DE2330742C2 - 1-(Oxoalkyl)-3-methyl-7-alkylxanthine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel - Google Patents
1-(Oxoalkyl)-3-methyl-7-alkylxanthine, Verfahren zu ihrer Herstellung und diese enthaltende ArzneimittelInfo
- Publication number
- DE2330742C2 DE2330742C2 DE2330742A DE2330742A DE2330742C2 DE 2330742 C2 DE2330742 C2 DE 2330742C2 DE 2330742 A DE2330742 A DE 2330742A DE 2330742 A DE2330742 A DE 2330742A DE 2330742 C2 DE2330742 C2 DE 2330742C2
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- oxoalkyl
- oxohexyl
- carbon atoms
- compounds
- 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
Links
- 238000000034 method Methods 0.000 title claims description 7
- 125000005188 oxoalkyl group Chemical group 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000003814 drug Substances 0.000 title description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000000304 vasodilatating effect Effects 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- -1 Alkali metal salts Chemical class 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- BYPFEZZEUUWMEJ-UHFFFAOYSA-N Pentoxifylline Chemical compound O=C1N(CCCCC(=O)C)C(=O)N(C)C2=C1N(C)C=N2 BYPFEZZEUUWMEJ-UHFFFAOYSA-N 0.000 description 3
- RBQOQRRFDPXAGN-UHFFFAOYSA-N Propentofylline Chemical compound CN1C(=O)N(CCCCC(C)=O)C(=O)C2=C1N=CN2CCC RBQOQRRFDPXAGN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- MHNVSFOURBQRPK-UHFFFAOYSA-N 3-methyl-7-propylpurine-2,6-dione Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2CCC MHNVSFOURBQRPK-UHFFFAOYSA-N 0.000 description 2
- SOCYNBJTSAFFQI-UHFFFAOYSA-N 7-butyl-3-methyl-1-(5-oxohexyl)purine-2,6-dione Chemical compound CN1C(=O)N(CCCCC(C)=O)C(=O)C2=C1N=CN2CCCC SOCYNBJTSAFFQI-UHFFFAOYSA-N 0.000 description 2
- ZEVSCOLPYKRVBZ-UHFFFAOYSA-N 7-decyl-3-methylpurine-2,6-dione Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2CCCCCCCCCC ZEVSCOLPYKRVBZ-UHFFFAOYSA-N 0.000 description 2
- SAEKTFXZAVNNEC-UHFFFAOYSA-N 7-hexyl-3-methyl-1-(5-oxohexyl)purine-2,6-dione Chemical compound CN1C(=O)N(CCCCC(C)=O)C(=O)C2=C1N=CN2CCCCCC SAEKTFXZAVNNEC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000251730 Chondrichthyes Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 230000003727 cerebral blood flow Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000008050 dialkyl sulfates Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- 229960001476 pentoxifylline Drugs 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- ARZOGANVDPBFCO-UHFFFAOYSA-N 3-methyl-1-(4-oxopentyl)-7-propylpurine-2,6-dione Chemical compound CN1C(=O)N(CCCC(C)=O)C(=O)C2=C1N=CN2CCC ARZOGANVDPBFCO-UHFFFAOYSA-N 0.000 description 1
- WQRASISGTROKJS-UHFFFAOYSA-N 3-methyl-1-(6-oxoheptyl)-7-propylpurine-2,6-dione Chemical compound CN1C(=O)N(CCCCCC(C)=O)C(=O)C2=C1N=CN2CCC WQRASISGTROKJS-UHFFFAOYSA-N 0.000 description 1
- AHSKYWGYRVWJLX-UHFFFAOYSA-N 3-methyl-7-(2-methylpropyl)-1-(5-oxohexyl)purine-2,6-dione Chemical compound CN1C(=O)N(CCCCC(C)=O)C(=O)C2=C1N=CN2CC(C)C AHSKYWGYRVWJLX-UHFFFAOYSA-N 0.000 description 1
- GEFSODPOIKXZRF-UHFFFAOYSA-N 3-methyl-7-(2-methylpropyl)purine-2,6-dione Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2CC(C)C GEFSODPOIKXZRF-UHFFFAOYSA-N 0.000 description 1
- QMUGICMOASIURD-UHFFFAOYSA-N 7-butyl-3-methylpurine-2,6-dione Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2CCCC QMUGICMOASIURD-UHFFFAOYSA-N 0.000 description 1
- RTYRGIMUXABCRT-UHFFFAOYSA-N 7-decyl-3-methyl-1-(5-oxohexyl)purine-2,6-dione Chemical compound CN1C(=O)N(CCCCC(C)=O)C(=O)C2=C1N=CN2CCCCCCCCCC RTYRGIMUXABCRT-UHFFFAOYSA-N 0.000 description 1
- MROQSUMVRJJJLI-UHFFFAOYSA-N 7-ethyl-3-methyl-1-(5-oxohexyl)purine-2,6-dione Chemical compound CN1C(=O)N(CCCCC(C)=O)C(=O)C2=C1N=CN2CC MROQSUMVRJJJLI-UHFFFAOYSA-N 0.000 description 1
- GISWGHGEIIOKGX-UHFFFAOYSA-N 7-ethyl-3-methylpurine-2,6-dione Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2CC GISWGHGEIIOKGX-UHFFFAOYSA-N 0.000 description 1
- XYNBLDBVMROPEH-UHFFFAOYSA-N 7-hexyl-3-methylpurine-2,6-dione Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2CCCCCC XYNBLDBVMROPEH-UHFFFAOYSA-N 0.000 description 1
- DEDHQVXKYCLMFM-UHFFFAOYSA-N 8-propyl-3,7-dihydropurine-2,6-dione Chemical compound N1C(=O)NC(=O)C2=C1N=C(CCC)N2 DEDHQVXKYCLMFM-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 1
- 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 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 102000014171 Milk Proteins Human genes 0.000 description 1
- 108010011756 Milk Proteins Proteins 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- CRJDECRJWVWVAZ-UHFFFAOYSA-N O=C(CCCCN1C(=O)N(C=2N=CN(C2C1=O)CC)C)C.CO Chemical compound O=C(CCCCN1C(=O)N(C=2N=CN(C2C1=O)CC)C)C.CO CRJDECRJWVWVAZ-UHFFFAOYSA-N 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000021239 milk protein Nutrition 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2330742A DE2330742C2 (de) | 1973-06-16 | 1973-06-16 | 1-(Oxoalkyl)-3-methyl-7-alkylxanthine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| AR254209A AR208179A1 (es) | 1973-06-16 | 1974-01-01 | Procedimiento para la produccion de (omega-1)-oxoalquildialquilxantinas |
| ES427171A ES427171A1 (es) | 1973-06-16 | 1974-06-11 | Procedimiento para la produccion de oxoalquil-dialquilxan- tinas. |
| NO742121A NO140300C (no) | 1973-06-16 | 1974-06-11 | Analogifremgangsmaate for fremstilling av terapeutisk aktive (omega-1)-oksodialkylxantiner |
| ZA00743760A ZA743760B (en) | 1973-06-16 | 1974-06-12 | Xanthine derivatives |
| NLAANVRAGE7407890,A NL182806C (nl) | 1973-06-16 | 1974-06-13 | Werkwijze ter bereiding van een geneesmiddel met doorbloedingsverbeterende en bronchospasmolytische werking, gevormd geneesmiddel en werkwijze ter bereiding van geneeskrachtige verbindingen. |
| DK321574A DK145676C (da) | 1973-06-16 | 1974-06-14 | Analogifremgangsmaade til fremstilling af oxoalkyldialkylxanthiner |
| CH748211A CH608807A5 (enExample) | 1973-06-16 | 1974-06-14 | |
| FI1819/74A FI58920C (fi) | 1973-06-16 | 1974-06-14 | Foerfarande foer framstaellning av blodkaerlsutvidgande (omega-1)-oxoalkyl-dialkylxantiner |
| FR7420679A FR2233065B1 (enExample) | 1973-06-16 | 1974-06-14 | |
| SE7407913A SE423631B (sv) | 1973-06-16 | 1974-06-14 | Forfarande for framstellning av oxaalhyl-dialkylxantiner |
| GB2655574A GB1470220A (en) | 1973-06-16 | 1974-06-14 | 1-or 7-oxoalkyl xanthine derivatives |
| IE1258/74A IE39898B1 (en) | 1973-06-16 | 1974-06-14 | 1-or 7-oxoalkyl xanthine derivatives |
