DD292003A5 - Verfahren zum herstellen von 2-amino-oxazolin-verbindungen - Google Patents

Verfahren zum herstellen von 2-amino-oxazolin-verbindungen Download PDF

Info

Publication number: DD292003A5
Authority: DD; German Democratic Republic
Prior art keywords: hydrogen; amino; formula; substituted; siiyi
Prior art date: 1988-07-12

Application number

DD89337873A

Other languages

German (de)

English (en)

Inventor

Charles W Murtiashaw

Original Assignee

��@��Kk��

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.)

1988-07-12

Filing date

1989-07-11

Publication date

1991-07-18

1989-07-11 Application filed by ��@��Kk�� filed Critical ��@��Kk��

1991-07-18 Publication of DD292003A5 publication Critical patent/DD292003A5/de

Links

238000004519 manufacturing process Methods 0.000 title abstract description 3
YAXGBZDYGZBRBQ-UHFFFAOYSA-N 4,5-dihydro-1,3-oxazol-2-amine Chemical class NC1=NCCO1 YAXGBZDYGZBRBQ-UHFFFAOYSA-N 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 25
238000000034 method Methods 0.000 claims abstract description 12
-1 2-amino-oxazoline compound Chemical class 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 28
239000001257 hydrogen Substances 0.000 claims description 26
150000002431 hydrogen Chemical class 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
239000007858 starting material Substances 0.000 abstract description 4
208000030507 AIDS Diseases 0.000 abstract description 3
239000002253 acid Substances 0.000 abstract description 2
150000004702 methyl esters Chemical class 0.000 abstract 1
230000001225 therapeutic effect Effects 0.000 abstract 1
229940104230 thymidine Drugs 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 18
230000015572 biosynthetic process Effects 0.000 description 14
238000003786 synthesis reaction Methods 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
235000019439 ethyl acetate Nutrition 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
239000003921 oil Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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 6
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
229940113082 thymine Drugs 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical group 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
238000003756 stirring Methods 0.000 description 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
239000003480 eluent Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
HWYJZXYVLPKDLM-UHFFFAOYSA-N methyl 2-methyl-3-oxopropanoate Chemical compound COC(=O)C(C)C=O HWYJZXYVLPKDLM-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
UTMUIPQCQMEAEI-RLKNHCSUSA-N 1-[(2r,4r,5r)-3-bromo-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C(Br)[C@H](O)[C@@H](CO)O1 UTMUIPQCQMEAEI-RLKNHCSUSA-N 0.000 description 2
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 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000002718 pyrimidine nucleoside Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
230000007017 scission Effects 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000010183 spectrum analysis Methods 0.000 description 2
XZMMMZJDMWAFNG-NODZRDHJSA-N 1-[(2r,4s,5r)-4-acetyl-3-bromo-4-hydroxy-5-(1-hydroxy-2-oxopropyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound BrC1[C@](C(C)=O)(O)[C@@H](C(O)C(=O)C)O[C@H]1N1C(=O)NC(=O)C(C)=C1 XZMMMZJDMWAFNG-NODZRDHJSA-N 0.000 description 1
UYCLMYDTNVHCAN-UHFFFAOYSA-N 2,3-dibromo-2-methylpropanoic acid Chemical compound BrCC(Br)(C)C(O)=O UYCLMYDTNVHCAN-UHFFFAOYSA-N 0.000 description 1
VOKUMXABRRXHAR-UHFFFAOYSA-N 2-methyl-3-oxopropanoic acid Chemical compound O=CC(C)C(O)=O VOKUMXABRRXHAR-UHFFFAOYSA-N 0.000 description 1
PWWIAWDCLANFSS-UHFFFAOYSA-N 3-bromo-2-methylprop-2-enoic acid Chemical compound BrC=C(C)C(O)=O PWWIAWDCLANFSS-UHFFFAOYSA-N 0.000 description 1
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
OTVLXFGCWJFXJU-UHFFFAOYSA-N 3-methylbutan-2-yl nitrate Chemical compound CC(C)C(C)O[N+]([O-])=O OTVLXFGCWJFXJU-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
SRBFZHDQGSBBOR-OWMBCFKOSA-N L-ribopyranose Chemical compound O[C@H]1COC(O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-OWMBCFKOSA-N 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical class [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
125000005396 acrylic acid ester group Chemical group 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
238000004458 analytical method Methods 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
239000003443 antiviral agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229960003920 cocaine Drugs 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
FHHZOYXKOICLGH-UHFFFAOYSA-N dichloromethane;ethanol Chemical compound CCO.ClCCl FHHZOYXKOICLGH-UHFFFAOYSA-N 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
XEQYPQHAQCSASZ-SNAWJCMRSA-N methyl (e)-3-methoxy-2-methylprop-2-enoate Chemical compound CO\C=C(/C)C(=O)OC XEQYPQHAQCSASZ-SNAWJCMRSA-N 0.000 description 1
GVLXNUSEDDXIGJ-UHFFFAOYSA-N methyl 2,3-dibromo-2-methylpropanoate Chemical compound COC(=O)C(C)(Br)CBr GVLXNUSEDDXIGJ-UHFFFAOYSA-N 0.000 description 1
KWVOFUZCFMSWGF-UHFFFAOYSA-N methyl 2-acetamido-3-(2-fluorophenyl)propanoate Chemical compound COC(=O)C(NC(C)=O)CC1=CC=CC=C1F KWVOFUZCFMSWGF-UHFFFAOYSA-N 0.000 description 1
HQKAHZMYDADHPE-UHFFFAOYSA-N methyl 3-bromo-2-methylprop-2-enoate Chemical compound COC(=O)C(C)=CBr HQKAHZMYDADHPE-UHFFFAOYSA-N 0.000 description 1
229940017219 methyl propionate Drugs 0.000 description 1
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
239000002777 nucleoside Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/14—Ortho-condensed systems
- 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
- 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
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- 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
- C07H19/09—Pyrimidine radicals with arabinosyl as the saccharide radical

Landscapes

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

DD89337873A 1988-07-12 1989-07-11 Verfahren zum herstellen von 2-amino-oxazolin-verbindungen DD292003A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/217,906 US5008384A (en)	1988-07-12	1988-07-12	Process for the production of O.sup. 2,2'-anhydro-1-(β-D-arabinofuranosyl)thymine

Publications (1)

Publication Number	Publication Date
DD292003A5 true DD292003A5 (de)	1991-07-18

Family

ID=22812966

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DD89337873A DD292003A5 (de)	1988-07-12	1989-07-11	Verfahren zum herstellen von 2-amino-oxazolin-verbindungen
DD89330684A DD284024A5 (de)	1988-07-12	1989-07-11	Verfahren zum herstellen von o hoch 2 tief ,2'-anhydro-1-(beta-d-arabinofuranosyl)thymin

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DD89330684A DD284024A5 (de)	1988-07-12	1989-07-11	Verfahren zum herstellen von o hoch 2 tief ,2'-anhydro-1-(beta-d-arabinofuranosyl)thymin

Country Status (21)

Country	Link
US (1)	US5008384A (da)
EP (1)	EP0351126B1 (da)
JP (1)	JPH075626B2 (da)
KR (1)	KR910008112B1 (da)
CN (1)	CN1039423A (da)
AT (1)	ATE117314T1 (da)
AU (1)	AU603042B2 (da)
CA (1)	CA1315776C (da)
DD (2)	DD292003A5 (da)
DE (1)	DE68920648T2 (da)
DK (1)	DK342189A (da)
ES (1)	ES2066853T3 (da)
FI (1)	FI893364A7 (da)
GR (1)	GR3015293T3 (da)
HU (1)	HUT50843A (da)
IE (1)	IE65735B1 (da)
IL (1)	IL90884A0 (da)
NO (1)	NO892821L (da)
PT (1)	PT91113B (da)
YU (1)	YU138789A (da)
ZA (1)	ZA895259B (da)

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WO1992009599A1 (fr) *	1990-11-30	1992-06-11	Yamasa Shoyu Kabushiki Kaisha	PROCEDE DE PRODUCTION DE 1-(2,3-DIDESOXY-β-D-GLYCERO-PENT-2-ENOFURANOSYL)THYMINE
US5596087A (en) *	1994-05-20	1997-01-21	Council Of Scientific & Industrial Research	Process for the preparation of beta thymidine
US7125983B2 (en)	2000-11-29	2006-10-24	Mitsui Chemicals, Inc.	L-nucleic acid derivatives and process for the synthesis thereof
ES2243726T3 (es) *	2001-03-30	2005-12-01	Gilead Sciences, Inc.	Procedimiento de preparacion de 2'-halo-beta-l-arabinofuranosil nucleosidos.
DE10216426A1 (de) *	2002-04-12	2003-10-23	Boehringer Ingelheim Pharma	Verfahren zur Herstellung von beta-L-2'Deoxy-Thymidin
US7595390B2 (en)	2003-04-28	2009-09-29	Novartis Ag	Industrially scalable nucleoside synthesis
EP1639121A4 (en)	2003-06-30	2008-04-16	Idenix Cayman Ltd	SYNTHESIS OF BETA-L-2-DESOXYNUCLEOSIDES
BRPI0709401A2 (pt)	2006-03-15	2011-07-05	Novartis Ag	processo para a preparação de derivados de ácido beta-nucléico e intermediários dos mesmos
US7998967B2 (en)	2008-03-03	2011-08-16	Tosk, Incorporated	Methotrexate adjuvants to reduce toxicity and methods for using the same
US11446303B2 (en)	2019-06-21	2022-09-20	Tosk, Inc.	Uridine phosphorylase (UPase) inhibitors for treatment of liver conditions

