JP2000506160A - 神経学的に活性な試剤としてのアゾロベンズアゼピン誘導体 - Google Patents

神経学的に活性な試剤としてのアゾロベンズアゼピン誘導体

Info

Publication number: JP2000506160A
Authority: JP; Japan
Prior art keywords: lower alkyl; phenyl; group; chloro; compound
Prior art date: 1996-03-08
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.): Ceased

Application number

JP9531562A

Other languages

English (en)

Japanese (ja)

Other versions

JP2000506160A5 (2

Inventor

アンブラッシュ，ケリー

ジェロームチャプデレーン，マーク

ジャクソンフレジー，ウィリアム

エニッドガルシア―ダヴェンポート，ローラ

ジェイムズレウィス，ジョセフ

Original Assignee

ゼネカリミテッド

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.)

1996-03-08

Filing date

1997-03-04

Publication date

2000-05-23

1997-03-04 Application filed by ゼネカリミテッド filed Critical ゼネカリミテッド

2000-05-23 Publication of JP2000506160A publication Critical patent/JP2000506160A/ja

2004-11-25 Publication of JP2000506160A5 publication Critical patent/JP2000506160A5/ja

Status Ceased legal-status Critical Current

Links

239000013543 active substance Substances 0.000 title description 2
239000001257 hydrogen Substances 0.000 claims abstract description 63
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 63
238000000034 method Methods 0.000 claims abstract description 55
150000002431 hydrogen Chemical class 0.000 claims abstract description 37
229910052799 carbon Inorganic materials 0.000 claims abstract description 28
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 23
229910052760 oxygen Inorganic materials 0.000 claims abstract description 23
229910052736 halogen Inorganic materials 0.000 claims abstract description 20
150000002367 halogens Chemical class 0.000 claims abstract description 20
208000012902 Nervous system disease Diseases 0.000 claims abstract description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 243
125000000217 alkyl group Chemical group 0.000 claims description 212
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 139
-1 ha Logen Chemical group 0.000 claims description 124
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 87
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 68
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 46
150000003839 salts Chemical class 0.000 claims description 46
125000003545 alkoxy group Chemical group 0.000 claims description 34
125000000304 alkynyl group Chemical group 0.000 claims description 30
125000003282 alkyl amino group Chemical group 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 26
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 23
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 22
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 21
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 20
125000000753 cycloalkyl group Chemical group 0.000 claims description 19
125000002757 morpholinyl group Chemical group 0.000 claims description 15
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
125000004414 alkyl thio group Chemical group 0.000 claims description 12
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 11
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 10
BYGJDSSWGMQHFV-UHFFFAOYSA-N ethyl 7-chloro-4,10-dioxo-2,5-dihydropyrazolo[3,4-c][1]benzazepine-1-carboxylate Chemical compound O=C1C2=CC=C(Cl)C=C2NC(=O)C2=C1C(C(=O)OCC)=NN2 BYGJDSSWGMQHFV-UHFFFAOYSA-N 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 9
230000002378 acidificating effect Effects 0.000 claims description 7
239000002671 adjuvant Substances 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
239000003981 vehicle Substances 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
125000004193 piperazinyl group Chemical group 0.000 claims description 6
125000003386 piperidinyl group Chemical group 0.000 claims description 6
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
230000008569 process Effects 0.000 claims description 5
125000006030 1-methyl-3-butenyl group Chemical group 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims description 4
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 claims description 4
125000006032 3-methyl-3-butenyl group Chemical group 0.000 claims description 4
DPNCXWXBCBWRNJ-UHFFFAOYSA-N 7-chloro-1-(trifluoromethyl)-2,5-dihydropyrazolo[3,4-c][1]benzazepine-4,10-dione Chemical compound O=C1C2=CC=C(Cl)C=C2NC(=O)C2=C1C(C(F)(F)F)=NN2 DPNCXWXBCBWRNJ-UHFFFAOYSA-N 0.000 claims description 4
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
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 4
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
WXKSZEDCFWOBRB-UHFFFAOYSA-N 7-chloro-4,10-dioxo-3,5-dihydropyrazolo[3,4-c][1]benzazepine-1-carbonitrile Chemical compound C=1C(Cl)=CC=C(C2=O)C=1NC(=O)C1=C2C(C#N)=NN1 WXKSZEDCFWOBRB-UHFFFAOYSA-N 0.000 claims description 3
150000003863 ammonium salts Chemical class 0.000 claims description 3
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 3
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 claims description 3
