NO322626B1 - Hydroklorid-etanol-solvatform av (-)-cis-2-(2-klorfenyl)-5,7-dihydroksy-8[4R-(3S-hydroksy-1-metyl)piperidinyl]-4H-1-benzopyran-4-on, fremgangsmate for fremstilling derav og anvendelse derav ved behandling av cancer. - Google Patents
Hydroklorid-etanol-solvatform av (-)-cis-2-(2-klorfenyl)-5,7-dihydroksy-8[4R-(3S-hydroksy-1-metyl)piperidinyl]-4H-1-benzopyran-4-on, fremgangsmate for fremstilling derav og anvendelse derav ved behandling av cancer. Download PDFInfo
- Publication number
- NO322626B1 NO322626B1 NO20023385A NO20023385A NO322626B1 NO 322626 B1 NO322626 B1 NO 322626B1 NO 20023385 A NO20023385 A NO 20023385A NO 20023385 A NO20023385 A NO 20023385A NO 322626 B1 NO322626 B1 NO 322626B1
- Authority
- NO
- Norway
- Prior art keywords
- cis
- benzopyran
- chlorophenyl
- dihydroxy
- methyl
- Prior art date
Links
- 125000003386 piperidinyl group Chemical group 0.000 title claims description 23
- 239000012453 solvate Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 9
- 206010028980 Neoplasm Diseases 0.000 title claims description 8
- 201000011510 cancer Diseases 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 title claims 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 23
- 239000013078 crystal Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 239000003039 volatile agent Substances 0.000 claims description 2
- FQUXBVQTVWLTDK-UHFFFAOYSA-N chromen-4-one;hydrochloride Chemical compound Cl.C1=CC=C2C(=O)C=COC2=C1 FQUXBVQTVWLTDK-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- BIIVYFLTOXDAOV-YVEFUNNKSA-N alvocidib Chemical compound O[C@@H]1CN(C)CC[C@@H]1C1=C(O)C=C(O)C2=C1OC(C=1C(=CC=CC=1)Cl)=CC2=O BIIVYFLTOXDAOV-YVEFUNNKSA-N 0.000 description 6
- 229950010817 alvocidib Drugs 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 102000003903 Cyclin-dependent kinases Human genes 0.000 description 3
- 108090000266 Cyclin-dependent kinases Proteins 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- 108091007914 CDKs Proteins 0.000 description 2
- 108091000080 Phosphotransferase Proteins 0.000 description 2
- 102000001253 Protein Kinase Human genes 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 101150073031 cdk2 gene Proteins 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 102000020233 phosphotransferase Human genes 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 108060006633 protein kinase Proteins 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- IKCLCGXPQILATA-UHFFFAOYSA-M 2-chlorobenzoate Chemical compound [O-]C(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-M 0.000 description 1
- 229940126074 CDK kinase inhibitor Drugs 0.000 description 1
- 101150012716 CDK1 gene Proteins 0.000 description 1
- 101100005789 Caenorhabditis elegans cdk-4 gene Proteins 0.000 description 1
- 102000002554 Cyclin A Human genes 0.000 description 1
- 108010068192 Cyclin A Proteins 0.000 description 1
- 102000002427 Cyclin B Human genes 0.000 description 1
- 108010068150 Cyclin B Proteins 0.000 description 1
- 102000003909 Cyclin E Human genes 0.000 description 1
- 108090000257 Cyclin E Proteins 0.000 description 1
- 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 description 1
- 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 description 1
- 108010025468 Cyclin-Dependent Kinase 6 Proteins 0.000 description 1
- 102100032857 Cyclin-dependent kinase 1 Human genes 0.000 description 1
- 101710106279 Cyclin-dependent kinase 1 Proteins 0.000 description 1
- 102100036239 Cyclin-dependent kinase 2 Human genes 0.000 description 1
- 102100036252 Cyclin-dependent kinase 4 Human genes 0.000 description 1
