SU1588283A3 - Способ получени производных хиназолина или их солей - Google Patents
Способ получени производных хиназолина или их солей Download PDFInfo
- Publication number
- SU1588283A3 SU1588283A3 SU864028362A SU4028362A SU1588283A3 SU 1588283 A3 SU1588283 A3 SU 1588283A3 SU 864028362 A SU864028362 A SU 864028362A SU 4028362 A SU4028362 A SU 4028362A SU 1588283 A3 SU1588283 A3 SU 1588283A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- singlet
- cooh
- spectrum
- tetrahydro
- acetic acid
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims abstract description 5
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title claims abstract 5
- 238000000034 method Methods 0.000 title description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract 6
- 150000002367 halogens Chemical class 0.000 claims abstract 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract 2
- 230000007062 hydrolysis Effects 0.000 claims abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract 2
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 239000003814 drug Substances 0.000 abstract description 7
- 102000016912 Aldehyde Reductase Human genes 0.000 abstract description 3
- 108010053754 Aldehyde reductase Proteins 0.000 abstract description 3
- 208000002177 Cataract Diseases 0.000 abstract description 3
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 201000001119 neuropathy Diseases 0.000 abstract description 3
- 230000007823 neuropathy Effects 0.000 abstract description 3
- 208000033808 peripheral neuropathy Diseases 0.000 abstract description 3
- 231100000331 toxic Toxicity 0.000 abstract description 3
- 230000002588 toxic effect Effects 0.000 abstract description 3
- 208000002249 Diabetes Complications Diseases 0.000 abstract description 2
- 206010012655 Diabetic complications Diseases 0.000 abstract description 2
- 208000017442 Retinal disease Diseases 0.000 abstract description 2
- 206010038923 Retinopathy Diseases 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 208000017169 kidney disease Diseases 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 210000004087 cornea Anatomy 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 230000029663 wound healing Effects 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 76
- 238000002329 infrared spectrum Methods 0.000 description 44
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 44
- -1 (4-Bromo-2-fluorobenzyl) - Chemical class 0.000 description 31
- 239000000243 solution Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 241000700159 Rattus Species 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 206010012601 diabetes mellitus Diseases 0.000 description 6
- 210000003497 sciatic nerve Anatomy 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000600 sorbitol Substances 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- SWGAGHWDWIDITD-UHFFFAOYSA-N 2-(3-benzyl-4-oxo-2-sulfanylidenequinazolin-1-yl)acetic acid Chemical compound S=C1N(CC(=O)O)C2=CC=CC=C2C(=O)N1CC1=CC=CC=C1 SWGAGHWDWIDITD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 102000004316 Oxidoreductases Human genes 0.000 description 2
- 108090000854 Oxidoreductases Proteins 0.000 description 2
- ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 150000001323 aldoses Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000007824 enzymatic assay Methods 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- INHCSSUBVCNVSK-UHFFFAOYSA-L lithium sulfate Inorganic materials [Li+].[Li+].[O-]S([O-])(=O)=O INHCSSUBVCNVSK-UHFFFAOYSA-L 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229950006238 nadide Drugs 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 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 2
