NO332250B1 - Taksanderivater funksjonalisert pa den 14.posisjon og en fremgangsmate for fremstilling derav - Google Patents
Taksanderivater funksjonalisert pa den 14.posisjon og en fremgangsmate for fremstilling derav Download PDFInfo
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- NO332250B1 NO332250B1 NO20051774A NO20051774A NO332250B1 NO 332250 B1 NO332250 B1 NO 332250B1 NO 20051774 A NO20051774 A NO 20051774A NO 20051774 A NO20051774 A NO 20051774A NO 332250 B1 NO332250 B1 NO 332250B1
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- arom
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- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 title description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 80
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 9
- 125000006239 protecting group Chemical group 0.000 claims abstract description 7
- 230000009467 reduction Effects 0.000 claims abstract description 6
- 238000003776 cleavage reaction Methods 0.000 claims abstract description 4
- 230000007017 scission Effects 0.000 claims abstract description 4
- 125000003277 amino group Chemical group 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 230000032050 esterification Effects 0.000 claims description 7
- 238000005886 esterification reaction Methods 0.000 claims description 7
- -1 3-thienoyl Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- HOJZAHQWDXAPDJ-UHFFFAOYSA-N 3-anilino-2-hydroxypropanoic acid Chemical group OC(=O)C(O)CNC1=CC=CC=C1 HOJZAHQWDXAPDJ-UHFFFAOYSA-N 0.000 claims description 2
- GZLMFCWSEKVVGO-UHFFFAOYSA-N 3-azaniumyl-2-hydroxy-5-methylhexanoate Chemical group CC(C)CC(N)C(O)C(O)=O GZLMFCWSEKVVGO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 5
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 abstract description 3
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- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract description 2
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- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 106
- 239000000243 solution Substances 0.000 description 103
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 82
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 64
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 48
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- 101150041968 CDC13 gene Proteins 0.000 description 38
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 38
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- 230000002829 reductive effect Effects 0.000 description 32
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- 238000003756 stirring Methods 0.000 description 31
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 19
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- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 14
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
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- 239000012043 crude product Substances 0.000 description 9
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 7
- 239000012346 acetyl chloride Substances 0.000 description 7
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- NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
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- NQZKZGHOYUYCHU-UHFFFAOYSA-N boron;tetraethylazanium Chemical compound [B].CC[N+](CC)(CC)CC NQZKZGHOYUYCHU-UHFFFAOYSA-N 0.000 description 2
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- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
- KQIADDMXRMTWHZ-UHFFFAOYSA-N chloro-tri(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(C(C)C)C(C)C KQIADDMXRMTWHZ-UHFFFAOYSA-N 0.000 description 2
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- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
- IKYOVSVBLHGFMA-UHFFFAOYSA-N dipyridin-2-yloxymethanethione Chemical compound C=1C=CC=NC=1OC(=S)OC1=CC=CC=N1 IKYOVSVBLHGFMA-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 229960003668 docetaxel Drugs 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000000457 gamma-lactone group Chemical group 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000011445 neoadjuvant hormone therapy Methods 0.000 description 1
