CA2501529A1 - Quinazolinone derivatives useful as anti-hyperalgesic agents - Google Patents
Quinazolinone derivatives useful as anti-hyperalgesic agents Download PDFInfo
- Publication number
- CA2501529A1 CA2501529A1 CA002501529A CA2501529A CA2501529A1 CA 2501529 A1 CA2501529 A1 CA 2501529A1 CA 002501529 A CA002501529 A CA 002501529A CA 2501529 A CA2501529 A CA 2501529A CA 2501529 A1 CA2501529 A1 CA 2501529A1
- Authority
- CA
- Canada
- Prior art keywords
- c6alkyl
- c6alkoxy
- hal
- c6alkoxyc1
- amino
- 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
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 230000003070 anti-hyperalgesia Effects 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims abstract description 9
- 239000003814 drug Substances 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 105
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 8
- 150000003839 salts Chemical group 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000012458 free base Substances 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 230000004913 activation Effects 0.000 claims description 7
- 108010062740 TRPV Cation Channels Proteins 0.000 claims description 6
- 102000011040 TRPV Cation Channels Human genes 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- SWXXKWPYNMZFTE-UHFFFAOYSA-N (c-ethylsulfanylcarbonimidoyl)azanium;bromide Chemical compound Br.CCSC(N)=N SWXXKWPYNMZFTE-UHFFFAOYSA-N 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 17
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 9
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 8
- 101150020251 NR13 gene Proteins 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000002346 iodo group Chemical group I* 0.000 claims 2
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- 241000282414 Homo sapiens Species 0.000 abstract description 7
- 230000003042 antagnostic effect Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
- 239000000203 mixture Substances 0.000 description 32
- 229910052739 hydrogen Inorganic materials 0.000 description 30
- -1 methoxy, ethoxy, n-propoxy Chemical group 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 235000019439 ethyl acetate Nutrition 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- 230000002829 reductive effect Effects 0.000 description 18
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 230000000875 corresponding effect Effects 0.000 description 7
- 210000002683 foot Anatomy 0.000 description 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 208000004454 Hyperalgesia Diseases 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
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- 101000633069 Homo sapiens Transient receptor potential cation channel subfamily V member 1 Proteins 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 150000002367 halogens Chemical group 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- IWRPKTFHMYNBLG-UHFFFAOYSA-N 6-(4-chloro-3-fluorophenyl)-2-methyl-7-propan-2-yl-1h-quinazolin-4-one Chemical compound CC(C)C1=CC=2N=C(C)NC(=O)C=2C=C1C1=CC=C(Cl)C(F)=C1 IWRPKTFHMYNBLG-UHFFFAOYSA-N 0.000 description 4
- JERXWDBVRYWKDD-UHFFFAOYSA-N 6-[4-chloro-3-(cyclopropylmethoxy)phenyl]-2-methyl-7-propan-2-yl-1h-quinazolin-4-one Chemical compound CC(C)C1=CC=2N=C(C)NC(=O)C=2C=C1C(C=1)=CC=C(Cl)C=1OCC1CC1 JERXWDBVRYWKDD-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000012981 Hank's balanced salt solution Substances 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 208000002193 Pain Diseases 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
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- 235000019253 formic acid Nutrition 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- AISFIYCZBJZEGE-UHFFFAOYSA-N methyl 2-amino-5-iodo-4-propan-2-ylbenzoate Chemical compound COC(=O)C1=CC(I)=C(C(C)C)C=C1N AISFIYCZBJZEGE-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- CMJQIHGBUKZEHP-UHFFFAOYSA-N (4-chloro-3-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C(F)=C1 CMJQIHGBUKZEHP-UHFFFAOYSA-N 0.000 description 3
- SKFGRQLMEUDMLM-UHFFFAOYSA-N (4-chloro-3-propoxyphenyl)boronic acid Chemical compound CCCOC1=CC(B(O)O)=CC=C1Cl SKFGRQLMEUDMLM-UHFFFAOYSA-N 0.000 description 3
- ICAKHSWCSZCVGZ-UHFFFAOYSA-N 6-(4-chloro-3-propoxyphenyl)-2-methyl-7-propan-2-yl-1h-quinazolin-4-one Chemical compound C1=C(Cl)C(OCCC)=CC(C=2C(=CC3=C(C(NC(C)=N3)=O)C=2)C(C)C)=C1 ICAKHSWCSZCVGZ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 208000035154 Hyperesthesia Diseases 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- 125000000524 functional group Chemical group 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- CIFBIIKFGFJMBD-UHFFFAOYSA-N methyl 2-amino-4-propan-2-ylbenzoate Chemical compound COC(=O)C1=CC=C(C(C)C)C=C1N CIFBIIKFGFJMBD-UHFFFAOYSA-N 0.000 description 3
- JBXCAIRQKAPCJW-UHFFFAOYSA-N methyl 2-amino-5-(4-chloro-3-fluorophenyl)-4-propan-2-ylbenzoate Chemical compound C1=C(N)C(C(=O)OC)=CC(C=2C=C(F)C(Cl)=CC=2)=C1C(C)C JBXCAIRQKAPCJW-UHFFFAOYSA-N 0.000 description 3
- OKNVKMBANCTYFU-UHFFFAOYSA-N methyl 2-amino-5-(4-chloro-3-propoxyphenyl)-4-propan-2-ylbenzoate Chemical compound C1=C(Cl)C(OCCC)=CC(C=2C(=CC(N)=C(C(=O)OC)C=2)C(C)C)=C1 OKNVKMBANCTYFU-UHFFFAOYSA-N 0.000 description 3
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- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/56—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
-
- 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
- C07D239/90—Oxygen atoms with acyclic 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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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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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
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- Physical Education & Sports Medicine (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0223730.3 | 2002-10-11 | ||
| GBGB0223730.3A GB0223730D0 (en) | 2002-10-11 | 2002-10-11 | Organic compounds |
| PCT/EP2003/011276 WO2004033435A1 (en) | 2002-10-11 | 2003-10-10 | Quinazolinone derivatives useful as anti-hyperalgesic agents |
Publications (1)
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|---|---|
| CA2501529A1 true CA2501529A1 (en) | 2004-04-22 |
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Family Applications (1)
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|---|---|---|---|
| CA002501529A Abandoned CA2501529A1 (en) | 2002-10-11 | 2003-10-10 | Quinazolinone derivatives useful as anti-hyperalgesic agents |
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| EP (1) | EP1554257A1 (enExample) |
| JP (1) | JP4571863B2 (enExample) |
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| BR (1) | BR0314557A (enExample) |
