UA73540C2 - Diarylcarboxamides - Google Patents

Diarylcarboxamides Download PDF

Info

Publication number: UA73540C2
Authority: UA; Ukraine
Prior art keywords: azadicyclo; carboxamide; 2oct; oct; thiophene
Prior art date: 2000-02-18

Application number

UA2002075475A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Astrazeneca Ab

Priority date (The priority date 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 date listed.)

2000-02-18

Filing date

2001-02-15

Publication date

2005-08-15

2001-02-15 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2005-08-15 Publication of UA73540C2 publication Critical patent/UA73540C2/uk

Links

150000001875 compounds Chemical class 0.000 claims abstract description 341
238000000034 method Methods 0.000 claims abstract description 96
150000003839 salts Chemical class 0.000 claims abstract description 54
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 52
125000003118 aryl group Chemical group 0.000 claims abstract description 45
125000001424 substituent group Chemical group 0.000 claims abstract description 45
229910052717 sulfur Inorganic materials 0.000 claims abstract description 43
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 42
125000004434 sulfur atom Chemical group 0.000 claims abstract description 34
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 28
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 28
229910052760 oxygen Inorganic materials 0.000 claims abstract description 22
239000001301 oxygen Substances 0.000 claims abstract description 22
238000011282 treatment Methods 0.000 claims abstract description 19
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
239000011593 sulfur Substances 0.000 claims abstract description 14
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
238000002560 therapeutic procedure Methods 0.000 claims abstract description 3
208000028017 Psychotic disease Diseases 0.000 claims abstract 3
230000006735 deficit Effects 0.000 claims abstract 3
238000006243 chemical reaction Methods 0.000 claims description 105
-1 с Е - a simple bond Substances 0.000 claims description 76
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 63
239000002904 solvent Substances 0.000 claims description 63
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims description 47
125000005843 halogen group Chemical group 0.000 claims description 41
TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 0.000 claims description 37
239000003054 catalyst Substances 0.000 claims description 32
MTEMDMUNZYLWSQ-UHFFFAOYSA-N 5-bromothiophene-2-carboxamide Chemical compound NC(=O)C1=CC=C(Br)S1 MTEMDMUNZYLWSQ-UHFFFAOYSA-N 0.000 claims description 27
125000002524 organometallic group Chemical group 0.000 claims description 24
VFDAOWISEQYGIF-UHFFFAOYSA-N 5-bromofuran-2-carboxamide Chemical compound NC(=O)C1=CC=C(Br)O1 VFDAOWISEQYGIF-UHFFFAOYSA-N 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 22
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 18
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
ODJFDWIECLJWSR-UHFFFAOYSA-N 3-bromobenzamide Chemical compound NC(=O)C1=CC=CC(Br)=C1 ODJFDWIECLJWSR-UHFFFAOYSA-N 0.000 claims description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
