DD147774A3 - Verfahren zur herstellung von 2'-halogen-2'-desoxy-5-fluoruridinen und ihren 3',5'-di-o-benzoylderivaten - Google Patents

Verfahren zur herstellung von 2'-halogen-2'-desoxy-5-fluoruridinen und ihren 3',5'-di-o-benzoylderivaten Download PDF

Info

Publication number: DD147774A3
Authority: DD; German Democratic Republic
Prior art keywords: deoxy; preparation; acetic acid; halo; general formula
Prior art date: 1976-02-19

Application number

DD19139576A

Other languages

German (de)

English (en)

Inventor

Dieter Cech

Antonin Holy

Original Assignee

Dieter Cech

Antonin Holy

Priority date (The priority date 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 date listed.)

1976-02-19

Filing date

1976-02-20

Publication date

1981-04-22

1976-02-20 Application filed by Dieter Cech, Antonin Holy filed Critical Dieter Cech

1981-04-22 Publication of DD147774A3 publication Critical patent/DD147774A3/de

Links

238000000034 method Methods 0.000 title claims abstract description 14
238000002360 preparation method Methods 0.000 title claims abstract description 9
230000008569 process Effects 0.000 title claims abstract description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 45
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 14
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
239000011737 fluorine Substances 0.000 claims abstract description 9
229910052794 bromium Inorganic materials 0.000 claims abstract description 5
229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
238000009835 boiling Methods 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
239000002777 nucleoside Substances 0.000 abstract description 7
125000003835 nucleoside group Chemical group 0.000 abstract description 4
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 abstract description 3
230000003385 bacteriostatic effect Effects 0.000 abstract description 2
230000003327 cancerostatic effect Effects 0.000 abstract description 2
150000003230 pyrimidines Chemical class 0.000 abstract description 2
230000001790 virustatic effect Effects 0.000 abstract description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
238000004519 manufacturing process Methods 0.000 description 7
239000000243 solution Substances 0.000 description 7
150000001875 compounds Chemical class 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000002342 ribonucleoside Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
230000009471 action Effects 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
239000005549 deoxyribonucleoside Substances 0.000 description 3
238000003682 fluorination reaction Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000012047 saturated solution Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
-1 5-fluoro-substituted pyrimidine Chemical class 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
MXHRCPNRJAMMIM-UHFFFAOYSA-N desoxyuridine Natural products C1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 MXHRCPNRJAMMIM-UHFFFAOYSA-N 0.000 description 2
150000007523 nucleic acids Chemical class 0.000 description 2
102000039446 nucleic acids Human genes 0.000 description 2
108020004707 nucleic acids Proteins 0.000 description 2
150000003833 nucleoside derivatives Chemical class 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 2
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 1
125000003504 2-oxazolinyl group Chemical class O1C(=NCC1)* 0.000 description 1
FHIDNBAQOFJWCA-UAKXSSHOSA-N 5-fluorouridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 FHIDNBAQOFJWCA-UAKXSSHOSA-N 0.000 description 1
NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
QSWJDRDXNLNCJA-IPMKNSEASA-N [(2r,3s,5r)-3-benzoyloxy-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1O[C@H](COC(=O)C=2C=CC=CC=2)[C@@H](OC(=O)C=2C=CC=CC=2)C1 QSWJDRDXNLNCJA-IPMKNSEASA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
UMDFLFHAXYPYQN-UKTARXLSSA-N anhydro nucleoside Chemical compound C([C@H]1O[C@H]2N3C=C(C(N=C3O[C@@H]1[C@@H]2F)=O)C)OC(=O)C1=CC=CC=C1 UMDFLFHAXYPYQN-UKTARXLSSA-N 0.000 description 1
230000000340 anti-metabolite Effects 0.000 description 1
229940100197 antimetabolite Drugs 0.000 description 1
239000002256 antimetabolite Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000007360 debenzoylation reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
150000002221 fluorine Chemical class 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
238000006140 methanolysis reaction Methods 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002718 pyrimidine nucleoside Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
238000006257 total synthesis reaction Methods 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical compound FOC(F)(F)F SMBZJSVIKJMSFP-UHFFFAOYSA-N 0.000 description 1
229940035893 uracil Drugs 0.000 description 1

Landscapes

Saccharide Compounds (AREA)

DD19139576A 1976-02-19 1976-02-20 Verfahren zur herstellung von 2'-halogen-2'-desoxy-5-fluoruridinen und ihren 3',5'-di-o-benzoylderivaten DD147774A3 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CS105476A CS184526B1 (en)	1976-02-19	1976-02-19	2'-halogen-2'-deoxy-5-fluoruridine,3',5-di-o-benzoyl-derivatives and process for preparing thereof

Publications (1)

Publication Number	Publication Date
DD147774A3 true DD147774A3 (de)	1981-04-22

Family

ID=5343925

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD19139576A DD147774A3 (de)	1976-02-19	1976-02-20	Verfahren zur herstellung von 2'-halogen-2'-desoxy-5-fluoruridinen und ihren 3',5'-di-o-benzoylderivaten

Country Status (2)

Country	Link
CS (1)	CS184526B1 (cs)
DD (1)	DD147774A3 (cs)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1985001871A1 (en) *	1983-10-26	1985-05-09	Greer Sheldon B	Method and materials for sensitizing neoplastic tissue to radiation
US4847366A (en) *	1986-08-05	1989-07-11	Daikin Industries Ltd.	5-fluorouridine derivative and preparation of the same

1976
- 1976-02-19 CS CS105476A patent/CS184526B1/cs unknown
- 1976-02-20 DD DD19139576A patent/DD147774A3/de unknown

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1985001871A1 (en) *	1983-10-26	1985-05-09	Greer Sheldon B	Method and materials for sensitizing neoplastic tissue to radiation
US4847366A (en) *	1986-08-05	1989-07-11	Daikin Industries Ltd.	5-fluorouridine derivative and preparation of the same

Also Published As

Publication number	Publication date
CS184526B1 (en)	1978-08-31

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