UA61997C2 - Nucleosides with bicyclic sugar constituent, oligonucleotide and antiviral pharmaceutical composition - Google Patents
Nucleosides with bicyclic sugar constituent, oligonucleotide and antiviral pharmaceutical composition Download PDFInfo
- Publication number
- UA61997C2 UA61997C2 UA2000116545A UA2000116545A UA61997C2 UA 61997 C2 UA61997 C2 UA 61997C2 UA 2000116545 A UA2000116545 A UA 2000116545A UA 2000116545 A UA2000116545 A UA 2000116545A UA 61997 C2 UA61997 C2 UA 61997C2
- Authority
- UA
- Ukraine
- Prior art keywords
- nucleosides
- solution
- dioxabicyclo
- pharmaceutical composition
- mmol
- Prior art date
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- 239000002777 nucleoside Substances 0.000 title claims abstract description 44
- 108091034117 Oligonucleotide Proteins 0.000 title claims abstract description 21
- 125000003835 nucleoside group Chemical group 0.000 title claims abstract description 21
- 125000002619 bicyclic group Chemical group 0.000 title claims description 21
- 235000000346 sugar Nutrition 0.000 title claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 title claims 5
- 230000000840 anti-viral effect Effects 0.000 title claims 2
- 239000000470 constituent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 10
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- 239000001226 triphosphate Substances 0.000 claims description 8
- 235000011178 triphosphate Nutrition 0.000 claims description 7
- 229940113082 thymine Drugs 0.000 claims description 5
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 4
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 4
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 claims description 4
- 229940035893 uracil Drugs 0.000 claims description 4
- 241000700605 Viruses Species 0.000 claims description 3
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 2
- 229930024421 Adenine Natural products 0.000 claims description 2
- UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 claims description 2
- 229960000643 adenine Drugs 0.000 claims description 2
- 229940104302 cytosine Drugs 0.000 claims description 2
- 239000001177 diphosphate Substances 0.000 claims description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 2
- 235000011180 diphosphates Nutrition 0.000 claims description 2
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 claims description 2
- 241000725303 Human immunodeficiency virus Species 0.000 claims 4
- 241000700721 Hepatitis B virus Species 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
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- 238000004587 chromatography analysis Methods 0.000 description 34
- 239000000377 silicon dioxide Substances 0.000 description 33
- 239000000203 mixture Substances 0.000 description 32
- 238000005481 NMR spectroscopy Methods 0.000 description 27
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
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- 238000011282 treatment Methods 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
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- 238000006243 chemical reaction Methods 0.000 description 12
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- 230000005494 condensation Effects 0.000 description 11
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 10
- -1 nucleoside triphosphates Chemical class 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
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- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
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- 230000022131 cell cycle Effects 0.000 description 1
