NO130433B - - Google Patents
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- Publication number
- NO130433B NO130433B NO213671A NO213671A NO130433B NO 130433 B NO130433 B NO 130433B NO 213671 A NO213671 A NO 213671A NO 213671 A NO213671 A NO 213671A NO 130433 B NO130433 B NO 130433B
- Authority
- NO
- Norway
- Prior art keywords
- compound
- purine
- formula
- salts
- oxide
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- -1 purine compound Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- IQWJARHUKQVCCD-UHFFFAOYSA-N NC1=C2N=CN(C2=NC=[N+]1[O-])CC(C(O)C(=O)O)O Chemical compound NC1=C2N=CN(C2=NC=[N+]1[O-])CC(C(O)C(=O)O)O IQWJARHUKQVCCD-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000000871 hypocholesterolemic effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Fremgangsmåte for fremstilling av nye
terapeutisk aktive purinderivater.
Den foreliggende oppfinnelse angår en analogifremgangsmåte for fremstilling av en ny, terapeutisk aktiv purinforbindelse med formel og salter derav, og det særegne ved analogifremgangsmåten er at en forbindelse med den generelle formel
hvori R og R"*" hver står for hydrogen eller en lavere alkylgruppe med 1-3 karbonatomer, behandles med en sur substans eller en basisk substans i et vandig medium, eventuelt etterfulgt av omdannelse av det dannete produkt, hvis det oppnås i fri form, til et salt derav.
Som sur substans kan det f.eks. anvendes saltsyre, svovelsyre, maursyre, eddiksyre, benzoesyre eller lignende. Eksempler på basisk substans er natriumhydroksyd, kaliumhydroksyd, natrium-karbonat, kaliumkarbonat, natriummetoksyd, natriumetoksyd, kaliumetoksyd, etc. Det kan også benyttes en sur eller basisk ioneveksler-harpiks. Behandlingen utfores vanligvis ved en temperatur fra romtemperatur og opp til kokepunktstemperaturen for reaksjonsmediet.
Purinforbindelsen med formel I kan omdannes til salter derav, f.eks. metall-» ammonium-, amin- og syre-addisjonssalter på i og for seg kjent måte.
Purinforbindelsen med formel I og salter derav utover en markert hypokolesterolemisk aktivitet. Forbindelsene kan således anvendes som terapeutiske midler ved behandling av aterosklerose.
Eksempel.
6-amino-9-(3-karboksy-2,3-i sopropylidendioksy-propyl)-purin-1-oksyd (300 mg) suspenderes i 10% eddiksyre (10 ml). Suspensjonen oppvarmes under refluks i 30 minutter. En liten mengde aktivt kull tilsettes reaksjonsblandingen og den filtreres. Filtratet konsentreres under redusert trykk. Utfelte krystaller samles ved filtrering og omkrystailiseres fra vann og gir 6-amino-9-(3-karboksy-2,3-dihydroksypropyl)-purin-l-oksyd (165 mg). Smeltepunkt 275°C (spalting).
Utgangsforbindelsen, dvs. 6-amin-9-(3-karboksy-2,3-isopropyliden-dioksypropyl)-purin-1-oksyd, kan fremstilles på folgende måte: En suspensjon av adenin-1-oksyd (1,51 g), 2,3-isopropyliden-D-erytronolakton (2,21 g) og kaliumkarbonat (1,38 g) i dimetyl-formamid (50 ml) oppvarmes med omroring i 8 timer under tilbake-lop. Fra reaksjonsblandingen fjernes losningsmidlet ved destillasjon under redusert trykk. Resten loses i en liten mengde vann og filtreres. Filtratet justeres til pH 3 med 5% saltsyre. De utfelte krystaller samles ved filtrering og ga 6-amino-9-(3-karboksy-2,3-isopropylidendioksypropyl)-purin-l-oksyd (0,40 g). Smeltepunkt 270°C (spalting) (omkrystallisert fra metanol).
Claims (1)
- Analogifremgangsmåte for fremstilling av en ny, terapeutisk aktiv purin-forbindelse med formel:og salter derav, karakterisert ved at en forbindelse med den generelle formel: hvori R og R<1> hver står for hydrogen eller lavere alkyl med 1-3 karbonatomer, behandles med en sur substans eller en basisk substans i et vandig medium, eventuelt etterfulgt av omdannelse av det dannete produkt, hvis det oppnås i fri form, tilet salt derav.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3058469 | 1969-04-18 | ||
| JP3058569 | 1969-04-18 | ||
| JP3058369 | 1969-04-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO130433B true NO130433B (no) | 1974-09-02 |
Family
ID=27287019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO213671A NO130433B (no) | 1969-04-18 | 1971-06-07 |
Country Status (2)
| Country | Link |
|---|---|
| AT (1) | AT304570B (no) |
| NO (1) | NO130433B (no) |
-
1969
- 1969-08-27 AT AT518471A patent/AT304570B/de not_active IP Right Cessation
-
1971
- 1971-06-07 NO NO213671A patent/NO130433B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT304570B (de) | 1973-01-10 |
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