GB1428986A - Acyl derivatives of o2,2-anhydro1-beta-d-arabinofuranosyl- cytosines and azacytosines and methods for their preparation - Google Patents
Acyl derivatives of o2,2-anhydro1-beta-d-arabinofuranosyl- cytosines and azacytosines and methods for their preparationInfo
- Publication number
- GB1428986A GB1428986A GB1016873A GB1016873A GB1428986A GB 1428986 A GB1428986 A GB 1428986A GB 1016873 A GB1016873 A GB 1016873A GB 1016873 A GB1016873 A GB 1016873A GB 1428986 A GB1428986 A GB 1428986A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acyl
- hydrogen
- compounds
- arylalkyl
- arabinofuranosyl
- 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
- 125000002252 acyl group Chemical group 0.000 title abstract 11
- 239000001257 hydrogen Substances 0.000 abstract 9
- 229910052739 hydrogen Inorganic materials 0.000 abstract 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- -1 p-nitrophenylacetyl Chemical group 0.000 abstract 3
- 229940126062 Compound A Drugs 0.000 abstract 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 abstract 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 150000001263 acyl chlorides Chemical class 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 230000000840 anti-viral effect Effects 0.000 abstract 1
- 125000001124 arachidoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000003910 behenoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000003312 cerotoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229940104302 cytosine Drugs 0.000 abstract 1
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Natural products NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 abstract 1
- 230000001472 cytotoxic effect Effects 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- BWHLPLXXIDYSNW-UHFFFAOYSA-N ketorolac tromethamine Chemical compound OCC(N)(CO)CO.OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 BWHLPLXXIDYSNW-UHFFFAOYSA-N 0.000 abstract 1
- 125000000403 lignoceroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000002777 nucleoside Substances 0.000 abstract 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 abstract 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- C07H19/06—Pyrimidine radicals
-
- 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
- C07H19/12—Triazine 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23175372A | 1972-03-03 | 1972-03-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1428986A true GB1428986A (en) | 1976-03-24 |
Family
ID=22870520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1016873A Expired GB1428986A (en) | 1972-03-03 | 1973-03-02 | Acyl derivatives of o2,2-anhydro1-beta-d-arabinofuranosyl- cytosines and azacytosines and methods for their preparation |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS49132084A (enrdf_load_stackoverflow) |
| AU (1) | AU473605B2 (enrdf_load_stackoverflow) |
| CH (1) | CH595393A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2310285A1 (enrdf_load_stackoverflow) |
| ES (1) | ES412269A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2181782B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1428986A (enrdf_load_stackoverflow) |
| NL (1) | NL7303003A (enrdf_load_stackoverflow) |
| SE (1) | SE399559B (enrdf_load_stackoverflow) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3709874A (en) * | 1970-03-19 | 1973-01-09 | Syntex Corp | 1-beta-d-arabinofuranosyl cytosine derivatives and methods of preparing |
| GB1322136A (en) * | 1971-01-27 | 1973-07-04 | Upjohn Co | Ara-cytidine derivatives |
-
1973
- 1973-03-01 SE SE7302912A patent/SE399559B/xx unknown
- 1973-03-01 DE DE19732310285 patent/DE2310285A1/de active Pending
- 1973-03-01 AU AU52745/73A patent/AU473605B2/en not_active Expired
- 1973-03-01 FR FR7307382A patent/FR2181782B1/fr not_active Expired
- 1973-03-02 NL NL7303003A patent/NL7303003A/xx not_active Application Discontinuation
- 1973-03-02 GB GB1016873A patent/GB1428986A/en not_active Expired
- 1973-03-02 JP JP2501773A patent/JPS49132084A/ja active Pending
- 1973-03-02 CH CH311073A patent/CH595393A5/xx not_active IP Right Cessation
- 1973-03-02 ES ES412269A patent/ES412269A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH595393A5 (enrdf_load_stackoverflow) | 1978-02-15 |
| AU473605B2 (en) | 1976-06-24 |
| FR2181782A1 (enrdf_load_stackoverflow) | 1973-12-07 |
| NL7303003A (enrdf_load_stackoverflow) | 1973-09-06 |
| FR2181782B1 (enrdf_load_stackoverflow) | 1976-10-22 |
| JPS49132084A (enrdf_load_stackoverflow) | 1974-12-18 |
| AU5274573A (en) | 1974-09-05 |
| ES412269A1 (es) | 1977-01-01 |
| DE2310285A1 (de) | 1973-09-20 |
| SE399559B (sv) | 1978-02-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |