NO310557B1 - Fremgangsmåte ved fremstilling av Ginkgolid B fra Ginkgolid C - Google Patents

Fremgangsmåte ved fremstilling av Ginkgolid B fra Ginkgolid C Download PDF

Info

Publication number: NO310557B1
Authority: NO; Norway
Prior art keywords: ginkgolide; borohydride; group; reaction; carried out
Prior art date: 1994-04-22

Application number

NO19951524A

Other languages

English (en)

Norwegian (no)

Other versions

NO951524L (no

NO951524D0 (no

Inventor

Jean-Bernard Cazaux

Michel Dafniet

Jacques Rebollo

Beng-Poon Teng

Original Assignee

Sod Conseils Rech Applic

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.)

1994-04-22

Filing date

1995-04-21

Publication date

2001-07-23

1995-04-21 Application filed by Sod Conseils Rech Applic filed Critical Sod Conseils Rech Applic

1995-04-21 Publication of NO951524D0 publication Critical patent/NO951524D0/no

1995-10-23 Publication of NO951524L publication Critical patent/NO951524L/no

2001-07-23 Publication of NO310557B1 publication Critical patent/NO310557B1/no

Links

AMOGMTLMADGEOQ-DPFZUGDXSA-N ginkgolide C Natural products O=C1[C@@H](C)[C@]2(O)[C@H]([C@H](O)[C@@]34[C@H]5[C@H](O)[C@@H](C(C)(C)C)[C@]63[C@H](O)C(=O)O[C@H]6O[C@@]24C(=O)O5)O1 AMOGMTLMADGEOQ-DPFZUGDXSA-N 0.000 title claims description 24
238000000034 method Methods 0.000 title claims description 23
SQOJOAFXDQDRGF-NNGCZKEZSA-N ginkgolide B Chemical compound C12([C@H](C(C)(C)C)C[C@H]3OC4=O)[C@@H](O)C(=O)O[C@H]1O[C@]14C23[C@@H](O)[C@@H]2OC(=O)[C@@H](C)[C@]12O SQOJOAFXDQDRGF-NNGCZKEZSA-N 0.000 title 1
SQOJOAFXDQDRGF-MMQTXUMRSA-N ginkgolide-b Chemical compound O[C@H]([C@]12[C@H](C(C)(C)C)C[C@H]3OC4=O)C(=O)O[C@H]2O[C@]24[C@@]13[C@@H](O)[C@@H]1OC(=O)[C@@H](C)[C@]21O SQOJOAFXDQDRGF-MMQTXUMRSA-N 0.000 claims abstract description 24
SQOJOAFXDQDRGF-WJHVHIKBSA-N ginkgolide B Natural products O=C1[C@@H](C)[C@@]2(O)[C@@H]([C@H](O)[C@]34[C@@H]5OC(=O)[C@]23O[C@H]2OC(=O)[C@H](O)[C@@]42[C@H](C(C)(C)C)C5)O1 SQOJOAFXDQDRGF-WJHVHIKBSA-N 0.000 claims abstract description 23
239000000010 aprotic solvent Substances 0.000 claims abstract description 4
150000008064 anhydrides Chemical class 0.000 claims abstract description 3
AMOGMTLMADGEOQ-FNZROXQESA-N Ginkgolide C Chemical compound O([C@H]1O2)C(=O)[C@H](O)C31[C@]14[C@@H](O)[C@@H]5OC(=O)[C@@H](C)[C@]5(O)[C@@]12C(=O)O[C@@H]4[C@@H](O)[C@H]3C(C)(C)C AMOGMTLMADGEOQ-FNZROXQESA-N 0.000 claims description 24
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 4
150000001340 alkali metals Chemical group 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical group CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 4
125000001894 2,4,6-trinitrophenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O 0.000 claims description 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
150000003863 ammonium salts Chemical class 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
125000005207 tetraalkylammonium group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
229930184727 ginkgolide Natural products 0.000 abstract description 8
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
-1 diterpene lactones Chemical class 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
235000008100 Ginkgo biloba Nutrition 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
238000000605 extraction Methods 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
MLSGSTVEFFOWLW-UHFFFAOYSA-N (2,4,6-trinitrophenyl)sulfonyl 2,4,6-trinitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1S(=O)(=O)OS(=O)(=O)C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O MLSGSTVEFFOWLW-UHFFFAOYSA-N 0.000 description 1
VPAHTUQECJIGCK-UHFFFAOYSA-N (2-methylphenyl)sulfonyl 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S(=O)(=O)OS(=O)(=O)C1=CC=CC=C1C VPAHTUQECJIGCK-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
235000011201 Ginkgo Nutrition 0.000 description 1
241000218628 Ginkgo Species 0.000 description 1
244000194101 Ginkgo biloba Species 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
MLWPJXZKQOPTKZ-UHFFFAOYSA-N benzenesulfonyl benzenesulfonate Chemical compound C=1C=CC=CC=1S(=O)(=O)OS(=O)(=O)C1=CC=CC=C1 MLWPJXZKQOPTKZ-UHFFFAOYSA-N 0.000 description 1
QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000006392 deoxygenation reaction Methods 0.000 description 1
229930004069 diterpene Natural products 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
SCHZCUMIENIQMY-UHFFFAOYSA-N tris(trimethylsilyl)silicon Chemical compound C[Si](C)(C)[Si]([Si](C)(C)C)[Si](C)(C)C SCHZCUMIENIQMY-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicines Containing Plant Substances (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO19951524A 1994-04-22 1995-04-21 Fremgangsmåte ved fremstilling av Ginkgolid B fra Ginkgolid C NO310557B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB9408044A GB9408044D0 (en)	1994-04-22	1994-04-22	Conversion of ginkgolide c to ginkgolide b

