JP2003206273A5 - - Google Patents
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- Publication number
- JP2003206273A5 JP2003206273A5 JP2002344313A JP2002344313A JP2003206273A5 JP 2003206273 A5 JP2003206273 A5 JP 2003206273A5 JP 2002344313 A JP2002344313 A JP 2002344313A JP 2002344313 A JP2002344313 A JP 2002344313A JP 2003206273 A5 JP2003206273 A5 JP 2003206273A5
- Authority
- JP
- Japan
- Prior art keywords
- hydrazide
- phenylsulfonyl
- benzoic acid
- group
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
- -1 2,4,6-trichlorophenyl Chemical group 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 102
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 74
- 239000005711 Benzoic acid Substances 0.000 claims 51
- 235000010233 benzoic acid Nutrition 0.000 claims 51
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 45
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 36
- RYAQFHLUEMJOMF-UHFFFAOYSA-N 4-phenoxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=CC=C1 RYAQFHLUEMJOMF-UHFFFAOYSA-N 0.000 claims 21
- 239000003814 drug Substances 0.000 claims 4
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims 3
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 claims 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 3
- NXTDJHZGHOFSQG-UHFFFAOYSA-N 3-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 NXTDJHZGHOFSQG-UHFFFAOYSA-N 0.000 claims 3
- RUKQTQBNZPGYEM-UHFFFAOYSA-N 4-(3-cyclohexyl-3-hydroxyprop-1-ynyl)benzoic acid Chemical compound C1CCCCC1C(O)C#CC1=CC=C(C(O)=O)C=C1 RUKQTQBNZPGYEM-UHFFFAOYSA-N 0.000 claims 3
- SFBBJEGGWMPLQJ-UHFFFAOYSA-N 4-(3-cyclohexyl-3-hydroxypropyl)benzoic acid Chemical compound C1CCCCC1C(O)CCC1=CC=C(C(O)=O)C=C1 SFBBJEGGWMPLQJ-UHFFFAOYSA-N 0.000 claims 3
- LWIWQNOVDMFNIE-UHFFFAOYSA-N 4-(3-cyclohexylprop-1-ynyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C#CCC1CCCCC1 LWIWQNOVDMFNIE-UHFFFAOYSA-N 0.000 claims 3
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- GHICCUXQJBDNRN-UHFFFAOYSA-N 4-iodobenzoic acid Chemical compound OC(=O)C1=CC=C(I)C=C1 GHICCUXQJBDNRN-UHFFFAOYSA-N 0.000 claims 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 3
- AQSCHALQLXXKKC-UHFFFAOYSA-N 4-phenylmethoxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OCC1=CC=CC=C1 AQSCHALQLXXKKC-UHFFFAOYSA-N 0.000 claims 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 3
- LSOFAILPHHNWGC-UHFFFAOYSA-N n'-(benzenesulfonyl)-4-(3,3-dimethylbut-1-ynyl)benzohydrazide Chemical compound C1=CC(C#CC(C)(C)C)=CC=C1C(=O)NNS(=O)(=O)C1=CC=CC=C1 LSOFAILPHHNWGC-UHFFFAOYSA-N 0.000 claims 3
- WZXUVTAFGVYIKH-UHFFFAOYSA-N n'-(benzenesulfonyl)-4-(3,3-dimethylbutyl)benzohydrazide Chemical compound C1=CC(CCC(C)(C)C)=CC=C1C(=O)NNS(=O)(=O)C1=CC=CC=C1 WZXUVTAFGVYIKH-UHFFFAOYSA-N 0.000 claims 3
- YFDAVAAGHFJNNJ-UHFFFAOYSA-N n'-(benzenesulfonyl)-4-(benzylamino)benzohydrazide Chemical compound C=1C=C(NCC=2C=CC=CC=2)C=CC=1C(=O)NNS(=O)(=O)C1=CC=CC=C1 YFDAVAAGHFJNNJ-UHFFFAOYSA-N 0.000 claims 3
- AMFBOZCNCIJSRM-UHFFFAOYSA-N n'-(benzenesulfonyl)-4-phenylbenzohydrazide Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)NNS(=O)(=O)C1=CC=CC=C1 AMFBOZCNCIJSRM-UHFFFAOYSA-N 0.000 claims 3
- RDZRXNGRHJDBLZ-UHFFFAOYSA-N n'-(benzenesulfonyl)-4-tert-butylbenzohydrazide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NNS(=O)(=O)C1=CC=CC=C1 RDZRXNGRHJDBLZ-UHFFFAOYSA-N 0.000 claims 3
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- 230000006698 induction Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 206010048843 Cytomegalovirus chorioretinitis Diseases 0.000 claims 1
- 206010011878 Deafness Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 208000013016 Hypoglycemia Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000007101 Muscle Cramp Diseases 0.000 claims 1
- 208000001738 Nervous System Trauma Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 208000005392 Spasm Diseases 0.000 claims 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 1
