CH660486A5 - Verfahren zur herstellung von 5-(e)-(2-bromvinyl)-2'-desoxyuridin. - Google Patents

Verfahren zur herstellung von 5-(e)-(2-bromvinyl)-2'-desoxyuridin. Download PDF

Info

Publication number: CH660486A5
Authority: CH; Switzerland
Prior art keywords: deoxyuridine; compound; general formula; formula; group
Prior art date: 1982-08-04

Application number

CH4019/83A

Other languages

German (de)

English (en)

Inventor

Anna-Borbas Dr Szabolcs

Laszlo Dr Oetvoes

Janos Dr Sagi

Helga-Feuer Dr Tuedoes

Zoltan Ratonyi

Tibor Gal

Lajos Voeroeshazy

Ivan Dr Daroczy

Dieter Dr Barwolf

Juergen Dr Reefschlager

Hellmut Dr Just

Original Assignee

Magyar Tudomanyos Akademia

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.)

1982-08-04

Filing date

1983-07-22

Publication date

1987-04-30

1983-07-22 Application filed by Magyar Tudomanyos Akademia, Akad Wissenschaften Ddr filed Critical Magyar Tudomanyos Akademia

1987-04-30 Publication of CH660486A5 publication Critical patent/CH660486A5/de

Links

ODZBBRURCPAEIQ-PIXDULNESA-N helpin Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(\C=C\Br)=C1 ODZBBRURCPAEIQ-PIXDULNESA-N 0.000 title claims description 9
238000004519 manufacturing process Methods 0.000 title claims description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 26
150000001875 compounds Chemical class 0.000 claims description 23
238000000034 method Methods 0.000 claims description 21
239000000203 mixture Substances 0.000 claims description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 13
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 7
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
-1 dibromo compound Chemical class 0.000 claims description 5
238000002955 isolation Methods 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
230000031709 bromination Effects 0.000 claims description 4
238000005893 bromination reaction Methods 0.000 claims description 4
150000008282 halocarbons Chemical class 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
125000000950 dibromo group Chemical group Br* 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 2
239000011230 binding agent Substances 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
239000000796 flavoring agent Substances 0.000 claims description 2
235000013355 food flavoring agent Nutrition 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
239000003814 drug Substances 0.000 claims 1
239000013067 intermediate product Substances 0.000 claims 1
229940086542 triethylamine Drugs 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
229910052794 bromium Inorganic materials 0.000 description 10
239000000047 product Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
238000010992 reflux Methods 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
239000007858 starting material Substances 0.000 description 5
ZKHGIPARYPCVPA-TXICZTDVSA-N (2S,3R,4S,5R)-2-chloro-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound OC[C@H]1O[C@@H](Cl)[C@H](O)[C@@H]1O ZKHGIPARYPCVPA-TXICZTDVSA-N 0.000 description 4
BLXGZIDBSXVMLU-OWOJBTEDSA-N 5-[(e)-2-bromoethenyl]-1h-pyrimidine-2,4-dione Chemical compound Br\C=C\C1=CNC(=O)NC1=O BLXGZIDBSXVMLU-OWOJBTEDSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
NRTLTGGGUQIRRT-UHFFFAOYSA-N triethylazanium;bromide Chemical compound [Br-].CC[NH+](CC)CC NRTLTGGGUQIRRT-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 3
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 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
239000002808 molecular sieve Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
YNYDWEIQSDFDLK-UHFFFAOYSA-N 5-acetyl-1h-pyrimidine-2,4-dione Chemical compound CC(=O)C1=CNC(=O)NC1=O YNYDWEIQSDFDLK-UHFFFAOYSA-N 0.000 description 2
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
229910021547 Lithium tetrachloropalladate(II) hydrate Inorganic materials 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
230000020176 deacylation Effects 0.000 description 2
238000005947 deacylation reaction Methods 0.000 description 2
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000002032 methanolic fraction Substances 0.000 description 2
229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
