DD210274A5 - Verfahren zur herstellung von guaninderivaten - Google Patents
Verfahren zur herstellung von guaninderivaten Download PDFInfo
- Publication number
- DD210274A5 DD210274A5 DD83252201A DD25220183A DD210274A5 DD 210274 A5 DD210274 A5 DD 210274A5 DD 83252201 A DD83252201 A DD 83252201A DD 25220183 A DD25220183 A DD 25220183A DD 210274 A5 DD210274 A5 DD 210274A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- group
- hydrogen atom
- atom
- methoxy
- fluorine atom
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 39
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 title claims description 26
- 230000008569 process Effects 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 71
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 48
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract description 20
- 230000003287 optical effect Effects 0.000 claims abstract description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 25
- -1 carbonate ester Chemical class 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 23
- 125000006239 protecting group Chemical group 0.000 claims description 12
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 239000011630 iodine Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 5
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- MJGPTHPXMVMHPS-UHFFFAOYSA-N 1,3,2-dioxathietan-4-one Chemical compound O=C1OSO1 MJGPTHPXMVMHPS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001923 cyclic compounds Chemical class 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- WJSVJNDMOQTICG-UHFFFAOYSA-N 2-amino-1-[(2-methyl-4-methylidene-5-oxooxolan-2-yl)methyl]-7h-purin-6-one Chemical compound NC1=NC=2N=CNC=2C(=O)N1CC1(C)CC(=C)C(=O)O1 WJSVJNDMOQTICG-UHFFFAOYSA-N 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 claims 1
- 150000002926 oxygen Chemical class 0.000 claims 1
- 125000000101 thioether group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 20
- 239000001257 hydrogen Substances 0.000 abstract description 18
- 238000011282 treatment Methods 0.000 abstract description 18
- 230000009385 viral infection Effects 0.000 abstract description 6
- 230000000840 anti-viral effect Effects 0.000 abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 2
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 35
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- 241000700605 Viruses Species 0.000 description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 10
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 229960005150 glycerol Drugs 0.000 description 6
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
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- RYYIULNRIVUMTQ-UHFFFAOYSA-N 6-chloroguanine Chemical compound NC1=NC(Cl)=C2N=CNC2=N1 RYYIULNRIVUMTQ-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/16—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8203855A SE8203855D0 (sv) | 1982-06-21 | 1982-06-21 | Novel derivatives of guanine i |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD210274A5 true DD210274A5 (de) | 1984-06-06 |
Family
ID=20347137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD83252201A DD210274A5 (de) | 1982-06-21 | 1983-06-21 | Verfahren zur herstellung von guaninderivaten |
Country Status (17)
| Country | Link |
|---|---|
| EP (2) | EP0112353A1 (es) |
| JP (1) | JPS59501112A (es) |
| KR (1) | KR840005141A (es) |
| AT (1) | ATE18225T1 (es) |
| AU (1) | AU1706083A (es) |
| DD (1) | DD210274A5 (es) |
| DE (1) | DE3362283D1 (es) |
| ES (1) | ES8500942A1 (es) |
| GB (1) | GB2122198B (es) |
| GR (1) | GR78621B (es) |
| IS (1) | IS2822A7 (es) |
| NZ (1) | NZ204640A (es) |
| PH (1) | PH19399A (es) |
| PT (1) | PT76902B (es) |
| SE (1) | SE8203855D0 (es) |
| WO (1) | WO1984000167A1 (es) |
| ZA (1) | ZA834532B (es) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5684153A (en) | 1984-08-16 | 1997-11-04 | Beecham Group Plc | Process for the preparation of purine derivatives |
| IL73682A (en) * | 1983-12-20 | 1991-08-16 | Medivir Ab | Antiviral pharmaceutical compositions containing 9-hydroxy aliphatic derivatives of guanine,some new such derivatives and process for their preparation |
| EP0152316B1 (en) * | 1984-01-26 | 1989-07-26 | Merck & Co. Inc. | Substituted butyl guanines and their utilization in antiviral compositions |
| US4617304A (en) * | 1984-04-10 | 1986-10-14 | Merck & Co., Inc. | Purine derivatives |
| KR870002141A (ko) * | 1985-08-16 | 1987-03-30 | 배리 안토니 뉴샘 | 구아닌 유도체의 제조 방법 및 이 유도체를 함유하는 제약 조성물 |
| DE3627024A1 (de) | 1985-09-24 | 1987-04-02 | Hoechst Ag | In 6- und 9-stellung substituierte 2-aminopurine, ihre verwendung, diese purine enthaltende arzneimittel und verfahren zur herstellung der purine |
| DE3604899A1 (de) * | 1986-02-17 | 1987-08-20 | Hoechst Ag | Chirale umsetzungsprodukte aus mesogenen molekuelbausteinen und bifunktionell reaktionsfaehigen butantetraolderivaten und ihre verwendung als dotierstoff in fluessigkristall-phasen |
| US4916225A (en) * | 1986-11-25 | 1990-04-10 | Institut Organicheskogo Sinteza Akademii Nauk Latviiskoi Ssr | 9-substituted guanines |
| US4973318A (en) * | 1988-02-10 | 1990-11-27 | D.C.P. Af 1988 A/S | Disposable syringe |
| US5216141A (en) * | 1988-06-06 | 1993-06-01 | Benner Steven A | Oligonucleotide analogs containing sulfur linkages |
| US4966895A (en) * | 1989-02-02 | 1990-10-30 | Merck & Co. Inc. | Cyclic monophosphates of purine and pyrimidine acyclonucleosides as anti-retroviral agents |
| CA2347973C (en) | 1999-07-20 | 2010-06-22 | Morphosys Ag | Novel methods for displaying (poly)peptides/proteins on bacteriophage particles via disulfide bonds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1523865A (en) * | 1974-09-02 | 1978-09-06 | Wellcome Found | Purine compunds and salts thereof |
| US4230708A (en) * | 1977-10-20 | 1980-10-28 | Stichting Rega V.Z.W. | Therapeutic application of (S) -or (RS)-9-(2, 3-dihydroxypropyl) adenine for use as antiviral agents |
| US4221910A (en) * | 1978-09-15 | 1980-09-09 | Newport Pharmaceuticals International, Inc. | 9-(Hydroxy alkyl)purines |
| IL64501A (en) * | 1980-12-22 | 1985-07-31 | Astra Laekemedel Ab | 9-substituted 4-hydroxybutyl guanine derivatives,their preparation and antiviral use |
-
1982
- 1982-06-21 SE SE8203855A patent/SE8203855D0/xx unknown
-
1983
- 1983-06-20 PT PT76902A patent/PT76902B/pt unknown
- 1983-06-20 GB GB08316743A patent/GB2122198B/en not_active Expired
- 1983-06-20 ES ES523425A patent/ES8500942A1/es not_active Expired
- 1983-06-20 AU AU17060/83A patent/AU1706083A/en not_active Abandoned
- 1983-06-20 JP JP58502135A patent/JPS59501112A/ja active Pending
- 1983-06-20 EP EP83901965A patent/EP0112353A1/en active Pending
- 1983-06-20 DE DE8383850170T patent/DE3362283D1/de not_active Expired
- 1983-06-20 NZ NZ204640A patent/NZ204640A/en unknown
- 1983-06-20 WO PCT/SE1983/000254 patent/WO1984000167A1/en not_active Application Discontinuation
- 1983-06-20 GR GR71722A patent/GR78621B/el unknown
- 1983-06-20 PH PH29089A patent/PH19399A/en unknown
- 1983-06-20 AT AT83850170T patent/ATE18225T1/de not_active IP Right Cessation
- 1983-06-20 EP EP83850170A patent/EP0103551B1/en not_active Expired
- 1983-06-21 DD DD83252201A patent/DD210274A5/de unknown
- 1983-06-21 KR KR1019830002777A patent/KR840005141A/ko not_active Application Discontinuation
- 1983-06-21 IS IS2822A patent/IS2822A7/is unknown
- 1983-06-21 ZA ZA834532A patent/ZA834532B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0103551B1 (en) | 1986-02-26 |
| ATE18225T1 (de) | 1986-03-15 |
| JPS59501112A (ja) | 1984-06-28 |
| SE8203855D0 (sv) | 1982-06-21 |
| GB2122198A (en) | 1984-01-11 |
| EP0103551A3 (en) | 1984-06-13 |
| EP0103551A2 (en) | 1984-03-21 |
| DE3362283D1 (en) | 1986-04-03 |
| GB2122198B (en) | 1985-11-06 |
| ES523425A0 (es) | 1984-11-01 |
| KR840005141A (ko) | 1984-11-03 |
| PT76902B (en) | 1986-04-09 |
| ES8500942A1 (es) | 1984-11-01 |
| WO1984000167A1 (en) | 1984-01-19 |
| GR78621B (es) | 1984-09-27 |
| ZA834532B (en) | 1984-03-28 |
| PT76902A (en) | 1983-07-01 |
| AU1706083A (en) | 1984-01-26 |
| NZ204640A (en) | 1986-07-11 |
| GB8316743D0 (en) | 1983-07-20 |
| PH19399A (en) | 1986-04-10 |
| EP0112353A1 (en) | 1984-07-04 |
| IS2822A7 (is) | 1986-02-28 |
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