WO2004074502A2 - A process of preparing imatinib - Google Patents
A process of preparing imatinib Download PDFInfo
- Publication number
- WO2004074502A2 WO2004074502A2 PCT/GB2004/000018 GB2004000018W WO2004074502A2 WO 2004074502 A2 WO2004074502 A2 WO 2004074502A2 GB 2004000018 W GB2004000018 W GB 2004000018W WO 2004074502 A2 WO2004074502 A2 WO 2004074502A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- imatinib
- formula
- methyl
- salt
- process according
- Prior art date
Links
- KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 title claims abstract description 159
- 239000005517 L01XE01 - Imatinib Substances 0.000 title claims abstract description 129
- 229960002411 imatinib Drugs 0.000 title claims abstract description 129
- 238000000034 method Methods 0.000 title claims abstract description 94
- 150000003839 salts Chemical class 0.000 claims abstract description 82
- 239000002253 acid Substances 0.000 claims abstract description 43
- 239000003960 organic solvent Substances 0.000 claims abstract description 24
- 239000012458 free base Substances 0.000 claims abstract description 22
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 18
- -1 4-(4-methyl-piperazino methyl)benzoyl halide Chemical class 0.000 claims abstract description 11
- 125000002346 iodo group Chemical group I* 0.000 claims abstract description 11
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- JKXCZYCVHPKTPK-UHFFFAOYSA-N hydrate;trihydrochloride Chemical compound O.Cl.Cl.Cl JKXCZYCVHPKTPK-UHFFFAOYSA-N 0.000 claims description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 11
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 11
- 229960003685 imatinib mesylate Drugs 0.000 claims description 11
- YLMAHDNUQAMNNX-UHFFFAOYSA-N imatinib methanesulfonate Chemical compound CS(O)(=O)=O.C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 YLMAHDNUQAMNNX-UHFFFAOYSA-N 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 239000003638 chemical reducing agent Substances 0.000 claims description 9
- KNBRFZWWCBSGDU-UHFFFAOYSA-N 4-[(4-methylpiperazin-1-yl)methyl]benzoyl chloride Chemical compound C1CN(C)CCN1CC1=CC=C(C(Cl)=O)C=C1 KNBRFZWWCBSGDU-UHFFFAOYSA-N 0.000 claims description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 230000000118 anti-neoplastic effect Effects 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 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 5
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 5
- 230000000259 anti-tumor effect Effects 0.000 claims description 5
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000001119 stannous chloride Substances 0.000 claims description 5
- 235000011150 stannous chloride Nutrition 0.000 claims description 5
- 230000001668 ameliorated effect Effects 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- VQVSJNHSDJDRMF-UHFFFAOYSA-N 5-(5-amino-2-methylphenyl)-4-pyridin-3-ylpyrimidin-2-amine Chemical compound CC1=CC=C(N)C=C1C1=CN=C(N)N=C1C1=CC=CN=C1 VQVSJNHSDJDRMF-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 2
- 229940113088 dimethylacetamide Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000009435 amidation Effects 0.000 description 3
- 238000007112 amidation reaction Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- LOYDNMMRPAMIPU-UHFFFAOYSA-N CC1C(NC(c2ccc(CN3CCN(C)CC3)cc2)=O)=CC(NC2=NC=CC(c3cccnc3)N2)=C(C)C1 Chemical compound CC1C(NC(c2ccc(CN3CCN(C)CC3)cc2)=O)=CC(NC2=NC=CC(c3cccnc3)N2)=C(C)C1 LOYDNMMRPAMIPU-UHFFFAOYSA-N 0.000 description 1
- MHFRXTADMITGMB-UHFFFAOYSA-N Cc(ccc(NC(c1ccc(CN2CCN(C)CC2)cc1)=O)c1)c1NC1=NC=CC(c2cccnc2)N1 Chemical compound Cc(ccc(NC(c1ccc(CN2CCN(C)CC2)cc1)=O)c1)c1NC1=NC=CC(c2cccnc2)N1 MHFRXTADMITGMB-UHFFFAOYSA-N 0.000 description 1
- 206010018338 Glioma Diseases 0.000 description 1
- 150000004926 Imatinib derivatives Chemical class 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- QHYIGPGWXQQZSA-UHFFFAOYSA-N azane;methanesulfonic acid Chemical compound [NH4+].CS([O-])(=O)=O QHYIGPGWXQQZSA-UHFFFAOYSA-N 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002050 international nonproprietary name Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 208000037841 lung tumor Diseases 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000036457 multidrug resistance Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
