AU2006311826C1 - Hydrazone derivatives and uses thereof - Google Patents
Hydrazone derivatives and uses thereof Download PDFInfo
- Publication number
- AU2006311826C1 AU2006311826C1 AU2006311826A AU2006311826A AU2006311826C1 AU 2006311826 C1 AU2006311826 C1 AU 2006311826C1 AU 2006311826 A AU2006311826 A AU 2006311826A AU 2006311826 A AU2006311826 A AU 2006311826A AU 2006311826 C1 AU2006311826 C1 AU 2006311826C1
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- AU
- Australia
- Prior art keywords
- optionally substituted
- aryl
- alkyl
- formula
- membered
- 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.)
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- 150000007857 hydrazones Chemical class 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 366
- -1 amino, hydroxy Chemical group 0.000 claims description 200
- 235000019640 taste Nutrition 0.000 claims description 148
- 238000000034 method Methods 0.000 claims description 143
- 125000000217 alkyl group Chemical group 0.000 claims description 118
- 125000003545 alkoxy group Chemical group 0.000 claims description 111
- 125000003118 aryl group Chemical group 0.000 claims description 78
- 230000002401 inhibitory effect Effects 0.000 claims description 77
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 72
- 125000003282 alkyl amino group Chemical group 0.000 claims description 70
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 69
- 239000003795 chemical substances by application Substances 0.000 claims description 61
- 229910052799 carbon Inorganic materials 0.000 claims description 57
- 125000005842 heteroatom Chemical group 0.000 claims description 55
- 235000013305 food Nutrition 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 38
- 239000008194 pharmaceutical composition Substances 0.000 claims description 37
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
- 235000019658 bitter taste Nutrition 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 32
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 31
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical group 0.000 claims description 30
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 29
- 125000001188 haloalkyl group Chemical group 0.000 claims description 29
- 239000000047 product Substances 0.000 claims description 29
- 108091005708 gustatory receptors Proteins 0.000 claims description 28
- 210000003370 receptor cell Anatomy 0.000 claims description 27
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 26
- 239000013543 active substance Substances 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 23
- 125000004414 alkyl thio group Chemical group 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 23
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 22
- 125000002431 aminoalkoxy group Chemical group 0.000 claims description 22
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 21
- 125000005111 carboxyalkoxy group Chemical group 0.000 claims description 20
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 18
- 101000844521 Homo sapiens Transient receptor potential cation channel subfamily M member 5 Proteins 0.000 claims description 17
- 125000002757 morpholinyl group Chemical group 0.000 claims description 17
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
- 125000005336 allyloxy group Chemical group 0.000 claims description 15
