ZA200305009B - Substituted derivatives of aminofuran-2-yl-acetic acid and aminothien-2-yl-acetic and the use thereof for treating migraines and pain. - Google Patents
Substituted derivatives of aminofuran-2-yl-acetic acid and aminothien-2-yl-acetic and the use thereof for treating migraines and pain. Download PDFInfo
- Publication number
- ZA200305009B ZA200305009B ZA200305009A ZA200305009A ZA200305009B ZA 200305009 B ZA200305009 B ZA 200305009B ZA 200305009 A ZA200305009 A ZA 200305009A ZA 200305009 A ZA200305009 A ZA 200305009A ZA 200305009 B ZA200305009 B ZA 200305009B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- methyl
- furan
- phenylamino
- acetic acid
- Prior art date
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- 208000002193 Pain Diseases 0.000 title claims description 16
- 208000019695 Migraine disease Diseases 0.000 title claims description 4
- DYFYPSCJKBYYNK-UHFFFAOYSA-N 2-azaniumyl-2-(furan-2-yl)acetate Chemical class OC(=O)C(N)C1=CC=CO1 DYFYPSCJKBYYNK-UHFFFAOYSA-N 0.000 title description 4
- -1 (Ci_¢—alkyl)-aryl Chemical group 0.000 claims description 79
- 125000000623 heterocyclic group Chemical group 0.000 claims description 63
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Chemical group 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000003367 polycyclic group Chemical group 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 206010027599 migraine Diseases 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- MYWPIJKTTXHAIE-UHFFFAOYSA-N 2-(4-methoxyanilino)-2-thiophen-2-ylacetic acid Chemical compound C1=CC(OC)=CC=C1NC(C(O)=O)C1=CC=CS1 MYWPIJKTTXHAIE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 20
- 239000000203 mixture Substances 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- AYRYHNFAYDEGBU-UHFFFAOYSA-N 2-(3,4-dichloroanilino)-2-[5-(sulfanylmethyl)furan-2-yl]acetic acid Chemical compound C=1C=C(CS)OC=1C(C(=O)O)NC1=CC=C(Cl)C(Cl)=C1 AYRYHNFAYDEGBU-UHFFFAOYSA-N 0.000 claims 2
- BMPVGHHFWXMUAK-UHFFFAOYSA-N 2-(3-chloroanilino)-2-[5-(sulfanylmethyl)furan-2-yl]acetic acid Chemical compound C=1C=C(CS)OC=1C(C(=O)O)NC1=CC=CC(Cl)=C1 BMPVGHHFWXMUAK-UHFFFAOYSA-N 0.000 claims 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 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 2
- 241000124008 Mammalia Species 0.000 claims 2
- SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical compound C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- ABYZSYDGJGVCHS-ZETCQYMHSA-N (2s)-2-acetamido-n-(4-nitrophenyl)propanamide Chemical compound CC(=O)N[C@@H](C)C(=O)NC1=CC=C([N+]([O-])=O)C=C1 ABYZSYDGJGVCHS-ZETCQYMHSA-N 0.000 claims 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- XQSLDUGJWUZKEN-UHFFFAOYSA-N 2-(2,3-dichloroanilino)-2-(3-methyl-5-methylsulfanylfuran-2-yl)acetic acid Chemical compound ClC1=C(C=CC=C1Cl)NC(C(=O)O)C=1OC(=CC=1C)SC XQSLDUGJWUZKEN-UHFFFAOYSA-N 0.000 claims 1
- RNBFXAIARLKQAH-UHFFFAOYSA-N 2-(2,4-dibromo-5-methylanilino)-2-(4-methylthiophen-2-yl)acetic acid Chemical compound CC1=CSC(C(NC=2C(=CC(Br)=C(C)C=2)Br)C(O)=O)=C1 RNBFXAIARLKQAH-UHFFFAOYSA-N 0.000 claims 1
- WXMFLHFPYVJUMU-UHFFFAOYSA-N 2-(2,4-dibromoanilino)-2-[5-(methylsulfanylmethyl)furan-2-yl]acetic acid Chemical compound O1C(CSC)=CC=C1C(C(O)=O)NC1=CC=C(Br)C=C1Br WXMFLHFPYVJUMU-UHFFFAOYSA-N 0.000 claims 1
- KYJVDBSKFNSTEL-UHFFFAOYSA-N 2-(2,4-dichloroanilino)-2-(3-methyl-5-methylsulfanylfuran-2-yl)acetic acid Chemical compound ClC1=C(C=CC(=C1)Cl)NC(C(=O)O)C=1OC(=CC=1C)SC KYJVDBSKFNSTEL-UHFFFAOYSA-N 0.000 claims 1
- OIPDXBIVXODDRB-UHFFFAOYSA-N 2-(2,4-dichloroanilino)-2-(4-methylthiophen-2-yl)acetic acid Chemical compound CC1=CSC(C(NC=2C(=CC(Cl)=CC=2)Cl)C(O)=O)=C1 OIPDXBIVXODDRB-UHFFFAOYSA-N 0.000 claims 1
- MIYIFABJAQZVOZ-UHFFFAOYSA-N 2-(2,4-dichloroanilino)-2-(furan-2-yl)acetic acid Chemical compound C=1C=COC=1C(C(=O)O)NC1=CC=C(Cl)C=C1Cl MIYIFABJAQZVOZ-UHFFFAOYSA-N 0.000 claims 1
- ZSQDDUQEWPQGFU-UHFFFAOYSA-N 2-(2-chloro-4-fluoroanilino)-2-(3-methyl-5-methylsulfanylfuran-2-yl)acetic acid Chemical compound O1C(SC)=CC(C)=C1C(C(O)=O)NC1=CC=C(F)C=C1Cl ZSQDDUQEWPQGFU-UHFFFAOYSA-N 0.000 claims 1
- GMJGCRKGGSVNGP-UHFFFAOYSA-N 2-(2-chloro-4-fluoroanilino)-2-(4-ethoxycarbonyl-5-methylfuran-2-yl)acetic acid Chemical compound O1C(C)=C(C(=O)OCC)C=C1C(C(O)=O)NC1=CC=C(F)C=C1Cl GMJGCRKGGSVNGP-UHFFFAOYSA-N 0.000 claims 1
- HCNOXMYCGSVGKE-UHFFFAOYSA-N 2-(2-chloro-4-methylanilino)-2-(3-methyl-5-methylsulfanylfuran-2-yl)acetic acid Chemical compound O1C(SC)=CC(C)=C1C(C(O)=O)NC1=CC=C(C)C=C1Cl HCNOXMYCGSVGKE-UHFFFAOYSA-N 0.000 claims 1
