NO327211B1 - Epotiloner med en modifisert sidekjede, samt fremgangsmate for fremstilling derav - Google Patents

Epotiloner med en modifisert sidekjede, samt fremgangsmate for fremstilling derav Download PDF

Info

Publication number: NO327211B1
Authority: NO; Norway
Prior art keywords: meoh; epothilone; epothilones; ddd; solution
Prior art date: 1997-02-25

Application number

NO19994071A

Other languages

English (en)

Norwegian (no)

Other versions

NO994071D0 (no

NO994071L (no

Inventor

Gerhard Hofle

Michael Sefkow

Original Assignee

Biotechnolog Forschung Gmbh

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-02-25

Filing date

1999-08-24

Publication date

2009-05-11

1999-08-24 Application filed by Biotechnolog Forschung Gmbh filed Critical Biotechnolog Forschung Gmbh

1999-08-24 Publication of NO994071D0 publication Critical patent/NO994071D0/no

1999-10-21 Publication of NO994071L publication Critical patent/NO994071L/no

2009-05-11 Publication of NO327211B1 publication Critical patent/NO327211B1/no

Links

229930013356 epothilone Natural products 0.000 title claims abstract description 16
HESCAJZNRMSMJG-KKQRBIROSA-N epothilone A Chemical class C/C([C@@H]1C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(C)=N1 HESCAJZNRMSMJG-KKQRBIROSA-N 0.000 title claims abstract description 15
238000000034 method Methods 0.000 title description 3
-1 Epothilone N-oxide Chemical class 0.000 claims description 8
150000003883 epothilone derivatives Chemical class 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
150000004965 peroxy acids Chemical class 0.000 claims description 3
150000001204 N-oxides Chemical class 0.000 claims description 2
ASQQEOXYFGEFKQ-UHFFFAOYSA-N dioxirane Chemical compound C1OO1 ASQQEOXYFGEFKQ-UHFFFAOYSA-N 0.000 claims description 2
238000007254 oxidation reaction Methods 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 79
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
HESCAJZNRMSMJG-HGYUPSKWSA-N epothilone A Natural products O=C1[C@H](C)[C@H](O)[C@H](C)CCC[C@H]2O[C@H]2C[C@@H](/C(=C\c2nc(C)sc2)/C)OC(=O)C[C@H](O)C1(C)C HESCAJZNRMSMJG-HGYUPSKWSA-N 0.000 description 10
238000005481 NMR spectroscopy Methods 0.000 description 9
239000000203 mixture Substances 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000002474 experimental method Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
239000003480 eluent Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
FCCNKYGSMOSYPV-DEDISHTHSA-N (-)-Epothilone E Natural products O=C1[C@H](C)[C@H](O)[C@@H](C)CCC[C@H]2O[C@H]2C[C@@H](/C(=C\c2nc(CO)sc2)/C)OC(=O)C[C@H](O)C1(C)C FCCNKYGSMOSYPV-DEDISHTHSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
FCCNKYGSMOSYPV-UHFFFAOYSA-N epothilone E Natural products O1C(=O)CC(O)C(C)(C)C(=O)C(C)C(O)C(C)CCCC2OC2CC1C(C)=CC1=CSC(CO)=N1 FCCNKYGSMOSYPV-UHFFFAOYSA-N 0.000 description 2
FCCNKYGSMOSYPV-OKOHHBBGSA-N epothilone e Chemical compound C/C([C@@H]1C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(CO)=N1 FCCNKYGSMOSYPV-OKOHHBBGSA-N 0.000 description 2
239000011888 foil Substances 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
238000002953 preparative HPLC Methods 0.000 description 2
238000000746 purification Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 1
UWKQJZCTQGMHKD-UHFFFAOYSA-N 2,6-di-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=N1 UWKQJZCTQGMHKD-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
101000610640 Homo sapiens U4/U6 small nuclear ribonucleoprotein Prp3 Proteins 0.000 description 1
101001110823 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-A Proteins 0.000 description 1
101000712176 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-B Proteins 0.000 description 1
102100040374 U4/U6 small nuclear ribonucleoprotein Prp3 Human genes 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Plural Heterocyclic Compounds (AREA)
Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Epoxy Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Silicon Polymers (AREA)
Polyesters Or Polycarbonates (AREA)

NO19994071A 1997-02-25 1999-08-24 Epotiloner med en modifisert sidekjede, samt fremgangsmate for fremstilling derav NO327211B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19707505		1997-02-25
PCT/EP1998/001060 WO1998038192A1 (de)	1997-02-25	1998-02-25	Seitenkettenmodifizierte epothilone

Publications (3)

Publication Number	Publication Date
NO994071D0 NO994071D0 (no)	1999-08-24
NO994071L NO994071L (no)	1999-10-21
NO327211B1 true NO327211B1 (no)	2009-05-11

Family

ID=7821415

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19994071A NO327211B1 (no)	1997-02-25	1999-08-24	Epotiloner med en modifisert sidekjede, samt fremgangsmate for fremstilling derav

Country Status (24)

Country	Link
US (1)	US6359140B1 (cs)
EP (2)	EP1201666A3 (cs)
JP (1)	JP2001513098A (cs)
KR (1)	KR100494179B1 (cs)
CN (2)	CN1128803C (cs)
AR (1)	AR011878A1 (cs)
AT (1)	ATE221888T1 (cs)
AU (1)	AU736062B2 (cs)
BR (1)	BR9807742B1 (cs)
CA (1)	CA2281105A1 (cs)
CZ (1)	CZ298027B6 (cs)
DE (2)	DE59805110D1 (cs)
DK (1)	DK0975638T3 (cs)
ES (1)	ES2183338T3 (cs)
HU (1)	HU228851B1 (cs)
IL (1)	IL131343A (cs)
NO (1)	NO327211B1 (cs)
NZ (1)	NZ337195A (cs)
PL (1)	PL190422B1 (cs)
PT (1)	PT975638E (cs)
RU (1)	RU2201932C2 (cs)
TW (1)	TW480263B (cs)
WO (1)	WO1998038192A1 (cs)
ZA (1)	ZA981575B (cs)

Families Citing this family (100)

* Cited by examiner, † Cited by third party
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1998
- 1998-02-25 EP EP02001063A patent/EP1201666A3/de not_active Ceased
- 1998-02-25 CN CN98802842A patent/CN1128803C/zh not_active Expired - Fee Related
- 1998-02-25 DE DE59805110T patent/DE59805110D1/de not_active Expired - Lifetime
- 1998-02-25 JP JP53730098A patent/JP2001513098A/ja not_active Withdrawn
- 1998-02-25 BR BRPI9807742-2A patent/BR9807742B1/pt not_active IP Right Cessation
- 1998-02-25 DE DE19880193T patent/DE19880193D2/de not_active Expired - Lifetime
- 1998-02-25 AT AT98912388T patent/ATE221888T1/de active
- 1998-02-25 WO PCT/EP1998/001060 patent/WO1998038192A1/de not_active Ceased
- 1998-02-25 DK DK98912388T patent/DK0975638T3/da active
- 1998-02-25 AU AU67249/98A patent/AU736062B2/en not_active Ceased
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- 1998-02-25 CA CA002281105A patent/CA2281105A1/en not_active Abandoned
- 1998-02-25 PT PT98912388T patent/PT975638E/pt unknown
- 1998-02-25 ES ES98912388T patent/ES2183338T3/es not_active Expired - Lifetime
- 1998-02-25 KR KR10-1999-7007773A patent/KR100494179B1/ko not_active Expired - Fee Related
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- 1998-02-25 CN CNA031597866A patent/CN1544436A/zh active Pending
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- 1998-05-28 TW TW087102758A patent/TW480263B/zh not_active IP Right Cessation
1999
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Also Published As

Publication number	Publication date
WO1998038192A1 (de)	1998-09-03
AR011878A1 (es)	2000-09-13
EP0975638A1 (de)	2000-02-02
JP2001513098A (ja)	2001-08-28
PL190422B1 (pl)	2005-12-30
NZ337195A (en)	2001-05-25
HUP0002189A3 (en)	2001-12-28
AU736062B2 (en)	2001-07-26
ATE221888T1 (de)	2002-08-15
CN1128803C (zh)	2003-11-26
TW480263B (en)	2002-03-21
NO994071D0 (no)	1999-08-24
HUP0002189A2 (hu)	2001-10-28
EP0975638B1 (de)	2002-08-07
BR9807742A (pt)	2000-02-22
KR100494179B1 (ko)	2005-06-10
ES2183338T3 (es)	2003-03-16
AU6724998A (en)	1998-09-18
IL131343A (en)	2004-03-28
HU228851B1 (en)	2013-06-28
HK1023774A1 (en)	2000-09-22
CA2281105A1 (en)	1998-09-03
DK0975638T3 (da)	2002-11-18
EP1201666A3 (de)	2003-03-05
EP1201666A2 (de)	2002-05-02
CN1248974A (zh)	2000-03-29
DE19880193D2 (de)	2000-08-24
CZ286599A3 (cs)	2000-03-15
DE59805110D1 (de)	2002-09-12
US6359140B1 (en)	2002-03-19
PT975638E (pt)	2002-12-31
CZ298027B6 (cs)	2007-05-30
BR9807742B1 (pt)	2010-12-14
ZA981575B (en)	1998-09-08
RU2201932C2 (ru)	2003-04-10
IL131343A0 (en)	2001-01-28
CN1544436A (zh)	2004-11-10
NO994071L (no)	1999-10-21
PL335329A1 (en)	2000-04-25
KR20000075705A (ko)	2000-12-26

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2018-03-12	MK1K	Patent expired

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