TWI326599B - Dihydrobenzodiazepin-2-one derivatives, pharmaceutical composition comprising the same, process for preparing the same, and use thereof - Google Patents

Info

Publication number

TWI326599B

TWI326599B TW092102234A TW92102234A TWI326599B TW I326599 B TWI326599 B TW I326599B TW 092102234 A TW092102234 A TW 092102234A TW 92102234 A TW92102234 A TW 92102234A TW I326599 B TWI326599 B TW I326599B

Authority

TW

Taiwan

Prior art keywords

phenyl

methyl

mmol

butyl ester

group

Prior art date

2002-02-06

Links

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• 238000004519 manufacturing process Methods 0.000 title claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 title claims 2
• 238000000034 method Methods 0.000 claims description 704
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• -1 acetylene diyl group Chemical group 0.000 claims description 572
• 239000002253 acid Substances 0.000 claims description 308
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 78
• 125000000217 alkyl group Chemical group 0.000 claims description 62
• 239000007789 gas Substances 0.000 claims description 50
• 125000003545 alkoxy group Chemical group 0.000 claims description 40
• 239000001257 hydrogen Substances 0.000 claims description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 33
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• 150000001412 amines Chemical class 0.000 claims description 31
• 239000010949 copper Substances 0.000 claims description 30
• 125000003277 amino group Chemical group 0.000 claims description 24
• 150000002431 hydrogen Chemical group 0.000 claims description 24
• 229910052802 copper Inorganic materials 0.000 claims description 23
• 150000002576 ketones Chemical class 0.000 claims description 22
• 125000001424 substituent group Chemical group 0.000 claims description 22
• 150000003839 salts Chemical class 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 150000002367 halogens Chemical group 0.000 claims description 19
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
• 125000001153 fluoro group Chemical group F* 0.000 claims description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
• 125000003282 alkyl amino group Chemical group 0.000 claims description 13
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 13
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• ODRZAZBEQWAOGU-UHFFFAOYSA-N 1,4-dioxin-2-one Chemical compound O=C1COC=CO1 ODRZAZBEQWAOGU-UHFFFAOYSA-N 0.000 claims description 10
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
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• 230000001154 acute effect Effects 0.000 claims description 6
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• 125000003118 aryl group Chemical group 0.000 claims description 5
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
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• ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 4
• 201000000980 schizophrenia Diseases 0.000 claims description 4
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• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 2
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 2
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• 238000010511 deprotection reaction Methods 0.000 claims 1
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• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
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• 208000020016 psychiatric disease Diseases 0.000 claims 1
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• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 161
• 238000002844 melting Methods 0.000 description 135
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 128
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
• 239000003921 oil Substances 0.000 description 78
• 235000019198 oils Nutrition 0.000 description 78
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 69
• 239000000243 solution Substances 0.000 description 67
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 66
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 64
• 239000000463 material Substances 0.000 description 56
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• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 48
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 47
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
• 239000002904 solvent Substances 0.000 description 43
• XDBHWPLGGBLUHH-UHFFFAOYSA-N (3-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C#N)=C1 XDBHWPLGGBLUHH-UHFFFAOYSA-N 0.000 description 38
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 37
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 37
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
• RENOIBALUBTYLS-UHFFFAOYSA-N tert-butyl 3-[3-(2-methylpyridin-4-yl)phenyl]-3-oxopropanoate Chemical compound C1=NC(C)=CC(C=2C=C(C=CC=2)C(=O)CC(=O)OC(C)(C)C)=C1 RENOIBALUBTYLS-UHFFFAOYSA-N 0.000 description 34
• AEHYHZHQKIYWHR-UHFFFAOYSA-N tert-butyl 3-oxo-3-(3-pyridin-3-ylphenyl)propanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1=CC=CC(C=2C=NC=CC=2)=C1 AEHYHZHQKIYWHR-UHFFFAOYSA-N 0.000 description 32
• 239000012267 brine Substances 0.000 description 30
• 238000006243 chemical reaction Methods 0.000 description 30
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 30
• 238000005984 hydrogenation reaction Methods 0.000 description 29
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 28
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• 229940024606 amino acid Drugs 0.000 description 27
• 150000002148 esters Chemical class 0.000 description 27
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• 229920006395 saturated elastomer Polymers 0.000 description 25
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 25
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• 238000004440 column chromatography Methods 0.000 description 24
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• 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 19
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• 239000011541 reaction mixture Substances 0.000 description 18
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• 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 13
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