CA2463509A1 - Lactam derivatives as antagonists for human 11cby receptors - Google Patents
Lactam derivatives as antagonists for human 11cby receptors Download PDFInfo
- Publication number
- CA2463509A1 CA2463509A1 CA002463509A CA2463509A CA2463509A1 CA 2463509 A1 CA2463509 A1 CA 2463509A1 CA 002463509 A CA002463509 A CA 002463509A CA 2463509 A CA2463509 A CA 2463509A CA 2463509 A1 CA2463509 A1 CA 2463509A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- group
- phenyl
- methoxy
- 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.)
- Abandoned
Links
- 239000005557 antagonist Substances 0.000 title description 9
- 150000003951 lactams Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 249
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 239000012453 solvate Substances 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims description 71
- -1 C1-2alkyl Chemical group 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 38
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 23
- 150000001412 amines Chemical class 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 16
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 15
- 101800002739 Melanin-concentrating hormone Proteins 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 239000002585 base Substances 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 11
- 125000002619 bicyclic group Chemical group 0.000 claims description 10
- 150000008064 anhydrides Chemical class 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 208000008589 Obesity Diseases 0.000 claims description 7
- 239000000010 aprotic solvent Substances 0.000 claims description 7
- 235000020824 obesity Nutrition 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical group OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 4
- YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- IVRCHBYBKXRNIC-UHFFFAOYSA-N 3-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]-6-phenylthieno[3,2-d]pyrimidin-4-one Chemical compound COC1=CC(N2C(C=3SC(=CC=3N=C2)C=2C=CC=CC=2)=O)=CC=C1OCCN1CCCC1 IVRCHBYBKXRNIC-UHFFFAOYSA-N 0.000 claims description 3
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims description 3
- 239000007868 Raney catalyst Substances 0.000 claims description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 3
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 238000006073 displacement reaction Methods 0.000 claims description 3
- 150000003949 imides Chemical class 0.000 claims description 3
- 208000024714 major depressive disease Diseases 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 claims description 2
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 claims description 2
- SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 claims description 2
- PZMKGWRBZNOIPQ-UHFFFAOYSA-N 1h-thieno[3,2-d]pyrimidin-4-one Chemical compound OC1=NC=NC2=C1SC=C2 PZMKGWRBZNOIPQ-UHFFFAOYSA-N 0.000 claims description 2
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical group O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 claims description 2
- OSEVYTJMMHAQGG-UHFFFAOYSA-N 2-methylsulfanyl-1h-thieno[3,2-d]pyrimidin-4-one Chemical compound N1C(SC)=NC(=O)C2=C1C=CS2 OSEVYTJMMHAQGG-UHFFFAOYSA-N 0.000 claims description 2
- QJDUIALZROAHNX-UHFFFAOYSA-N 3-[3-methoxy-4-(2-pyrrolidin-1-ylethyl)phenyl]-7-phenyl-1,2,3-benzotriazin-4-one Chemical compound COC1=CC(N2C(C3=CC=C(C=C3N=N2)C=2C=CC=CC=2)=O)=CC=C1CCN1CCCC1 QJDUIALZROAHNX-UHFFFAOYSA-N 0.000 claims description 2
- JEDVKUHCDPPWNR-UHFFFAOYSA-N 3h-thieno[2,3-d]pyrimidin-4-one Chemical compound O=C1NC=NC2=C1C=CS2 JEDVKUHCDPPWNR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- 206010051161 Hyperglucagonaemia Diseases 0.000 claims description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 150000001543 aryl boronic acids Chemical class 0.000 claims description 2
