GB1588550A - Cytidine derivative - Google Patents
Cytidine derivative Download PDFInfo
- Publication number
- GB1588550A GB1588550A GB24858/78A GB2485878A GB1588550A GB 1588550 A GB1588550 A GB 1588550A GB 24858/78 A GB24858/78 A GB 24858/78A GB 2485878 A GB2485878 A GB 2485878A GB 1588550 A GB1588550 A GB 1588550A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trifluoromethyl
- deoxycytidine
- composition
- f3methyl
- amount
- 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
- 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 title 1
- 239000000203 mixture Substances 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 38
- 230000000840 anti-viral effect Effects 0.000 claims description 36
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical group C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims description 30
- XNSPCSMIPDACTB-RRKCRQDMSA-N 4-amino-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(trifluoromethyl)pyrimidin-2-one Chemical compound C1=C(C(F)(F)F)C(N)=NC(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)C1 XNSPCSMIPDACTB-RRKCRQDMSA-N 0.000 claims description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 22
- 241000700605 Viruses Species 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 22
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- VSQQQLOSPVPRAZ-RRKCRQDMSA-N trifluridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(C(F)(F)F)=C1 VSQQQLOSPVPRAZ-RRKCRQDMSA-N 0.000 claims description 15
- 241000701074 Human alphaherpesvirus 2 Species 0.000 claims description 12
- 229940123974 Cytidine deaminase inhibitor Drugs 0.000 claims description 11
- 229910021529 ammonia Inorganic materials 0.000 claims description 10
- UCKYOOZPSJFJIZ-FMDGEEDCSA-N (4r)-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one Chemical group O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N[C@H](O)CC1 UCKYOOZPSJFJIZ-FMDGEEDCSA-N 0.000 claims description 9
- 241000282414 Homo sapiens Species 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 3
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- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000002207 metabolite Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910000077 silane Inorganic materials 0.000 claims description 3
- UCKYOOZPSJFJIZ-UHFFFAOYSA-N 1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one Chemical compound OC1C(O)C(CO)OC1N1C(=O)NC(O)CC1 UCKYOOZPSJFJIZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000001990 intravenous administration Methods 0.000 claims description 2
- 210000004027 cell Anatomy 0.000 description 41
- 150000001875 compounds Chemical class 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000013456 study Methods 0.000 description 13
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- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 11
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- UHDGCWIWMRVCDJ-XVFCMESISA-N cytidine Chemical class O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-XVFCMESISA-N 0.000 description 5
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- LMNPKIOZMGYQIU-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-pyrimidine-2,4-dione Chemical compound FC(F)(F)C1=CNC(=O)NC1=O LMNPKIOZMGYQIU-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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- WEVJJMPVVFNAHZ-RRKCRQDMSA-N ibacitabine Chemical compound C1=C(I)C(N)=NC(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)C1 WEVJJMPVVFNAHZ-RRKCRQDMSA-N 0.000 description 3
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- MXHRCPNRJAMMIM-SHYZEUOFSA-N 2'-deoxyuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 MXHRCPNRJAMMIM-SHYZEUOFSA-N 0.000 description 2
- KISUPFXQEHWGAR-RRKCRQDMSA-N 4-amino-5-bromo-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound C1=C(Br)C(N)=NC(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)C1 KISUPFXQEHWGAR-RRKCRQDMSA-N 0.000 description 2
- CMZLCHVZCXOMIF-DJLDLDEBSA-N 4-amino-5-ethyl-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C(CC)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 CMZLCHVZCXOMIF-DJLDLDEBSA-N 0.000 description 2
- LUCHPKXVUGJYGU-XLPZGREQSA-N 5-methyl-2'-deoxycytidine Chemical compound O=C1N=C(N)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 LUCHPKXVUGJYGU-XLPZGREQSA-N 0.000 description 2
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- OIRDTQYFTABQOQ-UHTZMRCNSA-N Vidarabine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O OIRDTQYFTABQOQ-UHTZMRCNSA-N 0.000 description 2
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- MXHRCPNRJAMMIM-UHFFFAOYSA-N desoxyuridine Natural products C1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 MXHRCPNRJAMMIM-UHFFFAOYSA-N 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
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- XACKNLSZYYIACO-DJLDLDEBSA-N edoxudine Chemical compound O=C1NC(=O)C(CC)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 XACKNLSZYYIACO-DJLDLDEBSA-N 0.000 description 1
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- 239000000706 filtrate Substances 0.000 description 1
- ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 description 1
- 229960000961 floxuridine Drugs 0.000 description 1
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- 239000007927 intramuscular injection Substances 0.000 description 1
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- 210000003734 kidney Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 201000005264 laryngeal carcinoma Diseases 0.000 description 1
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- 231100001231 less toxic Toxicity 0.000 description 1
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- 239000012263 liquid product Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
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- 150000004712 monophosphates Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 231100000065 noncytotoxic Toxicity 0.000 description 1
- 230000002020 noncytotoxic effect Effects 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
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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
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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88755578A | 1978-03-17 | 1978-03-17 | |
| US88774578A | 1978-03-17 | 1978-03-17 | |
| US05/887,541 US4210638A (en) | 1978-03-17 | 1978-03-17 | Antiviral composition and method of treating virus diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1588550A true GB1588550A (en) | 1981-04-23 |
Family
ID=27420527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24858/78A Expired GB1588550A (en) | 1978-03-17 | 1978-05-31 | Cytidine derivative |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE2838644A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1588550A (enrdf_load_stackoverflow) |
| IT (1) | IT1094895B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5008252A (en) * | 1987-03-20 | 1991-04-16 | The University Of North Carolina At Chapel Hill | Process for inhibiting herpes simplex virus-specified thymidine kinase |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4017606A (en) * | 1973-10-04 | 1977-04-12 | The Upjohn Company | Organic compounds and process |
-
1978
- 1978-05-30 IT IT23988/78A patent/IT1094895B/it active
- 1978-05-31 GB GB24858/78A patent/GB1588550A/en not_active Expired
- 1978-09-05 DE DE19782838644 patent/DE2838644A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT1094895B (it) | 1985-08-10 |
| DE2838644C2 (enrdf_load_stackoverflow) | 1989-02-02 |
| IT7823988A0 (it) | 1978-05-30 |
| DE2838644A1 (de) | 1979-09-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |