JPH05366B2 - - Google Patents
Info
- Publication number
- JPH05366B2 JPH05366B2 JP63207571A JP20757188A JPH05366B2 JP H05366 B2 JPH05366 B2 JP H05366B2 JP 63207571 A JP63207571 A JP 63207571A JP 20757188 A JP20757188 A JP 20757188A JP H05366 B2 JPH05366 B2 JP H05366B2
- Authority
- JP
- Japan
- Prior art keywords
- tetrahydro
- bromo
- dioxoquinazolin
- fluorobenzyl
- nmr
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000003288 aldose reductase inhibitor Substances 0.000 claims description 5
- 229940118148 Aldose reductase inhibitor Drugs 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 55
- 238000000034 method Methods 0.000 abstract description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 5
- 125000001475 halogen functional group Chemical group 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 239000001301 oxygen Substances 0.000 abstract description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 abstract 1
- -1 inorganic base salts Chemical class 0.000 description 64
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 34
- 239000000203 mixture Substances 0.000 description 31
- 238000004519 manufacturing process Methods 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 239000002253 acid Chemical group 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000001816 cooling Methods 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 150000003246 quinazolines Chemical class 0.000 description 9
- ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 8
- 229960001052 streptozocin Drugs 0.000 description 8
- 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 7
- 235000011054 acetic acid Nutrition 0.000 description 7
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 7
- 210000003497 sciatic nerve Anatomy 0.000 description 7
- 239000000600 sorbitol Substances 0.000 description 7
- 102000016912 Aldehyde Reductase Human genes 0.000 description 6
- 108010053754 Aldehyde reductase Proteins 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 230000002411 adverse Effects 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- GBMBFYYGBBVEGT-UHFFFAOYSA-N 2-[3-[(2-fluoro-4-iodophenyl)methyl]-2,4-dioxoquinazolin-1-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C2=CC=CC=C2C(=O)N1CC1=CC=C(I)C=C1F GBMBFYYGBBVEGT-UHFFFAOYSA-N 0.000 description 3
- CQQITEUCHFMHBS-UHFFFAOYSA-N 2-[3-[(4-bromo-2-fluorophenyl)methyl]-2,4-dioxoquinazolin-1-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C2=CC=CC=C2C(=O)N1CC1=CC=C(Br)C=C1F CQQITEUCHFMHBS-UHFFFAOYSA-N 0.000 description 3
- SXEPCMGMVAWKLM-UHFFFAOYSA-N 2-[3-[(4-bromo-2-fluorophenyl)methyl]-7-methoxy-2,4-dioxoquinazolin-1-yl]acetic acid Chemical compound C=1C(OC)=CC=C(C2=O)C=1N(CC(O)=O)C(=O)N2CC1=CC=C(Br)C=C1F SXEPCMGMVAWKLM-UHFFFAOYSA-N 0.000 description 3
- FQUMHBXENNAXTG-UHFFFAOYSA-N 2-[7-bromo-3-[(4-bromo-2-fluorophenyl)methyl]-2,4-dioxoquinazolin-1-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C2=CC(Br)=CC=C2C(=O)N1CC1=CC=C(Br)C=C1F FQUMHBXENNAXTG-UHFFFAOYSA-N 0.000 description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
- 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229940092714 benzenesulfonic acid Drugs 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 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 3
- 238000001647 drug administration Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- SXONDGSPUVNZLO-UHFFFAOYSA-N zenarestat Chemical compound O=C1N(CC(=O)O)C2=CC(Cl)=CC=C2C(=O)N1CC1=CC=C(Br)C=C1F SXONDGSPUVNZLO-UHFFFAOYSA-N 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- RLTFBWCBGIZCDQ-UHFFFAOYSA-N (4-bromo-2-fluorophenyl)methanamine Chemical compound NCC1=CC=C(Br)C=C1F RLTFBWCBGIZCDQ-UHFFFAOYSA-N 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- CGUJPDPCPMHNOI-UHFFFAOYSA-N 2-[3-[(2,3-dichlorophenyl)methyl]-2,4-dioxoquinazolin-1-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C2=CC=CC=C2C(=O)N1CC1=CC=CC(Cl)=C1Cl CGUJPDPCPMHNOI-UHFFFAOYSA-N 0.000 description 2
- DNTSYFXIUZDXFS-UHFFFAOYSA-N 2-[3-[(2,4-dichlorophenyl)methyl]-2,4-dioxoquinazolin-1-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C2=CC=CC=C2C(=O)N1CC1=CC=C(Cl)C=C1Cl DNTSYFXIUZDXFS-UHFFFAOYSA-N 0.000 description 2
- AJUXANYDJWYIDV-UHFFFAOYSA-N 2-[3-[(2-fluoro-4-iodophenyl)methyl]-7-iodo-2,4-dioxoquinazolin-1-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C2=CC(I)=CC=C2C(=O)N1CC1=CC=C(I)C=C1F AJUXANYDJWYIDV-UHFFFAOYSA-N 0.000 description 2
- BKDOBPYOBVPQNV-UHFFFAOYSA-N 2-[3-[(3,4-dichlorophenyl)methyl]-2,4-dioxoquinazolin-1-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C2=CC=CC=C2C(=O)N1CC1=CC=C(Cl)C(Cl)=C1 BKDOBPYOBVPQNV-UHFFFAOYSA-N 0.000 description 2
- SMZPIUPUPYXXLZ-UHFFFAOYSA-N 2-[3-[(3,4-dichlorophenyl)methyl]-2,4-dioxoquinazolin-1-yl]propanoic acid Chemical compound O=C1N(C(C(O)=O)C)C2=CC=CC=C2C(=O)N1CC1=CC=C(Cl)C(Cl)=C1 SMZPIUPUPYXXLZ-UHFFFAOYSA-N 0.000 description 2
- VFWLWNUNOROOEK-UHFFFAOYSA-N 2-[3-[(3,5-dichlorophenyl)methyl]-2,4-dioxoquinazolin-1-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C2=CC=CC=C2C(=O)N1CC1=CC(Cl)=CC(Cl)=C1 VFWLWNUNOROOEK-UHFFFAOYSA-N 0.000 description 2
- YBLVHVBDTNDCLM-UHFFFAOYSA-N 2-[3-[(4-bromo-2-fluorophenyl)methyl]-5-chloro-2,4-dioxoquinazolin-1-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C2=CC=CC(Cl)=C2C(=O)N1CC1=CC=C(Br)C=C1F YBLVHVBDTNDCLM-UHFFFAOYSA-N 0.000 description 2
- UAXXNQCAAFXUQN-UHFFFAOYSA-N 2-[3-[(4-bromo-2-fluorophenyl)methyl]-5-methoxy-2,4-dioxoquinazolin-1-yl]acetic acid Chemical compound O=C1C=2C(OC)=CC=CC=2N(CC(O)=O)C(=O)N1CC1=CC=C(Br)C=C1F UAXXNQCAAFXUQN-UHFFFAOYSA-N 0.000 description 2
- UPJGFOSISGFIHV-UHFFFAOYSA-N 2-[3-[(4-bromo-2-fluorophenyl)methyl]-6-chloro-2,4-dioxoquinazolin-1-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C2=CC=C(Cl)C=C2C(=O)N1CC1=CC=C(Br)C=C1F UPJGFOSISGFIHV-UHFFFAOYSA-N 0.000 description 2
- RGDBMMUKMLRWFI-UHFFFAOYSA-N 2-[3-[(4-bromo-2-fluorophenyl)methyl]-6-methoxy-2,4-dioxoquinazolin-1-yl]acetic acid Chemical compound O=C1C2=CC(OC)=CC=C2N(CC(O)=O)C(=O)N1CC1=CC=C(Br)C=C1F RGDBMMUKMLRWFI-UHFFFAOYSA-N 0.000 description 2
- XLOHSVVOWVIPFC-UHFFFAOYSA-N 2-[3-[(4-bromo-2-fluorophenyl)methyl]-7-fluoro-2,4-dioxoquinazolin-1-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C2=CC(F)=CC=C2C(=O)N1CC1=CC=C(Br)C=C1F XLOHSVVOWVIPFC-UHFFFAOYSA-N 0.000 description 2
- PEAGERJCSHJISQ-UHFFFAOYSA-N 2-[3-[(4-bromo-2-fluorophenyl)methyl]-7-iodo-2,4-dioxoquinazolin-1-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C2=CC(I)=CC=C2C(=O)N1CC1=CC=C(Br)C=C1F PEAGERJCSHJISQ-UHFFFAOYSA-N 0.000 description 2
- SFMBOIYZKMXWEH-UHFFFAOYSA-N 2-[3-[(4-bromo-2-fluorophenyl)methyl]-8-chloro-2,4-dioxoquinazolin-1-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C2=C(Cl)C=CC=C2C(=O)N1CC1=CC=C(Br)C=C1F SFMBOIYZKMXWEH-UHFFFAOYSA-N 0.000 description 2
- OOLPNEMOORMNRC-UHFFFAOYSA-N 2-[3-[(4-bromo-2-fluorophenyl)methyl]-8-methoxy-2,4-dioxoquinazolin-1-yl]acetic acid Chemical compound COC1=CC=CC(C2=O)=C1N(CC(O)=O)C(=O)N2CC1=CC=C(Br)C=C1F OOLPNEMOORMNRC-UHFFFAOYSA-N 0.000 description 2
- DFZPFLMGYYCKPR-UHFFFAOYSA-N 2-[3-[(4-bromo-3-chlorophenyl)methyl]-2,4-dioxoquinazolin-1-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C2=CC=CC=C2C(=O)N1CC1=CC=C(Br)C(Cl)=C1 DFZPFLMGYYCKPR-UHFFFAOYSA-N 0.000 description 2
- ZLFIJGYGVXCDLI-UHFFFAOYSA-N 2-[3-[(4-chloro-2-fluorophenyl)methyl]-2,4-dioxoquinazolin-1-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C2=CC=CC=C2C(=O)N1CC1=CC=C(Cl)C=C1F ZLFIJGYGVXCDLI-UHFFFAOYSA-N 0.000 description 2
- SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 2
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- SSUDQIXBUJCZPX-UHFFFAOYSA-M sodium;2-[3-[(4-bromo-2-fluorophenyl)methyl]-7-chloro-2,4-dioxoquinazolin-1-yl]acetate Chemical compound [Na+].O=C1N(CC(=O)[O-])C2=CC(Cl)=CC=C2C(=O)N1CC1=CC=C(Br)C=C1F SSUDQIXBUJCZPX-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- KUYMVWXKHQSIAS-UHFFFAOYSA-N tert-butyl 2-chloroacetate Chemical compound CC(C)(C)OC(=O)CCl KUYMVWXKHQSIAS-UHFFFAOYSA-N 0.000 description 1
- RBTVSNLYYIMMKS-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)N1CC(N)C1 RBTVSNLYYIMMKS-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/12—Ophthalmic agents for cataracts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
- C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
- C07D285/22—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D285/24—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Ophthalmology & Optometry (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Gastroenterology & Hepatology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Reproductive Health (AREA)
- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8524663 | 1985-10-07 | ||