- 230000005764 inhibitory process Effects 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 102000003609 TRPM5 Human genes 0.000 claims description 14
- 230000028161 membrane depolarization Effects 0.000 claims description 13
- 239000002537 cosmetic Substances 0.000 claims description 11
- 125000001041 indolyl group Chemical group 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 239000013589 supplement Substances 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 8
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 7
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 claims description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 229940088710 antibiotic agent Drugs 0.000 claims description 5
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- 229930013930 alkaloid Natural products 0.000 claims description 4
- 229940035676 analgesics Drugs 0.000 claims description 4
- 230000000954 anitussive effect Effects 0.000 claims description 4
- 239000000730 antalgic agent Substances 0.000 claims description 4
- 230000003556 anti-epileptic effect Effects 0.000 claims description 4
- 230000001754 anti-pyretic effect Effects 0.000 claims description 4
- 239000001961 anticonvulsive agent Substances 0.000 claims description 4
- 229960003965 antiepileptics Drugs 0.000 claims description 4
- 239000002221 antipyretic Substances 0.000 claims description 4
- 229940125716 antipyretic agent Drugs 0.000 claims description 4
- 239000003434 antitussive agent Substances 0.000 claims description 4
- 229940124584 antitussives Drugs 0.000 claims description 4
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000003172 expectorant agent Substances 0.000 claims description 4
- 230000003419 expectorant effect Effects 0.000 claims description 4
- 229940066493 expectorants Drugs 0.000 claims description 4
- 235000012041 food component Nutrition 0.000 claims description 4
- 239000005417 food ingredient Substances 0.000 claims description 4
- 125000005638 hydrazono group Chemical group 0.000 claims description 4
- 239000008141 laxative Substances 0.000 claims description 4
- 229940125722 laxative agent Drugs 0.000 claims description 4
- WZCKOKPKQZIGNU-UHFFFAOYSA-N 1h-naphthalen-2-one Chemical compound C1=CC=C2C=CC(=O)CC2=C1 WZCKOKPKQZIGNU-UHFFFAOYSA-N 0.000 claims description 3
- CVHAOYYZBMXLSK-UHFFFAOYSA-N 2-(2-bromo-4-methoxyphenoxy)-n'-(5-bromo-2-oxoindol-3-yl)acetohydrazide Chemical compound BrC1=CC(OC)=CC=C1OCC(=O)NNC1=C(C=C(Br)C=C2)C2=NC1=O CVHAOYYZBMXLSK-UHFFFAOYSA-N 0.000 claims description 3
- YHKMAUXDLBNSDS-UHFFFAOYSA-N 2-(4-tert-butyl-2-methylphenoxy)-n'-(2-oxoindol-3-yl)acetohydrazide Chemical compound CC1=CC(C(C)(C)C)=CC=C1OCC(=O)NNC1=C(C=CC=C2)C2=NC1=O YHKMAUXDLBNSDS-UHFFFAOYSA-N 0.000 claims description 3
- CMUKQEBWRCYFTO-BKUYFWCQSA-N 2-[(2z)-2-[(1-butylindol-3-yl)methylidene]hydrazinyl]benzoic acid Chemical compound C12=CC=CC=C2N(CCCC)C=C1\C=N/NC1=CC=CC=C1C(O)=O CMUKQEBWRCYFTO-BKUYFWCQSA-N 0.000 claims description 3
- KMJNTVYEVZXFSD-UHFFFAOYSA-N 3-(1-hydroxycyclopentyl)-N-[(4-hydroxy-3-methoxyphenyl)methylideneamino]propanamide Chemical compound C1=C(O)C(OC)=CC(C=NNC(=O)CCC2(O)CCCC2)=C1 KMJNTVYEVZXFSD-UHFFFAOYSA-N 0.000 claims description 3
- OXPOYPYSXIYENU-XDHOZWIPSA-N 3-(cyclohexen-1-yl)-4-hydroxy-n-[(e)-(4-methoxyphenyl)methylideneamino]butanamide Chemical compound C1=CC(OC)=CC=C1\C=N\NC(=O)CC(CO)C1=CCCCC1 OXPOYPYSXIYENU-XDHOZWIPSA-N 0.000 claims description 3
