GB1319303A - Sugar derivatives - Google Patents
Sugar derivativesInfo
- Publication number
- GB1319303A GB1319303A GB1319303DA GB1319303A GB 1319303 A GB1319303 A GB 1319303A GB 1319303D A GB1319303D A GB 1319303DA GB 1319303 A GB1319303 A GB 1319303A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- cyano
- isopropylidene
- cyanouracil
- ribofuranosyl
- 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
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- BWNHYYJPSYWLQK-DDIGBBAMSA-N 6-[(2R,3S,4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]-2,4-dioxo-1H-pyrimidine-5-carbonitrile Chemical compound [C@H]1([C@@H](O)[C@@H](O)[C@H](O1)[C@H](O)CO)C1=C(C(NC(N1)=O)=O)C#N BWNHYYJPSYWLQK-DDIGBBAMSA-N 0.000 abstract 1
- 229930010555 Inosine Natural products 0.000 abstract 1
- UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002243 furanoses Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000002460 imidazoles Chemical class 0.000 abstract 1
- 230000001861 immunosuppressant effect Effects 0.000 abstract 1
- 229960003786 inosine Drugs 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- -1 methyl 5 - amino - 1 Chemical compound 0.000 abstract 1
- 239000002777 nucleoside Substances 0.000 abstract 1
- 125000003835 nucleoside group Chemical group 0.000 abstract 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002212 purine nucleoside Substances 0.000 abstract 1
- 239000002718 pyrimidine nucleoside Substances 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical group CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
- C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
- C07H9/04—Cyclic acetals
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
1319303 Mono- and di-alkylidenefuranosylamines UNIVERSITY OF BRADFORD 14 July 1971 [14 July 1970 3 Nov 1970] 34176/70 and 52219/70 Heading C2C Novel acid addition salts of mono- and dialkylidenefuranosylamines are prepared by reacting a pyranosylamine of Formula I (in which R 1 is H, CH 3 or CH 2 OH, R 2 is H, NH 2 or OH, R 3 is H or CH 2 OH and R 4 and R 5 are H, C 1-6 alkyl or aryl) and which is such that, in the furanose form, it possesses at least one pair of 1,2-cis or 1,3-cis hydroxyls, with a carbonyl compound of formula (in which each of R 6 and R 7 is H, C 1-6 alkyl or aryl or R 6 and R 7 , together with the carbonyl group, form an alicylic ketone, in the presence of sufficient strong acid, e.g. an acid of the formula HX (where X is halogen, sulphate or p-toluenesulphonate), to ensure that the amino group remains protonated. Examples of compounds which can be prepared by the above method have the formulae The novel acid addition salts are useful in the preparation of known nucleosides such as imidazole, pyrimidine and purine nucleosides which have antibiotic, antitumour and immunosuppressant activity. In examples, 3-(2<SP>1</SP>,3<SP>1</SP>-oisopropylidene - # - D - ribofuranosyl) - 5 - cyanouracil, 3 - (# - D - ribofuranosyl) - 5 - cyanouracil, di - isopropylidene - mannofuranosylcyanouracil, α - D - mannofuranosyl - 5 - cyanouracil, methyl 5 - amino - 1 - (2<SP>1</SP>3<SP>1</SP> - O - isopropylidene- # - D- ribofuranosyl)imidazole - 4 - carboxylate, inosine, 5 - cyano - 3 - methyl - 1 - (31,51 - O - isopropyldiene - # - D - xylofuranosyl) - uracil, 5 - cyano- 3 - methyl - 1 - # - D - xylofuranosyluracil, 2,3- O - isopropylidene - 5 - cyano - 3 - methyl - 1 - α- L - rhamnofuranosyluracil, 5 - cyano - 3 - methyl- 1 - α - L - rhamnofuranosyluracil, 5,6 - O - isopropylidene - 5 - cyano - 3 - methyl - 1 - # - D- glucofuranosyluracil, 5 - cyano - 3 - methyl - 1- # - D - glucofuranosyluracil and N - hippuroyl- 2,3 - O - isopropylidene - # - D - ribofuranosylamine are prepared.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3417670 | 1970-07-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1319303A true GB1319303A (en) | 1973-06-06 |
Family
ID=10362335
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1319303D Expired GB1319303A (en) | 1970-07-14 | 1970-07-14 | Sugar derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1319303A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8871737B2 (en) | 2010-09-22 | 2014-10-28 | Alios Biopharma, Inc. | Substituted nucleotide analogs |
| US8916538B2 (en) | 2012-03-21 | 2014-12-23 | Vertex Pharmaceuticals Incorporated | Solid forms of a thiophosphoramidate nucleotide prodrug |
| US8980865B2 (en) | 2011-12-22 | 2015-03-17 | Alios Biopharma, Inc. | Substituted nucleotide analogs |
| US9012427B2 (en) | 2012-03-22 | 2015-04-21 | Alios Biopharma, Inc. | Pharmaceutical combinations comprising a thionucleotide analog |
-
1970
- 1970-07-14 GB GB1319303D patent/GB1319303A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8871737B2 (en) | 2010-09-22 | 2014-10-28 | Alios Biopharma, Inc. | Substituted nucleotide analogs |
| US9278990B2 (en) | 2010-09-22 | 2016-03-08 | Alios Biopharma, Inc. | Substituted nucleotide analogs |
| US8980865B2 (en) | 2011-12-22 | 2015-03-17 | Alios Biopharma, Inc. | Substituted nucleotide analogs |
| US9605018B2 (en) | 2011-12-22 | 2017-03-28 | Alios Biopharma, Inc. | Substituted nucleotide analogs |
| US8916538B2 (en) | 2012-03-21 | 2014-12-23 | Vertex Pharmaceuticals Incorporated | Solid forms of a thiophosphoramidate nucleotide prodrug |
| US9394330B2 (en) | 2012-03-21 | 2016-07-19 | Alios Biopharma, Inc. | Solid forms of a thiophosphoramidate nucleotide prodrug |
| US9856284B2 (en) | 2012-03-21 | 2018-01-02 | Alios Biopharma, Inc. | Solid forms of a thiophosphoramidate nucleotide prodrug |
| US9012427B2 (en) | 2012-03-22 | 2015-04-21 | Alios Biopharma, Inc. | Pharmaceutical combinations comprising a thionucleotide analog |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |