CH621789A5 - Process for the preparation of novel xanthine derivatives - Google Patents
Process for the preparation of novel xanthine derivatives Download PDFInfo
- Publication number
- CH621789A5 CH621789A5 CH210676A CH210676A CH621789A5 CH 621789 A5 CH621789 A5 CH 621789A5 CH 210676 A CH210676 A CH 210676A CH 210676 A CH210676 A CH 210676A CH 621789 A5 CH621789 A5 CH 621789A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- methyl
- compound
- preparation
- xanthine derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 9
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 title claims description 7
- 229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- -1 alkali metal salt Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 210000000748 cardiovascular system Anatomy 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- PNGZZTPRDWLIAA-UHFFFAOYSA-N 1-methyl-3-(2-methylpropyl)-7-(3-oxobutyl)purine-2,6-dione Chemical compound CN1C(=O)N(C=2N=CN(C2C1=O)CCC(C)=O)CC(C)C PNGZZTPRDWLIAA-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical compound [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-N 0.000 description 1
- APIXJSLKIYYUKG-UHFFFAOYSA-N 3 Isobutyl 1 methylxanthine Chemical compound O=C1N(C)C(=O)N(CC(C)C)C2=C1N=CN2 APIXJSLKIYYUKG-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229950009941 chloralose Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 230000009943 skeletal muscle blood flow Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752507555 DE2507555A1 (de) | 1975-02-21 | 1975-02-21 | 7-(oxoalkyl)-1,3-dialkylxanthine, verfahren zu ihrer herstellung und diese verbindung enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH621789A5 true CH621789A5 (en) | 1981-02-27 |
Family
ID=5939491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH210676A CH621789A5 (en) | 1975-02-21 | 1976-02-20 | Process for the preparation of novel xanthine derivatives |
Country Status (18)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0570831A2 (de) * | 1992-05-20 | 1993-11-24 | Hoechst Aktiengesellschaft | Verwendung von Xanthinderivaten zur Behandlung von Nervenschädigungen nach Unterbrechung der Blutzirkulation |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2761863A (en) * | 1956-09-04 | Lower-alkyl | ||
| DE932489C (de) * | 1953-09-11 | 1955-09-01 | Hoffmann La Roche | Verfahren zur Herstellung von neuen Xanthinbasen und deren Salzen |
| CH325292A (de) * | 1953-10-21 | 1957-10-31 | Geigy Ag J R | Verfahren zur Herstellung von 7-Oxyalkyl-xanthinderivaten |
| US3422107A (en) * | 1964-09-05 | 1969-01-14 | Albert Ag Chem Werke | Certain oxoalkyldimethylxanthines and a process for the preparation thereof |
| DE1233405B (de) * | 1964-09-05 | 1967-02-02 | Albert Ag Chem Werke | Verfahren zur Herstellung von 7-(Oxoalkyl)-1, 3-dimethylxanthinen |
| DE2234202A1 (de) * | 1972-07-12 | 1974-01-24 | Albert Ag Chem Werke | Verfahren zur herstellung von oxoalkylxanthinen |
| DE2330742C2 (de) * | 1973-06-16 | 1982-07-29 | Hoechst Ag, 6000 Frankfurt | 1-(Oxoalkyl)-3-methyl-7-alkylxanthine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| CH608236A5 (enrdf_load_stackoverflow) * | 1974-01-22 | 1978-12-29 | Wuelfing J A Fa |
-
1975
- 1975-02-21 DE DE19752507555 patent/DE2507555A1/de not_active Withdrawn
-
1976
- 1976-01-30 IE IE183/76A patent/IE43978B1/en unknown
- 1976-02-02 ZA ZA568A patent/ZA76568B/xx unknown
- 1976-02-09 FR FR7603413A patent/FR2301258A1/fr active Granted
- 1976-02-10 SE SE7601455A patent/SE7601455L/xx unknown
- 1976-02-10 AT AT89776A patent/AT342617B/de not_active IP Right Cessation
- 1976-02-11 BE BE164248A patent/BE838466A/xx not_active IP Right Cessation
- 1976-02-11 GB GB5326/76A patent/GB1496316A/en not_active Expired
- 1976-02-12 HU HU76WU22A patent/HU174656B/hu unknown
- 1976-02-13 AR AR262265A patent/AR208755A1/es active
- 1976-02-17 YU YU00372/76A patent/YU37276A/xx unknown
- 1976-02-18 NL NL7601622A patent/NL7601622A/xx not_active Application Discontinuation
- 1976-02-18 ES ES445301A patent/ES445301A1/es not_active Expired
- 1976-02-19 FI FI760418A patent/FI760418A7/fi not_active Application Discontinuation
- 1976-02-20 JP JP51017837A patent/JPS51110598A/ja active Pending
- 1976-02-20 DK DK72676*#A patent/DK72676A/da unknown
- 1976-02-20 CH CH210676A patent/CH621789A5/de not_active IP Right Cessation
- 1976-02-23 AU AU11338/76A patent/AU506542B2/en not_active Expired
- 1976-09-29 AR AR264907A patent/AR210168A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| AU1133876A (en) | 1977-09-01 |
| AR208755A1 (es) | 1977-02-28 |
| IE43978B1 (en) | 1981-07-15 |
| YU37276A (en) | 1982-08-31 |
| ATA89776A (de) | 1977-08-15 |
| FI760418A7 (enrdf_load_stackoverflow) | 1976-08-22 |
| ES445301A1 (es) | 1977-06-01 |
| DK72676A (da) | 1976-08-22 |
| AR210168A1 (es) | 1977-06-30 |
| FR2301258B1 (enrdf_load_stackoverflow) | 1978-11-17 |
| FR2301258A1 (fr) | 1976-09-17 |
| NL7601622A (nl) | 1976-08-24 |
| DE2507555A1 (de) | 1976-09-02 |
| BE838466A (fr) | 1976-08-11 |
| SE7601455L (sv) | 1976-08-22 |
| AT342617B (de) | 1978-04-10 |
| AU506542B2 (en) | 1980-01-10 |
| JPS51110598A (enrdf_load_stackoverflow) | 1976-09-30 |
| IE43978L (en) | 1976-08-21 |
| GB1496316A (en) | 1977-12-30 |
| ZA76568B (en) | 1977-01-26 |
| HU174656B (hu) | 1980-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |