ZA200406032B - Dihydrobenzodiazepin-2-one derivatives for the treatment of neurological disorders. - Google Patents

Dihydrobenzodiazepin-2-one derivatives for the treatment of neurological disorders. Download PDF

Info

Publication number: ZA200406032B
Authority: ZA; South Africa
Prior art keywords: phenyl; diazepin; benzo; dihydro; pyridin
Prior art date: 2002-02-06

Application number

ZA200406032A

Other languages

English (en)

Inventor

Geo Adam

Juergen Wichmann

Erwin Goetshi

Thomas Johannes Woltering

Original Assignee

Hoffmann La Roche

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.)

2002-02-06

Filing date

2004-07-28

Publication date

2005-10-12

2004-07-28 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2005-10-12 Publication of ZA200406032B publication Critical patent/ZA200406032B/en

Links

208000012902 Nervous system disease Diseases 0.000 title claims description 5
208000025966 Neurological disease Diseases 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 117
125000000217 alkyl group Chemical group 0.000 claims description 76
125000003545 alkoxy group Chemical group 0.000 claims description 51
-1 -NR’R” Chemical group 0.000 claims description 43
125000003282 alkyl amino group Chemical group 0.000 claims description 31
229910052736 halogen Inorganic materials 0.000 claims description 30
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
239000001257 hydrogen Substances 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 26
238000000034 method Methods 0.000 claims description 25
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
150000002367 halogens Chemical group 0.000 claims description 20
125000001424 substituent group Chemical group 0.000 claims description 19
125000001153 fluoro group Chemical group F* 0.000 claims description 18
AZIZBYRGIGKTLW-UHFFFAOYSA-N 1,4-diazepin-2-one Chemical compound O=C1C=NC=CC=N1 AZIZBYRGIGKTLW-UHFFFAOYSA-N 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 12
125000004414 alkyl thio group Chemical group 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 11
QDKZHQGXPVFLHU-UHFFFAOYSA-N 1,5-benzodiazepin-2-one Chemical compound O=C1C=CN=C2C=CC=CC2=N1 QDKZHQGXPVFLHU-UHFFFAOYSA-N 0.000 claims description 10
125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 10
239000003814 drug Substances 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000004076 pyridyl group Chemical group 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 7
230000002265 prevention Effects 0.000 claims description 7
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 5
230000001684 chronic effect Effects 0.000 claims description 5
238000007363 ring formation reaction Methods 0.000 claims description 5
208000024827 Alzheimer disease Diseases 0.000 claims description 4
208000026139 Memory disease Diseases 0.000 claims description 4
208000028017 Psychotic disease Diseases 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
230000001154 acute effect Effects 0.000 claims description 4
125000005605 benzo group Chemical group 0.000 claims description 4
208000010877 cognitive disease Diseases 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
201000000980 schizophrenia Diseases 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
XTQHVAXLUHGINO-UHFFFAOYSA-N 4-(3-pyridin-3-ylphenyl)-7-(2,2,2-trifluoroethoxy)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound N=1C2=CC(OCC(F)(F)F)=CC=C2NC(=O)CC=1C(C=1)=CC=CC=1C1=CC=CN=C1 XTQHVAXLUHGINO-UHFFFAOYSA-N 0.000 claims description 2
XFCBAUSXXGLTIP-UHFFFAOYSA-N 4-(3-pyridin-3-ylphenyl)-7-(2,2,2-trifluoroethoxy)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OCC(F)(F)F)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 XFCBAUSXXGLTIP-UHFFFAOYSA-N 0.000 claims description 2
JYTRCRINABXASK-UHFFFAOYSA-N 4-(3-pyridin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC2=CC(C(F)(F)F)=CC=C2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 JYTRCRINABXASK-UHFFFAOYSA-N 0.000 claims description 2
GGCAJGPNBPIIQA-UHFFFAOYSA-N 4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-7-ethoxy-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OCC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC(C)=NC(C)=C1 GGCAJGPNBPIIQA-UHFFFAOYSA-N 0.000 claims description 2
PQWNWLVSPGJPAF-UHFFFAOYSA-N 4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=CC=C3N=2)C(F)(F)F)=C1 PQWNWLVSPGJPAF-UHFFFAOYSA-N 0.000 claims description 2
CHTAULFZQPVWNJ-UHFFFAOYSA-N 4-[3-(2-ethylpyridin-4-yl)phenyl]-7-methyl-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(CC)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(C)C=C3N=2)C(F)(F)F)=C1 CHTAULFZQPVWNJ-UHFFFAOYSA-N 0.000 claims description 2
XRLZWRIHQVVACZ-UHFFFAOYSA-N 4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethoxy)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(OC(F)(F)F)=CC=C3N=2)=C1 XRLZWRIHQVVACZ-UHFFFAOYSA-N 0.000 claims description 2
PBXFRAFAGCEVSF-UHFFFAOYSA-N 4-[3-(6-cyclopropylpyridin-3-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC2=CC(C(F)(F)F)=CC=C2N=C1C(C=1)=CC=CC=1C(C=N1)=CC=C1C1CC1 PBXFRAFAGCEVSF-UHFFFAOYSA-N 0.000 claims description 2
VMEZSFFCHLCBBK-UHFFFAOYSA-N 7,8-dichloro-4-(3-pyridin-4-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound N=1C=2C=C(Cl)C(Cl)=CC=2NC(=O)CC=1C(C=1)=CC=CC=1C1=CC=NC=C1 VMEZSFFCHLCBBK-UHFFFAOYSA-N 0.000 claims description 2
HXTQTHUBKDBECJ-UHFFFAOYSA-N 7,8-dichloro-4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(Cl)=C(Cl)C=C3N=2)=C1 HXTQTHUBKDBECJ-UHFFFAOYSA-N 0.000 claims description 2
DZCFLWXSUXKAJI-UHFFFAOYSA-N 7-(dimethylamino)-4-(3-pyridin-3-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(N(C)C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=CN=C1 DZCFLWXSUXKAJI-UHFFFAOYSA-N 0.000 claims description 2
YQKASQGOPRPMLH-UHFFFAOYSA-N 7-(dimethylamino)-4-(3-pyridin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(N(C)C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 YQKASQGOPRPMLH-UHFFFAOYSA-N 0.000 claims description 2
CCOJJDFNFUBNKN-UHFFFAOYSA-N 7-(dimethylamino)-4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(N(C)C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC(C)=C1 CCOJJDFNFUBNKN-UHFFFAOYSA-N 0.000 claims description 2
AHDAHZZDQMCLJT-UHFFFAOYSA-N 7-chloro-4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(Cl)C=C3N=2)C(F)(F)F)=C1 AHDAHZZDQMCLJT-UHFFFAOYSA-N 0.000 claims description 2
QFBDRSIFOKYSDY-UHFFFAOYSA-N 7-ethoxy-4-(3-pyridin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(OCC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 QFBDRSIFOKYSDY-UHFFFAOYSA-N 0.000 claims description 2
QCDLBZFFNJYTAV-UHFFFAOYSA-N 7-ethyl-4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(CC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC(C)=C1 QCDLBZFFNJYTAV-UHFFFAOYSA-N 0.000 claims description 2
OQTSPIQICMTNOL-UHFFFAOYSA-N 7-methyl-4-(3-pyridazin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NN=C1 OQTSPIQICMTNOL-UHFFFAOYSA-N 0.000 claims description 2
NZWUYDARLBVUAZ-UHFFFAOYSA-N 8-(2-fluorophenyl)-4-(3-pyridin-3-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound FC1=CC=CC=C1C1=CC=C(N=C(CC(=O)N2)C=3C=C(C=CC=3)C=3C=NC=CC=3)C2=C1 NZWUYDARLBVUAZ-UHFFFAOYSA-N 0.000 claims description 2
DEOUQGPUEWWMNC-UHFFFAOYSA-N 8-(2-fluorophenyl)-4-(3-pyridin-4-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound FC1=CC=CC=C1C1=CC=C(N=C(CC(=O)N2)C=3C=C(C=CC=3)C=3C=CN=CC=3)C2=C1 DEOUQGPUEWWMNC-UHFFFAOYSA-N 0.000 claims description 2
VBTRNVBPGJSEAM-UHFFFAOYSA-N 8-(2-fluorophenyl)-4-(3-pyrimidin-5-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound FC1=CC=CC=C1C1=CC=C(N=C(CC(=O)N2)C=3C=C(C=CC=3)C=3C=NC=NC=3)C2=C1 VBTRNVBPGJSEAM-UHFFFAOYSA-N 0.000 claims description 2
LKVQKLAWCNGKSL-UHFFFAOYSA-N 8-(2-fluorophenyl)-4-[3-(2-methylpyridin-4-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=CC=C3N=2)C=2C(=CC=CC=2)F)=C1 LKVQKLAWCNGKSL-UHFFFAOYSA-N 0.000 claims description 2
RRJHUDLALLDKRL-UHFFFAOYSA-N 8-chloro-4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-7-methyl-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(Cl)=C(C)C=C3N=2)=C1 RRJHUDLALLDKRL-UHFFFAOYSA-N 0.000 claims description 2
JLXAVOQTRVUYKG-UHFFFAOYSA-N 8-chloro-4-[3-(2-methylpyridin-3-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC=CC=C1C1=CC=CC(C=2CC(=O)NC3=CC(Cl)=CC=C3N=2)=C1 JLXAVOQTRVUYKG-UHFFFAOYSA-N 0.000 claims description 2
PRPOBZJPAWDSGQ-UHFFFAOYSA-N 8-chloro-4-[3-(2-methylpyridin-4-yl)phenyl]-7-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(Cl)=C(C=C3N=2)C(F)(F)F)=C1 PRPOBZJPAWDSGQ-UHFFFAOYSA-N 0.000 claims description 2
VOUQMUWKUYFRJK-UHFFFAOYSA-N 8-chloro-4-[3-(6-methylpyridin-3-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC=C1C1=CC=CC(C=2CC(=O)NC3=CC(Cl)=CC=C3N=2)=C1 VOUQMUWKUYFRJK-UHFFFAOYSA-N 0.000 claims description 2
ITPMBZMJFFOBBB-UHFFFAOYSA-N 8-chloro-7-methyl-4-(3-pyridazin-4-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NN=C1 ITPMBZMJFFOBBB-UHFFFAOYSA-N 0.000 claims description 2
QPHSKVNFGZIDPN-UHFFFAOYSA-N 8-chloro-7-methyl-4-(3-pyridin-4-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(Cl)C(C)=CC=2N=C1C(C=1)=CC=CC=1C1=CC=NC=C1 QPHSKVNFGZIDPN-UHFFFAOYSA-N 0.000 claims description 2
CWZIXKLALYDKHJ-UHFFFAOYSA-N 8-chloro-7-methyl-4-[3-(2-methylpyridin-4-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(Cl)=C(C)C=C3N=2)=C1 CWZIXKLALYDKHJ-UHFFFAOYSA-N 0.000 claims description 2
YJSYRZKLIDMQGG-UHFFFAOYSA-N 8-fluoro-4-[3-(2-methylpyridin-4-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(F)=CC=C3N=2)=C1 YJSYRZKLIDMQGG-UHFFFAOYSA-N 0.000 claims description 2
QRDOMCFVXRYHRK-UHFFFAOYSA-N 8-methyl-4-(3-pyridin-4-ylphenyl)-7-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound N=1C=2C=C(C(F)(F)F)C(C)=CC=2NC(=O)CC=1C(C=1)=CC=CC=1C1=CC=NC=C1 QRDOMCFVXRYHRK-UHFFFAOYSA-N 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
238000010511 deprotection reaction Methods 0.000 claims description 2
125000003373 pyrazinyl group Chemical group 0.000 claims description 2
125000002098 pyridazinyl group Chemical group 0.000 claims description 2
LYTVXCQQTLUEQR-UHFFFAOYSA-N ro4491533 Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(C)C=C3N=2)C(F)(F)F)=C1 LYTVXCQQTLUEQR-UHFFFAOYSA-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
125000005843 halogen group Chemical group 0.000 claims 9
239000000126 substance Substances 0.000 claims 8
230000006806 disease prevention Effects 0.000 claims 3
UVNQIBJKZJJBQK-UHFFFAOYSA-N 4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-7-ethyl-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(CC)=CC=2N=C1C(C=1)=CC=CC=1C1=CC(C)=NC(C)=C1 UVNQIBJKZJJBQK-UHFFFAOYSA-N 0.000 claims 1
CLEXCUYVRGOQCW-UHFFFAOYSA-N 4-[3-(2,6-dimethylpyridin-4-yl)phenyl]-8-methyl-7-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(C)=C(C=C3N=2)C(F)(F)F)=C1 CLEXCUYVRGOQCW-UHFFFAOYSA-N 0.000 claims 1
AFSJGBXRHLXBHV-UHFFFAOYSA-N 4-[3-(2-ethyl-6-methylpyridin-4-yl)phenyl]-7-methyl-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC(CC)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(C)C=C3N=2)C(F)(F)F)=C1 AFSJGBXRHLXBHV-UHFFFAOYSA-N 0.000 claims 1
MTRZSMDLMJKFMC-UHFFFAOYSA-N 4-[3-(6-methylpyrimidin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=CC=C3N=2)C(F)(F)F)=N1 MTRZSMDLMJKFMC-UHFFFAOYSA-N 0.000 claims 1
CUBHTWLIWFXCKK-UHFFFAOYSA-N 7,8-dichloro-4-(3-pyridin-3-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound N=1C=2C=C(Cl)C(Cl)=CC=2NC(=O)CC=1C(C=1)=CC=CC=1C1=CC=CN=C1 CUBHTWLIWFXCKK-UHFFFAOYSA-N 0.000 claims 1
UJVWWZXXZMKDKY-UHFFFAOYSA-N 7,8-dichloro-4-[3-(2-methylpyridin-4-yl)phenyl]-2,3-dihydro-1H-1,5-benzodiazepine Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CCNC3=CC(Cl)=C(Cl)C=C3N=2)=C1 UJVWWZXXZMKDKY-UHFFFAOYSA-N 0.000 claims 1
BAXARIOGPJRTLH-UHFFFAOYSA-N 7-(cyclopropylmethoxy)-4-[3-(2-methylpyridin-4-yl)phenyl]-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C=2CC(=O)NC3=CC(=C(OCC4CC4)C=C3N=2)C(F)(F)F)=C1 BAXARIOGPJRTLH-UHFFFAOYSA-N 0.000 claims 1
GXQISOFEZQYHPI-UHFFFAOYSA-N 7-[methyl(propyl)amino]-4-(3-pyrazin-2-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1C(=O)NC=2C=C(C(F)(F)F)C(N(C)CCC)=CC=2N=C1C(C=1)=CC=CC=1C1=CN=CC=N1 GXQISOFEZQYHPI-UHFFFAOYSA-N 0.000 claims 1
OPUCFSUMZCYZKN-UHFFFAOYSA-N 7-chloro-4-(3-pyridin-4-ylphenyl)-8-(trifluoromethyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound N=1C=2C=C(Cl)C(C(F)(F)F)=CC=2NC(=O)CC=1C(C=1)=CC=CC=1C1=CC=NC=C1 OPUCFSUMZCYZKN-UHFFFAOYSA-N 0.000 claims 1
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QHWRKFWOOXWYMW-UHFFFAOYSA-N 8-(2-fluorophenyl)-4-[3-(2-methylpyridin-3-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound CC1=NC=CC=C1C1=CC=CC(C=2CC(=O)NC3=CC(=CC=C3N=2)C=2C(=CC=CC=2)F)=C1 QHWRKFWOOXWYMW-UHFFFAOYSA-N 0.000 claims 1
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Classifications

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- C07—ORGANIC CHEMISTRY
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Psychiatry (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Hydrogenated Pyridines (AREA)

ZA200406032A 2002-02-06 2004-07-28 Dihydrobenzodiazepin-2-one derivatives for the treatment of neurological disorders. ZA200406032B (en)

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EP02002012		2002-02-06

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ZA200406032A ZA200406032B (en)	2002-02-06	2004-07-28	Dihydrobenzodiazepin-2-one derivatives for the treatment of neurological disorders.

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US (1)	US6949542B2 (es)
EP (1)	EP1474416B1 (es)
JP (1)	JP4077411B2 (es)
KR (1)	KR20040081486A (es)
CN (1)	CN100497333C (es)
AR (1)	AR038481A1 (es)
AT (1)	ATE374196T1 (es)
AU (1)	AU2003205695B8 (es)
BR (1)	BR0307474A (es)
CA (1)	CA2474219C (es)
DE (1)	DE60316538T2 (es)
DK (1)	DK1474416T3 (es)
ES (1)	ES2294264T3 (es)
GT (1)	GT200300028A (es)
HR (1)	HRP20040678A2 (es)
IL (1)	IL163102A (es)
MX (1)	MXPA04007516A (es)
MY (1)	MY176608A (es)
NO (1)	NO327697B1 (es)
NZ (1)	NZ534122A (es)
PA (1)	PA8565901A1 (es)
PE (1)	PE20031011A1 (es)
PL (1)	PL372425A1 (es)
PT (1)	PT1474416E (es)
RU (1)	RU2315764C2 (es)
SI (1)	SI1474416T1 (es)
TW (1)	TWI326599B (es)
UY (1)	UY27654A1 (es)
WO (1)	WO2003066623A1 (es)
ZA (1)	ZA200406032B (es)

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2003
- 2003-01-24 US US10/350,713 patent/US6949542B2/en not_active Expired - Lifetime
- 2003-01-28 BR BR0307474-9A patent/BR0307474A/pt not_active Application Discontinuation
- 2003-01-28 NZ NZ534122A patent/NZ534122A/en not_active IP Right Cessation
- 2003-01-28 SI SI200331034T patent/SI1474416T1/sl unknown
- 2003-01-28 KR KR10-2004-7012084A patent/KR20040081486A/ko not_active Ceased
- 2003-01-28 EP EP03702549A patent/EP1474416B1/en not_active Expired - Lifetime
- 2003-01-28 PL PL03372425A patent/PL372425A1/xx not_active Application Discontinuation
- 2003-01-28 HR HR20040678A patent/HRP20040678A2/hr not_active Application Discontinuation
- 2003-01-28 MX MXPA04007516A patent/MXPA04007516A/es active IP Right Grant
- 2003-01-28 DE DE60316538T patent/DE60316538T2/de not_active Expired - Lifetime
- 2003-01-28 CA CA2474219A patent/CA2474219C/en not_active Expired - Fee Related
- 2003-01-28 RU RU2004126945/04A patent/RU2315764C2/ru not_active IP Right Cessation
- 2003-01-28 WO PCT/EP2003/000859 patent/WO2003066623A1/en not_active Ceased
- 2003-01-28 JP JP2003565996A patent/JP4077411B2/ja not_active Expired - Fee Related
- 2003-01-28 PT PT03702549T patent/PT1474416E/pt unknown
- 2003-01-28 DK DK03702549T patent/DK1474416T3/da active
- 2003-01-28 ES ES03702549T patent/ES2294264T3/es not_active Expired - Lifetime
- 2003-01-28 AT AT03702549T patent/ATE374196T1/de active
- 2003-01-28 AU AU2003205695A patent/AU2003205695B8/en not_active Ceased
- 2003-01-28 CN CNB038065452A patent/CN100497333C/zh not_active Expired - Fee Related
- 2003-01-30 TW TW092102234A patent/TWI326599B/zh active
- 2003-02-03 GT GT200300028A patent/GT200300028A/es unknown
- 2003-02-03 PE PE2003000122A patent/PE20031011A1/es not_active Application Discontinuation
- 2003-02-04 AR ARP030100334A patent/AR038481A1/es unknown
- 2003-02-05 PA PA20038565901A patent/PA8565901A1/es unknown
- 2003-02-05 MY MYPI20030378A patent/MY176608A/en unknown
- 2003-02-05 UY UY27654A patent/UY27654A1/es not_active Application Discontinuation
2004
- 2004-07-19 IL IL163102A patent/IL163102A/en not_active IP Right Cessation
- 2004-07-28 ZA ZA200406032A patent/ZA200406032B/en unknown
- 2004-08-02 NO NO20043237A patent/NO327697B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
US6949542B2 (en)	2005-09-27
CN1633430A (zh)	2005-06-29
AU2003205695B8 (en)	2008-05-01
JP2005522440A (ja)	2005-07-28
HK1078858A1 (zh)	2006-03-24
EP1474416B1 (en)	2007-09-26
PT1474416E (pt)	2007-12-27
PA8565901A1 (es)	2003-09-05
CA2474219C (en)	2010-04-13
AU2003205695B2 (en)	2008-04-03
GT200300028A (es)	2004-06-11
NO20043237L (no)	2004-08-02
NO327697B1 (no)	2009-09-14
PE20031011A1 (es)	2003-11-29
MY176608A (en)	2020-08-18
CA2474219A1 (en)	2003-08-14
DE60316538T2 (de)	2008-08-21
WO2003066623A1 (en)	2003-08-14
KR20040081486A (ko)	2004-09-21
AR038481A1 (es)	2005-01-19
RU2004126945A (ru)	2005-06-27
CN100497333C (zh)	2009-06-10
EP1474416A1 (en)	2004-11-10
MXPA04007516A (es)	2004-11-10
AU2003205695A1 (en)	2003-09-02
IL163102A (en)	2011-07-31
PL372425A1 (en)	2005-07-25
UY27654A1 (es)	2003-08-29
US20030166639A1 (en)	2003-09-04
ES2294264T3 (es)	2008-04-01
HRP20040678A2 (en)	2005-10-31
SI1474416T1 (sl)	2008-02-29
TWI326599B (en)	2010-07-01
JP4077411B2 (ja)	2008-04-16
NZ534122A (en)	2006-12-22
TW200302730A (en)	2003-08-16
DE60316538D1 (de)	2007-11-08
ATE374196T1 (de)	2007-10-15
DK1474416T3 (da)	2008-01-14
RU2315764C2 (ru)	2008-01-27
BR0307474A (pt)	2004-11-09

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