KR840005142A - 구아닌 유도체 및 그 제조방법 - Google Patents
구아닌 유도체 및 그 제조방법 Download PDFInfo
- Publication number
- KR840005142A KR840005142A KR1019830002778A KR830002778A KR840005142A KR 840005142 A KR840005142 A KR 840005142A KR 1019830002778 A KR1019830002778 A KR 1019830002778A KR 830002778 A KR830002778 A KR 830002778A KR 840005142 A KR840005142 A KR 840005142A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- formula
- protecting group
- hydrogen
- amino
- Prior art date
Links
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 title claims 7
- 238000002360 preparation method Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000006239 protecting group Chemical group 0.000 claims 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 4
- 229910052740 iodine Inorganic materials 0.000 claims 4
- 239000011630 iodine Substances 0.000 claims 4
- -1 nucleoside compound Chemical class 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 230000003287 optical effect Effects 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 3
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- MJGPTHPXMVMHPS-UHFFFAOYSA-N 1,3,2-dioxathietan-4-one Chemical compound O=C1OSO1 MJGPTHPXMVMHPS-UHFFFAOYSA-N 0.000 claims 1
- UKAHEJGSNVZSEY-UHFFFAOYSA-N 1-nitro-1-nitrosourea Chemical compound NC(=O)N(N=O)[N+]([O-])=O UKAHEJGSNVZSEY-UHFFFAOYSA-N 0.000 claims 1
- 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
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000006242 amine protecting group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000002777 nucleoside Substances 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 150000002926 oxygen Chemical class 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 238000007910 systemic administration Methods 0.000 claims 1
- 150000003568 thioethers Chemical class 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 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
- 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
- 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
- C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (5)
- 활성 성분인 일반식(I)의 화합물, 생리학적으로 허용되는 이의염 또는 이의 광학이성질체와 약학적으로 허용되는 담체로 구성된 제약 조성물.여기서, R1은 수소, 히드록시 또는 메르갑토임.
- 제1항에 있어서, 계통적 투여용으로 제조된 제약조성물.
- 제1항에 있어서, 국소투여용으로 제조된 제약조성물.
- 하기식(Ⅱ)의 너고리 측쇄화합물과 하기식(Ⅲ)의 N-9위치의 구아닌 유도체를 축합반응시켜 보호기를 제거시키거나. 하기식(Ⅳ)의 화합물을 치환반응시켜 보호기를 제거시키거나, 하기식(Ⅴ)의 화합물에서 에스페르기를 알콜기로 환원시켜 보호기를 제거시키거나, 하기식(Ⅵ)의 화합물을 고리닫힘 반응시켜 보호기를 제거시키거나, 하기식(Ⅶ)의 화합물을 고리닫힘 반응시켜 보호기를 제거시키거나, 하기식(Ⅷ)의 화합물의 피리미딘 링에서 치환반응시켜 보호기를 제거시키는 일반식(I)의 화합물, 생리학적으로 허용되는 이의 염, 또는 이의 광학이성질체 화합물의 제조방법.상기식에서, R1은 수소, 히드록시 또는 메르갑토이고; X는 염소, 불소, 요오드와 같은 기이거나, 혹은 OSO2R9(R9는 1-8탄소원자를 함유한 알킬, 1-3탄소원자를 함유한 플루오로화된 알킬, 아릴 또는 알킬아릴)이고; Y는 수소 또는 4차 암모늄 이온이고; R2및 는 R3함께 이중 결합된 산소 또는 열린 혹은 고리성케탈을 형성하는 알콕시이고; R4는 수소나 히드록실 보호기이고; R5는 상기의 R1과 같고; R4및 R5는 R1이 OH일때 함께 에폭사이드를 형성하거나 혹은 R4및 R5가 함께 카르보네이트 에스테르, 카르보네이트 티오에스테르나 이의오르토산 시클릭 또는 시클릭 아세탈형의 화합물과 같은 시클릭 유도체를 형성하고; R6은 히드록실, 염소, 불소, 요오드. 티올, 티오에테르, SO2R9(R9는 상기정의와 같다), 산소 유도체인 OR11(R11는 알킬, 벤젤과 같은 아릴알킬, 치환된 실릴, 포스포릴 디에스테르포스피노티오일이나 SO2R9임)이고; R7및 R8는 같거나 상이한테, 수소 또는 R10(R10은 아민보호기)이고 R12는 요오드 또는 OSO2R9이고; R13는 NH2또는 구아니딘이고; Z는 알콕시 또는 NH2이고; R14는 니트로소, 니트로, 아미노 포르믹아미드 또는 아미노 오르토에스테로이고, Hal은 플루오로, 클로로, 브로모 또는 요오드이고 R15는 히드록실 또는 아미노인테, R15가 아미노일때 아미노기는 히드록실 작용기로 변환가능함.필요하다면, 획득된 염기는 약학적으로 허용되는염으로 전환시키거나 획득된 염은 염기 또는 다른 약학적으로 허용되는 염으로 전환시킬 수 있고, 획득된 이성질치 혼합물은 순수한 거울상 이성질체로 분리 가능하다.
