CH639849A5 - Pharmaceuticals containing alkenylxanthines - Google Patents

Pharmaceuticals containing alkenylxanthines Download PDF

Info

Publication number: CH639849A5
Authority: CH; Switzerland
Prior art keywords: methyl; radicals; hexenyl; xanthine; atoms
Prior art date: 1977-04-02

Application number

CH344878A

Other languages

German (de)

English (en)

Inventor

Harald Furrer

Alfons Soeder

Jaromir Komarek

Heinz-Joachim Hinze

Gerhard Muench

Original Assignee

Hoechst Ag

Priority date (The priority date 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 date listed.)

1977-04-02

Filing date

1978-03-31

Publication date

1983-12-15

1978-03-31 Application filed by Hoechst Ag filed Critical Hoechst Ag

1983-12-15 Publication of CH639849A5 publication Critical patent/CH639849A5/de

Links

239000003814 drug Substances 0.000 title claims description 16
LRFVTYWOQMYALW-UHFFFAOYSA-N Xanthine Natural products O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 98
229940075420 xanthine Drugs 0.000 claims description 71
125000004432 carbon atom Chemical group C* 0.000 claims description 35
-1 1-propyl- Chemical group 0.000 claims description 22
150000001875 compounds Chemical class 0.000 claims description 20
125000003342 alkenyl group Chemical group 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 8
230000000694 effects Effects 0.000 claims description 6
210000004556 brain Anatomy 0.000 claims description 3
229940126601 medicinal product Drugs 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000008280 blood Substances 0.000 claims description 2
210000004369 blood Anatomy 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 4
230000036770 blood supply Effects 0.000 claims 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
150000003254 radicals Chemical class 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
239000000243 solution Substances 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000000034 method Methods 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
229940079593 drug Drugs 0.000 description 6
239000000203 mixture Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000013543 active substance Substances 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
229960004559 theobromine Drugs 0.000 description 5
238000004821 distillation Methods 0.000 description 4
239000003480 eluent Substances 0.000 description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
HDAPVDGMACVEKL-UHFFFAOYSA-N 1,3-dibutyl-7h-purine-2,6-dione Chemical compound O=C1N(CCCC)C(=O)N(CCCC)C2=C1NC=N2 HDAPVDGMACVEKL-UHFFFAOYSA-N 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 3
DMAYBPBPEUFIHJ-UHFFFAOYSA-N 4-bromobut-1-ene Chemical compound BrCCC=C DMAYBPBPEUFIHJ-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
241000282326 Felis catus Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
230000003727 cerebral blood flow Effects 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000008030 superplasticizer Substances 0.000 description 3
230000008961 swelling Effects 0.000 description 3
229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
GIMNFISWKTZFKJ-UHFFFAOYSA-N 1,3-diethyl-7h-purine-2,6-dione Chemical compound O=C1N(CC)C(=O)N(CC)C2=C1NC=N2 GIMNFISWKTZFKJ-UHFFFAOYSA-N 0.000 description 2
QUNWUDVFRNGTCO-UHFFFAOYSA-N 1,7-dimethylxanthine Chemical compound N1C(=O)N(C)C(=O)C2=C1N=CN2C QUNWUDVFRNGTCO-UHFFFAOYSA-N 0.000 description 2
OTUCSVCIIQRSNG-UHFFFAOYSA-N 3-ethyl-7h-purine-2,6-dione Chemical compound O=C1NC(=O)N(CC)C2=C1NC=N2 OTUCSVCIIQRSNG-UHFFFAOYSA-N 0.000 description 2
GMSNIKWWOQHZGF-UHFFFAOYSA-N 3-methyl-9H-xanthine Chemical compound O=C1NC(=O)N(C)C2=C1N=CN2 GMSNIKWWOQHZGF-UHFFFAOYSA-N 0.000 description 2
LPNANKDXVBMDKE-UHFFFAOYSA-N 5-bromopent-1-ene Chemical compound BrCCCC=C LPNANKDXVBMDKE-UHFFFAOYSA-N 0.000 description 2
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 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
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 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
229960003556 aminophylline Drugs 0.000 description 2
PECIYKGSSMCNHN-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=NC=N[C]21.O=C1N(C)C(=O)N(C)C2=NC=N[C]21 PECIYKGSSMCNHN-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000017531 blood circulation Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000008298 dragée Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000002768 hydroxyalkyl group Chemical group 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
125000005188 oxoalkyl group Chemical group 0.000 description 2
239000012071 phase Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
RIMXEJYJXDBLIE-UHFFFAOYSA-N 6-bromohex-1-ene Chemical compound BrCCCCC=C RIMXEJYJXDBLIE-UHFFFAOYSA-N 0.000 description 1
HSUAWWZANQUYQS-UHFFFAOYSA-N 7-(5-hydroxyhexyl)-1,3-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2CCCCC(O)C HSUAWWZANQUYQS-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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 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
238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
229920002472 Starch Polymers 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000001785 acacia senegal l. willd gum Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
238000007792 addition Methods 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 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
229940081734 cellulose acetate phthalate Drugs 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000008119 colloidal silica Substances 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
239000008120 corn starch Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
229940113088 dimethylacetamide Drugs 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
210000001105 femoral artery Anatomy 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
230000008338 local blood flow Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
JNMIXMFEVJHFNY-UHFFFAOYSA-M methyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 JNMIXMFEVJHFNY-UHFFFAOYSA-M 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
XYDYWTJEGDZLTH-UHFFFAOYSA-N methylenetriphenylphosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C)C1=CC=CC=C1 XYDYWTJEGDZLTH-UHFFFAOYSA-N 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
235000021239 milk protein Nutrition 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000003921 oil Substances 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000002270 phosphoric acid ester group Chemical group 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000523 sample Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
QVGLHVDBDYLFON-UHFFFAOYSA-M sodium;1,3-dimethylpurin-7-ide-2,6-dione Chemical compound [Na+].O=C1N(C)C(=O)N(C)C2=C1[N-]C=N2 QVGLHVDBDYLFON-UHFFFAOYSA-M 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
239000008223 sterile water Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
RJSZFSOFYVMDIC-UHFFFAOYSA-N tert-butyl n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC(C)(C)C RJSZFSOFYVMDIC-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
238000012876 topography Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 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
239000001993 wax Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000012991 xanthate Substances 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
- 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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Heart & Thoracic Surgery (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH344878A 1977-04-02 1978-03-31 Pharmaceuticals containing alkenylxanthines CH639849A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2714953A DE2714953C2 (de)	1977-04-02	1977-04-02	Arzneimittel