HFEXWXMEGUJTQB-OWOJBTEDSA-N (e)-3-(2,4-dioxo-1h-pyrimidin-5-yl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CNC(=O)NC1=O HFEXWXMEGUJTQB-OWOJBTEDSA-N 0.000 description 1
FSMXNEGQNNJFJD-MILTYZGVSA-N 1-[(2R,4S,5R)-4-acetyl-4-hydroxy-5-(1-hydroxy-2-oxopropyl)oxolan-2-yl]-5-ethylpyrimidine-2,4-dione Chemical compound C(C)(=O)[C@@]1(C[C@@H](O[C@@H]1C(O)C(C)=O)N1C(=O)NC(=O)C(=C1)CC)O FSMXNEGQNNJFJD-MILTYZGVSA-N 0.000 description 1
RSHAQOGUDNIQLJ-IYOUNJFTSA-N 1-[(2S,4S,5R)-2-(4-chlorobenzoyl)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-ethylpyrimidine-2,4-dione Chemical compound ClC1=CC=C(C(=O)[C@@]2(C[C@H](O)[C@@H](CO)O2)N2C(=O)NC(=O)C(=C2)CC)C=C1 RSHAQOGUDNIQLJ-IYOUNJFTSA-N 0.000 description 1
FEJKHHYOIOYSGL-VAOFZXAKSA-N 1-[(2r,4s,5r)-2-ethyl-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound C1=CC(=O)NC(=O)N1[C@@]1(CC)C[C@H](O)[C@@H](CO)O1 FEJKHHYOIOYSGL-VAOFZXAKSA-N 0.000 description 1
MXHRCPNRJAMMIM-ULQXZJNLSA-N 1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-tritiopyrimidine-2,4-dione Chemical compound O=C1NC(=O)C([3H])=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 MXHRCPNRJAMMIM-ULQXZJNLSA-N 0.000 description 1
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
ASJSAQIRZKANQN-CRCLSJGQSA-N 2-deoxy-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)CC=O ASJSAQIRZKANQN-CRCLSJGQSA-N 0.000 description 1
RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
ZRYZBEQILKESAW-UHFFFAOYSA-N 5-ethenyl-1h-pyrimidine-2,4-dione Chemical compound C=CC1=CNC(=O)NC1=O ZRYZBEQILKESAW-UHFFFAOYSA-N 0.000 description 1
RHIULBJJKFDJPR-UHFFFAOYSA-N 5-ethyl-1h-pyrimidine-2,4-dione Chemical compound CCC1=CNC(=O)NC1=O RHIULBJJKFDJPR-UHFFFAOYSA-N 0.000 description 1
OHAMXGZMZZWRCA-UHFFFAOYSA-N 5-formyluracil Chemical compound OC1=NC=C(C=O)C(O)=N1 OHAMXGZMZZWRCA-UHFFFAOYSA-N 0.000 description 1
ODZBBRURCPAEIQ-DJLDLDEBSA-N Brivudine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(C=CBr)=C1 ODZBBRURCPAEIQ-DJLDLDEBSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
208000009889 Herpes Simplex Diseases 0.000 description 1
208000007514 Herpes zoster Diseases 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000700605 Viruses Species 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
230000000840 anti-viral effect Effects 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
HMFHBZSHGGEWLO-TXICZTDVSA-N beta-D-ribose Chemical group OC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-TXICZTDVSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
230000006196 deacetylation Effects 0.000 description 1
238000003381 deacetylation reaction Methods 0.000 description 1
238000007269 dehydrobromination reaction Methods 0.000 description 1
MXHRCPNRJAMMIM-UHFFFAOYSA-N desoxyuridine Natural products C1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 MXHRCPNRJAMMIM-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
NGYIMTKLQULBOO-UHFFFAOYSA-L mercury dibromide Chemical compound Br[Hg]Br NGYIMTKLQULBOO-UHFFFAOYSA-L 0.000 description 1
238000006140 methanolysis reaction Methods 0.000 description 1
125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic 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
239000006072 paste Substances 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
KQTXIZHBFFWWFW-UHFFFAOYSA-L silver(I) carbonate Inorganic materials [Ag]OC(=O)O[Ag] KQTXIZHBFFWWFW-UHFFFAOYSA-L 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000004809 thin layer chromatography Methods 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages

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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH4019/83A 1982-08-04 1983-07-22 Verfahren zur herstellung von 5-(e)-(2-bromvinyl)-2'-desoxyuridin. CH660486A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU822506A HU187736B (en)	1982-08-04	1982-08-04	Process for producing /e/ -5-/2-bromovinyl/-2-comma above-deoxyuridine and o-acyl derivatives

Publications (1)

Publication Number	Publication Date
CH660486A5 true CH660486A5 (de)	1987-04-30

Family

ID=10959738

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH4019/83A CH660486A5 (de)	1982-08-04	1983-07-22	Verfahren zur herstellung von 5-(e)-(2-bromvinyl)-2'-desoxyuridin.

Country Status (12)

Country	Link
AT (1)	AT380688B (cs)
BE (1)	BE897434A (cs)
CH (1)	CH660486A5 (cs)
CS (1)	CS251078B2 (cs)
DE (1)	DE3328238A1 (cs)
FI (1)	FI74289C (cs)
FR (1)	FR2531437B1 (cs)
GB (1)	GB2125399B (cs)
HU (1)	HU187736B (cs)
IT (1)	IT1185759B (cs)
PL (1)	PL143289B1 (cs)
YU (1)	YU162683A (cs)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EA005497B1 (ru) *	2001-01-03	2005-02-24	Берлин Хеми Аг	Применение фармацевтической композиции, содержащей бривудин, для лечения герпесвирусных инфекций
DE10109657A1 (de) *	2001-02-28	2002-09-05	Menarini Ricerche Spa	Verfahren zur Herstellung von (E)-5-(2-Bromvinyl)-2`-desoxyuridin
CN102432655A (zh) *	2011-10-28	2012-05-02	河南师范大学	一种合成5-((e)-2-溴乙烯基)-2′-脱氧尿嘧啶核苷(溴呋啶)的方法
EP3792271A1 (en)	2019-09-13	2021-03-17	Aurobindo Pharma Limited	A process for the preparation of brivudine
CN115043894A (zh) *	2022-06-22	2022-09-13	华润双鹤药业股份有限公司	一种溴夫定起始物料异构体单晶及其制备方法和应用

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2721466A1 (de) *	1977-05-12	1978-11-16	Robugen Gmbh	Verfahren zur herstellung von 2'-desoxyribofuranosylnucleosiden
GB1601020A (en) *	1978-04-24	1981-10-21	Stichting Grega Vzw	2'-deoxy-5 (2-halogenovinyl)-uridines
DE3002197A1 (de) *	1980-01-22	1981-07-23	Robugen Gmbh Pharmazeutische Fabrik Esslingen A.N., 7300 Esslingen	5-alkylsubstituierte pyrimidin-nukleoside, verfahren zu deren herstellung und daraus hergestellte virostatische und cytostatische mittel
NZ199764A (en) *	1981-03-20	1984-08-24	Beecham Group Plc	5-(2-halogenovinyl)-2'-deoxyuridine derivatives and pharmaceutical compositions
HU183567B (en) *	1981-09-07	1984-05-28	Mta Koezponti Kemiai Kutato In	Process for preparing /e/-5-/2-bromo-vinyl/-uridine and derivatives thereof
EP0082668A1 (en) *	1981-12-18	1983-06-29	Beecham Group Plc	5-(2-Halogenovinyl)-2'-deoxyuridine derivatives, processes for their preparation, pharmaceutical compositions containing them and their use in treating viral infections
EP0095294A1 (en) *	1982-05-22	1983-11-30	Beecham Group Plc	Deoxyuridine compounds, methods for preparing them and their use in medicine
EP0097039A1 (en) *	1982-06-16	1983-12-28	Beecham Group Plc	5-(E-2-halovinyl)-2'-deoxyuridine derivatives, processes for their preparation, pharmaceutical compositions containing them, and their use in treating viral infections

1982
- 1982-08-04 HU HU822506A patent/HU187736B/hu unknown
1983
- 1983-07-22 CH CH4019/83A patent/CH660486A5/de not_active IP Right Cessation
- 1983-08-01 BE BE1/10845A patent/BE897434A/fr not_active IP Right Cessation
- 1983-08-03 FR FR8312777A patent/FR2531437B1/fr not_active Expired
- 1983-08-03 FI FI832809A patent/FI74289C/fi not_active IP Right Cessation
- 1983-08-03 IT IT22401/83A patent/IT1185759B/it active
- 1983-08-03 CS CS835756A patent/CS251078B2/cs unknown
- 1983-08-04 DE DE3328238A patent/DE3328238A1/de not_active Withdrawn
- 1983-08-04 GB GB08321081A patent/GB2125399B/en not_active Expired
- 1983-08-04 YU YU01626/83A patent/YU162683A/xx unknown
- 1983-08-04 AT AT0282583A patent/AT380688B/de not_active IP Right Cessation
- 1983-08-04 PL PL1983243307A patent/PL143289B1/pl unknown

