HU180009B - Process for producing new 8-azapurin-6-one derivatives - Google Patents
Process for producing new 8-azapurin-6-one derivatives Download PDFInfo
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- HU180009B HU180009B HU77MA2922A HUMA002922A HU180009B HU 180009 B HU180009 B HU 180009B HU 77MA2922 A HU77MA2922 A HU 77MA2922A HU MA002922 A HUMA002922 A HU MA002922A HU 180009 B HU180009 B HU 180009B
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- 238000000034 method Methods 0.000 title claims description 24
- WTVSOESDARPVQO-UHFFFAOYSA-N triazolo[4,5-d]pyrimidin-7-one Chemical class O=C1N=CN=C2N=NN=C12 WTVSOESDARPVQO-UHFFFAOYSA-N 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 117
- -1 alkali metal alkoxide Chemical class 0.000 claims description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 12
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 150000001540 azides Chemical class 0.000 claims description 5
- 238000011065 in-situ storage Methods 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 239000012954 diazonium Substances 0.000 claims description 4
- 239000002609 medium Substances 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 239000000872 buffer Substances 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000001879 copper Chemical class 0.000 claims description 2
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- 238000005809 transesterification reaction Methods 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 239000001110 calcium chloride Substances 0.000 claims 1
- 229910001628 calcium chloride Inorganic materials 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 50
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- 238000000354 decomposition reaction Methods 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 11
- 125000001589 carboacyl group Chemical group 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- NZWABNSJAMPUFU-UHFFFAOYSA-N 5-(5-amino-2-propoxyphenyl)triazolo[4,5-d]pyrimidin-7-one Chemical compound CCCOC1=CC=C(N)C=C1C1=NC(=O)C2=NN=NC2=N1 NZWABNSJAMPUFU-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 6
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 6
- 239000000908 ammonium hydroxide Substances 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- RCFKMKJCEUFHMD-UHFFFAOYSA-N diethyl 2-[[3-(7-oxotriazolo[4,5-d]pyrimidin-5-yl)-4-propoxyanilino]methylidene]propanedioate Chemical compound CCCOC1=CC=C(NC=C(C(=O)OCC)C(=O)OCC)C=C1C1=NC(=O)C2=NN=NC2=N1 RCFKMKJCEUFHMD-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000003302 alkenyloxy group Chemical group 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- JEBYWVVQIFAIOO-UHFFFAOYSA-N 3-(7-oxotriazolo[4,5-d]pyrimidin-5-yl)-4-propoxybenzoic acid Chemical compound CCCOC1=CC=C(C(O)=O)C=C1C1=NC(=O)C2=NN=NC2=N1 JEBYWVVQIFAIOO-UHFFFAOYSA-N 0.000 description 4
- QAHAYFXLXJTXQQ-UHFFFAOYSA-N 3-(7-oxotriazolo[4,5-d]pyrimidin-5-yl)-4-propoxybenzonitrile Chemical compound CCCOC1=CC=C(C#N)C=C1C1=NC(=O)C2=NN=NC2=N1 QAHAYFXLXJTXQQ-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 4
- 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 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 4
- 125000005133 alkynyloxy group Chemical group 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 125000003884 phenylalkyl group Chemical group 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 3
- YUJJDWGEVGGMBN-UHFFFAOYSA-N 5-(5-nitro-2-propoxyphenyl)triazolo[4,5-d]pyrimidin-7-one Chemical compound CCCOC1=CC=C([N+]([O-])=O)C=C1C1=NC(=O)C2=NN=NC2=N1 YUJJDWGEVGGMBN-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- 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 3
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
