NZ521032A - 4-amino-5-cyano-2-anilino-pyrimidine derivatives and their use as pharmaceutical composiitons for cancer - Google Patents
4-amino-5-cyano-2-anilino-pyrimidine derivatives and their use as pharmaceutical composiitons for cancerInfo
- Publication number
- NZ521032A NZ521032A NZ521032A NZ52103201A NZ521032A NZ 521032 A NZ521032 A NZ 521032A NZ 521032 A NZ521032 A NZ 521032A NZ 52103201 A NZ52103201 A NZ 52103201A NZ 521032 A NZ521032 A NZ 521032A
- Authority
- NZ
- New Zealand
- Prior art keywords
- sulphamoyl
- formula
- compound
- amino
- 6alkyl
- Prior art date
Links
- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 25
- 201000011510 cancer Diseases 0.000 title description 4
- RKWMXFMTFOSKMW-UHFFFAOYSA-N 4-amino-2-anilinopyrimidine-5-carbonitrile Chemical class C1=C(C#N)C(N)=NC(NC=2C=CC=CC=2)=N1 RKWMXFMTFOSKMW-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 128
- -1 nitro, cyano, hydroxy, amino, carboxy, carbamoyl Chemical group 0.000 claims abstract description 115
- 150000002148 esters Chemical class 0.000 claims abstract description 51
- 150000003839 salts Chemical class 0.000 claims abstract description 47
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 32
- 238000011282 treatment Methods 0.000 claims abstract description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 22
- 230000000694 effects Effects 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 20
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 19
- 230000022131 cell cycle Effects 0.000 claims abstract description 17
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 16
- 239000003814 drug Substances 0.000 claims abstract description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 10
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims abstract description 5
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
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- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims abstract description 4
- GSNMXUBZXPYQQE-UHFFFAOYSA-N 4-amino-2-(2,4-dimethylanilino)pyrimidine-5-carbonitrile Chemical compound CC1=CC(C)=CC=C1NC1=NC=C(C#N)C(N)=N1 GSNMXUBZXPYQQE-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 5
- YHHJWBDAGVDXLS-UHFFFAOYSA-N 2-hydroxyethyl 2-[(4-amino-5-cyanopyrimidin-2-yl)amino]benzoate Chemical compound C1=C(C#N)C(N)=NC(NC=2C(=CC=CC=2)C(=O)OCCO)=N1 YHHJWBDAGVDXLS-UHFFFAOYSA-N 0.000 claims abstract 2
- QCSKBYGDMGDAGR-UHFFFAOYSA-N methyl 2-[(4-amino-5-cyanopyrimidin-2-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC1=NC=C(C#N)C(N)=N1 QCSKBYGDMGDAGR-UHFFFAOYSA-N 0.000 claims abstract 2
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- 238000001727 in vivo Methods 0.000 claims description 45
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 18
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- 229940068918 polyethylene glycol 400 Drugs 0.000 claims 2
- 239000001488 sodium phosphate Substances 0.000 claims 2
- 229910000162 sodium phosphate Inorganic materials 0.000 claims 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 7
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- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
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- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- 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
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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Landscapes
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| US6939874B2 (en) | 2001-08-22 | 2005-09-06 | Amgen Inc. | Substituted pyrimidinyl derivatives and methods of use |
| US7115617B2 (en) | 2001-08-22 | 2006-10-03 | Amgen Inc. | Amino-substituted pyrimidinyl derivatives and methods of use |
| CA2463989C (en) | 2001-10-17 | 2012-01-31 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Pyrimidine derivatives, pharmaceutical compositions containing these compounds, the use thereof and process for the preparation thereof |
| WO2003062246A1 (en) * | 2002-01-22 | 2003-07-31 | Warner-Lambert Company Llc | 2-thia-1,6,8-triaza-naphtalene-2,2-dioxides as cdk inhibitors |
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| RS20050363A (sr) * | 2002-11-28 | 2007-11-15 | Schering Aktiengesellschaft, | Chk-,Pdk- I Akt-INHIBITORNI PIRIMIDINI, NJIHOVA PROIZVODNJA I UPOTREBA KAO FARMACEUTSKIH SREDSTAVA |
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| US20050171182A1 (en) * | 2003-12-11 | 2005-08-04 | Roger Briesewitz | Methods and compositions for use in the treatment of mutant receptor tyrosine kinase driven cellular proliferative diseases |
