SK17602002A3 - Benzoxazepinóny, spôsob ich výroby a použitia - Google Patents

Benzoxazepinóny, spôsob ich výroby a použitia Download PDF

Info

Publication number: SK17602002A3
Authority: SK; Slovakia
Prior art keywords: dimethoxyphenyl; chloro; oxo; tetrahydro; dimethylpropyl
Prior art date: 2000-06-23

Application number

SK1760-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Masakuni Kori

Takashi Miki

Tomoyuki Nishimoto

Ryuichi Tozawa

Original Assignee

Takeda Chemical Industries, Ltd.

Priority date (The priority date 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 date listed.)

2000-06-23

Filing date

2001-06-22

Publication date

2003-06-03

2001-06-22 Application filed by Takeda Chemical Industries, Ltd. filed Critical Takeda Chemical Industries, Ltd.

2003-06-03 Publication of SK17602002A3 publication Critical patent/SK17602002A3/sk

Links

HZRJIAKKDMLYFS-UHFFFAOYSA-N 1,2-benzoxazepin-3-one Chemical class C1=CC(=O)NOC2=CC=CC=C21 HZRJIAKKDMLYFS-UHFFFAOYSA-N 0.000 title description 2
239000004059 squalene synthase inhibitor Substances 0.000 title 1
-1 1-carboxyethyl group Chemical group 0.000 claims abstract description 289
150000001875 compounds Chemical class 0.000 claims abstract description 156
150000003839 salts Chemical class 0.000 claims abstract description 137
125000000217 alkyl group Chemical group 0.000 claims abstract description 75
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 47
125000003118 aryl group Chemical group 0.000 claims abstract description 36
208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 24
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 19
125000004423 acyloxy group Chemical group 0.000 claims abstract description 15
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims abstract description 13
125000005352 carboxycycloalkyl group Chemical group 0.000 claims abstract description 9
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 8
125000005843 halogen group Chemical group 0.000 claims abstract description 8
239000000203 mixture Substances 0.000 claims description 226
125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 191
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 155
125000004432 carbon atom Chemical group C* 0.000 claims description 104
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 81
235000019260 propionic acid Nutrition 0.000 claims description 77
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 claims description 77
238000000034 method Methods 0.000 claims description 48
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 41
229940002612 prodrug Drugs 0.000 claims description 32
239000000651 prodrug Substances 0.000 claims description 32
239000003795 chemical substances by application Substances 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
125000004181 carboxyalkyl group Chemical group 0.000 claims description 23
241000124008 Mammalia Species 0.000 claims description 22
125000001424 substituent group Chemical group 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 claims description 20
230000015572 biosynthetic process Effects 0.000 claims description 19
238000002360 preparation method Methods 0.000 claims description 18
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
239000008194 pharmaceutical composition Substances 0.000 claims description 14
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 13
YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 claims description 12
BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 claims description 12
PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims description 12
150000002632 lipids Chemical class 0.000 claims description 12
229940031439 squalene Drugs 0.000 claims description 12
TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 claims description 12
230000002401 inhibitory effect Effects 0.000 claims description 11
238000003786 synthesis reaction Methods 0.000 claims description 11
125000003710 aryl alkyl group Chemical group 0.000 claims description 10
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 10
UAFHRUBCOQPFFM-UHFFFAOYSA-N 1-(aminomethyl)cyclohexane-1-carboxylic acid Chemical compound NCC1(C(O)=O)CCCCC1 UAFHRUBCOQPFFM-UHFFFAOYSA-N 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
108010023302 HDL Cholesterol Proteins 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
239000003112 inhibitor Substances 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 6