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 230000035880 hyperglucagonemia Effects 0.000 claims description 2
- 201000001421 hyperglycemia Diseases 0.000 claims description 2
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 208000019116 sleep disease Diseases 0.000 claims description 2
- 229940124597 therapeutic agent Drugs 0.000 claims description 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000962 organic group Chemical group 0.000 claims 1
- 239000003586 protic polar solvent Substances 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 149
- 239000000203 mixture Substances 0.000 description 103
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 62
- 239000000243 solution Substances 0.000 description 54
- 238000005481 NMR spectroscopy Methods 0.000 description 52
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 14
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 14
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
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- 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 description 10
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- PZYPNBPKQPUEMB-UHFFFAOYSA-N 5-bromo-2-[4-[2-[di(propan-2-yl)amino]ethoxy]-3-methoxyphenyl]isoindole-1,3-dione Chemical compound C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC(N2C(C3=CC(Br)=CC=C3C2=O)=O)=C1 PZYPNBPKQPUEMB-UHFFFAOYSA-N 0.000 description 7
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- HYTACLVSJIFYBY-UHFFFAOYSA-N azane;dichloromethane;methanol Chemical compound N.OC.ClCCl HYTACLVSJIFYBY-UHFFFAOYSA-N 0.000 description 7
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/91—Oxygen atoms with aryl or aralkyl radicals attached in position 2 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/10—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D257/12—Six-membered rings having four nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
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- General Health & Medical Sciences (AREA)
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- Engineering & Computer Science (AREA)
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- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Peptides Or Proteins (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Indole Compounds (AREA)
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- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0124627.1 | 2001-10-15 | ||
| GBGB0124627.1A GB0124627D0 (en) | 2001-10-15 | 2001-10-15 | Novel compounds |
| PCT/US2002/032740 WO2003033480A1 (en) | 2001-10-15 | 2002-10-15 | Lactam derivatives as antagonists for human 11cby receptors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2463509A1 true CA2463509A1 (en) | 2003-04-24 |
Family
ID=9923785
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002463509A Abandoned CA2463509A1 (en) | 2001-10-15 | 2002-10-15 | Lactam derivatives as antagonists for human 11cby receptors |
| CA002463508A Abandoned CA2463508A1 (en) | 2001-10-15 | 2002-10-15 | Pyrimidinones as melanin concentrating hormone receptor 1 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002463508A Abandoned CA2463508A1 (en) | 2001-10-15 | 2002-10-15 | Pyrimidinones as melanin concentrating hormone receptor 1 |
Country Status (21)
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| US7084156B2 (en) | 2001-11-27 | 2006-08-01 | Merck & Co., Inc. | 2-Aminoquinoline compounds |
| DE10238865A1 (de) * | 2002-08-24 | 2004-03-11 | Boehringer Ingelheim International Gmbh | Neue Carbonsäureamid-Verbindungen mit MCH-antagonistischer Wirkung, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| US7351719B2 (en) | 2002-10-31 | 2008-04-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Amide compounds having MCH-antagonistic activity and medicaments comprising these compounds |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| WO2004092181A1 (en) * | 2003-04-11 | 2004-10-28 | Smithkline Beecham Corporation | Heterocyclic mchr1 antagonists |
