IL96708A - Compounds 1-) Hydrocarbyl elliptical (-3-) Transformed phenyl (-xanthine, preparation and pharmaceutical preparations containing them - Google Patents
Compounds 1-) Hydrocarbyl elliptical (-3-) Transformed phenyl (-xanthine, preparation and pharmaceutical preparations containing themInfo
- Publication number
- IL96708A IL96708A IL9670890A IL9670890A IL96708A IL 96708 A IL96708 A IL 96708A IL 9670890 A IL9670890 A IL 9670890A IL 9670890 A IL9670890 A IL 9670890A IL 96708 A IL96708 A IL 96708A
- Authority
- IL
- Israel
- Prior art keywords
- xanthine
- compound
- amino
- process according
- group
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- -1 methylenedioxy Chemical group 0.000 claims abstract description 14
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims abstract description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- LNDZXOWGUAIUBG-UHFFFAOYSA-N 6-aminouracil Chemical compound NC1=CC(=O)NC(=O)N1 LNDZXOWGUAIUBG-UHFFFAOYSA-N 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 8
- 239000002585 base Substances 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 6
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 235000019253 formic acid Nutrition 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 150000007530 organic bases Chemical class 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 11
- 229940075420 xanthine Drugs 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 abstract description 5
- 208000006673 asthma Diseases 0.000 abstract description 3
- 229940124630 bronchodilator Drugs 0.000 abstract description 3
- 239000000168 bronchodilator agent Substances 0.000 abstract description 3
- 229940124549 vasodilator Drugs 0.000 abstract description 3
- 239000003071 vasodilator agent Substances 0.000 abstract description 3
- 206010002383 Angina Pectoris Diseases 0.000 abstract description 2
- 206010007559 Cardiac failure congestive Diseases 0.000 abstract description 2
- 206010019280 Heart failures Diseases 0.000 abstract description 2
- 206010020772 Hypertension Diseases 0.000 abstract description 2
- 208000005314 Multi-Infarct Dementia Diseases 0.000 abstract description 2
- 201000004810 Vascular dementia Diseases 0.000 abstract description 2
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- CSMWJXBSXGUPGY-UHFFFAOYSA-L sodium dithionate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)S([O-])(=O)=O CSMWJXBSXGUPGY-UHFFFAOYSA-L 0.000 abstract 1
- 229940075931 sodium dithionate Drugs 0.000 abstract 1
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 15
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 description 11
- 239000000725 suspension Substances 0.000 description 10
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 241000700199 Cavia porcellus Species 0.000 description 6
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000638 stimulation Effects 0.000 description 6
- 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 5
- 230000000747 cardiac effect Effects 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 5
- 239000000600 sorbitol Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000002570 phosphodiesterase III inhibitor Substances 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 4
- 229960000278 theophylline Drugs 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 230000003834 intracellular effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241000219161 Theobroma Species 0.000 description 2
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- RNLQIBCLLYYYFJ-UHFFFAOYSA-N amrinone Chemical compound N1C(=O)C(N)=CC(C=2C=CN=CC=2)=C1 RNLQIBCLLYYYFJ-UHFFFAOYSA-N 0.000 description 2
- 229960002105 amrinone Drugs 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 229940095074 cyclic amp Drugs 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000000297 inotrophic effect Effects 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
- KRCMKUNIILUXPF-UHFFFAOYSA-N methyl 4-hydroxybenzoate;sodium Chemical compound [Na].COC(=O)C1=CC=C(O)C=C1 KRCMKUNIILUXPF-UHFFFAOYSA-N 0.000 description 2
- VZXIAVMLJCJLPP-UHFFFAOYSA-N n-[4-(3-oxo-2h-pyrazin-6-yl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=NCC(=O)N=C1 VZXIAVMLJCJLPP-UHFFFAOYSA-N 0.000 description 2
- 239000002773 nucleotide Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229940068968 polysorbate 80 Drugs 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- WXSLOYPZKHFWII-UHFFFAOYSA-N propyl 4-hydroxybenzoate;sodium Chemical compound [Na].CCCOC(=O)C1=CC=C(O)C=C1 WXSLOYPZKHFWII-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 description 2
- 229950005741 rolipram Drugs 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 235000010268 sodium methyl p-hydroxybenzoate Nutrition 0.000 description 2
- 239000004290 sodium methyl p-hydroxybenzoate Substances 0.000 description 2
- 235000010230 sodium propyl p-hydroxybenzoate Nutrition 0.000 description 2
- 239000004404 sodium propyl p-hydroxybenzoate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical group CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HMURFOQVDLLLSF-UHFFFAOYSA-N 1-butyl-3-(3-methoxyphenyl)-7h-purine-2,6-dione Chemical compound C1=2N=CNC=2C(=O)N(CCCC)C(=O)N1C1=CC=CC(OC)=C1 HMURFOQVDLLLSF-UHFFFAOYSA-N 0.000 description 1
- YVEFQKRANVAQIZ-UHFFFAOYSA-N 1-butyl-3-(3-nitrophenyl)-7h-purine-2,6-dione Chemical compound C1=2N=CNC=2C(=O)N(CCCC)C(=O)N1C1=CC=CC([N+]([O-])=O)=C1 YVEFQKRANVAQIZ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LEEHIHGZHAYSGX-UHFFFAOYSA-N 6-amino-1-(4-chlorophenyl)-3-propylpyrimidine-2,4-dione Chemical compound O=C1N(CCC)C(=O)C=C(N)N1C1=CC=C(Cl)C=C1 LEEHIHGZHAYSGX-UHFFFAOYSA-N 0.000 description 1
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.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 WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 101710095468 Cyclase Proteins 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
- 239000001828 Gelatine Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004147 Sorbitan trioleate Substances 0.000 description 1
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
- 208000006011 Stroke Diseases 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
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 1
- 102000030621 adenylate cyclase Human genes 0.000 description 1
- 108060000200 adenylate cyclase Proteins 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- GVTLDPJNRVMCAL-UHFFFAOYSA-N arofylline Chemical compound C1=2N=CNC=2C(=O)N(CCC)C(=O)N1C1=CC=C(Cl)C=C1 GVTLDPJNRVMCAL-UHFFFAOYSA-N 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000000496 cardiotonic agent Substances 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- ZOOGRGPOEVQQDX-KHLHZJAASA-N cyclic guanosine monophosphate Chemical compound C([C@H]1O2)O[P@](O)(=O)O[C@@H]1[C@H](O)[C@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-KHLHZJAASA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229960001021 lactose monohydrate Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000004648 relaxation of smooth muscle Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 210000002955 secretory cell Anatomy 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000009044 synergistic interaction Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000002861 ventricular Effects 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
-
- 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)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Processing Of Stones Or Stones Resemblance Materials (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Re-Forming, After-Treatment, Cutting And Transporting Of Glass Products (AREA)