239000003524 antilipemic agent Substances 0.000 claims description 6
150000003626 triacylglycerols Chemical class 0.000 claims description 6
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
YOHMGTMHXJTGAC-GRKNLSHJSA-N 3-[3-[[2-[(3r,5s)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-5h-4,1-benzoxazepin-3-yl]acetyl]amino]-4-methylphenyl]propanoic acid Chemical compound COC1=CC=CC([C@@H]2C3=CC(Cl)=CC=C3N(CC(C)(C)CO)C(=O)[C@@H](CC(=O)NC=3C(=CC=C(CCC(O)=O)C=3)C)O2)=C1OC YOHMGTMHXJTGAC-GRKNLSHJSA-N 0.000 claims description 4
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
235000010855 food raising agent Nutrition 0.000 claims description 4
230000001965 increasing effect Effects 0.000 claims description 4
ZSAAUZFZVNMRFM-ISKFKSNPSA-N 2-[(3r,5s)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-5h-4,1-benzoxazepin-3-yl]-n-propylsulfonylacetamide Chemical compound C1([C@H]2O[C@@H](C(N(CC(C)(C)CO)C3=CC=C(Cl)C=C32)=O)CC(=O)NS(=O)(=O)CCC)=CC=CC(OC)=C1OC ZSAAUZFZVNMRFM-ISKFKSNPSA-N 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 2
APTRWBJEYRUNGF-GRKNLSHJSA-N 3-[3-[[[2-[(3r,5s)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-5h-4,1-benzoxazepin-3-yl]acetyl]amino]methyl]phenyl]propanoic acid Chemical compound COC1=CC=CC([C@@H]2C3=CC(Cl)=CC=C3N(CC(C)(C)CO)C(=O)[C@@H](CC(=O)NCC=3C=C(CCC(O)=O)C=CC=3)O2)=C1OC APTRWBJEYRUNGF-GRKNLSHJSA-N 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 12
ILROLYQPRYHHFG-UHFFFAOYSA-N 1-$l^{1}-oxidanylprop-2-en-1-one Chemical group [O]C(=O)C=C ILROLYQPRYHHFG-UHFFFAOYSA-N 0.000 claims 1
MXJJXDNIRHQHKF-QLWXXVCSSA-N 5-[3-[[2-[(3r,5s)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-5h-4,1-benzoxazepin-3-yl]acetyl]amino]-4-fluorophenyl]pentanoic acid Chemical compound COC1=CC=CC([C@@H]2C3=CC(Cl)=CC=C3N(CC(C)(C)CO)C(=O)[C@@H](CC(=O)NC=3C(=CC=C(CCCCC(O)=O)C=3)F)O2)=C1OC MXJJXDNIRHQHKF-QLWXXVCSSA-N 0.000 claims 1
NQZXMSVIVNSXKL-BPAKYRGESA-N ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)CCC(C(=O)O)N)C2=C(C(=CC=C2)OC)OC)C=1 Chemical compound ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)CCC(C(=O)O)N)C2=C(C(=CC=C2)OC)OC)C=1 NQZXMSVIVNSXKL-BPAKYRGESA-N 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract description 31
230000000694 effects Effects 0.000 abstract description 17
235000012000 cholesterol Nutrition 0.000 abstract description 11
125000002947 alkylene group Chemical group 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 542
239000000243 solution Substances 0.000 description 410
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 264
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 215
235000019439 ethyl acetate Nutrition 0.000 description 180
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 170
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 155
229910052739 hydrogen Inorganic materials 0.000 description 155
230000002829 reductive effect Effects 0.000 description 149
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 147
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 147
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 111
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 107
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 104
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 102
238000002329 infrared spectrum Methods 0.000 description 86
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 85
229910052799 carbon Inorganic materials 0.000 description 84
238000005160 1H NMR spectroscopy Methods 0.000 description 83
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 80
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 78
239000000843 powder Substances 0.000 description 78
229910052938 sodium sulfate Inorganic materials 0.000 description 78
235000011152 sodium sulphate Nutrition 0.000 description 78
238000006243 chemical reaction Methods 0.000 description 71
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 69
238000003756 stirring Methods 0.000 description 66
238000010898 silica gel chromatography Methods 0.000 description 63
239000002904 solvent Substances 0.000 description 59
239000003480 eluent Substances 0.000 description 51
229910052757 nitrogen Chemical group 0.000 description 51
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 49
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 38
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 38
239000012044 organic layer Substances 0.000 description 34
239000003814 drug Substances 0.000 description 32
238000001953 recrystallisation Methods 0.000 description 32
229940079593 drug Drugs 0.000 description 30
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 26
235000017557 sodium bicarbonate Nutrition 0.000 description 24
229910000030 sodium bicarbonate Inorganic materials 0.000 description 24
239000000460 chlorine Substances 0.000 description 22
125000004494 ethyl ester group Chemical group 0.000 description 22
239000013078 crystal Substances 0.000 description 21
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 21
239000000706 filtrate Substances 0.000 description 20
150000004702 methyl esters Chemical class 0.000 description 20
239000012346 acetyl chloride Substances 0.000 description 18
230000020477 pH reduction Effects 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 17
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 17
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 16
201000010099 disease Diseases 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 15
238000001816 cooling Methods 0.000 description 14
239000002244 precipitate Substances 0.000 description 14
238000005481 NMR spectroscopy Methods 0.000 description 13
ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 description 13
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
238000001914 filtration Methods 0.000 description 12
239000000284 extract Substances 0.000 description 11
XDYXHEVDYHBTIF-FYYLOGMGSA-N 2-[(3r,5s)-1-(3-acetyloxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-5h-4,1-benzoxazepin-3-yl]acetic acid Chemical compound COC1=CC=CC([C@@H]2C3=CC(Cl)=CC=C3N(CC(C)(C)COC(C)=O)C(=O)[C@@H](CC(O)=O)O2)=C1OC XDYXHEVDYHBTIF-FYYLOGMGSA-N 0.000 description 10
JIGKRELXCKTDLL-TZIWHRDSSA-N 2-[(3r,5s)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-5h-4,1-benzoxazepin-3-yl]acetic acid Chemical compound COC1=CC=CC([C@@H]2C3=CC(Cl)=CC=C3N(CC(C)(C)CO)C(=O)[C@@H](CC(O)=O)O2)=C1OC JIGKRELXCKTDLL-TZIWHRDSSA-N 0.000 description 10
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 10
210000004369 blood Anatomy 0.000 description 10
239000008280 blood Substances 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-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 9
208000007536 Thrombosis Diseases 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 9
239000000725 suspension Substances 0.000 description 9
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
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 8
ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 8
125000003277 amino group Chemical group 0.000 description 8
239000012230 colorless oil Substances 0.000 description 8
206010012601 diabetes mellitus Diseases 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
239000011734 sodium Substances 0.000 description 8
229910000342 sodium bisulfate Inorganic materials 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 7
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
125000006615 aromatic heterocyclic group Chemical group 0.000 description 7
125000004429 atom Chemical group 0.000 description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
239000012043 crude product Substances 0.000 description 7
239000004615 ingredient Substances 0.000 description 7
239000007788 liquid Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
229910052731 fluorine Inorganic materials 0.000 description 6
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
238000002156 mixing Methods 0.000 description 6
239000003921 oil Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
230000002265 prevention Effects 0.000 description 6
239000012279 sodium borohydride Substances 0.000 description 6
229910000033 sodium borohydride Inorganic materials 0.000 description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
239000012359 Methanesulfonyl chloride Substances 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
238000001035 drying Methods 0.000 description 5
229940088598 enzyme Drugs 0.000 description 5
239000011737 fluorine Substances 0.000 description 5
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239000011591 potassium Substances 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
239000001120 potassium sulphate Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
229960005205 prednisolone Drugs 0.000 description 1
APGDTXUMTIZLCJ-CGVGKPPMSA-N prednisolone succinate Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)COC(=O)CCC(O)=O)[C@@H]4[C@@H]3CCC2=C1 APGDTXUMTIZLCJ-CGVGKPPMSA-N 0.000 description 1
