DD293116A5 - Verfahren zur herstellung von 9-substituierten guaninderivaten und zwischenprodukten fuer dieses verfahren - Google Patents

Verfahren zur herstellung von 9-substituierten guaninderivaten und zwischenprodukten fuer dieses verfahren Download PDF

Info

Publication number: DD293116A5
Authority: DD; German Democratic Republic
Prior art keywords: imidazole; amino; carboxamide; thiocarbamoyl; methyl
Prior art date: 1989-03-20

Application number

DD90338906A

Other languages

German (de)

English (en)

Inventor

Borge Alhede

Finn P Clausen

Jorgen J Christensen

Klaus K Mccluskey

Herbert Preikschat

Original Assignee

�a�@��@��@��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.)

1989-03-20

Filing date

1990-03-20

Publication date

1991-08-22

1990-03-20 Application filed by �a�@��@��@��k�� filed Critical �a�@��@��@��k��

1991-08-22 Publication of DD293116A5 publication Critical patent/DD293116A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 16
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 title claims abstract description 15
238000004519 manufacturing process Methods 0.000 title description 3
239000013067 intermediate product Chemical class 0.000 title 1
-1 peroxide compounds Chemical class 0.000 claims abstract description 17
150000003839 salts Chemical class 0.000 claims abstract description 16
229910001385 heavy metal Inorganic materials 0.000 claims abstract description 8
238000002360 preparation method Methods 0.000 claims abstract description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
125000000824 D-ribofuranosyl group Chemical group [H]OC([H])([H])[C@@]1([H])OC([H])(*)[C@]([H])(O[H])[C@]1([H])O[H] 0.000 claims abstract description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
239000000543 intermediate Substances 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 21
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
239000010949 copper Substances 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 5
238000010992 reflux Methods 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
150000002500 ions Chemical class 0.000 claims description 2
229910052745 lead Inorganic materials 0.000 claims description 2
229910052753 mercury Inorganic materials 0.000 claims description 2
229910052709 silver Inorganic materials 0.000 claims description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
238000010306 acid treatment Methods 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
238000007363 ring formation reaction Methods 0.000 abstract description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 2
125000000189 2-deoxyribosyl group Chemical group C1(C[C@H](O)[C@H](O1)CO)* 0.000 abstract description 2
HCUOEKSZWPGJIM-YBRHCDHNSA-N (e,2e)-2-hydroxyimino-6-methoxy-4-methyl-5-nitrohex-3-enamide Chemical compound COCC([N+]([O-])=O)\C(C)=C\C(=N/O)\C(N)=O HCUOEKSZWPGJIM-YBRHCDHNSA-N 0.000 abstract 1
101100162200 Aspergillus parasiticus (strain ATCC 56775 / NRRL 5862 / SRRC 143 / SU-1) aflD gene Proteins 0.000 abstract 1
150000003857 carboxamides Chemical class 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 38
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
229910052757 nitrogen Inorganic materials 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
229910052739 hydrogen Inorganic materials 0.000 description 22
239000000047 product Substances 0.000 description 22
238000002844 melting Methods 0.000 description 19
230000008018 melting Effects 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
238000004128 high performance liquid chromatography Methods 0.000 description 13
239000000843 powder Substances 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 10
NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000000706 filtrate Substances 0.000 description 7
238000001914 filtration Methods 0.000 description 7
229960004150 aciclovir Drugs 0.000 description 5
238000001816 cooling Methods 0.000 description 5
WDOYBEPLTCFIRQ-UHFFFAOYSA-N 2-amino-9-ethyl-3h-purin-6-one Chemical compound N1C(N)=NC(=O)C2=C1N(CC)C=N2 WDOYBEPLTCFIRQ-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 description 4
NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 description 4
229940029575 guanosine Drugs 0.000 description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
KZYOKOLLHMHOLR-UHFFFAOYSA-N 1-benzyl-5-(carbamothioylamino)imidazole-4-carboxamide Chemical compound NC(=S)NC1=C(C(N)=O)N=CN1CC1=CC=CC=C1 KZYOKOLLHMHOLR-UHFFFAOYSA-N 0.000 description 3
SCOKPTHVGOEBIW-UHFFFAOYSA-N 2-[(5-amino-4-carbamoylimidazol-1-yl)methoxy]ethyl acetate Chemical compound CC(=O)OCCOCN1C=NC(C(N)=O)=C1N SCOKPTHVGOEBIW-UHFFFAOYSA-N 0.000 description 3
SMHBTBYHDWNJEG-UHFFFAOYSA-N 2-amino-9-benzyl-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1CC1=CC=CC=C1 SMHBTBYHDWNJEG-UHFFFAOYSA-N 0.000 description 3
YBGIFRCRSMJOMZ-UHFFFAOYSA-N 5-(carbamothioylamino)-1-(2-hydroxyethoxymethyl)imidazole-4-carboxamide Chemical compound NC(=S)NC1=C(C(N)=O)N=CN1COCCO YBGIFRCRSMJOMZ-UHFFFAOYSA-N 0.000 description 3
QTKYYXIZORIEEI-UHFFFAOYSA-N 5-(carbamothioylamino)-1-methylimidazole-4-carboxamide Chemical compound CN1C=NC(C(N)=O)=C1NC(N)=S QTKYYXIZORIEEI-UHFFFAOYSA-N 0.000 description 3
UUWJNBOCAPUTBK-UHFFFAOYSA-N 9-methylguanine Chemical compound N1=C(N)N=C2N(C)C=NC2=C1O UUWJNBOCAPUTBK-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
229910000365 copper sulfate Inorganic materials 0.000 description 3
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
ZANHYKHFPSYAIW-UHFFFAOYSA-N 1-aminoimidazole-4-carboxamide Chemical compound NC(=O)C1=CN(N)C=N1 ZANHYKHFPSYAIW-UHFFFAOYSA-N 0.000 description 2
DVNYTAVYBRSTGK-UHFFFAOYSA-N 5-aminoimidazole-4-carboxamide Chemical compound NC(=O)C=1N=CNC=1N DVNYTAVYBRSTGK-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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 2
239000002253 acid Substances 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 2
150000001718 carbodiimides Chemical class 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 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 description 2
238000005406 washing Methods 0.000 description 2
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
HHCLNZBCCQDVOQ-UHFFFAOYSA-N 1-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]pyrazol-3-yl]methyl]piperazin-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(N1CC2=C(CC1)NN=N2)=O)CN1C(CNCC1)=O HHCLNZBCCQDVOQ-UHFFFAOYSA-N 0.000 description 1
BIPYIUKMNFPYHS-UHFFFAOYSA-N 5-(benzoylcarbamothioylamino)-1-methylimidazole-4-carboxamide Chemical compound CN1C=NC(C(N)=O)=C1NC(=S)NC(=O)C1=CC=CC=C1 BIPYIUKMNFPYHS-UHFFFAOYSA-N 0.000 description 1
DRPRDPXASLIYCT-UUOKFMHZSA-N 5-(carbamothioylamino)-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide Chemical compound NC(=S)NC1=C(C(N)=O)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 DRPRDPXASLIYCT-UUOKFMHZSA-N 0.000 description 1
QFCCFUBHVTZGJS-UHFFFAOYSA-N 5-amino-1-[hydroxy(1-hydroxypropan-2-yloxy)methyl]imidazole-4-carboxamide Chemical compound OCC(C)OC(O)N1C=NC(C(N)=O)=C1N QFCCFUBHVTZGJS-UHFFFAOYSA-N 0.000 description 1
JAODJMVGFQELNO-UHFFFAOYSA-N 5-amino-1-benzylimidazole-4-carboxamide Chemical compound NC1=C(C(=O)N)N=CN1CC1=CC=CC=C1 JAODJMVGFQELNO-UHFFFAOYSA-N 0.000 description 1
WMRBKFPTMPNISL-UHFFFAOYSA-N 5-amino-1-ethylimidazole-4-carboxamide Chemical compound CCN1C=NC(C(N)=O)=C1N WMRBKFPTMPNISL-UHFFFAOYSA-N 0.000 description 1
UZHKJZZQGXMAKP-UHFFFAOYSA-N 5-amino-1-methylimidazole-4-carboxamide Chemical compound CN1C=NC(C(N)=O)=C1N UZHKJZZQGXMAKP-UHFFFAOYSA-N 0.000 description 1
LVONFJCKVYNYTJ-UHFFFAOYSA-N 5-amino-1-propylimidazole-4-carboxamide Chemical compound CCCN1C=NC(C(N)=O)=C1N LVONFJCKVYNYTJ-UHFFFAOYSA-N 0.000 description 1
RTRQQBHATOEIAF-UHFFFAOYSA-N AICA riboside Natural products NC1=C(C(=O)N)N=CN1C1C(O)C(O)C(CO)O1 RTRQQBHATOEIAF-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 1
RTRQQBHATOEIAF-UUOKFMHZSA-N acadesine Chemical compound NC1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 RTRQQBHATOEIAF-UUOKFMHZSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
230000000840 anti-viral effect Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003245 coal Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
OMZSGWSJDCOLKM-UHFFFAOYSA-N copper(II) sulfide Chemical compound [S-2].[Cu+2] OMZSGWSJDCOLKM-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000010353 genetic engineering Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
231100000167 toxic agent Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
- 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
- C07H19/052—Imidazole 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
- C07H19/16—Purine radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Biotechnology (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DD90338906A 1989-03-20 1990-03-20 Verfahren zur herstellung von 9-substituierten guaninderivaten und zwischenprodukten fuer dieses verfahren DD293116A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DK135489A DK135489D0 (da)	1989-03-20	1989-03-20	Fremgangsmaade til fremstilling af 9-substituerede guaninderivater og mellemprodukter til brug ved fremgangsmaaden