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| BRPI0517426A (pt) * | 2004-12-17 | 2008-10-07 | Astrazeneca Ab | composto, processo para preparar o mesmo, composição farmacêutica, uso de um composto, e, métodos para produzir um efeito anti-proliferação celular, para produzir um efeito inibitório de cdk2, e para tratar uma doença em um animal de sangue quente |
| MX2008001428A (es) * | 2005-07-30 | 2008-04-04 | Astrazeneca Ab | Compuestos de imidazolil-pirimidina para uso en el tratamiento de trastornos proliferativos. |
| CA2623374A1 (en) | 2005-09-30 | 2007-04-05 | Astrazeneca Ab | Imidazo [1,2-a] pyridine having anti-cell-proliferation activity |
| US7713987B2 (en) | 2005-12-06 | 2010-05-11 | Rigel Pharmaceuticals, Inc. | Pyrimidine-2,4-diamines and their uses |
| US8623887B2 (en) | 2006-05-15 | 2014-01-07 | Boehringer Ingelheim International Gmbh | Compounds |
| TW200811169A (en) * | 2006-05-26 | 2008-03-01 | Astrazeneca Ab | Chemical compounds |
| EP2231656A1 (en) | 2007-12-19 | 2010-09-29 | Amgen Inc. | Fused pyridine, pyrimidine and triazine compounds as cell cycle inhibitors |
| ATE531372T1 (de) | 2008-04-07 | 2011-11-15 | Amgen Inc | Gem-disubstituierte und spirocyclische aminopyridine/pyrimidine als zellcyclus- inhibitoren |
| US9376664B2 (en) | 2010-06-14 | 2016-06-28 | The Scripps Research Institute | Reprogramming of cells to a new fate |
| ES2543569T3 (es) | 2011-03-23 | 2015-08-20 | Amgen Inc. | Inhibidores duales tricíclicos condensados de CDK 4/6 y FLT3 |
| CN111683976B (zh) | 2018-02-05 | 2022-11-18 | 生物辐射实验室股份有限公司 | 具有阴离子交换-疏水混合模式配体的色谱树脂 |
| CN111686113B (zh) * | 2019-03-15 | 2022-12-30 | 北京大学 | Sonic Hedgehog抑制剂及应用 |
| CN112110863A (zh) * | 2020-08-27 | 2020-12-22 | 中山大学 | 一种磺酰氟类化合物、其制备方法以及通过其制备磺酰胺类化合物的方法 |
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-
2000
- 2000-03-28 GB GBGB0007371.8A patent/GB0007371D0/en not_active Ceased
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2001
- 2001-03-23 CN CNB018071570A patent/CN1231471C/zh not_active Expired - Fee Related
- 2001-03-23 US US10/239,790 patent/US6906065B2/en not_active Expired - Fee Related
- 2001-03-23 PT PT01914026T patent/PT1268445E/pt unknown
- 2001-03-23 IL IL15139201A patent/IL151392A0/xx active IP Right Grant
- 2001-03-23 AU AU3941401A patent/AU3941401A/xx active Pending
- 2001-03-23 DE DE60113080T patent/DE60113080T2/de not_active Expired - Fee Related
- 2001-03-23 AU AU2001239414A patent/AU2001239414B2/en not_active Ceased
- 2001-03-23 JP JP2001570630A patent/JP2003528861A/ja active Pending
- 2001-03-23 KR KR1020027012916A patent/KR100802367B1/ko not_active Expired - Fee Related
- 2001-03-23 BR BR0109577-3A patent/BR0109577A/pt not_active Application Discontinuation
- 2001-03-23 EP EP01914026A patent/EP1268445B1/en not_active Expired - Lifetime
- 2001-03-23 CA CA002399864A patent/CA2399864A1/en not_active Abandoned
- 2001-03-23 DK DK01914026T patent/DK1268445T3/da active
- 2001-03-23 MX MXPA02009255A patent/MXPA02009255A/es active IP Right Grant
- 2001-03-23 NZ NZ521032A patent/NZ521032A/en unknown
- 2001-03-23 WO PCT/GB2001/001264 patent/WO2001072717A1/en not_active Ceased
- 2001-03-23 ES ES01914026T patent/ES2247078T3/es not_active Expired - Lifetime
- 2001-03-23 AT AT01914026T patent/ATE303366T1/de not_active IP Right Cessation
- 2001-03-27 MY MYPI20011414A patent/MY124527A/en unknown
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- 2002-08-21 IL IL151392A patent/IL151392A/en not_active IP Right Cessation
- 2002-08-29 ZA ZA200206957A patent/ZA200206957B/en unknown
- 2002-09-27 NO NO20024644A patent/NO324228B1/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE60113080D1 (de) | 2005-10-06 |
| ES2247078T3 (es) | 2006-03-01 |
| MXPA02009255A (es) | 2003-03-12 |
| NO20024644L (no) | 2002-11-27 |
| EP1268445B1 (en) | 2005-08-31 |
| KR20020083532A (ko) | 2002-11-02 |
| ZA200206957B (en) | 2003-12-01 |
| AU3941401A (en) | 2001-10-08 |
| MY124527A (en) | 2006-06-30 |
| DE60113080T2 (de) | 2006-05-18 |
| US6906065B2 (en) | 2005-06-14 |
| JP2003528861A (ja) | 2003-09-30 |
| WO2001072717A1 (en) | 2001-10-04 |
| KR100802367B1 (ko) | 2008-02-13 |
| NO20024644D0 (no) | 2002-09-27 |
| AU2001239414B2 (en) | 2004-09-02 |
| DK1268445T3 (da) | 2005-11-07 |
| ATE303366T1 (de) | 2005-09-15 |
| GB0007371D0 (en) | 2000-05-17 |
| CN1419548A (zh) | 2003-05-21 |
| CA2399864A1 (en) | 2001-10-04 |
| CN1231471C (zh) | 2005-12-14 |
| BR0109577A (pt) | 2003-01-28 |
| US20030087923A1 (en) | 2003-05-08 |
| IL151392A0 (en) | 2003-04-10 |
| EP1268445A1 (en) | 2003-01-02 |
| PT1268445E (pt) | 2005-11-30 |
| NO324228B1 (no) | 2007-09-10 |
| IL151392A (en) | 2007-06-17 |
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