CA2778756A1 - Benzazepine compound - Google Patents
Benzazepine compound Download PDFInfo
- Publication number
- CA2778756A1 CA2778756A1 CA2778756A CA2778756A CA2778756A1 CA 2778756 A1 CA2778756 A1 CA 2778756A1 CA 2778756 A CA2778756 A CA 2778756A CA 2778756 A CA2778756 A CA 2778756A CA 2778756 A1 CA2778756 A1 CA 2778756A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- chloro
- benzo
- azepine
- methylbenzamide
- 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.)
- Abandoned
Links
- -1 Benzazepine compound Chemical class 0.000 title claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 125000005345 deuteroalkyl group Chemical group 0.000 claims abstract description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 5
- 229940116211 Vasopressin antagonist Drugs 0.000 claims abstract description 3
- 239000003038 vasopressin antagonist Substances 0.000 claims abstract description 3
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 13
- GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 claims description 11
- 102000002852 Vasopressins Human genes 0.000 claims description 11
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- 229960003726 vasopressin Drugs 0.000 claims description 11
- 208000030761 polycystic kidney disease Diseases 0.000 claims description 10
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- GYHCTFXIZSNGJT-KLTYLHELSA-N n-[4-(7-chloro-2,2-dideuterio-5-hydroxy-4,5-dihydro-3h-1-benzazepine-1-carbonyl)-3-methylphenyl]-2-methylbenzamide Chemical compound [2H]C1([2H])CCC(O)C2=CC(Cl)=CC=C2N1C(=O)C(C(=C1)C)=CC=C1NC(=O)C1=CC=CC=C1C GYHCTFXIZSNGJT-KLTYLHELSA-N 0.000 claims description 9
- 206010019280 Heart failures Diseases 0.000 claims description 8
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- 239000004480 active ingredient Substances 0.000 claims description 8
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- GYHCTFXIZSNGJT-YRQUOOKNSA-N n-[4-(7-chloro-4,4,5-trideuterio-5-hydroxy-2,3-dihydro-1-benzazepine-1-carbonyl)-3-methylphenyl]-2-methylbenzamide Chemical compound C12=CC=C(Cl)C=C2C(O)([2H])C([2H])([2H])CCN1C(=O)C(C(=C1)C)=CC=C1NC(=O)C1=CC=CC=C1C GYHCTFXIZSNGJT-YRQUOOKNSA-N 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- GYHCTFXIZSNGJT-CORJAIEOSA-N n-[4-(7-chloro-5-deuterio-5-hydroxy-3,4-dihydro-2h-1-benzazepine-1-carbonyl)-3-methylphenyl]-2-methylbenzamide Chemical compound C12=CC=C(Cl)C=C2C([2H])(O)CCCN1C(=O)C(C(=C1)C)=CC=C1NC(=O)C1=CC=CC=C1C GYHCTFXIZSNGJT-CORJAIEOSA-N 0.000 claims description 6
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- GYHCTFXIZSNGJT-JDRCYIGSSA-N n-[4-(7-chloro-2,2,4,4,5-pentadeuterio-5-hydroxy-3h-1-benzazepine-1-carbonyl)-3-methylphenyl]-2-methylbenzamide Chemical compound [2H]C1([2H])CC([2H])([2H])C([2H])(O)C2=CC(Cl)=CC=C2N1C(=O)C(C(=C1)C)=CC=C1NC(=O)C1=CC=CC=C1C GYHCTFXIZSNGJT-JDRCYIGSSA-N 0.000 claims description 4
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- 229940124549 vasodilator Drugs 0.000 claims description 3
- 239000003071 vasodilator agent Substances 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 112
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 27
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- 238000000605 extraction Methods 0.000 description 17
- 239000000843 powder Substances 0.000 description 17
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- 239000010410 layer Substances 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 230000002401 inhibitory effect Effects 0.000 description 9
- 239000000825 pharmaceutical preparation Substances 0.000 description 9
- 239000012354 sodium borodeuteride Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 8
- 230000003042 antagnostic effect Effects 0.000 description 8
