CA2591321C - Phenylaminopyrimidine derivatives as inhibitors of bcr-abl kinase - Google Patents
Phenylaminopyrimidine derivatives as inhibitors of bcr-abl kinase Download PDFInfo
- Publication number
- CA2591321C CA2591321C CA2591321A CA2591321A CA2591321C CA 2591321 C CA2591321 C CA 2591321C CA 2591321 A CA2591321 A CA 2591321A CA 2591321 A CA2591321 A CA 2591321A CA 2591321 C CA2591321 C CA 2591321C
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- formula
- trifluoromethyl
- compound
- phenyl
- 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 - Fee Related
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- WEVYNIUIFUYDGI-UHFFFAOYSA-N 3-[6-[4-(trifluoromethoxy)anilino]-4-pyrimidinyl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=CN=C(NC=3C=CC(OC(F)(F)F)=CC=3)C=2)=C1 WEVYNIUIFUYDGI-UHFFFAOYSA-N 0.000 title claims description 11
- XGXNTJHZPBRBHJ-UHFFFAOYSA-N n-phenylpyrimidin-2-amine Chemical class N=1C=CC=NC=1NC1=CC=CC=C1 XGXNTJHZPBRBHJ-UHFFFAOYSA-N 0.000 title abstract description 11
- 108091000080 Phosphotransferase Proteins 0.000 title description 5
- 102000020233 phosphotransferase Human genes 0.000 title description 5
- 239000003112 inhibitor Substances 0.000 title description 3
- -1 Phenyl pyrimidine amine Chemical class 0.000 claims abstract description 131
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- 238000000034 method Methods 0.000 claims abstract description 49
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- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims abstract description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 142
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 87
- 235000002639 sodium chloride Nutrition 0.000 claims description 43
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 38
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 38
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- SIMLOQFADCPLAT-UHFFFAOYSA-N 4-phenylpyrido[3,2-d]pyrimidin-2-amine Chemical compound C=12N=CC=CC2=NC(N)=NC=1C1=CC=CC=C1 SIMLOQFADCPLAT-UHFFFAOYSA-N 0.000 claims description 14
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- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 9
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/66—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/18—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- 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
- C07D401/14—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 three or more hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN908/CHE/2004 | 2004-09-09 | ||
| IN908CH2004 | 2004-09-09 | ||
| PCT/IN2005/000243 WO2006027795A1 (en) | 2004-09-09 | 2005-07-19 | Novel phenylaminopyrimidine derivatives as inhibitors of bcr-abl kinase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2591321A1 CA2591321A1 (en) | 2006-03-16 |
| CA2591321C true CA2591321C (en) | 2013-09-24 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2591321A Expired - Fee Related CA2591321C (en) | 2004-09-09 | 2005-07-19 | Phenylaminopyrimidine derivatives as inhibitors of bcr-abl kinase |
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| Country | Link |
|---|---|
| US (2) | US7910598B2 (https=) |
| EP (2) | EP1786799B1 (https=) |
| JP (1) | JP5184887B2 (https=) |
| KR (1) | KR100948453B1 (https=) |
| CN (1) | CN101068805B (https=) |
| AP (1) | AP2470A (https=) |
| AU (1) | AU2005281299B2 (https=) |
| BR (1) | BRPI0515081B8 (https=) |
| CA (1) | CA2591321C (https=) |
| CY (1) | CY1113617T1 (https=) |
| DK (1) | DK1786799T3 (https=) |
| EA (1) | EA013328B1 (https=) |
| ES (1) | ES2390227T3 (https=) |
| HR (1) | HRP20070146B1 (https=) |
| IL (1) | IL181811A (https=) |
| MA (1) | MA28922B1 (https=) |
| MX (1) | MX2007002819A (https=) |
| NO (1) | NO337598B1 (https=) |
| NZ (1) | NZ554361A (https=) |
| PL (1) | PL1786799T3 (https=) |
| PT (1) | PT1786799E (https=) |
| SI (1) | SI1786799T1 (https=) |
| UA (1) | UA94570C2 (https=) |
| WO (1) | WO2006027795A1 (https=) |
| ZA (2) | ZA200701942B (https=) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US6667300B2 (en) * | 2000-04-25 | 2003-12-23 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
| WO2005113556A1 (en) | 2004-05-13 | 2005-12-01 | Icos Corporation | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
| AP2470A (en) | 2004-09-09 | 2012-09-17 | Natco Pharma Ltd | Novel phenylaminopyrimidine derivatives as inhibitors of BCR-ABL kinase |
| US8735415B2 (en) | 2004-09-09 | 2014-05-27 | Natco Pharma Limited | Acid addition salts of (3,5-Bis trifluoromethyl)-N-[4-methyl-3-(4-pyridin-3yl-pyrimidin-2ylamino)-phenyl]-benzamide |
| US20110190328A1 (en) * | 2004-09-09 | 2011-08-04 | Natco Pharma Limited | Acid addition salts of (3,5-bis trifluoromethyl)-n-[4-methyl-3-(4-pyridin-3yl-pyrimidin-2ylamino)-phenyl]-benzamide |
| US7939541B2 (en) * | 2004-09-09 | 2011-05-10 | Natco Pharma Limited | Intermediates and a process employing the intermediates for the preparation of (3-trifluoromethylsulfonyl)-N-[4-methyl-3-(4-pyridin-3yl-pyrimidin-2ylamino)-phenyl]-benzamide |
| WO2008031534A1 (en) * | 2006-09-11 | 2008-03-20 | Syngenta Participations Ag | Insecticidal compounds |
| BRPI0718677A2 (pt) * | 2006-11-03 | 2013-11-26 | Irm Llc | Compostos e composições como inibidores de quinases proteicas |
| EA200900779A1 (ru) * | 2006-12-14 | 2010-02-26 | Байер Шеринг Фарма Акциенгезельшафт | Производные дигидропиридина, полезные как ингибиторы протеинкиназы |
| EA019524B1 (ru) * | 2007-05-04 | 2014-04-30 | Айрм Ллк | СОЕДИНЕНИЯ И КОМПОЗИЦИИ КАК ИНГИБИТОРЫ КИНАЗЫ с-kit И PDGFR |
| KR101122481B1 (ko) * | 2007-05-04 | 2012-02-29 | 아이알엠 엘엘씨 | Ｃ-ｋｉｔ 및 ｐｄｇｆｒ 키나제 억제제로서의 피리미딘 유도체 및 조성물 |
| US8293757B2 (en) | 2007-08-22 | 2012-10-23 | Irm Llc | 5-(4-(haloalkoxy)phenyl) pyrimidine-2-amine compounds and compositions as kinase inhibitors |
| MX2010002005A (es) | 2007-08-22 | 2010-03-11 | Irm Llc | Derivados de 2-heteroaril-amino-pirimidina como inhibidores de cinasa. |
| AP2651A (en) * | 2008-03-04 | 2013-04-25 | Natco Pharma Ltd | Crystal form of phenylamino pyrimidine derivatives |
| US8067422B2 (en) | 2008-03-04 | 2011-11-29 | Natco Pharma Limited | Crystal form of phenylamino pyrimidine derivatives |
| WO2012004801A1 (en) * | 2010-07-07 | 2012-01-12 | Hetero Research Foundation | Process for imatinib mesylate |
| GB2488788B (en) * | 2011-03-07 | 2013-07-10 | Natco Pharma Ltd | Oral formulation of phenylaminopyrymidine compound with enhanced bioavailability and pharmacological response |
| EP2751104B1 (en) | 2011-09-01 | 2019-09-25 | Novartis AG | Compounds and compositions as c-kit kinase inhibitors |
| US9061028B2 (en) | 2012-02-15 | 2015-06-23 | Natco Pharma Limited | Process for the preparation of Nilotinib |
| CA2876539A1 (en) * | 2012-06-15 | 2013-12-19 | Basf Se | Multicomponent crystals comprising dasatinib and selected co-crystal formers |
| GEAP202014833A (en) | 2015-12-18 | 2020-06-25 | Natco Pharma Ltd | Pharmaceutical compositions comprising phenylaminopyrimidine derivative |
| WO2017156350A1 (en) | 2016-03-09 | 2017-09-14 | K-Gen, Inc. | Methods of cancer treatment |
| WO2022016021A1 (en) | 2020-07-15 | 2022-01-20 | Third Harmonic Bio, Inc. | Crystalline forms of a selective c-kit kinase inhibitor |
| EP4247368A4 (en) | 2020-11-19 | 2024-10-23 | Third Harmonic Bio, Inc. | PHARMACEUTICAL COMPOSITIONS OF A SELECTIVE C-KIT KINASE INHIBITOR AND METHODS FOR THE PREPARATION AND USE THEREOF |
| CN113125689B (zh) * | 2021-03-29 | 2022-02-22 | 创芯国际生物科技(广州)有限公司 | 一种新型mtt细胞活力检测试剂盒及其应用 |
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| TW225528B (https=) | 1992-04-03 | 1994-06-21 | Ciba Geigy Ag | |
| US5516775A (en) | 1992-08-31 | 1996-05-14 | Ciba-Geigy Corporation | Further use of pyrimidine derivatives |
