JP2002537376A - 新規スルホンアミドおよびそれらの使用 - Google Patents
新規スルホンアミドおよびそれらの使用Info
- Publication number
- JP2002537376A JP2002537376A JP2000600975A JP2000600975A JP2002537376A JP 2002537376 A JP2002537376 A JP 2002537376A JP 2000600975 A JP2000600975 A JP 2000600975A JP 2000600975 A JP2000600975 A JP 2000600975A JP 2002537376 A JP2002537376 A JP 2002537376A
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- benzenesulfonamide
- substituted
- dichlorophenyl
- unsubstituted
- 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
Links
- 229940124530 sulfonamide Drugs 0.000 title claims abstract description 33
- 150000003456 sulfonamides Chemical class 0.000 title claims description 17
- -1 sulfonamide compounds Chemical class 0.000 claims abstract description 673
- 150000001875 compounds Chemical class 0.000 claims abstract description 169
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 152
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 37
- 150000001408 amides Chemical class 0.000 claims abstract description 35
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 34
- 201000010099 disease Diseases 0.000 claims abstract description 27
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 27
- 150000002148 esters Chemical class 0.000 claims abstract description 22
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 22
- 150000002367 halogens Chemical class 0.000 claims abstract description 22
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 9
- 125000005864 sulfonamidyl group Chemical group 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 187
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 146
- 238000000034 method Methods 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 102100022704 Amyloid-beta precursor protein Human genes 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 125000004122 cyclic group Chemical group 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 208000024827 Alzheimer disease Diseases 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 108090000623 proteins and genes Proteins 0.000 claims description 9
- 102000004169 proteins and genes Human genes 0.000 claims description 8
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 101000823051 Homo sapiens Amyloid-beta precursor protein Proteins 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 150000007942 carboxylates Chemical class 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 206010059245 Angiopathy Diseases 0.000 claims description 2
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims description 2
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims description 2
- 201000010374 Down Syndrome Diseases 0.000 claims description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 2
- 206010044688 Trisomy 21 Diseases 0.000 claims description 2
- 206010002022 amyloidosis Diseases 0.000 claims description 2
- 201000008319 inclusion body myositis Diseases 0.000 claims description 2
- 208000022256 primary systemic amyloidosis Diseases 0.000 claims description 2
- 108010079054 Amyloid beta-Protein Precursor Proteins 0.000 claims 7
- 102000018430 Amyloid-beta precursor proteins Human genes 0.000 claims 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 108010090849 Amyloid beta-Peptides Proteins 0.000 abstract description 18
- 102000013455 Amyloid beta-Peptides Human genes 0.000 abstract description 18
- 238000011282 treatment Methods 0.000 abstract description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 6
- 125000000565 sulfonamide group Chemical group 0.000 abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 abstract description 5
- 150000004657 carbamic acid derivatives Chemical class 0.000 abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
- 125000004434 sulfur atom Chemical group 0.000 abstract description 3
- 230000002265 prevention Effects 0.000 abstract description 2
- 239000011593 sulfur Substances 0.000 abstract description 2
- 150000002170 ethers Chemical class 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 523
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 472
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 337
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 233
- 239000000243 solution Substances 0.000 description 223
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 168
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 130
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 120
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 118
- 239000000460 chlorine Substances 0.000 description 115
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 115
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 113
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 105
- 230000002829 reductive effect Effects 0.000 description 104
- 239000003921 oil Substances 0.000 description 103
- 235000019198 oils Nutrition 0.000 description 103
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 102
- 239000011541 reaction mixture Substances 0.000 description 94
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 85
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 77
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 74
- 239000012141 concentrate Substances 0.000 description 71
- 235000008504 concentrate Nutrition 0.000 description 71
- 239000011734 sodium Substances 0.000 description 69
- 239000000047 product Substances 0.000 description 66
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 61
- 238000010898 silica gel chromatography Methods 0.000 description 61
- 239000002904 solvent Substances 0.000 description 58
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 57
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 54
- 239000012230 colorless oil Substances 0.000 description 54
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 52
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
- 101100441092 Danio rerio crlf3 gene Proteins 0.000 description 48
- 239000007787 solid Substances 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 44
- 238000003756 stirring Methods 0.000 description 44
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 43
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 37
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 34
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 101710137189 Amyloid-beta A4 protein Proteins 0.000 description 32
- 101710151993 Amyloid-beta precursor protein Proteins 0.000 description 32
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 32
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 30
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 30
- PWQOZRPSDQKNPW-UHFFFAOYSA-N pentane-1-sulfonyl chloride Chemical compound CCCCCS(Cl)(=O)=O PWQOZRPSDQKNPW-UHFFFAOYSA-N 0.000 description 29
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- DZHSAHHDTRWUTF-SIQRNXPUSA-N amyloid-beta polypeptide 42 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(C)C)C1=CC=CC=C1 DZHSAHHDTRWUTF-SIQRNXPUSA-N 0.000 description 26
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 26
- 238000004587 chromatography analysis Methods 0.000 description 26
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 26
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 25
- 229920005557 bromobutyl Polymers 0.000 description 24
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 24
- 239000012043 crude product Substances 0.000 description 23
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- 229920006395 saturated elastomer Polymers 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 239000012267 brine Substances 0.000 description 20
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 20
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 19
- FFIJCJSWZIZNKE-CYBMUJFWSA-N 4-chloro-n-(2,5-dichlorophenyl)-n-[(2r)-5-(methylsulfamoyl)pentan-2-yl]benzenesulfonamide Chemical compound C=1C=C(Cl)C=CC=1S(=O)(=O)N([C@H](C)CCCS(=O)(=O)NC)C1=CC(Cl)=CC=C1Cl FFIJCJSWZIZNKE-CYBMUJFWSA-N 0.000 description 18
- OWCDMRFUFMERMZ-UHFFFAOYSA-N benzenesulfonamide;hydrochloride Chemical compound Cl.NS(=O)(=O)C1=CC=CC=C1 OWCDMRFUFMERMZ-UHFFFAOYSA-N 0.000 description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 18
- 229910052786 argon Inorganic materials 0.000 description 17
- 239000000284 extract Substances 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 229940086542 triethylamine Drugs 0.000 description 17
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 16
- 229910004298 SiO 2 Inorganic materials 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 15
- 239000012299 nitrogen atmosphere Substances 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 13
- LBGPSXJEOBSNME-LLVKDONJSA-N n-[(2r)-4-bromobutan-2-yl]-4-chloro-n-(2,5-dichlorophenyl)benzenesulfonamide Chemical compound C=1C=C(Cl)C=CC=1S(=O)(=O)N([C@@H](CCBr)C)C1=CC(Cl)=CC=C1Cl LBGPSXJEOBSNME-LLVKDONJSA-N 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 13
- 239000011780 sodium chloride Substances 0.000 description 13
- OGTCASXNYSJOMS-MRXNPFEDSA-N 4-chloro-n-(2,5-dichlorophenyl)-n-[(2r)-5-thiomorpholin-4-ylsulfonylpentan-2-yl]benzenesulfonamide Chemical compound C([C@@H](C)N(C=1C(=CC=C(Cl)C=1)Cl)S(=O)(=O)C=1C=CC(Cl)=CC=1)CCS(=O)(=O)N1CCSCC1 OGTCASXNYSJOMS-MRXNPFEDSA-N 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- WDODZTDUEFGRHC-DIAVIDTQSA-N 4-chloro-n-(2,5-dichlorophenyl)-n-[(2r)-4-[2-(methylsulfonylmethyl)piperidin-1-yl]butan-2-yl]benzenesulfonamide Chemical compound C([C@@H](C)N(C=1C(=CC=C(Cl)C=1)Cl)S(=O)(=O)C=1C=CC(Cl)=CC=1)CN1CCCCC1CS(C)(=O)=O WDODZTDUEFGRHC-DIAVIDTQSA-N 0.000 description 11
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 11
- 239000012280 lithium aluminium hydride Substances 0.000 description 11
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- 239000006188 syrup Substances 0.000 description 11
- 235000020357 syrup Nutrition 0.000 description 11
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 10
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 10
- RJQRCOMHVBLQIH-UHFFFAOYSA-N pentane-1-sulfonic acid Chemical compound CCCCCS(O)(=O)=O RJQRCOMHVBLQIH-UHFFFAOYSA-N 0.000 description 10
- 125000006308 propyl amino group Chemical group 0.000 description 10
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
- 238000007792 addition Methods 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000012458 free base Substances 0.000 description 9
- QHYCEJFAEPUVGN-GFCCVEGCSA-N n-[(2r)-5-bromopentan-2-yl]-4-chloro-n-(2,5-dichlorophenyl)benzenesulfonamide Chemical compound C=1C=C(Cl)C=CC=1S(=O)(=O)N([C@@H](CCCBr)C)C1=CC(Cl)=CC=C1Cl QHYCEJFAEPUVGN-GFCCVEGCSA-N 0.000 description 9
- PCCHDLKZJSXRPO-CYBMUJFWSA-N n-[(4r)-4-(2,5-dichloro-n-(4-chlorophenyl)sulfonylanilino)pentyl]acetamide Chemical compound C=1C=C(Cl)C=CC=1S(=O)(=O)N([C@@H](CCCNC(C)=O)C)C1=CC(Cl)=CC=C1Cl PCCHDLKZJSXRPO-CYBMUJFWSA-N 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 9
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- 125000004450 alkenylene group Chemical group 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 8
- 125000000732 arylene group Chemical group 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 230000014759 maintenance of location Effects 0.000 description 8
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 7
- 208000035475 disorder Diseases 0.000 description 7
- 239000006260 foam Substances 0.000 description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
- 229940017219 methyl propionate Drugs 0.000 description 7
- RITXDDVKINVBQR-GFCCVEGCSA-N n-[(2r)-5-bromopentan-2-yl]-4-chloro-n-(5-chloro-2-fluorophenyl)benzenesulfonamide Chemical compound C=1C=C(Cl)C=CC=1S(=O)(=O)N([C@@H](CCCBr)C)C1=CC(Cl)=CC=C1F RITXDDVKINVBQR-GFCCVEGCSA-N 0.000 description 7
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
- 238000007429 general method Methods 0.000 description 6
- 150000003840 hydrochlorides Chemical class 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
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- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
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- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
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- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
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- 125000004076 pyridyl group Chemical group 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000003127 radioimmunoassay Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- ORKNJSZJUXOALS-UHFFFAOYSA-N s-[3-[2-[(n-(4-chlorophenyl)sulfonylanilino)methyl]phenoxy]propyl] ethanethioate Chemical compound CC(=O)SCCCOC1=CC=CC=C1CN(S(=O)(=O)C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ORKNJSZJUXOALS-UHFFFAOYSA-N 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 description 1
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- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
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- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
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- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
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- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
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- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
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- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
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- 230000002459 sustained effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229940033134 talc Drugs 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- NNCPMJHKYIRKSA-VIFPVBQESA-N tert-butyl (2s)-2-acetylpyrrolidine-1-carboxylate Chemical compound CC(=O)[C@@H]1CCCN1C(=O)OC(C)(C)C NNCPMJHKYIRKSA-VIFPVBQESA-N 0.000 description 1
- DZAWMCLRNISWMD-BQYQJAHWSA-N tert-butyl (e)-hex-2-enoate Chemical compound CCC\C=C\C(=O)OC(C)(C)C DZAWMCLRNISWMD-BQYQJAHWSA-N 0.000 description 1
- ZUODPLYFAPSMRX-UHFFFAOYSA-N tert-butyl 4-[3-[2-[(n-(4-chlorophenyl)sulfonylanilino)methyl]phenoxy]propyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CCCOC1=CC=CC=C1CN(S(=O)(=O)C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZUODPLYFAPSMRX-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003527 tetrahydropyrans Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 201000008148 visual agnosia Diseases 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
-
- 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
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/40—Y being a hydrogen or a carbon atom
- C07C323/41—Y being a hydrogen or an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
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Applications Claiming Priority (11)
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| US13099599P | 1999-04-23 | 1999-04-23 | |
| US60/130,995 | 1999-04-23 | ||
| US60/130,994 | 1999-04-23 | ||
| PCT/US2000/004560 WO2000050391A1 (en) | 1999-02-26 | 2000-02-22 | Novel sulfonamide compounds and uses thereof |
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| JP2002537376A true JP2002537376A (ja) | 2002-11-05 |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001026506A (ja) * | 1999-04-28 | 2001-01-30 | Takeda Chem Ind Ltd | スルホンアミド誘導体 |
| JP2007512242A (ja) * | 2003-10-29 | 2007-05-17 | イーラン ファーマスーティカルズ、インコーポレイテッド | N−置換ベンゼンスルホンアミド |
| JP2007516939A (ja) * | 2003-06-23 | 2007-06-28 | ニューロケム (インターナショナル) リミテッド | アミロイド関連疾患を治療するための方法および組成物 |
| JP2007528405A (ja) * | 2004-03-11 | 2007-10-11 | イーラン ファーマスーティカルズ、インコーポレイテッド | N−置換ベンゼンスルホンアミド |
| JP2009533016A (ja) * | 2006-02-06 | 2009-09-17 | イーラン ファーマスーティカルズ、インコーポレイテッド | プレセニリン1特異的阻害剤及びそれらの使用 |
| JP2011523633A (ja) * | 2008-05-08 | 2011-08-18 | ブリストル−マイヤーズ スクイブ カンパニー | 2−アリールグリシンアミド誘導体 |
| JP2015517981A (ja) * | 2012-02-29 | 2015-06-25 | バルーク エス.ブルームバーグ インスティテュート | B型肝炎ウイルス共有結合閉環状dna形成の阻害剤およびそれらの使用方法 |
Families Citing this family (91)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6586617B1 (en) | 1999-04-28 | 2003-07-01 | Sumitomo Chemical Takeda Agro Company, Limited | Sulfonamide derivatives |
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| US5624937A (en) * | 1995-03-02 | 1997-04-29 | Eli Lilly And Company | Chemical compounds as inhibitors of amyloid beta protein production |
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| CZ16899A3 (cs) * | 1996-07-22 | 1999-08-11 | Monsanto Company | Thiolsulfonamidové inhibitory metaloproteázy |
| US5985930A (en) * | 1996-11-21 | 1999-11-16 | Pasinetti; Giulio M. | Treatment of neurodegenerative conditions with nimesulide |
| US5981168A (en) * | 1998-05-15 | 1999-11-09 | The University Of British Columbia | Method and composition for modulating amyloidosis |
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2000
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- 2000-02-22 HU HU0201020A patent/HUP0201020A3/hu unknown
- 2000-02-22 CZ CZ20013000A patent/CZ20013000A3/cs unknown
- 2000-02-22 MX MXPA01008606A patent/MXPA01008606A/es unknown
- 2000-02-22 JP JP2000600975A patent/JP2002537376A/ja active Pending
- 2000-02-22 EP EP00910293A patent/EP1159263A1/en not_active Withdrawn
- 2000-02-22 KR KR1020017010917A patent/KR20020006626A/ko not_active Ceased
- 2000-02-22 CA CA002366919A patent/CA2366919A1/en not_active Abandoned
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- 2000-02-28 UY UY26042A patent/UY26042A1/es not_active Application Discontinuation
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2001026506A (ja) * | 1999-04-28 | 2001-01-30 | Takeda Chem Ind Ltd | スルホンアミド誘導体 |
| JP2007516939A (ja) * | 2003-06-23 | 2007-06-28 | ニューロケム (インターナショナル) リミテッド | アミロイド関連疾患を治療するための方法および組成物 |
| JP2007516938A (ja) * | 2003-06-23 | 2007-06-28 | ニューロケム (インターナショナル) リミテッド | アミロイド関連疾患を治療するための方法および組成物 |
| JP2007512242A (ja) * | 2003-10-29 | 2007-05-17 | イーラン ファーマスーティカルズ、インコーポレイテッド | N−置換ベンゼンスルホンアミド |
| JP2007528405A (ja) * | 2004-03-11 | 2007-10-11 | イーラン ファーマスーティカルズ、インコーポレイテッド | N−置換ベンゼンスルホンアミド |
| US8193389B2 (en) | 2004-03-11 | 2012-06-05 | Elan Pharmaceuticals, Inc. | N-substituted benzene sulfonamides |
| JP2009533016A (ja) * | 2006-02-06 | 2009-09-17 | イーラン ファーマスーティカルズ、インコーポレイテッド | プレセニリン1特異的阻害剤及びそれらの使用 |
| JP2011523633A (ja) * | 2008-05-08 | 2011-08-18 | ブリストル−マイヤーズ スクイブ カンパニー | 2−アリールグリシンアミド誘導体 |
| JP2015517981A (ja) * | 2012-02-29 | 2015-06-25 | バルーク エス.ブルームバーグ インスティテュート | B型肝炎ウイルス共有結合閉環状dna形成の阻害剤およびそれらの使用方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ514453A (en) | 2003-04-29 |
| BR0008965A (pt) | 2002-02-26 |
| AU3241000A (en) | 2000-09-14 |
| NO20014135L (no) | 2001-09-27 |
| HUP0201020A2 (hu) | 2002-07-29 |
| MXPA01008606A (es) | 2003-05-05 |
| KR20020006626A (ko) | 2002-01-23 |
| PL349781A1 (en) | 2002-09-09 |
| HUP0201020A3 (en) | 2003-04-28 |
| EP1159263A1 (en) | 2001-12-05 |
| US6967196B1 (en) | 2005-11-22 |
| CN1348442A (zh) | 2002-05-08 |
| CZ20013000A3 (cs) | 2002-02-13 |
| CA2366919A1 (en) | 2000-08-31 |
| AU773273B2 (en) | 2004-05-20 |
| UY26042A1 (es) | 2000-10-31 |
| PE20001542A1 (es) | 2001-01-08 |
| NO20014135D0 (no) | 2001-08-24 |
| WO2000050391A1 (en) | 2000-08-31 |
| IL144781A0 (en) | 2002-06-30 |
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