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| GB (1) | GB0223730D0 (enExample) |
| PE (1) | PE20040736A1 (enExample) |
| TW (1) | TW200410695A (enExample) |
| WO (1) | WO2004033435A1 (enExample) |
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| GB0412769D0 (en) * | 2004-06-08 | 2004-07-07 | Novartis Ag | Organic compounds |
| US20070054916A1 (en) * | 2004-10-01 | 2007-03-08 | Amgen Inc. | Aryl nitrogen-containing bicyclic compounds and methods of use |
| KR20060087386A (ko) | 2005-01-28 | 2006-08-02 | 주식회사 대웅제약 | 신규 벤조이미다졸 유도체 및 이를 함유하는 약제학적조성물 |
| GB0507298D0 (en) | 2005-04-11 | 2005-05-18 | Novartis Ag | Organic compounds |
| GB0525068D0 (en) * | 2005-12-08 | 2006-01-18 | Novartis Ag | Organic compounds |
| GB0525069D0 (en) * | 2005-12-08 | 2006-01-18 | Novartis Ag | Organic compounds |
| CA2660957C (en) | 2006-08-23 | 2016-10-11 | Neurogen Corporation | 2-phenoxy pyrimidinone analogues |
| EP2079739A2 (en) * | 2006-10-04 | 2009-07-22 | Pfizer Products Inc. | Pyrido[4,3-d]pyrimidin-4(3h)-one derivatives as calcium receptor antagonists |
| JP5372138B2 (ja) | 2008-04-18 | 2013-12-18 | テウン ファーマシューティカル カンパニー,リミテッド | 新規ベンゾオキサジンベンズイミダゾール誘導体、これを含む薬学組成物およびこの用途 |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| JP2013518085A (ja) | 2010-02-01 | 2013-05-20 | ノバルティス アーゲー | CRF−1受容体アンタゴニストとしてのピラゾロ[5,1b]オキサゾール誘導体 |
| AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
| JP5748777B2 (ja) | 2010-02-02 | 2015-07-15 | ノバルティス アーゲー | Crf受容体アンタゴニストとしてのシクロヘキシルアミド誘導体 |
| EP2588197B1 (en) * | 2010-07-02 | 2014-11-05 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
| KR101293384B1 (ko) | 2010-10-13 | 2013-08-05 | 주식회사 대웅제약 | 신규 피리딜 벤조옥사진 유도체, 이를 포함하는 약학 조성물 및 이의 용도 |
| KR20140033377A (ko) | 2011-05-10 | 2014-03-18 | 길리애드 사이언시즈, 인코포레이티드 | 나트륨 채널 조절제로서의 융합된 헤테로시클릭 화합물 |
| UY34094A (es) | 2011-05-27 | 2013-01-03 | Novartis Ag | Derivados de la piperidina 3-espirocíclica como agonistas de receptores de la ghrelina |
| NO3175985T3 (enExample) | 2011-07-01 | 2018-04-28 | ||
| UY34171A (es) | 2011-07-01 | 2013-01-31 | Gilead Sciences Inc | Compuestos heterocíclicos fusionados como moduladores del canal iónico |
| CA2867043A1 (en) | 2012-05-03 | 2013-11-07 | Novartis Ag | L-malate salt of 2,7-diaza-spiro[4.5]dec-7-yle derivatives and crystalline forms thereof as ghrelin receptor agonists |
| US9884841B2 (en) | 2015-04-20 | 2018-02-06 | The Regents Of The University Of Michigan | Small molecule inhibitors of Mcl-1 and uses thereof |
| DE102022104759A1 (de) | 2022-02-28 | 2023-08-31 | SCi Kontor GmbH | Co-Kristall-Screening Verfahren, insbesondere zur Herstellung von Co-Kristallen |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE793737A (fr) * | 1972-01-06 | 1973-07-05 | Alkaline Batteries Ltd | Fermeture de trou de remplissage pour elements d'accumulateurs electriques |
| DE3041678A1 (de) * | 1979-11-15 | 1981-05-27 | Sandoz-Patent-GmbH, 7850 Lörrach | Ein 1-isopropyl-4-phenyl-2(1h)-chinazolinonderivat, dessen herstellung und verwendung |
| JPS56113769A (en) * | 1980-02-13 | 1981-09-07 | Sumitomo Chem Co Ltd | Novel 2 1h -quinazolinone derivative and its preparation |
| JPS5711970A (en) * | 1980-06-24 | 1982-01-21 | Tanabe Seiyaku Co Ltd | Quinazolinone compound and its preparation |
| JPS5714588A (en) * | 1980-07-02 | 1982-01-25 | Kanto Ishi Pharma Co Ltd | 1- tetrahydro-4-pyridyl -2-substituted-quinazolin-4-one derivative and its preparation |