- XMVCORBVELDZKX-UHFFFAOYSA-N 2-(2-chloro-4-methylanilino)-2-[5-(furan-2-ylmethylsulfanylmethyl)furan-2-yl]acetic acid Chemical compound ClC1=CC(C)=CC=C1NC(C(O)=O)C(O1)=CC=C1CSCC1=CC=CO1 XMVCORBVELDZKX-UHFFFAOYSA-N 0.000 claims 1
- JMNMGSADSWHQNT-UHFFFAOYSA-N 2-(2-chloroanilino)-2-(4-ethoxycarbonyl-5-methylfuran-2-yl)acetic acid Chemical compound O1C(C)=C(C(=O)OCC)C=C1C(C(O)=O)NC1=CC=CC=C1Cl JMNMGSADSWHQNT-UHFFFAOYSA-N 0.000 claims 1
- KMKGQTWHLXAQMD-UHFFFAOYSA-N 2-(2-chloroanilino)-2-[5-(methylsulfanylmethyl)furan-2-yl]acetic acid Chemical compound O1C(CSC)=CC=C1C(C(O)=O)NC1=CC=CC=C1Cl KMKGQTWHLXAQMD-UHFFFAOYSA-N 0.000 claims 1
- UWSUDXNTRMYKPX-UHFFFAOYSA-N 2-(2-ethylanilino)-2-[5-(methylsulfanylmethyl)furan-2-yl]acetic acid Chemical compound CCC1=CC=CC=C1NC(C(O)=O)C1=CC=C(CSC)O1 UWSUDXNTRMYKPX-UHFFFAOYSA-N 0.000 claims 1
- SKWBXCPGKHTIKS-UHFFFAOYSA-N 2-(2-ethylanilino)-2-[5-[2-(furan-2-yl)-1-sulfanylethyl]furan-2-yl]acetic acid Chemical compound C(C)C1=C(C=CC=C1)NC(C(=O)O)C=1OC(=CC=1)C(S)CC=1OC=CC=1 SKWBXCPGKHTIKS-UHFFFAOYSA-N 0.000 claims 1
- BNBJXURKIUSODV-UHFFFAOYSA-N 2-(2-methylanilino)-2-[5-(methylsulfanylmethyl)furan-2-yl]acetic acid Chemical compound O1C(CSC)=CC=C1C(C(O)=O)NC1=CC=CC=C1C BNBJXURKIUSODV-UHFFFAOYSA-N 0.000 claims 1
- OLKAFPSACXEHBJ-UHFFFAOYSA-N 2-(3,5-dichloroanilino)-2-(3-methyl-5-methylsulfanylfuran-2-yl)acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)NC(C(=O)O)C=1OC(=CC=1C)SC OLKAFPSACXEHBJ-UHFFFAOYSA-N 0.000 claims 1
- ZGIHRUOGXVDVPV-UHFFFAOYSA-N 2-(3,5-dichloroanilino)-2-(4-methoxycarbonyl-5-methylfuran-2-yl)acetic acid Chemical compound O1C(C)=C(C(=O)OC)C=C1C(C(O)=O)NC1=CC(Cl)=CC(Cl)=C1 ZGIHRUOGXVDVPV-UHFFFAOYSA-N 0.000 claims 1
- APYOODDMLWUTSI-UHFFFAOYSA-N 2-(3,5-dichloroanilino)-2-(4-methylthiophen-2-yl)acetic acid Chemical compound CC1=CSC(C(NC=2C=C(Cl)C=C(Cl)C=2)C(O)=O)=C1 APYOODDMLWUTSI-UHFFFAOYSA-N 0.000 claims 1
- BPAXBNILKFUGOH-UHFFFAOYSA-N 2-(3,5-dichloroanilino)-2-(5-ethylthiophen-2-yl)acetic acid Chemical compound S1C(CC)=CC=C1C(C(O)=O)NC1=CC(Cl)=CC(Cl)=C1 BPAXBNILKFUGOH-UHFFFAOYSA-N 0.000 claims 1
- RBUUZJFVQFLPAS-UHFFFAOYSA-N 2-(3,5-dichloroanilino)-2-(5-methylthiophen-2-yl)acetic acid Chemical compound S1C(C)=CC=C1C(C(O)=O)NC1=CC(Cl)=CC(Cl)=C1 RBUUZJFVQFLPAS-UHFFFAOYSA-N 0.000 claims 1
- DYZWIAMWIRTSAJ-UHFFFAOYSA-N 2-(3,5-dichloroanilino)-2-(furan-2-yl)acetic acid Chemical compound C=1C=COC=1C(C(=O)O)NC1=CC(Cl)=CC(Cl)=C1 DYZWIAMWIRTSAJ-UHFFFAOYSA-N 0.000 claims 1
- QZSFJTIYTOCAJY-UHFFFAOYSA-N 2-(3,5-dichloroanilino)-2-[3-methyl-5-(methyldisulfanyl)furan-2-yl]acetic acid Chemical compound ClC=1C=C(C=C(C=1)Cl)NC(C(=O)O)C=1OC(=CC=1C)SSC QZSFJTIYTOCAJY-UHFFFAOYSA-N 0.000 claims 1
- KPEPGVJPQHCMLM-UHFFFAOYSA-N 2-(3,5-dichloroanilino)-2-[5-(hydroxymethyl)thiophen-2-yl]acetic acid Chemical compound S1C(CO)=CC=C1C(C(O)=O)NC1=CC(Cl)=CC(Cl)=C1 KPEPGVJPQHCMLM-UHFFFAOYSA-N 0.000 claims 1
- WASVFYTZILWXPZ-UHFFFAOYSA-N 2-(3,5-dichloroanilino)-2-[5-(sulfanylmethyl)furan-2-yl]acetic acid Chemical compound C=1C=C(CS)OC=1C(C(=O)O)NC1=CC(Cl)=CC(Cl)=C1 WASVFYTZILWXPZ-UHFFFAOYSA-N 0.000 claims 1
- UDWZBTAJJXOGIP-UHFFFAOYSA-N 2-(3,5-dichloroanilino)-2-[5-[2-(furan-2-yl)-1-sulfanylethyl]furan-2-yl]acetic acid Chemical compound C=1C=C(C(S)CC=2OC=CC=2)OC=1C(C(=O)O)NC1=CC(Cl)=CC(Cl)=C1 UDWZBTAJJXOGIP-UHFFFAOYSA-N 0.000 claims 1
- IXNJGMBRZFSSFP-UHFFFAOYSA-N 2-(3-chloro-2-methylanilino)-2-(3-methyl-5-methylsulfanylfuran-2-yl)acetic acid Chemical compound O1C(SC)=CC(C)=C1C(C(O)=O)NC1=CC=CC(Cl)=C1C IXNJGMBRZFSSFP-UHFFFAOYSA-N 0.000 claims 1
- YTGJNMDKPCCOOT-UHFFFAOYSA-N 2-(3-methylthiophen-2-yl)acetic acid Chemical compound CC=1C=CSC=1CC(O)=O YTGJNMDKPCCOOT-UHFFFAOYSA-N 0.000 claims 1
- JFLJVHBNSAFDII-UHFFFAOYSA-N 2-(4-acetyl-3,5-dimethylfuran-2-yl)-2-(2,3-dichloroanilino)acetic acid Chemical compound CC(=O)C1=C(C)OC(C(NC=2C(=C(Cl)C=CC=2)Cl)C(O)=O)=C1C JFLJVHBNSAFDII-UHFFFAOYSA-N 0.000 claims 1
- IJUXNOJCDWJDSS-UHFFFAOYSA-N 2-(4-acetyl-3,5-dimethylfuran-2-yl)-2-(2-chloro-4-methylanilino)acetic acid Chemical compound CC(=O)C1=C(C)OC(C(NC=2C(=CC(C)=CC=2)Cl)C(O)=O)=C1C IJUXNOJCDWJDSS-UHFFFAOYSA-N 0.000 claims 1
- QZRCXHLKJQQHPP-UHFFFAOYSA-N 2-(4-bromo-2-chloroanilino)-2-(3-methylthiophen-2-yl)acetic acid Chemical compound C1=CSC(C(NC=2C(=CC(Br)=CC=2)Cl)C(O)=O)=C1C QZRCXHLKJQQHPP-UHFFFAOYSA-N 0.000 claims 1
- VXYDIHRWMRTNKS-UHFFFAOYSA-N 2-(4-bromo-2-chloroanilino)-2-(4-ethoxycarbonyl-3,5-dimethylfuran-2-yl)acetic acid Chemical compound CCOC(=O)C1=C(C)OC(C(NC=2C(=CC(Br)=CC=2)Cl)C(O)=O)=C1C VXYDIHRWMRTNKS-UHFFFAOYSA-N 0.000 claims 1