| WO1995009851A1 (en) | 1993-10-01 | 1995-04-13 | Ciba-Geigy Ag | Pharmacologically active pyrimidineamine derivatives and processes for the preparation thereof |
| PT672041E (pt) | 1993-10-01 | 2002-04-29 | Novartis Ag | Derivados da piridina farmacologicamente activos e processos para a sua preparacao |
| WO1995009847A1 (en) | 1993-10-01 | 1995-04-13 | Ciba-Geigy Ag | Pyrimidineamine derivatives and processes for the preparation thereof |
| CO4940418A1 (es) | 1997-07-18 | 2000-07-24 | Novartis Ag | Modificacion de cristal de un derivado de n-fenil-2- pirimidinamina, procesos para su fabricacion y su uso |
| DK1017378T3 (da) * | 1997-09-23 | 2003-03-17 | Astrazeneca Ab | Amidderivater til behandling af sygdomme medieret af cytokiner |
| WO2000007991A1 (en) * | 1998-08-04 | 2000-02-17 | Astrazeneca Ab | Amide derivatives useful as inhibitors of the production of cytokines |
| GB0022438D0 (en) | 2000-09-13 | 2000-11-01 | Novartis Ag | Organic Compounds |
| ES2337995T3 (es) * | 2002-06-28 | 2010-05-03 | Nippon Shinyaku Co., Ltd. | Derivado de amida. |
| GB0222514D0 (en) * | 2002-09-27 | 2002-11-06 | Novartis Ag | Organic compounds |
| AU2003242988A1 (en) * | 2003-06-06 | 2005-01-04 | Adibhatla Kali Sathya Bhujanga Rao | Process for the preparation of the anti-cancer drug imatinib and its analogues |
| ATE454152T1 (de) * | 2003-06-13 | 2010-01-15 | Novartis Pharma Gmbh | 2-aminopyrimidin-derivate als raf-kinase-hemmer |
| AP2470A (en) | 2004-09-09 | 2012-09-17 | Natco Pharma Ltd | Novel phenylaminopyrimidine derivatives as inhibitors of BCR-ABL kinase |
| BRPI0718677A2 (pt) * | 2006-11-03 | 2013-11-26 | Irm Llc | Compostos e composições como inibidores de quinases proteicas |
-
2005
- 2005-07-19 AP AP2007003944A patent/AP2470A/xx active
- 2005-07-19 PL PL05779775T patent/PL1786799T3/pl unknown
- 2005-07-19 AU AU2005281299A patent/AU2005281299B2/en not_active Ceased
- 2005-07-19 CA CA2591321A patent/CA2591321C/en not_active Expired - Fee Related
- 2005-07-19 DK DK05779775.5T patent/DK1786799T3/da active
- 2005-07-19 MX MX2007002819A patent/MX2007002819A/es active IP Right Grant
- 2005-07-19 PT PT05779775T patent/PT1786799E/pt unknown
- 2005-07-19 JP JP2007530854A patent/JP5184887B2/ja not_active Expired - Fee Related
- 2005-07-19 BR BRPI0515081A patent/BRPI0515081B8/pt not_active IP Right Cessation
- 2005-07-19 UA UAA200703971A patent/UA94570C2/ru unknown
- 2005-07-19 EA EA200700601A patent/EA013328B1/ru unknown
- 2005-07-19 CN CN2005800300912A patent/CN101068805B/zh not_active Expired - Fee Related
- 2005-07-19 WO PCT/IN2005/000243 patent/WO2006027795A1/en not_active Ceased
- 2005-07-19 NZ NZ554361A patent/NZ554361A/en not_active IP Right Cessation
- 2005-07-19 KR KR1020077008040A patent/KR100948453B1/ko not_active Expired - Fee Related
- 2005-07-19 ES ES05779775T patent/ES2390227T3/es not_active Expired - Lifetime
- 2005-07-19 SI SI200531589T patent/SI1786799T1/sl unknown
- 2005-07-19 EP EP05779775A patent/EP1786799B1/en not_active Expired - Lifetime
- 2005-07-19 EP EP10184904.0A patent/EP2295424B1/en not_active Expired - Lifetime
- 2005-07-19 HR HRP20070146AA patent/HRP20070146B1/hr not_active IP Right Cessation
-
2007
- 2007-03-05 US US11/714,565 patent/US7910598B2/en not_active Expired - Fee Related
- 2007-03-06 ZA ZA200701942A patent/ZA200701942B/xx unknown
- 2007-03-08 IL IL181811A patent/IL181811A/en active IP Right Grant
- 2007-03-22 NO NO20071521A patent/NO337598B1/no not_active IP Right Cessation
- 2007-04-06 MA MA29808A patent/MA28922B1/fr unknown
- 2007-04-12 ZA ZA200703123A patent/ZA200703123B/en unknown
-
2008
- 2008-03-04 US US12/042,235 patent/US8183253B2/en not_active Expired - Fee Related
-
2012
- 2012-09-28 CY CY20121100895T patent/CY1113617T1/el unknown
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