- GYHCTFXIZSNGJT-UHFFFAOYSA-N tolvaptan Chemical compound CC1=CC=CC=C1C(=O)NC(C=C1C)=CC=C1C(=O)N1C2=CC=C(Cl)C=C2C(O)CCC1 GYHCTFXIZSNGJT-UHFFFAOYSA-N 0.000 description 8
- 229920002472 Starch Polymers 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 101150041968 CDC13 gene Proteins 0.000 description 6
- 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 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000008103 glucose Substances 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 230000002440 hepatic effect Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000005515 coenzyme Substances 0.000 description 4
- 230000008030 elimination Effects 0.000 description 4
- 238000003379 elimination reaction Methods 0.000 description 4
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 4
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- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical class CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 3
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- 244000299461 Theobroma cacao Species 0.000 description 3
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- RHTVHZOYZBIGAT-UHFFFAOYSA-N ethyl 4-(5-chloro-2-nitrophenyl)-4-trimethylsilyloxybutanoate Chemical compound CCOC(=O)CCC(O[Si](C)(C)C)C1=CC(Cl)=CC=C1[N+]([O-])=O RHTVHZOYZBIGAT-UHFFFAOYSA-N 0.000 description 3
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- VENGMROMZOKURN-UHFFFAOYSA-N n-[4-(7-chloro-5-oxo-3,4-dihydro-2h-1-benzazepine-1-carbonyl)-3-methylphenyl]-2-methylbenzamide Chemical compound CC1=CC=CC=C1C(=O)NC(C=C1C)=CC=C1C(=O)N1C2=CC=C(Cl)C=C2C(=O)CCC1 VENGMROMZOKURN-UHFFFAOYSA-N 0.000 description 3
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- NRNCYVBFPDDJNE-UHFFFAOYSA-N pemoline Chemical compound O1C(N)=NC(=O)C1C1=CC=CC=C1 NRNCYVBFPDDJNE-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical class [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 238000002553 single reaction monitoring Methods 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical class [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001331 thermoregulatory effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- 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
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Otolaryngology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Studio Devices (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009-245434 | 2009-10-26 | ||
| JP2009245434 | 2009-10-26 | ||
| PCT/JP2010/068807 WO2011052519A1 (ja) | 2009-10-26 | 2010-10-25 | ベンズアゼピン化合物 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2778756A1 true CA2778756A1 (en) | 2011-05-05 |
Family
ID=43921941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2778756A Abandoned CA2778756A1 (en) | 2009-10-26 | 2010-10-25 | Benzazepine compound |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US8940727B2 (OSRAM) |
| EP (1) | EP2495236A4 (OSRAM) |
| JP (1) | JP5717645B2 (OSRAM) |
| KR (1) | KR20120092139A (OSRAM) |
| CN (3) | CN104829531A (OSRAM) |
| AU (1) | AU2010312651A1 (OSRAM) |
| BR (1) | BR112012009784A2 (OSRAM) |
| CA (1) | CA2778756A1 (OSRAM) |
| CO (1) | CO6481003A2 (OSRAM) |
| EA (1) | EA022253B1 (OSRAM) |
| IL (1) | IL219132A0 (OSRAM) |
| IN (1) | IN2012DN03343A (OSRAM) |
| MX (1) | MX2012004843A (OSRAM) |
| PH (1) | PH12012500762A1 (OSRAM) |
| SG (1) | SG10201406839VA (OSRAM) |
| WO (1) | WO2011052519A1 (OSRAM) |
| ZA (1) | ZA201202640B (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JO3711B1 (ar) | 2015-07-13 | 2021-01-31 | H Lundbeck As | أجسام مضادة محددة لبروتين تاو وطرق استعمالها |
| WO2019003433A1 (ja) * | 2017-06-30 | 2019-01-03 | 大塚製薬株式会社 | ベンゾアゼピン誘導体 |
| HU231206B1 (hu) | 2017-12-15 | 2021-10-28 | Richter Gedeon Nyrt. | Triazolobenzazepinek |
| TW201938171A (zh) | 2017-12-15 | 2019-10-01 | 匈牙利商羅特格登公司 | 作為血管升壓素Ｖ１ａ受體拮抗劑之三環化合物 |
| JP6868089B2 (ja) * | 2018-12-28 | 2021-05-12 | 大塚製薬株式会社 | 医薬 |
| CN112851583B (zh) * | 2021-01-19 | 2023-09-08 | 徐州医科大学 | 新型苯并氮杂䓬类化合物、组合物及其用途 |
| CN121449554B (zh) * | 2026-01-07 | 2026-04-28 | 浙江大学医学院附属邵逸夫医院（浙江省邵逸夫医院） | 一种包含具有2-芳甲酰基苯并氮杂䓬结构的小分子化合物的药物及其应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2905909B2 (ja) * | 1991-04-19 | 1999-06-14 | 大塚製薬株式会社 | バソプレシン拮抗剤 |
| US5258510A (en) * | 1989-10-20 | 1993-11-02 | Otsuka Pharma Co Ltd | Benzoheterocyclic compounds |
| WO1991005549A1 (en) | 1989-10-20 | 1991-05-02 | Otsuka Pharmaceutical Co., Ltd. | Benzoheterocyclic compounds |
| US5753677A (en) * | 1989-10-20 | 1998-05-19 | Otsuka Pharmaceutical Co., Ltd. | Benzoheterocyclic compounds |
| CN1040210C (zh) | 1993-07-21 | 1998-10-14 | 山之内制药株式会社 | 稠合的苯并氮杂䓬衍生物及其药学组合物 |
| CN101273024A (zh) | 2005-07-29 | 2008-09-24 | 康瑟特制药公司 | 新颖苯并[d][1,3]-二氧杂环戊烯衍生物 |
| EP2024365A4 (en) * | 2006-06-05 | 2010-08-25 | Auspex Pharmaceuticals Inc | PREPARATION AND UTILITY OF SUBSTITUTED IMIDAZOPYRIDINE COMPOUNDS HAVING HYPNOTIC EFFECTS |
| BRPI0715579A2 (pt) * | 2006-10-19 | 2015-05-26 | Auspex Pharmaceuticals Inc | "composto, composição farmacêutica e uso de um composto" |
| TWI459947B (zh) * | 2007-06-26 | 2014-11-11 | Otsuka Pharma Co Ltd | 苯并氮呯化合物及藥學製劑 |
| WO2009117144A1 (en) | 2008-03-20 | 2009-09-24 | Concert Pharmaceuticals, Inc. | Benzazepine compounds |
-
2010
- 2010-10-25 WO PCT/JP2010/068807 patent/WO2011052519A1/ja not_active Ceased
- 2010-10-25 CA CA2778756A patent/CA2778756A1/en not_active Abandoned
- 2010-10-25 SG SG10201406839VA patent/SG10201406839VA/en unknown
- 2010-10-25 KR KR1020127013513A patent/KR20120092139A/ko not_active Withdrawn
- 2010-10-25 PH PH1/2012/500762A patent/PH12012500762A1/en unknown
- 2010-10-25 JP JP2011538404A patent/JP5717645B2/ja not_active Expired - Fee Related
- 2010-10-25 AU AU2010312651A patent/AU2010312651A1/en not_active Abandoned
- 2010-10-25 US US13/504,101 patent/US8940727B2/en not_active Expired - Fee Related
- 2010-10-25 EA EA201290228A patent/EA022253B1/ru not_active IP Right Cessation
- 2010-10-25 CN CN201510199726.7A patent/CN104829531A/zh active Pending
- 2010-10-25 EP EP10826651A patent/EP2495236A4/en not_active Withdrawn
- 2010-10-25 CN CN201410616974.2A patent/CN104447555A/zh active Pending
- 2010-10-25 BR BR112012009784A patent/BR112012009784A2/pt not_active IP Right Cessation
- 2010-10-25 IN IN3343DEN2012 patent/IN2012DN03343A/en unknown
- 2010-10-25 CN CN201080048410.3A patent/CN102753530B/zh not_active Expired - Fee Related
- 2010-11-25 MX MX2012004843A patent/MX2012004843A/es unknown
-
2012
- 2012-04-12 ZA ZA2012/02640A patent/ZA201202640B/en unknown
- 2012-04-15 IL IL219132A patent/IL219132A0/en unknown
- 2012-05-24 CO CO12086123A patent/CO6481003A2/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| ZA201202640B (en) | 2013-06-26 |
| EP2495236A1 (en) | 2012-09-05 |
| JP5717645B2 (ja) | 2015-05-13 |
| BR112012009784A2 (pt) | 2016-05-17 |
| CN104447555A (zh) | 2015-03-25 |
| CN102753530B (zh) | 2015-06-17 |
| EA201290228A1 (ru) | 2012-12-28 |
| WO2011052519A1 (ja) | 2011-05-05 |
| MX2012004843A (es) | 2012-05-29 |
| AU2010312651A1 (en) | 2012-05-03 |
| CN102753530A (zh) | 2012-10-24 |
| IN2012DN03343A (OSRAM) | 2015-10-23 |
| PH12012500762A1 (en) | 2012-11-26 |
| EP2495236A4 (en) | 2013-03-27 |
| IL219132A0 (en) | 2012-06-28 |
| CO6481003A2 (es) | 2012-07-16 |
| JPWO2011052519A1 (ja) | 2013-03-21 |
| US8940727B2 (en) | 2015-01-27 |
| EA022253B1 (ru) | 2015-11-30 |
| US20130131045A1 (en) | 2013-05-23 |
| KR20120092139A (ko) | 2012-08-20 |
| SG10201406839VA (en) | 2014-12-30 |
| CN104829531A (zh) | 2015-08-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20161026 |