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US3322747A (en) *	1965-04-01	1967-05-30	Merck & Co Inc	Thionocarbonate nucleosides
US3463850A (en) *	1967-01-03	1969-08-26	Merck & Co Inc	Arabinofuranosyl 2-thiopyrimidines and pharmaceutical compositions thereof
US3658788A (en) *	1969-06-06	1972-04-25	Salk Inst For Biological Studi	Aminooxazolines and products thereof and processes for synthesizing same
US3812098A (en) *	1970-03-19	1974-05-21	Syntex Inc	O2,2'-anhydro-1-(beta-d-arabinofuranosyl)-cytosine derivatives and methods of making and related procedures
US3792040A (en) *	1970-03-19	1974-02-12	Syntex Corp	Acyl derivatives of o2,2'-anhydro-1-(beta-d-arabinofuranosyl)-cytosines and methods of preparing
US3709874A (en) *	1970-03-19	1973-01-09	Syntex Corp	1-beta-d-arabinofuranosyl cytosine derivatives and methods of preparing
US3920630A (en) *	1970-09-24	1975-11-18	Upjohn Co	2,2{40 -Anhydro-ara-cytidine compounds and process of preparation
SE391183B (sv) *	1971-04-15	1977-02-07	Asahi Chemical Ind	2',3'-0-sulfinylcytidin och syraadditionssalter derav till anvendning som mellanprodukt for framstellning av 2,2'-anhydro-(1-beta-d-arabinofuranosyl) cytosin
US3978042A (en) *	1975-01-31	1976-08-31	The Upjohn Company	Process for preparing cyclocytidine derivatives
US4140850A (en) *	1977-08-29	1979-02-20	The Upjohn Company	2,2'-Anhydrotriazine nucleosides and process for preparing the same
JPS5649398A (en) *	1979-09-28	1981-05-02	Yamasa Shoyu Co Ltd	Preparation of 1-beta-d-arabinofuranosyl-2,2'-cyclothymine
JPS636557A (ja) *	1986-06-26	1988-01-12	Sharp Corp	微細パタ−ン形成方法

1988
- 1988-07-12 US US07/217,906 patent/US5008384A/en not_active Expired - Lifetime
1989
- 1989-07-05 DE DE68920648T patent/DE68920648T2/de not_active Expired - Fee Related
- 1989-07-05 ES ES89306820T patent/ES2066853T3/es not_active Expired - Lifetime
- 1989-07-05 EP EP89306820A patent/EP0351126B1/en not_active Expired - Lifetime
- 1989-07-05 IL IL90884A patent/IL90884A0/xx unknown
- 1989-07-05 AT AT89306820T patent/ATE117314T1/de not_active IP Right Cessation
- 1989-07-07 NO NO89892821A patent/NO892821L/no unknown
- 1989-07-10 CN CN89104789A patent/CN1039423A/zh active Pending
- 1989-07-10 CA CA000605243A patent/CA1315776C/en not_active Expired - Fee Related
- 1989-07-10 PT PT91113A patent/PT91113B/pt not_active IP Right Cessation
- 1989-07-10 JP JP1177876A patent/JPH075626B2/ja not_active Expired - Fee Related
- 1989-07-11 IE IE223389A patent/IE65735B1/en not_active IP Right Cessation
- 1989-07-11 FI FI893364A patent/FI893364A7/fi not_active Application Discontinuation
- 1989-07-11 DK DK342189A patent/DK342189A/da not_active Application Discontinuation
- 1989-07-11 DD DD89337873A patent/DD292003A5/de not_active IP Right Cessation
- 1989-07-11 HU HU893491A patent/HUT50843A/hu unknown
- 1989-07-11 DD DD89330684A patent/DD284024A5/de not_active IP Right Cessation
- 1989-07-11 KR KR1019890009853A patent/KR910008112B1/ko not_active Expired
- 1989-07-11 AU AU38020/89A patent/AU603042B2/en not_active Ceased
- 1989-07-11 YU YU01387/89A patent/YU138789A/xx unknown
- 1989-07-11 ZA ZA895259A patent/ZA895259B/xx unknown
1995
- 1995-03-03 GR GR950400471T patent/GR3015293T3/el unknown

