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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- 101500025412 Mus musculus Processed cyclic AMP-responsive element-binding protein 3-like protein 1 Proteins 0.000 description 1
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- 241000256856 Vespidae Species 0.000 description 1
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000003838 adenosines Chemical class 0.000 description 1
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- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
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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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- 230000003197 catalytic effect Effects 0.000 description 1
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- 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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- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
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- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 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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- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 1
- 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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- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-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)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (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 (fr) | 1998-05-26 | 1999-05-24 | Nouveaux nucleosides comportant une fraction sucre bicyclique |
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 (fr) |
| EP (1) | EP1082012A4 (fr) |
| JP (1) | JP2002516256A (fr) |
| CN (1) | CN1311630A (fr) |
| AU (1) | AU757724B2 (fr) |
| BR (1) | BR9911596A (fr) |
| CA (1) | CA2333380A1 (fr) |
| HR (1) | HRP20000751A2 (fr) |
| HU (1) | HUP0102152A3 (fr) |
| IL (1) | IL139420A0 (fr) |
| MX (1) | MXPA00011473A (fr) |
| NO (1) | NO20005938L (fr) |
| NZ (1) | NZ507913A (fr) |
| PL (1) | PL344303A1 (fr) |
| RU (1) | RU2211223C2 (fr) |
| SI (1) | SI20474A (fr) |
| SK (1) | SK17432000A3 (fr) |
| UA (1) | UA61997C2 (fr) |
| WO (1) | WO1999060855A1 (fr) |
| YU (1) | YU73600A (fr) |
| ZA (1) | ZA200006315B (fr) |
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 (fr) * | 1995-12-15 | 1997-06-16 | Enzo Therapeutics, Inc. | Construits possedant certaines proprietes et/ou modifiant certaines proprietes pour l'expression d'acide nucleique allogene pour utilisation therapeutique ou de diagnotisque |
| 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 |
| AU2003291755A1 (en) * | 2002-11-05 | 2004-06-07 | Isis Pharmaceuticals, Inc. | Oligomers comprising modified bases for binding cytosine and uracil or thymine and their use |
| US20050075309A1 (en) | 2003-07-25 | 2005-04-07 | Richard Storer | Purine nucleoside analogues for treating Flaviviridae including hepatitis C |
| EP1661905B9 (fr) * | 2003-08-28 | 2012-12-19 | IMANISHI, Takeshi | Nouveaux acides nucleiques artificiels de type a liaison n-o reticulee |
| 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 |
| JP5713377B2 (ja) | 2005-12-28 | 2015-05-07 | ザ スクリプス リサーチ インスティテュート | 薬物標的としての天然アンチセンスおよび非コードｒｎａ転写物 |
| HUE040417T2 (hu) | 2007-05-04 | 2019-03-28 | Marina Biotech Inc | Aminosavlipidek és alkalmazásuk |
| US20100015708A1 (en) * | 2008-06-18 | 2010-01-21 | Mdrna, Inc. | Ribonucleic acids with non-standard bases and uses thereof |
| CN102239260B (zh) * | 2008-10-03 | 2017-04-12 | 库尔纳公司 | 通过抑制针对载脂蛋白‑a1的天然反义转录物治疗载脂蛋白‑a1相关疾病 |
| JP2012505913A (ja) | 2008-10-16 | 2012-03-08 | マリーナ バイオテック，インコーポレイテッド | 遺伝子発現を抑制する治療におけるリポソームによる効率的な送達のプロセスおよび組成物 |
| EP2447274B1 (fr) | 2008-10-24 | 2017-10-04 | Ionis Pharmaceuticals, Inc. | Composants oligomères et procédés |
| ES2629630T3 (es) | 2008-12-04 | 2017-08-11 | Curna, Inc. | Tratamiento de enfermedades relacionadas con eritropoyetina (EPO) mediante inhibición del transcrito antisentido natural a EPO |
| US20110294870A1 (en) | 2008-12-04 | 2011-12-01 | Opko Curna, Llc | Treatment of tumor suppressor gene related diseases by inhibition of natural antisense transcript to the gene |
| ES2600781T3 (es) | 2008-12-04 | 2017-02-10 | Curna, Inc. | Tratamiento para enfermedades relacionadas con el factor de crecimiento del endotelio vascular (vegf) mediante la inhibición de transcritos antisentido naturales de vegf |
| ES2762610T3 (es) | 2009-02-12 | 2020-05-25 | Curna Inc | Tratamiento de enfermedades relacionadas con el factor neurotrófico derivado de cerebro (BDNF) por inhibición de transcrito antisentido natural para BDNF |
| CN102482677B (zh) | 2009-03-16 | 2017-10-17 | 库尔纳公司 | 通过抑制nrf2的天然反义转录物治疗核因子(红细胞衍生2)‑样2(nrf2)相关疾病 |
| WO2010107740A2 (fr) | 2009-03-17 | 2010-09-23 | Curna, Inc. | Traitement des maladies associées à l'homologue du delta-like 1 (dlk1) par inhibition du transcrit antisens naturel de dlk1 |
| CN103223177B (zh) | 2009-05-06 | 2016-08-10 | 库尔纳公司 | 通过针对脂质转运和代谢基因的天然反义转录物的抑制治疗脂质转运和代谢基因相关疾病 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP0538194B1 (fr) * | 1991-10-17 | 1997-06-04 | Novartis AG | Nucléosides et oligonucléosides bicycliques, leur procédé de préparation et leurs intermédiaires |
| 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 |
| JP4236812B2 (ja) | 1997-09-12 | 2009-03-11 | エクシコン エ／エス | オリゴヌクレオチド類似体 |
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- 1999-05-24 WO PCT/US1999/011442 patent/WO1999060855A1/fr not_active Ceased
- 1999-05-24 UA UA2000116545A patent/UA61997C2/uk unknown
- 1999-05-24 RU RU2000129663/04A patent/RU2211223C2/ru not_active IP Right Cessation
- 1999-05-24 AU AU40100/99A patent/AU757724B2/en not_active Ceased
- 1999-05-24 HU HU0102152A patent/HUP0102152A3/hu unknown
- 1999-05-24 PL PL99344303A patent/PL344303A1/xx not_active Application Discontinuation
- 1999-05-24 SI SI9920038A patent/SI20474A/sl not_active IP Right Cessation
- 1999-05-24 NZ NZ507913A patent/NZ507913A/xx unknown
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- 1999-05-24 IL IL13942099A patent/IL139420A0/xx unknown
- 1999-05-24 BR BR9911596-4A patent/BR9911596A/pt not_active IP Right Cessation
- 1999-05-24 CA CA002333380A patent/CA2333380A1/fr not_active Abandoned
- 1999-05-24 EP EP99923288A patent/EP1082012A4/fr not_active Withdrawn
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| HRP20000751A2 (en) | 2001-12-31 |
| CA2333380A1 (fr) | 1999-12-02 |
| MXPA00011473A (es) | 2002-04-24 |
| US6403566B1 (en) | 2002-06-11 |
| WO1999060855A1 (fr) | 1999-12-02 |
| JP2002516256A (ja) | 2002-06-04 |
| PL344303A1 (en) | 2001-10-22 |
| CN1311630A (zh) | 2001-09-05 |
| AU4010099A (en) | 1999-12-13 |
| NO20005938L (no) | 2001-01-16 |
| ZA200006315B (en) | 2002-02-04 |
| NZ507913A (en) | 2003-02-28 |
| NO20005938D0 (no) | 2000-11-24 |
| EP1082012A1 (fr) | 2001-03-14 |
| AU757724B2 (en) | 2003-03-06 |
| SI20474A (sl) | 2001-08-31 |
| BR9911596A (pt) | 2001-10-02 |
| EP1082012A4 (fr) | 2002-01-16 |
| SK17432000A3 (sk) | 2001-07-10 |
| HUP0102152A3 (en) | 2002-04-29 |
| YU73600A (sh) | 2003-08-29 |
| HUP0102152A2 (hu) | 2001-12-28 |
| IL139420A0 (en) | 2001-11-25 |
| RU2211223C2 (ru) | 2003-08-27 |
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