ZA200202654B - Benzodiazepine derivatives. - Google Patents
Benzodiazepine derivatives. Download PDFInfo
- Publication number
- ZA200202654B ZA200202654B ZA200202654A ZA200202654A ZA200202654B ZA 200202654 B ZA200202654 B ZA 200202654B ZA 200202654 A ZA200202654 A ZA 200202654A ZA 200202654 A ZA200202654 A ZA 200202654A ZA 200202654 B ZA200202654 B ZA 200202654B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- lower alkyl
- diazepin
- benzo
- dihydro
- Prior art date
Links
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 title description 2
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 54
- -1 benzyloxy, benzoyl Chemical group 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 14
- 125000004043 oxo group Chemical group O=* 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 230000001684 chronic effect Effects 0.000 claims description 7
- 208000024827 Alzheimer disease Diseases 0.000 claims description 6
- 208000026139 Memory disease Diseases 0.000 claims description 6
- 208000012902 Nervous system disease Diseases 0.000 claims description 6
- 208000025966 Neurological disease Diseases 0.000 claims description 6
- 208000028017 Psychotic disease Diseases 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 230000001154 acute effect Effects 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 208000010877 cognitive disease Diseases 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 201000000980 schizophrenia Diseases 0.000 claims description 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- AZIZBYRGIGKTLW-UHFFFAOYSA-N 1,4-diazepin-2-one Chemical compound O=C1C=NC=CC=N1 AZIZBYRGIGKTLW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 2
- IHTYSWGEFQVZAS-UHFFFAOYSA-N 2-[3-[8-(4-fluorophenyl)-2-oxo-1,3-dihydro-1,5-benzodiazepin-4-yl]phenyl]-n-(2-hydroxyethyl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NCCO)=C(C)N=C1C1=CC=CC(C=2CC(=O)NC3=CC(=CC=C3N=2)C=2C=CC(F)=CC=2)=C1 IHTYSWGEFQVZAS-UHFFFAOYSA-N 0.000 claims description 2
- KPUGPRGWUXMDLJ-UHFFFAOYSA-N 4-(3-chlorophenyl)-8-(2-phenylethynyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound ClC1=CC=CC(C=2CC(=O)NC3=CC(=CC=C3N=2)C#CC=2C=CC=CC=2)=C1 KPUGPRGWUXMDLJ-UHFFFAOYSA-N 0.000 claims description 2
- MEKAZEXGRUMQBA-UHFFFAOYSA-N 8-(2,3-difluorophenyl)-4-[3-(triazol-1-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound FC1=CC=CC(C=2C=C3NC(=O)CC(=NC3=CC=2)C=2C=C(C=CC=2)N2N=NC=C2)=C1F MEKAZEXGRUMQBA-UHFFFAOYSA-N 0.000 claims description 2
- CTRQMBIJPKBYBT-UHFFFAOYSA-N 8-(4-fluoro-2-hydroxyphenyl)-4-(3-imidazol-1-ylphenyl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound OC1=CC(F)=CC=C1C1=CC=C(N=C(CC(=O)N2)C=3C=C(C=CC=3)N3C=NC=C3)C2=C1 CTRQMBIJPKBYBT-UHFFFAOYSA-N 0.000 claims description 2
- SVXONALDAKPYCJ-UHFFFAOYSA-N 8-(4-fluorophenyl)-4-[3-(3-methyl-1,2-oxazol-5-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound O1N=C(C)C=C1C1=CC=CC(C=2CC(=O)NC3=CC(=CC=C3N=2)C=2C=CC(F)=CC=2)=C1 SVXONALDAKPYCJ-UHFFFAOYSA-N 0.000 claims description 2
- QXWDWFNHPHKTEJ-UHFFFAOYSA-N 8-[2-(4-fluorophenyl)ethynyl]-4-(2-imidazol-1-ylpyridin-4-yl)-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=CC(F)=CC=C1C#CC1=CC=C(N=C(CC(=O)N2)C=3C=C(N=CC=3)N3C=NC=C3)C2=C1 QXWDWFNHPHKTEJ-UHFFFAOYSA-N 0.000 claims description 2
- KNCGPBVBGQNEPA-UHFFFAOYSA-N 8-[2-(4-fluorophenyl)ethynyl]-4-[3-(tetrazol-1-yl)phenyl]-1,3-dihydro-1,5-benzodiazepin-2-one Chemical compound C1=CC(F)=CC=C1C#CC1=CC=C(N=C(CC(=O)N2)C=3C=C(C=CC=3)N3N=NN=C3)C2=C1 KNCGPBVBGQNEPA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000006251 butylcarbonyl group Chemical group 0.000 claims description 2
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 2
- 238000010511 deprotection reaction Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 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 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
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Applications Claiming Priority (1)
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EP (1) | EP1224175B1 (ja) |
JP (1) | JP3886805B2 (ja) |
KR (1) | KR100481386B1 (ja) |
CN (1) | CN1199954C (ja) |
AR (1) | AR026028A1 (ja) |
AT (1) | ATE261945T1 (ja) |
AU (1) | AU779874B2 (ja) |
BR (1) | BR0014761A (ja) |
CA (1) | CA2386980C (ja) |
CO (1) | CO5251454A1 (ja) |
CZ (1) | CZ20021663A3 (ja) |
DE (1) | DE60009116T2 (ja) |
DK (1) | DK1224175T3 (ja) |
ES (1) | ES2215738T3 (ja) |
GC (1) | GC0000207A (ja) |
HK (1) | HK1051037A1 (ja) |
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IL (2) | IL149104A0 (ja) |
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MA (1) | MA26832A1 (ja) |
MX (1) | MXPA02003740A (ja) |
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PE (1) | PE20010759A1 (ja) |
PL (1) | PL357433A1 (ja) |
PT (1) | PT1224175E (ja) |
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SI (1) | SI1224175T1 (ja) |
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WO (1) | WO2001029012A2 (ja) |
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