GB1399670A - Process for preparing adenosine-5-carboxamides - Google Patents
Process for preparing adenosine-5-carboxamidesInfo
- Publication number
- GB1399670A GB1399670A GB1521473A GB1521473A GB1399670A GB 1399670 A GB1399670 A GB 1399670A GB 1521473 A GB1521473 A GB 1521473A GB 1521473 A GB1521473 A GB 1521473A GB 1399670 A GB1399670 A GB 1399670A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- adenosine
- carboxamides
- cycloalkyl
- ester
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 2
- -1 2-methylfuryl Chemical group 0.000 abstract 2
- MWEQTWJABOLLOS-UHFFFAOYSA-L disodium;[[[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-oxidophosphoryl] hydrogen phosphate;trihydrate Chemical compound O.O.O.[Na+].[Na+].C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP([O-])(=O)OP(O)([O-])=O)C(O)C1O MWEQTWJABOLLOS-UHFFFAOYSA-L 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 abstract 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 1
- 125000000232 haloalkynyl group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000005020 hydroxyalkenyl group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 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
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)
Abstract
1399670 Adenosine-5<SP>1</SP>-carboxamides ABBOTT LABORATORIES 29 March 1973 [10 April 1972] 15214/73 Heading C2C Compounds I in which R 1 and R 2 are hydrogen, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 hydroxyalkyl, C 3-7 cycloalkyl, C 2-6 alkenyl, C 2-6 haloalkenyl, C 2-6 hydroxyalkenyl, C 2-6 alkynyl, C 2-6 haloalkynyl, benzyl, phenyl C 1-4 alkyl, C 3-7 cycloalkyl, C 1-4 alkoxy C 1-4 alkyl, substituted phenyl, 2-methylfuryl, di-(C 1-4 alkyl)amino-C 1-4 alkyl or adamantyl or NR 1 R 2 form a heterocyclic ring and their acid addition salts are prepared by reacting an ester of adenosine-5<SP>1</SP>-carboxylic acid or a salt-thereof with an amine HNR 1 R 2 by suspending the ester in a C 1-3 alkanol containing the amine and heating the mixture for at least part of the time above 70‹ C. R 1 is hydrogen and R 2 is allyl, propargyl i-propyl, 2-hydroxyethyl or cyclopropyl.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24277972A | 1972-04-10 | 1972-04-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1399670A true GB1399670A (en) | 1975-07-02 |
Family
ID=22916155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1521473A Expired GB1399670A (en) | 1972-04-10 | 1973-03-29 | Process for preparing adenosine-5-carboxamides |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4913200A (en) |
| CA (1) | CA1082695A (en) |
| CH (1) | CH565175A5 (en) |
| DE (1) | DE2317770A1 (en) |
| FR (1) | FR2179886B1 (en) |
| GB (1) | GB1399670A (en) |
| ZA (1) | ZA731380B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6495528B1 (en) | 1998-06-23 | 2002-12-17 | Smithkline Beecham Corporation | 2-(Purin -9-yl)-tetrahydrofuran-3,4-diol derivatives |
| US6762170B1 (en) | 1998-01-31 | 2004-07-13 | Smithklinebeecham Corporation | 2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives |
| US7985740B2 (en) | 2005-07-19 | 2011-07-26 | Glaxo Group Limited | Purine derivatives as agonists of the adenosine A2A receptor |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8702926A (en) * | 1986-12-15 | 1988-07-01 | Sandoz Ag | NEW FURANURONIC ACID DERIVATIVES AND METHODS FOR PREPARING AND USING THESE DERIVATIVES. |
| TW528755B (en) | 1996-12-24 | 2003-04-21 | Glaxo Group Ltd | 2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives |
| PE20060272A1 (en) | 2004-05-24 | 2006-05-22 | Glaxo Group Ltd | (2R, 3R, 4S, 5R, 2'R, 3'R, 4'S, 5'S) -2.2 '- {TRANS-1,4-CYCLOHEXANODIYLBIS- [IMINO (2 - {[2- (1-METHYL- 1H-IMIDAZOL-4-IL) ETHYL] AMINO} -9H-PURIN-6,9-DIYL)]} BIS [5- (2-ETHYL-2H-TETRAZOLE-5-IL) TETRAHYDRO-3,4-FURANODIOL] AS AN A2A AGONIST |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2034785A1 (en) * | 1970-07-14 | 1972-01-20 | Boehnnger Mannheim GmbH, 6800 Mann heim Waldhof | Adenosine 5 carboxylic acid derivatives |
-
1973
- 1973-02-26 CA CA164,578A patent/CA1082695A/en not_active Expired
- 1973-02-27 ZA ZA731380A patent/ZA731380B/en unknown
- 1973-03-29 GB GB1521473A patent/GB1399670A/en not_active Expired
- 1973-04-02 JP JP48036829A patent/JPS4913200A/ja active Pending
- 1973-04-09 DE DE2317770A patent/DE2317770A1/en active Pending
- 1973-04-10 CH CH514273A patent/CH565175A5/xx not_active IP Right Cessation
- 1973-04-10 FR FR7312779A patent/FR2179886B1/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6762170B1 (en) | 1998-01-31 | 2004-07-13 | Smithklinebeecham Corporation | 2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives |
| US6495528B1 (en) | 1998-06-23 | 2002-12-17 | Smithkline Beecham Corporation | 2-(Purin -9-yl)-tetrahydrofuran-3,4-diol derivatives |
| US7985740B2 (en) | 2005-07-19 | 2011-07-26 | Glaxo Group Limited | Purine derivatives as agonists of the adenosine A2A receptor |
Also Published As
| Publication number | Publication date |
|---|---|
| CH565175A5 (en) | 1975-08-15 |
| AU5286573A (en) | 1974-09-05 |
| FR2179886A1 (en) | 1973-11-23 |
| ZA731380B (en) | 1973-11-28 |
| DE2317770A1 (en) | 1973-10-18 |
| FR2179886B1 (en) | 1978-04-21 |
| CA1082695A (en) | 1980-07-29 |
| JPS4913200A (en) | 1974-02-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |