NL1027434C2 - Bicyclische pyrazolyl- en imidazolylverbindingen, en toepassingen daarvan. - Google Patents

Info

Publication number

NL1027434C2

NL1027434C2 NL1027434A NL1027434A NL1027434C2 NL 1027434 C2 NL1027434 C2 NL 1027434C2 NL 1027434 A NL1027434 A NL 1027434A NL 1027434 A NL1027434 A NL 1027434A NL 1027434 C2 NL1027434 C2 NL 1027434C2

Authority

NL

Netherlands

Prior art keywords

chlorophenyl

compound

azulene

trifluoroethyl

alkyl

Prior art date

2003-11-07

Links

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• 125000002883 imidazolyl group Chemical group 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims description 254
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 63
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 61
• 125000001424 substituent group Chemical group 0.000 claims description 61
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 55
• 238000002360 preparation method Methods 0.000 claims description 53
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 52
• 150000003839 salts Chemical class 0.000 claims description 43
• 125000003118 aryl group Chemical group 0.000 claims description 38
• 208000035475 disorder Diseases 0.000 claims description 36
• 229910052757 nitrogen Inorganic materials 0.000 claims description 35
• 239000003814 drug Substances 0.000 claims description 34
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 33
• 125000000623 heterocyclic group Chemical group 0.000 claims description 31
• 239000000556 agonist Substances 0.000 claims description 28
• 229920006395 saturated elastomer Polymers 0.000 claims description 28
• 239000000126 substance Substances 0.000 claims description 28
• 125000001072 heteroaryl group Chemical group 0.000 claims description 27
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
• 125000000217 alkyl group Chemical group 0.000 claims description 24
• 239000005557 antagonist Substances 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 239000003795 chemical substances by application Substances 0.000 claims description 22
• 239000001257 hydrogen Substances 0.000 claims description 21
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 20
• 229910052799 carbon Inorganic materials 0.000 claims description 20
• 239000003112 inhibitor Substances 0.000 claims description 20
• 239000008177 pharmaceutical agent Substances 0.000 claims description 20
• 239000012453 solvate Substances 0.000 claims description 20
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 17
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• 239000000651 prodrug Substances 0.000 claims description 15
• 229940002612 prodrug Drugs 0.000 claims description 15
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 14
• 125000002837 carbocyclic group Chemical group 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• 239000003085 diluting agent Substances 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 229910052717 sulfur Chemical group 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
• 239000001301 oxygen Substances 0.000 claims description 11
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 10
• 125000002252 acyl group Chemical group 0.000 claims description 10
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 10
• 150000003951 lactams Chemical class 0.000 claims description 10
• 229940044601 receptor agonist Drugs 0.000 claims description 10
• 239000000018 receptor agonist Substances 0.000 claims description 10
• FJMQJSUOOGOWBD-UHFFFAOYSA-N 2-(2-chlorophenyl)-3-(4-chlorophenyl)-7-(2,2-difluoropropyl)-5,6-dihydropyrazolo[3,4-f][1,4]oxazepin-8-one Chemical compound O=C1N(CC(F)(F)C)CCOC=2C1=NN(C=1C(=CC=CC=1)Cl)C=2C1=CC=C(Cl)C=C1 FJMQJSUOOGOWBD-UHFFFAOYSA-N 0.000 claims description 9
• 229940122820 Cannabinoid receptor antagonist Drugs 0.000 claims description 9
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
• 239000003536 cannabinoid receptor antagonist Substances 0.000 claims description 9
• 229940044551 receptor antagonist Drugs 0.000 claims description 9
• 239000002464 receptor antagonist Substances 0.000 claims description 9
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• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
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• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 6
• RBPQIDPWBPCGOF-UHFFFAOYSA-N 5h-azulen-4-one Chemical compound O=C1CC=CC=C2C=CC=C12 RBPQIDPWBPCGOF-UHFFFAOYSA-N 0.000 claims description 6
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• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000005843 halogen group Chemical group 0.000 claims description 5
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• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 3
• YNPOBTNBSTZIKR-UHFFFAOYSA-N 2-(2-chlorophenyl)-3-(4-chlorophenyl)-4,6,6-trimethyl-7-(2,2,2-trifluoroethyl)-5h-pyrazolo[4,3-e][1,4]diazepin-8-one Chemical compound C=12N(C)CC(C)(C)N(CC(F)(F)F)C(=O)C2=NN(C=2C(=CC=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 YNPOBTNBSTZIKR-UHFFFAOYSA-N 0.000 claims description 3
• LRZXYARISQFUKT-UHFFFAOYSA-N 2-(2-chlorophenyl)-3-(4-chlorophenyl)-7-(2,2-difluorobutyl)-5,6-dihydropyrazolo[3,4-f][1,4]oxazepin-8-one Chemical compound O=C1N(CC(F)(F)CC)CCOC=2C1=NN(C=1C(=CC=CC=1)Cl)C=2C1=CC=C(Cl)C=C1 LRZXYARISQFUKT-UHFFFAOYSA-N 0.000 claims description 3
• VBQDMCVGFGCEHT-UHFFFAOYSA-N 2-(2-chlorophenyl)-3-(4-chlorophenyl)-7-(2,2-difluoropropyl)-5,6-dihydroimidazo[4,5-f][1,4]oxazepin-8-one Chemical compound O=C1N(CC(F)(F)C)CCOC(N2C=3C=CC(Cl)=CC=3)=C1N=C2C1=CC=CC=C1Cl VBQDMCVGFGCEHT-UHFFFAOYSA-N 0.000 claims description 3
• ICKXKXNHQRHUMS-UHFFFAOYSA-N 2-(2-chlorophenyl)-3-(4-chlorophenyl)-7-propan-2-yl-5,6-dihydropyrazolo[3,4-f][1,4]oxazepin-8-one Chemical compound O=C1N(C(C)C)CCOC=2C1=NN(C=1C(=CC=CC=1)Cl)C=2C1=CC=C(Cl)C=C1 ICKXKXNHQRHUMS-UHFFFAOYSA-N 0.000 claims description 3
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• 101000928179 Homo sapiens Agouti-related protein Proteins 0.000 claims description 3
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