- PCKVASYGPIUMJD-UHFFFAOYSA-N 4-nitro-n-[(3,4,5-trimethoxyphenyl)methylideneamino]benzamide Chemical compound COC1=C(OC)C(OC)=CC(C=NNC(=O)C=2C=CC(=CC=2)[N+]([O-])=O)=C1 PCKVASYGPIUMJD-UHFFFAOYSA-N 0.000 claims description 3
- JDXDUQJTANXNCY-KCAJXKFRSA-N 4-nitro-n-[(e)-[(2z)-2-(1,3,3-trimethylindol-2-ylidene)ethylidene]amino]aniline Chemical compound CC1(C)C2=CC=CC=C2N(C)\C1=C/C=N/NC1=CC=C([N+]([O-])=O)C=C1 JDXDUQJTANXNCY-KCAJXKFRSA-N 0.000 claims description 3
- 206010018498 Goitre Diseases 0.000 claims description 3
- MZCPYWVSWAQCSV-UHFFFAOYSA-N N-[1-[4-(diethylamino)phenyl]-3-[2-[(4-hydroxy-3-iodo-5-methoxyphenyl)methylidene]hydrazinyl]-3-oxoprop-1-en-2-yl]benzamide Chemical compound C1=CC(N(CC)CC)=CC=C1C=C(C(=O)NN=CC=1C=C(OC)C(O)=C(I)C=1)NC(=O)C1=CC=CC=C1 MZCPYWVSWAQCSV-UHFFFAOYSA-N 0.000 claims description 3
- 208000029650 alcohol withdrawal Diseases 0.000 claims description 3
- 230000003288 anthiarrhythmic effect Effects 0.000 claims description 3
- 230000001088 anti-asthma Effects 0.000 claims description 3
- 230000002686 anti-diuretic effect Effects 0.000 claims description 3
- 230000002421 anti-septic effect Effects 0.000 claims description 3
- 239000003416 antiarrhythmic agent Substances 0.000 claims description 3
- 239000000924 antiasthmatic agent Substances 0.000 claims description 3
- 229940124538 antidiuretic agent Drugs 0.000 claims description 3
- 239000003524 antilipemic agent Substances 0.000 claims description 3
- 229940064004 antiseptic throat preparations Drugs 0.000 claims description 3
- 239000002830 appetite depressant Substances 0.000 claims description 3
- 239000002876 beta blocker Substances 0.000 claims description 3
- XQOKEALRIAEASJ-XDHOZWIPSA-N chembl3192181 Chemical compound OC1=CC(N(CC)CC)=CC=C1\C=N\NC1=NC2=CC=CC=C2N1 XQOKEALRIAEASJ-XDHOZWIPSA-N 0.000 claims description 3
- 239000003246 corticosteroid Substances 0.000 claims description 3
- 239000000850 decongestant Substances 0.000 claims description 3
- 229940124581 decongestants Drugs 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 206010016766 flatulence Diseases 0.000 claims description 3
- 230000002496 gastric effect Effects 0.000 claims description 3
- 201000003872 goiter Diseases 0.000 claims description 3
- 239000003456 ion exchange resin Substances 0.000 claims description 3
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 3
- UBAPMBVNTQDXCR-YBFXNURJSA-N n-[(e)-(3,4-dimethoxyphenyl)methylideneamino]-2-(3-methylphenoxy)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1\C=N\NC(=O)COC1=CC=CC(C)=C1 UBAPMBVNTQDXCR-YBFXNURJSA-N 0.000 claims description 3
- UPKGLYTYDQRMDT-TXCUHAKESA-N n-[(e)-3-[(2z)-2-(1,5-dimethyl-2-oxoindol-3-ylidene)hydrazinyl]-3-oxo-1-phenylprop-1-en-2-yl]benzamide Chemical compound C12=CC(C)=CC=C2N(C)C(=O)\C1=N/NC(=O)C(=C/C=1C=CC=CC=1)\NC(=O)C1=CC=CC=C1 UPKGLYTYDQRMDT-TXCUHAKESA-N 0.000 claims description 3
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 3
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N o-dihydroxy-benzene Natural products OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 3
- NZOJDGVSAOPCON-UHFFFAOYSA-N propanehydrazide Chemical compound C[CH]C(=O)NN NZOJDGVSAOPCON-UHFFFAOYSA-N 0.000 claims description 3
- 230000001003 psychopharmacologic effect Effects 0.000 claims description 3
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims description 3
- 229960001755 resorcinol Drugs 0.000 claims description 3
- 229940125723 sedative agent Drugs 0.000 claims description 3
- 239000000932 sedative agent Substances 0.000 claims description 3
