2007506745A5 (https=) | 2007-10-25 |
| JP4695595B2 JP4695595B2 (ja) | 2011-06-08 |
Family
ID=34393021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006528080A Expired - Fee Related JP4695595B2 (ja) | 2003-09-24 | 2004-09-17 | 抗癌剤としての６−アリール−７−ハロ−イミダゾ［１，２−ａ］ピリミジン類 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US7285555B2 (https=) |
| EP (1) | EP1684763B1 (https=) |
| JP (1) | JP4695595B2 (https=) |
| CN (1) | CN100486580C (https=) |
| AT (1) | ATE398452T1 (https=) |
| AU (1) | AU2004275728A1 (https=) |
| BR (1) | BRPI0414778A (https=) |
| CA (1) | CA2537520A1 (https=) |
| DE (1) | DE602004014525D1 (https=) |
| DK (1) | DK1684763T3 (https=) |
| ES (1) | ES2308256T3 (https=) |
| MX (1) | MXPA06002939A (https=) |
| PL (1) | PL1684763T3 (https=) |
| WO (1) | WO2005030218A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2353593A1 (en) * | 1998-12-18 | 2000-06-22 | Hadasit Medical Research Services & Development Ltd. | Method of administering a compound to multi-drug resistant cells |
| SI2495016T1 (sl) | 2005-12-23 | 2020-04-30 | Ariad Pharmaceuticals, Inc. | Biciklične heteroarilne spojine |
| BRPI0807458A2 (pt) * | 2007-01-08 | 2014-06-03 | Basf Se | Uso de compostos, agente, semente, método para combater fungos nocivos fitopatogênicos, e, composto |
| CN107935870A (zh) * | 2017-11-09 | 2018-04-20 | 华中药业股份有限公司 | 一种2‑甲氨基‑5‑氯二苯甲酮的合成方法 |
Family Cites Families (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW224044B (https=) | 1991-12-30 | 1994-05-21 | Shell Internat Res Schappej B V | |
| US5593996A (en) * | 1991-12-30 | 1997-01-14 | American Cyanamid Company | Triazolopyrimidine derivatives |
| JP2794510B2 (ja) * | 1992-03-27 | 1998-09-10 | 富士写真フイルム株式会社 | ハロゲン化銀写真感光材料 |
| IL108747A (en) * | 1993-03-04 | 1999-03-12 | Shell Int Research | Mushroom-killing preparations containing a history of 6 metamorphoses of 5 - 7 Dihalo - 1, 2 - 4 Triazlo [A-1,5] Pyrimidine Certain such new compounds and their preparation |
| IL108731A (en) * | 1993-03-04 | 1997-03-18 | Shell Int Research | 6, N-DISUBSTITUTED-£1, 2, 4| TRIAZOLO-£1, 5-a| PYRIMIDINE- 7-AMINE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS FUNGICIDES |
| RU2147584C1 (ru) * | 1995-10-27 | 2000-04-20 | Американ Цианамид Компани | Способ получения дигалоидазолопиримидинов и способ получения дигидроксиазолопиримидинов |
| US5817663A (en) * | 1996-10-07 | 1998-10-06 | American Cyanamid Company | Pentafluorophenylazolopyrimidines |
| DK0984919T3 (da) | 1997-03-18 | 2003-05-12 | Basf Ag | Fremgangsmåde til fremstilling af arylmalonater |
| US5750766A (en) * | 1997-03-18 | 1998-05-12 | American Cyanamid Company | Process for the preparation of arylmalonates |
| US6255309B1 (en) * | 1999-03-19 | 2001-07-03 | American Cyanomid Co. | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| US6117876A (en) * | 1997-04-14 | 2000-09-12 | American Cyanamid Company | Fungicidal trifluorophenyl-triazolopyrimidines |
| TW460476B (en) | 1997-04-14 | 2001-10-21 | American Cyanamid Co | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| US5948783A (en) * | 1997-04-14 | 1999-09-07 | American Cyanamid Company | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| TWI252231B (en) | 1997-04-14 | 2006-04-01 | American Cyanamid Co | Fungicidal trifluorophenyl-triazolopyrimidines |
| US5994360A (en) * | 1997-07-14 | 1999-11-30 | American Cyanamid Company | Fungicidal 5-alkyl-triazolopyrimidines |
| US6020338A (en) * | 1998-02-11 | 2000-02-01 | American Cyanamid Company | Fungicidal 7-alkyl-triazolopyrimidines |
| HUP0100885A3 (en) | 1998-02-11 | 2002-12-28 | American Cyanamid Company Madi | Fungicidal 7-alkyl-triazolopyrimidines |
| US6124301A (en) * | 1998-03-17 | 2000-09-26 | American Cyanamid Company | Enhancement of the efficacy of triazolopyrimidines |
| JPH11322517A (ja) | 1998-03-17 | 1999-11-24 | American Cyanamid Co | トリアゾロピリミジン類の効力の増進 |
| AU752669B2 (en) | 1998-03-23 | 2002-09-26 | Basf Aktiengesellschaft | Fungicidal 6-(2-halo-4-alkoxyphenyl)-triazolopyrimidines |