RNEUTTPQDZEDSM-UHFFFAOYSA-N 5-pyridin-4-ylthiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC=C1C1=CC=NC=C1 RNEUTTPQDZEDSM-UHFFFAOYSA-N 0.000 claims description 15
BPSZHKPVINNIBN-UHFFFAOYSA-N 5-pyridin-2-ylthiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC=C1C1=CC=CC=N1 BPSZHKPVINNIBN-UHFFFAOYSA-N 0.000 claims description 14
230000002265 prevention Effects 0.000 claims description 13
OYSOOLCZEMWVQN-UHFFFAOYSA-N 5-phenylthiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC=C1C1=CC=CC=C1 OYSOOLCZEMWVQN-UHFFFAOYSA-N 0.000 claims description 12
VRFAIAYLYPXSPL-UHFFFAOYSA-N 5-pyridin-3-ylthiophene-2-carboxamide Chemical compound NC(=O)C1=CC=C(S1)C1=CC=CN=C1 VRFAIAYLYPXSPL-UHFFFAOYSA-N 0.000 claims description 12
WPIFYCRDSOUHLT-UHFFFAOYSA-N 4-bromothiophene-2-carboxamide Chemical compound NC(=O)C1=CC(Br)=CS1 WPIFYCRDSOUHLT-UHFFFAOYSA-N 0.000 claims description 10
CUZHIOCSRQUJIM-UHFFFAOYSA-N 5-(3-aminophenyl)furan-2-carboxamide Chemical compound O1C(C(=O)N)=CC=C1C1=CC=CC(N)=C1 CUZHIOCSRQUJIM-UHFFFAOYSA-N 0.000 claims description 10
XQIJQYLQZPHQDF-UHFFFAOYSA-N 5-(3-aminophenyl)thiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC=C1C1=CC=CC(N)=C1 XQIJQYLQZPHQDF-UHFFFAOYSA-N 0.000 claims description 10
208000035475 disorder Diseases 0.000 claims description 10
XGFFLSZDZDPBAB-UHFFFAOYSA-N 4-phenylthiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC(C=2C=CC=CC=2)=C1 XGFFLSZDZDPBAB-UHFFFAOYSA-N 0.000 claims description 9
HVUMTDUVKSHFTQ-UHFFFAOYSA-N 5-(3-fluorophenyl)furan-2-carboxamide Chemical compound O1C(C(=O)N)=CC=C1C1=CC=CC(F)=C1 HVUMTDUVKSHFTQ-UHFFFAOYSA-N 0.000 claims description 9
LQSYOLVFFWKQRW-UHFFFAOYSA-N 5-(3-hydroxyphenyl)thiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC=C1C1=CC=CC(O)=C1 LQSYOLVFFWKQRW-UHFFFAOYSA-N 0.000 claims description 9
SSKSCYLZSWSPFB-UHFFFAOYSA-N 5-phenoxythiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC=C1OC1=CC=CC=C1 SSKSCYLZSWSPFB-UHFFFAOYSA-N 0.000 claims description 9
ZGFUHODXXVNYPE-UHFFFAOYSA-N 5-pyridin-4-ylfuran-2-carboxamide Chemical compound O1C(C(=O)N)=CC=C1C1=CC=NC=C1 ZGFUHODXXVNYPE-UHFFFAOYSA-N 0.000 claims description 9
AQEWVBMTXAOMMP-UHFFFAOYSA-N 5-(3-chlorophenyl)furan-2-carboxamide Chemical compound O1C(C(=O)N)=CC=C1C1=CC=CC(Cl)=C1 AQEWVBMTXAOMMP-UHFFFAOYSA-N 0.000 claims description 8
ZTOXUTFUEKVQNM-UHFFFAOYSA-N 5-(3-cyanophenyl)thiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC=C1C1=CC=CC(C#N)=C1 ZTOXUTFUEKVQNM-UHFFFAOYSA-N 0.000 claims description 8
GFHNPIHLDMSUBY-UHFFFAOYSA-N 5-(3-methoxyphenyl)furan-2-carboxamide Chemical compound COC1=CC=CC(C=2OC(=CC=2)C(N)=O)=C1 GFHNPIHLDMSUBY-UHFFFAOYSA-N 0.000 claims description 8
VAUBKXFQQWAVRK-UHFFFAOYSA-N 5-(3-methoxyphenyl)thiophene-2-carboxamide Chemical compound COC1=CC=CC(C=2SC(=CC=2)C(N)=O)=C1 VAUBKXFQQWAVRK-UHFFFAOYSA-N 0.000 claims description 8
FPASADMLLORPAS-UHFFFAOYSA-N 5-(3-nitrophenyl)furan-2-carboxamide Chemical compound O1C(C(=O)N)=CC=C1C1=CC=CC([N+]([O-])=O)=C1 FPASADMLLORPAS-UHFFFAOYSA-N 0.000 claims description 8
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims description 8
108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims description 8
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
IYZIARNSXPGYSC-UHFFFAOYSA-N 3-phenylbenzamide Chemical compound NC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1 IYZIARNSXPGYSC-UHFFFAOYSA-N 0.000 claims description 7
JSGZVMJYZDEIMK-UHFFFAOYSA-N 3-thiophen-2-ylbenzamide Chemical compound NC(=O)C1=CC=CC(C=2SC=CC=2)=C1 JSGZVMJYZDEIMK-UHFFFAOYSA-N 0.000 claims description 7
IKYXIRYASVGYQY-UHFFFAOYSA-N 3-thiophen-3-ylbenzamide Chemical compound NC(=O)C1=CC=CC(C2=CSC=C2)=C1 IKYXIRYASVGYQY-UHFFFAOYSA-N 0.000 claims description 7
WPUVZBOKXQAGDD-UHFFFAOYSA-N 4-pyridin-2-ylthiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC(C=2N=CC=CC=2)=C1 WPUVZBOKXQAGDD-UHFFFAOYSA-N 0.000 claims description 7
XPWHBVLUZBCMJY-UHFFFAOYSA-N 5-(3-fluorophenyl)thiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC=C1C1=CC=CC(F)=C1 XPWHBVLUZBCMJY-UHFFFAOYSA-N 0.000 claims description 7
RQJWFHRUPTYLOV-UHFFFAOYSA-N 5-(3-methylphenyl)furan-2-carboxamide Chemical compound CC1=CC=CC(C=2OC(=CC=2)C(N)=O)=C1 RQJWFHRUPTYLOV-UHFFFAOYSA-N 0.000 claims description 7
XTPWJBLYVBMEQX-UHFFFAOYSA-N 5-(4-chlorophenyl)furan-2-carboxamide Chemical compound O1C(C(=O)N)=CC=C1C1=CC=C(Cl)C=C1 XTPWJBLYVBMEQX-UHFFFAOYSA-N 0.000 claims description 7
ISXKVVQBTQEGSI-UHFFFAOYSA-N 5-bromothiophene-3-carboxamide Chemical compound NC(=O)C1=CSC(Br)=C1 ISXKVVQBTQEGSI-UHFFFAOYSA-N 0.000 claims description 7
ZNMIEYHOIRLLES-UHFFFAOYSA-N 5-phenylfuran-2-carboxamide Chemical compound O1C(C(=O)N)=CC=C1C1=CC=CC=C1 ZNMIEYHOIRLLES-UHFFFAOYSA-N 0.000 claims description 7
UBPRKNMUSICIJU-UHFFFAOYSA-N 5-phenylthiophene-3-carboxamide Chemical compound NC(=O)C1=CSC(C=2C=CC=CC=2)=C1 UBPRKNMUSICIJU-UHFFFAOYSA-N 0.000 claims description 7
ATGPTPLKBWEAHY-UHFFFAOYSA-N 5-pyridin-2-ylfuran-2-carboxamide Chemical compound O1C(C(=O)N)=CC=C1C1=CC=CC=N1 ATGPTPLKBWEAHY-UHFFFAOYSA-N 0.000 claims description 7
NKFWFTVSUZXGPR-UHFFFAOYSA-N 5-quinolin-8-ylthiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC=C1C1=CC=CC2=CC=CN=C12 NKFWFTVSUZXGPR-UHFFFAOYSA-N 0.000 claims description 7
ATWKRIBDUUNNBP-UHFFFAOYSA-N 5-thiophen-2-ylfuran-2-carboxamide Chemical compound O1C(C(=O)N)=CC=C1C1=CC=CS1 ATWKRIBDUUNNBP-UHFFFAOYSA-N 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 7
125000002541 furyl group Chemical group 0.000 claims description 7
229910052740 iodine Inorganic materials 0.000 claims description 7
BZFMDQZSQUUFQS-UHFFFAOYSA-N 5-(3-formylphenyl)thiophene-2-carboxamide Chemical compound C(=O)C=1C=C(C=CC1)C1=CC=C(S1)C(=O)N BZFMDQZSQUUFQS-UHFFFAOYSA-N 0.000 claims description 6
OAOATAYWBZYYQT-UHFFFAOYSA-N 5-(3-morpholin-4-ylphenyl)thiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC=C1C1=CC=CC(N2CCOCC2)=C1 OAOATAYWBZYYQT-UHFFFAOYSA-N 0.000 claims description 6
VZXAJUCWNRKHTL-UHFFFAOYSA-N 5-(4-fluorophenyl)furan-2-carboxamide Chemical compound O1C(C(=O)N)=CC=C1C1=CC=C(F)C=C1 VZXAJUCWNRKHTL-UHFFFAOYSA-N 0.000 claims description 6
WSGWUJLNZBHRGP-UHFFFAOYSA-N 5-(furan-3-yl)furan-2-carboxamide Chemical compound NC(=O)C1=CC=C(O1)C1=COC=C1 WSGWUJLNZBHRGP-UHFFFAOYSA-N 0.000 claims description 6
URUCYJBBOOKHKF-UHFFFAOYSA-N 5-naphthalen-2-ylfuran-2-carboxamide Chemical compound O1C(C(=O)N)=CC=C1C1=CC=C(C=CC=C2)C2=C1 URUCYJBBOOKHKF-UHFFFAOYSA-N 0.000 claims description 6
NPNGQMHTVOFXLB-UHFFFAOYSA-N 5-pyridin-3-ylthiophene-3-carboxamide Chemical compound NC(=O)C1=CSC(C=2C=NC=CC=2)=C1 NPNGQMHTVOFXLB-UHFFFAOYSA-N 0.000 claims description 6
125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 6
150000003857 carboxamides Chemical class 0.000 claims description 6
238000004651 near-field scanning optical microscopy Methods 0.000 claims description 6
229960002715 nicotine Drugs 0.000 claims description 6
VRECCXHVXUPDQT-UHFFFAOYSA-N 3-(2-methoxyphenyl)benzamide Chemical compound COC1=CC=CC=C1C1=CC=CC(C(N)=O)=C1 VRECCXHVXUPDQT-UHFFFAOYSA-N 0.000 claims description 5
WPAVZFKFZGIJKZ-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C(Cl)C=C(Cl)C=2)=C1 WPAVZFKFZGIJKZ-UHFFFAOYSA-N 0.000 claims description 5
SNALSZMAYDWAJA-UHFFFAOYSA-N 3-(3-fluorophenyl)benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C(F)C=CC=2)=C1 SNALSZMAYDWAJA-UHFFFAOYSA-N 0.000 claims description 5
XOHZBPMRSYEDHU-UHFFFAOYSA-N 3-(3-methoxyphenyl)benzamide Chemical compound COC1=CC=CC(C=2C=C(C=CC=2)C(N)=O)=C1 XOHZBPMRSYEDHU-UHFFFAOYSA-N 0.000 claims description 5
HEMYUAPEXJWFCP-UHFFFAOYSA-N 3-iodobenzamide Chemical compound NC(=O)C1=CC=CC(I)=C1 HEMYUAPEXJWFCP-UHFFFAOYSA-N 0.000 claims description 5
ZRWNRAJCPNLYAK-UHFFFAOYSA-N 4-bromobenzamide Chemical compound NC(=O)C1=CC=C(Br)C=C1 ZRWNRAJCPNLYAK-UHFFFAOYSA-N 0.000 claims description 5
XRNBLQCAFWFFPM-UHFFFAOYSA-N 4-iodobenzamide Chemical compound NC(=O)C1=CC=C(I)C=C1 XRNBLQCAFWFFPM-UHFFFAOYSA-N 0.000 claims description 5
AUKQSEGRTKMGAY-UHFFFAOYSA-N 4-pyridin-4-ylthiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC(C=2C=CN=CC=2)=C1 AUKQSEGRTKMGAY-UHFFFAOYSA-N 0.000 claims description 5
WPCSAIACUYFJIQ-UHFFFAOYSA-N 5-(2-methoxyphenyl)furan-2-carboxamide Chemical compound COC1=CC=CC=C1C1=CC=C(C(N)=O)O1 WPCSAIACUYFJIQ-UHFFFAOYSA-N 0.000 claims description 5
HXAZDQRPOGHRHW-UHFFFAOYSA-N 5-(3,5-dimethyl-1,2-oxazol-4-yl)thiophene-2-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC=C(C(N)=O)S1 HXAZDQRPOGHRHW-UHFFFAOYSA-N 0.000 claims description 5
WUWQWRVEZNAWQX-UHFFFAOYSA-N 5-thiophen-3-ylfuran-2-carboxamide Chemical compound O1C(C(=O)N)=CC=C1C1=CSC=C1 WUWQWRVEZNAWQX-UHFFFAOYSA-N 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical group NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 claims description 5
150000002902 organometallic compounds Chemical class 0.000 claims description 5
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 4
JOJCFDCFBVAXRD-UHFFFAOYSA-N 3-(3-methylphenyl)benzamide Chemical compound CC1=CC=CC(C=2C=C(C=CC=2)C(N)=O)=C1 JOJCFDCFBVAXRD-UHFFFAOYSA-N 0.000 claims description 4
JUVULXADAWDDQO-UHFFFAOYSA-N 3-(4-fluorophenyl)benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=CC(F)=CC=2)=C1 JUVULXADAWDDQO-UHFFFAOYSA-N 0.000 claims description 4
FXJJAMKDEDZECI-UHFFFAOYSA-N 3-naphthalen-2-ylbenzamide Chemical compound NC(=O)C1=CC=CC(C=2C=C3C=CC=CC3=CC=2)=C1 FXJJAMKDEDZECI-UHFFFAOYSA-N 0.000 claims description 4
AMQRIQIWSSZOAL-UHFFFAOYSA-N 3-pyridin-3-ylbenzamide Chemical compound NC(=O)C1=CC=CC(C=2C=NC=CC=2)=C1 AMQRIQIWSSZOAL-UHFFFAOYSA-N 0.000 claims description 4
PLZJHBJVJGMSAJ-UHFFFAOYSA-N 5-(3,5-dimethyl-1,2-oxazol-4-yl)furan-2-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC=C(C(N)=O)O1 PLZJHBJVJGMSAJ-UHFFFAOYSA-N 0.000 claims description 4
NOTULVONTFGQAL-UHFFFAOYSA-N 5-(furan-2-yl)furan-2-carboxamide Chemical compound O1C(C(=O)N)=CC=C1C1=CC=CO1 NOTULVONTFGQAL-UHFFFAOYSA-N 0.000 claims description 4