Also Published As

Publication number	Publication date
DE3328238A1 (de)	1984-02-23
GB8321081D0 (en)	1983-09-07
PL243307A1 (en)	1984-11-08
FR2531437A1 (fr)	1984-02-10
FI74289C (fi)	1988-01-11
FR2531437B1 (fr)	1985-10-25
BE897434A (fr)	1984-02-01
AT380688B (de)	1986-06-25
ATA282583A (de)	1985-11-15
FI832809A0 (fi)	1983-08-03
FI832809A7 (fi)	1984-02-05
YU162683A (en)	1986-02-28
GB2125399A (en)	1984-03-07
IT1185759B (it)	1987-11-18
CS251078B2 (en)	1987-06-11
HU187736B (en)	1986-02-28
GB2125399B (en)	1987-04-01
IT8322401A0 (it)	1983-08-03
FI74289B (fi)	1987-09-30
PL143289B1 (en)	1988-01-30

Legal Events

Date	Code	Title	Description
1994-03-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE69806919T2 (de)	2003-02-27	Antivirale pyrimidin-nukleosid-analogen
DE69109631T2 (de)	1995-09-07	2-Substituierte Adenosinderivate und pharmazeutische Zusammensetzungen zur Verwendung gegen Infektionskrankheiten.
DE68923387T2 (de)	1996-01-25	2',3'-Dideoxy-2',2'-difluornucleoside.
DE69025529T2 (de)	1996-10-17	Weitere antivirale Pyrimidin-Nukleosiden
DE3850571T2 (de)	1994-10-27	2',3'-dideoxyribofuranoxid-derivate.
CH643273A5 (de)	1984-05-30	E-5-(2-halogenovinyl)-2'-deoxyuridine und verfahren zu ihrer herstellung.
WO1996018634A2 (de)	1996-06-20	Nucleosid-derivate mit photolabilen schutzgruppen
WO1995007287A1 (fr)	1995-03-16	COMPOSES 2' OU 3'-DEOXY- ET 2', 3'-DIDEOXY-β-L-PENTOFURANONUCLEOSIDES, PROCEDE DE PREPARATION ET APPLICATION THERAPEUTIQUE, NOTAMMENT ANTI-VIRALE
DE3044740C2 (cs)	1989-04-27
DE1695151A1 (de)	1970-12-17	Verfahren zur Herstellung von Nucleosiden
DE3390162T1 (de)	1985-02-21	Desoxyuridinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Pharmazeutika
DE60202483T2 (de)	2005-12-29	Verfahren zur herstellung von l-ribavirin
DE60204859T2 (de)	2006-04-27	Verfahren zur Herstellung von 2'-Halo-beta-L-arabino-furanosylnucleosiden
DE69206893T2 (de)	1996-08-14	Nucleosidderivate und deren Herstellung
DE68914750T2 (de)	1994-10-20	Therapeutische Nucleoside.
DE3719377C2 (de)	1995-09-28	Anthracyclinglykoside, Verfahren zu deren Herstellung und Arzneimittel, welche diese enthalten
DE3508356C2 (cs)	1988-11-17
DE69019052T2 (de)	1995-08-31	Verfahren zur Herstellung von 2'Deoxy-5-trifluoromethyl-ss-uridin.
CH653340A5 (de)	1985-12-31	(e)-5-(2-bromvinyl)-uridine und verfahren zu ihrer herstellung.
FI74289C (fi)	1988-01-11	Foerfarande foer framstaellning av 5-(e)- (2-bromvinyl)-2'-desoxiuridin och dess derivat.
DE68917060T2 (de)	1994-12-08	2'-Methylidenpyrimidin-Nukleoside, ihre Verwendung und Verfahren zu ihrer Herstellung.
EP1224198B1 (de)	2003-04-23	Nucleosid-derivate mit photolabilen schutzgruppen
DE69415506T2 (de)	1999-08-12	Verfahren zur Herstellung von Beta-Thymidine
DE69708950T2 (de)	2002-08-08	Verfahren zur Herstellung von 2'-Deoxy-2'-Halocoformycin oder Stereoisomere davon
DD208359A1 (de)	1984-05-02	Verfahren zur herstellung von 5-(e)-(2-bromvinyl)-2'-desoxyuridin und seinen derivaten