- 230000009826 neoplastic cell growth Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 150000004843 oxaziridines Chemical class 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QKSQWQOAUQFORH-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C QKSQWQOAUQFORH-UHFFFAOYSA-N 0.000 description 1
- ISHLCKAQWKBMAU-UHFFFAOYSA-N tert-butyl n-diazocarbamate Chemical compound CC(C)(C)OC(=O)N=[N+]=[N-] ISHLCKAQWKBMAU-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 125000006248 tosyl amino group Chemical group [H]N(*)S(=O)(=O)C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT001921A ITMI20021921A1 (it) | 2002-09-10 | 2002-09-10 | Funzionalizzazione della posizione 14 dei nuclei tassanici e sintesi di nuovi derivati antitumorali. |
| PCT/EP2003/009866 WO2004024706A2 (en) | 2002-09-10 | 2003-09-05 | Taxane derivatives functionalized at the 14- position and a process for the preparation thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20051774L NO20051774L (no) | 2005-05-10 |
| NO332250B1 true NO332250B1 (no) | 2012-08-06 |
Family
ID=31986024
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20051774A NO332250B1 (no) | 2002-09-10 | 2005-04-11 | Taksanderivater funksjonalisert pa den 14.posisjon og en fremgangsmate for fremstilling derav |
| NO20110782A NO332367B1 (no) | 2002-09-10 | 2011-05-30 | Taksanderivater funksjonalisert pa den 14. posisjonen |
| NO20110781A NO332366B1 (no) | 2002-09-10 | 2011-05-30 | Taksanderivater funksjonalisert pa den 14. posisjon og en fremgangsmate for fremstilling derav |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20110782A NO332367B1 (no) | 2002-09-10 | 2011-05-30 | Taksanderivater funksjonalisert pa den 14. posisjonen |
| NO20110781A NO332366B1 (no) | 2002-09-10 | 2011-05-30 | Taksanderivater funksjonalisert pa den 14. posisjon og en fremgangsmate for fremstilling derav |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7498452B2 (de) |
| EP (6) | EP1980557A3 (de) |
| JP (2) | JP4690039B2 (de) |
| KR (1) | KR101096918B1 (de) |
| CN (1) | CN1681799A (de) |
| AT (1) | ATE398113T1 (de) |
| AU (1) | AU2003267049B8 (de) |
| CA (1) | CA2498277C (de) |
| DE (1) | DE60321577D1 (de) |
| DK (4) | DK2077264T3 (de) |
| ES (4) | ES2398324T3 (de) |
| IL (5) | IL167336A (de) |
| IT (1) | ITMI20021921A1 (de) |
| NO (3) | NO332250B1 (de) |
| PL (4) | PL402333A1 (de) |
| PT (4) | PT2264019E (de) |
| RU (1) | RU2320652C2 (de) |
| SG (1) | SG164282A1 (de) |
| SI (4) | SI2264019T1 (de) |
| WO (1) | WO2004024706A2 (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20012185A1 (it) * | 2001-10-19 | 2003-04-19 | Indena Spa | Procedimento per la preparazione della 14beta-idrossi-baccatina iii-1,14-carbonato |
| CN107056767B (zh) * | 2015-12-04 | 2022-07-15 | 江苏恩华络康药物研发有限公司 | 用于制备水溶性紫杉烷类衍生物的方法及中间体 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5504222A (en) | 1993-08-20 | 1996-04-02 | The Scripps Research Institute | Transformations of taxol |
| IL108444A0 (en) * | 1993-01-29 | 1994-04-12 | Univ Florida State | C2 taxane derivatives and pharmaceutical compositions containing them |
| US5475011A (en) * | 1993-03-26 | 1995-12-12 | The Research Foundation Of State University Of New York | Anti-tumor compounds, pharmaceutical compositions, methods for preparation thereof and for treatment |
| IL127599A (en) | 1994-01-28 | 2004-06-01 | Upjohn Co | Process for preparing isotaxol analogs |
| US5719177A (en) | 1994-11-04 | 1998-02-17 | Pharmacia S.P.A. | Taxane derivatives |
| IT1275936B1 (it) * | 1995-03-17 | 1997-10-24 | Indena Spa | Derivati della 10-deacetilbaccatina iii e della 10-deacetil-14b- idrossibaccatina iii loro metodo di preparazione e formulazioni |
| US5811452A (en) * | 1997-01-08 | 1998-09-22 | The Research Foundation Of State University Of New York | Taxoid reversal agents for drug-resistance in cancer chemotherapy and pharmaceutical compositions thereof |