- DDYAZDRFUVZBMM-UHFFFAOYSA-N chloro-[chloro-di(propan-2-yl)silyl]oxy-di(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(C(C)C)O[Si](Cl)(C(C)C)C(C)C DDYAZDRFUVZBMM-UHFFFAOYSA-N 0.000 description 1
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- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical class ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
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- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
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- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
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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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
-
- 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
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
-
- 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
- C07H19/16—Purine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8671998P | 1998-05-26 | 1998-05-26 | |
| PCT/US1999/011442 WO1999060855A1 (en) | 1998-05-26 | 1999-05-24 | Novel nucleosides having bicyclic sugar moiety |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA61997C2 true UA61997C2 (en) | 2003-12-15 |
Family
ID=22200439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2000116545A UA61997C2 (en) | 1998-05-26 | 1999-05-24 | Nucleosides with bicyclic sugar constituent, oligonucleotide and antiviral pharmaceutical composition |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6403566B1 (de) |
| EP (1) | EP1082012A4 (de) |
| JP (1) | JP2002516256A (de) |
| CN (1) | CN1311630A (de) |
| AU (1) | AU757724B2 (de) |
| BR (1) | BR9911596A (de) |
| CA (1) | CA2333380A1 (de) |
| HR (1) | HRP20000751A2 (de) |
| HU (1) | HUP0102152A3 (de) |
| IL (1) | IL139420A0 (de) |
| MX (1) | MXPA00011473A (de) |
| NO (1) | NO20005938L (de) |
| NZ (1) | NZ507913A (de) |
| PL (1) | PL344303A1 (de) |
| RU (1) | RU2211223C2 (de) |
| SI (1) | SI20474A (de) |
| SK (1) | SK17432000A3 (de) |
| UA (1) | UA61997C2 (de) |
| WO (1) | WO1999060855A1 (de) |
| YU (1) | YU73600A (de) |
| ZA (1) | ZA200006315B (de) |
Families Citing this family (99)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040033977A1 (en) * | 1990-08-14 | 2004-02-19 | Bennett C. Frank | Oligonucleotide modulation of cell adhesion |
| US7119184B2 (en) * | 1991-08-12 | 2006-10-10 | Isis Pharmaceuticals, Inc. | Oligonucleotides having A-DNA form and B-DNA form conformational geometry |
| CA2279673A1 (en) * | 1995-12-15 | 1997-06-16 | Enzo Therapeutics, Inc. | Property effecting and/or property exhibiting constructs for the expression of non-native nucleic acids for therapeutic and diagnostic uses |
| US6833361B2 (en) * | 1998-05-26 | 2004-12-21 | Ribapharm, Inc. | Nucleosides having bicyclic sugar moiety |
| US7084125B2 (en) | 1999-03-18 | 2006-08-01 | Exiqon A/S | Xylo-LNA analogues |
| US6900186B1 (en) * | 1999-06-21 | 2005-05-31 | Murdock Children's Research Institute | Method for the prophylaxis and/or treatment of medical disorders |
| AU2003295387A1 (en) * | 2002-11-05 | 2004-06-03 | Isis Parmaceuticals, Inc. | Modified oligonucleotides for use in rna interference |
| CN1852915A (zh) * | 2003-07-25 | 2006-10-25 | 艾登尼科斯（开曼）有限公司 | 治疗包括丙型肝炎的黄病毒科病毒所致疾病的嘌呤核苷类似物 |
| DK1661905T3 (da) | 2003-08-28 | 2012-07-23 | Takeshi Imanishi | Hidtil ukendte syntetiske nukleinsyrer af N-O-krydsbindingstype |
| US7480382B2 (en) * | 2003-09-30 | 2009-01-20 | Microsoft Corporation | Image file container |
| US20050182252A1 (en) | 2004-02-13 | 2005-08-18 | Reddy K. R. | Novel 2'-C-methyl nucleoside derivatives |
| CN103301475B (zh) | 2005-12-28 | 2016-08-03 | 斯克里普斯研究所 | 药物组合物和表达载体以及调节基因表达的方法和核酸分子的应用 |
