GB1386334A - 2,2-cyclocytidine derivatives - Google Patents
2,2-cyclocytidine derivativesInfo
- Publication number
- GB1386334A GB1386334A GB4393872A GB4393872A GB1386334A GB 1386334 A GB1386334 A GB 1386334A GB 4393872 A GB4393872 A GB 4393872A GB 4393872 A GB4393872 A GB 4393872A GB 1386334 A GB1386334 A GB 1386334A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- hydrogen atom
- atom
- general formula
- hydrogen
- 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 16
- 150000001875 compounds Chemical class 0.000 abstract 3
- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical class O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 229940005657 pyrophosphoric acid Drugs 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- YOCCKNBIYQRJDP-VPCXQMTMSA-N 4-amino-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-methoxyoxolan-2-yl]pyrimidin-2-one Chemical compound C1=CC(N)=NC(=O)N1[C@]1(OC)O[C@H](CO)[C@@H](O)[C@H]1O YOCCKNBIYQRJDP-VPCXQMTMSA-N 0.000 abstract 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical group Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 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
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000001093 anti-cancer Effects 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 230000000840 anti-viral effect Effects 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- C07H19/06—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
- C07H19/06—Pyrimidine radicals
- C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1386334 2,2<SP>1</SP>-Cyclocytidine derivatives KOHJIN KK 22 Sept 1972 43938/72 Headings C2C and C2P Novel 2,2<SP>1</SP>-cyclocytidine derivatives of the general formula wherein R 1 is a hydrogen atom or a Z-CO- or -H 2 PO 3 group, Z is a C 1-4 alkyl or phenyl group, R 2 is a hydrogen atom or -H 2 PO 3 , Y is a hydrogen atom or a hydroxy, C 1-4 alkyl or C 1-4 alkoxy group and X is a hydrogen or halogen atom or a methyl group, except that (a) X, Y, R 1 and R 2 are not simultaneously hydrogen atoms, (b) X, Y and R 1 are not simultaneously hydrogen atoms if R 2 is a -H 2 PO 3 group, (c) X and Y are not both hydrogen atoms if R 1 and R 2 are both -H 2 PO 3 groups and (d) X, Y and R 2 are not simultaneously hydrogen atoms if R 1 is Z-CO-, and pharmaceutically acceptable acid addition and intramolecular salts thereof are prepared (a) when R 1 is a hydrogen atom or -H 2 PO 3 group and R 2 is a hydrogen atom, by heating the corresponding cytidine derivative of the general formula wherein R 3 is a hydrogen atom or -H 2 PO 3 group, except that X, Y and R 3 are not simultaneously hydrogen atoms, with a compound formed by substituting a chlorine atom for one or more hydroxy groups in phosphoric or pyrophosphoric acid or an ester thereof, in the presence of an ester of a carboxylic acid; (b) when R 1 is an -HPO 3 <SP>(-)</SP> group, R 2 is an -H 2 PO 3 group, X is a halogen atom or methyl group, and Y is -H 2 <SP>(+)</SP>, by heating the corresponding cytidine of the second general formula above, wherein each of R 3 and Y is a hydrogen atom, with a compound formed by substituting a chlorine atom for one or more hydroxy groups in phosphoric or pyrophosphoric acid or an ester thereof; and (c) when R 1 is an acetyl group, R 2 is a hydrogen atom, and X and Y are not both hydrogen atoms, by reacting the corresponding compound of the first general formula above wherein R 1 is a hydrogen atom with glacial acetic acid. N<SP>4</SP>-Hydroxy- or methoxy-cytidine is prepared by reacting cytidine with hydroxyl- or methoxyamine hydrochloride, respectively. Pharmaceutical compositions having antiviral, antitumour and anticancer activity comprise, as active ingredient, a 2,2<SP>1</SP>-cyclocytidine derivative of the first general formula above, together with a pharmaceutical carrier or diluent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4393872A GB1386334A (en) | 1972-09-22 | 1972-09-22 | 2,2-cyclocytidine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4393872A GB1386334A (en) | 1972-09-22 | 1972-09-22 | 2,2-cyclocytidine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1386334A true GB1386334A (en) | 1975-03-05 |
Family
ID=10431026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4393872A Expired GB1386334A (en) | 1972-09-22 | 1972-09-22 | 2,2-cyclocytidine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1386334A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11331331B2 (en) | 2017-12-07 | 2022-05-17 | Emory University | N4-hydroxycytidine and derivatives and anti-viral uses related thereto |
| US11628181B2 (en) | 2014-12-26 | 2023-04-18 | Emory University | N4-hydroxycytidine and derivatives and anti-viral uses related thereto |
-
1972
- 1972-09-22 GB GB4393872A patent/GB1386334A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11628181B2 (en) | 2014-12-26 | 2023-04-18 | Emory University | N4-hydroxycytidine and derivatives and anti-viral uses related thereto |
| US11331331B2 (en) | 2017-12-07 | 2022-05-17 | Emory University | N4-hydroxycytidine and derivatives and anti-viral uses related thereto |
| US11903959B2 (en) | 2017-12-07 | 2024-02-20 | Emory University | N4-hydroxycytidine and derivatives and anti-viral uses related thereto |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |