DE60101223T2 - Antivirale pyrimidin nucleoside derivate - Google Patents
Antivirale pyrimidin nucleoside derivate Download PDFInfo
- Publication number
- DE60101223T2 DE60101223T2 DE60101223T DE60101223T DE60101223T2 DE 60101223 T2 DE60101223 T2 DE 60101223T2 DE 60101223 T DE60101223 T DE 60101223T DE 60101223 T DE60101223 T DE 60101223T DE 60101223 T2 DE60101223 T2 DE 60101223T2
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- Prior art keywords
- alkyl
- group
- compound according
- halogens
- dideoxy
- Prior art date
- Legal status (The legal status 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 status listed.)
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- 230000000840 anti-viral effect Effects 0.000 title abstract description 10
- 150000003833 nucleoside derivatives Chemical class 0.000 title description 2
- 239000002718 pyrimidine nucleoside Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 18
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
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- 230000009385 viral infection Effects 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 208000036142 Viral infection Diseases 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000002777 nucleoside Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 7
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- 150000001345 alkine derivatives Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
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- 230000002879 macerating effect Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- GYCKQBWUSACYIF-UHFFFAOYSA-N o-hydroxybenzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
- UMIPWJGWASORKV-UHFFFAOYSA-N oct-1-yne Chemical compound CCCCCCC#C UMIPWJGWASORKV-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0011203.7A GB0011203D0 (en) | 2000-05-09 | 2000-05-09 | Chemical compounds |
| GB0011203 | 2000-05-09 | ||
| PCT/GB2001/002004 WO2001085749A1 (en) | 2000-05-09 | 2001-05-08 | Anti-viral pyrimidine nucleoside analogues |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60101223D1 DE60101223D1 (de) | 2003-12-18 |
| DE60101223T2 true DE60101223T2 (de) | 2004-09-02 |
Family
ID=9891276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60101223T Expired - Fee Related DE60101223T2 (de) | 2000-05-09 | 2001-05-08 | Antivirale pyrimidin nucleoside derivate |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7019135B2 (enExample) |
| EP (1) | EP1280813B1 (enExample) |
| JP (1) | JP2003532735A (enExample) |
| AT (1) | ATE254132T1 (enExample) |
| AU (1) | AU780879B2 (enExample) |
| CA (1) | CA2406633A1 (enExample) |
| DE (1) | DE60101223T2 (enExample) |
| DK (1) | DK1280813T3 (enExample) |
| ES (1) | ES2210153T3 (enExample) |
| GB (1) | GB0011203D0 (enExample) |
| NZ (1) | NZ521877A (enExample) |
| PT (1) | PT1280813E (enExample) |
| TR (1) | TR200302313T4 (enExample) |
| WO (1) | WO2001085749A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7462605B2 (en) | 1998-01-23 | 2008-12-09 | Celmed Oncology (Usa), Inc. | Phosphoramidate compounds and methods of use |
| EP1167972B1 (en) | 1998-01-23 | 2017-03-08 | Kiadis Pharma Intellectual Property B.V. | Enzyme catalyzed therapeutic agents |
| US6683061B1 (en) | 1999-07-22 | 2004-01-27 | Newbiotics, Inc. | Enzyme catalyzed therapeutic activation |
| CA2378187C (en) | 1999-07-22 | 2011-09-13 | Newbiotics, Inc. | Methods for treating therapy-resistant tumors |
| GB0009486D0 (en) * | 2000-04-17 | 2000-06-07 | Univ Cardiff | Chemical compounds |
| MY164523A (en) | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| ES2624353T3 (es) | 2002-11-15 | 2017-07-13 | Idenix Pharmaceuticals Llc | 2'-Metil nucleósidos en combinación con interferón y mutación de Flaviviridae |
| GB0609178D0 (en) | 2006-05-09 | 2006-06-21 | Univ Cardiff | Novel compounds |
| US7951789B2 (en) | 2006-12-28 | 2011-05-31 | Idenix Pharmaceuticals, Inc. | Compounds and pharmaceutical compositions for the treatment of viral infections |
| CN103842369A (zh) | 2011-03-31 | 2014-06-04 | 埃迪尼克斯医药公司 | 用于治疗病毒感染的化合物和药物组合物 |
| GB201111779D0 (en) * | 2011-07-08 | 2011-08-24 | Univ Cardiff | Chemical compounds |
