AU2004276002B2 - Amidomethyl substituted 1-(carboxyalkyl)-cyclopentylcarbonylamino-benzazepine-N-acetic acid derivatives, process and intermediate products for their preparation and medicaments containing these compounds - Google Patents

Info

Publication number

AU2004276002B2

AU2004276002B2 AU2004276002A AU2004276002A AU2004276002B2 AU 2004276002 B2 AU2004276002 B2 AU 2004276002B2 AU 2004276002 A AU2004276002 A AU 2004276002A AU 2004276002 A AU2004276002 A AU 2004276002A AU 2004276002 B2 AU2004276002 B2 AU 2004276002B2

Authority

AU

Australia

Prior art keywords

amino

methyl

alkyl

oxo

carbonyl

Prior art date

2003-09-26

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

Links

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• 238000000034 method Methods 0.000 title claims description 49
• 238000002360 preparation method Methods 0.000 title claims description 28
• 239000003814 drug Substances 0.000 title claims description 19
• 230000008569 process Effects 0.000 title claims description 14
• 239000013067 intermediate product Substances 0.000 title description 8
• -1 phenylcarbonylmethyl Chemical group 0.000 claims description 74
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 71
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 60
• 239000002253 acid Substances 0.000 claims description 57
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 51
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 47
• 238000011282 treatment Methods 0.000 claims description 36
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
• 150000007513 acids Chemical class 0.000 claims description 29
• 150000003839 salts Chemical class 0.000 claims description 29
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
• 150000002148 esters Chemical class 0.000 claims description 26
• 206010057671 Female sexual dysfunction Diseases 0.000 claims description 24
• 125000000539 amino acid group Chemical group 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 21
• 239000001257 hydrogen Substances 0.000 claims description 21
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• 201000001881 impotence Diseases 0.000 claims description 18
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 11
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
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• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 150000001721 carbon Chemical group 0.000 claims description 6
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• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
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• DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical group N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 claims description 4
• 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 4
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 4
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• YWKXBEFYDKOMJL-UHFFFAOYSA-N 2-[[1-[[1-(carboxymethyl)-2-oxo-4,5-dihydro-3h-1-benzazepin-3-yl]carbamoyl]cyclopentyl]methyl]-4-[3-hydroxypropyl(methyl)amino]-4-oxobutanoic acid Chemical compound C1CC2=CC=CC=C2N(CC(O)=O)C(=O)C1NC(=O)C1(CC(CC(=O)N(CCCO)C)C(O)=O)CCCC1 YWKXBEFYDKOMJL-UHFFFAOYSA-N 0.000 claims description 3
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• BDMJNYVQOMEGPI-UHFFFAOYSA-N 4-[bis(2-hydroxyethyl)amino]-2-[[1-[[1-(carboxymethyl)-2-oxo-4,5-dihydro-3h-1-benzazepin-3-yl]carbamoyl]cyclopentyl]methyl]-4-oxobutanoic acid Chemical compound C1CC2=CC=CC=C2N(CC(O)=O)C(=O)C1NC(=O)C1(CC(CC(=O)N(CCO)CCO)C(O)=O)CCCC1 BDMJNYVQOMEGPI-UHFFFAOYSA-N 0.000 claims description 3
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• HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims description 3
• MDIRESITLMKUFA-UHFFFAOYSA-N 4-[3-aminopropyl(ethyl)amino]-2-[[1-[[1-(carboxymethyl)-2-oxo-4,5-dihydro-3h-1-benzazepin-3-yl]carbamoyl]cyclopentyl]methyl]-4-oxobutanoic acid Chemical compound C1CC2=CC=CC=C2N(CC(O)=O)C(=O)C1NC(=O)C1(CC(CC(=O)N(CCCN)CC)C(O)=O)CCCC1 MDIRESITLMKUFA-UHFFFAOYSA-N 0.000 claims description 2
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• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
• BQVAEKFFIBBGBW-UHFFFAOYSA-N 2-[[1-[[1-(carboxymethyl)-2-oxo-4,5-dihydro-3h-1-benzazepin-3-yl]carbamoyl]cyclopentyl]methyl]-4-morpholin-4-yl-4-oxobutanoic acid Chemical compound O=C1N(CC(=O)O)C2=CC=CC=C2CCC1NC(=O)C1(CC(CC(=O)N2CCOCC2)C(O)=O)CCCC1 BQVAEKFFIBBGBW-UHFFFAOYSA-N 0.000 claims 1
• UAUGBPQYORBALH-UHFFFAOYSA-N 4-[4-aminobutyl(methyl)amino]-2-[[1-[[1-(carboxymethyl)-2-oxo-4,5-dihydro-3h-1-benzazepin-3-yl]carbamoyl]cyclopentyl]methyl]-4-oxobutanoic acid Chemical compound C1CC2=CC=CC=C2N(CC(O)=O)C(=O)C1NC(=O)C1(CC(CC(=O)N(CCCCN)C)C(O)=O)CCCC1 UAUGBPQYORBALH-UHFFFAOYSA-N 0.000 claims 1
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