- 230000002048 spasmolytic effect Effects 0.000 claims description 3
- 239000011573 trace mineral Substances 0.000 claims description 3
- 235000013619 trace mineral Nutrition 0.000 claims description 3
- 239000003204 tranquilizing agent Substances 0.000 claims description 3
- 230000002936 tranquilizing effect Effects 0.000 claims description 3
- BSYBZDOJJOFUQO-UFFVCSGVSA-N 2-[4-bromo-2-[(e)-(quinolin-8-ylhydrazinylidene)methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1\C=N\NC1=CC=CC2=CC=CN=C12 BSYBZDOJJOFUQO-UFFVCSGVSA-N 0.000 claims description 2
- GAWNXJHMULLQKR-UHFFFAOYSA-N 3-(1h-indol-3-yl)-n-[(3,4,5-trimethoxyphenyl)methylideneamino]propanamide Chemical compound COC1=C(OC)C(OC)=CC(C=NNC(=O)CCC=2C3=CC=CC=C3NC=2)=C1 GAWNXJHMULLQKR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 229940125684 antimigraine agent Drugs 0.000 claims description 2
- 239000002282 antimigraine agent Substances 0.000 claims description 2
- WSFUEQPQUUWADO-HXNIXJDOSA-N c1cc(C(=O)OC)ccc1\N=N\C(\C(C)C)=N/Nc1nc2ccccc2s1 Chemical compound c1cc(C(=O)OC)ccc1\N=N\C(\C(C)C)=N/Nc1nc2ccccc2s1 WSFUEQPQUUWADO-HXNIXJDOSA-N 0.000 claims description 2
- VFSFCYAQBIPUSL-UHFFFAOYSA-N cyclopropylbenzene Chemical compound C1CC1C1=CC=CC=C1 VFSFCYAQBIPUSL-UHFFFAOYSA-N 0.000 claims description 2
- WXIZGSXALDOMNQ-MHWRWJLKSA-N n-[(e)-(3,4-dimethoxyphenyl)methylideneamino]-4-hydroxyhexanamide Chemical compound CCC(O)CCC(=O)N\N=C\C1=CC=C(OC)C(OC)=C1 WXIZGSXALDOMNQ-MHWRWJLKSA-N 0.000 claims description 2
- IGLLZRSXKVWXEV-RCCKNPSSSA-N n-benzyl-n-[(e)-pyridin-4-ylmethylideneamino]aniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)\N=C\C1=CC=NC=C1 IGLLZRSXKVWXEV-RCCKNPSSSA-N 0.000 claims description 2
- JFYKIEHOOZWARC-UHFFFAOYSA-N cyclopropanecarbohydrazide Chemical compound NNC(=O)C1CC1 JFYKIEHOOZWARC-UHFFFAOYSA-N 0.000 claims 34
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims 3
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 claims 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 2
- 229940127557 pharmaceutical product Drugs 0.000 claims 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- FMIDDBFKNHOFAK-UHFFFAOYSA-N 2-[[4-(trifluoromethylsulfanyl)phenyl]hydrazinylidene]propanedinitrile Chemical compound FC(F)(F)SC1=CC=C(NN=C(C#N)C#N)C=C1 FMIDDBFKNHOFAK-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 239000008406 cosmetic ingredient Substances 0.000 claims 1
- 229950011148 cyclopropane Drugs 0.000 claims 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- OGJBULMMRFGWAP-UHFFFAOYSA-N n-[(3,4-dimethoxyphenyl)methylideneamino]-2-(4,8-dimethylquinolin-2-yl)sulfanylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1C=NNC(=O)CSC1=CC(C)=C(C=CC=C2C)C2=N1 OGJBULMMRFGWAP-UHFFFAOYSA-N 0.000 claims 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 235000018102 proteins Nutrition 0.000 description 104
- 102000004169 proteins and genes Human genes 0.000 description 104
- 108090000623 proteins and genes Proteins 0.000 description 104
- 239000000203 mixture Substances 0.000 description 87
- 125000005647 linker group Chemical group 0.000 description 42
- 125000004432 carbon atom Chemical group C* 0.000 description 32
- 210000004027 cell Anatomy 0.000 description 30
- 235000002639 sodium chloride Nutrition 0.000 description 29
- 125000003342 alkenyl group Chemical group 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- 241001465754 Metazoa Species 0.000 description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 20
