SU576955A3 - Способ получени производных аденозина - Google Patents
Способ получени производных аденозинаInfo
- Publication number
- SU576955A3 SU576955A3 SU7301959113A SU1959113A SU576955A3 SU 576955 A3 SU576955 A3 SU 576955A3 SU 7301959113 A SU7301959113 A SU 7301959113A SU 1959113 A SU1959113 A SU 1959113A SU 576955 A3 SU576955 A3 SU 576955A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- theory
- derivatives
- hydrazine
- adenosine
- adenosine derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 3
- 150000003835 adenosine derivatives Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 description 9
- 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 7
- -1 cyclic acetals Chemical class 0.000 description 7
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 5
- 229960005305 adenosine Drugs 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZGOROAWVRUSDDV-UHFFFAOYSA-N 4-(bromomethyl)benzohydrazide Chemical compound NNC(=O)C1=CC=C(CBr)C=C1 ZGOROAWVRUSDDV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZHWHMUIGIKPSJN-WOUKDFQISA-N (2r,3r,4s,5r)-2-(6-aminopurin-9-yl)-2-ethyl-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC2=C(N)N=CN=C2N1[C@]1(CC)O[C@H](CO)[C@@H](O)[C@H]1O ZHWHMUIGIKPSJN-WOUKDFQISA-N 0.000 description 1
- XOCBRDRMXFKQPV-HMTTWLPMSA-N 1-[(2R,3R,4R,5S)-4,5-diacetyl-5-(6-aminopurin-9-yl)-3,4-dihydroxy-2-(hydroxymethyl)oxolan-3-yl]ethanone Chemical compound C(C)(=O)[C@@]1([C@]([C@@](O[C@@H]1CO)(N1C=NC=2C(N)=NC=NC1=2)C(C)=O)(O)C(C)=O)O XOCBRDRMXFKQPV-HMTTWLPMSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- VUYGJYAPDGKPBF-UHFFFAOYSA-N 4-(bromomethyl)benzoyl bromide Chemical compound BrCC1=CC=C(C(Br)=O)C=C1 VUYGJYAPDGKPBF-UHFFFAOYSA-N 0.000 description 1
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 description 1
- PKBGHORNUFQAAW-UHFFFAOYSA-N 4-chlorobenzohydrazide Chemical compound NNC(=O)C1=CC=C(Cl)C=C1 PKBGHORNUFQAAW-UHFFFAOYSA-N 0.000 description 1
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- REKQLYUAUXYJSZ-UHFFFAOYSA-N 4-methoxybenzohydrazide Chemical compound COC1=CC=C(C(=O)NN)C=C1 REKQLYUAUXYJSZ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000003838 adenosines Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 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
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
-
- 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 |
|---|---|---|---|
| DE19702060189 DE2060189A1 (de) | 1970-12-08 | 1970-12-08 | Neue Adenosin-Derivate und Verfahren zu deren Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU576955A3 true SU576955A3 (ru) | 1977-10-15 |
Family
ID=5790242
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1721738A SU444368A3 (ru) | 1970-12-08 | 1971-12-02 | Способ получения производных аденозина |
| SU7301959113A SU576955A3 (ru) | 1970-12-08 | 1973-08-24 | Способ получени производных аденозина |
| SU1959114A SU515454A3 (ru) | 1970-12-08 | 1973-08-24 | Способ получени производных аденозина |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1721738A SU444368A3 (ru) | 1970-12-08 | 1971-12-02 | Способ получения производных аденозина |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1959114A SU515454A3 (ru) | 1970-12-08 | 1973-08-24 | Способ получени производных аденозина |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3787391A (enExample) |
| AT (3) | AT318821B (enExample) |
| AU (1) | AU452257B2 (enExample) |
| CA (1) | CA960656A (enExample) |
| CH (3) | CH568331A5 (enExample) |
| DE (1) | DE2060189A1 (enExample) |
| ES (1) | ES397613A1 (enExample) |
| FR (1) | FR2117935B1 (enExample) |
| GB (1) | GB1313459A (enExample) |
| HU (1) | HU163227B (enExample) |
| NL (1) | NL7116564A (enExample) |
| SU (3) | SU444368A3 (enExample) |
| ZA (1) | ZA718177B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4495180A (en) * | 1982-06-21 | 1985-01-22 | Merck & Co., Inc. | Prodrugs of Ara-A an antiviral agent |
| US4683223A (en) * | 1985-09-09 | 1987-07-28 | Warner-Lambert Company | N6 -Benzopyrano-and benzothiopyrano adenosines and methods of use |
-
1970
- 1970-12-08 DE DE19702060189 patent/DE2060189A1/de active Pending
-
1971
- 1971-11-22 US US00201174A patent/US3787391A/en not_active Expired - Lifetime
- 1971-12-02 ES ES397613A patent/ES397613A1/es not_active Expired
- 1971-12-02 GB GB5602571A patent/GB1313459A/en not_active Expired
- 1971-12-02 NL NL7116564A patent/NL7116564A/xx unknown
- 1971-12-02 SU SU1721738A patent/SU444368A3/ru active
- 1971-12-03 AU AU36492/71A patent/AU452257B2/en not_active Expired
- 1971-12-03 CH CH828575A patent/CH568331A5/xx not_active IP Right Cessation
- 1971-12-03 CH CH828475A patent/CH568330A5/xx not_active IP Right Cessation
- 1971-12-03 CH CH1764071A patent/CH567045A5/xx not_active IP Right Cessation
- 1971-12-07 HU HUBO1335A patent/HU163227B/hu unknown
- 1971-12-07 AT AT916872A patent/AT318821B/de not_active IP Right Cessation
- 1971-12-07 AT AT1053371A patent/AT312172B/de not_active IP Right Cessation
- 1971-12-07 CA CA129,590A patent/CA960656A/en not_active Expired
- 1971-12-07 AT AT916972A patent/AT318822B/de not_active IP Right Cessation
- 1971-12-07 ZA ZA718177A patent/ZA718177B/xx unknown
- 1971-12-08 FR FR7143996A patent/FR2117935B1/fr not_active Expired
-
1973
- 1973-08-24 SU SU7301959113A patent/SU576955A3/ru active
- 1973-08-24 SU SU1959114A patent/SU515454A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| CH568330A5 (enExample) | 1975-10-31 |
| AU3649271A (en) | 1973-06-07 |
| ES397613A1 (es) | 1975-03-16 |
| AT318821B (de) | 1974-11-25 |
| AU452257B2 (en) | 1974-08-29 |
| CA960656A (en) | 1975-01-07 |
| SU515454A3 (ru) | 1976-05-25 |
| HU163227B (enExample) | 1973-07-28 |
| US3787391A (en) | 1974-01-22 |
| AT312172B (de) | 1973-12-27 |
| DE2060189A1 (de) | 1972-06-15 |
| CH567045A5 (enExample) | 1975-09-30 |
| FR2117935A1 (enExample) | 1972-07-28 |
| FR2117935B1 (enExample) | 1975-03-14 |
| ZA718177B (en) | 1972-09-27 |
| CH568331A5 (enExample) | 1975-10-31 |
| NL7116564A (enExample) | 1972-06-12 |
| AT318822B (de) | 1974-11-25 |
| GB1313459A (en) | 1973-04-11 |
| SU444368A3 (ru) | 1974-09-25 |
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