CH592685A5 - 3'-Fluro-pyrimidine nucleosides prepn - by demesylation of 5'-O-mesyl derivs - Google Patents

3'-Fluro-pyrimidine nucleosides prepn - by demesylation of 5'-O-mesyl derivs

Info

Publication number: CH592685A5
Authority: CH; Switzerland
Prior art keywords: formula; compound; mesyl; treated; general formula
Prior art date: 1972-12-12

Application number

CH1736973A

Other languages

German (de)

English (en)

Original Assignee

Akad Wissenschaften Ddr

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.)

1972-12-12

Filing date

1973-12-12

Publication date

1977-11-15

1973-12-12 Application filed by Akad Wissenschaften Ddr filed Critical Akad Wissenschaften Ddr

1977-11-15 Publication of CH592685A5 publication Critical patent/CH592685A5/de

Links

239000002718 pyrimidine nucleoside Substances 0.000 title description 5
239000002777 nucleoside Substances 0.000 claims abstract description 7
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 claims description 6
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 4
-1 alkali metal salt Chemical class 0.000 claims description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 3
235000011056 potassium acetate Nutrition 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
239000012345 acetylating agent Substances 0.000 claims description 2
150000003855 acyl compounds Chemical class 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
238000002955 isolation Methods 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
238000010992 reflux Methods 0.000 claims description 2
239000011833 salt mixture Substances 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
UXCAQJAQSWSNPQ-XLPZGREQSA-N Alovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](F)C1 UXCAQJAQSWSNPQ-XLPZGREQSA-N 0.000 abstract description 4
238000000926 separation method Methods 0.000 abstract description 3
230000006820 DNA synthesis Effects 0.000 abstract description 2
229940124639 Selective inhibitor Drugs 0.000 abstract description 2
150000003839 salts Chemical class 0.000 abstract description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
125000000217 alkyl group Chemical group 0.000 abstract 2
125000003835 nucleoside group Chemical group 0.000 abstract 2
229910021529 ammonia Inorganic materials 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
238000000746 purification Methods 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
KIEUYYVPJIIRHO-DJLDLDEBSA-N [(2r,3s,5r)-3-fluoro-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl methanesulfonate Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COS(C)(=O)=O)[C@@H](F)C1 KIEUYYVPJIIRHO-DJLDLDEBSA-N 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000007858 starting material Substances 0.000 description 3
229940104230 thymidine Drugs 0.000 description 3
229940113082 thymine Drugs 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 2
DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000006196 deacetylation Effects 0.000 description 2
238000003381 deacetylation reaction Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
BKIUEHLYJFLWPK-SHYZEUOFSA-N 1-[(2r,4s,5r)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound C1[C@H](F)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 BKIUEHLYJFLWPK-SHYZEUOFSA-N 0.000 description 1
IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 description 1
LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
101100004392 Arabidopsis thaliana BHLH147 gene Proteins 0.000 description 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
230000020176 deacylation Effects 0.000 description 1
238000005947 deacylation reaction Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229940035893 uracil Drugs 0.000 description 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

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)

CH1736973A 1972-12-12 1973-12-12 3'-Fluro-pyrimidine nucleosides prepn - by demesylation of 5'-O-mesyl derivs CH592685A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD16765772A DD103241A1 (fi)	1972-12-12	1972-12-12

Publications (1)

Publication Number	Publication Date
CH592685A5 true CH592685A5 (en)	1977-11-15

Family

ID=5489391

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1736973A CH592685A5 (en)	1972-12-12	1973-12-12	3'-Fluro-pyrimidine nucleosides prepn - by demesylation of 5'-O-mesyl derivs

Country Status (5)

Country	Link
CH (1)	CH592685A5 (fi)
CS (1)	CS179035B1 (fi)
DD (1)	DD103241A1 (fi)
HU (1)	HU168712B (fi)
SU (1)	SU666184A1 (fi)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8719877D0 (en) *	1987-08-22	1987-09-30	Wellcome Found	Antiviral compounds
IL100480A0 (en) *	1991-01-15	1992-09-06	American Cyanamid Co	Process for the preparation of 3'-fluoropyrimidine nucleosides

1972
- 1972-12-12 DD DD16765772A patent/DD103241A1/xx unknown
1973
- 1973-12-07 HU HUWI000247 patent/HU168712B/hu not_active IP Right Cessation
- 1973-12-11 CS CS856673A patent/CS179035B1/cs unknown
- 1973-12-11 SU SU731977925A patent/SU666184A1/ru active
- 1973-12-12 CH CH1736973A patent/CH592685A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
HU168712B (fi)	1976-06-28
CS179035B1 (en)	1977-10-31
SU666184A1 (ru)	1979-06-05
DD103241A1 (fi)	1974-01-12

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Legal Events

Date	Code	Title	Description
1990-08-31	PL	Patent ceased
2024-10-31	PL	Patent ceased