| WO2005016928A1 (ja) * | 2003-08-15 | 2005-02-24 | Banyu Pharmaceutical Co., Ltd. | イミダゾピリジン誘導体 |
| KR100747042B1 (ko) * | 2003-08-19 | 2007-08-07 | 솔젠트 (주) | 신물질６-메틸-３-펜에틸-３,４-디히드로-１ｈ-큐나졸린-２-티온,이의 제조방법 및 이를 유효성분으로 포함하는 미백 효능조성물 |
| CA2543122A1 (en) * | 2003-10-23 | 2005-05-12 | Glaxo Group Limited | 3-(4-aminophenyl) thienopyrimid-4-one derivatives as mch r1 antagonists for the treatment of obesity, diabetes, depression and anxiety |
| US7592373B2 (en) | 2003-12-23 | 2009-09-22 | Boehringer Ingelheim International Gmbh | Amide compounds with MCH antagonistic activity and medicaments comprising these compounds |
| UA83416C2 (en) | 2004-02-13 | 2008-07-10 | Баниу Фармасьютикал Ко., Лтд. | Fused ring 4-oxopyrimidine derivative |
| DE102004010893A1 (de) * | 2004-03-06 | 2005-09-22 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue ß-Ketoamid-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| US7605176B2 (en) | 2004-03-06 | 2009-10-20 | Boehringer Ingelheim International Gmbh | β-ketoamide compounds with MCH antagonistic activity |
| EP1734963A4 (en) | 2004-04-02 | 2008-06-18 | Merck & Co Inc | METHOD FOR TREATING PEOPLE WITH METABOLIC AND ANTHROPOMETRIC DISORDER |
| DE102004017934A1 (de) | 2004-04-14 | 2005-11-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| US7524862B2 (en) | 2004-04-14 | 2009-04-28 | Boehringer Ingelheim International Gmbh | Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds |
| MX2007007227A (es) | 2004-12-17 | 2007-08-21 | Lilly Co Eli | Derivados de tiazolopiridinona como antagonistas del receptor mch. |
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| WO2006118320A1 (ja) | 2005-04-28 | 2006-11-09 | Takeda Pharmaceutical Company Limited | チエノピリミドン化合物 |
| WO2007011286A1 (en) * | 2005-07-15 | 2007-01-25 | Astrazeneca Ab | Therapeutic agents |
| KR20080042158A (ko) * | 2005-08-31 | 2008-05-14 | 셀진 코포레이션 | 이소인돌-이미드 화합물과 이를 포함하는 조성물 및 이를이용한 방법 |
| BRPI0617436B8 (pt) * | 2005-10-19 | 2021-05-25 | Kissei Pharmaceutical | derivado heterocíclico fundido, composição farmacêutica compreendendo o mesmo e usos do dito derivado na prevenção ou tratamento de doença dependente de hormônio sexual e na regulação da reprodução, contracepção ou indução de ovulação |
| US7745447B2 (en) | 2005-10-26 | 2010-06-29 | Bristol-Myers Squibb Company | Substituted thieno[3,2-D]pyrimidines as non-basic melanin concentrating hormone receptor-1 antagonists |
| US8618115B2 (en) | 2005-10-26 | 2013-12-31 | Bristol-Myers Squibb Company | Substituted thieno[3,2-d]pyrimidinones as MCHR1 antagonists and methods for using them |
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| US7553836B2 (en) | 2006-02-06 | 2009-06-30 | Bristol-Myers Squibb Company | Melanin concentrating hormone receptor-1 antagonists |
| RU2008136898A (ru) | 2006-02-15 | 2010-03-20 | Санофи-Авентис (Fr) | Азациклил-замещенные арилдигидроизохинолиноны, способ их получения и их применение в качестве лекарственных средств |
| JP2009526794A (ja) | 2006-02-15 | 2009-07-23 | サノフィ−アベンティス | 新規なアミノアルコール置換アリールチエノピリミジノン、それらの製造方法及び薬剤としてそれらの使用 |
| JP2009526795A (ja) | 2006-02-15 | 2009-07-23 | サノフィ−アベンティス | 新規なアミノアルコール置換アリールジヒドロイソキノリノン、それらの製造方法及び薬剤としてそれらの使用 |
| WO2007093363A1 (en) | 2006-02-15 | 2007-08-23 | Sanofi-Aventis | Novel azacycly-substituted arylthienopyrimidinones, process for their preparation and their use as medicaments |
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| JP5269804B2 (ja) * | 2006-12-14 | 2013-08-21 | イーライ リリー アンド カンパニー | 新規なｍｃｈ受容体拮抗薬 |
| BRPI0806537A2 (pt) | 2007-01-10 | 2014-04-22 | Albany Molecular Res Inc | Indazóis substituídos por 5-piridinona |
