JPH0547546B2 - - Google Patents
Info
- Publication number
- JPH0547546B2 JPH0547546B2 JP88304288A JP30428888A JPH0547546B2 JP H0547546 B2 JPH0547546 B2 JP H0547546B2 JP 88304288 A JP88304288 A JP 88304288A JP 30428888 A JP30428888 A JP 30428888A JP H0547546 B2 JPH0547546 B2 JP H0547546B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- amino
- acetonitrile
- thiopurine
- formula
- 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.)
- Expired - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 claims description 20
- -1 2-acetoxyethoxymethyl group Chemical group 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 13
- XQPRBTXUXXVTKB-UHFFFAOYSA-M caesium iodide Chemical compound [I-].[Cs+] XQPRBTXUXXVTKB-UHFFFAOYSA-M 0.000 claims description 9
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
- XFEQOLXBMLXKDE-UHFFFAOYSA-N 2-(acetyloxymethoxy)ethyl acetate Chemical compound CC(=O)OCCOCOC(C)=O XFEQOLXBMLXKDE-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 claims description 3
- 229910052792 caesium Inorganic materials 0.000 claims description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- ARLSYSVVBAMYKA-UHFFFAOYSA-N 1,3-bis(phenylmethoxy)propan-2-ol Chemical compound C=1C=CC=CC=1COCC(O)COCC1=CC=CC=C1 ARLSYSVVBAMYKA-UHFFFAOYSA-N 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 54
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000002015 acyclic group Chemical group 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 239000002212 purine nucleoside Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 4
- 229930024421 Adenine Natural products 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229960000643 adenine Drugs 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- MRWXACSTFXYYMV-FDDDBJFASA-N nebularine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC=C2N=C1 MRWXACSTFXYYMV-FDDDBJFASA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 150000003212 purines Chemical class 0.000 description 3
- 238000006227 trimethylsilylation reaction Methods 0.000 description 3
- HDBQZGJWHMCXIL-UHFFFAOYSA-N 3,7-dihydropurine-2-thione Chemical class SC1=NC=C2NC=NC2=N1 HDBQZGJWHMCXIL-UHFFFAOYSA-N 0.000 description 2
- MSSXOMSJDRHRMC-UHFFFAOYSA-N 9H-purine-2,6-diamine Chemical compound NC1=NC(N)=C2NC=NC2=N1 MSSXOMSJDRHRMC-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 2
- 229960004150 aciclovir Drugs 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- DMHAXLGAKQREIL-UHFFFAOYSA-N 2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]ethyl acetate Chemical compound N1C(N)=NC(=O)C2=C1N(COCCOC(=O)C)C=N2 DMHAXLGAKQREIL-UHFFFAOYSA-N 0.000 description 1
- OEUMOLRKMKOLMX-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methoxy]ethyl acetate Chemical compound N1=CN=C2N(COCCOC(=O)C)C=NC2=C1N OEUMOLRKMKOLMX-UHFFFAOYSA-N 0.000 description 1
- RMRKSAOEJZMVHB-UHFFFAOYSA-N 2-amino-9-[1,3-bis(phenylmethoxy)propan-2-yloxymethyl]-3h-purin-6-one Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1COC(COCC=1C=CC=CC=1)COCC1=CC=CC=C1 RMRKSAOEJZMVHB-UHFFFAOYSA-N 0.000 description 1
- RTKMFQOHBDVEBC-UHFFFAOYSA-N 3-bromo-3-buten-1-ol Chemical compound OCCC(Br)=C RTKMFQOHBDVEBC-UHFFFAOYSA-N 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940075610 mercuric cyanide Drugs 0.000 description 1
- FQGYCXFLEQVDJQ-UHFFFAOYSA-N mercury dicyanide Chemical compound N#C[Hg]C#N FQGYCXFLEQVDJQ-UHFFFAOYSA-N 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019880013575A KR910000441B1 (ko) | 1988-10-18 | 1988-10-18 | 비고리 퓨린유도체의 제조방법 |
| KR13575/1988 | 1988-10-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02138184A JPH02138184A (ja) | 1990-05-28 |
| JPH0547546B2 true JPH0547546B2 (enrdf_load_stackoverflow) | 1993-07-19 |
Family
ID=19278569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP88304288A Granted JPH02138184A (ja) | 1988-10-18 | 1988-12-02 | 非環プリンヌクレオシドの製造方法 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPH02138184A (enrdf_load_stackoverflow) |
| KR (1) | KR910000441B1 (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100288054B1 (ko) * | 1993-05-10 | 2001-09-17 | 유현식 | 열화성폴리올레핀수지조성물과그의제조방법 |
| KR20030042572A (ko) * | 2001-11-23 | 2003-06-02 | 주식회사 그린메이드 | 생분해성 및 생붕괴성 수지 조성물 및 이를 이용한성형제품 |
| CN101289449A (zh) | 2007-04-20 | 2008-10-22 | 浙江医药股份有限公司新昌制药厂 | 2,6-二含氮取代的嘌呤衍生物及其制备方法和应用 |
-
1988
- 1988-10-18 KR KR1019880013575A patent/KR910000441B1/ko not_active Expired
- 1988-12-02 JP JP88304288A patent/JPH02138184A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| KR900006336A (ko) | 1990-05-07 |
| KR910000441B1 (ko) | 1991-01-25 |
| JPH02138184A (ja) | 1990-05-28 |
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