MX2010008111A - Inhibidores de aldh-2 en el tratamiento de adicciones. - Google Patents
Inhibidores de aldh-2 en el tratamiento de adicciones.Info
- Publication number
- MX2010008111A MX2010008111A MX2010008111A MX2010008111A MX2010008111A MX 2010008111 A MX2010008111 A MX 2010008111A MX 2010008111 A MX2010008111 A MX 2010008111A MX 2010008111 A MX2010008111 A MX 2010008111A MX 2010008111 A MX2010008111 A MX 2010008111A
- Authority
- MX
- Mexico
- Prior art keywords
- phenyl
- chromen
- compound
- hydroxyphenyl
- methoxy
- Prior art date
Links
- 206010012335 Dependence Diseases 0.000 title claims abstract description 17
- 239000003112 inhibitor Substances 0.000 title abstract description 11
- 238000011282 treatment Methods 0.000 title description 29
- -1 amphetamines Chemical compound 0.000 claims abstract description 289
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 71
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims abstract description 68
- 229960003920 cocaine Drugs 0.000 claims abstract description 34
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims abstract description 20
- 229960002715 nicotine Drugs 0.000 claims abstract description 20
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 18
- 241000124008 Mammalia Species 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 295
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 112
- 125000000217 alkyl group Chemical group 0.000 claims description 96
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 73
- 125000001072 heteroaryl group Chemical group 0.000 claims description 65
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 239000001257 hydrogen Substances 0.000 claims description 63
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 57
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 53
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 53
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 43
- 150000002431 hydrogen Chemical group 0.000 claims description 42
- 125000003545 alkoxy group Chemical group 0.000 claims description 40
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 40
- 229910052760 oxygen Inorganic materials 0.000 claims description 40
- 239000001301 oxygen Substances 0.000 claims description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
- 125000000623 heterocyclic group Chemical group 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical group 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000002947 alkylene group Chemical group 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 21
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 239000005711 Benzoic acid Substances 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 235000010233 benzoic acid Nutrition 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Chemical group 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 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- 101100240527 Caenorhabditis elegans nhr-22 gene Proteins 0.000 claims description 4
- 229940127240 opiate Drugs 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- HTFFABIIOAKIBH-UHFFFAOYSA-N diazinane Chemical compound C1CCNNC1 HTFFABIIOAKIBH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 9
- NSJKIAFITKUSDQ-UHFFFAOYSA-N 2-morpholin-4-ylethyl 3-[[3-[4-(methanesulfonamido)phenyl]-4-oxochromen-7-yl]oxymethyl]benzoate Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=COC2=CC(OCC=3C=C(C=CC=3)C(=O)OCCN3CCOCC3)=CC=C2C1=O NSJKIAFITKUSDQ-UHFFFAOYSA-N 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical group COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 125000005310 triazolidinyl group Chemical group N1(NNCC1)* 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 21
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 abstract description 16
- 229940079593 drug Drugs 0.000 abstract description 16
- 229960003638 dopamine Drugs 0.000 abstract description 8
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 abstract description 4
- 150000002515 isoflavone derivatives Chemical class 0.000 abstract description 3
- 229960005181 morphine Drugs 0.000 abstract description 2
- 229930012930 isoflavone derivative Natural products 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 142
- 239000000203 mixture Substances 0.000 description 138
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 100
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 99
