RU96119766A - DERIVATIVES 2,3-DIDEOXYPYRIMIDINE AND DIASTERI-SELECTIVE WAY OF OBTAINING THEM - Google Patents
DERIVATIVES 2,3-DIDEOXYPYRIMIDINE AND DIASTERI-SELECTIVE WAY OF OBTAINING THEMInfo
- Publication number
- RU96119766A RU96119766A RU96119766/04A RU96119766A RU96119766A RU 96119766 A RU96119766 A RU 96119766A RU 96119766/04 A RU96119766/04 A RU 96119766/04A RU 96119766 A RU96119766 A RU 96119766A RU 96119766 A RU96119766 A RU 96119766A
- Authority
- RU
- Russia
- Prior art keywords
- bromine
- iodine
- chlorine
- fluorine
- alkyl
- Prior art date
Links
- 229910052717 sulfur Inorganic materials 0.000 claims 18
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 239000000460 chlorine Chemical group 0.000 claims 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 239000011737 fluorine Substances 0.000 claims 6
- 229910052740 iodine Inorganic materials 0.000 claims 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 6
- 239000011630 iodine Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 3
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000000473 carbonimidoyl group Chemical group [H]\N=C(/*)* 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000002841 Lewis acid Substances 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 230000003899 glycosylation Effects 0.000 claims 1
- 238000006206 glycosylation reaction Methods 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
Claims (2)
где W - O, S, S=O, NZ или СН2;
X - O, S, S=O, SO2, NZ, СН2, CHF, CH, CHN3 или CHOH;
Y - О, S, СН2, CH, CHF или СНОН или СНОН;
Z - водород, гидроксил, алкил или ацил;
при условии, что когда Y - СН2 и X - О, S, S=О или SО2, то W не является О, S, S=O или SO2;
R2 - пуриновое или пиримидиновое основание или его аналог или его производное; и
R3 - замещенный карбонил или карбонильное производное.1. Derivatives of 2,3-dideoxypyrimidine of the formula VIII
where W is O, S, S = O, NZ or CH 2 ;
X is O, S, S = O, SO 2 , NZ, CH 2 , CHF, CH, CHN 3 or CHOH;
Y is O, S, CH 2 , CH, CHF or CHOH or CHOH;
Z is hydrogen, hydroxyl, alkyl or acyl;
provided that when Y is CH 2 and X is O, S, S = O or SO 2 , then W is not O, S, S = O or SO 2 ;
R 2 is a purine or pyrimidine base or an analog or derivative thereof; and
R 3 is a substituted carbonyl or carbonyl derivative.
R2 - пуриновое или пиримидиновое основание или его аналог или производное;
R3 - замещенный карбонил или карбонильное производное;
W - S, S=О или SО2, О, NZ или СН2;
X - О, S, S=О или SO2, NZ, СН2, CHF, CH, CHN3 или СНОН;
Y - О, S, СН2, CH, CHF или СНОН; и
Z - водород, гидроксил, алкил или ацил;
при условии, что W - не О, S, S=О или SO2, когда Y - СН2 и Х - О, S, S=О или SO2,
отличающийся тем, что включает в себя стадию гликозилирования требуемого пуринового или пиримидинового основания или его аналога или производного соединением формулы II
где L - уходящая группа,
с использованием кислоты Льюиса формулы III
где R5, R6 и R7 независимо выбраны из группы, состоящей из водорода; С1-20 алкила, необязательно замещенного фтором, бромом, хлором, иодом, С1-6 алкокси или С6-20 арилокси; С7-20 аралкила, необязательно замещенного галогеном, С1-20 алкилом или С1-20 алкокси; С6-20 арила, необязательно замещенного фтором, бромом, хлором, иодом, С1-20 алкилом или С1-20 алкокси; триалкилсилила; фтора; брома; хлора и иода; и
