MXPA04007641A - Derivados de quinazolinona y su uso como agonistas cb. - Google Patents
Derivados de quinazolinona y su uso como agonistas cb.Info
- Publication number
- MXPA04007641A MXPA04007641A MXPA04007641A MXPA04007641A MXPA04007641A MX PA04007641 A MXPA04007641 A MX PA04007641A MX PA04007641 A MXPA04007641 A MX PA04007641A MX PA04007641 A MXPA04007641 A MX PA04007641A MX PA04007641 A MXPA04007641 A MX PA04007641A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- alkylene
- hydroxy
- compound
- alkoxy
- Prior art date
Links
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 title abstract description 4
- 239000000556 agonist Substances 0.000 title description 11
- 238000000034 method Methods 0.000 claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 claims abstract description 18
- 230000008569 process Effects 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 104
- 229910052739 hydrogen Inorganic materials 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 239000001257 hydrogen Substances 0.000 claims description 56
- 239000002253 acid Substances 0.000 claims description 37
- 238000011282 treatment Methods 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
- 125000001931 aliphatic group Chemical group 0.000 claims description 19
- 125000006413 ring segment Chemical group 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 239000012458 free base Substances 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 15
- 102000018208 Cannabinoid Receptor Human genes 0.000 claims description 15
- 108050007331 Cannabinoid receptor Proteins 0.000 claims description 15
- -1 d-alkoxy Chemical group 0.000 claims description 15
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 15
- 230000004913 activation Effects 0.000 claims description 14
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 208000010412 Glaucoma Diseases 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 208000002193 Pain Diseases 0.000 claims description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 230000002265 prevention Effects 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 7
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 229940088679 drug related substance Drugs 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 208000000094 Chronic Pain Diseases 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 208000022873 Ocular disease Diseases 0.000 claims description 3
- 208000004760 Tenosynovitis Diseases 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 210000001328 optic nerve Anatomy 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 210000001525 retina Anatomy 0.000 claims description 3
- 201000005569 Gout Diseases 0.000 claims description 2
- 206010067013 Normal tension glaucoma Diseases 0.000 claims description 2
- UFXNCSRAJJJLJN-UHFFFAOYSA-N ethyl 2-(ethylcarbamoyloxymethyl)-5,7-dimethyl-3-[2-(methylsulfamoyl)phenyl]-4-oxoquinazoline-6-carboxylate Chemical compound CCNC(=O)OCC1=NC2=CC(C)=C(C(=O)OCC)C(C)=C2C(=O)N1C1=CC=CC=C1S(=O)(=O)NC UFXNCSRAJJJLJN-UHFFFAOYSA-N 0.000 claims description 2
- 201000002978 low tension glaucoma Diseases 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- 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 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 186
- 239000000243 solution Substances 0.000 description 70
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 239000011541 reaction mixture Substances 0.000 description 56
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000012074 organic phase Substances 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 239000007787 solid Substances 0.000 description 32
- 238000002360 preparation method Methods 0.000 description 31
- 239000003795 chemical substances by application Substances 0.000 description 30
- 239000000725 suspension Substances 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 239000008346 aqueous phase Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- 239000012267 brine Substances 0.000 description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
- 239000007832 Na2SO4 Substances 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 14
- 230000002829 reductive effect Effects 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
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- 238000001914 filtration Methods 0.000 description 11
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 241000700159 Rattus Species 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000012528 membrane Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
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- 239000007858 starting material Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 239000011343 solid material Substances 0.000 description 6
- SSEZSHJJNNLTQI-UHFFFAOYSA-N 2-amino-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1N SSEZSHJJNNLTQI-UHFFFAOYSA-N 0.000 description 5
- GNGNMHQUAACNST-UHFFFAOYSA-N 6-amino-3-ethoxycarbonyl-2,4-dimethylbenzoic acid Chemical compound CCOC(=O)C1=C(C)C=C(N)C(C(O)=O)=C1C GNGNMHQUAACNST-UHFFFAOYSA-N 0.000 description 5
- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 description 5
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- 208000004454 Hyperalgesia Diseases 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- OFBXYQLWNDBECP-UHFFFAOYSA-N 1-o-ethyl 3-o-methyl 4-amino-2,6-dimethylbenzene-1,3-dicarboxylate Chemical compound CCOC(=O)C1=C(C)C=C(N)C(C(=O)OC)=C1C OFBXYQLWNDBECP-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- IZIUWDBVKJOXMF-UHFFFAOYSA-N 3-ethoxycarbonyl-2,4-dimethyl-6-[(2-phenylmethoxyacetyl)amino]benzoic acid Chemical compound OC(=O)C1=C(C)C(C(=O)OCC)=C(C)C=C1NC(=O)COCC1=CC=CC=C1 IZIUWDBVKJOXMF-UHFFFAOYSA-N 0.000 description 4
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 description 4
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 4
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- KHPXDOBGSHNKDM-UHFFFAOYSA-N ethyl 2-(hydroxymethyl)-5,7-dimethyl-3-[2-(methylsulfamoyl)phenyl]-4-oxoquinazoline-6-carboxylate Chemical compound O=C1C2=C(C)C(C(=O)OCC)=C(C)C=C2N=C(CO)N1C1=CC=CC=C1S(=O)(=O)NC KHPXDOBGSHNKDM-UHFFFAOYSA-N 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- DLJPYODODWSDBI-UHFFFAOYSA-N n-methyl-2-nitrobenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O DLJPYODODWSDBI-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- 239000011734 sodium Substances 0.000 description 3
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 2
- WUFSMRKPYVAIFZ-UHFFFAOYSA-N 2-(hydroxymethyl)-5,7-dimethyl-3-[2-(methylsulfamoyl)phenyl]-4-oxoquinazoline-6-carboxylic acid Chemical compound CNS(=O)(=O)C1=CC=CC=C1N1C(=O)C2=C(C)C(C(O)=O)=C(C)C=C2N=C1CO WUFSMRKPYVAIFZ-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 2
- QISAUDWTBBNJIR-UHFFFAOYSA-N 2-phenylmethoxyacetyl chloride Chemical compound ClC(=O)COCC1=CC=CC=C1 QISAUDWTBBNJIR-UHFFFAOYSA-N 0.000 description 2
- WJDNHFSUJLHTAB-UHFFFAOYSA-N 3-ethoxycarbonyl-6-[(4-ethoxy-4-oxobutanoyl)amino]-2,4-dimethylbenzoic acid Chemical compound CCOC(=O)CCC(=O)NC1=CC(C)=C(C(=O)OCC)C(C)=C1C(O)=O WJDNHFSUJLHTAB-UHFFFAOYSA-N 0.000 description 2
- 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 2
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Classifications
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- 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
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Landscapes
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- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0202755A GB0202755D0 (en) | 2002-02-06 | 2002-02-06 | Organic compounds |
| GB0213285A GB0213285D0 (en) | 2002-06-10 | 2002-06-10 | Organic compound |
| GB0221460A GB0221460D0 (en) | 2002-09-16 | 2002-09-16 | Organic compound |
| GB0221459A GB0221459D0 (en) | 2002-09-16 | 2002-09-16 | Organic compound |
| PCT/EP2003/001140 WO2003066603A1 (en) | 2002-02-06 | 2003-02-05 | Quinazolinone derivatives and their use as cb agonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA04007641A true MXPA04007641A (es) | 2004-11-10 |
Family
ID=27739227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA04007641A MXPA04007641A (es) | 2002-02-06 | 2003-02-05 | Derivados de quinazolinona y su uso como agonistas cb. |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US20050085493A1 (enExample) |
| EP (2) | EP1472234B1 (enExample) |
| JP (2) | JP4428479B2 (enExample) |
| KR (1) | KR100954626B1 (enExample) |
| CN (1) | CN100579968C (enExample) |
| AR (1) | AR038483A1 (enExample) |
| AT (1) | ATE551329T1 (enExample) |
| AU (1) | AU2003210212A1 (enExample) |
| BR (1) | BR0307461A (enExample) |
| CA (1) | CA2471974C (enExample) |
| CO (1) | CO5601021A2 (enExample) |
| EC (1) | ECSP045219A (enExample) |
| ES (1) | ES2384967T3 (enExample) |
| MX (1) | MXPA04007641A (enExample) |
| MY (1) | MY143958A (enExample) |
| NO (1) | NO328305B1 (enExample) |
| NZ (1) | NZ571615A (enExample) |
| PE (1) | PE20030867A1 (enExample) |
| PL (1) | PL370657A1 (enExample) |
| TW (1) | TW200306839A (enExample) |
| WO (1) | WO2003066603A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000055153A1 (en) | 1999-03-17 | 2000-09-21 | Astrazeneca Ab | Amide derivatives |
