DD275874A5 - Verfahren zur herstellung von 2',3'-dideoxy-2'-fluoronucleosiden - Google Patents

Verfahren zur herstellung von 2',3'-dideoxy-2'-fluoronucleosiden Download PDF

Info

Publication number: DD275874A5
Authority: DD; German Democratic Republic
Prior art keywords: group; hydroxy; deoxy; compound; compounds
Prior art date: 1987-11-12

Application number

DD88321728A

Other languages

German (de)

English (en)

Inventor

Roman Z Sterzycki

Muzammil M Mansuri

John C Martin

Original Assignee

��`��@��k��

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.)

1987-11-12

Filing date

1988-11-11

Publication date

1990-02-07

1988-11-11 Application filed by ��`��@��k�� filed Critical ��`��@��k��

1990-02-07 Publication of DD275874A5 publication Critical patent/DD275874A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 19
238000002360 preparation method Methods 0.000 title claims abstract description 16
150000001875 compounds Chemical class 0.000 claims abstract description 53
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 20
-1 deazapurine Chemical compound 0.000 claims description 18
125000006239 protecting group Chemical group 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 13
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 12
229910052731 fluorine Inorganic materials 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 8
230000015572 biosynthetic process Effects 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 8
239000003153 chemical reaction reagent Substances 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 5
230000008030 elimination Effects 0.000 claims description 5
238000003379 elimination reaction Methods 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
XZLIYCQRASOFQM-UHFFFAOYSA-N 5h-imidazo[4,5-d]triazine Chemical compound N1=NC=C2NC=NC2=N1 XZLIYCQRASOFQM-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
229940104302 cytosine Drugs 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 4
229940035893 uracil Drugs 0.000 claims description 4
229930024421 Adenine Natural products 0.000 claims description 3
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 3
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
229960000643 adenine Drugs 0.000 claims description 3
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
150000003462 sulfoxides Chemical class 0.000 claims description 3
125000003944 tolyl group Chemical group 0.000 claims description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
239000012038 nucleophile Substances 0.000 claims description 2
238000003431 reductive deoxygenation reaction Methods 0.000 claims description 2
230000002829 reductive effect Effects 0.000 claims description 2
229940113082 thymine Drugs 0.000 claims description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
125000001425 triazolyl group Chemical group 0.000 claims 1
239000003443 antiviral agent Substances 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 41
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
235000019439 ethyl acetate Nutrition 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
239000000543 intermediate Substances 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
239000003039 volatile agent Substances 0.000 description 12
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
239000000203 mixture Substances 0.000 description 9
239000000047 product Substances 0.000 description 9
239000000126 substance Substances 0.000 description 9
241000725303 Human immunodeficiency virus Species 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
125000005843 halogen group Chemical group 0.000 description 7
229940045145 uridine Drugs 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000012043 crude product Substances 0.000 description 6
238000006722 reduction reaction Methods 0.000 description 6
239000007858 starting material Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 4
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
230000000840 anti-viral effect Effects 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
235000011089 carbon dioxide Nutrition 0.000 description 3
JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000006228 supernatant Substances 0.000 description 3
229940104230 thymidine Drugs 0.000 description 3
150000003852 triazoles Chemical group 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
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 2
DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
230000036436 anti-hiv Effects 0.000 description 2
239000012300 argon atmosphere Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
230000000120 cytopathologic effect Effects 0.000 description 2
JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
229920001843 polymethylhydrosiloxane Polymers 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000002718 pyrimidine nucleoside Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
125000003396 thiol group Chemical group [H]S* 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
LOSXTWDYAWERDB-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-2,3-dimethoxybenzene Chemical compound COC1=CC=CC(C(Cl)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1OC LOSXTWDYAWERDB-UHFFFAOYSA-N 0.000 description 1
VWCUMTCXBIRRSG-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-2-methoxybenzene Chemical compound COC1=CC=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 VWCUMTCXBIRRSG-UHFFFAOYSA-N 0.000 description 1
KXCHLAARWGPSAG-YLWLKBPMSA-N 4-amino-1-[(2r,5s)-3-fluoro-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)=C[C@@H](CO)O1 KXCHLAARWGPSAG-YLWLKBPMSA-N 0.000 description 1
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
ZKBQDFAWXLTYKS-UHFFFAOYSA-N 6-Chloro-1H-purine Chemical compound ClC1=NC=NC2=C1NC=N2 ZKBQDFAWXLTYKS-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
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 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
208000031886 HIV Infections Diseases 0.000 description 1
241000282412 Homo Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
108091034117 Oligonucleotide Proteins 0.000 description 1
KBEMFSMODRNJHE-BAJZRUMYSA-N [(2s,4r,5r)-5-(6-aminopurin-9-yl)-4-fluorooxolan-2-yl]methanol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)C[C@H]1F KBEMFSMODRNJHE-BAJZRUMYSA-N 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
238000005576 amination reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
238000005915 ammonolysis reaction Methods 0.000 description 1
239000002259 anti human immunodeficiency virus agent Substances 0.000 description 1
229940124411 anti-hiv antiviral agent Drugs 0.000 description 1
230000001399 anti-metabolic effect Effects 0.000 description 1
230000000118 anti-neoplastic effect Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
238000003556 assay Methods 0.000 description 1
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 1
DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 description 1
238000004166 bioassay Methods 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
229940125890 compound Ia Drugs 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000005695 dehalogenation reaction Methods 0.000 description 1
210000003298 dental enamel Anatomy 0.000 description 1
238000006392 deoxygenation reaction Methods 0.000 description 1
RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 1
229960005215 dichloroacetic acid Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
150000002148 esters Chemical group 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229960004279 formaldehyde Drugs 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000002372 labelling Methods 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
235000019988 mead Nutrition 0.000 description 1
238000003328 mesylation reaction Methods 0.000 description 1
239000002777 nucleoside Substances 0.000 description 1
150000003833 nucleoside derivatives Chemical class 0.000 description 1
KOSYAAIZOGNATQ-UHFFFAOYSA-N o-phenyl chloromethanethioate Chemical compound ClC(=S)OC1=CC=CC=C1 KOSYAAIZOGNATQ-UHFFFAOYSA-N 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
230000001350 orogenic effect Effects 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002212 purine nucleoside Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000007788 roughening Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003451 thiazide diuretic agent Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
238000001665 trituration Methods 0.000 description 1
DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 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
- C07H19/16—Purine 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- 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
- 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
- C07H19/16—Purine radicals
- C07H19/173—Purine radicals with 2-deoxyribosyl as the saccharide radical
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Virology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD88321728A 1987-11-12 1988-11-11 Verfahren zur herstellung von 2',3'-dideoxy-2'-fluoronucleosiden DD275874A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/120,051 US4908440A (en)	1987-11-12	1987-11-12	2',3'-dideoxy-2'-fluoroarabinopyrimidine nucleosides