R3 выбран из группы, состоящей из фтора; брома; хлора, иода; сложных эфиров С1-20 сульфокислоты, необязательно замещенных фтором, бромом, хлором или иодом; сложных С1-20 алкиловых эфиров, необязательно замещенных фтором, бромом, хлором или иодом; поливалентных галогенидов; трехзамещенных силильных групп общей формулы (R5) (R6) (R7)Si (где R5, R6 и R7 - такие, как определены выше); насыщенного или ненасыщенного селененил - С6-20 арила; замещенного или незамещенного С6-20 арилсульфенила; замещенного или незамещенного С6-20 алкоксиалкила; и триалкилсилокси.2. Diastereoselective method of obtaining cis compounds of formula VIIIA
R 2 is a purine or pyrimidine base or an analog or derivative thereof;
R 3 is a substituted carbonyl or carbonyl derivative;
W is S, S = O or SO 2 , O, NZ or CH 2 ;
X is O, S, S = O or SO 2 , NZ, CH 2 , CHF, CH, CHN 3 or CHOH;
Y is O, S, CH 2 , CH, CHF or CHOH; and
Z is hydrogen, hydroxyl, alkyl or acyl;
provided that W is not O, S, S = O or SO 2 , when Y is CH 2 and X is O, S, S = O or SO 2 ,
characterized in that it comprises the step of glycosylation of the desired purine or pyrimidine base or its analogue or derivative with a compound of formula II
where L is a leaving group,
using Lewis acid of formula III
where R 5 , R 6 and R 7 are independently selected from the group consisting of hydrogen; C 1-20 alkyl, optionally substituted by fluorine, bromine, chlorine, iodine, C 1-6 alkoxy or C 6-20 aryloxy; C 7-20 aralkyl, optionally substituted with halogen, C 1-20 alkyl or C 1-20 alkoxy; C 6-20 aryl, optionally substituted with fluorine, bromine, chlorine, iodine, C 1-20 alkyl or C 1-20 alkoxy; trialkylsilyl; fluorine; bromine; chlorine and iodine; and
R 3 is selected from the group consisting of fluorine; bromine; chlorine, iodine; C 1-20 esters of sulfonic acids, optionally substituted by fluorine, bromine, chlorine or iodine; C 1-20 alkyl esters, optionally substituted with fluorine, bromine, chlorine or iodine; polyvalent halides; trisubstituted silyl groups of the general formula (R 5 ) (R 6 ) (R 7 ) Si (wherein R 5 , R 6 and R 7 are as defined above); saturated or unsaturated selenenyl — C 6-20 aryl; substituted or unsubstituted C 6-20 arylsulfenyl; substituted or unsubstituted C 6-20 alkoxyalkyl; and trialkylsiloxy.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US70337991A | 1991-05-21 | 1991-05-21 | |
US703379 | 1991-05-21 | ||
US703.379 | 1991-05-21 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU93058554A Division RU2105009C1 (en) | 1991-05-21 | 1992-05-20 | Method of diastereoselective synthesis of optically active cis-nucleosides, nucleoside analogs or derivatives and intermediate compounds for this method |
Publications (2)
Publication Number | Publication Date |
---|---|
RU96119766A true RU96119766A (en) | 1999-01-20 |
RU2163909C2 RU2163909C2 (en) | 2001-03-10 |
Family
ID=24825144
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU96119766/04A RU2163909C2 (en) | 1991-05-21 | 1992-05-20 | Pyrimidine 2,3-didesoxynucleoside derivatives and method of preparing thereof |
RU99115480/04A RU2223960C2 (en) | 1991-05-21 | 1992-05-20 | Diastereoselective method for preparing glycosylated purine or pyrimidine base |
RU93058554A RU2105009C1 (en) | 1991-05-21 | 1992-05-20 | Method of diastereoselective synthesis of optically active cis-nucleosides, nucleoside analogs or derivatives and intermediate compounds for this method |
RU93058362A RU2140925C1 (en) | 1991-05-21 | 1992-05-20 | Method of diastereoselective synthesis of nucleosides, intermediate compounds, and method of preparing intermediate compounds |
Family Applications After (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU99115480/04A RU2223960C2 (en) | 1991-05-21 | 1992-05-20 | Diastereoselective method for preparing glycosylated purine or pyrimidine base |
RU93058554A RU2105009C1 (en) | 1991-05-21 | 1992-05-20 | Method of diastereoselective synthesis of optically active cis-nucleosides, nucleoside analogs or derivatives and intermediate compounds for this method |
RU93058362A RU2140925C1 (en) | 1991-05-21 | 1992-05-20 | Method of diastereoselective synthesis of nucleosides, intermediate compounds, and method of preparing intermediate compounds |
Country Status (34)
Country | Link |
---|---|
US (5) | US5756706A (en) |
EP (2) | EP0515156B1 (en) |
JP (3) | JP3330972B2 (en) |
KR (3) | KR0160144B1 (en) |
CN (6) | CN1038591C (en) |
AT (2) | ATE157662T1 (en) |
AU (4) | AU655973B2 (en) |
BG (2) | BG61696B1 (en) |
CA (2) | CA2069063C (en) |
CZ (3) | CZ280857B6 (en) |
DE (2) | DE69208144T2 (en) |
DK (2) | DK0515156T3 (en) |
EE (1) | EE03044B1 (en) |
ES (2) | ES2104832T3 (en) |
FI (3) | FI109025B (en) |
GR (2) | GR3018941T3 (en) |
GT (1) | GT199800047A (en) |
HK (2) | HK132196A (en) |
HU (2) | HU221850B1 (en) |
IE (2) | IE76741B1 (en) |
IL (6) | IL116109A (en) |
MD (1) | MD1155C2 (en) |
MX (2) | MX9202404A (en) |
NO (2) | NO300593B1 (en) |
NZ (2) | NZ242818A (en) |
OA (1) | OA10212A (en) |
PL (3) | PL168910B1 (en) |
RO (1) | RO116812B1 (en) |
RU (4) | RU2163909C2 (en) |
SG (1) | SG43863A1 (en) |
SK (2) | SK279438B6 (en) |
TW (4) | TW467907B (en) |
WO (2) | WO1992020696A1 (en) |
ZA (2) | ZA923641B (en) |
Families Citing this family (109)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5466806A (en) * | 1989-02-08 | 1995-11-14 | Biochem Pharma Inc. | Processes for preparing substituted 1,3-oxathiolanes with antiviral properties |
US6175008B1 (en) | 1988-04-11 | 2001-01-16 | Biochem Pharma Inc. | Processes for preparing substituted 1,3-oxathiolanes with antiviral properties |
US6903224B2 (en) | 1988-04-11 | 2005-06-07 | Biochem Pharma Inc. | Substituted 1,3-oxathiolanes |
US6350753B1 (en) | 1988-04-11 | 2002-02-26 | Biochem Pharma Inc. | 2-Substituted-4-substituted-1,3-dioxolanes and use thereof |
PT674634E (en) * | 1989-02-08 | 2003-09-30 | Iaf Biochem Int | PROCESSES FOR PREPARING 1,3-OXATIOLANOS SUBSTITUTED WITH ANTIVIRARY PROPERTIES |
US5204466A (en) * | 1990-02-01 | 1993-04-20 | Emory University | Method and compositions for the synthesis of bch-189 and related compounds |
US6703396B1 (en) | 1990-02-01 | 2004-03-09 | Emory University | Method of resolution and antiviral activity of 1,3-oxathiolane nuclesoside enantiomers |
US5276151A (en) * | 1990-02-01 | 1994-01-04 | Emory University | Method of synthesis of 1,3-dioxolane nucleosides |
US5914331A (en) * | 1990-02-01 | 1999-06-22 | Emory University | Antiviral activity and resolution of 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane |
US6069252A (en) * | 1990-02-01 | 2000-05-30 | Emory University | Method of resolution and antiviral activity of 1,3-oxathiolane nucleoside enantiomers |
US5587480A (en) * | 1990-11-13 | 1996-12-24 | Biochem Pharma, Inc. | Substituted 1,3-oxathiolanes and substituted 1,3-dithiolanes with antiviral properties |
US5444063A (en) * | 1990-12-05 | 1995-08-22 | Emory University | Enantiomerically pure β-D-dioxolane nucleosides with selective anti-Hepatitis B virus activity |
US5925643A (en) * | 1990-12-05 | 1999-07-20 | Emory University | Enantiomerically pure β-D-dioxolane-nucleosides |
US6812233B1 (en) | 1991-03-06 | 2004-11-02 | Emory University | Therapeutic nucleosides |
US5817667A (en) * | 1991-04-17 | 1998-10-06 | University Of Georgia Research Foudation | Compounds and methods for the treatment of cancer |
ZA923641B (en) * | 1991-05-21 | 1993-02-24 | Iaf Biochem Int | Processes for the diastereoselective synthesis of nucleosides |
US6444656B1 (en) | 1992-12-23 | 2002-09-03 | Biochem Pharma, Inc. | Antiviral phosphonate nucleotides |
GB9226879D0 (en) * | 1992-12-23 | 1993-02-17 | Iaf Biochem Int | Anti-viral compounds |
US6005107A (en) * | 1992-12-23 | 1999-12-21 | Biochem Pharma, Inc. | Antiviral compounds |
GB9226927D0 (en) * | 1992-12-24 | 1993-02-17 | Iaf Biochem Int | Dideoxy nucleoside analogues |
TW374087B (en) * | 1993-05-25 | 1999-11-11 | Univ Yale | L-2',3'-dideoxy nucleotide analogs as anti-hepatitis B(HBV) and anti-HIV agents |
US5627160A (en) * | 1993-05-25 | 1997-05-06 | Yale University | L-2',3'-dideoxy nucleoside analogs as anti-hepatitis B (HBV) and anti-HIV agents |
GB9311709D0 (en) * | 1993-06-07 | 1993-07-21 | Iaf Biochem Int | Stereoselective synthesis of nucleoside analogues using bicycle intermediate |
WO1995007086A1 (en) * | 1993-09-10 | 1995-03-16 | Emory University | Nucleosides with anti-hepatitis b virus activity |
US20020120130A1 (en) | 1993-09-10 | 2002-08-29 | Gilles Gosselin | 2' or 3' -deoxy and 2', 3' -dideoxy-beta-L-pentofuranonucleo-side compounds, method of preparation and application in therapy, especially as anti- viral agents |
US5587362A (en) * | 1994-01-28 | 1996-12-24 | Univ. Of Ga Research Foundation | L-nucleosides |
IL113432A (en) * | 1994-04-23 | 2000-11-21 | Glaxo Group Ltd | Process for the diastereoselective synthesis of nucleoside analogues |
GB9413724D0 (en) * | 1994-07-07 | 1994-08-24 | Wellcome Found | Therapeutic nucleosides |
US6514949B1 (en) | 1994-07-11 | 2003-02-04 | University Of Virginia Patent Foundation | Method compositions for treating the inflammatory response |
US6448235B1 (en) | 1994-07-11 | 2002-09-10 | University Of Virginia Patent Foundation | Method for treating restenosis with A2A adenosine receptor agonists |
IL115156A (en) | 1994-09-06 | 2000-07-16 | Univ Georgia | Pharmaceutical compositions for the treatment of cancer comprising 1-(2-hydroxymethyl-1,3-dioxolan-4-yl) cytosines |
US6391859B1 (en) | 1995-01-27 | 2002-05-21 | Emory University | [5-Carboxamido or 5-fluoro]-[2′,3′-unsaturated or 3′-modified]-pyrimidine nucleosides |
US5703058A (en) * | 1995-01-27 | 1997-12-30 | Emory University | Compositions containing 5-fluoro-2',3'-didehydro-2',3'-dideoxycytidine or a mono-, di-, or triphosphate thereof and a second antiviral agent |
US5808040A (en) * | 1995-01-30 | 1998-09-15 | Yale University | L-nucleosides incorporated into polymeric structure for stabilization of oligonucleotides |
US5869461A (en) * | 1995-03-16 | 1999-02-09 | Yale University | Reducing toxicity of L-nucleosides with D-nucleosides |
GB9506644D0 (en) * | 1995-03-31 | 1995-05-24 | Wellcome Found | Preparation of nucleoside analogues |
AU722214B2 (en) | 1995-06-07 | 2000-07-27 | Centre National De La Recherche Scientifique (Cnrs) | Nucleosides with anti-hepatitis B virus activity |
AU7341896A (en) * | 1995-11-02 | 1997-05-22 | Chong Kun Dang Corporation | Novel nucleoside derivatives and process for preparing the same |
GB9600143D0 (en) | 1996-01-05 | 1996-03-06 | Wellcome Found | Therapeutic compounds |
EP0799834A1 (en) * | 1996-04-04 | 1997-10-08 | Novartis AG | Modified nucleotides |
US6005097A (en) * | 1996-06-14 | 1999-12-21 | Vion Pharmaceuticals, Inc. | Processes for high-yield diastereoselective synthesis of dideoxynucleosides |
US5753789A (en) * | 1996-07-26 | 1998-05-19 | Yale University | Oligonucleotides containing L-nucleosides |
US6022876A (en) | 1996-11-15 | 2000-02-08 | Yale University | L-β-dioxolane uridine analogs and methods for treating and preventing Epstein-Barr virus infections |
JP2001512453A (en) | 1997-02-13 | 2001-08-21 | グラックス グループ リミテッド | Benzimidazole derivatives |
JP2001518899A (en) | 1997-04-07 | 2001-10-16 | トライアングル ファーマシューティカルズ,インコーポレイティド | Use of MKC-442 in combination with other antiviral agents |
BR9810745A (en) | 1997-06-10 | 2001-03-13 | Glaxo Group Ltd | Benzimidazole derivatives |
PL338454A1 (en) | 1997-07-30 | 2000-11-06 | Univ Michigan | Lixofuranosilbenzimidazoles as antiviral agents |
US20030220234A1 (en) * | 1998-11-02 | 2003-11-27 | Selvaraj Naicker | Deuterated cyclosporine analogs and their use as immunodulating agents |
YU44900A (en) | 1998-01-31 | 2003-01-31 | Glaxo Group Limited | 2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives |
RU2439069C2 (en) | 1998-08-12 | 2012-01-10 | Гайлид Сайенсиз, Инк. | Method of producing 1,3-oxathiolane nucleosides |
US6979561B1 (en) | 1998-10-09 | 2005-12-27 | Gilead Sciences, Inc. | Non-homogeneous systems for the resolution of enantiomeric mixtures |
JP2002533470A (en) | 1998-12-23 | 2002-10-08 | シャイアー・バイオケム・インコーポレイテッド | Antiviral nucleoside analogues |
US7635690B2 (en) | 1999-01-22 | 2009-12-22 | Emory University | HIV-1 mutations selected for by β-2′,3′-didehydro-2′,3′-dideoxy-5-fluorocytidine |
US7115584B2 (en) | 1999-01-22 | 2006-10-03 | Emory University | HIV-1 mutations selected for by β-2′,3′-didehydro-2′,3′-dideoxy-5-fluorocytidine |
US6232297B1 (en) | 1999-02-01 | 2001-05-15 | University Of Virginia Patent Foundation | Methods and compositions for treating inflammatory response |
US7378400B2 (en) * | 1999-02-01 | 2008-05-27 | University Of Virginia Patent Foundation | Method to reduce an inflammatory response from arthritis |
US7427606B2 (en) * | 1999-02-01 | 2008-09-23 | University Of Virginia Patent Foundation | Method to reduce inflammatory response in transplanted tissue |
YU25500A (en) | 1999-05-11 | 2003-08-29 | Pfizer Products Inc. | Process for the synthesis of nucleosite analogues |
US6322771B1 (en) | 1999-06-18 | 2001-11-27 | University Of Virginia Patent Foundation | Induction of pharmacological stress with adenosine receptor agonists |
EP1214074B1 (en) * | 1999-09-24 | 2004-06-16 | Shire Biochem Inc. | Dioxolane nucleoside analogs for the treatment or prevention of viral infection |
CA2389745C (en) | 1999-11-04 | 2010-03-23 | Shire Biochem Inc. | Method for the treatment or prevention of flaviviridae viral infection using nucleoside analogues |
US6436948B1 (en) | 2000-03-03 | 2002-08-20 | University Of Georgia Research Foundation Inc. | Method for the treatment of psoriasis and genital warts |
CA2308559C (en) * | 2000-05-16 | 2005-07-26 | Brantford Chemicals Inc. | 1,3-oxathiolan-5-ones useful in the production of antiviral nucleoside analogues |
CA2690137C (en) | 2001-03-01 | 2012-11-13 | Gilead Sciences, Inc. | Polymorphic and other crystalline forms of cis-ftc |
US6600044B2 (en) | 2001-06-18 | 2003-07-29 | Brantford Chemicals Inc. | Process for recovery of the desired cis-1,3-oxathiolane nucleosides from their undesired trans-isomers |
CA2460911C (en) * | 2001-10-01 | 2011-08-30 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs having a2a agonist activity and compositions thereof |
ES2326040T3 (en) * | 2001-10-19 | 2009-09-29 | Isotechnika Inc. | SYNTHESIS OF CYCLOSPORINE ANALOGS. |
ITMI20012317A1 (en) * | 2001-11-06 | 2003-05-06 | Recordati Ind Chimica E Farma | DIASTEREOSELECTIVE PROCESS FOR THE PREPARATION OF THE ANTIVIRAL AGENT4-AMINO-1- (2R-IDROSSIMETIL- / 1,3 / OSSATIOLAN-5S-I1) -1H-PIRIMIDIN-2-ONE |
WO2003051298A2 (en) * | 2001-12-14 | 2003-06-26 | Pharmasset Ltd. | Preparation of intermediates useful in the synthesis of antiviral nucleosides |
EP1467990B1 (en) | 2002-01-25 | 2012-03-07 | Shire BioChem Inc. | Process for producing dioxolane nucleoside analogue precursors |
US7365173B2 (en) * | 2002-02-04 | 2008-04-29 | American National Red Cross | Method for the production of pure virally inactivated butyrylcholinesterase |
MXPA05001451A (en) | 2002-08-06 | 2005-09-30 | Pharmasset Ltd | Processes for preparing 1,3-dioxolane nucleosides. |
ATE398455T1 (en) | 2003-01-14 | 2008-07-15 | Gilead Sciences Inc | COMPOSITIONS AND METHODS FOR ANTIVIRAL COMBINATION THERAPY |
ITMI20030578A1 (en) * | 2003-03-24 | 2004-09-25 | Clariant Lsm Italia Spa | PROCESS AND INTERMEDIATES FOR THE PREPARATION OF EMTRICITABINE |
US7785839B2 (en) | 2004-02-03 | 2010-08-31 | Emory University | Methods to manufacture 1,3-dioxolane nucleosides |
US7442687B2 (en) * | 2004-08-02 | 2008-10-28 | The University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs having A2A agonist activity |
US7605143B2 (en) * | 2004-08-02 | 2009-10-20 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs with modified 5′-ribose groups having A2A agonist activity |
WO2006028618A1 (en) * | 2004-08-02 | 2006-03-16 | University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs with modified 5'-ribose groups having a2a agonist activity |
US7837651B2 (en) * | 2004-08-31 | 2010-11-23 | Ethicon Endo-Surgery, Inc. | Infusion pump |
US7250416B2 (en) | 2005-03-11 | 2007-07-31 | Supergen, Inc. | Azacytosine analogs and derivatives |
TWI471145B (en) | 2005-06-13 | 2015-02-01 | Bristol Myers Squibb & Gilead Sciences Llc | Unitary pharmaceutical dosage form |
TWI375560B (en) | 2005-06-13 | 2012-11-01 | Gilead Sciences Inc | Composition comprising dry granulated emtricitabine and tenofovir df and method for making the same |
US7700567B2 (en) | 2005-09-29 | 2010-04-20 | Supergen, Inc. | Oligonucleotide analogues incorporating 5-aza-cytosine therein |
WO2007077505A2 (en) * | 2005-12-30 | 2007-07-12 | Ranbaxy Laboratories Limited | Crystalline l-menthyl (2r, 5s)-5-(4-amino-5-fluoro-2-oxo-2h-pyrimidin-1-yl)[1, 3]oxathiolan-2-carboxylate and process for preparation thereof |
WO2007120972A2 (en) * | 2006-02-10 | 2007-10-25 | University Of Virginia Patent Foundation | Method to treat sickle cell disease |
US8188063B2 (en) * | 2006-06-19 | 2012-05-29 | University Of Virginia Patent Foundation | Use of adenosine A2A modulators to treat spinal cord injury |
EP2086955A2 (en) * | 2006-10-30 | 2009-08-12 | Lupin Ltd. | An improved process for the manufacture of cis(-)-lamivudine |
EP2205073A4 (en) | 2007-09-26 | 2013-03-06 | Sinai School Medicine | Azacytidine analogues and uses thereof |
WO2009069011A1 (en) * | 2007-11-29 | 2009-06-04 | Ranbaxy Laboratories Limited | Process for the preparation of substituted 1,3-oxathiolanes |
AU2008331167A1 (en) * | 2007-11-29 | 2009-06-04 | Ranbaxy Laboratories Limited | Process and intermediates for the preparation of substituted 1, 3-oxathiolanes, especially lamivudine |
WO2009084033A2 (en) * | 2007-12-07 | 2009-07-09 | Matrix Laboratories Limited | Process for producing 5-fluoro-1-(2r,5s)-[2-(hydroxymethyl)-1,3-oxathiolan-5-yi]cytosine |
US8058259B2 (en) * | 2007-12-20 | 2011-11-15 | University Of Virginia Patent Foundation | Substituted 4-{3-[6-amino-9-(3,4-dihydroxy-tetrahydro-furan-2-yl)-9H-purin-2-yl]-prop-2-ynyl}-piperidine-1-carboxylic acid esters as A2AR agonists |
SG190618A1 (en) | 2008-05-02 | 2013-06-28 | Gilead Sciences Inc | The use of solid carrier particles to improve the processability of a pharmaceutical agent |
WO2010082128A1 (en) | 2009-01-19 | 2010-07-22 | Aurobindo Pharma Limited | Process for the preparation of cis-nucleoside derivative |
SG10201706215UA (en) | 2009-02-06 | 2017-08-30 | Gilead Sciences Inc | Tablets for combination therapy |
WO2011083484A2 (en) * | 2010-01-08 | 2011-07-14 | Hetero Research Foundation | Improved process for nucleosides |
KR20170078868A (en) | 2010-01-27 | 2017-07-07 | 비이브 헬쓰케어 컴퍼니 | Antibiral therapy |
US20120295930A1 (en) * | 2010-02-03 | 2012-11-22 | Shankar Rama | Novel process for the preparation of cis-nucleoside derivative |
EP2542551B1 (en) | 2010-03-04 | 2014-08-27 | Ranbaxy Laboratories Limited | A process for stereoselective synthesis of 5-fluoro-1-(2r,5s)-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine |
EP2377862A1 (en) | 2010-03-29 | 2011-10-19 | Esteve Química, S.A. | Process for obtaining emtricitabine |
WO2011141805A2 (en) | 2010-05-14 | 2011-11-17 | Lupin Limited | An improved process for the manufacture of lamivudine |
WO2012062835A1 (en) | 2010-11-12 | 2012-05-18 | Glaxo Wellcome Manufacturing Pte Ltd | Novel pharmaceutical compositions |
WO2013021290A1 (en) | 2011-08-05 | 2013-02-14 | Lupin Limited | A stereoselective process for preparation of 1,3-oxathiolane nucleosides |
LT2750768T (en) | 2011-08-30 | 2019-02-11 | Astex Pharmaceuticals, Inc. | Decitabine derivative formulations |
CN103242243B (en) * | 2013-01-08 | 2015-08-19 | 北京大学 | A kind of base triacetin ether-ether molecule, its chemical synthesis process and the application in field of gene thereof |
CN103288806A (en) * | 2013-07-02 | 2013-09-11 | 山东大学 | Synthesis method of troxacitabine |
AU2016287585B2 (en) | 2015-07-02 | 2020-12-17 | Otsuka Pharmaceutical Co., Ltd. | Lyophilized pharmaceutical compositions |
CN105037340B (en) * | 2015-07-14 | 2018-08-10 | 福建广生堂药业股份有限公司 | A kind of preparation method of lamivudine key intermediate chiral isomer impurity |
MX2020001233A (en) | 2017-08-03 | 2020-07-20 | Otsuka Pharma Co Ltd | Drug compound and purification methods thereof. |
Family Cites Families (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1445013A (en) * | 1964-07-09 | 1966-07-08 | Thomae Gmbh Dr K | Process for making new dioxolano-2-carboxylic acids |
US4383114A (en) * | 1977-02-09 | 1983-05-10 | Regents Of The University Of Minnesota | Adenosine deaminase resistant antiviral purine arabinonucleosides |
US4231945A (en) * | 1978-11-08 | 1980-11-04 | Schering Corporation | S-5-(Azidomethyl or aminomethyl)-2-lower-alkoxytetrahydrofurans |
US4479942A (en) * | 1981-08-10 | 1984-10-30 | Fujisawa Pharmaceutical Co., Ltd. | Tetrahydrofurnancarboxylic acid derivatives, processes for preparation thereof and pharmaceutical compositions thereof |