229950004597 prednisolone succinate Drugs 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 1
229960003912 probucol Drugs 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 description 1
125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 description 1
229960004622 raloxifene Drugs 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 description 1
238000006456 reductive dimerization reaction Methods 0.000 description 1
239000012744 reinforcing agent Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
208000037803 restenosis Diseases 0.000 description 1
SUFUKZSWUHZXAV-BTJKTKAUSA-N rosiglitazone maleate Chemical compound [H+].[H+].[O-]C(=O)\C=C/C([O-])=O.C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O SUFUKZSWUHZXAV-BTJKTKAUSA-N 0.000 description 1
LALFOYNTGMUKGG-BGRFNVSISA-L rosuvastatin calcium Chemical compound [Ca+2].CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O.CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O LALFOYNTGMUKGG-BGRFNVSISA-L 0.000 description 1
230000007017 scission Effects 0.000 description 1
229960002855 simvastatin Drugs 0.000 description 1
RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 1
235000015500 sitosterol Nutrition 0.000 description 1
229950005143 sitosterol Drugs 0.000 description 1
NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 description 1
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000003432 sterols Chemical class 0.000 description 1
235000003702 sterols Nutrition 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000002889 sympathetic effect Effects 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
229960003454 tamoxifen citrate Drugs 0.000 description 1
FQZYTYWMLGAPFJ-OQKDUQJOSA-N tamoxifen citrate Chemical compound [H+].[H+].[H+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 FQZYTYWMLGAPFJ-OQKDUQJOSA-N 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000012360 testing method Methods 0.000 description 1
VOCBWIIFXDYGNZ-IXKNJLPQSA-N testosterone enanthate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCCCC)[C@@]1(C)CC2 VOCBWIIFXDYGNZ-IXKNJLPQSA-N 0.000 description 1
229960003484 testosterone enanthate Drugs 0.000 description 1
QIQCZROILFZKAT-UHFFFAOYSA-N tetracarbon dioxide Chemical group O=C=C=C=C=O QIQCZROILFZKAT-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
WZDGZWOAQTVYBX-XOINTXKNSA-N tibolone Chemical compound C([C@@H]12)C[C@]3(C)[C@@](C#C)(O)CC[C@H]3[C@@H]1[C@H](C)CC1=C2CCC(=O)C1 WZDGZWOAQTVYBX-XOINTXKNSA-N 0.000 description 1
229960001023 tibolone Drugs 0.000 description 1
MTKNGOHFNXIVOS-UHFFFAOYSA-N ticlopidine hydrochloride Chemical compound [H+].[Cl-].ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 MTKNGOHFNXIVOS-UHFFFAOYSA-N 0.000 description 1
229960000984 tocofersolan Drugs 0.000 description 1
238000011200 topical administration Methods 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
229910052723 transition metal Inorganic materials 0.000 description 1
229940108519 trasylol Drugs 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
UZOHFHFMSPULPR-UHFFFAOYSA-L trimethyl-[2-(1,1,6-trimethylpiperidin-1-ium-2-carbonyl)oxyethyl]azanium;diiodide Chemical compound [I-].[I-].CC1CCCC(C(=O)OCC[N+](C)(C)C)[N+]1(C)C UZOHFHFMSPULPR-UHFFFAOYSA-L 0.000 description 1
229940035936 ubiquinone Drugs 0.000 description 1
229960005356 urokinase Drugs 0.000 description 1
210000003556 vascular endothelial cell Anatomy 0.000 description 1
235000019166 vitamin D Nutrition 0.000 description 1
239000011710 vitamin D Substances 0.000 description 1
150000003710 vitamin D derivatives Chemical class 0.000 description 1
229940046008 vitamin d Drugs 0.000 description 1
229960001729 voglibose Drugs 0.000 description 1
230000008673 vomiting Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229940072252 zestril Drugs 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
239000002076 α-tocopherol Substances 0.000 description 1
235000004835 α-tocopherol Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- A61P3/06—Antihyperlipidemics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/14—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Enzymes And Modification Thereof (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SK1760-2002A 2000-06-23 2001-06-22 Benzoxazepinóny, spôsob ich výroby a použitia SK17602002A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP2000190253		2000-06-23
PCT/JP2001/005347 WO2001098282A1 (en)	2000-06-23	2001-06-22	Benzoxazepinones and their use as squalene synthase inhibitors

Publications (1)

Publication Number	Publication Date
SK17602002A3 true SK17602002A3 (sk)	2003-06-03

Family

ID=18689751

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1760-2002A SK17602002A3 (sk)	2000-06-23	2001-06-22	Benzoxazepinóny, spôsob ich výroby a použitia

Country Status (16)

Country	Link
US (1)	US20030078251A1 (pl)
EP (1)	EP1292585A1 (pl)
KR (1)	KR20030011362A (pl)
CN (1)	CN1437587A (pl)
AR (1)	AR028974A1 (pl)
AU (1)	AU2001274588A1 (pl)
BR (1)	BR0111835A (pl)
CA (1)	CA2413429A1 (pl)
CZ (1)	CZ20024151A3 (pl)
HU (1)	HUP0301301A2 (pl)
MX (1)	MXPA02012481A (pl)
NO (1)	NO20026164D0 (pl)
PL (1)	PL360243A1 (pl)
SK (1)	SK17602002A3 (pl)
WO (1)	WO2001098282A1 (pl)
ZA (1)	ZA200209055B (pl)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1473053A (zh) *	2000-11-09	2004-02-04	��ҩƷ��ҵ��ʽ��	高密度脂蛋白-胆甾醇含量提高剂
JP2004525109A (ja)	2001-02-15	2004-08-19	キング・ファーマシューティカルズ・インコーポレイティッド	安定化された甲状腺ホルモン医薬組成物、及びその製法
EP1407782A4 (en) *	2001-06-28	2004-10-20	Takeda Chemical Industries Ltd	AGENTS FOR PREVENTION / TREATMENT OF FUNCTIONAL ORGANIC DISEASES AND ORGANIC DYSFUNCTION
US7101569B2 (en)	2001-08-14	2006-09-05	Franz G Andrew	Methods of administering levothyroxine pharmaceutical compositions
CA2513170A1 (en) *	2003-01-17	2004-08-05	Takeda Pharmaceutical Company Limited	Skeletal muscle protecting agent
WO2004091628A1 (ja) *	2003-04-18	2004-10-28	Takeda Pharmaceutical Company Limited	受容体拮抗剤
US7060698B2 (en)	2003-05-19	2006-06-13	Hoffmann-La Roche Inc.	Benzoxazepinone derivatives
DE102004006325A1 (de) *	2004-02-10	2005-08-25	Bayer Healthcare Ag	Tetrahydrobenzo[d]azepin-2-on-Derivate und ihre Verwendung
WO2006016681A2 (en) *	2004-08-09	2006-02-16	Takeda Pharmaceutical Company Limited	Crp lowering agent
TW200714280A (en) *	2005-06-01	2007-04-16	Takeda Pharmaceuticals Co	Novel method of treating hyperlipidemia
CN102164900B (zh)	2008-09-25	2014-04-16	霍夫曼-拉罗奇有限公司	3-氨基-吲唑或3-氨基-4,5,6,7-四氢-吲唑衍生物
JP6050238B2 (ja)	2011-10-19	2016-12-21	興和株式会社	新規なスピロインドリン化合物、及びそれを含有する医薬
CN112274500A (zh) *	2020-10-30	2021-01-29	河南省儿童医院郑州儿童医院	单孢菌酸在制备抗凝血药物中的应用

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE69332792T2 (de) *	1992-04-20	2004-01-15	Takeda Chemical Industries Ltd	4,1-Benzoxazepinderivate als Squalen-Synthetase Inhibitoren und ihre Verwendung zur Behandlung von Hypercholesterämie und als Fungizide
CN1072649C (zh) *	1995-09-13	2001-10-10	武田药品工业株式会社	苯并氧杂吖庚因化合物,其生产方法和用途

