SU539532A3 - Способ получени (6)замещенных производных аденозина - Google Patents
Способ получени (6)замещенных производных аденозинаInfo
- Publication number
- SU539532A3 SU539532A3 SU1812966A SU1812966A SU539532A3 SU 539532 A3 SU539532 A3 SU 539532A3 SU 1812966 A SU1812966 A SU 1812966A SU 1812966 A SU1812966 A SU 1812966A SU 539532 A3 SU539532 A3 SU 539532A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- chloro
- ribofuranosyl
- hydroxymethyl
- triacetyl
- hydrochloride
- Prior art date
Links
- 150000003835 adenosine derivatives Chemical class 0.000 title description 2
- 238000000034 method Methods 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- -1 hydrochloric Chemical class 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- AVJCDPZZYDVZIL-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanol;hydrochloride Chemical compound Cl.NCC1=CC=CC=C1CO AVJCDPZZYDVZIL-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YRZACROWFWGSOG-UHFFFAOYSA-N Cl.OCC=1C(=C(CN)C=CC1)C Chemical compound Cl.OCC=1C(=C(CN)C=CC1)C YRZACROWFWGSOG-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- WVVZFIHFMONLCJ-UHFFFAOYSA-N Cl.CC=1C=CC(=C(CN)C1)[N+](=O)[O-] Chemical compound Cl.CC=1C=CC(=C(CN)C1)[N+](=O)[O-] WVVZFIHFMONLCJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010062717 Increased upper airway secretion Diseases 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 208000026435 phlegm Diseases 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229960005305 adenosine Drugs 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000837 carbohydrate group Chemical group 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000008223 ribosides Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material 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
- C07H19/16—Purine radicals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2136624A DE2136624A1 (de) | 1971-07-22 | 1971-07-22 | N (6)-substituierte adenosin-derivate und verfahren zur herstellung derselben |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU539532A3 true SU539532A3 (ru) | 1976-12-15 |
Family
ID=5814433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1812966A SU539532A3 (ru) | 1971-07-22 | 1972-07-20 | Способ получени (6)замещенных производных аденозина |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3845035A (enExample) |
| AR (2) | AR192658A1 (enExample) |
| AT (2) | AT317446B (enExample) |
| CA (1) | CA979891A (enExample) |
| CH (2) | CH570420A5 (enExample) |
| DE (1) | DE2136624A1 (enExample) |
| ES (1) | ES405022A1 (enExample) |
| FR (1) | FR2146493B1 (enExample) |
| GB (1) | GB1340643A (enExample) |
| HU (1) | HU171081B (enExample) |
| NL (1) | NL7210023A (enExample) |
| SU (1) | SU539532A3 (enExample) |
| ZA (1) | ZA724891B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2324698C1 (ru) * | 2007-02-05 | 2008-05-20 | Институт биоорганической химии им. академиков М.М. Шемякина и Ю.А. Овчинникова Российской академии наук | Способ получения 2-хлораденозина |
| US8877905B2 (en) | 2008-06-11 | 2014-11-04 | Lasergen, Inc. | Nucleotides and nucleosides and methods for their use in DNA sequencing |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4501735A (en) * | 1983-12-05 | 1985-02-26 | Warner-Lambert Company | N6-(1- and 2-benzocycloalkyl) adenosines |
| US4657898A (en) * | 1984-06-22 | 1987-04-14 | Warner-Lambert Company | N6 -substituted adenosines and method of use |
| FR2575751B1 (fr) * | 1985-01-08 | 1987-04-03 | Pasteur Institut | Nouveaux nucleosides de derives de l'adenosine, leur preparation et leurs applications biologiques |
| US5284834A (en) * | 1985-03-29 | 1994-02-08 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Adenosine functionalized congeners as cardiovascular treating agents for animals and methods for using same |
| US4974683A (en) | 1987-12-31 | 1990-12-04 | Sukup Manufacturing Company | Ridge tillage attachment for planters |
| JPH0725785B2 (ja) * | 1989-01-11 | 1995-03-22 | 日本臓器製薬株式会社 | アデノシン誘導体及び該化合物を有効成分として含有する医薬組成物 |
| DK0550631T3 (da) * | 1990-09-25 | 1997-01-20 | Rhone Poulenc Rorer Int | Forbindelser med blodtrykssænkende virkning og virkning mod iskæmi |
| US5561134A (en) * | 1990-09-25 | 1996-10-01 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Compounds having antihypertensive, cardioprotective, anti-ischemic and antilipolytic properties |
| WO1994002497A1 (en) * | 1992-07-15 | 1994-02-03 | The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Sulfo-derivatives of adenosine |
| CZ294538B6 (cs) * | 2002-12-30 | 2005-01-12 | Ústav Experimentální Botaniky Akademie Vědčeské Re | Substituční deriváty N6-benzyladenosinu, způsob jejich přípravy, jejich použití pro přípravu léčiv, kosmetických přípravků a růstových regulátorů, farmaceutické přípravky, kosmetické přípravky a růstové regulátory tyto sloučeniny obsahující |
| US7897737B2 (en) | 2006-12-05 | 2011-03-01 | Lasergen, Inc. | 3′-OH unblocked, nucleotides and nucleosides, base modified with photocleavable, terminating groups and methods for their use in DNA sequencing |
| JP6196972B2 (ja) | 2011-09-13 | 2017-09-13 | レーザーゲン インコーポレイテッド | ５−メトキシ３’−ｏｈ非遮断高速光開裂性末端ヌクレオチドおよび核酸配列決定のための方法 |
-
1971
- 1971-07-22 DE DE2136624A patent/DE2136624A1/de active Pending
-
1972
- 1972-06-18 GB GB3353772A patent/GB1340643A/en not_active Expired
- 1972-07-12 US US00271098A patent/US3845035A/en not_active Expired - Lifetime
- 1972-07-17 ZA ZA724891A patent/ZA724891B/xx unknown
- 1972-07-17 AR AR243105A patent/AR192658A1/es active
- 1972-07-19 CH CH1079572A patent/CH570420A5/xx not_active IP Right Cessation
- 1972-07-19 CH CH1061775A patent/CH569035A5/xx not_active IP Right Cessation
- 1972-07-20 SU SU1812966A patent/SU539532A3/ru active
- 1972-07-20 ES ES405022A patent/ES405022A1/es not_active Expired
- 1972-07-20 CA CA147,625A patent/CA979891A/en not_active Expired
- 1972-07-20 NL NL7210023A patent/NL7210023A/xx unknown
- 1972-07-21 AT AT628872A patent/AT317446B/de not_active IP Right Cessation
- 1972-07-21 FR FR7226450A patent/FR2146493B1/fr not_active Expired
- 1972-07-21 HU HU72BO00001387A patent/HU171081B/hu unknown
- 1972-07-21 AT AT790673*7A patent/AT327405B/de not_active IP Right Cessation
- 1972-12-26 AR AR245831A patent/AR193000A1/es active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2324698C1 (ru) * | 2007-02-05 | 2008-05-20 | Институт биоорганической химии им. академиков М.М. Шемякина и Ю.А. Овчинникова Российской академии наук | Способ получения 2-хлораденозина |
| US8877905B2 (en) | 2008-06-11 | 2014-11-04 | Lasergen, Inc. | Nucleotides and nucleosides and methods for their use in DNA sequencing |
| US9200319B2 (en) | 2008-06-11 | 2015-12-01 | Lasergen, Inc. | Nucleotides and nucleosides and methods for their use in DNA sequencing |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2146493A1 (enExample) | 1973-03-02 |
| CH570420A5 (enExample) | 1975-12-15 |
| CH569035A5 (enExample) | 1975-11-14 |
| AT327405B (de) | 1976-01-26 |
| NL7210023A (enExample) | 1973-01-24 |
| ES405022A1 (es) | 1975-07-16 |
| AR192658A1 (es) | 1973-02-28 |
| AT317446B (de) | 1974-08-26 |
| ZA724891B (en) | 1973-05-30 |
| FR2146493B1 (enExample) | 1976-04-16 |
| ATA790673A (de) | 1975-04-15 |
| AR193000A1 (es) | 1973-03-21 |
| HU171081B (hu) | 1977-11-28 |
| GB1340643A (en) | 1973-12-12 |
| DE2136624A1 (de) | 1973-02-08 |
| US3845035A (en) | 1974-10-29 |
| CA979891A (en) | 1975-12-16 |
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