| JPS57149277A (en) * | 1981-03-10 | 1982-09-14 | Taiho Yakuhin Kogyo Kk | Heterocyclic compound |
| DD206995A1 (de) * | 1982-01-20 | 1984-02-15 | Akad Wissenschaften Ddr | Verfahren zur herstellung von 9h-tetrazolo(5,1-b)chinazolin-9-onen |
| CS247557B1 (en) * | 1984-04-06 | 1987-01-15 | Ludmila Fisnerova | Esters of 3-(2-hydroxyethyl)-4(3h)-quinazolinone |
| US5290780A (en) * | 1991-01-30 | 1994-03-01 | American Cyanamid Co. | Angiotensin II receptor blocking 2,3,6 substituted quinazolinones |
| US5284853A (en) * | 1993-04-23 | 1994-02-08 | American Cyanamid Company | Angiotensin II receptor blocking 2,3,6 substituted quinazolinones |
| US5294617A (en) * | 1993-04-23 | 1994-03-15 | American Cyanamid Company | Angiotensin II receptor blocking 2,3,6 substituted quinazolinones |
| EP0635263A3 (en) * | 1993-06-28 | 1995-09-27 | American Cyanamid Co | Angiotensin II antagonists (AII) as inhibitors of the growth of adipose tissue. |
| EP0760819B1 (en) * | 1994-05-24 | 2000-07-19 | F. Hoffmann-La Roche Ag | Tricyclic dicarbonyl derivatives |
| US5783577A (en) * | 1995-09-15 | 1998-07-21 | Trega Biosciences, Inc. | Synthesis of quinazolinone libraries and derivatives thereof |
| US5739330A (en) * | 1996-02-05 | 1998-04-14 | Hoechst Celanese Corporation | Process for preparing quinazolones |
| WO1997044041A1 (en) * | 1996-05-20 | 1997-11-27 | Merck & Co., Inc. | Antagonists of gonadotropin releasing hormone |
| WO1998018781A2 (en) * | 1996-10-28 | 1998-05-07 | Versicor, Inc. | Fused 2,4-pyrimidinedione combinatorial libraries, their preparation and the use of fused 2,4-pyrimidinediones derivatives as antimicrobial agents |
| AU4742101A (en) * | 2000-03-17 | 2001-10-03 | Merck & Co., Inc. | Antagonists of gonadotropin releasing hormone |
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2002
- 2002-10-11 GB GBGB0223730.3A patent/GB0223730D0/en not_active Ceased
-
2003
- 2003-10-06 TW TW092127685A patent/TW200410695A/zh unknown
- 2003-10-09 PE PE2003001026A patent/PE20040736A1/es not_active Application Discontinuation
- 2003-10-09 AR ARP030103674A patent/AR041563A1/es unknown
- 2003-10-10 EP EP03757959A patent/EP1554257A1/en not_active Withdrawn
- 2003-10-10 WO PCT/EP2003/011276 patent/WO2004033435A1/en not_active Ceased
- 2003-10-10 CA CA002501529A patent/CA2501529A1/en not_active Abandoned
- 2003-10-10 BR BR0314557-3A patent/BR0314557A/pt not_active IP Right Cessation
- 2003-10-10 JP JP2004542493A patent/JP4571863B2/ja not_active Expired - Fee Related
- 2003-10-10 AU AU2003273989A patent/AU2003273989A1/en not_active Abandoned
- 2003-10-10 US US10/530,897 patent/US20060154942A1/en not_active Abandoned
- 2003-10-10 CN CNB2003801029327A patent/CN100432059C/zh not_active Expired - Fee Related
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2007
- 2007-12-04 US US11/950,079 patent/US20080293939A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003273989A1 (en) | 2004-05-04 |
| JP2006503875A (ja) | 2006-02-02 |
| CN100432059C (zh) | 2008-11-12 |
| TW200410695A (en) | 2004-07-01 |
| PE20040736A1 (es) | 2004-12-08 |
| US20080293939A1 (en) | 2008-11-27 |
| JP4571863B2 (ja) | 2010-10-27 |
| CN1711249A (zh) | 2005-12-21 |
| US20060154942A1 (en) | 2006-07-13 |
| WO2004033435A1 (en) | 2004-04-22 |
| EP1554257A1 (en) | 2005-07-20 |
| GB0223730D0 (en) | 2002-11-20 |
| AR041563A1 (es) | 2005-05-18 |
| BR0314557A (pt) | 2005-08-09 |
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