| GB858524663A GB8524663D0 (en) | 1985-10-07 | 1985-10-07 | Quinazoline derivatives |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61237605A Division JPS6296476A (ja) | 1985-10-07 | 1986-10-06 | キナゾリン誘導体及びその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01125322A JPH01125322A (ja) | 1989-05-17 |
| JPH05366B2 true JPH05366B2 (enExample) | 1993-01-05 |
Family
ID=10586291
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61237605A Granted JPS6296476A (ja) | 1985-10-07 | 1986-10-06 | キナゾリン誘導体及びその製造方法 |
| JP63207570A Expired - Lifetime JPH0794447B2 (ja) | 1985-10-07 | 1988-08-22 | キナゾリン誘導体 |
| JP63207571A Granted JPH01125322A (ja) | 1985-10-07 | 1988-08-22 | アルドース還元酵素阻害剤 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61237605A Granted JPS6296476A (ja) | 1985-10-07 | 1986-10-06 | キナゾリン誘導体及びその製造方法 |
| JP63207570A Expired - Lifetime JPH0794447B2 (ja) | 1985-10-07 | 1988-08-22 | キナゾリン誘導体 |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US4734419A (enExample) |
| EP (1) | EP0218999B1 (enExample) |
| JP (3) | JPS6296476A (enExample) |
| KR (1) | KR940007270B1 (enExample) |
| CN (1) | CN1017242B (enExample) |
| AT (1) | ATE60761T1 (enExample) |
| AU (1) | AU596611B2 (enExample) |
| CA (1) | CA1289139C (enExample) |
| DE (1) | DE3677452D1 (enExample) |
| DK (1) | DK158838C (enExample) |
| ES (1) | ES2021266B3 (enExample) |
| FI (1) | FI90234C (enExample) |
| GB (1) | GB8524663D0 (enExample) |
| GR (1) | GR3001502T3 (enExample) |
| HK (1) | HK6993A (enExample) |
| HU (1) | HU196972B (enExample) |
| IE (1) | IE59309B1 (enExample) |
| IL (1) | IL80213A (enExample) |
| NO (1) | NO171785C (enExample) |
| SG (1) | SG112092G (enExample) |
| SU (1) | SU1588283A3 (enExample) |
| UA (1) | UA5562A1 (enExample) |
| ZA (1) | ZA867043B (enExample) |
Families Citing this family (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8524663D0 (en) * | 1985-10-07 | 1985-11-13 | Fujisawa Pharmaceutical Co | Quinazoline derivatives |
| WO1988001270A1 (en) * | 1986-08-21 | 1988-02-25 | Pfizer Inc. | Pyridopyrimidinediones |
| US4889851A (en) * | 1986-11-21 | 1989-12-26 | Fujisawa Pharmaceutical Co, Ltd. | Benzothiadiazine compounds, and pharmaceutical composition comprising the same |
| US4931440A (en) * | 1987-07-29 | 1990-06-05 | Fujisawa Pharmaceutical Company, Ltd. | Uricosuric composition |
| US4898867A (en) * | 1987-09-16 | 1990-02-06 | Taiho Pharmaceutical Company, Limited | Thienopyrimidine derivaties as aldose-reductase inhibitors |
| JP2621460B2 (ja) * | 1988-02-29 | 1997-06-18 | 藤沢薬品工業株式会社 | 利尿または降圧剤 |
| US5324747A (en) * | 1992-07-15 | 1994-06-28 | Hoffmann-La Roche Inc. | N-substituted anilines, inhibitors of phospholipases A2 |
| KR950703539A (ko) * | 1992-09-28 | 1995-09-20 | 알렌 제이. 스피겔 | 당뇨병 합병증 치료용 치환된 피리미딘(substituted pyrimidines for control or diabetic complications) |
| EP0847382B1 (de) * | 1995-08-31 | 2000-12-20 | Clariant GmbH | Monoester der carboxymethylenanthranilsäuren und verfahren zu ihrer herstellung |