- 150000003573 thiols Chemical group 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 230000008569 process Effects 0.000 description 17
- 239000000460 chlorine Substances 0.000 description 16
- 239000003814 drug Substances 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 13
- 239000011575 calcium Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000003556 assay Methods 0.000 description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
- 239000012528 membrane Substances 0.000 description 12
- 239000002417 nutraceutical Substances 0.000 description 12
- 125000005422 alkyl sulfonamido group Chemical group 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- 230000004048 modification Effects 0.000 description 11
- 238000012986 modification Methods 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- 241000282414 Homo sapiens Species 0.000 description 10
- 125000000304 alkynyl group Chemical group 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 9
- 125000005087 alkynylcarbonyl group Chemical group 0.000 description 9
- 125000005139 alkynylsulfonyl group Chemical group 0.000 description 9
- 235000001014 amino acid Nutrition 0.000 description 9
- 150000001413 amino acids Chemical group 0.000 description 9
- 125000005421 aryl sulfonamido group Chemical group 0.000 description 9
- 229910052791 calcium Inorganic materials 0.000 description 9
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/69—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine
- A61K8/70—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine containing perfluoro groups, e.g. perfluoroethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Birds (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Seasonings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73263405P | 2005-11-03 | 2005-11-03 | |
| US60/732,634 | 2005-11-03 | ||
| PCT/US2006/042988 WO2007056159A2 (en) | 2005-11-03 | 2006-11-03 | Hydrazone derivatives and uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| AU2006311826A1 AU2006311826A1 (en) | 2007-05-18 |
| AU2006311826B2 AU2006311826B2 (en) | 2010-11-11 |
| AU2006311826C1 true AU2006311826C1 (en) | 2011-06-16 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2006311826A Ceased AU2006311826C1 (en) | 2005-11-03 | 2006-11-03 | Hydrazone derivatives and uses thereof |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20070207093A1 (enExample) |
| EP (1) | EP1951215A4 (enExample) |
| JP (1) | JP2009514878A (enExample) |
| KR (1) | KR20080070848A (enExample) |
| CN (1) | CN101541348A (enExample) |
| AU (1) | AU2006311826C1 (enExample) |
| BR (1) | BRPI0618224A2 (enExample) |
| CA (1) | CA2626846A1 (enExample) |
| NO (1) | NO20082346L (enExample) |
| RU (1) | RU2008115539A (enExample) |
| WO (1) | WO2007056159A2 (enExample) |
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| US9101160B2 (en) | 2005-11-23 | 2015-08-11 | The Coca-Cola Company | Condiments with high-potency sweetener |
| CA2643559A1 (en) | 2006-03-02 | 2007-09-07 | Siga Technologies, Inc. | Antiviral drugs for treatment of arenavirus infection |
| ES2395101T3 (es) | 2006-03-02 | 2013-02-08 | Siga Technologies, Inc. | Medicamentos antivirales para tratamiento de infecciones por arenavirus |
| US8871746B2 (en) | 2006-03-02 | 2014-10-28 | Kineta Four, LLC | Antiviral drugs for treatment of arenavirus infection |
| US8017168B2 (en) | 2006-11-02 | 2011-09-13 | The Coca-Cola Company | High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith |
| AU2008214338A1 (en) * | 2007-02-02 | 2008-08-14 | Redpoint Bio Corporation | Use of a TRPM5 inhibitor to regulate insulin and GLP-1 release |
| US8609649B2 (en) * | 2007-03-20 | 2013-12-17 | Brandeis University | Compositions and methods for the diagnosis, treatment, and prevention of amyotrophic lateral sclerosis and related neurological diseases |
| WO2009038722A1 (en) * | 2007-09-17 | 2009-03-26 | Redpoint Bio Corporation | Modulation of the cooperativity between the ion channels trpm5 and trpa1 |
| EP2212285A1 (en) * | 2007-11-21 | 2010-08-04 | NeuroSearch A/S | N-acylhydrazone derivatives useful as modulators of nicotinic acetylcholine receptors |
| WO2010132615A1 (en) * | 2009-05-12 | 2010-11-18 | Philip Stein | Hydrazone compounds and their use |
| EP2605660A2 (en) * | 2010-08-20 | 2013-06-26 | Dow AgroSciences LLC | Synergistic fungicidal and algicidal compositions including 7-hydroxy-indanone benzoylhydrazones and copper |
| PH12013502686A1 (en) | 2011-06-24 | 2014-02-17 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| US9266838B2 (en) | 2011-08-15 | 2016-02-23 | University Of Utah Research Foundation | Substituted (E)-N′-(1-phenylethylidene)benzohydrazide analogs as histone demethylase inhibitors |
| JP6122006B2 (ja) | 2011-08-15 | 2017-04-26 | ザ ユニバーシティ オブ ユタ リサーチ ファウンデイション | ヒストン脱メチル化酵素阻害剤としての、置換された（ｅ）−ｎ’−（１−フェニルエチリデン）ベンゾヒドラジド類似体 |
| BRPI1106472A2 (pt) * | 2011-11-29 | 2014-04-15 | Univ Rio De Janeiro | Compostos n-glicinil-n-acilidrazônicos heterocíclicos, processo de síntese, composições farmacêuticas e método de tratamento |
| JP6382840B2 (ja) | 2012-12-19 | 2018-08-29 | ダウ アグロサイエンシィズ エルエルシー | 農薬組成物およびそれらに関する方法 |
| CA2894204A1 (en) | 2012-12-19 | 2014-08-07 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| MX2015008064A (es) | 2012-12-19 | 2016-04-21 | Dow Agrosciences Llc | Composiciones pesticidas y procesos relacionados con ellas. |
| WO2014100163A1 (en) * | 2012-12-19 | 2014-06-26 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| US9211280B2 (en) | 2012-12-19 | 2015-12-15 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| TWI667224B (zh) | 2014-06-09 | 2019-08-01 | 美商陶氏農業科學公司 | 殺蟲組成物及與其相關之方法 |
| WO2017132023A1 (en) | 2016-01-25 | 2017-08-03 | Dow Agrosciences Llc | Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto |
| CN105732476B (zh) * | 2016-02-04 | 2017-12-01 | 吉首大学 | 一种咔唑‑靛红型化合物及其制法和用途 |
| RU2691454C2 (ru) * | 2016-03-30 | 2019-06-14 | Федеральное государственное бюджетное научное учреждение "Научно-исследовательский институт фармакологии имени В.В. Закусова" | Использование 3,4,5-триметокси-N'(2,2,6,6-тетраметил-пиперидин-4-илиден)бензогидразида гидрохлорида в качестве анксиолитического средства |
| RU2699658C2 (ru) * | 2016-08-19 | 2019-09-09 | Федеральное государственное бюджетное научное учреждение "Научно-исследовательский институт фармакологии имени В.В. Закусова" | Ацилгидразон (2,3,4-триметокси-N'-(8-метил-8-азабицикло[3.2.1.] октан-3-илиден) бензогидразид гидрохлорид), обладающий противомигреневой и анксиолитической активностью |
| TWI780112B (zh) | 2017-03-31 | 2022-10-11 | 美商科迪華農業科技有限責任公司 | 具有殺蟲效用之分子，及其相關之中間物、組成物暨方法 |
| KR102128509B1 (ko) * | 2018-12-19 | 2020-07-01 | 한국과학기술연구원 | 말단 아민기에 아릴 또는 헤테로아릴기가 치환된 신규한 히드라존 유도체 및 이의 용도 |
| WO2024156007A1 (en) * | 2023-01-20 | 2024-07-25 | The Research Foundation For The State University Of New York | Hydrazonyl sultones and uses thereof |