- IHKNKYUBERAJHK-UHFFFAOYSA-N 2-(4-bromo-2-chloroanilino)-2-(4-ethoxycarbonyl-5-methylfuran-2-yl)acetic acid Chemical compound O1C(C)=C(C(=O)OCC)C=C1C(C(O)=O)NC1=CC=C(Br)C=C1Cl IHKNKYUBERAJHK-UHFFFAOYSA-N 0.000 claims 1
- ZXEORFNLLGDMJY-UHFFFAOYSA-N 2-(4-bromo-2-chloroanilino)-2-(4-methoxycarbonyl-5-methylfuran-2-yl)acetic acid Chemical compound O1C(C)=C(C(=O)OC)C=C1C(C(O)=O)NC1=CC=C(Br)C=C1Cl ZXEORFNLLGDMJY-UHFFFAOYSA-N 0.000 claims 1
- SXQAGNIDPONNOT-UHFFFAOYSA-N 2-(4-chloro-2-methylanilino)-2-(3-methyl-5-methylsulfanylfuran-2-yl)acetic acid Chemical compound O1C(SC)=CC(C)=C1C(C(O)=O)NC1=CC=C(Cl)C=C1C SXQAGNIDPONNOT-UHFFFAOYSA-N 0.000 claims 1
- HWZDTBVFWCVTGS-UHFFFAOYSA-N 2-(4-chloro-2-methylanilino)-2-[5-(furan-2-ylmethylsulfanylmethyl)furan-2-yl]acetic acid Chemical compound CC1=CC(Cl)=CC=C1NC(C(O)=O)C(O1)=CC=C1CSCC1=CC=CO1 HWZDTBVFWCVTGS-UHFFFAOYSA-N 0.000 claims 1
- NSEBNZMDRLHCHE-UHFFFAOYSA-N 2-(4-cyanoanilino)-2-(4-ethoxycarbonyl-3,5-dimethylfuran-2-yl)acetic acid Chemical compound CCOC(=O)C1=C(C)OC(C(NC=2C=CC(=CC=2)C#N)C(O)=O)=C1C NSEBNZMDRLHCHE-UHFFFAOYSA-N 0.000 claims 1
- FARHDZOPPXWSJI-UHFFFAOYSA-N 2-(4-cyanoanilino)-2-(4-methoxycarbonyl-5-methylfuran-2-yl)acetic acid Chemical compound O1C(C)=C(C(=O)OC)C=C1C(C(O)=O)NC1=CC=C(C#N)C=C1 FARHDZOPPXWSJI-UHFFFAOYSA-N 0.000 claims 1
- GTNJYFZRECJTPZ-UHFFFAOYSA-N 2-(4-ethoxycarbonyl-3,5-dimethylfuran-2-yl)-2-(2-phenoxyanilino)acetic acid Chemical compound CCOC(=O)C1=C(C)OC(C(NC=2C(=CC=CC=2)OC=2C=CC=CC=2)C(O)=O)=C1C GTNJYFZRECJTPZ-UHFFFAOYSA-N 0.000 claims 1
- PDKRHNQHFZZUDV-UHFFFAOYSA-N 2-(4-iodoanilino)-2-[5-(methylsulfanylmethyl)furan-2-yl]acetic acid Chemical compound O1C(CSC)=CC=C1C(C(O)=O)NC1=CC=C(I)C=C1 PDKRHNQHFZZUDV-UHFFFAOYSA-N 0.000 claims 1
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- GGTJWZPIMZYFNP-UHFFFAOYSA-N 2-(4-methylthiophen-2-yl)acetic acid Chemical compound CC1=CSC(CC(O)=O)=C1 GGTJWZPIMZYFNP-UHFFFAOYSA-N 0.000 claims 1
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- XPBHMZFQWZGDSD-UHFFFAOYSA-N 2-(5-chloro-2-methylanilino)-2-(3-methyl-5-methylsulfanylfuran-2-yl)acetic acid Chemical compound O1C(SC)=CC(C)=C1C(C(O)=O)NC1=CC(Cl)=CC=C1C XPBHMZFQWZGDSD-UHFFFAOYSA-N 0.000 claims 1
- FBQZBZQTKHHWDC-UHFFFAOYSA-N 2-(5-chloro-2-methylanilino)-2-[5-(furan-2-ylmethylsulfanylmethyl)furan-2-yl]acetic acid Chemical compound CC1=CC=C(Cl)C=C1NC(C(O)=O)C(O1)=CC=C1CSCC1=CC=CO1 FBQZBZQTKHHWDC-UHFFFAOYSA-N 0.000 claims 1