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
- C07D401/14—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
-
- 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
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BRPI0407672-9A BRPI0407672A (en) | 2003-02-18 | 2004-01-08 | processes for preparing imatinib and an acid addition salt thereof, imatinib acid addition salts, pharmaceutically acceptable composition thereof, imatinib and use thereof |
US10/546,193 US7638627B2 (en) | 2003-02-18 | 2004-01-08 | Process of preparing imatinib and imatinib prepared thereby |
EP04700728A EP1599462B1 (en) | 2003-02-18 | 2004-01-08 | Process of preparing imatinib |
KR1020057015166A KR101086845B1 (en) | 2003-02-18 | 2004-01-08 | A process of preparing imatinib |
JP2006502181A JP5064024B2 (en) | 2003-02-18 | 2004-01-08 | Method for producing imatinib and imatinib produced by the method |
NZ542040A NZ542040A (en) | 2003-02-18 | 2004-01-08 | A process of preparing imatinib |
AU2004213616A AU2004213616B2 (en) | 2003-02-18 | 2004-01-08 | A process of preparing imatinib |
CA2516370A CA2516370C (en) | 2003-02-18 | 2004-01-08 | A process of preparing imatinib and imatinib prepared thereby |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0303730.6 | 2003-02-18 | ||
GB0303730A GB2398565A (en) | 2003-02-18 | 2003-02-18 | Imatinib preparation and salts |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2004074502A2 true WO2004074502A2 (en) | 2004-09-02 |
WO2004074502A3 WO2004074502A3 (en) | 2004-10-28 |
Family
ID=9953245
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB2004/000018 WO2004074502A2 (en) | 2003-02-18 | 2004-01-08 | A process of preparing imatinib |
Country Status (12)
Country | Link |
---|---|
US (1) | US7638627B2 (en) |
EP (1) | EP1599462B1 (en) |
JP (1) | JP5064024B2 (en) |
KR (1) | KR101086845B1 (en) |
AU (1) | AU2004213616B2 (en) |
BR (1) | BRPI0407672A (en) |
CA (1) | CA2516370C (en) |
GB (1) | GB2398565A (en) |
NZ (1) | NZ542040A (en) |
PL (1) | PL378128A1 (en) |
RU (1) | RU2415849C2 (en) |
WO (1) | WO2004074502A2 (en) |
Cited By (26)
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---|---|---|---|---|
WO2005075454A2 (en) | 2004-02-04 | 2005-08-18 | Novartis Ag | SALT FORMS OF 4-(4-METHYLPIPERAZIN-1-YLMETHYL)-n-[4-METHYL-3-(4-PYRIDIN-3-YL)PYRIMIDIN-2-YLAMINO)PHENYL]-BENZAMIDE |
WO2006054314A1 (en) * | 2004-11-17 | 2006-05-26 | Natco Pharma Limited | Polymorphic forms of imatinib mesylate |
JP2006527230A (en) * | 2003-06-13 | 2006-11-30 | ノバルティス アクチエンゲゼルシャフト | 2-Aminopyrimidine derivatives as RAF kinase inhibitors |
JP2007302658A (en) * | 2006-04-27 | 2007-11-22 | Ivax Pharmaceuticals Spolecnost Sro | POLYMORPHIC FORM AND NEW CRYSTAL FORM AND AMORPHOUS FORM OF IMATINIB MESYLATE, AND METHOD FOR PREPARING FORMalpha |
WO2008051597A1 (en) * | 2006-10-26 | 2008-05-02 | Sicor Inc. | Process for the preparation of imatinib |
EP1988089A1 (en) | 2006-10-26 | 2008-11-05 | Sicor, Inc. | Imatinib base, and imatinib mesylate and processes for preparation thereof |
WO2008135980A1 (en) * | 2007-05-02 | 2008-11-13 | Chemagis Ltd. | Imatinib production process |
US7507821B2 (en) | 2004-12-30 | 2009-03-24 | Chemagis Ltd. | Process for preparing Imatinib |
EP2062885A1 (en) * | 2007-11-21 | 2009-05-27 | Eczacibasi-Zentiva Kimyasal Ürünler Sanayi ve Ticaret A.S. | Acid addition salts of imatinib and formulations comprising the same |
WO2009080366A1 (en) * | 2007-12-22 | 2009-07-02 | Synthon B.V. | A process of making imatinib |
WO2010133976A2 (en) | 2009-05-22 | 2010-11-25 | Actavis Group Ptc Ehf | Substantially pure imatinib or a pharmaceutically acceptable salt thereof |
WO2011070588A1 (en) | 2009-12-10 | 2011-06-16 | Arch Pharmalabs Limited | Process for the preparation of imatinib and salts thereof |
US7977348B2 (en) | 2006-04-27 | 2011-07-12 | Sicor Inc. | Polymorphic forms of imatinib mesylate and processes for preparation of novel crystalline forms as well as amorphous and form α |
WO2011095835A1 (en) | 2010-02-02 | 2011-08-11 | Actavis Group Ptc Ehf | Highly pure imatinib or a pharmaceutically acceptable salt thereof |
US8048883B2 (en) | 2004-02-11 | 2011-11-01 | Natco Pharma Limited | Polymorphic form of imatinib mesylate and a process for its preparation |