Publications (3)

Publication Number	Publication Date
NO951524D0 NO951524D0 (no)	1995-04-21
NO951524L NO951524L (no)	1995-10-23
NO310557B1 true NO310557B1 (no)	2001-07-23

Family

ID=10753985

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19951524A NO310557B1 (no)	1994-04-22	1995-04-21	Fremgangsmåte ved fremstilling av Ginkgolid B fra Ginkgolid C

Country Status (23)

Country	Link
US (1)	US5599950A (da)
EP (1)	EP0680968B1 (da)
JP (1)	JP2992575B2 (da)
KR (1)	KR950032203A (da)
AT (1)	ATE189817T1 (da)
AU (1)	AU684338B2 (da)
CA (1)	CA2147423C (da)
DE (1)	DE69515077T2 (da)
DK (1)	DK0680968T3 (da)
DZ (1)	DZ1874A1 (da)
ES (1)	ES2144585T3 (da)
FI (1)	FI109907B (da)
FR (1)	FR2719046B1 (da)
GB (2)	GB9408044D0 (da)
IE (1)	IE80950B1 (da)
MY (1)	MY113056A (da)
NO (1)	NO310557B1 (da)
NZ (1)	NZ270925A (da)
OA (1)	OA10145A (da)
RU (1)	RU2145326C1 (da)
TN (1)	TNSN95041A1 (da)
TW (1)	TW300897B (da)
ZA (1)	ZA952986B (da)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5981902A (en) *	1994-12-15	1999-11-09	Mitsubishi Chemical Corporation	Texturing apparatus for magnetic recording medium and magnetic recording medium process thereby
AU4822597A (en) *	1996-10-16	1998-05-11	Merck & Co., Inc.	Triterpene derivatives with immunosuppressant activity
WO1998016531A1 (en) *	1996-10-16	1998-04-23	Merck & Co., Inc.	Triterpene derivatives with immunosupressant activity
US6100293A (en) *	1997-10-17	2000-08-08	Merck & Co., Inc.	Tetracyclic triterpene derivatives with immunosuppressant activity
US6083980A (en) *	1997-10-17	2000-07-04	Merck & Co., Inc.	Furanyl, tetracyclic triterpene derivatives with immunosuppressant activity
US6022890A (en) *	1997-11-14	2000-02-08	Merck & Co., Inc.	Immunosuppressant tetracyclic triterpenes
US6030621A (en)	1998-03-19	2000-02-29	De Long; Xie	Ginkgo biloba composition, method to prepare the same and uses thereof
US6051590A (en) *	1999-05-13	2000-04-18	Merck & Co., Inc.	Immunosuppressant tricyclic compounds
US7238514B2 (en) *	2001-01-05	2007-07-03	William Marsh Rice University	Diterpene-producing unicellular organism
US6946283B2 (en) *	2001-01-05	2005-09-20	William Marsh Rice University	Ginkgo biloba levopimaradiene synthase
FR2823116B1 (fr) *	2001-04-10	2004-11-19	Sod Conseils Rech Applic	Procede de preparation d'une extrait de feuilles de ginkgo biloba hautement enrichi en principes actifs
US6693091B2 (en)	2002-03-29	2004-02-17	The Trustees Of Columbia University In The City Of New York	Analogs of terpene trilactones from Ginkgo biloba for bioorganic and imaging studies
WO2003082185A2 (en) *	2002-03-29	2003-10-09	The Trustees Of Columbia University In The City Of New York	Analogs of terpene trilactones from ginkgo biloba and related compounds and uses thereof
WO2005021496A2 (en) *	2003-08-27	2005-03-10	The Trustees Of Columbia University In The City Of New York	Synthesis of derivatives of ginkgolide c
WO2005046829A2 (en)	2003-11-12	2005-05-26	The Trustees Of Columbia University In The City Of New York	Separation of ginkgolides and bilobalide from g. biloba
WO2005092324A1 (en) *	2004-03-19	2005-10-06	The Trustees Of Columbia University In The City Of New York	Ginkgolide compounds, compositions, extracts, and uses thereof
WO2006083366A2 (en) *	2004-11-23	2006-08-10	The Trustees Of Columbia University In The City Of New York	Preparation of ginkgolide and f-seco-ginkgolide lactols
WO2007002410A2 (en) *	2005-06-22	2007-01-04	The Trustees Of Columbia University In The City Of New York	Core-modified terpene trilactones from ginkgo biloba extract and biological evaluation thereof
CN102382121A (zh) *	2010-09-02	2012-03-21	秦引林	银杏内酯衍生物及其在制药中的应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8418424D0 (en) *	1984-07-19	1984-08-22	Scras	Inhibition of platelets aggregation
IL78621A (en) *	1985-04-30	1991-06-30	American Cyanamid Co	Mylbemycin analogs,their preparation and pesticidal compositions containing them
GB8725871D0 (en) *	1987-11-04	1987-12-09	Scras	Ginkgolide derivatives
KR940002795B1 (ko) *	1989-06-16	1994-04-02	주식회사 선경인더스트리	은행잎에서 징코라이드를 분리 및 정제하는 방법
GB9107425D0 (en) *	1991-04-09	1991-05-22	Scras	Preparation of ginkgolide b