- Container, Conveyance, Adherence, Positioning, Of Wafer (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898929208A GB8929208D0 (en) | 1989-12-27 | 1989-12-27 | New xanthine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL96708A0 IL96708A0 (en) | 1991-09-16 |
| IL96708A true IL96708A (en) | 1994-06-24 |
Family
ID=10668520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9670890A IL96708A (en) | 1989-12-27 | 1990-12-18 | Compounds 1-) Hydrocarbyl elliptical (-3-) Transformed phenyl (-xanthine, preparation and pharmaceutical preparations containing them |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US5223504A (pl) |
| EP (1) | EP0435811B1 (pl) |
| JP (1) | JPH089617B2 (pl) |
| KR (1) | KR970001528B1 (pl) |
| CN (1) | CN1029967C (pl) |
| AT (1) | ATE93860T1 (pl) |
| AU (1) | AU635104B2 (pl) |
| BR (1) | BR9007258A (pl) |
| CA (1) | CA2045478C (pl) |
| CZ (1) | CZ278328B6 (pl) |
| DE (1) | DE69003087T2 (pl) |
| DK (1) | DK0435811T3 (pl) |
| EG (1) | EG19436A (pl) |
| ES (1) | ES2058864T3 (pl) |
| FI (1) | FI96207C (pl) |
| GB (1) | GB8929208D0 (pl) |
| HU (2) | HU208825B (pl) |
| IE (1) | IE64065B1 (pl) |
| IL (1) | IL96708A (pl) |
| MX (1) | MX23884A (pl) |
| MY (1) | MY105303A (pl) |
| NO (1) | NO178111C (pl) |
| NZ (1) | NZ236517A (pl) |
| PL (1) | PL166152B1 (pl) |
| PT (1) | PT96332B (pl) |
| RU (1) | RU2073679C1 (pl) |
| SK (1) | SK278365B6 (pl) |
| UA (1) | UA32512C2 (pl) |
| WO (1) | WO1991009859A1 (pl) |
| ZA (1) | ZA9010240B (pl) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX9203323A (es) * | 1991-07-11 | 1994-07-29 | Hoechst Ag | El empleo de derivados de xantina para el tratamiento de lesiones secundarias de las celulas nerviosas y trastornos funcionales despues de traumas craneo-cerebrales. |
| US5521315A (en) * | 1993-01-12 | 1996-05-28 | Cell Therapeutics, Inc. | Olefin substituted long chain compounds |
| GB9312853D0 (en) | 1993-06-22 | 1993-08-04 | Euro Celtique Sa | Chemical compounds |
| US5922751A (en) | 1994-06-24 | 1999-07-13 | Euro-Celtique, S.A. | Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same |
| 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 |
| US5661153A (en) * | 1994-07-19 | 1997-08-26 | Japan Energy Corporation | 1-arylpyrimidine derivatives and pharmaceutical use thereof |
| EP0799040B1 (en) * | 1994-12-13 | 2003-08-20 | Euroceltique S.A. | Trisubstituted thioxanthines |
| JPH10508032A (ja) | 1994-12-13 | 1998-08-04 | ユーロ−セルティーク，エス．エイ． | アリールチオキサンチン類 |
| US6025361A (en) * | 1994-12-13 | 2000-02-15 | Euro-Celtique, S.A. | Trisubstituted thioxanthines |
| WO1996036638A1 (en) * | 1995-05-19 | 1996-11-21 | Chiroscience Limited | Xanthines and their therapeutic use |
| 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 |
| US5874437A (en) * | 1996-11-01 | 1999-02-23 | Nitromed, Inc. | Nitrosated and nitrosylated phosphodiesterase inhibitor compounds, compositions and their uses |
| USRE37234E1 (en) * | 1996-11-01 | 2001-06-19 | Nitromed, Inc. | Nitrosated and nitrosylated phosphodiestrase inhibitor compounds, compositions and their uses |
| CA2270118A1 (en) * | 1996-11-01 | 1998-05-14 | Nitromed Inc. | Nitrosated and nitrosylated phosphodiesterase inhibitor compounds, compositions and their uses |
| US6331543B1 (en) * | 1996-11-01 | 2001-12-18 | Nitromed, Inc. | Nitrosated and nitrosylated phosphodiesterase inhibitors, compositions and methods of use |
| US5958926A (en) | 1996-11-01 | 1999-09-28 | Nitromed, Inc. | Nitrosated and nitrosylated phosphodiesterase inhibitor compounds, compositions and their uses |
| GB9623859D0 (en) * | 1996-11-15 | 1997-01-08 | Chiroscience Ltd | Novel compounds |
| US6472425B1 (en) | 1997-10-31 | 2002-10-29 | Nitromed, Inc. | Methods for treating female sexual dysfunctions |
| IL132407A0 (en) * | 1998-10-21 | 2001-03-19 | Pfizer Prod Inc | Method for treating congestive heart failure |
| ES2228512T3 (es) | 1999-05-04 | 2005-04-16 | Altana Pharma Ag | Combinacion sinergica que comprende roflumilast y un inhibidor de pde-3. |
| PL200923B1 (pl) | 1999-08-21 | 2009-02-27 | Nycomed Gmbh | Lek zawierający inhibitor PDE w połączeniu z agonistą receptoraß₂ -adrenergicznego oraz zastosowanie połączenia roflumilastu i salmeterolu |
| GB0005199D0 (en) * | 2000-03-04 | 2000-04-26 | Imp College Innovations Ltd | Modulation of histone deacetylase |
| CA2402384A1 (en) * | 2000-03-16 | 2001-09-20 | Inflazyme Pharmaceuticals Ltd. | Benzylated pde4 inhibitors |
| KR20040007583A (ko) * | 2001-05-23 | 2004-01-24 | 다나베 세이야꾸 가부시키가이샤 | 연골 질환의 재생치료용 조성물 |
| WO2002094321A1 (en) * | 2001-05-23 | 2002-11-28 | Tanabe Seiyaku Co., Ltd. | Compositions for promoting healing of bone fracture |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| JP2006522151A (ja) | 2003-04-01 | 2006-09-28 | アプライド リサーチ システムズ エーアールエス ホールディング ナームロゼ フェンノートシャップ | 不妊症におけるホスホジエステラーゼ阻害剤 |
| RU2395511C2 (ru) * | 2004-02-14 | 2010-07-27 | Смитклайн Бичам Корпорейшн | Новые соединения |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| WO2008151257A2 (en) | 2007-06-04 | 2008-12-11 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| ES2627848T3 (es) | 2008-06-04 | 2017-07-31 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos |
| ES2624828T3 (es) | 2008-07-16 | 2017-07-17 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| MX357121B (es) | 2011-03-01 | 2018-06-27 | Synergy Pharmaceuticals Inc Star | Proceso de preparacion de agonistas c de guanilato ciclasa. |
| EP2958577A2 (en) | 2013-02-25 | 2015-12-30 | Synergy Pharmaceuticals Inc. | Guanylate cyclase receptor agonists for use in colonic cleansing |
| US9708367B2 (en) | 2013-03-15 | 2017-07-18 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase and their uses |
| EP2968439A2 (en) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| PL3004138T3 (pl) | 2013-06-05 | 2024-07-29 | Bausch Health Ireland Limited | Ultra-oczyszczeni agoniści peptydowi cyklazy guanylanowej C, sposób ich uzyskiwania i ich zastosowanie |
| CA2920856C (en) | 2013-08-09 | 2026-03-03 | Ardelyx, Inc. | Ph modulating compounds for inhibiting gastrointestinal phosphate uptake |
| EP3165224A1 (en) | 2015-11-09 | 2017-05-10 | Albert-Ludwigs-Universität Freiburg | Use of pde4 inhibitors for the prophylaxis and/or therapy of dyslipoproteinaemia and related disorders |
| WO2017089347A1 (en) | 2015-11-25 | 2017-06-01 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods and pharmaceutical compositions for the treatment of braf inhibitor resistant melanomas |
| AR115689A1 (es) | 2018-07-05 | 2021-02-17 | Sumitomo Chemical Co | Compuestos de uracilo y su utilización |
| JP2022533251A (ja) | 2019-05-21 | 2022-07-21 | アルデリックス， インコーポレイテッド | 患者において血清リン酸塩を低下させるための組み合わせ |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1245969B (de) * | 1967-08-03 | VEB Arzneimittelwerk Dresden, Radebeul | Verfahren zur Herstellung von Xanthinderivaten | |
| CH629788A5 (de) * | 1977-07-20 | 1982-05-14 | Lonza Ag | Verfahren zur herstellung von 5,6-diaminouracil. |
| SE416810C (sv) * | 1977-10-14 | 1982-07-19 | Draco Ab | Forfarande for framstellning av xantinderivat med antiallergisk aktivitet |
| GB8826595D0 (en) * | 1988-11-14 | 1988-12-21 | Beecham Wuelfing Gmbh & Co Kg | Active compounds |
-
1989
- 1989-12-27 GB GB898929208A patent/GB8929208D0/en active Pending
-
1990
- 1990-12-18 SK SK6341-90A patent/SK278365B6/sk unknown
- 1990-12-18 NZ NZ236517A patent/NZ236517A/xx unknown
- 1990-12-18 IL IL9670890A patent/IL96708A/en not_active IP Right Cessation
- 1990-12-18 CZ CS906341A patent/CZ278328B6/cs not_active IP Right Cessation
- 1990-12-19 DE DE90500126T patent/DE69003087T2/de not_active Expired - Fee Related
