IL106074A - Process for separating anomers of 2-deoxy-2,2-difluoro-D-pantopornosyl alkylsulfonate - Google Patents

Process for separating anomers of 2-deoxy-2,2-difluoro-D-pantopornosyl alkylsulfonate

Info

Publication number: IL106074A
Authority: IL; Israel
Prior art keywords: deoxy; difluoro; ribofuranosyl; benzoyl; methanesulfonate
Prior art date: 1992-06-22

Application number

IL106074A

Other languages

English (en)

Hebrew (he)

Other versions

IL106074A0 (en

Original Assignee

Lilly Co Eli

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.)

1992-06-22

Filing date

1993-06-21

Publication date

1998-02-22

1993-06-21 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1993-10-20 Publication of IL106074A0 publication Critical patent/IL106074A0/xx

1998-02-22 Publication of IL106074A publication Critical patent/IL106074A/en

Links

238000000034 method Methods 0.000 title claims abstract description 21
150000008052 alkyl sulfonates Chemical class 0.000 title description 2
239000000203 mixture Substances 0.000 claims abstract description 39
239000002904 solvent Substances 0.000 claims abstract description 10
238000010438 heat treatment Methods 0.000 claims abstract description 3
239000013078 crystal Substances 0.000 claims description 29
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 15
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 4
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 4
229940090181 propyl acetate Drugs 0.000 claims description 4
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
239000008096 xylene Substances 0.000 claims description 4
229940072049 amyl acetate Drugs 0.000 claims description 3
PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 3
MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000000547 substituted alkyl group Chemical group 0.000 claims description 3
150000003738 xylenes Chemical class 0.000 claims description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
229940075894 denatured ethanol Drugs 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
229940011051 isopropyl acetate Drugs 0.000 claims description 2
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 abstract description 4
-1 2 -deoxyribo-furanosyl Chemical class 0.000 description 17
238000010899 nucleation Methods 0.000 description 8
239000002002 slurry Substances 0.000 description 8
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
239000002777 nucleoside Substances 0.000 description 4
PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
125000003835 nucleoside group Chemical group 0.000 description 3
HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 2
HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000007405 data analysis Methods 0.000 description 2
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
125000006678 phenoxycarbonyl group Chemical group 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
LDHXMQXUOUZOLF-HERZVMAMSA-N (4r,5r)-3,3-difluoro-5-(hydroxymethyl)oxolane-2,4-diol Chemical compound OC[C@H]1OC(O)C(F)(F)[C@@H]1O LDHXMQXUOUZOLF-HERZVMAMSA-N 0.000 description 1
LSEFXLGTUCVBPE-UHFFFAOYSA-N 1h-imidazol-2-ylcarbamic acid Chemical compound OC(=O)NC1=NC=CN1 LSEFXLGTUCVBPE-UHFFFAOYSA-N 0.000 description 1
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical class CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
SRBFZHDQGSBBOR-MBMOQRBOSA-N alpha-D-arabinopyranose Chemical group O[C@@H]1CO[C@H](O)[C@@H](O)[C@@H]1O SRBFZHDQGSBBOR-MBMOQRBOSA-N 0.000 description 1
230000000118 anti-neoplastic effect Effects 0.000 description 1
229940034982 antineoplastic agent Drugs 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
238000000434 field desorption mass spectrometry Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229940117955 isoamyl acetate Drugs 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
238000000386 microscopy Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 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
238000001556 precipitation Methods 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002212 purine nucleoside Substances 0.000 description 1
239000002718 pyrimidine nucleoside Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011343 solid material Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof

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)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL106074A 1992-06-22 1993-06-21 Process for separating anomers of 2-deoxy-2,2-difluoro-D-pantopornosyl alkylsulfonate IL106074A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/902,303 US5256797A (en)	1992-06-22	1992-06-22	Process for separating 2-deoxy-2,2-difluoro-D-ribofuranosyl alkylsulfonate anomers

Publications (2)

Publication Number	Publication Date
IL106074A0 IL106074A0 (en)	1993-10-20
IL106074A true IL106074A (en)	1998-02-22

Family

ID=25415647

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL106074A IL106074A (en)	1992-06-22	1993-06-21	Process for separating anomers of 2-deoxy-2,2-difluoro-D-pantopornosyl alkylsulfonate

Country Status (17)

Country	Link
US (1)	US5256797A (fr)
EP (1)	EP0576232B1 (fr)
JP (1)	JPH0656867A (fr)
KR (1)	KR100302087B1 (fr)
AT (1)	ATE149505T1 (fr)
BR (1)	BR9302426A (fr)
CA (1)	CA2098888C (fr)
CY (1)	CY2091B1 (fr)
DE (1)	DE69308391T2 (fr)
DK (1)	DK0576232T3 (fr)
ES (1)	ES2100462T3 (fr)
GR (1)	GR3023060T3 (fr)
HK (1)	HK1006022A1 (fr)
HU (1)	HU217976B (fr)
IL (1)	IL106074A (fr)
MX (1)	MX9303714A (fr)
TW (1)	TW233300B (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MX9303713A (es) *	1992-06-22	1994-05-31	Lilly Co Eli	Proceso estereoselectivo para preparar un derivadoribofuranosilo enriquecido con alfa anomero.
PY0111577A (es)	2000-05-23	2017-01-02	Idenix Cayman Ltd	Métodos y composiciones para el tratamiento del virus de la hepatitis c
AP2006003708A0 (en)	2000-05-26	2006-08-31	Idenix Cayman Ltd	Methods and compositions for treating flavivirusesand pestiviruses
US7608600B2 (en) *	2002-06-28	2009-10-27	Idenix Pharmaceuticals, Inc.	Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections
CN1678326A (zh)	2002-06-28	2005-10-05	埃迪尼克斯(开曼)有限公司	用于治疗黄病毒感染的2'－c－甲基－3'－o－l－缬氨酸酯核糖呋喃基胞苷
RU2005118421A (ru)	2002-11-15	2006-01-20	Айденикс (Кайман) Лимитед (Ky)	2'-разветвленные нуклеозиды и мутация flaviviridae
PL377287A1 (pl)	2002-12-12	2006-01-23	Idenix (Cayman) Limited	Sposób wytwarzania 2'-rozgałęzionych nukleozydów
WO2006000922A2 (fr) *	2004-06-23	2006-01-05	Idenix (Cayman) Limited	Derives de 5-aza-7-deazapurine pour le traitement des flaviviridae
US7214791B2 (en) *	2004-07-01	2007-05-08	Shenzhen Hande Technology Co., Ltd.	Method for preparation of 2′-deoxy-2′, 2′-difluoro-β-cytidine or pharmaceutically acceptable salts thereof by using 1,6-anhydro-β-d-glucose as raw material
AT502221A1 (de) *	2005-07-20	2007-02-15	Pharmacon Forschung & Beratung Gmbh	Homogemcitabine, verfahren zu ihrer herstellung sowie deren verwendung
JP5254033B2 (ja)	2005-12-23	2013-08-07	イデニクプハルマセウティカルス，インコーポレイテッド	分岐型ヌクレオシドを調製するための合成中間体の製造方法
WO2007092705A2 (fr) *	2006-02-07	2007-08-16	Chemagis Ltd.	Procédé de préparation de gemcitabine et de produits intermédiaires associés
US20070249823A1 (en) *	2006-04-20	2007-10-25	Chemagis Ltd.	Process for preparing gemcitabine and associated intermediates
US20080262215A1 (en) *	2007-04-23	2008-10-23	Chemagis Ltd.	Gemcitabine production process
GB0812895D0 (en) *	2008-07-15	2008-08-20	Glycom As	Crystalline carbohydrate derivative

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4526988A (en) *	1983-03-10	1985-07-02	Eli Lilly And Company	Difluoro antivirals and intermediate therefor
DE3856477T2 (de) *	1987-08-28	2001-11-08	Eli Lilly And Co., Indianapolis	Verfahren zur Herstellung von 2'-deoxy-2',2'-difluornukleosiden
US4965374A (en) *	1987-08-28	1990-10-23	Eli Lilly And Company	Process for and intermediates of 2',2'-difluoronucleosides