Publications (1)

Publication Number	Publication Date
DD275874A5 true DD275874A5 (de)	1990-02-07

Family

ID=22387985

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88321728A DD275874A5 (de)	1987-11-12	1988-11-11	Verfahren zur herstellung von 2',3'-dideoxy-2'-fluoronucleosiden

Country Status (22)

Country	Link
US (4)	US4908440A (cs)
EP (1)	EP0316017B1 (cs)
JP (4)	JPH01153698A (cs)
KR (1)	KR920004459B1 (cs)
AT (1)	ATE100461T1 (cs)
AU (1)	AU615960B2 (cs)
CA (1)	CA1340961C (cs)
CZ (3)	CZ278366B6 (cs)
DD (1)	DD275874A5 (cs)
DE (1)	DE3887273T2 (cs)
DK (1)	DK173971B1 (cs)
ES (1)	ES2061609T3 (cs)
FI (1)	FI90244C (cs)
HU (1)	HU199499B (cs)
IE (1)	IE62227B1 (cs)
IL (1)	IL88330A (cs)
NO (1)	NO169492C (cs)
NZ (1)	NZ226845A (cs)
PT (1)	PT88994B (cs)
SK (2)	SK743188A3 (cs)
YU (1)	YU47121B (cs)
ZA (1)	ZA888313B (cs)

