DE2460929A1 - Neue xanthinderivate, verfahren zu ihrer herstellung und ihre anwendung - Google Patents
Neue xanthinderivate, verfahren zu ihrer herstellung und ihre anwendungInfo
- Publication number
- DE2460929A1 DE2460929A1 DE19742460929 DE2460929A DE2460929A1 DE 2460929 A1 DE2460929 A1 DE 2460929A1 DE 19742460929 DE19742460929 DE 19742460929 DE 2460929 A DE2460929 A DE 2460929A DE 2460929 A1 DE2460929 A1 DE 2460929A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- ethyl
- general formula
- propyl
- 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.)
- Granted
Links
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- -1 2-hydroxypropyl group Chemical group 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 229940075420 xanthine Drugs 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 241000251730 Chondrichthyes Species 0.000 claims description 3
- 229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 claims description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 230000017531 blood circulation Effects 0.000 claims description 2
- 230000003727 cerebral blood flow Effects 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 4
- 239000000126 substance Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229960000278 theophylline Drugs 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 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 7
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 6
- 229920002261 Corn starch Polymers 0.000 description 5
- 239000008120 corn starch Substances 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 229940095064 tartrate Drugs 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- 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 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 229960004559 theobromine Drugs 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- KZJZFASNIFVLSP-UHFFFAOYSA-N 7-[2-[bis[2-hydroxy-3-(2-phenylmethoxyphenoxy)propyl]amino]ethyl]-1,3-dimethylpurine-2,6-dione Chemical compound C1=2C(=O)N(C)C(=O)N(C)C=2N=CN1CCN(CC(O)COC=1C(=CC=CC=1)OCC=1C=CC=CC=1)CC(O)COC1=CC=CC=C1OCC1=CC=CC=C1 KZJZFASNIFVLSP-UHFFFAOYSA-N 0.000 description 1
- ZTABYENLMDQXOF-UHFFFAOYSA-N 7-[2-hydroxy-3-[[2-hydroxy-3-(2-phenylmethoxyphenoxy)propyl]-methylamino]propyl]-1,3-dimethylpurine-2,6-dione;hydrochloride Chemical compound Cl.C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CC(O)CN(C)CC(O)COC1=CC=CC=C1OCC1=CC=CC=C1 ZTABYENLMDQXOF-UHFFFAOYSA-N 0.000 description 1
- GPKSGFNPIZESBZ-UHFFFAOYSA-N 7-[3-[butyl-[2-hydroxy-3-(2-phenylmethoxyphenoxy)propyl]amino]propyl]-1,3-dimethylpurine-2,6-dione 2,3-dihydroxybutanedioic acid Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(CCCC)CC(O)COC1=CC=CC=C1OCC1=CC=CC=C1 GPKSGFNPIZESBZ-UHFFFAOYSA-N 0.000 description 1
- BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 description 1
- DOYYRHKIBSHBDP-UHFFFAOYSA-N 8,8-diethyl-3H-purine-2,6-dione Chemical compound C(C)C1(N=C2NC(NC(C2=N1)=O)=O)CC DOYYRHKIBSHBDP-UHFFFAOYSA-N 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexamethylene diamine Natural products NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- QXUAFCKBYYPTPQ-ZWKAXHIPSA-L magnesium (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol octadecanoate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O QXUAFCKBYYPTPQ-ZWKAXHIPSA-L 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 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