Publications (1)

Publication Number	Publication Date
DD293116A5 true DD293116A5 (de)	1991-08-22

Family

ID=8103930

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90338906A DD293116A5 (de)	1989-03-20	1990-03-20	Verfahren zur herstellung von 9-substituierten guaninderivaten und zwischenprodukten fuer dieses verfahren

Country Status (28)

Country	Link
US (1)	US5223619A (pl)
EP (1)	EP0464112B1 (pl)
KR (1)	KR0142098B1 (pl)
AR (1)	AR245719A1 (pl)
AT (1)	ATE112568T1 (pl)
BG (1)	BG60590B1 (pl)
BR (1)	BR9007230A (pl)
CA (1)	CA2047217A1 (pl)
CS (1)	CS9001365A3 (pl)
DD (1)	DD293116A5 (pl)
DE (1)	DE69013146T2 (pl)
DK (2)	DK135489D0 (pl)
ES (1)	ES2061023T3 (pl)
FI (1)	FI97387C (pl)
GE (1)	GEP19971014B (pl)
GR (1)	GR1001096B (pl)
HR (1)	HRP920907B1 (pl)
HU (1)	HU206715B (pl)
IE (1)	IE62042B1 (pl)
LT (1)	LT3183B (pl)
LV (1)	LV10455B (pl)
NO (1)	NO178497C (pl)
PL (1)	PL163313B1 (pl)
RO (1)	RO109737B1 (pl)
RU (2)	RU2090566C1 (pl)
SI (1)	SI9010545A (pl)
WO (1)	WO1990011283A1 (pl)
YU (1)	YU47343B (pl)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1264599B1 (it) *	1993-06-14	1996-10-04	Solar Chem Sa	Processo per la sintesi della 9-(2-idrossietossimetil)- guanina
GB9520364D0 (en) *	1995-10-05	1995-12-06	Chiroscience Ltd	Compouundds
DE69922009T2 (de) *	1998-07-23	2005-04-07	Fujisawa Pharmaceutical Co., Ltd.	Imidazolverbindungen und ihre verwendung als adenosindeaminase-inhibitoren
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1989
- 1989-03-20 DK DK135489A patent/DK135489D0/da not_active Application Discontinuation
1990
- 1990-03-16 IE IE99490A patent/IE62042B1/en unknown
- 1990-03-19 RU RU9093004872A patent/RU2090566C1/ru active
- 1990-03-19 ES ES90905442T patent/ES2061023T3/es not_active Expired - Lifetime
- 1990-03-19 CA CA002047217A patent/CA2047217A1/en not_active Abandoned
- 1990-03-19 US US07/761,890 patent/US5223619A/en not_active Expired - Fee Related
- 1990-03-19 DE DE69013146T patent/DE69013146T2/de not_active Expired - Fee Related
- 1990-03-19 AT AT90905442T patent/ATE112568T1/de not_active IP Right Cessation
- 1990-03-19 KR KR1019910701187A patent/KR0142098B1/ko not_active Expired - Fee Related
- 1990-03-19 HU HU902874A patent/HU206715B/hu not_active IP Right Cessation
- 1990-03-19 EP EP90905442A patent/EP0464112B1/en not_active Expired - Lifetime
- 1990-03-19 WO PCT/DK1990/000077 patent/WO1990011283A1/en not_active Ceased
- 1990-03-19 DK DK90905442.1T patent/DK0464112T3/da active
- 1990-03-19 RO RO148411A patent/RO109737B1/ro unknown
- 1990-03-19 BR BR909007230A patent/BR9007230A/pt not_active Application Discontinuation
- 1990-03-20 SI SI9010545A patent/SI9010545A/sl unknown
- 1990-03-20 YU YU54590A patent/YU47343B/sh unknown
- 1990-03-20 GR GR900100212A patent/GR1001096B/el unknown
- 1990-03-20 PL PL90284379A patent/PL163313B1/pl unknown
- 1990-03-20 CS CS901365A patent/CS9001365A3/cs unknown
- 1990-03-20 DD DD90338906A patent/DD293116A5/de not_active IP Right Cessation
- 1990-03-20 AR AR90316421A patent/AR245719A1/es active
1991
- 1991-09-19 RU SU915001705A patent/RU2042668C1/ru active
- 1991-09-19 NO NO913686A patent/NO178497C/no unknown
- 1991-09-19 FI FI914418A patent/FI97387C/fi active
- 1991-09-20 BG BG95145A patent/BG60590B1/bg unknown
1992
- 1992-10-02 HR HRP-545/90A patent/HRP920907B1/xx not_active IP Right Cessation
- 1992-12-02 LV LVP-92-250A patent/LV10455B/en unknown
1993
- 1993-01-27 LT LTIP297A patent/LT3183B/lt not_active IP Right Cessation
- 1993-08-25 GE GEAP19931494A patent/GEP19971014B/en unknown

Also Published As

Publication number	Publication date
RO109737B1 (ro)	1995-05-30
NO913686L (no)	1991-09-19
GR1001096B (el)	1993-04-28
HRP920907A2 (hr)	1994-04-30
LV10455A (lv)	1995-02-20
NO178497B (no)	1996-01-02
IE62042B1 (en)	1994-12-14
KR0142098B1 (ko)	1998-06-01
CS275359B2 (en)	1992-02-19
DK0464112T3 (da)	1995-03-13
RU2042668C1 (ru)	1995-08-27
HUT59141A (en)	1992-04-28
YU47343B (sh)	1995-01-31
WO1990011283A1 (en)	1990-10-04
GEP19971014B (en)	1997-04-18
BG95145A (bg)	1993-12-24
DE69013146T2 (de)	1995-02-16
PL163313B1 (pl)	1994-03-31
LT3183B (en)	1995-03-27
BG60590B1 (en)	1995-09-29
EP0464112A1 (en)	1992-01-08
IE900994L (en)	1990-09-20
HU902874D0 (en)	1991-12-30
EP0464112B1 (en)	1994-10-05
GR900100212A (en)	1990-07-31
DK135489D0 (da)	1989-03-20
LV10455B (en)	1995-08-20
CS9001365A3 (en)	1992-02-19
YU54590A (sh)	1992-12-21
NO178497C (no)	1996-04-10
SI9010545A (en)	1997-08-31
FI97387B (fi)	1996-08-30
ATE112568T1 (de)	1994-10-15
HRP920907B1 (en)	1998-06-30
BR9007230A (pt)	1992-02-25
LTIP297A (en)	1994-08-25
FI97387C (fi)	1996-12-10
KR920701208A (ko)	1992-08-11
AR245719A1 (es)	1994-02-28
CA2047217A1 (en)	1990-09-21
DE69013146D1 (de)	1994-11-10
NO913686D0 (no)	1991-09-19
RU2090566C1 (ru)	1997-09-20
FI914418A0 (fi)	1991-09-19
US5223619A (en)	1993-06-29
HU206715B (en)	1992-12-28
ES2061023T3 (es)	1994-12-01

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Date	Code	Title	Description
2000-08-17	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE69303879T2 (de)	1997-01-30	Verfahren zur Herstellung von N4-acyl-5'-desoxy-5-fluorocytidinderivate
DE2122991A1 (de)	1972-11-16	Cytidine
DE69013146T2 (de)	1995-02-16	Verfahren zur herstellung von 9-substituierten guaninderivaten und zwischenprodukte zur verwendung im verfahren.
DE1112079B (de)	1961-08-03	Verfahren zur Herstellung von 3, 4-Dihydro-1, 2, 4-benzothiadiazin-1, 1-dioxyden
CA2021290A1 (en)	1991-01-20	Process for the preparation of a carbocyclic nucleoside analogue
DE69615591T2 (de)	2002-06-06	Verfahren zur Herstellung von Purinderivaten
EP0271834B1 (de)	1994-09-07	Verfahren zur Herstellung von Pyrimidinen
CA1260934A (en)	1989-09-26	Purine derivatives
DE69509182T2 (de)	1999-10-21	Herstellung N-9-substituierter Guanin-Verbindungen
US2705715A (en)	1955-04-05	Purine compounds and methods of preparing the same
PL102193B1 (pl)	1979-03-31	A process of producing new cyclic urethans
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DE1966640A1 (de)	1973-08-09	Verfahren zur herstellung von 4- und/ oder 4,6-substituierten pyrazolo (3,4-d)pyrimidinen
DE2822876C2 (pl)	1988-01-07
DD246301A5 (de)	1987-06-03	Verfahren zur herstellung von 9-(2-hydroxyaethoxy-methyl)granin
CA1117525A (en)	1982-02-02	2,3-polymethylene-4-oxo-4h-pyrido /1,2-a/ pyrimidines and process for the preparation thereof
EP0304004B1 (de)	1993-11-03	Verfahren zur Herstellung von Natriumpurinen
Eid et al.	1990	Reaction of some 1, 2, 4‐triazines with acetobromoglucose
DE69714971T2 (de)	2003-05-28	Verfahren zur herstellung von purin-derivaten
US3886176A (en)	1975-05-27	Process for preparing imidazole-4,5-dicarboxamide
CA2676162A1 (en)	2008-08-07	Method for producing ammonium hexafluorophosphates
US4286093A (en)	1981-08-25	9-Cyclohexyl-2-alkoxy-9H-adenine process
DE1943428C3 (de)	1979-02-08	Verfahren zur Herstellung von Pyrimidin- und 6-Azauracilnueleosiden
DE2117377C2 (de)	1983-08-25	6-(D-2,2-Dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)-penicillansäure-Derivate, Verfahren zu ihrer Herstellung und Verfahren zur Herstellung von 7-(D-&alpha;-Aminophenylacetamido)-3-methyl-3-cephem-4-carbonsäure
EP0690056A2 (de)	1996-01-03	Verfahren zur Herstellung von Purinen