- 1990-12-19 ZA ZA9010240A patent/ZA9010240B/xx unknown
- 1990-12-19 ES ES90500126T patent/ES2058864T3/es not_active Expired - Lifetime
- 1990-12-19 EP EP90500126A patent/EP0435811B1/en not_active Expired - Lifetime
- 1990-12-19 AT AT90500126T patent/ATE93860T1/de not_active IP Right Cessation
- 1990-12-19 DK DK90500126.9T patent/DK0435811T3/da active
- 1990-12-20 EG EG75090A patent/EG19436A/xx active
- 1990-12-20 IE IE463490A patent/IE64065B1/en not_active IP Right Cessation
- 1990-12-21 PT PT96332A patent/PT96332B/pt not_active IP Right Cessation
- 1990-12-21 MX MX2388490A patent/MX23884A/es unknown
- 1990-12-21 MY MYPI90002243A patent/MY105303A/en unknown
- 1990-12-21 CN CN90110056A patent/CN1029967C/zh not_active Expired - Fee Related
- 1990-12-27 WO PCT/GB1990/002027 patent/WO1991009859A1/en not_active Ceased
- 1990-12-27 CA CA002045478A patent/CA2045478C/en not_active Expired - Fee Related
- 1990-12-27 PL PL90292006A patent/PL166152B1/pl not_active IP Right Cessation
- 1990-12-27 BR BR909007258A patent/BR9007258A/pt not_active Application Discontinuation
- 1990-12-27 RU SU905001584A patent/RU2073679C1/ru not_active IP Right Cessation
- 1990-12-27 US US07/743,388 patent/US5223504A/en not_active Expired - Lifetime
- 1990-12-27 HU HU912782A patent/HU208825B/hu not_active IP Right Cessation
- 1990-12-27 JP JP3501868A patent/JPH089617B2/ja not_active Expired - Fee Related
- 1990-12-27 UA UA5001584A patent/UA32512C2/uk unknown
- 1990-12-27 KR KR1019910700878A patent/KR970001528B1/ko not_active Expired - Fee Related
- 1990-12-27 AU AU69768/91A patent/AU635104B2/en not_active Ceased
-
1991
- 1991-08-19 NO NO913236A patent/NO178111C/no unknown
- 1991-08-26 FI FI914014A patent/FI96207C/fi active
-
1995
- 1995-06-30 HU HU95P/P00698P patent/HU211573A9/hu unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU635104B2 (en) | New xanthine derivatives | |
| AU773504B2 (en) | Derivatives of pyrimido(6,1-a)isoquinolin-4-one | |
| US4804664A (en) | Method and pharmaceutical preparation for treating chronic obstructive airway disease and cardiac disease, and intermediates for the preparation of therapeutically active xanthine derivatives | |
| JPH0641466B2 (ja) | ピラゾロトリアジン誘導体およびそれを含有するキサンチンオキシダーゼ阻害剤 | |
| HU180219B (en) | Process for producing substituted xantine derivatives and salts | |
| US5223503A (en) | 6-substituted pyrido[2,3-d]pyrimidines as antineoplastic agents | |
| KR900000552B1 (ko) | 항알레르기 및 소염 제제와 그의 제조방법 | |
| NO161174B (no) | Analogifremgangsmaate ved fremstilling av terapeutisk aktive 1-4 dihydropyridin-derivater. | |
| HU190683B (en) | Process for preparing substituted 3-amino-sydnone imines | |
| CS276993B6 (en) | Oxadiazolylalkylpurine derivatives, processes of their preparation and pharmaceuticals comprising thereof | |
| AU601004B2 (en) | Triazine derivatives | |
| US5744473A (en) | PDE IV inhibitors: "bis-compounds" | |
| WO1999062905A1 (en) | 8-phenylxanthine derivatives and their use as phosphodiesterase inhibitors | |
| NZ196829A (en) | Certain 3,8-disubstituted-3,7-dihydro-1h-purine-2,6-diones | |
| US4450160A (en) | 1,2-Dihydropyrido[3,4-b]-pyrazines and method and intermediates for preparing same | |
| US8268831B2 (en) | Compounds derived from 2-(3-methylenedioxy)-benzoyl indol | |
| EP0027679A2 (en) | Substituted-5-((7-chloro-4-quinolinyl)amino)-3-(amino-methyl)-(1,1'-biphenyl)-2-ol compounds; processes for their production; and pharmaceutical compositions containing the compounds | |
| NZ206316A (en) | Acridanone derivatives | |
| IE56384B1 (en) | Dihydropyridines | |
| NO137596B (no) | Analogifremgangsm}te for fremstilling av terapeutisk aktive hydroksy-pyrimidinderivater |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| KB | Patent renewed | ||
| HS | Change of address for service | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |