AU2005316313B2 - Novel MCH receptor antagonists - Google Patents
Novel MCH receptor antagonists Download PDFInfo
- Publication number
- AU2005316313B2 AU2005316313B2 AU2005316313A AU2005316313A AU2005316313B2 AU 2005316313 B2 AU2005316313 B2 AU 2005316313B2 AU 2005316313 A AU2005316313 A AU 2005316313A AU 2005316313 A AU2005316313 A AU 2005316313A AU 2005316313 B2 AU2005316313 B2 AU 2005316313B2
- Authority
- AU
- Australia
- Prior art keywords
- methyl
- amino
- carboxylic acid
- amide
- biphenyl
- Prior art date
- 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
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- 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 title description 4
- 102000006953 melanin-concentrating hormone receptor activity proteins Human genes 0.000 title description 4
- 229940044551 receptor antagonist Drugs 0.000 title description 2
- 239000002464 receptor antagonist Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 267
- 208000008589 Obesity Diseases 0.000 claims abstract description 29
- 235000020824 obesity Nutrition 0.000 claims abstract description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
- 238000011282 treatment Methods 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 201000010099 disease Diseases 0.000 claims abstract description 18
- 239000012453 solvate Substances 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 148
- -1 CI-C 4 alkyl Chemical group 0.000 claims description 90
- 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 78
- LXWNTLBMNCXRQN-UHFFFAOYSA-N 4'-fluoro-1,1'-biphenyl-4-carboxylic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(F)C=C1 LXWNTLBMNCXRQN-UHFFFAOYSA-N 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 150000002431 hydrogen Chemical group 0.000 claims description 22
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- OZFFPJBMCGKDGO-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(Cl)C=C1Cl OZFFPJBMCGKDGO-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- LRGLZMCAACXDKG-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)benzoic acid Chemical compound CC1=CC(Cl)=CC=C1C1=CC=C(C(O)=O)C=C1 LRGLZMCAACXDKG-UHFFFAOYSA-N 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- UDUYQYBNZRZQIZ-UHFFFAOYSA-N 5-(4-fluorophenyl)pyrazine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CN=C1C1=CC=C(F)C=C1 UDUYQYBNZRZQIZ-UHFFFAOYSA-N 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
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- DGHGRAZWNAQANC-UHFFFAOYSA-N 4-(2,4-difluorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(F)C=C1F DGHGRAZWNAQANC-UHFFFAOYSA-N 0.000 claims description 5
- HSVPCRUODVLCAE-UHFFFAOYSA-N 4-(2-chloro-4-methoxyphenyl)benzoic acid Chemical compound ClC1=CC(OC)=CC=C1C1=CC=C(C(O)=O)C=C1 HSVPCRUODVLCAE-UHFFFAOYSA-N 0.000 claims description 5
- PZJQKDATDRPIFT-UHFFFAOYSA-N 4-(2-chloro-4-methylphenyl)benzoic acid Chemical compound ClC1=CC(C)=CC=C1C1=CC=C(C(O)=O)C=C1 PZJQKDATDRPIFT-UHFFFAOYSA-N 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- KTEKPJWBYQYJLW-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(F)C=C1Cl KTEKPJWBYQYJLW-UHFFFAOYSA-N 0.000 claims description 4
- DENUYBFZOWWZMD-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl(pyrrolidin-3-ylmethyl)amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound N=1C2=CC=C(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)C=C2SC=1N(C)CC1CCNC1 DENUYBFZOWWZMD-UHFFFAOYSA-N 0.000 claims description 4
- PFEVGHCXMYFBMG-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl-(1-methylpyrrolidin-3-yl)amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound N=1C2=CC=C(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)C=C2SC=1N(C)C1CCN(C)C1 PFEVGHCXMYFBMG-UHFFFAOYSA-N 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 125000005750 substituted cyclic group Chemical group 0.000 claims description 4
- VPVLGKHWGDSWOS-UHFFFAOYSA-N 4-(2-chloro-4-methoxyphenyl)-n-[2-[methyl-(1-methylpyrrolidin-3-yl)amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound ClC1=CC(OC)=CC=C1C1=CC=C(C(=O)NC=2C=C3SC(=NC3=CC=2)N(C)C2CN(C)CC2)C=C1 VPVLGKHWGDSWOS-UHFFFAOYSA-N 0.000 claims description 3
- AOTYKBXXCYCXRZ-UHFFFAOYSA-N 4-(2-chlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1Cl AOTYKBXXCYCXRZ-UHFFFAOYSA-N 0.000 claims description 3
- YOUDKBGMWRQAIS-UHFFFAOYSA-N 4-[2-chloro-4-(trifluoromethyl)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(F)(F)F)C=C1Cl YOUDKBGMWRQAIS-UHFFFAOYSA-N 0.000 claims description 3
- PHEPUGXCVVHZGS-UHFFFAOYSA-N 5-(3-chlorophenyl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=CC(Cl)=C1 PHEPUGXCVVHZGS-UHFFFAOYSA-N 0.000 claims description 3
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 3
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000005518 carboxamido group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 201000001421 hyperglycemia Diseases 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- STLGUJTWUAPIIL-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC(Cl)=C1Cl STLGUJTWUAPIIL-UHFFFAOYSA-N 0.000 claims description 2
- OFOKUKWYWDEYOG-UHFFFAOYSA-N 4-(4-fluoro-2-methylphenyl)benzoic acid Chemical compound CC1=CC(F)=CC=C1C1=CC=C(C(O)=O)C=C1 OFOKUKWYWDEYOG-UHFFFAOYSA-N 0.000 claims description 2
- IZDIJERBVRWNHB-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound N=1C2=CC=C(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)C=C2SC=1N(C)C1CCN(C)CC1 IZDIJERBVRWNHB-UHFFFAOYSA-N 0.000 claims description 2
- MYCAHXOIIAWKMI-UHFFFAOYSA-N 5-(3,4-difluorophenyl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(F)C(F)=C1 MYCAHXOIIAWKMI-UHFFFAOYSA-N 0.000 claims description 2
- YOFXYDVYMHOXSY-UHFFFAOYSA-N 5-(4-fluorophenyl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(F)C=C1 YOFXYDVYMHOXSY-UHFFFAOYSA-N 0.000 claims description 2
- CGCBAGCSAKDINT-UHFFFAOYSA-N 5-(5-chlorothiophen-2-yl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]thiophene-2-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3SC(=CC=3)C=3SC(Cl)=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 CGCBAGCSAKDINT-UHFFFAOYSA-N 0.000 claims description 2
- QGMFBCDNJUZQBZ-UHFFFAOYSA-N 5-phenylthiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=CC=C1 QGMFBCDNJUZQBZ-UHFFFAOYSA-N 0.000 claims description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 2
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- 208000008279 Dumping Syndrome Diseases 0.000 claims description 2
- 208000007882 Gastritis Diseases 0.000 claims description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 2
- 208000010412 Glaucoma Diseases 0.000 claims description 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
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- 208000007920 Neurogenic Inflammation Diseases 0.000 claims description 2
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- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 claims description 2
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- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
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- MJCKIPNEXQMFHC-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-4-(4-fluorophenyl)benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(F)C=C1 MJCKIPNEXQMFHC-UHFFFAOYSA-N 0.000 claims description 2
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- NJHKQNLAMYYREO-UHFFFAOYSA-N n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]-5-thiophen-3-ylthiophene-2-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3SC(=CC=3)C3=CSC=C3)=CC=C2OC=1N(C)C1CCN(C)CC1 NJHKQNLAMYYREO-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 3
- GWRSATNRNFYMDI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound FC=1C=C(NC=2N=C3N(C4CCCC4)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCN(C)CC1 GWRSATNRNFYMDI-UHFFFAOYSA-N 0.000 claims 2
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- LPQZERIRKRYGGM-UHFFFAOYSA-N tert-butyl pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1 LPQZERIRKRYGGM-UHFFFAOYSA-N 0.000 description 1