| TW200306839A (en) | 2002-02-06 | 2003-12-01 | Novartis Ag | Quinazolinone derivatives and their use as CB agonists |
| GB0324790D0 (en) * | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Amide derivatives |
| JP2007510649A (ja) | 2003-11-04 | 2007-04-26 | メルク エンド カムパニー インコーポレーテッド | 置換ナフチリジノン誘導体 |
| SE0303491D0 (sv) * | 2003-12-19 | 2003-12-19 | Astrazeneca Ab | New use VI |
| CN100506802C (zh) * | 2004-06-04 | 2009-07-01 | 中国科学院上海药物研究所 | 一类甲酰肽样受体-1调节剂、其制备方法和用途 |
| GB0413618D0 (en) * | 2004-06-17 | 2004-07-21 | Novartis Ag | Organic compounds |
| EP1904068A1 (en) * | 2005-07-11 | 2008-04-02 | N.V. Organon | Synergistic combination for the treatment of pain (cannabioid receptor agonist and opiod receptor agonist) |
| GB0525068D0 (en) | 2005-12-08 | 2006-01-18 | Novartis Ag | Organic compounds |
| US20090209536A1 (en) * | 2007-06-17 | 2009-08-20 | Kalypsys, Inc. | Aminoquinazoline cannabinoid receptor modulators for treatment of disease |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| FR2944013B1 (fr) * | 2009-04-07 | 2011-07-15 | Sanofi Aventis | Derives de 1-alkyl-cinnolin-4(1h)-one substitues,leur preparation et leur application en therapeutique. |
| EP2531510B1 (en) | 2010-02-01 | 2014-07-23 | Novartis AG | Pyrazolo[5,1b]oxazole derivatives as crf-1 receptor antagonists |
| AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
| ES2527849T3 (es) | 2010-02-02 | 2015-01-30 | Novartis Ag | Derivados de ciclohexilamida como antagonistas del receptor de CRF |
| US8546416B2 (en) | 2011-05-27 | 2013-10-01 | Novartis Ag | 3-spirocyclic piperidine derivatives as ghrelin receptor agonists |
| CN104271579A (zh) | 2012-05-03 | 2015-01-07 | 诺华股份有限公司 | 作为生长素释放肽受体激动剂的2,7-二氮杂-螺[4,5]癸烷-7-基衍生物的l-苹果酸盐及其结晶 |
| UY35675A (es) | 2013-07-24 | 2015-02-27 | Novartis Ag | Derivados sustituidos de quinazolin-4-ona |
| CN106146414A (zh) * | 2016-07-07 | 2016-11-23 | 浙江大学 | 喹唑啉二酮类衍生物及其制备方法和用途 |
| CN106831502A (zh) * | 2017-03-13 | 2017-06-13 | 苏州市泽宸贸易有限公司 | 邻硝基苯磺酰氯、其合成方法及应用 |
| CN109796360B (zh) * | 2019-01-30 | 2022-03-18 | 上海阿拉丁生化科技股份有限公司 | 一种3-氨基-2-萘甲酸类化合物的制备工艺 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR6200M (enExample) | 1967-04-18 | 1968-07-22 | ||
| DE1803210A1 (de) | 1968-10-16 | 1970-05-14 | Troponwerke Dinklage & Co | 2-Methyl-3-(3-[4-phenylpiperazinyl-(1)]-2-hydroxypropyl)-chinazolinon-(4) und Verfahren zu seiner Herstellung |
| JPS5657768A (en) * | 1979-10-18 | 1981-05-20 | Masayuki Ishikawa | Novel 4-quinazolone derivative substituted by aromatic residue at 3-position |
| NZ192392A (en) * | 1978-12-19 | 1983-02-15 | M Ishikawa | 3-(substituted (phenyl or pyridyl)) -3,4-dihydroquinazolin-4-ones |
| JPS57118570A (en) * | 1981-01-16 | 1982-07-23 | Masayuki Ishikawa | Novel 3-phenyl-4-quinazolone derivative |
| AU543928B2 (en) * | 1981-01-16 | 1985-05-09 | Masayuki Ishikawa | 4(311)-quinazolinone derivatives |
| EP0639986A1 (en) * | 1992-05-13 | 1995-03-01 | Alcon Laboratories, Inc. | Topical ophthalmic compositions comprising a combination of calcium antagonists with known antiglaucoma agents |
| US6017919A (en) | 1996-02-06 | 2000-01-25 | Japan Tobacco Inc. | Compounds and pharmaceutical use thereof |
| TW200306839A (en) | 2002-02-06 | 2003-12-01 | Novartis Ag | Quinazolinone derivatives and their use as CB agonists |
| SE0303491D0 (sv) | 2003-12-19 | 2003-12-19 | Astrazeneca Ab | New use VI |
| GB0413618D0 (en) * | 2004-06-17 | 2004-07-21 | Novartis Ag | Organic compounds |
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2009
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| CN1628104A (zh) | 2005-06-15 |
| EP1472234B1 (en) | 2012-03-28 |
| JP2009149658A (ja) | 2009-07-09 |
| BR0307461A (pt) | 2004-11-09 |
| NO328305B1 (no) | 2010-01-25 |
| ATE551329T1 (de) | 2012-04-15 |
| AR038483A1 (es) | 2005-01-19 |
| EP2319839A1 (en) | 2011-05-11 |
| US20050085493A1 (en) | 2005-04-21 |
| JP4428479B2 (ja) | 2010-03-10 |
| US20070265285A1 (en) | 2007-11-15 |
| KR100954626B1 (ko) | 2010-04-27 |
| CO5601021A2 (es) | 2006-01-31 |
| WO2003066603A1 (en) | 2003-08-14 |
| NZ571615A (en) | 2010-01-29 |
| AU2003210212A1 (en) | 2003-09-02 |
| CN100579968C (zh) | 2010-01-13 |
| TW200306839A (en) | 2003-12-01 |
| NO20043580L (no) | 2004-09-21 |
| CA2471974A1 (en) | 2003-08-14 |
| ES2384967T3 (es) | 2012-07-16 |
| ECSP045219A (es) | 2004-09-28 |
| EP1472234A1 (en) | 2004-11-03 |
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| MY143958A (en) | 2011-07-29 |
| KR20040083501A (ko) | 2004-10-02 |
| PE20030867A1 (es) | 2003-12-04 |
| HK1079518A1 (zh) | 2006-04-07 |
| CA2471974C (en) | 2011-11-22 |
| JP2005522439A (ja) | 2005-07-28 |
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