- 229960001052 streptozocin Drugs 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 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 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- MLQXNJCIGWKSPF-UHFFFAOYSA-N 2-(2,4-dioxoquinazolin-1-yl)acetic acid Chemical compound C1=CC=C2C(=O)NC(=O)N(CC(=O)O)C2=C1 MLQXNJCIGWKSPF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- MNQZXJOMYWMBOU-GSVOUGTGSA-N L-(-)-glyceraldehyde Chemical compound OC[C@H](O)C=O MNQZXJOMYWMBOU-GSVOUGTGSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- OKKJLVBELUTLKV-MICDWDOJSA-N deuteriomethanol Chemical compound [2H]CO OKKJLVBELUTLKV-MICDWDOJSA-N 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000004175 fluorobenzyl group Chemical group 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000003462 vein Anatomy 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)
- Obesity (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Reproductive Health (AREA)
- Gastroenterology & Hepatology (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB858524663A GB8524663D0 (en) | 1985-10-07 | 1985-10-07 | Quinazoline derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1588283A3 true SU1588283A3 (ru) | 1990-08-23 |
Family
ID=10586291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU864028362A SU1588283A3 (ru) | 1985-10-07 | 1986-10-03 | Способ получени производных хиназолина или их солей |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US4734419A (https=) |
| EP (1) | EP0218999B1 (https=) |
| JP (3) | JPS6296476A (https=) |
| KR (1) | KR940007270B1 (https=) |
| CN (1) | CN1017242B (https=) |
| AT (1) | ATE60761T1 (https=) |
| AU (1) | AU596611B2 (https=) |
| CA (1) | CA1289139C (https=) |
| DE (1) | DE3677452D1 (https=) |
| DK (1) | DK158838C (https=) |
| ES (1) | ES2021266B3 (https=) |
| FI (1) | FI90234C (https=) |
| GB (1) | GB8524663D0 (https=) |
| GR (1) | GR3001502T3 (https=) |
| HK (1) | HK6993A (https=) |
| HU (1) | HU196972B (https=) |
| IE (1) | IE59309B1 (https=) |
| IL (1) | IL80213A (https=) |
| NO (1) | NO171785C (https=) |
| SG (1) | SG112092G (https=) |
| SU (1) | SU1588283A3 (https=) |
| UA (1) | UA5562A1 (https=) |
| ZA (1) | ZA867043B (https=) |
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 |
| EP0335979A4 (en) * | 1987-09-16 | 1992-02-26 | Taiho Pharmaceutical Company, Limited | Thienopyrimidine derivatives |
| 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 |
| US5728704A (en) * | 1992-09-28 | 1998-03-17 | Pfizer Inc. | Substituted pyridmidines for control of diabetic complications |
| DE19532052C2 (de) * | 1995-08-31 | 1998-11-19 | Clariant Gmbh | Verfahren zur Herstellung von Chinazolinderivaten |
| US5973189A (en) * | 1995-08-31 | 1999-10-26 | Clariant Gmbh | Monoesters of carboxymethylene anthranilic acids and process for preparing the same |
| CA2193932C (en) * | 1995-12-26 | 2001-08-21 | Shinji Nishii | Process for producing isatoic anhydrides |
| US6201121B1 (en) | 1995-12-28 | 2001-03-13 | Fuji Chemical Industry Co., Ltd. | Process for the preparation of 3-dihalobenzyl-2,4-quinazolinedione derivatives |
| CA2196510C (en) * | 1996-02-01 | 2000-08-01 | Masashi Komatsu | Process for producing dioxoquinazolines |
| DE19650975A1 (de) * | 1996-12-09 | 1998-06-10 | Basf Ag | Neue heterocyclisch substituierte Benzamide und deren Anwendung |
| GB2338235B (en) * | 1997-04-15 | 2001-11-14 | Csir | Appetite suppressing plant extracts |
| US6444816B1 (en) | 1997-10-27 | 2002-09-03 | Dr. Reddy's Research Foundation | Fused 7-oxo-pyrimidinyl compounds, preparation, composition and use thereof |
| EP1004307B1 (en) * | 1998-01-30 | 2002-09-04 | R-Tech Ueno, Ltd. | Ophthalmic composition |
| WO2000043015A1 (fr) * | 1999-01-25 | 2000-07-27 | Fujisawa Pharmaceutical Co., Ltd. | Gouttes ophtalmologiques |
| JP2003516309A (ja) * | 1999-02-18 | 2003-05-13 | 株式会社アールテック・ウエノ | 涙液分泌障害を除く外分泌障害処置剤 |
| KR20020011966A (ko) * | 1999-03-09 | 2002-02-09 | 후지야마 아키라 | 퀴나졸린 유도체 또는 그의 염의 제조법 |
| GB2355657B (en) * | 1999-10-27 | 2004-07-28 | Phytopharm Plc | Inhibitors Of Gastric Acid Secretion |