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| US5072042A (en) * | 1989-02-10 | 1991-12-10 | Basf Aktiengesellschaft | Phenylhydrazones, the manufacture thereof and therapeutic and cosmetic compositions prepared therefrom |
| WO1992019236A1 (en) * | 1991-05-07 | 1992-11-12 | The Rockefeller University | 2-alkylidene-aminoguanidines for inhibiting advanced nonenzymaticglycosylation of proteins |
| WO1999040062A1 (en) * | 1998-02-05 | 1999-08-12 | Novo Nordisk A/S | Hydrazone derivatives |
| WO2003049698A2 (en) * | 2001-12-10 | 2003-06-19 | Temple University - Of The Commonwealth System Of Higher Education | Substituted hydrazones as inhibitors of cyclooxygenase-2 |
| WO2004072183A1 (en) * | 2003-02-17 | 2004-08-26 | Ciba Specialty Chemicals Holding Inc. | Cationic substituted hydrazone dyes |
| WO2004083312A2 (en) * | 2003-03-18 | 2004-09-30 | Ciba Specialty Chemicals Holding Inc. | Cationic dimeric dyes |
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-
2006
- 2006-11-03 WO PCT/US2006/042988 patent/WO2007056159A2/en not_active Ceased
- 2006-11-03 CA CA002626846A patent/CA2626846A1/en not_active Abandoned
- 2006-11-03 KR KR1020087013242A patent/KR20080070848A/ko not_active Ceased
- 2006-11-03 CN CNA2006800504030A patent/CN101541348A/zh active Pending
- 2006-11-03 BR BRPI0618224-0A patent/BRPI0618224A2/pt not_active IP Right Cessation
- 2006-11-03 US US11/592,228 patent/US20070207093A1/en not_active Abandoned
- 2006-11-03 RU RU2008115539/14A patent/RU2008115539A/ru not_active Application Discontinuation
- 2006-11-03 EP EP06827464A patent/EP1951215A4/en not_active Withdrawn
- 2006-11-03 AU AU2006311826A patent/AU2006311826C1/en not_active Ceased
- 2006-11-03 JP JP2008539066A patent/JP2009514878A/ja not_active Withdrawn
-
2008
- 2008-05-23 NO NO20082346A patent/NO20082346L/no not_active Application Discontinuation
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| US5072042A (en) * | 1989-02-10 | 1991-12-10 | Basf Aktiengesellschaft | Phenylhydrazones, the manufacture thereof and therapeutic and cosmetic compositions prepared therefrom |
| WO1992019236A1 (en) * | 1991-05-07 | 1992-11-12 | The Rockefeller University | 2-alkylidene-aminoguanidines for inhibiting advanced nonenzymaticglycosylation of proteins |
| WO1999040062A1 (en) * | 1998-02-05 | 1999-08-12 | Novo Nordisk A/S | Hydrazone derivatives |
| WO2003049698A2 (en) * | 2001-12-10 | 2003-06-19 | Temple University - Of The Commonwealth System Of Higher Education | Substituted hydrazones as inhibitors of cyclooxygenase-2 |
| WO2004072183A1 (en) * | 2003-02-17 | 2004-08-26 | Ciba Specialty Chemicals Holding Inc. | Cationic substituted hydrazone dyes |
| WO2004083312A2 (en) * | 2003-03-18 | 2004-09-30 | Ciba Specialty Chemicals Holding Inc. | Cationic dimeric dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0618224A2 (pt) | 2011-08-23 |
| EP1951215A4 (en) | 2009-07-29 |
| WO2007056159A2 (en) | 2007-05-18 |
| KR20080070848A (ko) | 2008-07-31 |
| JP2009514878A (ja) | 2009-04-09 |
| CA2626846A1 (en) | 2007-05-18 |
| EP1951215A2 (en) | 2008-08-06 |
| AU2006311826A1 (en) | 2007-05-18 |
| AU2006311826B2 (en) | 2010-11-11 |
| NO20082346L (no) | 2008-08-04 |
| CN101541348A (zh) | 2009-09-23 |
| WO2007056159A3 (en) | 2008-10-16 |
| US20070207093A1 (en) | 2007-09-06 |
| RU2008115539A (ru) | 2009-12-10 |
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