DK142766B - Analogifremgangsmåde til fremstilling af terapeutisk virksomme 8-azapurin-6-on-derivater. - Google Patents
Analogifremgangsmåde til fremstilling af terapeutisk virksomme 8-azapurin-6-on-derivater. Download PDFInfo
- Publication number
- DK142766B DK142766B DK467177AA DK467177A DK142766B DK 142766 B DK142766 B DK 142766B DK 467177A A DK467177A A DK 467177AA DK 467177 A DK467177 A DK 467177A DK 142766 B DK142766 B DK 142766B
- Authority
- DK
- Denmark
- Prior art keywords
- carbon atoms
- azapurin
- formula
- groups
- straight
- Prior art date
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- WTVSOESDARPVQO-UHFFFAOYSA-N triazolo[4,5-d]pyrimidin-7-one Chemical class O=C1N=CN=C2N=NN=C12 WTVSOESDARPVQO-UHFFFAOYSA-N 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000001589 carboacyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- -1 phenoxy - Chemical class 0.000 description 25
- 239000000203 mixture Substances 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 125000003545 alkoxy group Chemical group 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 229940126062 Compound A Drugs 0.000 description 6
- 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 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 6
- 241000282472 Canis lupus familiaris Species 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
- 230000037396 body weight Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 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 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000005133 alkynyloxy group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 230000000095 emetic effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 125000003884 phenylalkyl group Chemical group 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ITTXGKOHFZJUEX-UHFFFAOYSA-N 3-(ethoxymethylidene)pentane-2,4-dione Chemical compound CCOC=C(C(C)=O)C(C)=O ITTXGKOHFZJUEX-UHFFFAOYSA-N 0.000 description 2
- OCWPVOHLZYMLDJ-UHFFFAOYSA-N 3-[[4-methoxy-3-(7-oxotriazolo[4,5-d]pyrimidin-5-yl)anilino]methylidene]pentane-2,4-dione Chemical compound COC1=CC=C(NC=C(C(C)=O)C(C)=O)C=C1C1=NC(=O)C2=NN=NC2=N1 OCWPVOHLZYMLDJ-UHFFFAOYSA-N 0.000 description 2
- 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
- KCVRJRYKUKAUHJ-UHFFFAOYSA-N 5-[2-methoxy-5-(4-oxopent-2-en-2-ylamino)phenyl]triazolo[4,5-d]pyrimidin-7-one Chemical compound COC1=CC=C(NC(C)=CC(C)=O)C=C1C1=NC(=O)C2=NN=NC2=N1 KCVRJRYKUKAUHJ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 206010002198 Anaphylactic reaction Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 2
- 230000000172 allergic effect Effects 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 208000003455 anaphylaxis Diseases 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QJXWCYFTPRRCAW-UHFFFAOYSA-N ethyl 3-oxo-2-[[3-(7-oxotriazolo[4,5-d]pyrimidin-5-yl)-4-propoxyanilino]methylidene]butanoate Chemical compound CCCOC1=CC=C(NC=C(C(C)=O)C(=O)OCC)C=C1C1=NC(=O)C2=NN=NC2=N1 QJXWCYFTPRRCAW-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 208000023504 respiratory system disease Diseases 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 230000008673 vomiting Effects 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- HKQPQYGDPVVHKU-UHFFFAOYSA-N 3-[[3-(7-oxotriazolo[4,5-d]pyrimidin-5-yl)-4-propoxyanilino]methylidene]pentane-2,4-dione Chemical compound CCCOC1=CC=C(NC=C(C(C)=O)C(C)=O)C=C1C1=NC(=O)C2=NN=NC2=N1 HKQPQYGDPVVHKU-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000554155 Andes Species 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- PEJBMWVWSNVUPF-UHFFFAOYSA-N dimethyl 2-[[3-(7-oxotriazolo[4,5-d]pyrimidin-5-yl)-4-propoxyanilino]methylidene]propanedioate Chemical compound CCCOC1=CC=C(NC=C(C(=O)OC)C(=O)OC)C=C1C1=NC(=O)C2=NN=NC2=N1 PEJBMWVWSNVUPF-UHFFFAOYSA-N 0.000 description 1
- FNASCUBBFNCFQO-SOFGYWHQSA-N ethyl (2e)-2-(ethoxymethylidene)-3-oxobutanoate Chemical class CCO\C=C(/C(C)=O)C(=O)OCC FNASCUBBFNCFQO-SOFGYWHQSA-N 0.000 description 1
- KTMGNAIGXYODKQ-VOTSOKGWSA-N ethyl (e)-2-cyano-3-ethoxyprop-2-enoate Chemical class CCO\C=C(/C#N)C(=O)OCC KTMGNAIGXYODKQ-VOTSOKGWSA-N 0.000 description 1
- SUFYPNXJWUSXCI-UHFFFAOYSA-N ethyl 2-cyano-3-[3-(7-oxotriazolo[4,5-d]pyrimidin-5-yl)-4-propoxyanilino]prop-2-enoate Chemical class CCCOC1=CC=C(NC=C(C#N)C(=O)OCC)C=C1C1=NC(=O)C2=NN=NC2=N1 SUFYPNXJWUSXCI-UHFFFAOYSA-N 0.000 description 1
- RENPIZOHAOHJED-UHFFFAOYSA-N ethyl 2-ethoxycyclopentene-1-carboxylate Chemical compound CCOC(=O)C1=C(OCC)CCC1 RENPIZOHAOHJED-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- FIGTZBBYBDZDNY-UHFFFAOYSA-N n-methyl-3-(7-oxotriazolo[4,5-d]pyrimidin-5-yl)-n-propan-2-yl-4-propoxybenzenesulfonamide Chemical compound CCCOC1=CC=C(S(=O)(=O)N(C)C(C)C)C=C1C1=NC(=O)C2=NN=NC2=N1 FIGTZBBYBDZDNY-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000002071 phenylalkoxy group Chemical group 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 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
- 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
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003419 tautomerization reaction Methods 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- REZGGXNDEMKIQB-UHFFFAOYSA-N zaprinast Chemical compound CCCOC1=CC=CC=C1C1=NC(=O)C2=NNNC2=N1 REZGGXNDEMKIQB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Landscapes
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB44008/76A GB1561345A (en) | 1976-10-22 | 1976-10-22 | 8 - azapuring - 6 - ones |
| GB4400876 | 1976-10-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK467177A DK467177A (OSRAM) | 1978-04-23 |
| DK142766B true DK142766B (da) | 1981-01-19 |
| DK142766C DK142766C (OSRAM) | 1981-08-17 |
Family
ID=10431345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK467177AA DK142766B (da) | 1976-10-22 | 1977-10-20 | Analogifremgangsmåde til fremstilling af terapeutisk virksomme 8-azapurin-6-on-derivater. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4167568A (OSRAM) |
| JP (1) | JPS5395993A (OSRAM) |
| AU (1) | AU510478B2 (OSRAM) |
| BE (1) | BE859987A (OSRAM) |
| CA (1) | CA1111027A (OSRAM) |
| CH (1) | CH628898A5 (OSRAM) |
| DE (1) | DE2747199A1 (OSRAM) |
| DK (1) | DK142766B (OSRAM) |
| GB (1) | GB1561345A (OSRAM) |
| HU (1) | HU180009B (OSRAM) |
| IE (1) | IE45810B1 (OSRAM) |
| LU (1) | LU78363A1 (OSRAM) |
| NL (1) | NL7711332A (OSRAM) |
| SE (1) | SE7711836L (OSRAM) |
| ZA (1) | ZA776258B (OSRAM) |
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 (OSRAM) | 1978-06-12 |
| AU510478B2 (en) | 1980-06-26 |
| US4167568A (en) | 1979-09-11 |
| ZA776258B (en) | 1978-07-26 |
| NL7711332A (nl) | 1978-04-25 |
| HU180009B (en) | 1983-01-28 |
| 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 (OSRAM) | 1978-04-23 |
| DK142766C (OSRAM) | 1981-08-17 |
| JPS5395993A (en) | 1978-08-22 |
| CH628898A5 (fr) | 1982-03-31 |
| IE45810B1 (en) | 1982-12-01 |
| CA1111027A (fr) | 1981-10-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |