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
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
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| CA (1) | CA2412466A1 (https=) |
| MX (1) | MXPA02010231A (https=) |
| WO (1) | WO2003045902A1 (https=) |
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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. |
| WO2006113695A1 (en) * | 2005-04-15 | 2006-10-26 | Synta Pharmaceuticals Corp. | Combination cancer therapy with bis(thiohydrazide) amide compounds |
| TWI440632B (zh) | 2006-08-21 | 2014-06-11 | Synta Pharmaceuticals Corp | 用於治療增生性疾病的化合物 |
| JP2010502616A (ja) * | 2006-08-31 | 2010-01-28 | シンタ ファーマシューティカルズ コーポレーション | 癌を治療するためのビス（チオヒドラジドアミド）の組み合わせ |
| 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 |
| WO2012033720A1 (en) | 2010-09-08 | 2012-03-15 | Wellstat Therapeutics Corporation | Benzoic acid compounds for reducing uric acid |
| CN103502217B (zh) * | 2011-01-21 | 2015-11-25 | 太阳医药高级研究有限公司 | 包含酪氨酸激酶抑制剂的二芳基乙炔酰肼 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| GB201510019D0 (en) * | 2015-06-09 | 2015-07-22 | Cancer Therapeutics Crc Pty Ltd | Compounds |
| WO2021221444A1 (ko) * | 2020-04-27 | 2021-11-04 | 주식회사 오토텍바이오 | Ubr 박스 도메인 리간드로의 화합물 |
Family Cites Families (6)
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| KR19980702372A (ko) * | 1995-02-21 | 1998-07-15 | 구니이 야쓰오 | 글루타민산 수용체 작용약 |
| FR2792314B1 (fr) * | 1999-04-15 | 2001-06-01 | Adir | Nouveaux composes aminotriazoles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| WO2001042191A1 (en) * | 1999-12-08 | 2001-06-14 | Warner-Lambert Company | Branched chain amino acid-dependent aminotransferase inhibitors and their use in the treatment of diabetic retinopathy |
| WO2002024672A2 (en) * | 2000-09-19 | 2002-03-28 | Warner-Lambert Company Llc | Branched chain amino acid-dependent aminotransferase inhibitors and their use in the treatment of neurodegenerative diseases |
| CA2430409A1 (en) * | 2000-11-28 | 2002-06-06 | Guilford Pharmaceuticals Inc. | Bisubstituted carbocyclic cyclophilin binding compounds and their use |
| 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 WO PCT/IB2002/004386 patent/WO2003045902A1/en not_active Ceased
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- 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 US US10/304,803 patent/US6809119B2/en not_active Expired - Fee Related
- 2002-11-26 BR BR0204863-9A patent/BR0204863A/pt not_active IP Right Cessation
- 2002-11-27 JP JP2002344313A patent/JP2003206273A/ja active Pending
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