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US5175292A (en) *	1988-01-20	1992-12-29	Regents Of The University Of Minnesota	Intermediates for the preparation of dideoxycarbocyclic nucleosides
US5631370A (en)	1988-01-20	1997-05-20	Regents Of The University Of Minnesota	Optically-active isomers of dideoxycarbocyclic nucleosides
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US5198539A (en) *	1988-08-19	1993-03-30	Burroughs Wellcome Co.	5'-esters of 2',3'-dideoxy-3'-fluoro-5-ethynyluridine
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FI95384C (fi) *	1989-04-06	1996-01-25	Squibb Bristol Myers Co	Menetelmä 3'-deoksi-3'-substituoitujen metyylinukleosidien valmistamiseksi ja menetelmässä käytettäviä välituotteita
SE464168B (sv) *	1989-07-19	1991-03-18	Bo Fredrik Oeberg	Antiviral komposition bestaaende av en 3'-fluoro-2',3'-dideoxynukleosidfoerening och en 2',3'-dideoxynukleosidfoerening (exempelvis azt)
ES2253732T3 (es) *	1989-09-15	2006-06-01	Southern Research Institute	2'-deoxi-4'-tioribonucleosidos como agentes antivirales y anticancerosos.
US5817799A (en) *	1990-07-23	1998-10-06	The United States Of America As Represented By The Department Of Health And Human Services	2'-Fluorofuranosyl derivatives and methods for preparing 2'-fluoropyrimidine and 2'-fluoropurine nucleosides
US5420115A (en) *	1990-09-10	1995-05-30	Burroughs Wellcome Co.	Method for the treatment of protoza infections with 21 -deoxy-21 -fluoropurine nucleosides
WO1992011276A1 (en) *	1990-12-18	1992-07-09	Sloan-Kettering Institute For Cancer Research	Novel synthesis of 2'-'up' fluorinated 2''-deoxy-arabinofuranosylpurines
ZA923641B (en) *	1991-05-21	1993-02-24	Iaf Biochem Int	Processes for the diastereoselective synthesis of nucleosides
US5712477A (en) *	1996-05-14	1998-01-27	Allen-Bradley Company, Inc.	System to provide alignment and troubleshooting aid photoelectric sensors through alternating numeric display
EA200700564A1 (ru)	1998-02-25	2007-08-31	Эмори Юниверсити	2`-фторнуклеозиды
CN101240001B (zh) *	1998-02-25	2013-10-16	埃莫里大学	2'-氟代核苷
KR20090089922A (ko)	2000-10-18	2009-08-24	파마셋 인코포레이티드	바이러스 감염 및 비정상적인 세포 증식의 치료를 위한 변형된 뉴클레오시드
WO2003000200A2 (en)	2001-06-22	2003-01-03	Pharmasset Ltd.	β-2'-OR 3'-HALONUCLEOSIDES
US20050131224A1 (en) *	2003-12-15	2005-06-16	Cti Pet Systems, Inc.	Method for preparing radiolabeled thymidine
US7160537B2 (en) *	2003-12-15	2007-01-09	Siemens Medical Solutions Usa, Inc.	Method for preparing radiolabeled thymidine having low chromophoric byproducts
US8895531B2 (en)	2006-03-23	2014-11-25	Rfs Pharma Llc	2′-fluoronucleoside phosphonates as antiviral agents
US20070243798A1 (en) *	2006-04-18	2007-10-18	3M Innovative Properties Company	Embossed structured abrasive article and method of making and using the same
KR20160076373A (ko)	2014-12-22	2016-06-30	김기범	양식용 패각 고정을 위한 로프 어셈블리

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DE292023C (cs) *
US4211773A (en) *	1978-10-02	1980-07-08	Sloan Kettering Institute For Cancer Research	5-Substituted 1-(2'-Deoxy-2'-substituted-β-D-arabinofuranosyl)pyrimidine nucleosides
CA1340645C (en) *	1987-04-17	1999-07-13	Victor E. Marquez	Acid stable dideoxynucleosides active against the cytopathic effects of human immunodeficiency virus
GB8712115D0 (en) *	1987-05-22	1987-06-24	Hoffmann La Roche	Pyrimidine derivatives
JPH01100190A (ja) *	1987-10-12	1989-04-18	Asahi Glass Co Ltd	ヌクレオシド類
NZ226672A (en) *	1987-10-30	1991-07-26	Hoffmann La Roche	6-amino-9-(2,3-dideoxy-2-fluoro-b-d-threopentofuranosyl)-9h-purine derivatives and pharmaceutical compositions