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- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 description 1
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Classifications
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Diabetes (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63711604P | 2004-12-17 | 2004-12-17 | |
| US60/637,116 | 2004-12-17 | ||
| PCT/US2005/045864 WO2006066173A2 (en) | 2004-12-17 | 2005-12-16 | Novel mch receptor antagonists |
Publications (2)
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| AU2005316313A1 AU2005316313A1 (en) | 2006-06-22 |
| AU2005316313B2 true AU2005316313B2 (en) | 2011-09-29 |
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| AU2005316313A Ceased AU2005316313B2 (en) | 2004-12-17 | 2005-12-16 | Novel MCH receptor antagonists |
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| EP (1) | EP1828177B1 (https=) |
| JP (1) | JP4988591B2 (https=) |
| CN (1) | CN101072775A (https=) |
| AT (1) | ATE404555T1 (https=) |
| AU (1) | AU2005316313B2 (https=) |
| BR (1) | BRPI0517425A (https=) |
| CA (1) | CA2589678A1 (https=) |
| DE (1) | DE602005009021D1 (https=) |
| DK (1) | DK1828177T3 (https=) |
| ES (1) | ES2312048T3 (https=) |
| MX (1) | MX2007007226A (https=) |
| PL (1) | PL1828177T3 (https=) |
| PT (1) | PT1828177E (https=) |
| SI (1) | SI1828177T1 (https=) |
| WO (1) | WO2006066173A2 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2006038680A1 (ja) | 2004-10-01 | 2006-04-13 | Banyu Pharmaceutical Co.,Ltd | ２－アリールカルボキサミド－含窒素複素環化合物 |
| WO2006066174A1 (en) * | 2004-12-17 | 2006-06-22 | Eli Lilly And Company | Thiazolopyridinone derivates as mch receptor antagonists |
| PL1848435T3 (pl) | 2005-01-25 | 2016-08-31 | Synta Pharmaceuticals Corp | Związki przeciwko zapaleniom i zastosowania związane z odpornością |
| US8153813B2 (en) * | 2007-12-20 | 2012-04-10 | Abbott Laboratories | Benzothiazole and benzooxazole derivatives and methods of use |
| CA2725481A1 (en) | 2008-06-18 | 2009-12-23 | Pfizer Limited | Nicotinamide derivatives |
| WO2010010435A2 (en) * | 2008-07-22 | 2010-01-28 | Glenmark Pharmaceutical S.A. | Fused oxazole and thiazole derivatives as trpms modulators |
| SA110310332B1 (ar) | 2009-05-01 | 2013-12-10 | Astrazeneca Ab | مركبات ميثانون (3 استبدال -ازيتيدين -1-يل )(5- فينيل -1، 3، 4- أوكساديازول -2-يل ) |
| AU2011275547B2 (en) | 2010-07-06 | 2015-10-29 | Astrazeneca Ab | Therapeutic agents 976 |
| JP5996532B2 (ja) * | 2010-07-15 | 2016-09-21 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 有害生物防除剤としての新規複素環式化合物 |
| TW201305152A (zh) * | 2010-12-14 | 2013-02-01 | Shionogi & Co | 具有血管內皮脂肪酶抑制活性之苯并噻唑及吖苯并噻唑衍生物 |
| UY34194A (es) | 2011-07-15 | 2013-02-28 | Astrazeneca Ab | ?(3-(4-(espiroheterocíclico)metil)fenoxi)azetidin-1-il)(5-(fenil)-1,3,4-oxadiazol-2-il)metanona en el tratamiento de la obesidad? |
| JO3225B1 (ar) * | 2012-11-27 | 2018-03-08 | Lilly Co Eli | 6-((s)-1-{1-[5-(2-هيدروكسي-إيثوكسي)-بيريدين-2-يل]-1h-بيرازول-3-يل}إيثيل)-3h-1 ، 3-بنزو ثيازول-2- أون باعتباره مضاد مستقبل ampa يعتمد على tarp- جاما 8 |
| LT3466955T (lt) | 2014-01-13 | 2021-02-25 | Aurigene Discovery Technologies Limited | Oksazol[4,5-b]piridino ir tiazol[4,5-b]piridino darinių, kaip irak4 inhibitorių, skirtų vėžio gydymui, gamybos būdas |
| JP6802194B2 (ja) | 2015-06-22 | 2020-12-16 | アクテリオン ファーマシューティカルズ リミテッドＡｃｔｅｌｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | Ｎａｄｐｈオキシダーゼ４阻害剤 |
| CN108024971A (zh) * | 2015-07-15 | 2018-05-11 | 奥列基因发现技术有限公司 | 作为irak-4抑制剂的取代的氮杂化合物 |
| EP3600270B1 (en) * | 2017-03-31 | 2023-06-14 | Aurigene Oncology Limited | Compounds and compositions for treating hematological disorders |
| HUE067356T2 (hu) | 2017-10-31 | 2024-10-28 | Curis Inc | IRAK4 inhibitor és BCL-2 inhibitor kombinációban, rák kezelésére való felhasználásra |
| CN109485620A (zh) * | 2018-12-26 | 2019-03-19 | 安徽工大化工科技有限公司 | 一种2-甲氧基-6-甲氧基苯并噻唑的制备方法 |
| JP2022532718A (ja) * | 2019-05-14 | 2022-07-19 | メタボメッド リミテッド | Ａｃｓｓ２阻害剤およびその使用方法 |
| EP4319750A4 (en) | 2021-04-08 | 2025-02-26 | Curis, Inc. | COMBINATION THERAPIES FOR THE TREATMENT OF CANCER |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2565595A (en) | 1994-05-28 | 1995-12-21 | Smithkline Beecham Plc | Amide derivatives having 5ht1d-antagonist activity |
| ES2300119T3 (es) | 1997-02-27 | 2008-06-01 | Takeda Pharmaceutical Company Limited | Compuestos de amina, su produccion y su uso como inhibidores de la produccion de beta-amiloide. |
| EP1218336A2 (en) | 1999-09-20 | 2002-07-03 | Takeda Chemical Industries, Ltd. | Melanin concentrating hormone antagonist |
| KR20020084116A (ko) | 2000-02-07 | 2002-11-04 | 애보트 게엠베하 운트 콤파니 카게 | 2-벤조티아졸릴 우레아 유도체 및 이의 단백질 키나제억제제로서의 용도 |
| EP1285651B1 (en) * | 2000-04-28 | 2010-09-01 | Takeda Pharmaceutical Company Limited | Melanin concentrating hormone antagonists |
| US7229986B2 (en) * | 2000-05-16 | 2007-06-12 | Takeda Pharmaceutical Company Ltd. | Melanin-concentrating hormone antagonist |
| EP1332131A2 (en) * | 2000-11-07 | 2003-08-06 | Bristol-Myers Squibb Company | Acid derivatives useful as serine protease inhibitors |
| DE10139126A1 (de) * | 2001-08-09 | 2003-02-20 | Ciba Sc Pfersee Gmbh | Zusammensetzungen aus Polysiloxanen, Fluorpolymeren und Extendern |
| DE10139416A1 (de) * | 2001-08-17 | 2003-03-06 | Aventis Pharma Gmbh | Aminoalkyl substituierte aromatische Bicyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| JP2005518371A (ja) * | 2001-12-10 | 2005-06-23 | アムジエン・インコーポレーテツド | バニロイド受容体リガンド及び治療に於けるこれらの使用 |
| JP4595542B2 (ja) * | 2002-07-30 | 2010-12-08 | 萬有製薬株式会社 | ベンズイミダゾール誘導体を有効成分とするメラニン凝集ホルモン受容体拮抗剤 |
| AU2003296405A1 (en) | 2003-01-06 | 2004-08-10 | Eli Lilly And Company | Fused heterocyclic derivatives as ppar modulators |
| WO2006094682A1 (en) * | 2005-03-09 | 2006-09-14 | F. Hoffmann-La Roche Ag | Benzothiazole, thiazolopyridine, benzooxazole and oxazolopyridine derivatives as antidiabetic compounds |
-
2005
- 2005-12-16 DE DE602005009021T patent/DE602005009021D1/de not_active Expired - Lifetime
- 2005-12-16 WO PCT/US2005/045864 patent/WO2006066173A2/en not_active Ceased
- 2005-12-16 EP EP05854552A patent/EP1828177B1/en not_active Expired - Lifetime
- 2005-12-16 US US11/719,576 patent/US7838543B2/en not_active Expired - Fee Related
- 2005-12-16 MX MX2007007226A patent/MX2007007226A/es active IP Right Grant
- 2005-12-16 JP JP2007546990A patent/JP4988591B2/ja not_active Expired - Fee Related
- 2005-12-16 AU AU2005316313A patent/AU2005316313B2/en not_active Ceased
- 2005-12-16 CN CNA2005800418488A patent/CN101072775A/zh active Pending
- 2005-12-16 AT AT05854552T patent/ATE404555T1/de active
- 2005-12-16 BR BRPI0517425-2A patent/BRPI0517425A/pt not_active IP Right Cessation
- 2005-12-16 PT PT05854552T patent/PT1828177E/pt unknown
- 2005-12-16 ES ES05854552T patent/ES2312048T3/es not_active Expired - Lifetime
- 2005-12-16 SI SI200530456T patent/SI1828177T1/sl unknown
- 2005-12-16 DK DK05854552T patent/DK1828177T3/da active
- 2005-12-16 PL PL05854552T patent/PL1828177T3/pl unknown
- 2005-12-16 CA CA002589678A patent/CA2589678A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| PT1828177E (pt) | 2008-10-28 |
| US7838543B2 (en) | 2010-11-23 |
| CN101072775A (zh) | 2007-11-14 |
| BRPI0517425A (pt) | 2008-10-07 |
| EP1828177B1 (en) | 2008-08-13 |
| PL1828177T3 (pl) | 2009-01-30 |
| WO2006066173A3 (en) | 2006-07-27 |
| EP1828177A2 (en) | 2007-09-05 |
| WO2006066173A2 (en) | 2006-06-22 |
| DK1828177T3 (da) | 2008-11-17 |
| US20090170913A1 (en) | 2009-07-02 |
| AU2005316313A1 (en) | 2006-06-22 |
| JP2008524249A (ja) | 2008-07-10 |
| SI1828177T1 (sl) | 2009-02-28 |
| MX2007007226A (es) | 2007-08-21 |
| DE602005009021D1 (de) | 2008-09-25 |
| CA2589678A1 (en) | 2006-06-22 |
| JP4988591B2 (ja) | 2012-08-01 |
| ES2312048T3 (es) | 2009-02-16 |
| ATE404555T1 (de) | 2008-08-15 |
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