FQKZSVDOTLUPQS-UHFFFAOYSA-N 5-pyridin-3-yl-2h-1,3-thiazole-3-carboxamide Chemical compound NC(=O)N1CSC(C=2C=NC=CC=2)=C1 FQKZSVDOTLUPQS-UHFFFAOYSA-N 0.000 claims description 4
HNGKXHZFEUZGTI-UHFFFAOYSA-N 5-pyridin-4-yl-2H-1,3-thiazole-3-carboxamide Chemical compound NC(=O)N1CSC(=C1)C1=CC=NC=C1 HNGKXHZFEUZGTI-UHFFFAOYSA-N 0.000 claims description 4
208000024827 Alzheimer disease Diseases 0.000 claims description 4
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SVJPTBLJWPBQJJ-UHFFFAOYSA-N 4-pyridin-3-ylthiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC(C=2C=NC=CC=2)=C1 SVJPTBLJWPBQJJ-UHFFFAOYSA-N 0.000 claims description 3
WFHTYWNCRQLNFY-UHFFFAOYSA-N 5-(3-chlorophenyl)thiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC=C1C1=CC=CC(Cl)=C1 WFHTYWNCRQLNFY-UHFFFAOYSA-N 0.000 claims description 3
JTTIWFBVSGJAJG-UHFFFAOYSA-N 5-(pyridin-3-ylamino)thiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC=C1NC1=CC=CN=C1 JTTIWFBVSGJAJG-UHFFFAOYSA-N 0.000 claims description 3
GYDGAXNDWVXCID-UHFFFAOYSA-N 5-[3-(aminomethyl)phenyl]thiophene-2-carboxamide Chemical compound NCC1=CC=CC(C=2SC(=CC=2)C(N)=O)=C1 GYDGAXNDWVXCID-UHFFFAOYSA-N 0.000 claims description 3
UZHYAVSDVJYYHA-UHFFFAOYSA-N 5-[3-(hydroxymethyl)phenyl]thiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC=C1C1=CC=CC(CO)=C1 UZHYAVSDVJYYHA-UHFFFAOYSA-N 0.000 claims description 3
208000000044 Amnesia Diseases 0.000 claims description 3
101100188551 Arabidopsis thaliana OCT2 gene Proteins 0.000 claims description 3
208000020925 Bipolar disease Diseases 0.000 claims description 3
206010009900 Colitis ulcerative Diseases 0.000 claims description 3
208000023105 Huntington disease Diseases 0.000 claims description 3
208000009829 Lewy Body Disease Diseases 0.000 claims description 3
201000002832 Lewy body dementia Diseases 0.000 claims description 3
206010026749 Mania Diseases 0.000 claims description 3
208000026139 Memory disease Diseases 0.000 claims description 3
206010057852 Nicotine dependence Diseases 0.000 claims description 3
208000025569 Tobacco Use disease Diseases 0.000 claims description 3
201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
208000028683 bipolar I disease Diseases 0.000 claims description 3
230000001713 cholinergic effect Effects 0.000 claims description 3
230000001149 cognitive effect Effects 0.000 claims description 3
230000006984 memory degeneration Effects 0.000 claims description 3
208000023060 memory loss Diseases 0.000 claims description 3
208000015122 neurodegenerative disease Diseases 0.000 claims description 3
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 3
230000036407 pain Effects 0.000 claims description 3
229910052709 silver Inorganic materials 0.000 claims description 3
210000000225 synapse Anatomy 0.000 claims description 3
DAUYIKBTMNZABP-UHFFFAOYSA-N thiophene-3-carboxamide Chemical compound NC(=O)C=1C=CSC=1 DAUYIKBTMNZABP-UHFFFAOYSA-N 0.000 claims description 3
DARQMQSEPIORQR-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]furan-2-carboxamide Chemical compound O1C(C(=O)N)=CC=C1C1=CC=CC(C(F)(F)F)=C1 DARQMQSEPIORQR-UHFFFAOYSA-N 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims 4
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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UA2002075475A 2000-02-18 2001-02-15 Diarylcarboxamides UA73540C2 (en)