1987
- 1987-11-12 US US07/120,051 patent/US4908440A/en not_active Expired - Lifetime
1988
- 1988-11-04 NZ NZ226845A patent/NZ226845A/xx unknown
- 1988-11-04 YU YU204888A patent/YU47121B/sh unknown
- 1988-11-07 ZA ZA888313A patent/ZA888313B/xx unknown
- 1988-11-09 IL IL8833088A patent/IL88330A/en not_active IP Right Cessation
- 1988-11-09 FI FI885153A patent/FI90244C/fi not_active IP Right Cessation
- 1988-11-09 NO NO884995A patent/NO169492C/no unknown
- 1988-11-11 HU HU885779A patent/HU199499B/hu not_active IP Right Cessation
- 1988-11-11 CZ CS887431A patent/CZ278366B6/cs not_active IP Right Cessation
- 1988-11-11 ES ES88118870T patent/ES2061609T3/es not_active Expired - Lifetime
- 1988-11-11 CZ CS905451A patent/CZ278394B6/cs not_active IP Right Cessation
- 1988-11-11 DD DD88321728A patent/DD275874A5/de unknown
- 1988-11-11 AU AU25042/88A patent/AU615960B2/en not_active Ceased
- 1988-11-11 CZ CS905452A patent/CZ278395B6/cs not_active IP Right Cessation
- 1988-11-11 SK SK7431-88A patent/SK743188A3/sk unknown
- 1988-11-11 SK SK5452-90A patent/SK278017B6/sk unknown
- 1988-11-11 IE IE340688A patent/IE62227B1/en not_active IP Right Cessation
- 1988-11-11 EP EP88118870A patent/EP0316017B1/en not_active Expired - Lifetime
- 1988-11-11 DE DE3887273T patent/DE3887273T2/de not_active Expired - Fee Related
- 1988-11-11 KR KR1019880014854A patent/KR920004459B1/ko not_active Expired
- 1988-11-11 DK DK198806316A patent/DK173971B1/da not_active IP Right Cessation
- 1988-11-11 JP JP63284077A patent/JPH01153698A/ja active Pending
- 1988-11-11 PT PT88994A patent/PT88994B/pt not_active IP Right Cessation
- 1988-11-11 AT AT88118870T patent/ATE100461T1/de not_active IP Right Cessation
- 1988-11-14 CA CA000583061A patent/CA1340961C/en not_active Expired - Fee Related
1989
- 1989-07-11 US US07/378,331 patent/US4973677A/en not_active Expired - Lifetime
1990
- 1990-09-13 US US07/581,941 patent/US5126506A/en not_active Expired - Lifetime
1992
- 1992-03-26 US US07/857,850 patent/US5218106A/en not_active Expired - Lifetime
1993
- 1993-05-24 JP JP5155978A patent/JP2699050B2/ja not_active Expired - Fee Related
- 1993-05-24 JP JP5155977A patent/JP2699049B2/ja not_active Expired - Fee Related
1997
- 1997-01-22 JP JP9009099A patent/JP2811561B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DE3887273D1 (de)	1994-03-03
FI90244B (fi)	1993-09-30
DK173971B1 (da)	2002-03-18
JP2699049B2 (ja)	1998-01-19
JP2811561B2 (ja)	1998-10-15
HU199499B (en)	1990-02-28
EP0316017A2 (en)	1989-05-17
EP0316017B1 (en)	1994-01-19
HUT48266A (en)	1989-05-29
AU615960B2 (en)	1991-10-17
US4973677A (en)	1990-11-27
US5218106A (en)	1993-06-08
CZ278395B6 (en)	1993-12-15
US5126506A (en)	1992-06-30
FI885153L (fi)	1989-05-13
JPH0649091A (ja)	1994-02-22
KR920004459B1 (ko)	1992-06-05
DE3887273T2 (de)	1994-05-19
JPH0648947A (ja)	1994-02-22
JPH01153698A (ja)	1989-06-15
PT88994A (pt)	1989-09-14
CZ278366B6 (en)	1993-12-15
JPH09183731A (ja)	1997-07-15
YU204888A (en)	1990-04-30
KR890008161A (ko)	1989-07-10
CZ545290A3 (en)	1993-08-11
CZ743188A3 (en)	1993-08-11
SK277919B6 (en)	1995-08-09
NO884995L (no)	1989-05-16
IL88330A (en)	1995-03-15
DK631688A (da)	1989-05-13
YU47121B (sh)	1994-12-28
AU2504288A (en)	1989-05-25
CZ545190A3 (en)	1993-08-11
DK631688D0 (da)	1988-11-11
NO884995D0 (no)	1988-11-09
IE883406L (en)	1989-05-12
CZ278394B6 (en)	1993-12-15
NZ226845A (en)	1991-10-25
SK545290A3 (en)	1995-10-11
NO169492B (no)	1992-03-23
JP2699050B2 (ja)	1998-01-19
SK743188A3 (en)	1995-08-09
EP0316017A3 (en)	1990-05-30
NO169492C (no)	1993-01-12
IL88330A0 (en)	1989-06-30
ZA888313B (en)	1989-07-26
ATE100461T1 (de)	1994-02-15
SK278017B6 (en)	1995-10-11
FI90244C (fi)	1994-01-10
ES2061609T3 (es)	1994-12-16
CA1340961C (en)	2000-04-18
FI885153A0 (fi)	1988-11-09
IE62227B1 (en)	1995-01-11
PT88994B (pt)	1995-03-31
US4908440A (en)	1990-03-13