- 102100026804 Cyclin-dependent kinase 6 Human genes 0.000 description 1
- 102100026810 Cyclin-dependent kinase 7 Human genes 0.000 description 1
- 102100034770 Cyclin-dependent kinase inhibitor 3 Human genes 0.000 description 1
- 102000001301 EGF receptor Human genes 0.000 description 1
- 108060006698 EGF receptor Proteins 0.000 description 1
- 101100059559 Emericella nidulans (strain FGSC A4 / ATCC 38163 / CBS 112.46 / NRRL 194 / M139) nimX gene Proteins 0.000 description 1
- 241000400611 Eucalyptus deanei Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 102000009465 Growth Factor Receptors Human genes 0.000 description 1
- 108010009202 Growth Factor Receptors Proteins 0.000 description 1
- 101000911952 Homo sapiens Cyclin-dependent kinase 7 Proteins 0.000 description 1
- 101000945639 Homo sapiens Cyclin-dependent kinase inhibitor 3 Proteins 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 206010027406 Mesothelioma Diseases 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- LGMSNQNWOCSPIK-LWHGMNCYSA-N alvocidib hydrochloride Chemical compound Cl.O[C@@H]1CN(C)CC[C@@H]1C1=C(O)C=C(O)C2=C1OC(C=1C(=CC=CC=1)Cl)=CC2=O LGMSNQNWOCSPIK-LWHGMNCYSA-N 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 101150059448 cdk7 gene Proteins 0.000 description 1
- 230000006369 cell cycle progression Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 239000002875 cyclin dependent kinase inhibitor Substances 0.000 description 1
- 229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 230000002584 immunomodulator Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 229940043355 kinase inhibitor Drugs 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- -1 methyl- Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 239000003909 protein kinase inhibitor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000002463 transducing effect Effects 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D405/02—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 containing two hetero rings
- C07D405/04—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 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/453—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with oxygen as a ring hetero atom
-
- 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
- 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
- A61P37/02—Immunomodulators
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48781500A | 2000-01-18 | 2000-01-18 | |
| PCT/US2001/000520 WO2001053294A1 (en) | 2000-01-18 | 2001-01-08 | Ethanol solvate of (-)-cis-2-(2-chlorophenyl)-5,7-dihydroxy-8[4r-(3s-hydroxy-1-methyl)piperidinyl]-4h-1-benzopyran-4-one |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20023385D0 NO20023385D0 (no) | 2002-07-12 |
| NO20023385L NO20023385L (no) | 2002-08-27 |
| NO322626B1 true NO322626B1 (no) | 2006-11-06 |
Family
ID=23937213
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20023385A NO322626B1 (no) | 2000-01-18 | 2002-07-12 | Hydroklorid-etanol-solvatform av (-)-cis-2-(2-klorfenyl)-5,7-dihydroksy-8[4R-(3S-hydroksy-1-metyl)piperidinyl]-4H-1-benzopyran-4-on, fremgangsmate for fremstilling derav og anvendelse derav ved behandling av cancer. |
Country Status (26)
| Country | Link |
|---|---|
| EP (1) | EP1252155B1 (cs) |
| JP (1) | JP2003520798A (cs) |
| KR (1) | KR100825530B1 (cs) |
| CN (1) | CN1395577A (cs) |
| AR (1) | AR027226A1 (cs) |
| AT (1) | ATE284400T1 (cs) |
| AU (1) | AU2001230869A1 (cs) |
| BR (1) | BR0107724A (cs) |
| CA (1) | CA2397594C (cs) |
| CZ (1) | CZ301235B6 (cs) |
| DE (1) | DE60107652T2 (cs) |