- C07D473/10—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 with methyl radicals in positions 3 and 7, e.g. theobromine
-
- 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
-
- 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
- C07D473/08—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 with methyl radicals in positions 1 and 3, e.g. theophylline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (33)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742460929 DE2460929A1 (de) | 1974-12-21 | 1974-12-21 | Neue xanthinderivate, verfahren zu ihrer herstellung und ihre anwendung |
| AT904575A AT341540B (de) | 1974-12-21 | 1975-11-28 | Verfahren zur herstellung von neuen 1,3-dialkyl-7-aminoalkylxanthinen |
| LU73972A LU73972A1 (en, 2012) | 1974-12-21 | 1975-12-09 | |
| SU752197999A SU603340A3 (ru) | 1974-12-21 | 1975-12-11 | Способ получени производных ксантина или их солей |
| DD190116A DD124984A5 (en, 2012) | 1974-12-21 | 1975-12-12 | |
| AU87547/75A AU501889B2 (en) | 1974-12-21 | 1975-12-15 | Xanthine derivatives |
| DK571875A DK137677C (da) | 1974-12-21 | 1975-12-16 | Analogifremgangsmaade til fremstilling af basisk substitueredexanthinderivater eller syreadditionssalte heraf |
| FI753543A FI62089C (fi) | 1974-12-21 | 1975-12-16 | Foerfarande foer framstaellning av pao det perifera blodomloppet verkande 7-(n-(3-fenoxi-2-hydroxipropyl)-n-amino)-1,3-dialkyl-xantinderivat |
| US05/641,550 US3998953A (en) | 1974-12-21 | 1975-12-17 | 1,3,7-Trisubstitued xanthine peripheral vasodilators |
| GR49628A GR59204B (en) | 1974-12-21 | 1975-12-17 | New xanthin derivatives and method for their preparation and use |
| CS758669A CS191289B2 (en) | 1974-12-21 | 1975-12-18 | Method of producing 7-substituted 1,3-dialkyl-xanthines |
| CH1643275A CH628346A5 (de) | 1974-12-21 | 1975-12-18 | Verfahren zur herstellung neuer xanthinderivate. |
| RO7584245A RO68381A (ro) | 1974-12-21 | 1975-12-18 | Procedeu pentru prepararea unor noi derivati ai xantinei |
| YU03234/75A YU39004B (en) | 1974-12-21 | 1975-12-18 | Process for preparing new xanthine derivatives |
| IE2787/75A IE43208B1 (en) | 1974-12-21 | 1975-12-19 | Xanthine derivatives |
| HU75BO1590A HU174673B (hu) | 1974-12-21 | 1975-12-19 | Sposob poluchenija novykh proizvodnykh ksantina |
| BG032887A BG25518A3 (bg) | 1974-12-21 | 1975-12-19 | Метод за получаване на ксантинови производни |
| BE162965A BE836898A (fr) | 1974-12-21 | 1975-12-19 | Nouveaux derives de la xanthine, leur procede de preparation et leur utilisation |
| NZ179599A NZ179599A (en) | 1974-12-21 | 1975-12-19 | Xanthine derivatives, and pharmaceutical compositions containing such |
| FR7539174A FR2294706A1 (fr) | 1974-12-21 | 1975-12-19 | Nouveaux derives de la xanthine, leur procede de preparation et leur utilisation |
| ZA757865A ZA757865B (en) | 1974-12-21 | 1975-12-19 | Improvements relating to xanthine derivatives |
| GB52168/75A GB1517710A (en) | 1974-12-21 | 1975-12-19 | Xanthine derivatives |
| NL7514837A NL7514837A (nl) | 1974-12-21 | 1975-12-19 | Werkwijze ter bereiding van nieuwe xanthinederi- vaten en van preparaten, die deze xanthinederi- vaten bevatten. |
| SE7514477A SE420493B (sv) | 1974-12-21 | 1975-12-19 | Forfarande for framstellning av nya xantinderivat |
| JP50151721A JPS5188995A (en, 2012) | 1974-12-21 | 1975-12-19 | |
| PH17894A PH11810A (en) | 1974-12-21 | 1975-12-19 | 1,3,7-trisubstituted xanthine peripheral vasodilators |
| IL48697A IL48697A (en) | 1974-12-21 | 1975-12-19 | 1,3,7-trisubstituted xanthine derivatives,their preparatioand pharmaceutical compositions containing them |
| CA242,131A CA1036159A (en) | 1974-12-21 | 1975-12-19 | Xanthine derivatives, process for production and use thereof |
| NO754317A NO144928C (no) | 1974-12-21 | 1975-12-19 | Analogifremgangsmaate for fremstilling av fysiologisk aktive zantinderivater. |
| ES443738A ES443738A1 (es) | 1974-12-21 | 1975-12-20 | Procedimiento para la preparacion de nuevos derivados de xantina. |
| PL1975185740A PL99165B1 (pl) | 1974-12-21 | 1975-12-20 | Sposob wytwarzania nowych pochodnych ksantyny |
| ES451457A ES451457A1 (es) | 1974-12-21 | 1976-09-11 | Procedimiento para la preparacion de nuevos derivados de xantina. |
| DK123677A DK138455C (da) | 1974-12-21 | 1977-03-21 | Analogifremgangsmaade til fremstilling af basisk substitueredexanthinderivater eller syreadditionssalte heraf |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742460929 DE2460929A1 (de) | 1974-12-21 | 1974-12-21 | Neue xanthinderivate, verfahren zu ihrer herstellung und ihre anwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2460929A1 true DE2460929A1 (de) | 1976-06-24 |
| DE2460929C2 DE2460929C2 (en, 2012) | 1987-12-17 |
Family
ID=5934312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742460929 Granted DE2460929A1 (de) | 1974-12-21 | 1974-12-21 | Neue xanthinderivate, verfahren zu ihrer herstellung und ihre anwendung |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US3998953A (en, 2012) |
| JP (1) | JPS5188995A (en, 2012) |
| AT (1) | AT341540B (en, 2012) |
| AU (1) | AU501889B2 (en, 2012) |
| BE (1) | BE836898A (en, 2012) |
| BG (1) | BG25518A3 (en, 2012) |
| CA (1) | CA1036159A (en, 2012) |
| CH (1) | CH628346A5 (en, 2012) |
| CS (1) | CS191289B2 (en, 2012) |
| DD (1) | DD124984A5 (en, 2012) |
| DE (1) | DE2460929A1 (en, 2012) |
| DK (1) | DK137677C (en, 2012) |
| ES (2) | ES443738A1 (en, 2012) |
| FI (1) | FI62089C (en, 2012) |
| FR (1) | FR2294706A1 (en, 2012) |
| GB (1) | GB1517710A (en, 2012) |
| GR (1) | GR59204B (en, 2012) |
| HU (1) | HU174673B (en, 2012) |
| IE (1) | IE43208B1 (en, 2012) |
| IL (1) | IL48697A (en, 2012) |
| LU (1) | LU73972A1 (en, 2012) |
| NL (1) | NL7514837A (en, 2012) |
| NO (1) | NO144928C (en, 2012) |
| NZ (1) | NZ179599A (en, 2012) |
| PH (1) | PH11810A (en, 2012) |
| PL (1) | PL99165B1 (en, 2012) |
| RO (1) | RO68381A (en, 2012) |
| SE (1) | SE420493B (en, 2012) |
| SU (1) | SU603340A3 (en, 2012) |
| YU (1) | YU39004B (en, 2012) |
| ZA (1) | ZA757865B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4337254A (en) * | 1977-08-23 | 1982-06-29 | Burroughs Wellcome Co. | Pharmaceutical compositions |
| DE3113880A1 (de) * | 1981-04-07 | 1982-10-21 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von coffein |
| IT1174773B (it) * | 1983-07-29 | 1987-07-01 | Medosan Ind Biochimi | Attivita' antiaggregante piastrinica e broncolitica della 7-(1-metil-5-p-metilbenzoilpirrol-2-acetamidoetil)teofillina |
| US5736528A (en) * | 1993-10-28 | 1998-04-07 | University Of Florida Research Foundation, Inc. | N6 -(epoxynorborn-2-yl) adenosines as A1 adenosine receptor agonists |
| US5446046A (en) * | 1993-10-28 | 1995-08-29 | University Of Florida Research Foundation | A1 adenosine receptor agonists and antagonists as diuretics |
| US5620676A (en) * | 1994-03-08 | 1997-04-15 | The United States Of America As Represented By The Department Of Health And Human Services | Biologically active ATP analogs |
| US5789416B1 (en) * | 1996-08-27 | 1999-10-05 | Cv Therapeutics Inc | N6 mono heterocyclic substituted adenosine derivatives |
| WO1999031101A1 (en) * | 1997-12-17 | 1999-06-24 | University Of South Florida | Adenosine receptor antagonists with improved bioactivity |
| US6576619B2 (en) | 1999-05-24 | 2003-06-10 | Cv Therapeutics, Inc. | Orally active A1 adenosine receptor agonists |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1230663A (en, 2012) * | 1968-12-10 | 1971-05-05 | ||
| US3728346A (en) * | 1971-07-16 | 1973-04-17 | Degussa | Hydroxyphenylhydroxyalkylaminoalkyltheophyllines |
| JPS5132638B2 (en, 2012) * | 1972-07-13 | 1976-09-14 |
-
1974
- 1974-12-21 DE DE19742460929 patent/DE2460929A1/de active Granted
-
1975
- 1975-11-28 AT AT904575A patent/AT341540B/de not_active IP Right Cessation
- 1975-12-09 LU LU73972A patent/LU73972A1/xx unknown
- 1975-12-11 SU SU752197999A patent/SU603340A3/ru active
- 1975-12-12 DD DD190116A patent/DD124984A5/xx unknown
- 1975-12-15 AU AU87547/75A patent/AU501889B2/en not_active Expired
- 1975-12-16 DK DK571875A patent/DK137677C/da active
- 1975-12-16 FI FI753543A patent/FI62089C/fi not_active IP Right Cessation
- 1975-12-17 US US05/641,550 patent/US3998953A/en not_active Expired - Lifetime
- 1975-12-17 GR GR49628A patent/GR59204B/el unknown
- 1975-12-18 CH CH1643275A patent/CH628346A5/de not_active IP Right Cessation
- 1975-12-18 YU YU03234/75A patent/YU39004B/xx unknown
- 1975-12-18 CS CS758669A patent/CS191289B2/cs unknown
- 1975-12-18 RO RO7584245A patent/RO68381A/ro unknown
- 1975-12-19 FR FR7539174A patent/FR2294706A1/fr active Granted
- 1975-12-19 IL IL48697A patent/IL48697A/xx unknown
- 1975-12-19 GB GB52168/75A patent/GB1517710A/en not_active Expired
- 1975-12-19 SE SE7514477A patent/SE420493B/xx not_active IP Right Cessation
- 1975-12-19 PH PH17894A patent/PH11810A/en unknown
- 1975-12-19 NL NL7514837A patent/NL7514837A/xx not_active Application Discontinuation
- 1975-12-19 BE BE162965A patent/BE836898A/xx not_active IP Right Cessation
- 1975-12-19 HU HU75BO1590A patent/HU174673B/hu unknown
- 1975-12-19 IE IE2787/75A patent/IE43208B1/en unknown
- 1975-12-19 NZ NZ179599A patent/NZ179599A/xx unknown
- 1975-12-19 CA CA242,131A patent/CA1036159A/en not_active Expired
- 1975-12-19 ZA ZA757865A patent/ZA757865B/xx unknown
- 1975-12-19 NO NO754317A patent/NO144928C/no unknown
- 1975-12-19 JP JP50151721A patent/JPS5188995A/ja active Pending
- 1975-12-19 BG BG032887A patent/BG25518A3/xx unknown
- 1975-12-20 ES ES443738A patent/ES443738A1/es not_active Expired
- 1975-12-20 PL PL1975185740A patent/PL99165B1/pl unknown
-
1976
- 1976-09-11 ES ES451457A patent/ES451457A1/es not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS ERMITTELT * |
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