Legal Events

Date	Code	Title	Description
2004-04-28	IF04	In force in the year 2004	Expiry date: 20081112

Publication	Publication Date	Title
DE3887273T2 (de)	1994-05-19	2',3'-Dideoxy-2'-fluornucleoside.
EP0797580B1 (de)	2002-04-10	Nucleosid-derivate mit photolabilen schutzgruppen
DE69407419T2 (de)	1998-07-30	2' oder 3' -deoxy- und 2' -dideoxy-beta-l-pentafuranonukleoside, verfahren zur herstellung und anwendung in der therapie, insbesondere als antivirale wirkstoffe
DE69503129T2 (de)	1999-02-18	Pteridin-nukleotidderivate als fluoreszierende sonden
DE60005501T2 (de)	2004-06-24	4'-c-ethynyl-pyrimidine nukleoside
DE69109482T2 (de)	1996-02-15	Pyrimidinnucleosidderivat.
DE68922235T2 (de)	1995-08-31	Durch Acetylen, Cyan oder Allen substituierte Aristeromycin- oder Adenosin-Derivate.
CH500203A (de)	1970-12-15	Verfahren zur Herstellung von Nucleosiden
DE3390162T1 (de)	1985-02-21	Desoxyuridinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Pharmazeutika
DE60204859T2 (de)	2006-04-27	Verfahren zur Herstellung von 2'-Halo-beta-L-arabino-furanosylnucleosiden
DE69112628T2 (de)	1996-04-04	2'-fluorofuranosylderivate und verfahren zur herstellung von 2'-fluoropyrimidin- und 2'-fluoropurin-nucleosiden.
EP1224198B1 (de)	2003-04-23	Nucleosid-derivate mit photolabilen schutzgruppen
KR920004982B1 (ko)	1992-06-22	2',3'-디데옥시-2',3'-디데히드로-2'-플루오로뉴클레오사이드류
AT267074B (de)	1968-12-10	Verfahren zur Herstellung von 5-Fluoro-uracil- und 5-Fluoro-cytosin-Nucleosiden
DE3177285T2 (de)	1992-12-10	Purin- und pyrimidin-verbindungen und deren verwendung als antivirusmittel.
DD268475A1 (de)	1989-05-31	Verfahren zur herstellung von 3'-desoxy-3'-fluor-nucleosiden