| DE19532052C2 (de) * | 1995-08-31 | 1998-11-19 | Clariant Gmbh | Verfahren zur Herstellung von Chinazolinderivaten |
| CA2193932C (en) * | 1995-12-26 | 2001-08-21 | Shinji Nishii | Process for producing isatoic anhydrides |
| WO1997024335A1 (en) * | 1995-12-28 | 1997-07-10 | Fuji Chemical Industry Co., Ltd. | Process for the preparation of 3-dihalobenzyl-2,4-quinazolinedione derivatives |
| DE69701647T2 (de) * | 1996-02-01 | 2000-09-07 | Sumitomo Chemical Co., Ltd. | Verfahren zur Herstellung von Dioxochinazolinen |
| DE19650975A1 (de) * | 1996-12-09 | 1998-06-10 | Basf Ag | Neue heterocyclisch substituierte Benzamide und deren Anwendung |
| ES2363230T3 (es) * | 1997-04-15 | 2011-07-27 | Csir | Métodos no terapéuticos para suprimir el apetito. |
| US6444816B1 (en) | 1997-10-27 | 2002-09-03 | Dr. Reddy's Research Foundation | Fused 7-oxo-pyrimidinyl compounds, preparation, composition and use thereof |
| TR200002209T2 (tr) | 1998-01-30 | 2000-11-21 | R-Tech Ueno, Ltd. | Oftalmik bileşim. |
| WO2000043015A1 (fr) * | 1999-01-25 | 2000-07-27 | Fujisawa Pharmaceutical Co., Ltd. | Gouttes ophtalmologiques |
| BR0005010A (pt) | 1999-02-18 | 2002-03-19 | R Tech Ueno Ltd | Composição para tratamento de distúrbios de secreção externa exceto a hipolacrimação e seu uso |
| AU2830700A (en) * | 1999-03-09 | 2000-09-28 | Fujisawa Pharmaceutical Co., Ltd. | Process for producing quinazoline derivative or salt thereof |
| GB2396815B (en) * | 1999-10-27 | 2004-09-08 | Phytopharm Plc | A composition comprising a pregnenone derivative and an NSAID |
| US7230000B1 (en) | 1999-10-27 | 2007-06-12 | Cytokinetics, Incorporated | Methods and compositions utilizing quinazolinones |
| US6545004B1 (en) * | 1999-10-27 | 2003-04-08 | Cytokinetics, Inc. | Methods and compositions utilizing quinazolinones |
| US6380200B1 (en) | 1999-12-07 | 2002-04-30 | Pfizer, Inc. | Combination of aldose reductase inhibitors and selective serotonin reuptake inhibitors for the treatment of diabetic complications |
| GB2363985B (en) | 2000-06-30 | 2004-09-29 | Phytopharm Plc | Extracts,compounds & pharmaceutical compositions having anti-diabetic activity and their use |
| CN1477976A (zh) | 2000-11-30 | 2004-02-25 | �Ʒ� | Gaba激动剂与醛糖还原酶抑制剂的组合 |
| WO2002098462A1 (en) * | 2001-06-01 | 2002-12-12 | Ono Pharmaceutical Co., Ltd. | Remedies containing aldose reductase inhibitor as the active ingredient for demyelinating diseases or diseases associated with demyelination |
| CA2475879A1 (en) * | 2002-02-15 | 2003-08-28 | Cytokinetics, Inc. | Synthesis of quinazolinones |
| JP4625637B2 (ja) | 2002-02-22 | 2011-02-02 | シャイア エルエルシー | 活性物質送達系及び活性物質を保護し投与する方法 |
| JP2006508030A (ja) * | 2002-05-09 | 2006-03-09 | サイトキネティクス・インコーポレーテッド | ピリミジノン化合物、組成物および方法 |
| WO2003097053A1 (en) | 2002-05-09 | 2003-11-27 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| WO2004026226A2 (en) * | 2002-05-10 | 2004-04-01 | Cytokinetics, Inc. | Compounds, compositions and methods |
| AU2003265242A1 (en) * | 2002-05-23 | 2003-12-22 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| US7041676B2 (en) * | 2002-06-14 | 2006-05-09 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| AU2003256805A1 (en) * | 2002-07-23 | 2004-02-09 | Cytokinetics, Inc. | Compounds compositions and methods |
| US20040048853A1 (en) * | 2002-08-21 | 2004-03-11 | Gustave Bergnes | Compounds, compositions, and methods |
| WO2004034972A2 (en) * | 2002-09-30 | 2004-04-29 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| WO2005041888A2 (en) * | 2003-11-03 | 2005-05-12 | Cytokinetics, Inc. | Pyrimidin-4-one compounds, compositions and methods |
| EP1680420A4 (en) * | 2003-11-07 | 2008-09-24 | Cytokinetics Inc | COMPOUNDS, COMPOSITIONS AND METHODS |
| EP1692112A4 (en) * | 2003-12-08 | 2008-09-24 | Cytokinetics Inc | COMPOUNDS, COMPOSITIONS, AND METHODS |
| US20070010537A1 (en) * | 2004-08-20 | 2007-01-11 | Kazumasa Hamamura | Fused pyramidine derivative and use thereof |
| US20110092566A1 (en) * | 2004-11-19 | 2011-04-21 | Srivastava Satish K | Treatment of cancer with aldose reductase inhibitors |
| EP2044002B1 (en) * | 2006-07-19 | 2014-04-16 | E.I. Du Pont De Nemours And Company | Process for making 3-substituted 2-amino-5-halobenzamides |
| WO2008110551A1 (en) | 2007-03-12 | 2008-09-18 | Zadec Aps | An anti-diabetic extract of rooibos |
| WO2008118844A1 (en) | 2007-03-23 | 2008-10-02 | The Board Of Regents Of The University Of Texas System | Methods involving aldose reductase inhibitors |
| CN101784515A (zh) * | 2007-08-03 | 2010-07-21 | 弗·哈夫曼-拉罗切有限公司 | 作为taar1配体的吡啶甲酰胺和苯甲酰胺衍生物 |
| US20090270490A1 (en) * | 2008-04-24 | 2009-10-29 | The Board Of Regents Of The University Of Texas System | Methods involving aldose reductase inhibition |
| CN102219759B (zh) * | 2010-04-16 | 2013-07-24 | 中国科学院上海药物研究所 | 芳基甲酰胺类化合物及其制备方法、药物组合物和用途 |
| WO2012088525A2 (en) | 2010-12-23 | 2012-06-28 | The Board Of Regents Of The University Of Texas System | Methods for treating copd |
| AU2014262636A1 (en) | 2013-05-10 | 2015-11-26 | Gilead Apollo, Llc | ACC inhibitors and uses thereof |
| JP6434498B2 (ja) | 2013-05-10 | 2018-12-05 | ギリアド アポロ， エルエルシー | Ａｃｃ阻害剤及びその使用 |
| WO2014182951A1 (en) | 2013-05-10 | 2014-11-13 | Nimbus Apollo, Inc. | Acc inhibitors and uses thereof |
| TW201623257A (zh) | 2014-05-09 | 2016-07-01 | 奧利安公司 | 藥理活性之喹唑啉二酮衍生物 |
| WO2019165195A1 (en) | 2018-02-22 | 2019-08-29 | Srivastava Satish | Combination therapy for the treatment of cancer |
| CN111499616B (zh) * | 2020-05-07 | 2022-07-22 | 盐城工学院 | 一种芳杂环取代的喹唑啉酮衍生物及其合成方法与应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4016166A (en) * | 1973-12-14 | 1977-04-05 | Hisamitsu Pharmaceutical Co., Inc. | 1-Nitrophenylquinazoline-2,4(1H,3H)-diones |
| DE2652144A1 (de) * | 1976-11-16 | 1978-05-18 | Merck Patent Gmbh | Neue chinazolindione |
| CA1161036A (en) * | 1980-05-15 | 1984-01-24 | Masayuki Ishikawa | Quinazoline-dione compounds, process for production thereof and pharmaceutical use thereof |
| DE3172006D1 (en) * | 1980-05-22 | 1985-10-03 | Masayuki Ishikawa | Novel quinazoline-dione compounds, process for production thereof and pharmaceutical use thereof |
| JPS58159480A (ja) * | 1982-03-17 | 1983-09-21 | Chugai Pharmaceut Co Ltd | 新規なフエニルピペラジン誘導体 |
| DD232702A1 (de) * | 1982-09-20 | 1986-02-05 | Adw Ddr | Verfahren zur herstellung von 1,2,3,4-tetrahydrochinazolin-2,4-dion-essigsaeuren, deren salzen und estern |
| US4490374A (en) * | 1982-09-30 | 1984-12-25 | Ortho Pharmaceutical Corporation | 5,6-Dialkoxy-3,4-optionally substituted-2(1H)quinazolinones, composition and method of use |
| JPS59186963A (ja) * | 1983-04-08 | 1984-10-23 | Chugai Pharmaceut Co Ltd | 新規なフエニルピペラジン誘導体 |
| GB8524663D0 (en) * | 1985-10-07 | 1985-11-13 | Fujisawa Pharmaceutical Co | Quinazoline derivatives |
-
1985
- 1985-10-07 GB GB858524663A patent/GB8524663D0/en active Pending
-
1986
- 1986-09-16 ZA ZA867043A patent/ZA867043B/xx unknown
- 1986-09-16 US US06/908,005 patent/US4734419A/en not_active Expired - Lifetime
- 1986-09-23 IE IE252086A patent/IE59309B1/en not_active IP Right Cessation
- 1986-09-25 DK DK459086A patent/DK158838C/da not_active IP Right Cessation
- 1986-09-29 FI FI863917A patent/FI90234C/fi not_active IP Right Cessation
- 1986-10-02 DE DE8686113559T patent/DE3677452D1/de not_active Expired - Fee Related
- 1986-10-02 EP EP86113559A patent/EP0218999B1/en not_active Expired - Lifetime
- 1986-10-02 ES ES86113559T patent/ES2021266B3/es not_active Expired - Lifetime
- 1986-10-02 IL IL80213A patent/IL80213A/xx not_active IP Right Cessation
- 1986-10-02 AT AT86113559T patent/ATE60761T1/de not_active IP Right Cessation
- 1986-10-03 UA UA4028362A patent/UA5562A1/uk unknown
- 1986-10-03 SU SU864028362A patent/SU1588283A3/ru active
- 1986-10-03 CA CA000519759A patent/CA1289139C/en not_active Expired - Fee Related
- 1986-10-06 AU AU63589/86A patent/AU596611B2/en not_active Ceased
- 1986-10-06 JP JP61237605A patent/JPS6296476A/ja active Granted
- 1986-10-06 HU HU864192A patent/HU196972B/hu not_active IP Right Cessation
- 1986-10-06 NO NO863980A patent/NO171785C/no not_active IP Right Cessation
- 1986-10-07 CN CN86106984A patent/CN1017242B/zh not_active Expired
- 1986-10-07 KR KR86008374A patent/KR940007270B1/ko not_active Expired - Fee Related
-
1987
- 1987-12-08 US US07/130,297 patent/US4883800A/en not_active Expired - Lifetime
-
1988
- 1988-08-22 JP JP63207570A patent/JPH0794447B2/ja not_active Expired - Lifetime
- 1988-08-22 JP JP63207571A patent/JPH01125322A/ja active Granted
-
1991
- 1991-02-25 GR GR90401160T patent/GR3001502T3/el unknown
-
1992
- 1992-10-27 SG SG1120/92A patent/SG112092G/en unknown
-
1993
- 1993-01-28 HK HK69/93A patent/HK6993A/en not_active IP Right Cessation
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