Publications (1)

Publication Number	Publication Date
CH639849A5 true CH639849A5 (en)	1983-12-15

Family

ID=6005579

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH344878A CH639849A5 (en)	1977-04-02	1978-03-31	Pharmaceuticals containing alkenylxanthines

Country Status (11)

Country	Link
JP (1)	JPS53149998A (fr)
AU (1)	AU523125B2 (fr)
BE (1)	BE865601A (fr)
CA (1)	CA1123435A (fr)
CH (1)	CH639849A5 (fr)
DE (1)	DE2714953C2 (fr)
FR (1)	FR2420346A1 (fr)
GB (1)	GB1580782A (fr)
IT (1)	IT1094052B (fr)
NL (1)	NL188620C (fr)
ZA (1)	ZA781876B (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH654008A5 (fr) *	1979-05-22	1986-01-31	Nestle Sa	Procede de preparation de 1,3,7-trialkylxanthines.
DE2929596A1 (de) *	1979-07-21	1981-02-05	Hoechst Ag	Verfahren zur herstellung von oxoalkyl-xanthinen
GB8826595D0 (en) *	1988-11-14	1988-12-21	Beecham Wuelfing Gmbh & Co Kg	Active compounds
GB9312853D0 (en)	1993-06-22	1993-08-04	Euro Celtique Sa	Chemical compounds
US5591776A (en)	1994-06-24	1997-01-07	Euro-Celtique, S.A.	Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV
US5922751A (en)	1994-06-24	1999-07-13	Euro-Celtique, S.A.	Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same
EP0799040B1 (fr)	1994-12-13	2003-08-20	Euroceltique S.A.	Thioxanthines trisubstituees
US6066641A (en) *	1994-12-13	2000-05-23	Euro-Celtique S.A.	Aryl thioxanthines
US6166041A (en)	1995-10-11	2000-12-26	Euro-Celtique, S.A.	2-heteroaryl and 2-heterocyclic benzoxazoles as PDE IV inhibitors for the treatment of asthma
US6075016A (en)	1996-04-10	2000-06-13	Euro-Celtique S.A.	6,5-fused aromatic ring systems having enhanced phosphodiesterase IV inhibitory activity
US5864037A (en)	1996-06-06	1999-01-26	Euro-Celtique, S.A.	Methods for the synthesis of chemical compounds having PDE-IV inhibitory activity

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH88833A (de) *	1920-06-22	1921-08-01	Hoffmann La Roche	Verfahren zur Darstellung von 1-Allyl-3-7-dimethylxanthin.
CH97979A (de) *	1921-10-07	1923-02-16	Chem Ind Basel	Verfahren zur Darstellung von Triallylxanthin.
CH97978A (de) *	1921-10-07	1923-02-16	Chem Ind Basel	Verfahren zur Darstellung von Diallylxanthin.
US2673848A (en) *	1951-12-29	1954-03-30	Searle & Co	3-alkenylxanthines and their lower 1-alkyl derivatives
DE2432702C2 (de) *	1974-07-08	1983-01-20	Hoechst Ag, 6000 Frankfurt	Verfahren zur Herstellung von Hydroxyalkylxanthinen

1977
- 1977-04-02 DE DE2714953A patent/DE2714953C2/de not_active Expired
1978
- 1978-03-31 FR FR7809399A patent/FR2420346A1/fr active Granted
- 1978-03-31 IT IT21900/78A patent/IT1094052B/it active
- 1978-03-31 BE BE186498A patent/BE865601A/fr not_active IP Right Cessation
- 1978-03-31 NL NLAANVRAGE7803504,A patent/NL188620C/xx not_active IP Right Cessation
- 1978-03-31 CH CH344878A patent/CH639849A5/de not_active IP Right Cessation
- 1978-03-31 JP JP3692178A patent/JPS53149998A/ja active Granted
- 1978-03-31 GB GB12728/78A patent/GB1580782A/en not_active Expired
- 1978-04-03 CA CA300,333A patent/CA1123435A/fr not_active Expired
- 1978-04-03 ZA ZA00781876A patent/ZA781876B/xx unknown
- 1978-04-03 AU AU34672/78A patent/AU523125B2/en not_active Expired

Also Published As

Publication number	Publication date
GB1580782A (en)	1980-12-03
AU523125B2 (en)	1982-07-15
FR2420346B1 (fr)	1983-05-27
NL7803504A (nl)	1978-10-04
CA1123435A (fr)	1982-05-11
JPS53149998A (en)	1978-12-27
IT1094052B (it)	1985-07-26
AU3467278A (en)	1979-10-11
DE2714953C2 (de)	1986-09-25
IT7821900A0 (it)	1978-03-31
BE865601A (fr)	1978-10-02
NL188620B (nl)	1992-03-16
JPS5649886B2 (fr)	1981-11-25
FR2420346A1 (fr)	1979-10-19
NL188620C (nl)	1992-08-17
ZA781876B (en)	1979-06-27
DE2714953A1 (de)	1979-02-01

Legal Events

Date	Code	Title	Description
1996-11-15	PL	Patent ceased

Publication	Publication Date	Title
DE2330742C2 (de)	1982-07-29	1-(Oxoalkyl)-3-methyl-7-alkylxanthine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2165962C2 (de)	1982-05-13	4-Hydroxy-6-arylpyrimidine
EP0044928B1 (fr)	1985-03-13	Le nitrate de 1,4,3,6-dianhydro-hexite substitué de bases puriques, leur procédé de préparation et leur composition pharmaceutique
CH639849A5 (en)	1983-12-15	Pharmaceuticals containing alkenylxanthines
DE2713389C2 (fr)	1992-03-19
DE3717080C2 (de)	1996-02-08	1-(Hydroxystyryl)-5H-2,3-benzodiazepinderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
EP0528164B1 (fr)	1996-05-29	Utilisation de dérivés de xanthine pour la fabrication d'un médicament pour le traitement de lésions secondaires des cellules nerveuses et de troubles de fonction après des traumatismes du crâne ou du cerveau
DE2931418C2 (fr)	1989-06-29
DE2403122C2 (fr)	1990-03-22
DE1670005C2 (de)	1982-06-09	&beta;-(4,5-Diphenyloxazol-2-yl)-propionsäure oder ein pharmazeutisch verträgliches Salz davon, Verfahren zur Herstellung dieser Verbindungen und pharmazeutische Zubereitungen, welche diese Verbindungen enthalten
EP0317855B1 (fr)	1991-12-18	Produits pharmaceutiques
DE2951671C2 (de)	1986-02-20	Arzneimittelzubereitung mit Antithrombosewirkung und Hemmwirkung auf die Agglomeration der Blutplättchen
EP0030343B1 (fr)	1983-08-31	Amino-2 dihydro-3,4-pyridines substituées, procédé pour leur préparation et utilisation comme médicaments
CH616931A5 (en)	1980-04-30	Process for the preparation of 2,4-diamino-5-benzylpyrimidines acting as potentiator for sulphonamides.
EP0068259A1 (fr)	1983-01-05	Dérivés de la 2-amino-pyridine, substitués, procédé pour leur préparation et leur préparation et utilisation dans des médicaments
DE2248741B2 (de)	1974-11-14	5-Phenoxy-und 5-Thiophenoxy-2(lH)-Pyrimidinone
DE2530515C2 (de)	1983-12-01	4- bzw. 7-Hydroxy-4,5,6,7-tetrahydrothieno-[3,2-c] bzw.[2,3-c] pyridine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittelzubereitungen
DE2836147A1 (de)	1980-02-28	Arzneimittel, darin enthaltene alkenylxanthine und verfahren zu ihrer herstellung
DE2951669C2 (de)	1985-08-22	Arzneimittel
DE2708827A1 (de)	1977-09-08	Substituierte purinverbindungen, verfahren zu ihrer herstellung und pharmazeutische zubereitungen
DE2366527C2 (fr)	1987-08-27
DE1770839C3 (de)	1977-11-03	7-Chlor-10-(3-dimethylaminopropyl)- benzo [b] [13 eckige Klammer zu naphthyridon-5(10H) und dessen Salze, ein Verfahren zu seiner Herstellung sowie eine pharmazeutische Zubereitung
CH622520A5 (en)	1981-04-15	Process for the preparation of novel 3-alkyl-7-oxoalkylxanthines
DE2366501C2 (de)	1983-11-24	1-Alkyl-3-methyl-7-oxoalkylxanthine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
AT359524B (de)	1980-11-10	Verfahren zur herstellung von neuen mono-oder di-alkenylxanthinen