AU2005316314B2 - Thiazolopyridinone derivates as MCH receptor antagonists - Google Patents

Info

Publication number

AU2005316314B2

AU2005316314B2 AU2005316314A AU2005316314A AU2005316314B2 AU 2005316314 B2 AU2005316314 B2 AU 2005316314B2 AU 2005316314 A AU2005316314 A AU 2005316314A AU 2005316314 A AU2005316314 A AU 2005316314A AU 2005316314 B2 AU2005316314 B2 AU 2005316314B2

Authority

AU

Australia

Prior art keywords

phenyl

chloro

thiazolo

pyridin

methoxy

Prior art date

2004-12-17

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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• 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 title description 7
• BWCUYJUJJMCSLU-UHFFFAOYSA-N [1,3]thiazolo[5,4-b]pyridine 3-oxide Chemical compound C1=CN=C2S(=O)C=NC2=C1 BWCUYJUJJMCSLU-UHFFFAOYSA-N 0.000 title description 2
• 229940044551 receptor antagonist Drugs 0.000 title description 2
• 239000002464 receptor antagonist Substances 0.000 title description 2
• 102000006953 melanin-concentrating hormone receptor activity proteins Human genes 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 247
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 36
• 208000008589 Obesity Diseases 0.000 claims abstract description 32
• 235000020824 obesity Nutrition 0.000 claims abstract description 32
• 238000011282 treatment Methods 0.000 claims abstract description 22
• 201000010099 disease Diseases 0.000 claims abstract description 21
• 150000003839 salts Chemical class 0.000 claims abstract description 20
• -1 chloro, methoxy Chemical group 0.000 claims description 95
• 239000000203 mixture Substances 0.000 claims description 93
• 125000000217 alkyl group Chemical group 0.000 claims description 83
• GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 claims description 82
• 238000000034 method Methods 0.000 claims description 80
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 64
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 52
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
• 229910052757 nitrogen Inorganic materials 0.000 claims description 43
• 125000003118 aryl group Chemical group 0.000 claims description 37
• 125000000623 heterocyclic group Chemical group 0.000 claims description 37
• 229910052739 hydrogen Inorganic materials 0.000 claims description 35
• 239000001257 hydrogen Substances 0.000 claims description 35
• 125000005843 halogen group Chemical group 0.000 claims description 33
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 31
• DXKMDDUMYOCBSG-UHFFFAOYSA-N 5h-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound O=C1NC=CC2=C1SC=N2 DXKMDDUMYOCBSG-UHFFFAOYSA-N 0.000 claims description 26
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
• 125000003342 alkenyl group Chemical group 0.000 claims description 25
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 23
• 125000001188 haloalkyl group Chemical group 0.000 claims description 19
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 19
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• 208000035475 disorder Diseases 0.000 claims description 15
• 125000001424 substituent group Chemical group 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 208000025865 Ulcer Diseases 0.000 claims description 14
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 13
• 206010012601 diabetes mellitus Diseases 0.000 claims description 11
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 11
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• 125000004122 cyclic group Chemical group 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• 125000004076 pyridyl group Chemical group 0.000 claims description 10
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 9
• 125000004429 atom Chemical group 0.000 claims description 9
• 201000001320 Atherosclerosis Diseases 0.000 claims description 8
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 8
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
• 201000001421 hyperglycemia Diseases 0.000 claims description 8
• 125000004043 oxo group Chemical group O=* 0.000 claims description 8
• 108090000765 processed proteins & peptides Proteins 0.000 claims description 8
• 230000036269 ulceration Effects 0.000 claims description 8
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 7
• 206010009900 Colitis ulcerative Diseases 0.000 claims description 7
• 206010011224 Cough Diseases 0.000 claims description 7
• 208000011231 Crohn disease Diseases 0.000 claims description 7
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 7
• 206010012735 Diarrhoea Diseases 0.000 claims description 7
• 208000008279 Dumping Syndrome Diseases 0.000 claims description 7
• 208000007882 Gastritis Diseases 0.000 claims description 7
• 208000018522 Gastrointestinal disease Diseases 0.000 claims description 7
• 208000010412 Glaucoma Diseases 0.000 claims description 7
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 7
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 7
• 208000007920 Neurogenic Inflammation Diseases 0.000 claims description 7
• 208000000693 Neurogenic Urinary Bladder Diseases 0.000 claims description 7
• 206010029279 Neurogenic bladder Diseases 0.000 claims description 7
• 206010030216 Oesophagitis Diseases 0.000 claims description 7
• 208000032395 Post gastric surgery syndrome Diseases 0.000 claims description 7
• 206010036774 Proctitis Diseases 0.000 claims description 7
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 7
• 210000001367 artery Anatomy 0.000 claims description 7
• 208000006673 asthma Diseases 0.000 claims description 7
• 230000003247 decreasing effect Effects 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 230000004064 dysfunction Effects 0.000 claims description 7
• 230000004406 elevated intraocular pressure Effects 0.000 claims description 7
• 208000006881 esophagitis Diseases 0.000 claims description 7
• 230000002496 gastric effect Effects 0.000 claims description 7
• 230000010243 gut motility Effects 0.000 claims description 7
• 208000006575 hypertriglyceridemia Diseases 0.000 claims description 7
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 230000002093 peripheral effect Effects 0.000 claims description 7
• 208000017497 prostate disease Diseases 0.000 claims description 7
• NRAFIAPTASCPOX-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OCCN1CCCC1 NRAFIAPTASCPOX-UHFFFAOYSA-N 0.000 claims description 6
• 206010022714 Intestinal ulcer Diseases 0.000 claims description 6
• 125000005233 alkylalcohol group Chemical group 0.000 claims description 6
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000001072 heteroaryl group Chemical group 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• 231100000397 ulcer Toxicity 0.000 claims description 6
• TVEDENRTDWLOMQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-(3-pyrrolidin-1-ylpropyl)phenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3CC2)C=2C=CC(Cl)=CC=2)=O)=CC=C1CCCN1CCCC1 TVEDENRTDWLOMQ-UHFFFAOYSA-N 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• CYDIUTPFBMHRED-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[1-(2-pyrrolidin-1-ylethyl)indol-5-yl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound C1=CC(Cl)=CC=C1C(S1)=NC2=C1C(=O)N(C=1C=C3C=CN(CCN4CCCC4)C3=CC=1)CC2 CYDIUTPFBMHRED-UHFFFAOYSA-N 0.000 claims description 4
• IDKQBMBADBCOLZ-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[2,3-dimethyl-1-(2-pyrrolidin-1-ylethyl)indol-5-yl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound CC1=C(C)C2=CC(N3C(C=4SC(=NC=4CC3)C=3C=CC(Cl)=CC=3)=O)=CC=C2N1CCN1CCCC1 IDKQBMBADBCOLZ-UHFFFAOYSA-N 0.000 claims description 4
• DJPGJWARKQIVBZ-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-(3-pyrrolidin-1-ylprop-1-ynyl)phenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3CC2)C=2C=CC(Cl)=CC=2)=O)=CC=C1C#CCN1CCCC1 DJPGJWARKQIVBZ-UHFFFAOYSA-N 0.000 claims description 4
• PVTXJGJDOHYFOX-UHFFFAOYSA-N 2h-1,4-benzoxazine Chemical compound C1=CC=C2N=CCOC2=C1 PVTXJGJDOHYFOX-UHFFFAOYSA-N 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 229910052698 phosphorus Inorganic materials 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• 238000006467 substitution reaction Methods 0.000 claims description 4
• VOZPLKROXDWMKC-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-(2-piperidin-1-ylethoxy)phenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3CC2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OCCN1CCCCC1 VOZPLKROXDWMKC-UHFFFAOYSA-N 0.000 claims description 3
• ULUKMAISDFJGGU-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]-[1,3]thiazolo[5,4-c]pyridin-4-one;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.COC1=CC(N2C(C=3SC(=NC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OCCN1CCCC1 ULUKMAISDFJGGU-UHFFFAOYSA-N 0.000 claims description 3
• UAZFWESTBFIFDL-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-(3-pyrrolidin-1-ylpropyl)phenyl]-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1CCCN1CCCC1 UAZFWESTBFIFDL-UHFFFAOYSA-N 0.000 claims description 3
• WXJFJGWILLCRME-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[4-[2-(diethylamino)ethoxy]-3-methoxyphenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound C1=C(OC)C(OCCN(CC)CC)=CC=C1N1C(=O)C(SC(=N2)C=3C=CC(Cl)=CC=3)=C2CC1 WXJFJGWILLCRME-UHFFFAOYSA-N 0.000 claims description 3
• ZUJHMOJGLZQVRS-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[4-[2-[cyclohexyl(methyl)amino]ethoxy]-3-methoxyphenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3CC2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OCCN(C)C1CCCCC1 ZUJHMOJGLZQVRS-UHFFFAOYSA-N 0.000 claims description 3
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
• DYJPHFUMUVBJBW-UHFFFAOYSA-N 5-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]-2-[4-(trifluoromethyl)phenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3CC2)C=2C=CC(=CC=2)C(F)(F)F)=O)=CC=C1OCCN1CCCC1 DYJPHFUMUVBJBW-UHFFFAOYSA-N 0.000 claims description 3
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
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• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 3
• 125000002971 oxazolyl group Chemical group 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• OLTKJRQUTDMQEN-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3CC2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OCCN1CCCC1 OLTKJRQUTDMQEN-UHFFFAOYSA-N 0.000 claims description 2
• RBHCOCLWURYQEX-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-[2-(2,2,6,6-tetramethylmorpholin-4-yl)ethoxy]phenyl]-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OCCN1CC(C)(C)OC(C)(C)C1 RBHCOCLWURYQEX-UHFFFAOYSA-N 0.000 claims description 2
• ZXNVSFWPFVIAFF-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-[2-(4-piperidin-1-ylpiperidin-1-yl)ethoxy]phenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3CC2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OCCN(CC1)CCC1N1CCCCC1 ZXNVSFWPFVIAFF-UHFFFAOYSA-N 0.000 claims description 2
• NZUCXHZUPVYJHQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-[2-[methyl(propan-2-yl)amino]ethoxy]phenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound C1=C(OCCN(C)C(C)C)C(OC)=CC(N2C(C=3SC(=NC=3CC2)C=2C=CC(Cl)=CC=2)=O)=C1 NZUCXHZUPVYJHQ-UHFFFAOYSA-N 0.000 claims description 2
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
• MPOYBFYHRQBZPM-UHFFFAOYSA-N 3h-pyridin-4-one Chemical compound O=C1CC=NC=C1 MPOYBFYHRQBZPM-UHFFFAOYSA-N 0.000 claims description 2
• ZXIUZISEBUGWLI-UHFFFAOYSA-N 5-[3-methoxy-4-[(3-methylimidazol-4-yl)methoxy]phenyl]-2-[4-(trifluoromethoxy)phenyl]-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3C=C2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=CC=C1OCC1=CN=CN1C ZXIUZISEBUGWLI-UHFFFAOYSA-N 0.000 claims description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 2
• 125000003963 dichloro group Chemical group Cl* 0.000 claims description 2
• 125000002755 pyrazolinyl group Chemical group 0.000 claims description 2
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 6
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• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 2
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• 125000005955 1H-indazolyl group Chemical group 0.000 claims 1
• JNIIIKKUGUGXHU-GOSISDBHSA-N 2-(4-chlorophenyl)-5-[3-methoxy-4-[[(2r)-morpholin-2-yl]methoxy]phenyl]-6,7-dihydro-[1,3]thiazolo[5,4-c]pyridin-4-one Chemical compound COC1=CC(N2C(C=3SC(=NC=3CC2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OC[C@H]1CNCCO1 JNIIIKKUGUGXHU-GOSISDBHSA-N 0.000 claims 1
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• 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 173
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