- 238000006243 chemical reaction Methods 0.000 description 97
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 89
- 238000002360 preparation method Methods 0.000 description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 69
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 67
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 64
- 239000002904 solvent Substances 0.000 description 61
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 56
- 239000000243 solution Substances 0.000 description 55
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
- 235000019439 ethyl acetate Nutrition 0.000 description 52
- 230000002829 reductive effect Effects 0.000 description 46
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 40
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N daidzein Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 description 38
- 239000000725 suspension Substances 0.000 description 38
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 36
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 30
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 22
- 125000004181 carboxyalkyl group Chemical group 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 238000012360 testing method Methods 0.000 description 21
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 20
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
- 150000001412 amines Chemical class 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 20
- 239000000843 powder Substances 0.000 description 20
- 229910052938 sodium sulfate Inorganic materials 0.000 description 20
- 235000011152 sodium sulphate Nutrition 0.000 description 20
- 239000003826 tablet Substances 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- 102000005369 Aldehyde Dehydrogenase Human genes 0.000 description 19
- 108020002663 Aldehyde Dehydrogenase Proteins 0.000 description 19
- 230000000694 effects Effects 0.000 description 19
- 239000004615 ingredient Substances 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- 235000007240 daidzein Nutrition 0.000 description 18
- 239000012267 brine Substances 0.000 description 17
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- 125000000392 cycloalkenyl group Chemical group 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- 239000012442 inert solvent Substances 0.000 description 16
- WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 15
- 241001465754 Metazoa Species 0.000 description 15
- 235000013305 food Nutrition 0.000 description 15
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 14
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- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 description 13
- MFVRXOUUMYWYLQ-UHFFFAOYSA-N N-[4-(4-oxochromen-2-yl)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C(C=C1)C=1OC2=CC=CC=C2C(C=1)=O MFVRXOUUMYWYLQ-UHFFFAOYSA-N 0.000 description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 13
- 229940095102 methyl benzoate Drugs 0.000 description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 239000000460 chlorine Chemical group 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
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- 238000003818 flash chromatography Methods 0.000 description 12
- 125000005843 halogen group Chemical group 0.000 description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
- 238000002347 injection Methods 0.000 description 11
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- 230000004044 response Effects 0.000 description 11
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 125000004414 alkyl thio group Chemical group 0.000 description 10
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N benzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 10
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
- C07D311/36—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only not hydrogenated in the hetero ring, e.g. isoflavones
-
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- A—HUMAN NECESSITIES
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
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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
-
- 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
-
- 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
-
- 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
-