| ITMI991483A1 (it) * | 1999-07-06 | 2001-01-06 | Indena Spa | Derivati tassanici e procedimenti per la loro preparazione |
| JP2004506069A (ja) * | 2000-08-04 | 2004-02-26 | センサーズ・フォー・メデセン・アンド・サイエンス・インコーポレーテッド | 水性環境中での検体検出 |
| IT1318678B1 (it) | 2000-08-10 | 2003-08-27 | Indena Spa | Procedimento per la preparazione di derivati della baccatina iii. |
| ITMI20012186A1 (it) * | 2001-10-19 | 2003-04-19 | Indena Spa | Procedimento per la preparazione della 14-beta-idrossi-baccatina iii-1,14-carbonato |
-
2002
- 2002-09-10 IT IT001921A patent/ITMI20021921A1/it unknown
-
2003
- 2003-09-05 SI SI200332292T patent/SI2264019T1/sl unknown
- 2003-09-05 US US10/527,164 patent/US7498452B2/en not_active Expired - Fee Related
- 2003-09-05 EP EP08157617A patent/EP1980557A3/de not_active Withdrawn
- 2003-09-05 DK DK09155673.8T patent/DK2077264T3/da active
- 2003-09-05 ES ES09155673T patent/ES2398324T3/es not_active Expired - Lifetime
- 2003-09-05 EP EP10177332A patent/EP2281820A3/de not_active Withdrawn
- 2003-09-05 SG SG200703232-9A patent/SG164282A1/en unknown
- 2003-09-05 EP EP10177329.9A patent/EP2264019B1/de not_active Expired - Lifetime
- 2003-09-05 PL PL402333A patent/PL402333A1/pl unknown
- 2003-09-05 CN CNA038213389A patent/CN1681799A/zh active Pending
- 2003-09-05 DK DK03747971T patent/DK1537093T3/da active
- 2003-09-05 KR KR1020057003994A patent/KR101096918B1/ko not_active IP Right Cessation
- 2003-09-05 PL PL03375625A patent/PL375625A1/xx unknown
- 2003-09-05 PT PT101773299T patent/PT2264019E/pt unknown
- 2003-09-05 WO PCT/EP2003/009866 patent/WO2004024706A2/en active Application Filing
- 2003-09-05 SI SI200332239T patent/SI2077264T1/sl unknown
- 2003-09-05 DK DK10177326.5T patent/DK2298754T3/da active
- 2003-09-05 ES ES10177329T patent/ES2432024T3/es not_active Expired - Lifetime
- 2003-09-05 ES ES10177326T patent/ES2433580T3/es not_active Expired - Lifetime
- 2003-09-05 CA CA2498277A patent/CA2498277C/en not_active Expired - Fee Related
- 2003-09-05 SI SI200331276T patent/SI1537093T1/sl unknown
- 2003-09-05 PT PT91556738T patent/PT2077264E/pt unknown
- 2003-09-05 PT PT101773265T patent/PT2298754E/pt unknown
- 2003-09-05 EP EP10177326.5A patent/EP2298754B9/de not_active Expired - Lifetime
- 2003-09-05 ES ES03747971T patent/ES2307965T3/es not_active Expired - Lifetime
- 2003-09-05 PT PT03747971T patent/PT1537093E/pt unknown
- 2003-09-05 DK DK10177329.9T patent/DK2264019T3/da active
- 2003-09-05 EP EP09155673A patent/EP2077264B1/de not_active Expired - Lifetime
- 2003-09-05 PL PL402323A patent/PL402323A1/pl unknown
- 2003-09-05 DE DE60321577T patent/DE60321577D1/de not_active Expired - Lifetime
- 2003-09-05 SI SI200332306T patent/SI2298754T1/sl unknown
- 2003-09-05 AU AU2003267049A patent/AU2003267049B8/en not_active Ceased
- 2003-09-05 AT AT03747971T patent/ATE398113T1/de active
- 2003-09-05 RU RU2005106361/04A patent/RU2320652C2/ru not_active IP Right Cessation
- 2003-09-05 EP EP03747971A patent/EP1537093B1/de not_active Expired - Lifetime
- 2003-09-05 JP JP2004535440A patent/JP4690039B2/ja not_active Expired - Fee Related
- 2003-09-05 PL PL402332A patent/PL402332A1/pl unknown
-
2005
- 2005-03-09 IL IL167336A patent/IL167336A/en not_active IP Right Cessation
- 2005-04-11 NO NO20051774A patent/NO332250B1/no not_active IP Right Cessation
-
2009
- 2009-03-26 IL IL197815A patent/IL197815A/en not_active IP Right Cessation
-
2010
- 2010-07-30 JP JP2010172650A patent/JP2010270145A/ja active Pending
-
2011
- 2011-05-30 NO NO20110782A patent/NO332367B1/no not_active IP Right Cessation
- 2011-05-30 NO NO20110781A patent/NO332366B1/no not_active IP Right Cessation
- 2011-08-03 IL IL214432A patent/IL214432A/en not_active IP Right Cessation
- 2011-08-03 IL IL214430A patent/IL214430A0/en unknown
- 2011-08-03 IL IL214431A patent/IL214431A/en not_active IP Right Cessation
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| MM1K | Lapsed by not paying the annual fees |