| CH123978A CH612969A5 (enExample) | 1973-06-16 | 1974-06-14 | |
| BE145417A BE816332A (fr) | 1973-06-16 | 1974-06-14 | Medicament utile notamment comme vasodilatateur, procede de preparation de ses substances actives et ces substances elles-memes. |
| AT491874A AT334388B (de) | 1973-06-16 | 1974-06-14 | Verfahren zur herstellung von neuen 1- oder 7-(omega-1)-oxoalkyl-3,7 (oder 1,3)-dialkylxanthinen |
| JP49067265A JPS5233120B2 (enExample) | 1973-06-16 | 1974-06-14 | |
| AU70147/74A AU484900B2 (en) | 1973-06-16 | 1974-06-18 | Xanthine derivatives |
| AR260113A AR209320A1 (es) | 1973-06-16 | 1975-08-22 | Procedimiento para la produccion de (omega-1)-oxoalquildialquilxantinas |
| AR260112A AR209319A1 (es) | 1973-06-16 | 1975-08-22 | Procedimiento para la produccion de (omega-1)-oxo-alquil-dialquilxantinas |
| AT738975A AT334392B (de) | 1973-06-16 | 1975-09-26 | Verfahren zur herstellung von neuen 1- oder 7-(omega-1)-oxoalkyl-3,7 (oder 1,3-)-dialkylxanthinen |
| AT738875A AT334391B (de) | 1973-06-16 | 1975-09-26 | Verfahren zur herstellung von neuen 1- oder 7-(omega-1)-oxoalkyl-3,7-(oder 1,3-)dialkylxanthinen |
| US06/032,536 US4289776A (en) | 1973-06-16 | 1979-04-23 | Xanthine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2330742A DE2330742C2 (de) | 1973-06-16 | 1973-06-16 | 1-(Oxoalkyl)-3-methyl-7-alkylxanthine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2330742A1 DE2330742A1 (de) | 1975-01-09 |
| DE2330742C2 true DE2330742C2 (de) | 1982-07-29 |
Family
ID=5884209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2330742A Expired DE2330742C2 (de) | 1973-06-16 | 1973-06-16 | 1-(Oxoalkyl)-3-methyl-7-alkylxanthine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4289776A (enExample) |
| JP (1) | JPS5233120B2 (enExample) |
| AR (3) | AR208179A1 (enExample) |
| AT (1) | AT334388B (enExample) |
| BE (1) | BE816332A (enExample) |
| CH (2) | CH608807A5 (enExample) |
| DE (1) | DE2330742C2 (enExample) |
| DK (1) | DK145676C (enExample) |
| ES (1) | ES427171A1 (enExample) |
| FI (1) | FI58920C (enExample) |
| FR (1) | FR2233065B1 (enExample) |
| GB (1) | GB1470220A (enExample) |
| IE (1) | IE39898B1 (enExample) |
| NL (1) | NL182806C (enExample) |
| NO (1) | NO140300C (enExample) |
| SE (1) | SE423631B (enExample) |
| ZA (1) | ZA743760B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4372959A (en) | 1980-06-21 | 1983-02-08 | Beecham-Wulfing Gmbh & Co. Kg | 1-(5-Oxohexyl)-3-alkyl-7-(2-oxopropyl)xanthines |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH608236A5 (enExample) * | 1974-01-22 | 1978-12-29 | Wuelfing J A Fa | |
| DE2507554A1 (de) * | 1975-02-21 | 1976-09-02 | Wuelfing J A Fa | 7-(oxoalkyl)-1,3-dialkylxanthine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE2507555A1 (de) * | 1975-02-21 | 1976-09-02 | Wuelfing J A Fa | 7-(oxoalkyl)-1,3-dialkylxanthine, verfahren zu ihrer herstellung und diese verbindung enthaltende arzneimittel |
| JPS54112893A (en) * | 1978-02-21 | 1979-09-04 | Kohjin Co Ltd | Preparation of 1-(5'-oxohexyl)-3,7-diethylxanthine |
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| JP2549480B2 (ja) * | 1991-12-10 | 1996-10-30 | ヘキストジャパン株式会社 | 排尿障害改善剤 |