125000004373 methylthiopropyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000004344 phenylpropyl group Chemical group 0.000 claims description 3
UJPWYEVSNNUVEO-UHFFFAOYSA-N propan-2-yl 7-chloro-4,10-dioxo-2,5-dihydropyrazolo[3,4-c][1]benzazepine-1-carboxylate Chemical compound O=C1C2=CC=C(Cl)C=C2NC(=O)C2=C1C(C(=O)OC(C)C)=NN2 UJPWYEVSNNUVEO-UHFFFAOYSA-N 0.000 claims description 3
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 2
BBEUEVBKSSNESA-UHFFFAOYSA-N butyl 7-chloro-4,10-dioxo-2,5-dihydropyrazolo[3,4-c][1]benzazepine-1-carboxylate Chemical compound O=C1C2=CC=C(Cl)C=C2NC(=O)C2=C1C(C(=O)OCCCC)=NN2 BBEUEVBKSSNESA-UHFFFAOYSA-N 0.000 claims description 2
ACJICPWKQJITJS-UHFFFAOYSA-N methyl 7-chloro-4,10-dioxo-2,5-dihydropyrazolo[3,4-c][1]benzazepine-1-carboxylate Chemical compound O=C1C2=CC=C(Cl)C=C2NC(=O)C2=C1C(C(=O)OC)=NN2 ACJICPWKQJITJS-UHFFFAOYSA-N 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
239000006187 pill Substances 0.000 claims description 2
XSXVTKBWHWTWDZ-UHFFFAOYSA-N propyl 7-chloro-4,10-dioxo-2,5-dihydropyrazolo[3,4-c][1]benzazepine-1-carboxylate Chemical compound O=C1C2=CC=C(Cl)C=C2NC(=O)C2=C1C(C(=O)OCCC)=NN2 XSXVTKBWHWTWDZ-UHFFFAOYSA-N 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 16
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 2
125000001425 triazolyl group Chemical group 0.000 claims 2
125000000623 heterocyclic group Chemical group 0.000 claims 1
208000025966 Neurological disease Diseases 0.000 abstract description 4
150000001721 carbon Chemical group 0.000 abstract 1
125000005010 perfluoroalkyl group Chemical group 0.000 abstract 1
PLKKXWBJOVTVEU-UHFFFAOYSA-N pyrrolo[2,3-i][1]benzazepine Chemical class C1=CC=NC2=C3C=CN=C3C=CC2=C1 PLKKXWBJOVTVEU-UHFFFAOYSA-N 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 147
239000000243 solution Substances 0.000 description 126
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 108
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 99
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
239000007787 solid Substances 0.000 description 77
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 61
239000000203 mixture Substances 0.000 description 61
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
239000011541 reaction mixture Substances 0.000 description 47
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 42
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
238000007792 addition Methods 0.000 description 30
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
239000002904 solvent Substances 0.000 description 28
238000003818 flash chromatography Methods 0.000 description 24
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
239000010410 layer Substances 0.000 description 22
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
239000000706 filtrate Substances 0.000 description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 description 21
239000012044 organic layer Substances 0.000 description 21
239000000843 powder Substances 0.000 description 21
239000000047 product Substances 0.000 description 21
238000003756 stirring Methods 0.000 description 20
239000002198 insoluble material Substances 0.000 description 18
125000003226 pyrazolyl group Chemical group 0.000 description 18
239000003960 organic solvent Substances 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 16
239000002585 base Substances 0.000 description 16
238000010992 reflux Methods 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
238000001914 filtration Methods 0.000 description 14
238000004587 chromatography analysis Methods 0.000 description 13
239000003921 oil Substances 0.000 description 13
235000019198 oils Nutrition 0.000 description 13
238000012360 testing method Methods 0.000 description 13
238000009835 boiling Methods 0.000 description 12
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 11
229960000583 acetic acid Drugs 0.000 description 11
239000012043 crude product Substances 0.000 description 11
238000000746 purification Methods 0.000 description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000012141 concentrate Substances 0.000 description 9
239000003814 drug Substances 0.000 description 9
239000000284 extract Substances 0.000 description 9
239000012065 filter cake Substances 0.000 description 9
239000000463 material Substances 0.000 description 9
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
239000000126 substance Substances 0.000 description 9
239000000725 suspension Substances 0.000 description 9
YWUIUNGMQOICND-UHFFFAOYSA-N (2z)-2-diazo-1,1,1-trifluoroethane Chemical compound FC(F)(F)C=[N+]=[N-] YWUIUNGMQOICND-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
229940079593 drug Drugs 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
150000003852 triazoles Chemical group 0.000 description 8
239000004471 Glycine Substances 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