Also Published As

Publication number	Publication date
KR910008112B1 (ko)	1991-10-10
ZA895259B (en)	1991-02-27
JPH075626B2 (ja)	1995-01-25
NO892821D0 (no)	1989-07-07
DE68920648D1 (de)	1995-03-02
US5008384A (en)	1991-04-16
DD284024A5 (de)	1990-10-31
PT91113A (pt)	1990-02-08
HUT50843A (en)	1990-03-28
IL90884A0 (en)	1990-02-09
YU138789A (en)	1990-12-31
DK342189A (da)	1990-01-15
DK342189D0 (da)	1989-07-11
KR900001704A (ko)	1990-02-27
EP0351126B1 (en)	1995-01-18
AU603042B2 (en)	1990-11-01
CN1039423A (zh)	1990-02-07
EP0351126A2 (en)	1990-01-17
DE68920648T2 (de)	1995-05-18
NO892821L (no)	1990-01-15
GR3015293T3 (en)	1995-06-30
FI893364A7 (fi)	1990-01-13
PT91113B (pt)	1995-01-31
ATE117314T1 (de)	1995-02-15
EP0351126A3 (en)	1990-10-24
JPH0259598A (ja)	1990-02-28
IE892233L (en)	1990-01-12
CA1315776C (en)	1993-04-06
ES2066853T3 (es)	1995-03-16
IE65735B1 (en)	1995-11-15
AU3802089A (en)	1990-04-26
FI893364A0 (fi)	1989-07-11

Legal Events

Date	Code	Title	Description
1995-05-24	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE2539963C2 (de)	1987-01-22	Purinverbindungen, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen, welche diese Verbindungen enthalten
DE69210141T2 (de)	1996-10-31	Herstellung von Fluoxetin und Zwischenverbindungen
DE69229492T2 (de)	2000-02-17	Verfahren zur Herstellung von azyklischen Nukleosiden
DE69022176T2 (de)	1996-02-15	Zwischenverbindung für 2-alkynyladenosinherstellung, herstellung dieser zwischenverbindung, herstellung von 2-alkynyladenosin aus diesem zwischenprodukt sowie stabiles 2-alkynyladenosinderivat.
EP0003229A1 (de)	1979-08-08	Neues Verfahren zur Herstellung von Nucleosiden
EP0056265A2 (de)	1982-07-21	5'-Ester von Pyrimidinnucleosiden mit antiviraler Wirksamkeit, Verfahren zur Herstellung und daraus hergestellte Arzneimittel
DE3856158T2 (de)	1998-08-20	Verfahren zur Herstellung von Zwischenverbindungen verwendbar in der Herstellung von 2',2'-Difluoronucleosiden
DE3044740C2 (da)	1989-04-27
CH500203A (de)	1970-12-15	Verfahren zur Herstellung von Nucleosiden
DD292003A5 (de)	1991-07-18	Verfahren zum herstellen von 2-amino-oxazolin-verbindungen
DE69615591T2 (de)	2002-06-06	Verfahren zur Herstellung von Purinderivaten
DE2237632C3 (de)	1980-03-06	H4-Hydro3qr-6-methyl-2-pvrimidinyD-3-methyl-pyrazolin-5-on, ein Verfahren zu dessen Herstellung und dessen Verwendung zur Herstellung von l-(4-Methoxy-6methyl-2-pyrimidinyl)-3-methyl-5-methoxypyrazol
DE69027084T2 (de)	1996-10-24	Verfahren zur Herstellung von Purinverbindungen
DE3913039C2 (de)	1993-11-25	Verfahren zur Herstellung von Diacylderivaten von 2'-Deoxy-5-fluoruridin über eine neue Zwischenverbindung
DE69707860T2 (de)	2002-04-11	Verfahren zur herstellung von tetrahydroindolizinen
EP0252353B1 (de)	1990-08-29	4-Benzyloxy-3-pyrrolin-2-on-1-yl-acetamid, dessen Herstellung und Verwendung
DD246301A5 (de)	1987-06-03	Verfahren zur herstellung von 9-(2-hydroxyaethoxy-methyl)granin
CH628336A5 (de)	1982-02-26	Verfahren zur herstellung von 5-fluoruracil und dessen derivaten.
DE69424475T2 (de)	2001-01-18	Verfahren zur Herstellung von 1-(2'-deoxy-beta-D-erythropentofuranosyl)-5-trifluormethyluracil Derivaten
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DE60202245T2 (de)	2005-09-01	Herstellungsmethode von Famciclovir und Herstellungs- bzw. Kristallisationsmethode eines entsprechenden Intermediates
DE69822222T2 (de)	2005-01-13	Verfahren zur herstellung von beta-hydroxy-gamma-butyrolacton-derivaten und beta-(meth)acryloxy-gamma-butyrolacton-derivaten
DE60101312T2 (de)	2004-08-26	Verfahren zur herstellung von indolopyrrolocarbazol-derivaten, deren zwischenprodukte sowie verfahren zur herstellung der zwischenprodukte
DE2122070A1 (de)	1972-06-08	1 Veratryl 4 methyl 5 athyl 7,8 dimethoxy 2,3 diazabicyclo eckige Klam mer auf 5,4,0 eckige Klammer zu undeca pentaen (1,3,6,8,10) und seine Verwendung