HUP0301875A2 - Pirrolo[2,3-d]pirimidinnukleozid-származékok - Google Patents
Pirrolo[2,3-d]pirimidinnukleozid-származékok Download PDFInfo
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- HUP0301875A2 HUP0301875A2 HU0301875A HUP0301875A HUP0301875A2 HU P0301875 A2 HUP0301875 A2 HU P0301875A2 HU 0301875 A HU0301875 A HU 0301875A HU P0301875 A HUP0301875 A HU P0301875A HU P0301875 A2 HUP0301875 A2 HU P0301875A2
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- cell
- amino
- compound
- pyrrolo
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- 239000002718 pyrimidine nucleoside Substances 0.000 title abstract description 22
- JJTNLWSCFYERCK-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidine Chemical compound N1=CN=C2NC=CC2=C1 JJTNLWSCFYERCK-UHFFFAOYSA-N 0.000 title description 52
- 150000001875 compounds Chemical class 0.000 claims abstract description 183
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 36
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 26
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 26
- 150000003833 nucleoside derivatives Chemical class 0.000 claims abstract description 26
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 25
- -1 pyrrolo[2,3-d)pyrimidine nucleoside derivatives Chemical class 0.000 claims abstract description 25
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 19
- 125000000524 functional group Chemical group 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 125000003277 amino group Chemical group 0.000 claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 125000006239 protecting group Chemical group 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
- 210000004027 cell Anatomy 0.000 claims description 79
- 102000004127 Cytokines Human genes 0.000 claims description 38
- 108090000695 Cytokines Proteins 0.000 claims description 38
- 238000002360 preparation method Methods 0.000 claims description 31
- 206010028980 Neoplasm Diseases 0.000 claims description 19
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- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 17
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- 108090000978 Interleukin-4 Proteins 0.000 claims description 8
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- 230000005764 inhibitory process Effects 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
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- 230000010261 cell growth Effects 0.000 claims description 4
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- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 5
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- 230000002519 immonomodulatory effect Effects 0.000 abstract description 4
- 231100000433 cytotoxic Toxicity 0.000 abstract description 3
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- 230000001093 anti-cancer Effects 0.000 abstract description 2
- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 abstract description 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
- 239000000203 mixture Substances 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 23
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 238000004587 chromatography analysis Methods 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
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- 102000004890 Interleukin-8 Human genes 0.000 description 8
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- XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 description 8
- 229940096397 interleukin-8 Drugs 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- NVJFFHZJCFOMTJ-UHFFFAOYSA-N 4-amino-6-bromo-7h-pyrrolo[2,3-d]pyrimidine-5-carbonitrile Chemical compound NC1=NC=NC2=C1C(C#N)=C(Br)N2 NVJFFHZJCFOMTJ-UHFFFAOYSA-N 0.000 description 7