US4855304A (en) * | 1985-01-10 | 1989-08-08 | Repligen Corporation | Dinucleoside pyrophosphates and pyrophosphate homologs as plant antivirals |
DK363987A (en) * | 1986-08-08 | 1988-02-09 | Hoffmann La Roche | pyrimidine |
GB8621268D0 (en) * | 1986-09-03 | 1986-10-08 | Univ Strathclyde | Separation of substances |
US4997818A (en) * | 1987-09-21 | 1991-03-05 | The University Hospital | Therapeutic method for selectively treating terminal deoxynucleotidyl transferase-positive neoplastic leukemias and lymphomas |
SE8704298D0 (en) * | 1987-11-03 | 1987-11-03 | Astra Ab | COMPOUNDS FOR USE IN THERAPY |
US4997926A (en) * | 1987-11-18 | 1991-03-05 | Scripps Clinic And Research Foundation | Deaminase-stable anti-retroviral 2-halo-2',3'-dideoxy |
JPH022349A (en) * | 1988-02-17 | 1990-01-08 | Takeda Chem Ind Ltd | Pyrimidine analogue-tolerated gene dna and use thereof |
US5047407A (en) * | 1989-02-08 | 1991-09-10 | Iaf Biochem International, Inc. | 2-substituted-5-substituted-1,3-oxathiolanes with antiviral properties |
NZ228645A (en) * | 1988-04-11 | 1991-09-25 | Iaf Biochem Int | 1,3-dioxolane derivatives substituted in the 5th position by a purine or pyrimidine radical; treatment of viral infections |
GB8815265D0 (en) * | 1988-06-27 | 1988-08-03 | Wellcome Found | Therapeutic nucleosides |
DE3823127A1 (en) * | 1988-07-08 | 1990-01-11 | Rheinische Braunkohlenw Ag | DEVICE AND METHOD FOR PURIFYING WASTE WATER |
US4987224A (en) * | 1988-08-02 | 1991-01-22 | University Of Georgia Research Foundation, Inc. | Method of preparation of 2',3'-dideoxynucleosides |
DE3827134A1 (en) * | 1988-08-10 | 1990-03-15 | Bayer Ag | SUBSTITUTED TRIAZOLYL OR IMIDAZOLYL-HYDROXYALKYLDIOXOLANE, METHOD FOR THE PRODUCTION THEREOF AND THE USE THEREOF AS MICROBICIDES, OXIRANYLDIOXOLANES, DIOXOLANYLKETONE, OXIRANYLKETONE AND (ALPHA) -HALOGENICENETHENO ZERO DETECTED |
US5075225A (en) * | 1989-04-06 | 1991-12-24 | The Texas A&M University System | Process for the enzymatic synthesis of nucleosides |
NZ233197A (en) * | 1989-04-13 | 1991-11-26 | Richard Thomas Walker | Aromatically substituted nucleotide derivatives, intermediates therefor and pharmaceutical compositions |
IE902574A1 (en) * | 1989-07-17 | 1991-02-27 | Univ Birmingham | Antiviral pyrimidine nucleosides |
IE904378A1 (en) * | 1989-12-20 | 1991-07-03 | Abbott Lab | Analogs of oxetanyl purines and pyrimidines |
US5204466A (en) * | 1990-02-01 | 1993-04-20 | Emory University | Method and compositions for the synthesis of bch-189 and related compounds |
GB9009861D0 (en) * | 1990-05-02 | 1990-06-27 | Glaxo Group Ltd | Chemical compounds |
GB9014090D0 (en) * | 1990-06-25 | 1990-08-15 | Zaadunie Bv | Improvements in or relating to organic compounds |
WO1992010496A1 (en) * | 1990-12-05 | 1992-06-25 | University Of Georgia Research Foundation, Inc. | ENANTIOMERICALLY PURE β-L-(-)-1,3-OXATHIOLANE NUCLEOSIDES |
NZ241625A (en) * | 1991-02-22 | 1996-03-26 | Univ Emory | 1,3-oxathiolane derivatives, anti-viral compositions containing such and method of resolving racemic mixture of enantiomers |
WO1992018517A1 (en) * | 1991-04-17 | 1992-10-29 | Yale University | Method of treating or preventing hepatitis b virus |
GB9109506D0 (en) * | 1991-05-02 | 1991-06-26 | Wellcome Found | Therapeutic nucleosides |
ZA923641B (en) * | 1991-05-21 | 1993-02-24 | Iaf Biochem Int | Processes for the diastereoselective synthesis of nucleosides |
-
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