JPS5813394A - １−β−Ｄ−リボフラノシル−４，５−置換イミダゾ−ルの製造法 - Google Patents
１−β−Ｄ−リボフラノシル−４，５−置換イミダゾ−ルの製造法Info
- Publication number
- JPS5813394A JPS5813394A JP11171481A JP11171481A JPS5813394A JP S5813394 A JPS5813394 A JP S5813394A JP 11171481 A JP11171481 A JP 11171481A JP 11171481 A JP11171481 A JP 11171481A JP S5813394 A JPS5813394 A JP S5813394A
- Authority
- JP
- Japan
- Prior art keywords
- imidazole
- substituted
- ribofuranosyl
- genus
- beta
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 244000005700 microbiome Species 0.000 claims abstract description 16
- OQRXBXNATIHDQO-UHFFFAOYSA-N 6-chloropyridine-3,4-diamine Chemical compound NC1=CN=C(Cl)C=C1N OQRXBXNATIHDQO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 102100036286 Purine nucleoside phosphorylase Human genes 0.000 claims abstract description 12
- 108010009099 nucleoside phosphorylase Proteins 0.000 claims abstract description 12
- 150000002460 imidazoles Chemical class 0.000 claims abstract description 10
- 239000002773 nucleotide Substances 0.000 claims abstract description 9
- 125000003729 nucleotide group Chemical group 0.000 claims abstract description 9
- 239000002777 nucleoside Substances 0.000 claims abstract description 8
- 150000003833 nucleoside derivatives Chemical class 0.000 claims abstract description 6
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- 230000000813 microbial effect Effects 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 abstract description 5
- 241000589565 Flavobacterium Species 0.000 abstract description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 2
- 150000003016 phosphoric acids Chemical class 0.000 abstract 2
- 241000589539 Brevundimonas diminuta Species 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 18
- 230000001580 bacterial effect Effects 0.000 description 16
- 239000000243 solution Substances 0.000 description 13
- 102000004190 Enzymes Human genes 0.000 description 9
- 108090000790 Enzymes Proteins 0.000 description 9
- 229940088598 enzyme Drugs 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 241000590020 Achromobacter Species 0.000 description 4
- 241000186146 Brevibacterium Species 0.000 description 4
- 241000186321 Cellulomonas Species 0.000 description 4
- 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 4
- 230000000694 effects Effects 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- -1 5-substituted imidazoles Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241000186063 Arthrobacter Species 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 3
- 101710101148 Probable 6-oxopurine nucleoside phosphorylase Proteins 0.000 description 3
- 102000030764 Purine-nucleoside phosphorylase Human genes 0.000 description 3
- 241000607142 Salmonella Species 0.000 description 3
- 241000191940 Staphylococcus Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000607598 Vibrio Species 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 229940023064 escherichia coli Drugs 0.000 description 3
- 229940049964 oleate Drugs 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- 241000607534 Aeromonas Species 0.000 description 2
- 241000588986 Alcaligenes Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241000588914 Enterobacter Species 0.000 description 2
- UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 description 2
- 229930010555 Inosine Natural products 0.000 description 2
- 201000008225 Klebsiella pneumonia Diseases 0.000 description 2
- 241000588747 Klebsiella pneumoniae Species 0.000 description 2
- 241000721603 Mycoplana Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 102000009097 Phosphorylases Human genes 0.000 description 2
- 108010073135 Phosphorylases Proteins 0.000 description 2
- 206010035717 Pneumonia klebsiella Diseases 0.000 description 2
- 241000588767 Proteus vulgaris Species 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- 241000607720 Serratia Species 0.000 description 2
- DJJCXFVJDGTHFX-UHFFFAOYSA-N Uridinemonophosphate Natural products OC1C(O)C(COP(O)(O)=O)OC1N1C(=O)NC(=O)C=C1 DJJCXFVJDGTHFX-UHFFFAOYSA-N 0.000 description 2
- FOGRQMPFHUHIGU-UHFFFAOYSA-N Uridylic acid Natural products OC1C(OP(O)(O)=O)C(CO)OC1N1C(=O)NC(=O)C=C1 FOGRQMPFHUHIGU-UHFFFAOYSA-N 0.000 description 2
- 241000589634 Xanthomonas Species 0.000 description 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 2
- 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 2
- 239000006285 cell suspension Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229960003786 inosine Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000003835 nucleoside group Chemical class 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 229940007042 proteus vulgaris Drugs 0.000 description 2
- 239000002212 purine nucleoside Substances 0.000 description 2
- 239000002718 pyrimidine nucleoside Substances 0.000 description 2
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 2
- 229940045145 uridine Drugs 0.000 description 2