230000006378 damage Effects 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000002002 slurry Substances 0.000 description 7
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 7
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
QDWJUBJKEHXSMT-UHFFFAOYSA-N boranylidynenickel Chemical compound [Ni]#B QDWJUBJKEHXSMT-UHFFFAOYSA-N 0.000 description 6
210000004556 brain Anatomy 0.000 description 6
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
239000012458 free base Substances 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
239000007788 liquid Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
239000011734 sodium Substances 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
230000000302 ischemic effect Effects 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
239000005695 Ammonium acetate Substances 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
206010061216 Infarction Diseases 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
235000019257 ammonium acetate Nutrition 0.000 description 4
229940043376 ammonium acetate Drugs 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000010828 elution Methods 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
150000002430 hydrocarbons Chemical group 0.000 description 4
230000007574 infarction Effects 0.000 description 4
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
238000000159 protein binding assay Methods 0.000 description 4
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 4
210000000463 red nucleus Anatomy 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000007858 starting material Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
MZPNQUMLOFWSEK-UHFFFAOYSA-N 4-chloro-2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1C=O MZPNQUMLOFWSEK-UHFFFAOYSA-N 0.000 description 3
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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208000015122 neurodegenerative disease Diseases 0.000 description 1
230000000926 neurological effect Effects 0.000 description 1
210000002569 neuron Anatomy 0.000 description 1
239000002581 neurotoxin Substances 0.000 description 1
231100000618 neurotoxin Toxicity 0.000 description 1
229940078494 nickel acetate Drugs 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000009871 nonspecific binding Effects 0.000 description 1
239000004006 olive oil Substances 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
150000002895 organic esters Chemical class 0.000 description 1
239000005416 organic matter Substances 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
238000012856 packing Methods 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
208000033300 perinatal asphyxia Diseases 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000001508 potassium citrate Substances 0.000 description 1
229960002635 potassium citrate Drugs 0.000 description 1
QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
235000011082 potassium citrates Nutrition 0.000 description 1
OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
NPRDHMWYZHSAHR-UHFFFAOYSA-N pyridine;trioxochromium Chemical compound O=[Cr](=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 NPRDHMWYZHSAHR-UHFFFAOYSA-N 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
230000035484 reaction time Effects 0.000 description 1
238000012827 research and development Methods 0.000 description 1
230000004043 responsiveness Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
102220240796 rs553605556 Human genes 0.000 description 1
235000003441 saturated fatty acids Nutrition 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
210000000278 spinal cord Anatomy 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010186 staining Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
210000003568 synaptosome Anatomy 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
MNIMQYYYRRRZHR-BQYQJAHWSA-N tert-butyl (e)-3-(8-chloro-3-methoxy-2,5-dioxo-1h-1-benzazepin-4-yl)prop-2-enoate Chemical compound N1C(=O)C(OC)=C(\C=C\C(=O)OC(C)(C)C)C(=O)C2=CC=C(Cl)C=C21 MNIMQYYYRRRZHR-BQYQJAHWSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000012974 tin catalyst Substances 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
- 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
- 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
- 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
- A61P9/10—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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Psychiatry (AREA)
Addiction (AREA)
Epidemiology (AREA)
Diabetes (AREA)
Obesity (AREA)
Cardiology (AREA)
Psychology (AREA)
Heart & Thoracic Surgery (AREA)
Hematology (AREA)
Emergency Medicine (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Endocrinology (AREA)
Hospice & Palliative Care (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