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SE0000540A SE0000540D0 (sv)	2000-02-18	2000-02-18	New compounds
PCT/SE2001/000329 WO2001060821A1 (en)	2000-02-18	2001-02-15	Novel biarylcarboxamides

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KR (1)	KR100769394B1 (de)
CN (1)	CN100345847C (de)
AR (1)	AR029798A1 (de)
AT (1)	ATE252099T1 (de)
AU (1)	AU782693B2 (de)
BG (1)	BG106977A (de)
BR (1)	BR0108456A (de)
CA (1)	CA2397233A1 (de)
CO (1)	CO5280046A1 (de)
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RU (1)	RU2263114C2 (de)
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UA (1)	UA73540C2 (de)
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DE10156719A1 (de)	2001-11-19	2003-05-28	Bayer Ag	Heteroarylcarbonsäureamide
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JP2005523288A (ja)	2002-02-19	2005-08-04	ファルマシア・アンド・アップジョン・カンパニー・エルエルシー	疾病治療用の縮合した二環式−ｎ−架橋−複素環式芳香族カルボキサミド
AU2003217275A1 (en) *	2002-02-19	2003-09-09	Pharmacia And Upjohn Company	Azabicyclic compounds for the treatment of disease
DE10211416A1 (de)	2002-03-15	2003-09-25	Bayer Ag	Essig- und Propionsäureamide
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2000
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- 2001-02-15 WO PCT/SE2001/000329 patent/WO2001060821A1/en not_active Ceased
- 2001-02-15 KR KR1020027010731A patent/KR100769394B1/ko not_active Expired - Fee Related
- 2001-02-15 MX MXPA02007543A patent/MXPA02007543A/es active IP Right Grant
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Also Published As

Publication number	Publication date
SK11792002A3 (sk)	2003-04-01
AU782693B2 (en)	2005-08-18
HK1050007A1 (en)	2003-06-06
AU3259401A (en)	2001-08-27
EE200200459A (et)	2003-12-15
US20070149563A1 (en)	2007-06-28
JP4084570B2 (ja)	2008-04-30
US20060128749A1 (en)	2006-06-15
BG106977A (bg)	2003-05-30
PL202044B1 (pl)	2009-05-29
WO2001060821A1 (en)	2001-08-23
US20030008867A1 (en)	2003-01-09
CN1400973A (zh)	2003-03-05
SE0000540D0 (sv)	2000-02-18
KR20020072585A (ko)	2002-09-16
NO20023917L (no)	2002-09-16
NZ520094A (en)	2005-01-28
CN100345847C (zh)	2007-10-31
CA2397233A1 (en)	2001-08-23
EP1259508B1 (de)	2003-10-15
MY123580A (en)	2006-06-30
ZA200205479B (en)	2003-12-31
HUP0301069A2 (hu)	2003-08-28
EE05149B1 (et)	2009-04-15
TR200400072T4 (tr)	2004-02-23
US7001914B2 (en)	2006-02-21
KR100769394B1 (ko)	2007-10-22
MXPA02007543A (es)	2002-12-13
PL357565A1 (en)	2004-07-26
RU2263114C2 (ru)	2005-10-27
US7214688B2 (en)	2007-05-08
CZ20022787A3 (cs)	2003-02-12
IL150544A0 (en)	2003-02-12
DE60100996D1 (de)	2003-11-20
BR0108456A (pt)	2003-04-01
HUP0301069A3 (en)	2004-09-28
JP2003523342A (ja)	2003-08-05
IS6492A (is)	2002-08-08
DK1259508T3 (da)	2004-02-16
AR029798A1 (es)	2003-07-16
DE60100996T2 (de)	2004-09-02
US7491734B2 (en)	2009-02-17
ES2208556T3 (es)	2004-06-16
ATE252099T1 (de)	2003-11-15
PT1259508E (pt)	2004-03-31
NO20023917D0 (no)	2002-08-16
EP1259508A1 (de)	2002-11-27
CO5280046A1 (es)	2003-05-30

Publication	Publication Date	Title
UA73540C2 (en)	2005-08-15	Diarylcarboxamides
EP1539765B1 (de)	2008-12-10	Biaryldiazabicycloalkanamide als nicotinische acetylcholinagonisten
EP1233964B1 (de)	2005-06-22	Neue verwendung sowie neue n-azabicycloamid-verbindungen
NZ535884A (en)	2007-11-30	Pyrrolidinium derivatives as antagonists of M3 muscarinic receptors
KR20040099448A (ko)	2004-11-26	티에닐 화합물
HK1050007B (en)	2004-02-06	Novel biarylcarboxamides
HK1077571B (en)	2009-05-22	Biaryl diazabicycloalkane amides as nicotinic acetylcholine agonists
HK1047743B (en)	2005-09-02	New use and novel n-azabicyclo-amide derivatives