- DJJCXFVJDGTHFX-XVFCMESISA-N uridine 5'-monophosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(O)=O)O[C@H]1N1C(=O)NC(=O)C=C1 DJJCXFVJDGTHFX-XVFCMESISA-N 0.000 description 2
- AUHDWARTFSKSAC-HEIFUQTGSA-N (2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-(6-oxo-1H-purin-9-yl)oxolane-2-carboxylic acid Chemical compound [C@]1([C@H](O)[C@H](O)[C@@H](CO)O1)(N1C=NC=2C(O)=NC=NC12)C(=O)O AUHDWARTFSKSAC-HEIFUQTGSA-N 0.000 description 1
- UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 description 1
- WFIYPADYPQQLNN-UHFFFAOYSA-N 2-[2-(4-bromopyrazol-1-yl)ethyl]isoindole-1,3-dione Chemical compound C1=C(Br)C=NN1CCN1C(=O)C2=CC=CC=C2C1=O WFIYPADYPQQLNN-UHFFFAOYSA-N 0.000 description 1
- UEWSIIBPZOBMBL-UHFFFAOYSA-N 5-hydroxyimidazole-4-carboxamide Chemical compound NC(=O)C1=C([O-])[NH2+]C=N1 UEWSIIBPZOBMBL-UHFFFAOYSA-N 0.000 description 1
- 241000193764 Brevibacillus brevis Species 0.000 description 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000222178 Candida tropicalis Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001464977 Clavibacter michiganensis subsp. michiganensis Species 0.000 description 1
- 241000186216 Corynebacterium Species 0.000 description 1
- UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 description 1
- 241000588697 Enterobacter cloacae Species 0.000 description 1
- 241000588698 Erwinia Species 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- GRSZFWQUAKGDAV-UHFFFAOYSA-N Inosinic acid Natural products OC1C(O)C(COP(O)(O)=O)OC1N1C(NC=NC2=O)=C2N=C1 GRSZFWQUAKGDAV-UHFFFAOYSA-N 0.000 description 1
- 241000186809 Kurthia Species 0.000 description 1
- 241001637564 Kurtia Species 0.000 description 1
- 241000108056 Monas Species 0.000 description 1
- 102000016943 Muramidase Human genes 0.000 description 1
- 108010014251 Muramidase Proteins 0.000 description 1
- 241001135976 Mycoplana dimorpha Species 0.000 description 1
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 1
- 241000588912 Pantoea agglomerans Species 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- UJVJGYQUOOQTAW-UHFFFAOYSA-N Pyrimine Natural products OC(=O)C1CCC(C=2N=CC=CC=2)=N1 UJVJGYQUOOQTAW-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- 241000277263 Salmo Species 0.000 description 1
- 241000607715 Serratia marcescens Species 0.000 description 1
- 241000186652 Sporosarcina ureae Species 0.000 description 1
- 102000006405 Uridine phosphorylase Human genes 0.000 description 1
- 108010019092 Uridine phosphorylase Proteins 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 229960005305 adenosine Drugs 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940119563 enterobacter cloacae Drugs 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- RQFCJASXJCIDSX-UUOKFMHZSA-N guanosine 5'-monophosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O RQFCJASXJCIDSX-UUOKFMHZSA-N 0.000 description 1
- 235000013928 guanylic acid Nutrition 0.000 description 1
- 239000004226 guanylic acid Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 235000013902 inosinic acid Nutrition 0.000 description 1
- 239000004245 inosinic acid Substances 0.000 description 1
- 229940028843 inosinic acid Drugs 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 229960000274 lysozyme Drugs 0.000 description 1
- 235000010335 lysozyme Nutrition 0.000 description 1
- 239000004325 lysozyme Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002213 purine nucleotide Substances 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 239000002719 pyrimidine nucleotide Substances 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000008223 ribosides Chemical class 0.000 description 1
- 229940081969 saccharomyces cerevisiae Drugs 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11171481A JPS5813394A (ja) | 1981-07-17 | 1981-07-17 | １−β−Ｄ−リボフラノシル−４，５−置換イミダゾ−ルの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11171481A JPS5813394A (ja) | 1981-07-17 | 1981-07-17 | １−β−Ｄ−リボフラノシル−４，５−置換イミダゾ−ルの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5813394A true JPS5813394A (ja) | 1983-01-25 |
| JPH0365957B2 JPH0365957B2 (enrdf_load_stackoverflow) | 1991-10-15 |
Family
ID=14568292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11171481A Granted JPS5813394A (ja) | 1981-07-17 | 1981-07-17 | １−β−Ｄ−リボフラノシル−４，５−置換イミダゾ−ルの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5813394A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5216142A (en) * | 1989-04-17 | 1993-06-01 | Efamol Holdings Plc | Anti-virals |
-
1981
- 1981-07-17 JP JP11171481A patent/JPS5813394A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5216142A (en) * | 1989-04-17 | 1993-06-01 | Efamol Holdings Plc | Anti-virals |
| EP0693498A1 (en) * | 1989-04-17 | 1996-01-24 | Scotia Holdings Plc | Antiviral compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0365957B2 (enrdf_load_stackoverflow) | 1991-10-15 |
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