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| US5670506A (en) * | 1993-04-05 | 1997-09-23 | Cell Therapeutics, Inc. | Halogen, isothiocyanate or azide substituted xanthines |
| US6020337A (en) * | 1993-04-05 | 2000-02-01 | Cell Therapeutics, Inc. | Electronegative-substituted long chain xanthine compounds |
| AU1868195A (en) * | 1994-01-28 | 1995-08-15 | Cell Therapeutics, Inc. | Cell signaling inhibitors |
| US5762953A (en) * | 1996-08-22 | 1998-06-09 | Theratech, Inc. | Transdermal propentofylline compositions for the treatment of Alzheimers disease |
| DE19707655A1 (de) * | 1997-02-26 | 1998-08-27 | Hoechst Ag | Kombinationspräparat zur Anwendung bei Demenz |
| US20040110776A1 (en) * | 2002-02-22 | 2004-06-10 | Iok-Hou Pang | Use of propentofylline to control intraocular pressure |
| BRPI0908107A2 (pt) | 2008-02-29 | 2019-09-24 | Concert Pharmaceuticals Inc | composto derivado de xantina substituída, composição farmacêutica que compreende esse composto, métodos de tratamento de uma enfermidade ou condição em um paciente com necessidade do mesmo, método de tratamento de enfermidade crônica dos rins, do fígado, relacionada com diabetes e de claudicação intermitente |
| US20110053961A1 (en) | 2009-02-27 | 2011-03-03 | Concert Pharmaceuticals, Inc. | Substituted xanthine derivatives |
| IN2012DN01642A (enExample) | 2009-09-02 | 2015-06-05 | Concert Pharmaceuticals Inc | |
| WO2017114843A1 (en) * | 2015-12-29 | 2017-07-06 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Xanthine derivative inhibitors of bet proteins |
| CN112724160A (zh) * | 2021-03-19 | 2021-04-30 | 赤峰经方医药技术开发有限责任公司 | 一种己酮可可碱杂质的制备方法 |
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| US3864469A (en) * | 1967-12-16 | 1975-02-04 | Hoechst Ag | Xanthines in pharmaceutical preparations and for stabilization of vitamins |
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1973
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1974
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- 1974-06-11 ES ES427171A patent/ES427171A1/es not_active Expired
- 1974-06-11 NO NO742121A patent/NO140300C/no unknown
- 1974-06-12 ZA ZA00743760A patent/ZA743760B/xx unknown
- 1974-06-13 NL NLAANVRAGE7407890,A patent/NL182806C/xx not_active IP Right Cessation
- 1974-06-14 FR FR7420679A patent/FR2233065B1/fr not_active Expired
- 1974-06-14 DK DK321574A patent/DK145676C/da active
- 1974-06-14 SE SE7407913A patent/SE423631B/xx not_active IP Right Cessation
- 1974-06-14 AT AT491874A patent/AT334388B/de not_active IP Right Cessation
- 1974-06-14 BE BE145417A patent/BE816332A/xx not_active IP Right Cessation
- 1974-06-14 GB GB2655574A patent/GB1470220A/en not_active Expired
- 1974-06-14 IE IE1258/74A patent/IE39898B1/xx unknown
- 1974-06-14 FI FI1819/74A patent/FI58920C/fi active
- 1974-06-14 JP JP49067265A patent/JPS5233120B2/ja not_active Expired
- 1974-06-14 CH CH748211A patent/CH608807A5/xx not_active IP Right Cessation
- 1974-06-14 CH CH123978A patent/CH612969A5/xx not_active IP Right Cessation
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1975
- 1975-08-22 AR AR260113A patent/AR209320A1/es active
- 1975-08-22 AR AR260112A patent/AR209319A1/es active
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1979
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