- 제4항에 있어서, R1이 수소인 9-(2-옥소-4-히드록시부틸)구아닌, R1이 히드록시인 9-(2-옥소-3,4-디히드록시부틱)구아닌, 또는 R1이 메르갑토인 9-(2-옥소-3-메르갑토-4-히드록시부틸)구아닌이나 혹은 생리학적으로 허용되는 이들의 염 또는 이들의 광학 이성질체 화합물의 제조 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8203856A SE8203856D0 (sv) | 1982-06-21 | 1982-06-21 | Novel derivatives of guanine ii |
| SE8203856-3 | 1982-06-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR840005142A true KR840005142A (ko) | 1984-11-03 |
Family
ID=20347138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830002778A KR840005142A (ko) | 1982-06-21 | 1983-06-21 | 구아닌 유도체 및 그 제조방법 |
Country Status (14)
| Country | Link |
|---|---|
| EP (2) | EP0103552B1 (ko) |
| JP (1) | JPS59501113A (ko) |
| KR (1) | KR840005142A (ko) |
| AT (1) | ATE19632T1 (ko) |
| DD (1) | DD210048A5 (ko) |
| DE (1) | DE3363376D1 (ko) |
| ES (1) | ES8501764A1 (ko) |
| GB (1) | GB2122197B (ko) |
| GR (1) | GR78622B (ko) |
| NZ (1) | NZ204641A (ko) |
| PT (1) | PT76903B (ko) |
| SE (1) | SE8203856D0 (ko) |
| WO (1) | WO1984000168A1 (ko) |
| ZA (1) | ZA834531B (ko) |
Families Citing this family (7)
| 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 |
| US4617304A (en) * | 1984-04-10 | 1986-10-14 | Merck & Co., Inc. | Purine derivatives |
| US4916225A (en) * | 1986-11-25 | 1990-04-10 | Institut Organicheskogo Sinteza Akademii Nauk Latviiskoi Ssr | 9-substituted guanines |
| US5216141A (en) * | 1988-06-06 | 1993-06-01 | Benner Steven A | Oligonucleotide analogs containing sulfur linkages |
| US5670506A (en) * | 1993-04-05 | 1997-09-23 | Cell Therapeutics, Inc. | Halogen, isothiocyanate or azide substituted xanthines |
| GB201220687D0 (en) * | 2012-11-16 | 2013-01-02 | Cross Mfg Co 1938 Ltd | Tuft forming apparatus |
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 SE8203856A patent/SE8203856D0/xx unknown
-
1983
- 1983-06-20 ES ES523426A patent/ES8501764A1/es not_active Expired
- 1983-06-20 GB GB08316742A patent/GB2122197B/en not_active Expired
- 1983-06-20 PT PT76903A patent/PT76903B/pt unknown
- 1983-06-20 EP EP83850171A patent/EP0103552B1/en not_active Expired
- 1983-06-20 AT AT83850171T patent/ATE19632T1/de not_active IP Right Cessation
- 1983-06-20 NZ NZ204641A patent/NZ204641A/en unknown
- 1983-06-20 JP JP58502215A patent/JPS59501113A/ja active Pending
- 1983-06-20 GR GR71723A patent/GR78622B/el unknown
- 1983-06-20 DE DE8383850171T patent/DE3363376D1/de not_active Expired
- 1983-06-20 WO PCT/SE1983/000255 patent/WO1984000168A1/en not_active Application Discontinuation
- 1983-06-20 EP EP83902142A patent/EP0112364A1/en active Pending
- 1983-06-21 ZA ZA834531A patent/ZA834531B/xx unknown
- 1983-06-21 KR KR1019830002778A patent/KR840005142A/ko not_active Application Discontinuation
- 1983-06-21 DD DD83252202A patent/DD210048A5/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0103552A3 (en) | 1984-06-13 |
| ES523426A0 (es) | 1984-12-01 |
| DE3363376D1 (en) | 1986-06-12 |
| EP0103552A2 (en) | 1984-03-21 |
| JPS59501113A (ja) | 1984-06-28 |
| ZA834531B (en) | 1984-03-28 |
| ES8501764A1 (es) | 1984-12-01 |
| SE8203856D0 (sv) | 1982-06-21 |
| PT76903A (en) | 1983-07-01 |
| GB8316742D0 (en) | 1983-07-20 |
| GB2122197B (en) | 1985-10-16 |
| EP0103552B1 (en) | 1986-05-07 |
| PT76903B (en) | 1986-04-09 |
| GR78622B (ko) | 1984-09-27 |
| NZ204641A (en) | 1985-10-11 |
| EP0112364A1 (en) | 1984-07-04 |
| GB2122197A (en) | 1984-01-11 |
| DD210048A5 (de) | 1984-05-30 |
| ATE19632T1 (de) | 1986-05-15 |
| WO1984000168A1 (en) | 1984-01-19 |
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