- TWYOQYCRGKDCCE-UHFFFAOYSA-N 2-(5-chlorothiophen-2-yl)-2-(3,5-dichloroanilino)acetic acid Chemical compound C=1C=C(Cl)SC=1C(C(=O)O)NC1=CC(Cl)=CC(Cl)=C1 TWYOQYCRGKDCCE-UHFFFAOYSA-N 0.000 claims 1
- BXKRGDWHSKTQQL-UHFFFAOYSA-N 2-(5-tert-butylfuran-2-yl)-2-(3,5-dichloroanilino)acetic acid Chemical compound O1C(C(C)(C)C)=CC=C1C(C(O)=O)NC1=CC(Cl)=CC(Cl)=C1 BXKRGDWHSKTQQL-UHFFFAOYSA-N 0.000 claims 1
- UVJMESDNURHNAJ-UHFFFAOYSA-N 2-[(3,5-dibromo-6-methylpyridin-2-yl)amino]-2-(4-methoxycarbonyl-5-methylfuran-2-yl)acetic acid Chemical compound O1C(C)=C(C(=O)OC)C=C1C(C(O)=O)NC1=NC(C)=C(Br)C=C1Br UVJMESDNURHNAJ-UHFFFAOYSA-N 0.000 claims 1
- WKWICCOHDOESQB-UHFFFAOYSA-N 2-[(3,5-dibromo-6-methylpyridin-2-yl)amino]-2-(furan-2-yl)acetic acid Chemical compound C1=C(Br)C(C)=NC(NC(C(O)=O)C=2OC=CC=2)=C1Br WKWICCOHDOESQB-UHFFFAOYSA-N 0.000 claims 1
- VBODHEFHBHPGOM-UHFFFAOYSA-N 2-[(3,5-dibromo-6-methylpyridin-2-yl)amino]-2-[4-(hydroxymethyl)furan-2-yl]acetic acid Chemical compound C1=C(Br)C(C)=NC(NC(C(O)=O)C=2OC=C(CO)C=2)=C1Br VBODHEFHBHPGOM-UHFFFAOYSA-N 0.000 claims 1
- LPBXYGAIVSCENO-UHFFFAOYSA-N 2-[(3,5-dibromopyridin-2-yl)amino]-2-(3-methyl-5-methylsulfanylfuran-2-yl)acetic acid Chemical compound O1C(SC)=CC(C)=C1C(C(O)=O)NC1=NC=C(Br)C=C1Br LPBXYGAIVSCENO-UHFFFAOYSA-N 0.000 claims 1
- RNSQXSNTEWMBLE-UHFFFAOYSA-N 2-[(3,5-dibromopyridin-2-yl)amino]-2-(furan-2-yl)acetic acid Chemical compound C=1C=COC=1C(C(=O)O)NC1=NC=C(Br)C=C1Br RNSQXSNTEWMBLE-UHFFFAOYSA-N 0.000 claims 1
- KKEUVYGWPYINDL-UHFFFAOYSA-N 2-[(3,5-dichloropyridin-2-yl)amino]-2-(4-methylthiophen-2-yl)acetic acid Chemical compound CC1=CSC(C(NC=2C(=CC(Cl)=CN=2)Cl)C(O)=O)=C1 KKEUVYGWPYINDL-UHFFFAOYSA-N 0.000 claims 1
- GXRHEGXMGHSSSH-UHFFFAOYSA-N 2-[(3,5-dichloropyridin-2-yl)amino]-2-(furan-2-yl)acetic acid Chemical compound C=1C=COC=1C(C(=O)O)NC1=NC=C(Cl)C=C1Cl GXRHEGXMGHSSSH-UHFFFAOYSA-N 0.000 claims 1
- GGGFRFJYHYUYER-UHFFFAOYSA-N 2-[(5-bromopyrimidin-2-yl)amino]-2-(furan-2-yl)acetic acid Chemical compound C=1C=COC=1C(C(=O)O)NC1=NC=C(Br)C=N1 GGGFRFJYHYUYER-UHFFFAOYSA-N 0.000 claims 1
- ZOHAFNZEJRQVQD-UHFFFAOYSA-N 2-[(5-tert-butyl-1H-pyrazol-3-yl)amino]-2-(4-hydroxy-3-methylfuran-2-yl)acetic acid Chemical compound C(C)(C)(C)C1=CC(=NN1)NC(C(=O)O)C=1OC=C(C=1C)O ZOHAFNZEJRQVQD-UHFFFAOYSA-N 0.000 claims 1