- 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
- C07D417/12—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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Addiction (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2008/051862 WO2009094028A1 (en) | 2008-01-24 | 2008-01-24 | Aldh-2 inhibitors in the treatment of addiction |
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| MX2010008111A true MX2010008111A (es) | 2010-11-30 |
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| CN102161648A (zh) * | 2011-02-18 | 2011-08-24 | 中国药科大学 | 具有选择性雌激素受体调节活性的异黄酮类化合物的制备方法及其用途 |
| TWI567061B (zh) | 2011-07-01 | 2017-01-21 | 吉李德科學股份有限公司 | 用於治療成癮之化合物 |
| TWI468403B (zh) * | 2011-08-30 | 2015-01-11 | Gilead Sciences Inc | 用於治療成癮之ａｌｄｈ－２抑制劑 |
| KR20200070273A (ko) * | 2017-10-16 | 2020-06-17 | 아미그달라 뉴로사이언시즈, 인크. | 중독을 예방하기 위한 병용 요법 |
| CN108276374B (zh) * | 2018-03-29 | 2020-01-31 | 天津科技大学 | 黄酮类芳香化酶抑制剂及其制备方法与应用 |
| CN110922394B (zh) * | 2019-11-21 | 2021-04-06 | 中国科学院宁波材料技术与工程研究所 | 一种基于天然黄酮类化合物的生物基本征阻燃环氧树脂前驱体及其制备方法和应用 |
| US20250313532A1 (en) * | 2022-05-31 | 2025-10-09 | University Of Maryland, Baltimore | Aldh2 inhibitors and methods of use thereof |
| US20230399299A1 (en) | 2022-06-14 | 2023-12-14 | Amygdala Neurosciences, Inc. | Aldh-2 inhibitor compounds and methods of use |
| JP2025520426A (ja) | 2022-06-14 | 2025-07-03 | アミグダラ ニューロサイエンシーズ， インコーポレイテッド | Ａｌｄｈ－２阻害化合物及び使用方法 |
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| GB8626344D0 (en) * | 1986-11-04 | 1986-12-03 | Zyma Sa | Bicyclic compounds |
| US5204369A (en) * | 1991-07-01 | 1993-04-20 | The Endowment For Research In Human Biology | Method for the inhibition of aldh-i useful in the treatment of alcohol dependence or alcohol abuse |
| AU3899199A (en) * | 1998-05-12 | 1999-11-29 | Endowment for Research in Human Biology, Inc., The | Methods and assays useful in the treatment of alcohol dependence or alcohol abuse |
| CA2445515A1 (en) * | 2001-05-04 | 2002-11-04 | Paratek Pharmaceuticals, Inc. | Transcription factor modulating compounds and methods of use thereof |
| AUPR957001A0 (en) * | 2001-12-19 | 2002-01-24 | Novogen Research Pty Ltd | Isoflavone conjugates, derivatives thereof and therapeutic methods involving same |
| MXPA05000122A (es) * | 2002-06-27 | 2005-12-14 | Endowment For Res In Human Bio | Compuestos utiles para la inhibicion de aldehido-deshidrogenasa. |
| WO2006002422A2 (en) * | 2004-06-24 | 2006-01-05 | Novartis Vaccines And Diagnostics Inc. | Compounds for immunopotentiation |
| PL377180A1 (pl) * | 2005-09-21 | 2007-04-02 | Instytut Farmaceutyczny | Zastosowanie izoflawonów i ich pochodnych w leczeniu mukopolisacharydoz |
| WO2008014497A2 (en) * | 2006-07-27 | 2008-01-31 | Cv Therapeutics, Inc. | Aldh-2 inhibitors in the treatment of addiction |
| AU2008323953A1 (en) * | 2007-11-06 | 2009-05-14 | Gilead Palo Alto, Inc. | ALDH-2 inhibitors in the treatment of psychiatric disorders |
-
2008
- 2008-01-24 CN CN200880125439XA patent/CN101925590A/zh active Pending
- 2008-01-24 AU AU2008348372A patent/AU2008348372A1/en not_active Abandoned
- 2008-01-24 EP EP08713963A patent/EP2254878A1/en not_active Withdrawn
- 2008-01-24 JP JP2010544284A patent/JP2011510072A/ja active Pending
- 2008-01-24 BR BRPI0822129-4A patent/BRPI0822129A2/pt not_active IP Right Cessation
- 2008-01-24 CA CA2712750A patent/CA2712750A1/en not_active Abandoned
- 2008-01-24 MX MX2010008111A patent/MX2010008111A/es not_active Application Discontinuation
- 2008-01-24 KR KR1020107016579A patent/KR20100130589A/ko not_active Withdrawn
- 2008-01-24 WO PCT/US2008/051862 patent/WO2009094028A1/en not_active Ceased
-
2010
- 2010-07-02 ZA ZA2010/04671A patent/ZA201004671B/en unknown
- 2010-07-21 IL IL207127A patent/IL207127A0/en unknown
- 2010-08-23 MA MA33106A patent/MA32095B1/fr unknown
- 2010-08-23 EC EC2010010417A patent/ECSP10010417A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2011510072A (ja) | 2011-03-31 |
| EP2254878A1 (en) | 2010-12-01 |
| BRPI0822129A2 (pt) | 2015-06-23 |
| KR20100130589A (ko) | 2010-12-13 |
| WO2009094028A1 (en) | 2009-07-30 |
| AU2008348372A1 (en) | 2009-07-30 |
| CA2712750A1 (en) | 2009-07-30 |
| MA32095B1 (fr) | 2011-02-01 |
| ZA201004671B (en) | 2011-03-30 |
| CN101925590A (zh) | 2010-12-22 |
| ECSP10010417A (es) | 2010-11-30 |
| IL207127A0 (en) | 2010-12-30 |
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| FA | Abandonment or withdrawal |