AU2007303056A1 - Bicyclic nitrogen-containing heterocyclic compounds for use as stearoyl CoA desaturase inhibitors - Google Patents

Info

Publication number

AU2007303056A1

AU2007303056A1 AU2007303056A AU2007303056A AU2007303056A1 AU 2007303056 A1 AU2007303056 A1 AU 2007303056A1 AU 2007303056 A AU2007303056 A AU 2007303056A AU 2007303056 A AU2007303056 A AU 2007303056A AU 2007303056 A1 AU2007303056 A1 AU 2007303056A1

Authority

AU

Australia

Prior art keywords

amino

methyl

oxo

hydropyridino

pyrazin

Prior art date

2006-10-05

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• -1 Bicyclic nitrogen-containing heterocyclic compounds Chemical class 0.000 title claims description 123
• 108010087894 Fatty acid desaturases Proteins 0.000 title claims description 64
• 102000016553 Stearoyl-CoA Desaturase Human genes 0.000 title claims 2
• 239000003112 inhibitor Substances 0.000 title description 12
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 287
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 214
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 175
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 166
• 150000001875 compounds Chemical class 0.000 claims description 160
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 118
• 125000000217 alkyl group Chemical group 0.000 claims description 94
• 125000003118 aryl group Chemical group 0.000 claims description 70
• 125000001072 heteroaryl group Chemical group 0.000 claims description 70
• 125000001424 substituent group Chemical group 0.000 claims description 54
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 51
• 201000010099 disease Diseases 0.000 claims description 37
• 238000000034 method Methods 0.000 claims description 35
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
• 125000000623 heterocyclic group Chemical group 0.000 claims description 34
• 125000003545 alkoxy group Chemical group 0.000 claims description 29
• 125000003342 alkenyl group Chemical group 0.000 claims description 27
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 27
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
• 239000001257 hydrogen Substances 0.000 claims description 21
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 125000000304 alkynyl group Chemical group 0.000 claims description 20
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 20
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
• 125000002947 alkylene group Chemical group 0.000 claims description 18
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 17
• 150000003839 salts Chemical class 0.000 claims description 17
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 8
• 239000002253 acid Substances 0.000 claims description 8
• 241000124008 Mammalia Species 0.000 claims description 7
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 7
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
• 150000002148 esters Chemical class 0.000 claims description 6
• 230000002401 inhibitory effect Effects 0.000 claims description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
• 239000000651 prodrug Substances 0.000 claims description 5
• 229940002612 prodrug Drugs 0.000 claims description 5
• 235000019260 propionic acid Nutrition 0.000 claims description 5
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 4
• 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims description 4
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 4
• 239000005711 Benzoic acid Substances 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 235000010233 benzoic acid Nutrition 0.000 claims description 3
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
• 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
• 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
• 239000005977 Ethylene Substances 0.000 claims description 2
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 2
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• NIPZZXUFJPQHNH-UHFFFAOYSA-M pyrazine-2-carboxylate Chemical compound [O-]C(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-M 0.000 claims description 2
• NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 6
• XZOWIJDBQIHMFC-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O.CCCC(N)=O XZOWIJDBQIHMFC-UHFFFAOYSA-N 0.000 claims 5
• 125000001475 halogen functional group Chemical group 0.000 claims 5
• WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 claims 1
• WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 claims 1
• LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 claims 1
• 102100028897 Stearoyl-CoA desaturase Human genes 0.000 description 60
• 239000000203 mixture Substances 0.000 description 59
• 238000002360 preparation method Methods 0.000 description 38
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
• 150000001412 amines Chemical class 0.000 description 24
• 229910052736 halogen Inorganic materials 0.000 description 23
• 150000002367 halogens Chemical class 0.000 description 23
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 22
• 125000004181 carboxyalkyl group Chemical group 0.000 description 22
• 238000006243 chemical reaction Methods 0.000 description 22
• 125000004093 cyano group Chemical group *C#N 0.000 description 22
• 230000000694 effects Effects 0.000 description 20
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 20
• 239000000243 solution Substances 0.000 description 20
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 19
• 238000009472 formulation Methods 0.000 description 19
• 125000004432 carbon atom Chemical group C* 0.000 description 18
• 239000002904 solvent Substances 0.000 description 18
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 17
• 125000000392 cycloalkenyl group Chemical group 0.000 description 17
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
• 235000014113 dietary fatty acids Nutrition 0.000 description 14
• 208000035475 disorder Diseases 0.000 description 14
• 239000000194 fatty acid Substances 0.000 description 14
• 229930195729 fatty acid Natural products 0.000 description 14
• 230000001404 mediated effect Effects 0.000 description 13
• 241001465754 Metazoa Species 0.000 description 12
• 150000004665 fatty acids Chemical class 0.000 description 12
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 12
• 239000000725 suspension Substances 0.000 description 12
• 150000002632 lipids Chemical class 0.000 description 11
• 238000011282 treatment Methods 0.000 description 11
• 208000008589 Obesity Diseases 0.000 description 10
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• 125000004414 alkyl thio group Chemical group 0.000 description 10
• 238000003556 assay Methods 0.000 description 10
• 150000003857 carboxamides Chemical class 0.000 description 10
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 10
• 239000003995 emulsifying agent Substances 0.000 description 10
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• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
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• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
• 208000032928 Dyslipidaemia Diseases 0.000 description 9
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
• 229930194542 Keto Natural products 0.000 description 9
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 9
• 125000002252 acyl group Chemical group 0.000 description 9
• 125000004442 acylamino group Chemical group 0.000 description 9
• 125000004423 acyloxy group Chemical group 0.000 description 9
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