| US5981534A (en) * | 1998-09-25 | 1999-11-09 | American Cyanamid Company | Fungicidal 6-(2,6-difluoro-4-alkoxyphenyl)-triazolopyrimidines |
| US6284762B1 (en) * | 1998-03-23 | 2001-09-04 | American Cyanamid Company | Fungicidal 6-(2-halo-4-alkoxyphenyl)-triazolopyrimidines |
| US6117865A (en) * | 1998-09-10 | 2000-09-12 | American Cyanamid Company | Fungicidal trifluorophenyl-triazolopyrimidines |
| US6268371B1 (en) * | 1998-09-10 | 2001-07-31 | American Cyanamid Co. | Fungicidal mixtures |
| ES2203021T3 (es) | 1998-09-25 | 2004-04-01 | Basf Aktiengesellschaft | Mezclas fungicidas. |
| US6242451B1 (en) * | 1998-09-25 | 2001-06-05 | Klaus-Juergen Pees | Fungicidal trihalophenyl-triazolopyrimidines |
| US5986135A (en) * | 1998-09-25 | 1999-11-16 | American Cyanamid Company | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| JP2002525291A (ja) | 1998-09-25 | 2002-08-13 | アメリカン サイアナミツド コンパニー | 非水性懸濁液濃縮物 |
| US6277856B1 (en) * | 1998-09-25 | 2001-08-21 | American Cynamid Co. | Fungicidal mixtures |
| US5985883A (en) * | 1998-09-25 | 1999-11-16 | American Cyanamid Company | Fungicidal trichlorophenyl-triazolopyrimidines |
| US6156925A (en) * | 1998-09-25 | 2000-12-05 | American Cyanamid Company | Process for the preparation of halogenated phenylmaloates |
| JP2000103790A (ja) | 1998-09-25 | 2000-04-11 | American Cyanamid Co | 殺菌・殺カビ性のトリハロフェニル―トリアゾロピリミジン類 |
| JP4025468B2 (ja) | 1999-07-29 | 2007-12-19 | 三井化学株式会社 | 有機電界発光素子 |
| WO2001035738A2 (en) | 1999-11-18 | 2001-05-25 | Basf Corporation | Non-aqueous concentrated spreading oil composition |
| US6559151B2 (en) * | 2000-05-08 | 2003-05-06 | Basf Aktiengesellschaft | 6-(2-trifluoromethyl-phenyl)-triazolopyrimidines |
| AU2001273062B2 (en) * | 2000-06-30 | 2005-11-24 | Wyeth | Substituted-triazolopyrimidines as anticancer agents |
| ES2223932T3 (es) * | 2000-08-25 | 2005-03-01 | Basf Aktiengesellschaft | Formulacion fungicida. |
| DE60013188T2 (de) | 2000-12-06 | 2004-12-30 | Basf Ag | Fungiizide 6-(trifluormethyl-phenyl)-triazolpyrimidine |
| WO2002067679A1 (en) | 2001-02-19 | 2002-09-06 | Basf Aktiengesellschaft | Fungicidal mixtures |
| CZ295558B6 (cs) | 2001-04-11 | 2005-08-17 | Basf Aktiengesellschaft | 5-Halogen-6-fenyl-7-fluoralkylamino-triazolopyrimidiny, způsob jejich přípravy a prostředek pro potírání fytopatogenních hub |
| ES2287312T3 (es) | 2001-09-04 | 2007-12-16 | Sumitomo Chemical Company, Limited | Imidazo(1,2-a)pirimidinas y composiciones fungicidas que las contienen. |
| WO2003089433A1 (en) * | 2002-04-19 | 2003-10-30 | Sumitomo Chemical Company, Limited | 5,6-DIPHENYLIMIDAZO[1,2-a]PYRIMIDINE AND BACTERICIDAL COMPOSITION CONTAINING THE SAME |
-
2004
- 2004-09-17 ES ES04784454T patent/ES2308256T3/es not_active Expired - Lifetime
- 2004-09-17 DK DK04784454T patent/DK1684763T3/da active
- 2004-09-17 CA CA002537520A patent/CA2537520A1/en not_active Abandoned
- 2004-09-17 DE DE602004014525T patent/DE602004014525D1/de not_active Expired - Lifetime
- 2004-09-17 PL PL04784454T patent/PL1684763T3/pl unknown
- 2004-09-17 EP EP04784454A patent/EP1684763B1/en not_active Expired - Lifetime
- 2004-09-17 MX MXPA06002939A patent/MXPA06002939A/es active IP Right Grant
- 2004-09-17 CN CNB2004800273126A patent/CN100486580C/zh not_active Expired - Fee Related
- 2004-09-17 WO PCT/US2004/030595 patent/WO2005030218A1/en not_active Ceased
- 2004-09-17 JP JP2006528080A patent/JP4695595B2/ja not_active Expired - Fee Related
- 2004-09-17 BR BRPI0414778-2A patent/BRPI0414778A/pt not_active IP Right Cessation
- 2004-09-17 AU AU2004275728A patent/AU2004275728A1/en not_active Withdrawn
- 2004-09-17 AT AT04784454T patent/ATE398452T1/de not_active IP Right Cessation
- 2004-09-24 US US10/950,542 patent/US7285555B2/en not_active Expired - Fee Related
-
2007
- 2007-09-19 US US11/903,100 patent/US7915266B2/en not_active Expired - Fee Related
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