JP2006522126A5 - - Google Patents
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- Publication number
- JP2006522126A5 JP2006522126A5 JP2006509331A JP2006509331A JP2006522126A5 JP 2006522126 A5 JP2006522126 A5 JP 2006522126A5 JP 2006509331 A JP2006509331 A JP 2006509331A JP 2006509331 A JP2006509331 A JP 2006509331A JP 2006522126 A5 JP2006522126 A5 JP 2006522126A5
- Authority
- JP
- Japan
- Prior art keywords
- sulfonamide
- trifluoro
- thiophene
- compound
- hydroxymethyl
- 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
- 150000001875 compounds Chemical class 0.000 claims 40
- 125000000217 alkyl group Chemical group 0.000 claims 21
- -1 CF 3 Chemical group 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 14
- 229940124530 sulfonamide Drugs 0.000 claims 12
- 238000000034 method Methods 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 239000000651 prodrug Substances 0.000 claims 8
- 229940002612 prodrug Drugs 0.000 claims 8
- KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 239000012024 dehydrating agents Substances 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001010 sulfinic acid amide group Chemical group 0.000 claims 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- IBVWKWXNEQMZMK-UHFFFAOYSA-N [ethyl(propan-2-yloxy)alumanyl]formonitrile Chemical group CC[Al](C#N)OC(C)C IBVWKWXNEQMZMK-UHFFFAOYSA-N 0.000 claims 2
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims 2
- 235000008206 alpha-amino acids Nutrition 0.000 claims 2
- 150000001414 amino alcohols Chemical class 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 150000001993 dienes Chemical class 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- 208000027061 mild cognitive impairment Diseases 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 2
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical group [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- NRIVLCBZUZOJKF-UHFFFAOYSA-N 2,5-dichloro-n-[4,4,4-trifluoro-1-hydroxy-3-(trifluoromethyl)butan-2-yl]thiophene-3-sulfonamide Chemical compound FC(F)(F)C(C(F)(F)F)C(CO)NS(=O)(=O)C=1C=C(Cl)SC=1Cl NRIVLCBZUZOJKF-UHFFFAOYSA-N 0.000 claims 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- HGHZXRLQQGFESX-UHFFFAOYSA-N 4,5-dichloro-n-[4,4,4-trifluoro-1-hydroxy-3-(trifluoromethyl)butan-2-yl]thiophene-2-sulfonamide Chemical compound FC(F)(F)C(C(F)(F)F)C(CO)NS(=O)(=O)C1=CC(Cl)=C(Cl)S1 HGHZXRLQQGFESX-UHFFFAOYSA-N 0.000 claims 1
- BBSVRSHBFYVDCK-UHFFFAOYSA-N 4-bromo-5-chloro-n-[4,4,4-trifluoro-1-hydroxy-3-(trifluoromethyl)butan-2-yl]thiophene-2-sulfonamide Chemical compound FC(F)(F)C(C(F)(F)F)C(CO)NS(=O)(=O)C1=CC(Br)=C(Cl)S1 BBSVRSHBFYVDCK-UHFFFAOYSA-N 0.000 claims 1
- AHOFECNYCWGPAI-UHFFFAOYSA-N 5-bromo-n-[4,4,4-trifluoro-1-hydroxy-3-(trifluoromethyl)butan-2-yl]thiophene-2-sulfonamide Chemical compound FC(F)(F)C(C(F)(F)F)C(CO)NS(=O)(=O)C1=CC=C(Br)S1 AHOFECNYCWGPAI-UHFFFAOYSA-N 0.000 claims 1
- UXPMWBRBKHZFJJ-UHFFFAOYSA-N 5-chloro-3-(4,4,4-trifluoro-1-hydroxybutan-2-yl)thiophene-2-sulfonamide Chemical compound NS(=O)(=O)C=1SC(Cl)=CC=1C(CO)CC(F)(F)F UXPMWBRBKHZFJJ-UHFFFAOYSA-N 0.000 claims 1
- LQGSPEIGWUOCRP-UHFFFAOYSA-N 5-chloro-n-(5,5,5-trifluoro-1-hydroxypentan-2-yl)thiophene-2-sulfonamide Chemical compound FC(F)(F)CCC(CO)NS(=O)(=O)C1=CC=C(Cl)S1 LQGSPEIGWUOCRP-UHFFFAOYSA-N 0.000 claims 1
- AFBDXUUDSFPENN-YUMQZZPRSA-N 5-chloro-n-[(2r,3s)-3-ethyl-5,5,5-trifluoro-1-hydroxypentan-2-yl]thiophene-2-sulfonamide Chemical compound FC(F)(F)C[C@H](CC)[C@H](CO)NS(=O)(=O)C1=CC=C(Cl)S1 AFBDXUUDSFPENN-YUMQZZPRSA-N 0.000 claims 1
- AFBDXUUDSFPENN-HTQZYQBOSA-N 5-chloro-n-[(2s,3r)-3-ethyl-5,5,5-trifluoro-1-hydroxypentan-2-yl]thiophene-2-sulfonamide Chemical compound FC(F)(F)C[C@@H](CC)[C@@H](CO)NS(=O)(=O)C1=CC=C(Cl)S1 AFBDXUUDSFPENN-HTQZYQBOSA-N 0.000 claims 1
- UJIHZLJAUMPTFR-RNFRBKRXSA-N 5-chloro-n-[(2s,3r)-5,5,5-trifluoro-1-hydroxy-3-methylpentan-2-yl]thiophene-2-sulfonamide Chemical compound FC(F)(F)C[C@@H](C)[C@@H](CO)NS(=O)(=O)C1=CC=C(Cl)S1 UJIHZLJAUMPTFR-RNFRBKRXSA-N 0.000 claims 1
- UPRHDMKBKRLMSW-RNFRBKRXSA-N 5-chloro-n-[(2s,3r)-5,5,5-trifluoro-3-methyl-1-oxopentan-2-yl]thiophene-2-sulfonamide Chemical compound FC(F)(F)C[C@@H](C)[C@@H](C=O)NS(=O)(=O)C1=CC=C(Cl)S1 UPRHDMKBKRLMSW-RNFRBKRXSA-N 0.000 claims 1
- NNOMPWLAKDCGCQ-XCBNKYQSSA-N 5-chloro-n-[(3s,4r)-6,6,6-trifluoro-2-hydroxy-2,4-dimethylhexan-3-yl]thiophene-2-sulfonamide Chemical compound FC(F)(F)C[C@@H](C)[C@@H](C(C)(C)O)NS(=O)(=O)C1=CC=C(Cl)S1 NNOMPWLAKDCGCQ-XCBNKYQSSA-N 0.000 claims 1
- FKECWLIGCZXHBY-LDWIPMOCSA-N 5-chloro-n-[(3s,4r)-6,6,6-trifluoro-4-methyl-2-oxohexan-3-yl]thiophene-2-sulfonamide Chemical compound FC(F)(F)C[C@@H](C)[C@@H](C(C)=O)NS(=O)(=O)C1=CC=C(Cl)S1 FKECWLIGCZXHBY-LDWIPMOCSA-N 0.000 claims 1
- HHRPDEFXZGZRDB-UHFFFAOYSA-N 5-chloro-n-[1-(4,4-difluorocyclohexyl)-2-hydroxyethyl]thiophene-2-sulfonamide Chemical compound C1CC(F)(F)CCC1C(CO)NS(=O)(=O)C1=CC=C(Cl)S1 HHRPDEFXZGZRDB-UHFFFAOYSA-N 0.000 claims 1
- OSLDXZJYEORDCF-UHFFFAOYSA-N 5-chloro-n-[1-(6,6-difluoro-3-bicyclo[3.1.0]hexanyl)-2-hydroxyethyl]thiophene-2-sulfonamide Chemical compound C1C(C2(F)F)C2CC1C(CO)NS(=O)(=O)C1=CC=C(Cl)S1 OSLDXZJYEORDCF-UHFFFAOYSA-N 0.000 claims 1
- CJEZEJKUSJGLHH-UHFFFAOYSA-N 5-chloro-n-[5,5,5-trifluoro-1-hydroxy-3-(2,2,2-trifluoroethyl)pentan-2-yl]thiophene-2-sulfonamide Chemical compound FC(F)(F)CC(CC(F)(F)F)C(CO)NS(=O)(=O)C1=CC=C(Cl)S1 CJEZEJKUSJGLHH-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims 1
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims 1
- 206010059245 Angiopathy Diseases 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims 1
- 229910005965 SO 2 Inorganic materials 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 206010044688 Trisomy 21 Diseases 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 206010002022 amyloidosis Diseases 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 208000026106 cerebrovascular disease Diseases 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 201000008319 inclusion body myositis Diseases 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 239000001630 malic acid Substances 0.000 claims 1
- 235000011090 malic acid Nutrition 0.000 claims 1
- 229960002510 mandelic acid Drugs 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 239000002808 molecular sieve Substances 0.000 claims 1
- JRZREWWYEJRTFF-RXMQYKEDSA-N n-[(2s)-4,4,4-trifluoro-1-hydroxy-3-(trifluoromethyl)butan-2-yl]thiophene-2-sulfonamide Chemical compound FC(F)(F)C(C(F)(F)F)[C@@H](CO)NS(=O)(=O)C1=CC=CS1 JRZREWWYEJRTFF-RXMQYKEDSA-N 0.000 claims 1
- QGNNYWYWUIHAIR-ZCFIWIBFSA-N n-[(2s)-4,4,4-trifluoro-1-hydroxy-3-(trifluoromethyl)butan-2-yl]thiophene-3-sulfonamide Chemical compound FC(F)(F)C(C(F)(F)F)[C@@H](CO)NS(=O)(=O)C=1C=CSC=1 QGNNYWYWUIHAIR-ZCFIWIBFSA-N 0.000 claims 1
- NFRHMCWDOSGFLS-UHFFFAOYSA-N n-[4,4,4-trifluoro-1-hydroxy-3-(trifluoromethyl)butan-2-yl]-1-benzothiophene-2-sulfonamide Chemical compound C1=CC=C2SC(S(=O)(=O)NC(CO)C(C(F)(F)F)C(F)(F)F)=CC2=C1 NFRHMCWDOSGFLS-UHFFFAOYSA-N 0.000 claims 1
- JRZREWWYEJRTFF-UHFFFAOYSA-N n-[4,4,4-trifluoro-1-hydroxy-3-(trifluoromethyl)butan-2-yl]thiophene-2-sulfonamide Chemical compound FC(F)(F)C(C(F)(F)F)C(CO)NS(=O)(=O)C1=CC=CS1 JRZREWWYEJRTFF-UHFFFAOYSA-N 0.000 claims 1
- QGNNYWYWUIHAIR-UHFFFAOYSA-N n-[4,4,4-trifluoro-1-hydroxy-3-(trifluoromethyl)butan-2-yl]thiophene-3-sulfonamide Chemical compound FC(F)(F)C(C(F)(F)F)C(CO)NS(=O)(=O)C=1C=CSC=1 QGNNYWYWUIHAIR-UHFFFAOYSA-N 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 208000022256 primary systemic amyloidosis Diseases 0.000 claims 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- CESUXLKAADQNTB-UHFFFAOYSA-N tert-butanesulfinamide Chemical compound CC(C)(C)S(N)=O CESUXLKAADQNTB-UHFFFAOYSA-N 0.000 claims 1
- GUJWNCDSIDXKBJ-UHFFFAOYSA-N CCOC(C(C(C)C(F)(F)F)NC(C)c1ccccc1)=O Chemical compound CCOC(C(C(C)C(F)(F)F)NC(C)c1ccccc1)=O GUJWNCDSIDXKBJ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45922803P | 2003-03-31 | 2003-03-31 | |
| PCT/US2004/009268 WO2004092155A1 (en) | 2003-03-31 | 2004-03-26 | Fluoro-and trifluoroalkyl-containing heterocyclic sulfonamide inhibitors of beta amyloid production and derivatives thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006522126A JP2006522126A (ja) | 2006-09-28 |
| JP2006522126A5 true JP2006522126A5 (https=) | 2009-06-04 |
Family
ID=33299665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006509331A Pending JP2006522126A (ja) | 2003-03-31 | 2004-03-26 | βアミロイド生産のフルオロ含有およびトリフルオロアルキル含有複素環スルホンアミド阻害物質およびその誘導体 |
Country Status (22)
| Country | Link |
|---|---|
| US (3) | US7300951B2 (https=) |
| EP (1) | EP1608638A1 (https=) |