1992
- 1992-06-22 US US07/902,303 patent/US5256797A/en not_active Expired - Lifetime
1993
- 1993-06-21 BR BR9302426A patent/BR9302426A/pt not_active Application Discontinuation
- 1993-06-21 EP EP93304821A patent/EP0576232B1/fr not_active Expired - Lifetime
- 1993-06-21 HU HU9301826A patent/HU217976B/hu not_active IP Right Cessation
- 1993-06-21 ES ES93304821T patent/ES2100462T3/es not_active Expired - Lifetime
- 1993-06-21 DK DK93304821.7T patent/DK0576232T3/da active
- 1993-06-21 JP JP5149152A patent/JPH0656867A/ja active Pending
- 1993-06-21 DE DE69308391T patent/DE69308391T2/de not_active Expired - Lifetime
- 1993-06-21 CA CA002098888A patent/CA2098888C/fr not_active Expired - Lifetime
- 1993-06-21 MX MX9303714A patent/MX9303714A/es unknown
- 1993-06-21 KR KR1019930011306A patent/KR100302087B1/ko not_active Expired - Fee Related
- 1993-06-21 AT AT93304821T patent/ATE149505T1/de active
- 1993-06-21 IL IL106074A patent/IL106074A/en not_active IP Right Cessation
- 1993-06-22 TW TW082104993A patent/TW233300B/zh not_active IP Right Cessation
1997
- 1997-04-08 GR GR970400728T patent/GR3023060T3/el unknown
1998
- 1998-06-12 HK HK98105211A patent/HK1006022A1/en not_active IP Right Cessation
- 1998-06-18 CY CY9800012A patent/CY2091B1/xx unknown

Also Published As

Publication number	Publication date
HU9301826D0 (en)	1993-09-28
HUT64551A (en)	1994-01-28
DE69308391T2 (de)	1997-07-17
CA2098888A1 (fr)	1993-12-23
CY2091B1 (en)	2002-04-05
KR940000473A (ko)	1994-01-03
HU217976B (hu)	2000-05-28
TW233300B (fr)	1994-11-01
BR9302426A (pt)	1994-01-11
EP0576232B1 (fr)	1997-03-05
EP0576232A1 (fr)	1993-12-29
MX9303714A (es)	1994-01-31
ES2100462T3 (es)	1997-06-16
US5256797A (en)	1993-10-26
GR3023060T3 (en)	1997-07-30
JPH0656867A (ja)	1994-03-01
KR100302087B1 (ko)	2001-10-22
DE69308391D1 (de)	1997-04-10
DK0576232T3 (da)	1997-07-21
IL106074A0 (en)	1993-10-20
HK1006022A1 (en)	1999-02-05
ATE149505T1 (de)	1997-03-15
CA2098888C (fr)	2003-07-29

Legal Events

Date	Code	Title
1998-08-16	FF	Patent granted
1998-12-06	KB	Patent renewed
1999-12-22	KB	Patent renewed
2003-07-31	KB	Patent renewed
2007-07-24	KB	Patent renewed
2011-06-30	KB	Patent renewed
2014-01-30	EXP	Patent expired

Publication	Publication Date	Title
CA2098888C (fr)	2003-07-29	Methode pour separer des anomeres d'alkylsulfonate de 2-desoxy-2,2-difluoro-d-ribofuranosyle
EP0646125B1 (fr)	1998-05-27	Analogues de nucleosides a base de 1,5-anhydrohexitol et leur utilisation pharmaceutique
US5401838A (en)	1995-03-28	Stereoselective fusion glycosylation process for preparing 2'-deoxy-2',2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides
EP0577302B1 (fr)	1997-07-16	Procédé de préparation de 2-deoxy-2,2-difluoro-D-ribofuranosyl sulphonates enrichis en anomère-alpha
HK1006022B (en)	1999-02-05	Process for separating 2-deoxy-2, 2-difluoro-d-ribofuranosyl alkylsulfonate anomers
US5218106A (en)	1993-06-08	2',3'-dideoxy-2'-fluoronucleosides
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