| DK (1) | DK1252155T3 (cs) |
| EA (1) | EA005182B1 (cs) |
| ES (1) | ES2228800T3 (cs) |
| HU (1) | HU225155B1 (cs) |
| IL (2) | IL150643A0 (cs) |
| MX (1) | MXPA02006965A (cs) |
| NO (1) | NO322626B1 (cs) |
| NZ (1) | NZ520281A (cs) |
| PL (1) | PL201690B1 (cs) |
| PT (1) | PT1252155E (cs) |
| SI (1) | SI1252155T1 (cs) |
| SK (1) | SK287216B6 (cs) |
| TW (1) | TWI293072B (cs) |
| WO (1) | WO2001053294A1 (cs) |
| ZA (1) | ZA200205640B (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109803684B (zh) | 2016-08-23 | 2022-08-23 | 卫材 R&D 管理有限公司 | 用于治疗肝细胞癌的组合疗法 |
| IL269357B1 (en) | 2017-03-16 | 2024-06-01 | Eisai R&D Man Co Ltd | A combination of Era inhibitors and a CDK4/6 inhibitor to be used in a method to treat breast cancer |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN164232B (cs) * | 1986-04-11 | 1989-02-04 | Hoechst India | |
| US5284856A (en) * | 1988-10-28 | 1994-02-08 | Hoechst Aktiengesellschaft | Oncogene-encoded kinases inhibition using 4-H-1-benzopyran-4-one derivatives |
| DE3836676A1 (de) * | 1988-10-28 | 1990-05-03 | Hoechst Ag | Die verwendung von 4h-1-benzopyran-4-on-derivaten, neue 4h-1-benzopyran-4-on-derivate und diese enthaltende arzneimittel |
| US5908934A (en) * | 1996-09-26 | 1999-06-01 | Bristol-Myers Squibb Company | Process for the preparation of chiral ketone intermediates useful for the preparation of flavopiridol and analogs |
-
2001
- 2001-01-08 AU AU2001230869A patent/AU2001230869A1/en not_active Abandoned
- 2001-01-08 DK DK01902993T patent/DK1252155T3/da active
- 2001-01-08 SK SK1037-2002A patent/SK287216B6/sk not_active IP Right Cessation
- 2001-01-08 AT AT01902993T patent/ATE284400T1/de active
- 2001-01-08 PL PL355992A patent/PL201690B1/pl not_active IP Right Cessation
- 2001-01-08 KR KR1020027009140A patent/KR100825530B1/ko not_active IP Right Cessation
- 2001-01-08 MX MXPA02006965A patent/MXPA02006965A/es active IP Right Grant
- 2001-01-08 CA CA2397594A patent/CA2397594C/en not_active Expired - Fee Related
- 2001-01-08 SI SI200130293T patent/SI1252155T1/xx unknown
- 2001-01-08 CZ CZ20022467A patent/CZ301235B6/cs not_active IP Right Cessation
- 2001-01-08 DE DE60107652T patent/DE60107652T2/de not_active Expired - Lifetime
- 2001-01-08 EA EA200200776A patent/EA005182B1/ru not_active IP Right Cessation
- 2001-01-08 WO PCT/US2001/000520 patent/WO2001053294A1/en active IP Right Grant
- 2001-01-08 NZ NZ520281A patent/NZ520281A/en not_active IP Right Cessation
- 2001-01-08 JP JP2001553768A patent/JP2003520798A/ja active Pending
- 2001-01-08 PT PT01902993T patent/PT1252155E/pt unknown
- 2001-01-08 EP EP01902993A patent/EP1252155B1/en not_active Expired - Lifetime
- 2001-01-08 HU HU0204297A patent/HU225155B1/hu not_active IP Right Cessation
- 2001-01-08 BR BR0107724-4A patent/BR0107724A/pt not_active Application Discontinuation
- 2001-01-08 ES ES01902993T patent/ES2228800T3/es not_active Expired - Lifetime
- 2001-01-08 IL IL15064301A patent/IL150643A0/xx unknown
- 2001-01-08 CN CN01803857A patent/CN1395577A/zh active Pending
- 2001-01-17 TW TW090101052A patent/TWI293072B/zh not_active IP Right Cessation
- 2001-01-17 AR ARP010100186A patent/AR027226A1/es not_active Application Discontinuation
-
2002
- 2002-07-08 IL IL150643A patent/IL150643A/en not_active IP Right Cessation
- 2002-07-12 NO NO20023385A patent/NO322626B1/no not_active IP Right Cessation
- 2002-07-15 ZA ZA200205640A patent/ZA200205640B/en unknown
Also Published As
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| Publication | Publication Date | Title |
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