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- 230000003287 optical effect Effects 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000008247 solid mixture Substances 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- XGEONPMVLCQUHX-UHFFFAOYSA-N 1-[3-(7-oxotriazolo[4,5-d]pyrimidin-5-yl)-4-propoxyphenyl]-3-propylurea Chemical compound CCCNC(=O)NC1=CC=C(OCCC)C(C=2N=C3N=NN=C3C(=O)N=2)=C1 XGEONPMVLCQUHX-UHFFFAOYSA-N 0.000 description 2
- RFHGOTUNZZXENC-UHFFFAOYSA-N 1-methyl-3-[3-(7-oxotriazolo[4,5-d]pyrimidin-5-yl)-4-propoxyphenyl]thiourea Chemical compound CCCOC1=CC=C(NC(=S)NC)C=C1C1=NC(=O)C2=NN=NC2=N1 RFHGOTUNZZXENC-UHFFFAOYSA-N 0.000 description 2
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- QGZWOWFPTHJDNM-UHFFFAOYSA-N 5-(5-amino-2-methoxyphenyl)triazolo[4,5-d]pyrimidin-7-one Chemical compound COC1=CC=C(N)C=C1C1=NC(=O)C2=NN=NC2=N1 QGZWOWFPTHJDNM-UHFFFAOYSA-N 0.000 description 2
- GMMAENNPXKEUEN-UHFFFAOYSA-N 5-[2-propoxy-5-(2h-tetrazol-5-yl)phenyl]triazolo[4,5-d]pyrimidin-7-one Chemical compound C1=C(C=2N=C3N=NN=C3C(=O)N=2)C(OCCC)=CC=C1C1=NN=NN1 GMMAENNPXKEUEN-UHFFFAOYSA-N 0.000 description 2
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- 229910052801 chlorine Inorganic materials 0.000 description 2
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- SWBPAWNHHWHXMS-UHFFFAOYSA-N diethyl 2-[[3-(7-oxotriazolo[4,5-d]pyrimidin-5-yl)-4-propoxyphenyl]diazenyl]propanedioate Chemical compound CCCOC1=CC=C(N=NC(C(=O)OCC)C(=O)OCC)C=C1C1=NC(=O)C2=NN=NC2=N1 SWBPAWNHHWHXMS-UHFFFAOYSA-N 0.000 description 2
- RFUSGEGBEZJORG-UHFFFAOYSA-N diethyl 2-[[4-methoxy-3-(7-oxo-2,3-dihydrotriazolo[4,5-d]pyrimidin-5-yl)anilino]methylidene]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=CNC1=CC=C(OC)C(C2=NC(=O)C3=NNNC3=N2)=C1 RFUSGEGBEZJORG-UHFFFAOYSA-N 0.000 description 2
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- MYODQIXMVFZMHU-UHFFFAOYSA-N ethyl 2-[3-(7-oxotriazolo[4,5-d]pyrimidin-5-yl)-4-propoxyanilino]cyclopentene-1-carboxylate Chemical compound C1=C(C=2N=C3N=NN=C3C(=O)N=2)C(OCCC)=CC=C1NC1=C(C(=O)OCC)CCC1 MYODQIXMVFZMHU-UHFFFAOYSA-N 0.000 description 1
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
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- 239000004304 potassium nitrite Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- ZSDGGBCKZCKOLL-UHFFFAOYSA-O pyridin-1-ium;azide Chemical compound [N-]=[N+]=[N-].C1=CC=[NH+]C=C1 ZSDGGBCKZCKOLL-UHFFFAOYSA-O 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- 239000000375 suspending agent Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
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- REZGGXNDEMKIQB-UHFFFAOYSA-N zaprinast Chemical compound CCCOC1=CC=CC=C1C1=NC(=O)C2=NNNC2=N1 REZGGXNDEMKIQB-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB44008/76A GB1561345A (en) | 1976-10-22 | 1976-10-22 | 8 - azapuring - 6 - ones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU180009B true HU180009B (en) | 1983-01-28 |
Family
ID=10431345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU77MA2922A HU180009B (en) | 1976-10-22 | 1977-10-19 | Process for producing new 8-azapurin-6-one derivatives |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4167568A (show.php) |
| JP (1) | JPS5395993A (show.php) |
| AU (1) | AU510478B2 (show.php) |
| BE (1) | BE859987A (show.php) |
| CA (1) | CA1111027A (show.php) |
| CH (1) | CH628898A5 (show.php) |
| DE (1) | DE2747199A1 (show.php) |
| DK (1) | DK142766B (show.php) |
| GB (1) | GB1561345A (show.php) |
| HU (1) | HU180009B (show.php) |
| IE (1) | IE45810B1 (show.php) |
| LU (1) | LU78363A1 (show.php) |
| NL (1) | NL7711332A (show.php) |
| SE (1) | SE7711836L (show.php) |
| ZA (1) | ZA776258B (show.php) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8817651D0 (en) * | 1988-07-25 | 1988-09-01 | Smith Kline French Lab | Chemical compounds |
| US5250534A (en) * | 1990-06-20 | 1993-10-05 | Pfizer Inc. | Pyrazolopyrimidinone antianginal agents |
| GB9114760D0 (en) * | 1991-07-09 | 1991-08-28 | Pfizer Ltd | Therapeutic agents |
| US5294612A (en) * | 1992-03-30 | 1994-03-15 | Sterling Winthrop Inc. | 6-heterocyclyl pyrazolo [3,4-d]pyrimidin-4-ones and compositions and method of use thereof |
| HU227841B1 (en) | 1997-11-12 | 2012-05-02 | Bayer Pharma AG | 2-phenyl substituted imidazotriazinones, process for their preparation and pharmaceutical compositions thereof |
| IL158738A0 (en) * | 2001-05-09 | 2004-05-12 | Bayer Healthcare Ag | Novel use of 2-phenyl-substituted imidazotriazinones |
| DE10232113A1 (de) | 2002-07-16 | 2004-01-29 | Bayer Ag | Vardenafil Hydrochlorid Trihydrat enthaltende Arzneimittel |
| DE102005001989A1 (de) * | 2005-01-15 | 2006-07-20 | Bayer Healthcare Ag | Intravenöse Formulierungen von PDE-Inhibitoren |
| DE102005009241A1 (de) * | 2005-03-01 | 2006-09-07 | Bayer Healthcare Ag | Arzneiformen mit kontrollierter Bioverfügbarkeit |
| DE102005009240A1 (de) * | 2005-03-01 | 2006-09-07 | Bayer Healthcare Ag | Arzneiformen mit verbesserten pharmakokinetischen Eigenschaften |
| US20090186896A1 (en) * | 2005-09-29 | 2009-07-23 | Bayer Healthcare Ag | PDE Inhibitors and Combinations Thereof for the Treatment of Urological Disorders |
| TWI845600B (zh) | 2019-01-24 | 2024-06-21 | 美商普羅米修斯生物科學股份有限公司 | Gpr35調節劑 |
| AR123034A1 (es) * | 2020-07-23 | 2022-10-26 | Prometheus Biosciences Inc | Agentes terapéuticos dirigidos a gpr35 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3819631A (en) * | 1970-12-15 | 1974-06-25 | May & Baker Ltd | Azapurinones |
| GB1421970A (en) * | 1973-06-12 | 1976-01-21 | May & Baker Ltd | 8-azapurin-6-one derivatives |
| GB1493685A (en) * | 1970-12-15 | 1977-11-30 | May & Baker Ltd | 8-azapurinones |
| US4052390A (en) * | 1973-06-12 | 1977-10-04 | May & Baker Limited | Azapurinones |
-
1976
- 1976-10-22 GB GB44008/76A patent/GB1561345A/en not_active Expired
-
1977
- 1977-10-14 NL NL7711332A patent/NL7711332A/xx not_active Application Discontinuation
- 1977-10-19 HU HU77MA2922A patent/HU180009B/hu unknown
- 1977-10-20 US US05/843,786 patent/US4167568A/en not_active Expired - Lifetime
- 1977-10-20 IE IE2139/77A patent/IE45810B1/en unknown
- 1977-10-20 ZA ZA00776258A patent/ZA776258B/xx unknown
- 1977-10-20 AU AU29911/77A patent/AU510478B2/en not_active Expired
- 1977-10-20 SE SE7711836A patent/SE7711836L/xx not_active Application Discontinuation
- 1977-10-20 DE DE19772747199 patent/DE2747199A1/de not_active Withdrawn
- 1977-10-20 DK DK467177AA patent/DK142766B/da not_active IP Right Cessation
- 1977-10-20 JP JP12634477A patent/JPS5395993A/ja active Pending
- 1977-10-21 CA CA289,249A patent/CA1111027A/fr not_active Expired
- 1977-10-21 BE BE181957A patent/BE859987A/xx not_active IP Right Cessation
- 1977-10-21 LU LU78363A patent/LU78363A1/xx unknown
- 1977-10-21 CH CH1286877A patent/CH628898A5/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE7711836L (sv) | 1978-04-23 |
| LU78363A1 (show.php) | 1978-06-12 |
| AU510478B2 (en) | 1980-06-26 |
| US4167568A (en) | 1979-09-11 |
| ZA776258B (en) | 1978-07-26 |
| NL7711332A (nl) | 1978-04-25 |
| AU2991177A (en) | 1979-04-26 |
| GB1561345A (en) | 1980-02-20 |
| BE859987A (fr) | 1978-04-21 |
| IE45810L (en) | 1978-04-22 |
| DE2747199A1 (de) | 1978-04-27 |
| DK467177A (show.php) | 1978-04-23 |
| DK142766C (show.php) | 1981-08-17 |
| JPS5395993A (en) | 1978-08-22 |
| CH628898A5 (fr) | 1982-03-31 |
| IE45810B1 (en) | 1982-12-01 |
| DK142766B (da) | 1981-01-19 |
| CA1111027A (fr) | 1981-10-20 |
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