- 108020004414 DNA Proteins 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
- 238000000338 in vitro Methods 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000002777 nucleoside Substances 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 239000006188 syrup Substances 0.000 description 6
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
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- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 4
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- 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
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
-
- 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
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/14—Pyrrolo-pyrimidine radicals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Virology (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15123399P | 1999-08-27 | 1999-08-27 | |
| PCT/US2000/022674 WO2001027114A1 (en) | 1999-08-27 | 2000-08-17 | PYRROLO[2,3-d]PYRIMIDINE NUCLEOSIDE ANALOGS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUP0301875A2 true HUP0301875A2 (hu) | 2003-09-29 |
Family
ID=22537871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0301875A HUP0301875A2 (hu) | 1999-08-27 | 2000-08-17 | Pirrolo[2,3-d]pirimidinnukleozid-származékok |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP1212326A4 (pl) |
| JP (1) | JP2003511454A (pl) |
| KR (1) | KR20020092904A (pl) |
| CN (1) | CN1384834A (pl) |
| AU (1) | AU769578B2 (pl) |
| BR (1) | BR0013642A (pl) |
| CA (1) | CA2381297A1 (pl) |
| HR (1) | HRP20020163A2 (pl) |
| HU (1) | HUP0301875A2 (pl) |
| IL (1) | IL147908A0 (pl) |
| MX (1) | MXPA02001753A (pl) |
| NO (1) | NO20020931L (pl) |
| PL (1) | PL354094A1 (pl) |
| RU (1) | RU2002103501A (pl) |
| SI (1) | SI20819A (pl) |
| SK (1) | SK1772002A3 (pl) |
| WO (1) | WO2001027114A1 (pl) |
| ZA (1) | ZA200201567B (pl) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6455508B1 (en) * | 2000-02-15 | 2002-09-24 | Kanda S. Ramasamy | Methods for treating diseases with tirazole and pyrrolo-pyrimidine ribofuranosyl nucleosides |
| US7638496B2 (en) | 2000-02-15 | 2009-12-29 | Valeant Pharmaceuticals North America | Nucleoside analogs with carboxamidine modified monocyclic base |
| JP2003183283A (ja) * | 2001-12-18 | 2003-07-03 | Takeda Chem Ind Ltd | 縮合インドール化合物、その製造法および用途 |
| US20050182252A1 (en) | 2004-02-13 | 2005-08-18 | Reddy K. R. | Novel 2'-C-methyl nucleoside derivatives |
| CN101851241B (zh) * | 2010-07-02 | 2012-05-23 | 西安交通大学 | 一种抗肿瘤化合物及其制备方法和其用途 |
| WO2012040127A1 (en) | 2010-09-22 | 2012-03-29 | Alios Biopharma, Inc. | Substituted nucleotide analogs |
| CN102286048A (zh) * | 2011-06-24 | 2011-12-21 | 吉林大学 | 4-氨基-6-(3-(3-溴苯基)苯基)-5-氰基-7-(β-L-呋喃木糖)吡咯并[2, 3-d]嘧啶、同类衍生物及用于制备抗肿瘤药物 |
| EP2794630A4 (en) | 2011-12-22 | 2015-04-01 | Alios Biopharma Inc | SUBSTITUTED PHOSPHORTHIOAT NUCLEOTIDE ANALOGUE |
| KR102072041B1 (ko) | 2011-12-22 | 2020-01-31 | 앨리오스 바이오파마 인크. | 치환된 뉴클레오사이드, 뉴클레오타이드 및 그의 유사체 |
| NZ631601A (en) | 2012-03-21 | 2016-06-24 | Alios Biopharma Inc | Solid forms of a thiophosphoramidate nucleotide prodrug |
| USRE48171E1 (en) | 2012-03-21 | 2020-08-25 | Janssen Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| US9441007B2 (en) | 2012-03-21 | 2016-09-13 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| NZ630805A (en) | 2012-03-22 | 2016-01-29 | Alios Biopharma Inc | Pharmaceutical combinations comprising a thionucleotide analog |
| EP3623364A1 (en) | 2014-02-13 | 2020-03-18 | Ligand Pharmaceuticals, Inc. | Prodrug compounds and their uses |
| CN106687118A (zh) | 2014-07-02 | 2017-05-17 | 配体药物公司 | 前药化合物及其用途 |
| AR104326A1 (es) | 2015-05-04 | 2017-07-12 | Lilly Co Eli | Compuestos nucleósidos 5-sustituidos |
| JP6768796B2 (ja) * | 2015-09-23 | 2020-10-14 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | ４’−置換ヌクレオシド逆転写酵素阻害剤及びその調製 |
| WO2019139919A1 (en) | 2018-01-09 | 2019-07-18 | Ligand Pharmaceuticals, Inc. | Acetal compounds and therapeutic uses thereof |
| IL316537A (en) | 2018-05-15 | 2024-12-01 | Illumina Inc | Compositions and methods for chemical removal and deprotection of surface-bound oligonucleotides |
| JP2022522534A (ja) | 2019-04-02 | 2022-04-19 | アリゴス セラピューティクス インコーポレイテッド | Ｐｒｍｔ５を標的にする化合物 |
| KR102639275B1 (ko) * | 2021-06-08 | 2024-02-21 | 퓨쳐메디신 주식회사 | 다중 표적 인산화효소 저해 활성을 갖는 뉴클레오사이드 유도체 및 이를 포함하는 암의 예방 및 치료용 약학적 조성물 |
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| US3988338A (en) * | 1974-04-24 | 1976-10-26 | Wisconsin Alumni Research Foundation | 4-Substituted amino-2-substituted thio-pyrrolo-[2,3-d]pyrimidine derivatives |
| US4892865A (en) * | 1987-12-01 | 1990-01-09 | The Regents Of The University Of Michigan | Pyrrolo[2,3-d]pyrimidine nucleosides as antiviral agents |
| US5674998A (en) * | 1989-09-15 | 1997-10-07 | Gensia Inc. | C-4' modified adenosine kinase inhibitors |
| WO1994018215A1 (en) * | 1993-02-03 | 1994-08-18 | Gensia, Inc. | Adenosine kinase inhibitors comprising lyxofuranosyl derivatives |
| US5665721A (en) * | 1995-06-07 | 1997-09-09 | Abbott Laboratories | Heterocyclic substituted cyclopentane compounds |
| AU727177B2 (en) * | 1996-10-16 | 2000-12-07 | Icn Pharmaceuticals, Inc. | Purine L-nucleosides, analogs and uses thereof |
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- 2000-08-17 JP JP2001530332A patent/JP2003511454A/ja not_active Withdrawn
- 2000-08-17 SI SI200020035A patent/SI20819A/sl not_active IP Right Cessation
- 2000-08-17 KR KR1020027002570A patent/KR20020092904A/ko not_active Withdrawn
- 2000-08-17 BR BR0013642-5A patent/BR0013642A/pt not_active IP Right Cessation
- 2000-08-17 MX MXPA02001753A patent/MXPA02001753A/es unknown
- 2000-08-17 HU HU0301875A patent/HUP0301875A2/hu unknown
- 2000-08-17 EP EP00959267A patent/EP1212326A4/en not_active Withdrawn
- 2000-08-17 CA CA002381297A patent/CA2381297A1/en not_active Abandoned
- 2000-08-17 RU RU2002103501/04A patent/RU2002103501A/ru not_active Application Discontinuation
- 2000-08-17 CN CN00814992A patent/CN1384834A/zh active Pending
- 2000-08-17 AU AU70618/00A patent/AU769578B2/en not_active Ceased
- 2000-08-17 IL IL14790800A patent/IL147908A0/xx unknown
- 2000-08-17 HR HR20020163A patent/HRP20020163A2/hr not_active Application Discontinuation
- 2000-08-17 SK SK177-2002A patent/SK1772002A3/sk unknown
- 2000-08-17 WO PCT/US2000/022674 patent/WO2001027114A1/en not_active Ceased
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2002
- 2002-02-25 ZA ZA200201567A patent/ZA200201567B/en unknown
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| MXPA02001753A (es) | 2002-10-23 |
| BR0013642A (pt) | 2002-05-07 |
| IL147908A0 (en) | 2002-08-14 |
| JP2003511454A (ja) | 2003-03-25 |
| ZA200201567B (en) | 2003-07-30 |
| AU769578B2 (en) | 2004-01-29 |
| PL354094A1 (pl) | 2003-12-29 |
| CN1384834A (zh) | 2002-12-11 |
| AU7061800A (en) | 2001-04-23 |
| NO20020931D0 (no) | 2002-02-26 |
| EP1212326A1 (en) | 2002-06-12 |
| KR20020092904A (ko) | 2002-12-12 |
| SK1772002A3 (en) | 2002-10-08 |
| HRP20020163A2 (en) | 2004-02-29 |
| RU2002103501A (ru) | 2003-09-10 |
| EP1212326A4 (en) | 2003-08-20 |
| SI20819A (sl) | 2002-08-31 |
| CA2381297A1 (en) | 2001-04-19 |
| WO2001027114A1 (en) | 2001-04-19 |
| NO20020931L (no) | 2002-02-26 |
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