HRP20110709T1 - Postupak sinteze spojeva 2-aminotioazola kao inhibitora kinaza - Google Patents
Postupak sinteze spojeva 2-aminotioazola kao inhibitora kinaza Download PDFInfo
- Publication number
- HRP20110709T1 HRP20110709T1 HR20110709T HRP20110709T HRP20110709T1 HR P20110709 T1 HRP20110709 T1 HR P20110709T1 HR 20110709 T HR20110709 T HR 20110709T HR P20110709 T HRP20110709 T HR P20110709T HR P20110709 T1 HRP20110709 T1 HR P20110709T1
- Authority
- HR
- Croatia
- Prior art keywords
- group
- formula
- compound
- alkyl
- halogen
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract 29
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- 229940043355 kinase inhibitor Drugs 0.000 title 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract 12
- 150000002367 halogens Chemical class 0.000 claims abstract 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 8
- -1 cyan Chemical group 0.000 claims abstract 8
- 125000001424 substituent group Chemical group 0.000 claims abstract 8
- 102100039131 Integrator complex subunit 5 Human genes 0.000 claims abstract 7
- 101710092888 Integrator complex subunit 5 Proteins 0.000 claims abstract 7
- 150000001412 amines Chemical class 0.000 claims abstract 7
- 125000005265 dialkylamine group Chemical group 0.000 claims abstract 7
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 5
- 102100039134 Integrator complex subunit 4 Human genes 0.000 claims abstract 4
- 101710092887 Integrator complex subunit 4 Proteins 0.000 claims abstract 4
- 125000003118 aryl group Chemical group 0.000 claims abstract 4
- 150000003839 salts Chemical class 0.000 claims abstract 4
- 150000003973 alkyl amines Chemical class 0.000 claims abstract 3
- 239000000010 aprotic solvent Substances 0.000 claims abstract 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 3
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 3
- 239000001257 hydrogen Substances 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims abstract 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims abstract 2
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims abstract 2
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910019142 PO4 Inorganic materials 0.000 claims abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 2
- 230000008878 coupling Effects 0.000 claims abstract 2
- 238000010168 coupling process Methods 0.000 claims abstract 2
- 238000005859 coupling reaction Methods 0.000 claims abstract 2
- MAEBCGDGGATMSC-OSHGGGOQSA-N cyclamine Chemical group O([C@H]1CO[C@H]([C@@H]([C@H]1O[C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O[C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@H]1CC[C@]2(C)[C@H]3CCC45OCC6([C@@H](C[C@@]4(C)[C@]3(C)CCC2C1(C)C)O)CC[C@@](C[C@@H]65)(C)C=O)[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O MAEBCGDGGATMSC-OSHGGGOQSA-N 0.000 claims abstract 2
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 125000005842 heteroatom Chemical group 0.000 claims abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract 2
- 239000010452 phosphate Substances 0.000 claims abstract 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims abstract 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract 2
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 238000001914 filtration Methods 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 239000002244 precipitate Substances 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 102100024061 Integrator complex subunit 1 Human genes 0.000 claims 2
- 101710092857 Integrator complex subunit 1 Proteins 0.000 claims 2
- 102100033265 Integrator complex subunit 2 Human genes 0.000 claims 2
- 108050002021 Integrator complex subunit 2 Proteins 0.000 claims 2
- 239000002841 Lewis acid Substances 0.000 claims 2
- 239000012190 activator Substances 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 2
- 150000007517 lewis acids Chemical class 0.000 claims 2
- 125000003367 polycyclic group Chemical group 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 239000003586 protic polar solvent Substances 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- ABFPKTQEQNICFT-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1Cl ABFPKTQEQNICFT-UHFFFAOYSA-M 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 102100033263 Integrator complex subunit 3 Human genes 0.000 claims 1
- 101710092886 Integrator complex subunit 3 Proteins 0.000 claims 1
- 239000007868 Raney catalyst Substances 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical group [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- 229910000564 Raney nickel Inorganic materials 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- WJEOLQLKVOPQFV-UHFFFAOYSA-N masitinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3SC=C(N=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 WJEOLQLKVOPQFV-UHFFFAOYSA-N 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 239000002904 solvent Chemical group 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 125000000565 sulfonamide group Chemical group 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 1
- 150000003568 thioethers Chemical class 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Obesity (AREA)
- Pulmonology (AREA)
- Neurosurgery (AREA)
- Emergency Medicine (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Communicable Diseases (AREA)
- Endocrinology (AREA)
- Transplantation (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88958707P | 2007-02-13 | 2007-02-13 | |
| PCT/EP2008/051704 WO2008098949A2 (en) | 2007-02-13 | 2008-02-13 | Process for the synthesis of 2-aminothiazole compounds as kinase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110709T1 true HRP20110709T1 (hr) | 2011-11-30 |
Family
ID=39332208
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110709T HRP20110709T1 (hr) | 2007-02-13 | 2011-10-05 | Postupak sinteze spojeva 2-aminotioazola kao inhibitora kinaza |
| HRP20140986AT HRP20140986T1 (hr) | 2007-02-13 | 2014-10-15 | Polimorfni oblik derivata 2-amino(nitroaril)tiazola |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20140986AT HRP20140986T1 (hr) | 2007-02-13 | 2014-10-15 | Polimorfni oblik derivata 2-amino(nitroaril)tiazola |
Country Status (23)
| Country | Link |
|---|---|
| US (3) | US8153792B2 (ja) |
| EP (2) | EP2366703B1 (ja) |
| JP (2) | JP5568312B2 (ja) |
| KR (1) | KR20090110851A (ja) |
| CN (2) | CN101657446B (ja) |
| AR (1) | AR065337A1 (ja) |
| AT (1) | ATE515506T1 (ja) |
| AU (1) | AU2008214679A1 (ja) |
| BR (1) | BRPI0807626B1 (ja) |
| CA (2) | CA2970628C (ja) |
| ES (2) | ES2522169T3 (ja) |
| HR (2) | HRP20110709T1 (ja) |
| IL (1) | IL200320A0 (ja) |
| MA (1) | MA31180B1 (ja) |
| MX (1) | MX2009008665A (ja) |
| NZ (1) | NZ578944A (ja) |
| PL (2) | PL2366703T3 (ja) |
| RU (2) | RU2456285C2 (ja) |
| SI (2) | SI2118099T1 (ja) |
| TN (1) | TN2009000342A1 (ja) |
| TW (1) | TWI406862B (ja) |
| WO (1) | WO2008098949A2 (ja) |
| ZA (1) | ZA200905981B (ja) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050239852A1 (en) | 2002-08-02 | 2005-10-27 | Ab Science | 2-(3-aminoaryl)amino-4-aryl-thiazoles and their use as c-kit inhibitors |
| US8450302B2 (en) | 2002-08-02 | 2013-05-28 | Ab Science | 2-(3-aminoaryl) amino-4-aryl-thiazoles and their use as c-kit inhibitors |
| WO2011092273A1 (en) | 2010-01-28 | 2011-08-04 | Ab Science | Treatment of gist with masitinib |
| WO2011092338A1 (en) | 2010-02-01 | 2011-08-04 | Ab Science | Combined treatment of pancreatic cancer with gemcitabine and masitinib |
| AR080380A1 (es) | 2010-03-09 | 2012-04-04 | Ab Science | Tratamiento de la demencia tipo alzheimer con masitinib |
| TW201204360A (en) | 2010-04-20 | 2012-02-01 | Ab Science | Treatment of multiple sclerosis with MASITINIB |
| TW201204719A (en) | 2010-06-02 | 2012-02-01 | Ab Science | Treatment of rheumatoid arthritis with masitinib |
| WO2012059526A1 (en) | 2010-11-05 | 2012-05-10 | Ab Science | Treatment of mastocytosis with masitinib |
| US10045978B2 (en) | 2010-11-05 | 2018-08-14 | Ab Science | Treatment of mastocytosis with masitinib |
| US9078894B2 (en) | 2011-02-04 | 2015-07-14 | Ab Science | Treatment of severe persistant asthma with masitinib |
| AR085934A1 (es) | 2011-04-08 | 2013-11-06 | Ab Science | Tratamiento de mieloma multiple con masitinib |
| JP6234466B2 (ja) | 2012-10-04 | 2017-11-22 | エービー サイエンス | 予測因子を用いて同定された患者サブ集団における癌の処置のためのマシチニブの使用 |
| TW201605449A (zh) | 2013-12-02 | 2016-02-16 | Ａｂ化學公司 | 馬賽替尼治療結腸直腸癌的用途 |
| EP2886543A1 (en) | 2013-12-18 | 2015-06-24 | Sandoz Ag | Crystalline form of mastinib mesylate |
| US20170196853A1 (en) | 2014-06-02 | 2017-07-13 | Ab Science | Use of an inhibitor of kinase activity, particularly masitinib, for treatment of prostate cancer |
| CN105585556A (zh) * | 2014-11-13 | 2016-05-18 | 连云港杰瑞药业有限公司 | 一种伊马替尼的合成方法 |
| CN106794179A (zh) * | 2015-07-29 | 2017-05-31 | 苏州晶云药物科技有限公司 | 马赛替尼甲磺酸盐的新晶型及其制备方法 |
| WO2017060308A1 (en) | 2015-10-05 | 2017-04-13 | Ab Science | Treatment of severe systemic mastocytosis with masitinib |
| CA3018635C (en) | 2016-03-25 | 2023-09-26 | Ab Science | Use of masitinib for treatment of an amyotrophic lateral sclerosis patient subpopulation |
| WO2018177854A1 (en) | 2017-03-31 | 2018-10-04 | Sandoz Ag | Crystalline form of masitinib |
| US10696638B2 (en) | 2017-12-26 | 2020-06-30 | Industrial Technology Research Institute | Compounds for inhibiting AGC kinase and pharmaceutical compositions comprising the same |
| US20230000838A1 (en) | 2019-11-22 | 2023-01-05 | Ab Science | Masitinib for the treatment of sickle cell disease |
| EP3831384A1 (en) | 2019-12-02 | 2021-06-09 | AB Science | Use of masitinib for the treatment of eosinophilic asthma |
| CN115515590A (zh) | 2020-02-20 | 2022-12-23 | Ab科学有限公司 | 马赛替尼用于治疗多发性硬化患者亚群 |
| KR20230014681A (ko) | 2020-04-10 | 2023-01-30 | 에이비 사이언스 | 코로나바이러스 질환 2019(covid-19)의 치료를 위한 마시티닙의 용도 |
| CA3201259A1 (en) | 2020-12-16 | 2022-06-23 | Alain Moussy | Masitinib for the treatment of alzheimer's disease |
| US20230321081A1 (en) | 2021-05-17 | 2023-10-12 | Ab Science | Masitinib for the treatment of castrate-resistant prostate cancer |
| CN115850258B (zh) * | 2022-12-27 | 2024-09-24 | 东北林业大学 | 一种马赛替尼的合成方法 |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3299087A (en) * | 1961-04-24 | 1967-01-17 | Geigy Chem Corp | Nu, nu'-bis-(thiazolyl)-phenylenediamines |
| EP0983260A2 (en) * | 1997-05-22 | 2000-03-08 | G.D. Searle & Co. | 3(5)-HETEROARYL SUBSTITUTED PYRAZOLES AS p38 KINASE INHIBITORS |
| 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 |
| GB9718913D0 (en) * | 1997-09-05 | 1997-11-12 | Glaxo Group Ltd | Substituted oxindole derivatives |
| CN1158269C (zh) * | 1997-10-27 | 2004-07-21 | 阿古龙制药公司 | 作为cdk抑制剂的取代的4-氨基-噻唑-2-基化合物 |
| US6114365A (en) * | 1999-08-12 | 2000-09-05 | Pharmacia & Upjohn S.P.A. | Arylmethyl-carbonylamino-thiazole derivatives, process for their preparation, and their use as antitumor agents |
| WO2001017995A1 (en) * | 1999-09-10 | 2001-03-15 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| US20050176687A1 (en) | 2001-06-29 | 2005-08-11 | Alain Moussy | Use of tyrosine kinase inhibitors for treating autoimmune diseases |
| US7727731B2 (en) | 2001-06-29 | 2010-06-01 | Ab Science | Potent, selective and non toxic c-kit inhibitors |
| DK1401415T3 (da) | 2001-06-29 | 2006-10-16 | Ab Science | Anvendelse af N-phenyl-2-pyrimidinamin-derivater til behandling af inflammatoriske sygdomme |
| CA2452371A1 (en) | 2001-06-29 | 2003-01-09 | Ab Science | Use of tyrosine kinase inhibitors for treating allergic diseases |
| WO2003002107A2 (en) | 2001-06-29 | 2003-01-09 | Ab Science | Use of tyrosine kinase inhibitors for treating multiple sclerosis (ms) |
| CA2452171A1 (en) | 2001-06-29 | 2003-01-09 | Ab Science | Use of potent, selective and non toxic c-kit inhibitors for treating mastocytosis |
| JP2004537542A (ja) | 2001-06-29 | 2004-12-16 | アブ サイエンス | 炎症性腸疾患（ｉｂｄ）を治療するための、チロシンキナーゼ阻害剤の使用 |
| CA2452366A1 (en) | 2001-06-29 | 2003-01-16 | Ab Science | Use of potent, selective and non toxic c-kit inhibitors for treating tumor angiogenesis |
| US20030091974A1 (en) | 2001-06-29 | 2003-05-15 | Alain Moussy | Method for screening compounds capable of depleting mast cells |
| WO2003002105A2 (en) | 2001-06-29 | 2003-01-09 | Ab Science | Use of tyrosine kinase inhibitors for treating bone loss |
| JP2005507916A (ja) | 2001-09-20 | 2005-03-24 | アブ サイエンス | 細菌感染症を治療するための、強力で選択的かつ非毒性のｃ−ｋｉｔ阻害剤の使用方法 |
| EP1461032B1 (en) | 2001-09-20 | 2008-07-16 | AB Science | Use of c-kit inhibitors for promoting hair growth |
| JP2005511596A (ja) | 2001-09-20 | 2005-04-28 | アブ サイエンス | ヒトの皮膚を白くし、且つメラノサイト機能不全関連疾病を治療するためのチロシンキナーゼ阻害剤の使用方法 |
| JP2005526048A (ja) | 2002-02-27 | 2005-09-02 | アブ サイエンス | Ｃｎｓ疾患を治療するためのチロシンキナーゼ阻害剤の使用方法 |
| DE60323613D1 (de) | 2002-02-27 | 2008-10-30 | Ab Science | Verwendung von tyrosinkinase-hemmern zur behandlung von erkrankungen im zusammenhang mit substanzgebrauch |
| MXPA04011579A (es) * | 2002-05-29 | 2005-03-07 | Amgen Inc | Derivados de 2-oxo-2,3,4-trihidroquinazolinilo para el tratamiento de trastornos relacionados con la proliferacion celular. |
| US20050239852A1 (en) | 2002-08-02 | 2005-10-27 | Ab Science | 2-(3-aminoaryl)amino-4-aryl-thiazoles and their use as c-kit inhibitors |
| SE0202462D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | Novel use |
| MXPA05008309A (es) * | 2003-02-10 | 2005-09-20 | Amgen Inc | Ligandos de receptor vaniloide y su uso en tratamientos. |
| DE602004013283D1 (de) | 2003-02-27 | 2008-06-05 | Ab Science | Diagnostisches verfahren der mastozytose |
| FR2854158B1 (fr) * | 2003-04-25 | 2006-11-17 | Sanofi Synthelabo | Derives de 2-acylamino-4-phenylethiazole, leur preparation et leur application en therapeutique |
| JP2007500725A (ja) * | 2003-07-29 | 2007-01-18 | アイアールエム・リミテッド・ライアビリティ・カンパニー | プロテインキナーゼ阻害剤としての化合物および組成物 |
| CA2535242A1 (en) | 2003-08-15 | 2005-02-24 | Ab Science | Use of c-kit inhibitors for treating type ii diabetes |
| US7363881B2 (en) | 2003-11-06 | 2008-04-29 | Nova-Tech Engineering, Inc. | Beak treatment with tongue protection |
| PT1702917T (pt) | 2003-12-25 | 2017-11-14 | Nippon Shinyaku Co Ltd | Derivado de amida e medicamento |
| US7650848B2 (en) * | 2004-02-17 | 2010-01-26 | University Of Florida Research Foundation, Inc. | Surface topographies for non-toxic bioadhesion control |
| WO2005115385A1 (en) * | 2004-05-24 | 2005-12-08 | Ab Science | Use of c-kit inhibitors for treating acne |
| TW200702876A (en) * | 2005-07-04 | 2007-01-16 | Avermedia Tech Inc | Projector device capable of sychronously encoding audio and video to become AV sychronous paly file |
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