| LT2494993T (lt) | 2007-05-04 | 2018-12-27 | Marina Biotech, Inc. | Aminorūgščių lipidai ir jų panaudojimas |
| US20100015708A1 (en) * | 2008-06-18 | 2010-01-21 | Mdrna, Inc. | Ribonucleic acids with non-standard bases and uses thereof |
| CA2739464C (en) * | 2008-10-03 | 2020-03-31 | Curna, Inc. | Treatment of apolipoprotein-a1 related diseases by inhibition of natural antisense transcript to apolipoprotein-a1 |
| CA2739046A1 (en) | 2008-10-16 | 2010-04-22 | Marina Biotech, Inc. | Process and compositions for liposomal and effective delivery of nucleic acids |
| US8987435B2 (en) | 2008-10-24 | 2015-03-24 | Isis Pharmaceuticals, Inc. | Oligomeric compounds and methods |
| RU2569182C2 (ru) | 2008-12-04 | 2015-11-20 | КьюРНА,Инк.,US | Лечение заболеваний, связанных с фактором роста эндотелия сосудов (vegf), посредством ингибирования природного антисмыслового транскрипта к vegf |
| KR101829469B1 (ko) * | 2008-12-04 | 2018-03-30 | 큐알엔에이, 인크. | Ｅｐｏ에 대한 천연 안티센스 전사체의 억제에 의해 에리트로포에틴(ｅｐｏ) 관련된 질환의 치료 |
| KR101866152B1 (ko) | 2008-12-04 | 2018-06-08 | 큐알엔에이, 인크. | 종양 억제 유전자에 대한 천연 안티센스 전사체의 억제에 의해 종양 억제 유전자 관련된 질환의 치료 |
| KR101682735B1 (ko) | 2009-02-12 | 2016-12-06 | 큐알엔에이, 인크. | 뇌 유래된 신경영양성 인자 (ｂｄｎｆ)에 대한 자연 안티센스 전사체의 저해에 의한 뇌 유래된 신경영양성 인자 (ｂｄｎｆ) 관련된 질환의 치료 |
| MX2011009751A (es) | 2009-03-16 | 2011-09-29 | Opko Curna Llc | Tratamiento de enfermedades relacionadas con factor nuclear (eritroide derivado 2) tipo 2 (nrf2) por inhibicion del transcrito antisentido natural a nrf2. |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2103918T3 (es) * | 1991-10-17 | 1997-10-01 | Ciba Geigy Ag | Nucleosidos biciclicos, oligonucleotidos, procedimiento para su obtencion y productos intermedios. |
| JP3756313B2 (ja) * | 1997-03-07 | 2006-03-15 | 武 今西 | 新規ビシクロヌクレオシド及びオリゴヌクレオチド類縁体 |
| DE69829760T3 (de) | 1997-09-12 | 2016-04-14 | Exiqon A/S | Bi- und tri-zyklische - nukleosid, nukleotid und oligonukleotid-analoga |
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1999
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- 1999-05-24 CN CN99809057A patent/CN1311630A/zh active Pending
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- 1999-05-24 SI SI9920038A patent/SI20474A/sl not_active IP Right Cessation
- 1999-05-24 HR HR20000751A patent/HRP20000751A2/hr not_active Application Discontinuation
- 1999-05-24 BR BR9911596-4A patent/BR9911596A/pt not_active IP Right Cessation
- 1999-05-24 IL IL13942099A patent/IL139420A0/xx unknown
- 1999-05-24 NZ NZ507913A patent/NZ507913A/xx unknown
- 1999-05-24 CA CA002333380A patent/CA2333380A1/en not_active Abandoned
- 1999-05-24 SK SK1743-2000A patent/SK17432000A3/sk unknown
- 1999-05-24 JP JP2000550331A patent/JP2002516256A/ja not_active Withdrawn
- 1999-05-24 YU YU73600A patent/YU73600A/sh unknown
- 1999-05-24 HU HU0102152A patent/HUP0102152A3/hu unknown
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| SK17432000A3 (sk) | 2001-07-10 |
| JP2002516256A (ja) | 2002-06-04 |
| HUP0102152A2 (hu) | 2001-12-28 |
| YU73600A (sh) | 2003-08-29 |
| CA2333380A1 (en) | 1999-12-02 |
| ZA200006315B (en) | 2002-02-04 |
| HRP20000751A2 (en) | 2001-12-31 |
| CN1311630A (zh) | 2001-09-05 |
| AU757724B2 (en) | 2003-03-06 |
| PL344303A1 (en) | 2001-10-22 |
| BR9911596A (pt) | 2001-10-02 |
| MXPA00011473A (es) | 2002-04-24 |
| EP1082012A1 (de) | 2001-03-14 |
| SI20474A (sl) | 2001-08-31 |
| NO20005938L (no) | 2001-01-16 |
| US6403566B1 (en) | 2002-06-11 |
| WO1999060855A1 (en) | 1999-12-02 |
| IL139420A0 (en) | 2001-11-25 |
| NO20005938D0 (no) | 2000-11-24 |
| EP1082012A4 (de) | 2002-01-16 |
| RU2211223C2 (ru) | 2003-08-27 |
| AU4010099A (en) | 1999-12-13 |
| HUP0102152A3 (en) | 2002-04-29 |
| NZ507913A (en) | 2003-02-28 |
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