JP9531562A 1996-03-08 1997-03-04 神経学的に活性な試剤としてのアゾロベンズアゼピン誘導体 Ceased JP2000506160A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US1352896P	1996-03-08	1996-03-08
US60/013,528		1996-03-08
PCT/GB1997/000592 WO1997032883A1 (en)	1996-03-08	1997-03-04	Azolobenzazepine derivatives as neurologically active agents

Publications (2)

Publication Number	Publication Date
JP2000506160A true JP2000506160A (ja)	2000-05-23
JP2000506160A5 JP2000506160A5 (2)	2004-11-25

Family

ID=21760422

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP9531562A Ceased JP2000506160A (ja)	1996-03-08	1997-03-04	神経学的に活性な試剤としてのアゾロベンズアゼピン誘導体

Country Status (13)

Country	Link
US (2)	US6124281A (2)
EP (1)	EP0888350A1 (2)
JP (1)	JP2000506160A (2)
KR (1)	KR19990087585A (2)
CN (1)	CN1084747C (2)
AU (1)	AU723860B2 (2)
CA (1)	CA2247453A1 (2)
IL (1)	IL126095A0 (2)
NO (1)	NO984106L (2)
NZ (1)	NZ330973A (2)
TW (1)	TW486480B (2)
WO (1)	WO1997032883A1 (2)
ZA (1)	ZA971964B (2)

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DE60229298D1 (de) *	2001-12-26	2008-11-20	Meiji Seika Kaisha	Neues kristallines tricyclisches triazolobenzazepinderivat
BR0307504A (pt) *	2002-02-07	2004-12-07	Neurogen Corp	Composto ou sal farmaceuticamente aceitável, composição farmacêutica, métodos tratar doenças, para potencializar um efeito terapêutico de um agente para o snc, para melhorar a memória de curto prazo em um paciente, para determinar a presença ou ausência de receptores gabaa em uma amostra, e para alterar a atividade transdutora de sinal do receptor gabaa, embalagem, e, uso de um composto ou sal
US7731947B2 (en)	2003-11-17	2010-06-08	Intarcia Therapeutics, Inc.	Composition and dosage form comprising an interferon particle formulation and suspending vehicle
ES2540987T3 (es)	2004-05-14	2015-07-15	Millennium Pharmaceuticals, Inc.	Métodos para preparar inhibidores de la aurora cinasa
WO2006083761A2 (en)	2005-02-03	2006-08-10	Alza Corporation	Solvent/polymer solutions as suspension vehicles
US11246913B2 (en)	2005-02-03	2022-02-15	Intarcia Therapeutics, Inc.	Suspension formulation comprising an insulinotropic peptide
MX2008014870A (es)	2006-05-30	2009-02-12	Intarcia Therapeutics Inc	Modulador de flujo para sistema de suministro osmotico con canal interno de dos piezas.
EP2049081B1 (en)	2006-08-09	2012-11-14	Intarcia Therapeutics, Inc.	Osmotic delivery systems and piston assemblies
CL2007003244A1 (es) *	2006-11-16	2008-04-04	Millennium Pharm Inc	Compuestos derivados de pirimido[5,4-d][2]benzazepina; composicion farmaceutica que comprende a dicho compuesto; y uso del compuesto para el tratamiento del cancer.
HRP20130259T1 (hr)	2007-04-23	2013-04-30	Intarcia Therapeutics, Inc.	Suspenzijske formulacije inzulinotropnih peptida i njihove uporabe
DK2240155T3 (da)	2008-02-13	2012-09-17	Intarcia Therapeutics Inc	Indretninger, formuleringer og fremgangsmåder til levering af flere gavnlige midler
RU2535032C2 (ru)	2008-12-22	2014-12-10	Милленниум Фармасьютикалз, Инк.	Сочетание ингибиторов аврора киназы и анти-cd 20 антител
JO3635B1 (ar)	2009-05-18	2020-08-27	Millennium Pharm Inc	مركبات صيدلانية صلبة وطرق لانتاجها
SMT201700583T1 (it)	2009-09-28	2018-01-11	Intarcia Therapeutics Inc	Instaurazione e/o terminazione rapida di erogazione di farmaci in modo sostanzialmente stazionario
CA2788774A1 (en)	2010-02-19	2011-08-25	Millennium Pharmaceuticals, Inc.	Crystalline forms of sodium 4-{[9-chloro-7-(2-fluoro-6-methoxyphenyl)-5h-pyrimido[5,4-d][2]benzazepin-2-yl]amino}-2-methoxybenzoate
US20120208755A1 (en)	2011-02-16	2012-08-16	Intarcia Therapeutics, Inc.	Compositions, Devices and Methods of Use Thereof for the Treatment of Cancers
US20130303519A1 (en)	2012-03-20	2013-11-14	Millennium Pharmaceuticals, Inc.	Methods of treating cancer using aurora kinase inhibitors
WO2014153509A1 (en)	2013-03-22	2014-09-25	Millennium Pharmaceuticals, Inc.	Combination of catalytic mtorc 1/2 inhibitors and selective inhibitors of aurora a kinase
US9889085B1 (en)	2014-09-30	2018-02-13	Intarcia Therapeutics, Inc.	Therapeutic methods for the treatment of diabetes and related conditions for patients with high baseline HbA1c
US10925639B2 (en)	2015-06-03	2021-02-23	Intarcia Therapeutics, Inc.	Implant placement and removal systems
JP2018524292A (ja)	2015-07-21	2018-08-30	ミレニアムファーマシューティカルズ，インコーポレイテッドＭｉｌｌｅｎｎｉｕｍＰｈａｒｍａｃｅｕｔｉｃａｌｓ，Ｉｎｃ．	オーロラキナーゼインヒビターと化学療法剤の投与
RU2760007C2 (ru)	2016-05-16	2021-11-22	Интарсия Терапьютикс, Инк.	Полипептиды, селективные к рецепторам глюкагона, и способы их применения
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USD840030S1 (en)	2016-06-02	2019-02-05	Intarcia Therapeutics, Inc.	Implant placement guide
CN110225762A (zh)	2017-01-03	2019-09-10	因塔西亚制药公司	包括glp-1受体激动剂的连续施用和药物的共同施用的方法

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1997
- 1997-03-04 KR KR1019980707026A patent/KR19990087585A/ko not_active Withdrawn
- 1997-03-04 WO PCT/GB1997/000592 patent/WO1997032883A1/en not_active Ceased
- 1997-03-04 CN CN97192864A patent/CN1084747C/zh not_active Expired - Fee Related
- 1997-03-04 AU AU22253/97A patent/AU723860B2/en not_active Ceased
- 1997-03-04 JP JP9531562A patent/JP2000506160A/ja not_active Ceased
- 1997-03-04 NZ NZ330973A patent/NZ330973A/xx unknown
- 1997-03-04 EP EP97905327A patent/EP0888350A1/en not_active Withdrawn
- 1997-03-04 US US09/142,221 patent/US6124281A/en not_active Expired - Fee Related
- 1997-03-04 CA CA002247453A patent/CA2247453A1/en not_active Abandoned
- 1997-03-04 TW TW086102601A patent/TW486480B/zh active
- 1997-03-04 IL IL12609597A patent/IL126095A0/xx unknown
- 1997-03-06 ZA ZA9701964A patent/ZA971964B/xx unknown
1998
- 1998-09-07 NO NO984106A patent/NO984106L/no not_active Application Discontinuation
2000
- 2000-09-22 US US09/668,261 patent/US6313290B1/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
KR19990087585A (ko)	1999-12-27
IL126095A0 (en)	1999-05-09
US6124281A (en)	2000-09-26
US6313290B1 (en)	2001-11-06
CN1224424A (zh)	1999-07-28
TW486480B (en)	2002-05-11
NO984106D0 (no)	1998-09-07
EP0888350A1 (en)	1999-01-07
WO1997032883A1 (en)	1997-09-12
AU723860B2 (en)	2000-09-07
CA2247453A1 (en)	1997-09-12
ZA971964B (en)	1997-09-08
NZ330973A (en)	2000-03-27
CN1084747C (zh)	2002-05-15
AU2225397A (en)	1997-09-22
NO984106L (no)	1998-11-06

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JP2000506160A (ja)	2000-05-23	神経学的に活性な試剤としてのアゾロベンズアゼピン誘導体
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