| JP (1) | JP2006522126A (https=) |
| KR (1) | KR20060002908A (https=) |
| CN (2) | CN1780829B (https=) |
| AR (1) | AR043940A1 (https=) |
| AU (1) | AU2004230844B2 (https=) |
| BR (1) | BRPI0408962A (https=) |
| CA (1) | CA2517155A1 (https=) |
| CL (1) | CL2004000647A1 (https=) |
| CO (1) | CO5640049A2 (https=) |
| CR (1) | CR7951A (https=) |
| EC (1) | ECSP056128A (https=) |
| MX (1) | MXPA05010368A (https=) |
| NO (1) | NO20054263L (https=) |
| NZ (1) | NZ542468A (https=) |
| RU (1) | RU2342374C2 (https=) |
| SG (1) | SG167669A1 (https=) |
| TW (1) | TWI336698B (https=) |
| UA (1) | UA82093C2 (https=) |
| WO (1) | WO2004092155A1 (https=) |
| ZA (1) | ZA200507896B (https=) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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2004
- 2004-03-26 KR KR1020057018637A patent/KR20060002908A/ko not_active Ceased
- 2004-03-26 RU RU2005133434/04A patent/RU2342374C2/ru not_active IP Right Cessation
- 2004-03-26 SG SG200708961-8A patent/SG167669A1/en unknown
- 2004-03-26 US US10/810,517 patent/US7300951B2/en not_active Expired - Fee Related
- 2004-03-26 CA CA002517155A patent/CA2517155A1/en not_active Abandoned
- 2004-03-26 JP JP2006509331A patent/JP2006522126A/ja active Pending
- 2004-03-26 UA UAA200510177A patent/UA82093C2/uk unknown
- 2004-03-26 WO PCT/US2004/009268 patent/WO2004092155A1/en not_active Ceased
- 2004-03-26 AR ARP040101022A patent/AR043940A1/es unknown
- 2004-03-26 TW TW093108219A patent/TWI336698B/zh not_active IP Right Cessation
- 2004-03-26 EP EP04758978A patent/EP1608638A1/en not_active Withdrawn
- 2004-03-26 CL CL200400647A patent/CL2004000647A1/es unknown
- 2004-03-26 CN CN2004800087813A patent/CN1780829B/zh not_active Expired - Fee Related
- 2004-03-26 CN CNA2008100013400A patent/CN101274926A/zh active Pending
- 2004-03-26 NZ NZ542468A patent/NZ542468A/en not_active IP Right Cessation
- 2004-03-26 AU AU2004230844A patent/AU2004230844B2/en not_active Expired - Fee Related
- 2004-03-26 BR BRPI0408962-6A patent/BRPI0408962A/pt not_active IP Right Cessation
- 2004-03-26 MX MXPA05010368A patent/MXPA05010368A/es active IP Right Grant
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2005
- 2005-08-19 CR CR7951A patent/CR7951A/es unknown
- 2005-09-15 NO NO20054263A patent/NO20054263L/no not_active Application Discontinuation
- 2005-09-29 ZA ZA200507896A patent/ZA200507896B/en unknown
- 2005-10-26 CO CO05109226A patent/CO5640049A2/es not_active Application Discontinuation
- 2005-10-28 EC EC2005006128A patent/ECSP056128A/es unknown
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2007
- 2007-06-15 US US11/818,630 patent/US7547725B2/en not_active Expired - Fee Related
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- 2009-05-05 US US12/435,442 patent/US7858658B2/en not_active Expired - Fee Related
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