| 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 |
| WO2002043763A2 (en) | 2000-11-30 | 2002-06-06 | Pfizer Products Inc. | Combination of gaba agonists and aldose reductase inhibitors |
| 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 |
| JP2005529076A (ja) * | 2002-02-15 | 2005-09-29 | サイトキネティクス・インコーポレーテッド | キナゾリノンの合成 |
| EP2316468A1 (en) | 2002-02-22 | 2011-05-04 | Shire LLC | Delivery system and methods for protecting and administering dextroamphetamine |
| EP1553931A4 (en) | 2002-05-09 | 2006-08-30 | Cytokinetics Inc | COMPOUNDS, COMPOSITIONS AND METHODS |
| RU2004135554A (ru) * | 2002-05-09 | 2006-01-20 | Цитокинетикс, Инк. (Us) | Пиримидиноны, композиции на их основе и способы их использования |
| US20040053948A1 (en) * | 2002-05-10 | 2004-03-18 | Cytokinetics, Inc. | Compounds, compositions and methods |
| EP1513820A4 (en) * | 2002-05-23 | 2006-09-13 | Cytokinetics Inc | COMPOUNDS, COMPOSITIONS AND METHODS |
| CA2489367A1 (en) * | 2002-06-14 | 2003-12-24 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| EP1537089A4 (en) * | 2002-07-23 | 2008-04-16 | Cytokinetics Inc | CONNECTIONS, COMPOSITIONS AND PROCEDURES |
| WO2004018058A2 (en) * | 2002-08-21 | 2004-03-04 | Cytokinetics, Inc. | 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 |
| JP2007510660A (ja) * | 2003-11-07 | 2007-04-26 | サイトキネティクス・インコーポレーテッド | 化合物、組成物及び方法 |
| 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 |
| CA2656357C (en) * | 2006-07-19 | 2014-05-06 | E.I. Du Pont De Nemours And Company | Process for making 3-substituted 2-amino-5-halobenzamides |
| US8877717B2 (en) | 2007-03-12 | 2014-11-04 | Zadec Aps | Anti-diabetic extract of rooibos |
| EP2848252A3 (en) | 2007-03-23 | 2015-06-17 | The Board of Regents of the University of Texas System | Aldose reductase inhibitors for use in treating uveitis |
| JP5341084B2 (ja) * | 2007-08-03 | 2013-11-13 | エフ．ホフマン−ラ ロシュ アーゲー | Ｔａａｒ１リガンドとしてのピリジンカルボキシアミド及びベンズアミド誘導体 |
| 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 |
| EP2994139B1 (en) | 2013-05-10 | 2019-04-10 | Gilead Apollo, LLC | Acc inhibitors and uses thereof |
| JP6417401B2 (ja) | 2013-05-10 | 2018-11-07 | ギリアド アポロ， エルエルシー | Ａｃｃ阻害剤及びその使用 |
| AU2014262547A1 (en) | 2013-05-10 | 2015-11-26 | Gilead Apollo, Llc | 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1491510A (en) * | 1973-12-14 | 1977-11-09 | Hisamitsu Pharmaceutical Co | 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 |
| EP0040793B1 (en) * | 1980-05-22 | 1985-08-28 | 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 US US06/908,005 patent/US4734419A/en not_active Expired - Lifetime
- 1986-09-16 ZA ZA867043A patent/ZA867043B/xx unknown
- 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 AT AT86113559T patent/ATE60761T1/de not_active IP Right Cessation
- 1986-10-02 IL IL80213A patent/IL80213A/xx not_active IP Right Cessation
- 1986-10-02 ES ES86113559T patent/ES2021266B3/es not_active Expired - Lifetime
- 1986-10-03 SU SU864028362A patent/SU1588283A3/ru active
- 1986-10-03 CA CA000519759A patent/CA1289139C/en not_active Expired - Fee Related
- 1986-10-03 UA UA4028362A patent/UA5562A1/uk unknown
- 1986-10-06 AU AU63589/86A patent/AU596611B2/en not_active Ceased
- 1986-10-06 NO NO863980A patent/NO171785C/no not_active IP Right Cessation
- 1986-10-06 HU HU864192A patent/HU196972B/hu not_active IP Right Cessation
- 1986-10-06 JP JP61237605A patent/JPS6296476A/ja active Granted
- 1986-10-07 KR KR86008374A patent/KR940007270B1/ko not_active Expired - Fee Related
- 1986-10-07 CN CN86106984A patent/CN1017242B/zh not_active Expired
-
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
Non-Patent Citations (1)
| Title |
|---|
| Патент DE № 2652144, кл. С 07 D 239/96, опублик. 18.05.78. Бюл ер К., Пирсон Д. Органические синтезы. Т. 2. - М.: Мир, 1973, с. 223-227.,, * |
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