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| DE102007028925A1 (de) | 2007-06-22 | 2008-12-24 | Saltigo Gmbh | Verfahren zur Herstellung von 2-Phenoxyacetalen und den daraus korrespondierenden 2-Phenoxycarbaldehyden |
| ATE544759T1 (de) | 2007-07-21 | 2012-02-15 | Albany Molecular Res Inc | 5-pyridinon-substituierte indazole und pharmazeutische zusammensetzungen davon |
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| US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL137227B2 (en) * | 1984-03-28 | 1986-05-31 | Univ Lodzki | Process for preparing novel n-/dialkylaminoalkoxyphenyl/-imides of tetrahydrophtalic acids |
| DE69723869T2 (de) * | 1996-12-31 | 2004-04-22 | Dr. Reddy's Laboratories Ltd. | Heterozyklische verbindungen, verfahren zu ihrer herstellung, pharmazeutische zusammensetzungen die diese enthalten und ihre anwendung in der behandlung von diabetis und verwandten krankheiten |
| CA2386474A1 (en) * | 1999-09-20 | 2001-03-29 | Takeda Chemical Industries, Ltd. | Melanin concentrating hormone antagonist |
-
2001
- 2001-10-15 GB GBGB0124627.1A patent/GB0124627D0/en not_active Ceased
-
2002
- 2002-10-15 MX MXPA04003534A patent/MXPA04003534A/es unknown
- 2002-10-15 CN CNA028235932A patent/CN1596247A/zh active Pending
- 2002-10-15 MX MXPA04003532A patent/MXPA04003532A/es unknown
- 2002-10-15 CA CA002463509A patent/CA2463509A1/en not_active Abandoned
- 2002-10-15 DE DE60218721T patent/DE60218721T2/de not_active Expired - Fee Related
- 2002-10-15 EP EP02801692A patent/EP1442025B1/en not_active Expired - Lifetime
- 2002-10-15 ES ES02801693T patent/ES2279009T3/es not_active Expired - Lifetime
- 2002-10-15 WO PCT/US2002/032740 patent/WO2003033480A1/en not_active Ceased
- 2002-10-15 EP EP02801693A patent/EP1436267B1/en not_active Expired - Lifetime
- 2002-10-15 PL PL02370138A patent/PL370138A1/xx not_active Application Discontinuation
- 2002-10-15 JP JP2003536220A patent/JP2005508966A/ja active Pending
- 2002-10-15 BR BR0213242-7A patent/BR0213242A/pt not_active Application Discontinuation
- 2002-10-15 NZ NZ531911A patent/NZ531911A/en unknown
- 2002-10-15 KR KR1020047005548A patent/KR20050043724A/ko not_active Withdrawn
- 2002-10-15 HU HU0402346A patent/HUP0402346A2/hu unknown
- 2002-10-15 ES ES02801692T patent/ES2283647T3/es not_active Expired - Lifetime
- 2002-10-15 AT AT02801693T patent/ATE349434T1/de not_active IP Right Cessation
- 2002-10-15 AT AT02801692T patent/ATE356119T1/de not_active IP Right Cessation
- 2002-10-15 IL IL16107402A patent/IL161074A0/xx unknown
- 2002-10-15 CZ CZ2004499A patent/CZ2004499A3/cs unknown
- 2002-10-15 JP JP2003536216A patent/JP2005510487A/ja active Pending
- 2002-10-15 CN CNA028204522A patent/CN1571774A/zh active Pending
- 2002-10-15 BR BR0213040-8A patent/BR0213040A/pt not_active IP Right Cessation
- 2002-10-15 IL IL16087202A patent/IL160872A0/xx unknown
- 2002-10-15 HU HU0402335A patent/HUP0402335A3/hu unknown
- 2002-10-15 KR KR10-2004-7005546A patent/KR20040045833A/ko not_active Withdrawn
- 2002-10-15 CA CA002463508A patent/CA2463508A1/en not_active Abandoned
- 2002-10-15 PL PL02370587A patent/PL370587A1/xx not_active Application Discontinuation
- 2002-10-15 CZ CZ2004498A patent/CZ2004498A3/cs unknown
- 2002-10-15 RU RU2004110053/04A patent/RU2004110053A/ru not_active Application Discontinuation
- 2002-10-15 DE DE60217147T patent/DE60217147T2/de not_active Expired - Fee Related
- 2002-10-15 WO PCT/US2002/032739 patent/WO2003033476A1/en not_active Ceased
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2004
- 2004-04-05 ZA ZA200402672A patent/ZA200402672B/en unknown
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- 2004-04-13 NO NO20041504A patent/NO20041504L/no not_active Application Discontinuation
- 2004-04-13 NO NO20041503A patent/NO20041503L/no not_active Application Discontinuation
- 2004-04-14 CO CO04034243A patent/CO5580778A2/es not_active Application Discontinuation
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