1994
- 1994-04-22 GB GB9408044A patent/GB9408044D0/en active Pending
- 1994-08-04 US US08/287,632 patent/US5599950A/en not_active Expired - Lifetime
1995
- 1995-04-10 IE IE950265A patent/IE80950B1/en not_active IP Right Cessation
- 1995-04-10 TW TW084103406A patent/TW300897B/zh active
- 1995-04-11 ZA ZA952986A patent/ZA952986B/xx unknown
- 1995-04-12 NZ NZ270925A patent/NZ270925A/en not_active IP Right Cessation
- 1995-04-18 GB GB9507801A patent/GB2288599B/en not_active Expired - Fee Related
- 1995-04-19 DZ DZ950042A patent/DZ1874A1/fr active
- 1995-04-20 FR FR9504709A patent/FR2719046B1/fr not_active Expired - Fee Related
- 1995-04-20 DK DK95400876T patent/DK0680968T3/da active
- 1995-04-20 AU AU16566/95A patent/AU684338B2/en not_active Ceased
- 1995-04-20 AT AT95400876T patent/ATE189817T1/de active
- 1995-04-20 MY MYPI95001032A patent/MY113056A/en unknown
- 1995-04-20 DE DE69515077T patent/DE69515077T2/de not_active Expired - Lifetime
- 1995-04-20 CA CA002147423A patent/CA2147423C/en not_active Expired - Fee Related
- 1995-04-20 ES ES95400876T patent/ES2144585T3/es not_active Expired - Lifetime
- 1995-04-20 EP EP95400876A patent/EP0680968B1/fr not_active Expired - Lifetime
- 1995-04-21 RU RU95106678A patent/RU2145326C1/ru not_active IP Right Cessation
- 1995-04-21 NO NO19951524A patent/NO310557B1/no unknown
- 1995-04-21 OA OA60645A patent/OA10145A/fr unknown
- 1995-04-21 KR KR1019950009403A patent/KR950032203A/ko not_active Ceased
- 1995-04-21 JP JP7096757A patent/JP2992575B2/ja not_active Expired - Fee Related
- 1995-04-21 TN TNTNSN95041A patent/TNSN95041A1/fr unknown
- 1995-04-21 FI FI951903A patent/FI109907B/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
FI951903L (fi)	1995-10-23
EP0680968B1 (fr)	2000-02-16
EP0680968A1 (fr)	1995-11-08
AU1656695A (en)	1995-11-02
FR2719046A1 (fr)	1995-10-27
CA2147423A1 (en)	1995-10-23
AU684338B2 (en)	1997-12-11
IE950265A1 (en)	1995-11-01
JP2992575B2 (ja)	1999-12-20
OA10145A (fr)	1996-12-18
GB2288599A (en)	1995-10-25
JPH07291975A (ja)	1995-11-07
US5599950A (en)	1997-02-04
FI951903A0 (fi)	1995-04-21
NZ270925A (en)	1996-03-26
MY113056A (en)	2001-11-30
RU95106678A (ru)	1997-01-10
DE69515077D1 (de)	2000-03-23
KR950032203A (ko)	1995-12-20
FR2719046B1 (fr)	1999-03-19
FI109907B (fi)	2002-10-31
RU2145326C1 (ru)	2000-02-10
NO951524L (no)	1995-10-23
CA2147423C (en)	2005-06-21
DK0680968T3 (da)	2000-07-31
DZ1874A1 (fr)	2002-02-17
DE69515077T2 (de)	2000-09-14
TNSN95041A1 (fr)	1996-02-06
ZA952986B (en)	1995-12-21
TW300897B (da)	1997-03-21
NO951524D0 (no)	1995-04-21
ES2144585T3 (es)	2000-06-16
IE80950B1 (en)	1999-07-14
GB2288599B (en)	1998-04-22
GB9507801D0 (en)	1995-05-31
GB9408044D0 (en)	1994-06-15
ATE189817T1 (de)	2000-03-15

Publication	Publication Date	Title
CA2147423C (en)	2005-06-21	Preparation process of ginkgolide b from ginkgolide c
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