2001
- 2001-06-22 HU HU0301301A patent/HUP0301301A2/hu unknown
- 2001-06-22 SK SK1760-2002A patent/SK17602002A3/sk unknown
- 2001-06-22 MX MXPA02012481A patent/MXPA02012481A/es unknown
- 2001-06-22 WO PCT/JP2001/005347 patent/WO2001098282A1/en not_active Ceased
- 2001-06-22 KR KR1020027017487A patent/KR20030011362A/ko not_active Withdrawn
- 2001-06-22 AR ARP010102994A patent/AR028974A1/es unknown
- 2001-06-22 EP EP01941174A patent/EP1292585A1/en not_active Withdrawn
- 2001-06-22 PL PL36024301A patent/PL360243A1/pl not_active Application Discontinuation
- 2001-06-22 BR BR0111835-8A patent/BR0111835A/pt not_active Application Discontinuation
- 2001-06-22 AU AU2001274588A patent/AU2001274588A1/en not_active Abandoned
- 2001-06-22 CN CN01811567A patent/CN1437587A/zh active Pending
- 2001-06-22 US US10/203,524 patent/US20030078251A1/en not_active Abandoned
- 2001-06-22 CA CA002413429A patent/CA2413429A1/en not_active Abandoned
- 2001-06-22 CZ CZ20024151A patent/CZ20024151A3/cs unknown
2002
- 2002-11-07 ZA ZA200209055A patent/ZA200209055B/en unknown
- 2002-12-20 NO NO20026164A patent/NO20026164D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
EP1292585A1 (en)	2003-03-19
AR028974A1 (es)	2003-05-28
KR20030011362A (ko)	2003-02-07
HUP0301301A2 (hu)	2003-08-28
PL360243A1 (pl)	2004-09-06
BR0111835A (pt)	2003-04-29
CA2413429A1 (en)	2001-12-27
AU2001274588A1 (en)	2002-01-02
CZ20024151A3 (cs)	2003-05-14
CN1437587A (zh)	2003-08-20
NO20026164L (no)	2002-12-20
NO20026164D0 (no)	2002-12-20
ZA200209055B (en)	2003-11-07
US20030078251A1 (en)	2003-04-24
MXPA02012481A (es)	2003-06-06
WO2001098282A1 (en)	2001-12-27

Publication	Publication Date	Title
EP0862562B1 (en)	2001-07-04	Benzoxazepine compounds, their production and use as lipid lowering agents
US20030153507A1 (en)	2003-08-14	HIV protease inhibitors, compositions containing the same, their pharmaceutical uses and materials for their synthesis
RU2268882C1 (ru)	2006-01-27	Производное 4,4-дифтор-1,2,3,4-тетрагидро-5н-бензазепина, его соль и содержащая его фармацевтическая композиция
EP1097928B1 (en)	2008-07-16	5-(2,3-Dialkoxyphenyl)-4,1-benzoxazepin-2-ones as anti-hyperlipidemics
NL8502310A (nl)	1986-03-17	Analgetisch werkzame 1,2-benzisothiazol-3-ylpiperazine derivaten.
CZ292942B6 (cs)	2004-01-14	Derivát (N-hydroxykarbamoyl)-1-(4-fenoxy)benzensulfonylu
CA2536313A1 (en)	2005-03-03	Fused pyrimidine derivative and use thereof
US20030078251A1 (en)	2003-04-24	Benzoxazepinones and their use as squalene synthase inhibitors
DE69832376T2 (de)	2006-08-03	4,1-benzoxazepine, ihre analoga, und ihre verwendung als somatostatin-agonisten
EP1407782A1 (en)	2004-04-14	Preventives/remedies for organ functional disorders and organ dysfunction
WO2000023437A1 (en)	2000-04-27	Nitrogenous fused heterocycle compounds, process for the preparation thereof and agents containing the same
RU2337100C2 (ru)	2008-10-27	Производные бензоксазепина, способ их получения, лекарственное средство на их основе и их применение
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KR20030048465A (ko)	2003-06-19	고밀도 지질단백질-콜레스테롤 상승제
JP2005097276A (ja)	2005-04-14	縮合ピリミジン誘導体およびその用途
JP2002080468A (ja)	2002-03-19	ベンゾオキサゼピン化合物
JP2003081873A (ja)	2003-03-19	臓器機能障害および臓器不全の予防治療剤
JP2003064063A (ja)	2003-03-05	ベンゾオキサゼピン化合物
JP4138299B2 (ja)	2008-08-27	高密度リポタンパク−コレステロール上昇剤
JP4021612B2 (ja)	2007-12-12	ベンゾオキサゼピン化合物
JP3283628B2 (ja)	2002-05-20	４，１−ベンゾオキサゼピン誘導体とその用途
HK1089757A (en)	2006-12-08	Benzoxazepine compound
JP2005068138A (ja)	2005-03-17	ベンズオキサゼピン系化合物
JP2007332154A (ja)	2007-12-27	ベンゾオキサゼピン化合物
JPH02188575A (ja)	1990-07-24	１，５―ベンゾチアゼピン―３―カルボン酸化合物