- 102000003929 Transaminases Human genes 0.000 claims 1
- 108090000340 Transaminases Proteins 0.000 claims 1
- 206010046543 Urinary incontinence Diseases 0.000 claims 1
- 230000002411 adverse Effects 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 229940126574 aminoglycoside antibiotic Drugs 0.000 claims 1
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 208000001763 cytomegalovirus retinitis Diseases 0.000 claims 1
- 230000007547 defect Effects 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000003257 excitatory amino acid Substances 0.000 claims 1
- 230000002461 excitatory amino acid Effects 0.000 claims 1
- 230000010370 hearing loss Effects 0.000 claims 1
- 231100000888 hearing loss Toxicity 0.000 claims 1
- 208000016354 hearing loss disease Diseases 0.000 claims 1
- 230000002218 hypoglycaemic effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 230000001537 neural effect Effects 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 238000011282 treatment Methods 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 125000001769 aryl amino group Chemical group 0.000 description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- 125000004442 acylamino group Chemical group 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 3
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 125000004658 aryl carbonyl amino group Chemical group 0.000 description 3
- 125000005199 aryl carbonyloxy group Chemical group 0.000 description 3
- 125000005110 aryl thio group Chemical group 0.000 description 3
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 3
- 150000007942 carboxylates Chemical group 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical group [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 125000000565 sulfonamide group Chemical group 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000005089 alkenylaminocarbonyl group Chemical group 0.000 description 2
- 125000005090 alkenylcarbonyl group Chemical group 0.000 description 2
- 125000004947 alkyl aryl amino group Chemical group 0.000 description 2
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 description 2
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 2
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 125000004986 diarylamino group Chemical group 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- PEPBFCOIJRULGJ-UHFFFAOYSA-N 3h-1,2,3-benzodioxazole Chemical compound C1=CC=C2NOOC2=C1 PEPBFCOIJRULGJ-UHFFFAOYSA-N 0.000 description 1
- 101710105312 Branched-chain-amino-acid aminotransferase Proteins 0.000 description 1
- 101710097328 Branched-chain-amino-acid aminotransferase, cytosolic Proteins 0.000 description 1
- 101710194298 Branched-chain-amino-acid aminotransferase, mitochondrial Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 101710158343 Probable branched-chain-amino-acid aminotransferase Proteins 0.000 description 1
- 101710199693 Putative branched-chain-amino-acid aminotransferase Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- AZPBDRUPTRGILK-UHFFFAOYSA-N benzotriazol-1-ium-1-ylidenemethanediamine;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.C1=CC=C2N(C(=N)N)N=NC2=C1 AZPBDRUPTRGILK-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
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- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
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- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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| TWI252847B (en) * | 2001-07-10 | 2006-04-11 | Synta Pharmaceuticals Corp | Synthesis of taxol enhancers |
| MXPA02010231A (es) * | 2001-11-27 | 2004-12-13 | Warner Lambert Co | Inhibidores aminotransferasa dependientes de aminoacidos de cadena ramificada y su uso en el tratamiento de las enfermedades neurodegenerativas. |
| EP1877048A1 (en) * | 2005-04-15 | 2008-01-16 | Synta Pharmaceuticals Corporation | Combination cancer therapy with bis(thiohydrazide) amide compounds |
| AU2007288338B2 (en) | 2006-08-21 | 2012-05-03 | Synta Pharmaceuticals Corp. | Compounds for treating proliferative disorders |
| WO2008027445A2 (en) * | 2006-08-31 | 2008-03-06 | Synta Pharmaceuticals Corp. | Combination with bis(thiohydrazide amides) for treating cancer |
| US8093425B2 (en) | 2007-04-30 | 2012-01-10 | Synta Pharmaceuticals Corp. | Compounds for treating proliferative disorders |
| TWI490214B (zh) * | 2008-05-30 | 2015-07-01 | 艾德克 上野股份有限公司 | 苯或噻吩衍生物及該等作為ｖａｐ－１抑制劑之用途 |
| US20130331452A1 (en) | 2010-09-08 | 2013-12-12 | Wellstat Therapeutics Corporation | Benzoic acid compounds for reducing uric acid |
| BR112013018212B1 (pt) * | 2011-01-21 | 2021-12-14 | Sun Pharma Advanced Research Company Ltd | Inibidores de tirosino quinase contendo diarilacettleno hidrazida |
| EP2481801A1 (en) * | 2011-01-28 | 2012-08-01 | Deutsches Krebsforschungszentrum | Inhibitors of branched-chain-aminotransferase-1 (BCAT1) for the treatment of neoplasia |
| WO2014049471A1 (en) * | 2012-09-29 | 2014-04-03 | Mahesh Kandula | Compositions and methods for the treatment of ventricular arrhythmias and cardiovascular diseases |
| CN104610104B (zh) * | 2015-02-13 | 2016-06-01 | 佛山市赛维斯医药科技有限公司 | 一种含苯磺酰肼和硝基苯结构gpr119激动剂及其用途 |
| CN104592066B (zh) * | 2015-02-13 | 2016-04-06 | 佛山市赛维斯医药科技有限公司 | 一类苯磺酰肼化合物、制备方法及其用途 |
| CN104649938B (zh) * | 2015-02-13 | 2016-06-01 | 佛山市赛维斯医药科技有限公司 | 硝基苯磺酰肼类gpr119激动剂、制备方法及其用途 |
| CN104592065B (zh) * | 2015-02-13 | 2016-04-06 | 佛山市赛维斯医药科技有限公司 | 卤代苯磺酰肼类gpr119激动剂、制备方法及其用途 |
| CN104649944B (zh) * | 2015-02-13 | 2016-08-31 | 佛山市赛维斯医药科技有限公司 | 一类甲氧苯磺酰肼类gpr119激动剂、制备方法及其用途 |
| CN104610105B (zh) * | 2015-02-13 | 2016-04-06 | 佛山市赛维斯医药科技有限公司 | 烷基取代的苯磺酰肼类gpr119激动剂、制备方法及其用途 |
| CN104610103B (zh) * | 2015-02-13 | 2016-04-06 | 佛山市赛维斯医药科技有限公司 | 含苯磺酰肼和卤代苯结构gpr119激动剂、制备方法及其用途 |
| CN104649937B (zh) * | 2015-02-13 | 2016-04-13 | 佛山市赛维斯医药科技有限公司 | 苯磺酰肼类gpr119激动剂、制备方法及其用途 |
| CN104628612B (zh) * | 2015-02-13 | 2016-06-01 | 佛山市赛维斯医药科技有限公司 | 一类腈基苯磺酰肼类gpr119激动剂、制备方法及其用途 |
| GB201510019D0 (en) * | 2015-06-09 | 2015-07-22 | Cancer Therapeutics Crc Pty Ltd | Compounds |
| CN115715285B (zh) * | 2020-04-27 | 2025-09-09 | 奧土择破利悟 | 作为ubr盒结构域配体的化合物 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69611437T2 (de) * | 1995-02-21 | 2001-08-23 | Nippon Suisan Kaisha, Ltd. | Gluteminsäurerezeptor agonisten |
| FR2792314B1 (fr) * | 1999-04-15 | 2001-06-01 | Adir | Nouveaux composes aminotriazoles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CN1626069A (zh) * | 1999-12-08 | 2005-06-15 | 沃尼尔·朗伯公司 | 支链氨基酸依赖性氨基转移酶的抑制剂及其在治疗糖尿病性视网膜病中的应用 |
| DE60111639T2 (de) * | 2000-09-19 | 2006-04-27 | Warner-Lambert Co. Llc | Hemmer der verzweigten aminosäure-abhängigen aminotransferase und deren verwendung in der behandlung von neurodegenerativen erkrankungen |
| MXPA03004821A (es) * | 2000-11-28 | 2004-03-26 | Guilford Pharm Inc | Compuestos de union de ciclofilina carbociclica bisubstutuida y su uso. |
| MXPA02010231A (es) * | 2001-11-27 | 2004-12-13 | Warner Lambert Co | Inhibidores aminotransferasa dependientes de aminoacidos de cadena ramificada y su uso en el tratamiento de las enfermedades neurodegenerativas. |
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2002
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- 2002-10-22 AU AU2002365311A patent/AU2002365311A1/en not_active Abandoned
- 2002-11-21 EP EP02258017A patent/EP1314723A1/en not_active Withdrawn
- 2002-11-25 CA CA002412466A patent/CA2412466A1/en not_active Abandoned
- 2002-11-26 BR BR0204863-9A patent/BR0204863A/pt not_active IP Right Cessation
- 2002-11-26 US US10/304,803 patent/US6809119B2/en not_active Expired - Fee Related
- 2002-11-27 JP JP2002344313A patent/JP2003206273A/ja active Pending
-
2004
- 2004-05-17 US US10/847,108 patent/US20050014841A1/en not_active Abandoned
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