| US9403863B2 (en) | 2011-09-12 | 2016-08-02 | Idenix Pharmaceuticals Llc | Substituted carbonyloxymethylphosphoramidate compounds and pharmaceutical compositions for the treatment of viral infections |
| TW201331221A (zh) | 2011-10-14 | 2013-08-01 | Idenix Pharmaceuticals Inc | 嘌呤核苷酸化合物類之經取代的３’，５’－環磷酸酯及用於治療病毒感染之醫藥組成物 |
| US9296778B2 (en) | 2012-05-22 | 2016-03-29 | Idenix Pharmaceuticals, Inc. | 3′,5′-cyclic phosphate prodrugs for HCV infection |
| EP2852604B1 (en) | 2012-05-22 | 2017-04-12 | Idenix Pharmaceuticals LLC | 3',5'-cyclic phosphoramidate prodrugs for hcv infection |
| HK1203514A1 (en) | 2012-05-22 | 2015-10-30 | Idenix Pharmaceuticals Llc | D-amino acid compounds for liver disease |
| PT2861611T (pt) | 2012-05-25 | 2016-10-11 | Janssen Sciences Ireland Uc | Nucleósidos de espirooxetano de uracilo |
| WO2014052638A1 (en) | 2012-09-27 | 2014-04-03 | Idenix Pharmaceuticals, Inc. | Esters and malonates of sate prodrugs |
| CN104936970A (zh) | 2012-10-08 | 2015-09-23 | 埃迪尼克斯医药公司 | 用于hcv感染的2′-氯核苷类似物 |
| WO2014066239A1 (en) | 2012-10-22 | 2014-05-01 | Idenix Pharmaceuticals, Inc. | 2',4'-bridged nucleosides for hcv infection |
| WO2014099941A1 (en) | 2012-12-19 | 2014-06-26 | Idenix Pharmaceuticals, Inc. | 4'-fluoro nucleosides for the treatment of hcv |
| WO2014137930A1 (en) | 2013-03-04 | 2014-09-12 | Idenix Pharmaceuticals, Inc. | Thiophosphate nucleosides for the treatment of hcv |
| EP2970358B1 (en) | 2013-03-04 | 2021-06-30 | Idenix Pharmaceuticals LLC | 3'-deoxy nucleosides for the treatment of hcv |
| US20140271547A1 (en) | 2013-03-13 | 2014-09-18 | Idenix Pharmaceuticals, Inc. | Amino acid phosphoramidate pronucleotides of 2'-cyano, azido and amino nucleosides for the treatment of hcv |
| WO2014165542A1 (en) | 2013-04-01 | 2014-10-09 | Idenix Pharmaceuticals, Inc. | 2',4'-fluoro nucleosides for the treatment of hcv |
| US10005779B2 (en) | 2013-06-05 | 2018-06-26 | Idenix Pharmaceuticals Llc | 1′,4′-thio nucleosides for the treatment of HCV |
| WO2015017713A1 (en) | 2013-08-01 | 2015-02-05 | Idenix Pharmaceuticals, Inc. | D-amino acid phosphoramidate pronucleotides of halogeno pyrimidine compounds for liver disease |
| WO2015161137A1 (en) | 2014-04-16 | 2015-10-22 | Idenix Pharmaceuticals, Inc. | 3'-substituted methyl or alkynyl nucleosides for the treatment of hcv |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62255499A (ja) * | 1986-04-28 | 1987-11-07 | Teijin Ltd | 螢光性ヌクレオシド又はヌクレオチド |
| GB9708611D0 (en) * | 1997-04-28 | 1997-06-18 | Univ Cardiff | Chemical compounds |
| GB9716231D0 (en) * | 1997-07-31 | 1997-10-08 | Amersham Int Ltd | Base analogues |
-
2000
- 2000-05-09 GB GBGB0011203.7A patent/GB0011203D0/en not_active Ceased
-
2001
- 2001-05-08 PT PT01928079T patent/PT1280813E/pt unknown
- 2001-05-08 AT AT01928079T patent/ATE254132T1/de not_active IP Right Cessation
- 2001-05-08 DE DE60101223T patent/DE60101223T2/de not_active Expired - Fee Related
- 2001-05-08 CA CA002406633A patent/CA2406633A1/en not_active Abandoned
- 2001-05-08 AU AU54945/01A patent/AU780879B2/en not_active Ceased
- 2001-05-08 JP JP2001582349A patent/JP2003532735A/ja active Pending
- 2001-05-08 ES ES01928079T patent/ES2210153T3/es not_active Expired - Lifetime
- 2001-05-08 TR TR2003/02313T patent/TR200302313T4/xx unknown
- 2001-05-08 EP EP01928079A patent/EP1280813B1/en not_active Expired - Lifetime
- 2001-05-08 WO PCT/GB2001/002004 patent/WO2001085749A1/en not_active Ceased
- 2001-05-08 NZ NZ521877A patent/NZ521877A/en unknown
- 2001-05-08 DK DK01928079T patent/DK1280813T3/da active
- 2001-05-08 US US10/275,635 patent/US7019135B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DK1280813T3 (da) | 2004-03-22 |
| AU5494501A (en) | 2001-11-20 |
| ES2210153T3 (es) | 2004-07-01 |
| US20030176370A1 (en) | 2003-09-18 |
| CA2406633A1 (en) | 2001-11-15 |
| DE60101223D1 (de) | 2003-12-18 |
| JP2003532735A (ja) | 2003-11-05 |
| TR200302313T4 (tr) | 2004-01-21 |
| EP1280813A1 (en) | 2003-02-05 |
| WO2001085749A1 (en) | 2001-11-15 |
| AU780879B2 (en) | 2005-04-21 |
| NZ521877A (en) | 2004-11-26 |
| EP1280813B1 (en) | 2003-11-12 |
| PT1280813E (pt) | 2004-03-31 |
| ATE254132T1 (de) | 2003-11-15 |
| GB0011203D0 (en) | 2000-06-28 |
| US7019135B2 (en) | 2006-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8339 | Ceased/non-payment of the annual fee |