US8067421B2 (en) | 2006-04-27 | 2011-11-29 | Sicor Inc. | Polymorphic forms of imatinib mesylate and processes for preparation of novel crystalline forms as well as amorphous and form α |
WO2011157450A1 (en) | 2010-06-18 | 2011-12-22 | Krka, D. D., Novo Mesto | New polymorphic form of imatinib base and preparation of salts thereof |
WO2012026897A1 (en) * | 2010-08-23 | 2012-03-01 | MUSTAFA NEVZAT iLAÇ SANAYU A.Ş. | A process for the preparation of imatinib base |
CN102382100A (en) * | 2011-03-09 | 2012-03-21 | 上海昕盛医药科技有限公司 | Preparation method of imatinib |
WO2012087255A2 (en) | 2010-12-20 | 2012-06-28 | Mahmut Bilgic | Pharmaceutical formulations |
WO2012131711A1 (en) * | 2011-03-31 | 2012-10-04 | Ind-Swift Laboratories Limited | Improved process for preparation of imatinib and its mesylate salt |
WO2013035102A1 (en) | 2011-09-05 | 2013-03-14 | Natco Pharma Limited | Processes for the preparation of imatinib base and intermediates thereof |
US8414918B2 (en) | 2007-09-25 | 2013-04-09 | Teva Pharmaceutical Industries Ltd. | Stable imatinib compositions |
RU2483065C2 (en) * | 2005-07-20 | 2013-05-27 | Новартис Аг | 4-methyl-n-[3-(4-methylimidazol-1-yl)-5-trifluoromethylphenyl]-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)benzamide salts |
CN103910711A (en) * | 2014-03-24 | 2014-07-09 | 福建天泉药业股份有限公司 | Imatinib free alkali crystal form and preparation method thereof |
WO2017129624A1 (en) | 2016-01-25 | 2017-08-03 | Krka, D.D., Novo Mesto | Fast dispersible pharmaceutical composition comprising tyrosine-kinase inhibitor |
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GB0202873D0 (en) * | 2002-02-07 | 2002-03-27 | Novartis Ag | Organic compounds |
WO2006024863A1 (en) * | 2004-09-02 | 2006-03-09 | Cipla Limited | Stable crystal form of imatinib mesylate and process for the preparation thereof |
AU2005288736B2 (en) * | 2004-09-27 | 2008-08-14 | Astrazeneca Ab | Cancer combination therapy comprising AZD2171 and imatinib |
US7439358B2 (en) * | 2006-02-08 | 2008-10-21 | Boehringer Ingelheim International Gmbh | Specific salt, anhydrous and crystalline form of a dihydropteridione derivative |
EP2314297A1 (en) * | 2006-04-05 | 2011-04-27 | Novartis AG | Combinations comprising bcr-abl/c-kit/pdgf-r tk inhibitors for treating cancer |
US20060223816A1 (en) * | 2006-05-08 | 2006-10-05 | Chemagis Ltd. | Imatinib mesylate alpha form and production process therefor |
WO2008024826A2 (en) * | 2006-08-23 | 2008-02-28 | Board Of Regents, The University Of Texas System | Radiohalothymidines and methods of their synthesis and use in pet imaging of cancers |
MX2009002336A (en) * | 2006-09-01 | 2009-03-20 | Teva Pharma | Imatinib compositions. |
RU2329260C1 (en) * | 2007-02-20 | 2008-07-20 | Юрий Иосифович Копырин | Method of obtaining 2-anilinopyrimidines or their salts (options) |
PT2305263E (en) * | 2007-06-07 | 2012-10-22 | Novartis Ag | Stabilized amorphous forms of imatinib mesylate |
WO2009060463A1 (en) * | 2007-11-05 | 2009-05-14 | Natco Pharma Limited | An environmentally friendly process for the preparation of imatinib base |
WO2010009402A2 (en) * | 2008-07-17 | 2010-01-21 | Teva Pharmaceutical Industries Ltd. | Nilotinib intermediates and preparation thereof |
WO2011114337A1 (en) * | 2010-03-15 | 2011-09-22 | Natco Pharma Limited | Process for the preparation of highly pure crystalline imatinib base |
US8609842B2 (en) | 2010-04-23 | 2013-12-17 | Fujian South Pharmaceutical Co., Ltd. | Method for synthesizing Imatinib |
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Also Published As
Publication number | Publication date |
---|---|
WO2004074502A3 (en) | 2004-10-28 |
US20060173182A1 (en) | 2006-08-03 |
EP1599462B1 (en) | 2013-03-27 |
AU2004213616A1 (en) | 2004-09-02 |
AU2004213616A2 (en) | 2004-09-02 |
KR101086845B1 (en) | 2011-11-24 |
GB2398565A (en) | 2004-08-25 |
CA2516370C (en) | 2012-08-21 |
CA2516370A1 (en) | 2004-09-02 |
RU2005129100A (en) | 2006-06-10 |
JP5064024B2 (en) | 2012-10-31 |
US7638627B2 (en) | 2009-12-29 |
KR20050108358A (en) | 2005-11-16 |
AU2004213616B2 (en) | 2011-05-26 |
EP1599462A2 (en) | 2005-11-30 |
JP2006518360A (en) | 2006-08-10 |
BRPI0407672A (en) | 2006-03-01 |
GB0303730D0 (en) | 2003-03-26 |
NZ542040A (en) | 2009-02-28 |
PL378128A1 (en) | 2006-03-06 |
RU2415849C2 (en) | 2011-04-10 |
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