JP2013518093A - テムシロリムスの製造のための改善された方法およびその中間体 - Google Patents
テムシロリムスの製造のための改善された方法およびその中間体 Download PDFInfo
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- JP2013518093A JP2013518093A JP2012550526A JP2012550526A JP2013518093A JP 2013518093 A JP2013518093 A JP 2013518093A JP 2012550526 A JP2012550526 A JP 2012550526A JP 2012550526 A JP2012550526 A JP 2012550526A JP 2013518093 A JP2013518093 A JP 2013518093A
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- 238000000034 method Methods 0.000 title claims abstract description 38
- 229960000235 temsirolimus Drugs 0.000 title claims abstract description 34
- QFJCIRLUMZQUOT-UHFFFAOYSA-N temsirolimus Natural products C1CC(O)C(OC)CC1CC(C)C1OC(=O)C2CCCCN2C(=O)C(=O)C(O)(O2)C(C)CCC2CC(OC)C(C)=CC=CC=CC(C)CC(C)C(=O)C(OC)C(O)C(C)=CC(C)C(=O)C1 QFJCIRLUMZQUOT-UHFFFAOYSA-N 0.000 title claims abstract description 33
- CBPNZQVSJQDFBE-FUXHJELOSA-N Temsirolimus Chemical compound C1C[C@@H](OC(=O)C(C)(CO)CO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 CBPNZQVSJQDFBE-FUXHJELOSA-N 0.000 title claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 21
- 239000000543 intermediate Substances 0.000 title abstract description 17
- 150000001875 compounds Chemical class 0.000 claims description 92
- 238000006243 chemical reaction Methods 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 30
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 claims description 18
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 claims description 18
- 229960002930 sirolimus Drugs 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 15
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 239000007822 coupling agent Substances 0.000 claims description 11
- -1 3-dimethylaminopropyl Chemical group 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 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 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 230000003197 catalytic effect Effects 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 5
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 claims description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000008282 halocarbons Chemical class 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 238000002360 preparation method Methods 0.000 abstract description 4
- 229940034982 antineoplastic agent Drugs 0.000 abstract description 3
- 239000002246 antineoplastic agent Substances 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 7
- 239000002002 slurry Substances 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- NNHYAHOTXLASEA-UHFFFAOYSA-N 1-(dimethoxymethyl)-4-methoxybenzene Chemical compound COC(OC)C1=CC=C(OC)C=C1 NNHYAHOTXLASEA-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- OWCLNFLYOXUNAG-UHFFFAOYSA-N 4-(dimethoxymethyl)-1-methoxy-2-methylbenzene Chemical compound COC(OC)C1=CC=C(OC)C(C)=C1 OWCLNFLYOXUNAG-UHFFFAOYSA-N 0.000 description 2
- HFGHRUCCKVYFKL-UHFFFAOYSA-N 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5h-pyrimido[5,4-b]indole Chemical compound C1=C2NC=3C(OCC)=NC(N4CCNCC4)=NC=3C2=CC=C1C1=CC=NC=C1 HFGHRUCCKVYFKL-UHFFFAOYSA-N 0.000 description 2
- MYLBIQHZWFWSMH-UHFFFAOYSA-N 4-methoxy-3-methylbenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1C MYLBIQHZWFWSMH-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- AYOOGWWGECJQPI-NSHDSACASA-N n-[(1s)-1-(5-fluoropyrimidin-2-yl)ethyl]-3-(3-propan-2-yloxy-1h-pyrazol-5-yl)imidazo[4,5-b]pyridin-5-amine Chemical compound N1C(OC(C)C)=CC(N2C3=NC(N[C@@H](C)C=4N=CC(F)=CN=4)=CC=C3N=C2)=N1 AYOOGWWGECJQPI-NSHDSACASA-N 0.000 description 2
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- OZITYEIPCBXMSE-UHFFFAOYSA-N 2-(4-methoxy-3-methylphenyl)-5-methyl-1,3-dioxane-5-carboxylic acid Chemical compound C1=C(C)C(OC)=CC=C1C1OCC(C)(C(O)=O)CO1 OZITYEIPCBXMSE-UHFFFAOYSA-N 0.000 description 1
- KGWLYWQUODVETH-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5-methyl-1,3-dioxane-5-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1OCC(C)(C(O)=O)CO1 KGWLYWQUODVETH-UHFFFAOYSA-N 0.000 description 1
- DBXBTMSZEOQQDU-UHFFFAOYSA-N 3-hydroxyisobutyric acid Chemical compound OCC(C)C(O)=O DBXBTMSZEOQQDU-UHFFFAOYSA-N 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N Anisaldehyde Natural products COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- 208000006265 Renal cell carcinoma Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UILHLFXNKWUQCU-UHFFFAOYSA-N [2-(4-methoxy-3-methylphenyl)-5-methyl-1,3-dioxane-5-carbonyl] 2-(4-methoxy-3-methylphenyl)-5-methyl-1,3-dioxane-5-carboxylate Chemical compound C1=C(C)C(OC)=CC=C1C1OCC(C)(C(=O)OC(=O)C2(C)COC(OC2)C=2C=C(C)C(OC)=CC=2)CO1 UILHLFXNKWUQCU-UHFFFAOYSA-N 0.000 description 1
- MDJJHKQGXRGGHG-UHFFFAOYSA-N [2-(4-methoxyphenyl)-5-methyl-1,3-dioxane-5-carbonyl] 2-(4-methoxyphenyl)-5-methyl-1,3-dioxane-5-carboxylate Chemical compound C1=CC(OC)=CC=C1C1OCC(C)(C(=O)OC(=O)C2(C)COC(OC2)C=2C=CC(OC)=CC=2)CO1 MDJJHKQGXRGGHG-UHFFFAOYSA-N 0.000 description 1
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 229940123729 mTOR kinase inhibitor Drugs 0.000 description 1
- 239000003628 mammalian target of rapamycin inhibitor Substances 0.000 description 1
- VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/18—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN173/DEL/2010 | 2010-01-28 | ||
| IN173DE2010 | 2010-01-28 | ||
| PCT/IB2011/000084 WO2011092564A2 (en) | 2010-01-28 | 2011-01-20 | Process for the preparation of temsirolimus and its intermediates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013518093A true JP2013518093A (ja) | 2013-05-20 |
| JP2013518093A5 JP2013518093A5 (enExample) | 2014-03-06 |
Family
ID=44022850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012550526A Pending JP2013518093A (ja) | 2010-01-28 | 2011-01-20 | テムシロリムスの製造のための改善された方法およびその中間体 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8524893B2 (enExample) |
| EP (1) | EP2528906A2 (enExample) |
| JP (1) | JP2013518093A (enExample) |
| AU (1) | AU2011210227A1 (enExample) |
| WO (1) | WO2011092564A2 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102020662B (zh) * | 2011-01-07 | 2013-02-13 | 天津市炜杰科技有限公司 | 一种驮瑞塞尔制备方法 |
| CN102807571A (zh) * | 2012-05-25 | 2012-12-05 | 上海现代制药股份有限公司 | 一种适于工业化生产坦西莫司的制备方法 |
| CN108948047A (zh) * | 2017-05-20 | 2018-12-07 | 鲁南制药集团股份有限公司 | 一种替西罗莫司的纯化方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995028406A1 (en) * | 1994-04-18 | 1995-10-26 | American Home Products Corporation | Rapamycin hydroxyesters, process for their preparation and pharmaceutical compositions containing them |
| WO2001023395A2 (en) * | 1999-09-29 | 2001-04-05 | American Home Products Corporation | Regioselective synthesis of rapamycin derivatives |
| WO2002026867A2 (en) * | 2000-09-29 | 2002-04-04 | The Regents Of The University Of California | Dendrimeric support or carrier macromolecule |
| WO2005016935A2 (en) * | 2003-08-07 | 2005-02-24 | Wyeth | Regioselective synthesis of cci-779 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE510128C2 (sv) * | 1997-06-26 | 1999-04-19 | Perstorp Ab | Förfarande för framställning av dendritisk polyol |
| US6277983B1 (en) | 2000-09-27 | 2001-08-21 | American Home Products Corporation | Regioselective synthesis of rapamycin derivatives |
| TW201035104A (en) | 2009-03-27 | 2010-10-01 | Chunghwa Chemical Synthesis & Biotech Co Ltd | Improved synthesis method for Temsirolimus and its similar compounds |
-
2011
- 2011-01-20 EP EP11713345A patent/EP2528906A2/en not_active Withdrawn
- 2011-01-20 JP JP2012550526A patent/JP2013518093A/ja active Pending
- 2011-01-20 WO PCT/IB2011/000084 patent/WO2011092564A2/en not_active Ceased
- 2011-01-20 AU AU2011210227A patent/AU2011210227A1/en not_active Abandoned
- 2011-01-28 US US13/016,235 patent/US8524893B2/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995028406A1 (en) * | 1994-04-18 | 1995-10-26 | American Home Products Corporation | Rapamycin hydroxyesters, process for their preparation and pharmaceutical compositions containing them |
| WO2001023395A2 (en) * | 1999-09-29 | 2001-04-05 | American Home Products Corporation | Regioselective synthesis of rapamycin derivatives |
| WO2002026867A2 (en) * | 2000-09-29 | 2002-04-04 | The Regents Of The University Of California | Dendrimeric support or carrier macromolecule |
| WO2005016935A2 (en) * | 2003-08-07 | 2005-02-24 | Wyeth | Regioselective synthesis of cci-779 |
Non-Patent Citations (3)
| Title |
|---|
| JPN5013004215; Ｈ ＩＨＲＥ: 'ＦＡＳＴ ＡＮＤ ＣＯＮＶＥＮＩＥＮＴ ＤＩＶＥＲＧＥＮＴ ＳＹＮＴＨＥＳＩＳ ＯＦ ＡＬＩＰＨＡＴＩＣ ＥＳＴＥＲ ＤＥＮＤＲＩＭＥＲＳ ＢＹ ＡＮＨＹＤＲＩＤＥ ＣＯＵＰＬＩＮＧ' Ｊ．ＡＭ．ＣＨＥＭ．ＳＯＣ Ｖ１２３ Ｎ２５, 2001, Ｐ５９０８-５９１７ * |
| JPN6014047242; Ｐｏｌｙｍｅｒ ４９, 2008, １１９９-１２１０ * |
| JPN6014047245; ＰＲＯＴＥＣＴＩＶＥ ＧＲＯＵＰＳ ＩＮ ＯＲＧＡＮＩＣ ＳＹＮＴＨＥＳＩＳ． ３ｒｄ Ｅｄ．, 1999, ２０１-２３１， ２４２-２４５ * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011092564A8 (en) | 2012-09-13 |
| WO2011092564A3 (en) | 2011-12-01 |
| US8524893B2 (en) | 2013-09-03 |
| WO2011092564A4 (en) | 2012-01-19 |
| EP2528906A2 (en) | 2012-12-05 |
| WO2011092564A2 (en) | 2011-08-04 |
| US20110184167A1 (en) | 2011-07-28 |
| AU2011210227A1 (en) | 2012-08-30 |
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