- DQQRVXLCILFBAW-UHFFFAOYSA-N 2-[4-chloro-3-(trifluoromethyl)anilino]-2-(4-ethoxycarbonyl-5-methylfuran-2-yl)acetic acid Chemical compound O1C(C)=C(C(=O)OCC)C=C1C(C(O)=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 DQQRVXLCILFBAW-UHFFFAOYSA-N 0.000 claims 1
- LTPCTCHPEQAWJY-UHFFFAOYSA-N 2-[4-chloro-3-(trifluoromethyl)anilino]-2-[5-(2-ethoxy-2-oxoethyl)thiophen-2-yl]acetic acid Chemical compound S1C(CC(=O)OCC)=CC=C1C(C(O)=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 LTPCTCHPEQAWJY-UHFFFAOYSA-N 0.000 claims 1
- PWLWNGFPRUHXRK-UHFFFAOYSA-N 2-[4-chloro-3-(trifluoromethyl)anilino]-2-[5-(methylsulfanylmethyl)furan-2-yl]acetic acid Chemical compound O1C(CSC)=CC=C1C(C(O)=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 PWLWNGFPRUHXRK-UHFFFAOYSA-N 0.000 claims 1
- RZVJYWIFDWENDK-UHFFFAOYSA-N 2-[5-(acetylsulfanylmethyl)furan-2-yl]-2-(3,5-dichloroanilino)acetic acid Chemical compound O1C(CSC(=O)C)=CC=C1C(C(O)=O)NC1=CC(Cl)=CC(Cl)=C1 RZVJYWIFDWENDK-UHFFFAOYSA-N 0.000 claims 1
- LXJGZKBIGOIPSD-UHFFFAOYSA-N 2-[5-(methylsulfanylmethyl)furan-2-yl]-2-(2-propan-2-ylanilino)acetic acid Chemical compound O1C(CSC)=CC=C1C(C(O)=O)NC1=CC=CC=C1C(C)C LXJGZKBIGOIPSD-UHFFFAOYSA-N 0.000 claims 1
- NCNSLVCCYXTRKZ-UHFFFAOYSA-N 2-[[3-chloro-5-(trifluoromethyl)pyridin-2-yl]amino]-2-(furan-2-yl)acetic acid Chemical compound C=1C=COC=1C(C(=O)O)NC1=NC=C(C(F)(F)F)C=C1Cl NCNSLVCCYXTRKZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 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 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 1
- LOFDXZJSDVCYAS-UHFFFAOYSA-N Ethyl 3-furoate Chemical compound CCOC(=O)C=1C=COC=1 LOFDXZJSDVCYAS-UHFFFAOYSA-N 0.000 claims 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- MEWDRZHJUIORHH-UHFFFAOYSA-N ethyl 2-(2,3-dichloroanilino)-2-(furan-2-yl)acetate Chemical compound C=1C=COC=1C(C(=O)OCC)NC1=CC=CC(Cl)=C1Cl MEWDRZHJUIORHH-UHFFFAOYSA-N 0.000 claims 1
- JGGTVAZXIVGCPQ-UHFFFAOYSA-N ethyl 2-(2,3-dichloroanilino)-2-[4-(hydroxymethyl)furan-2-yl]acetate Chemical compound C=1C(CO)=COC=1C(C(=O)OCC)NC1=CC=CC(Cl)=C1Cl JGGTVAZXIVGCPQ-UHFFFAOYSA-N 0.000 claims 1
- UXCNLSRKTJDWAE-UHFFFAOYSA-N ethyl 2-(3,5-dichloroanilino)-2-(3-methylthiophen-2-yl)acetate Chemical compound S1C=CC(C)=C1C(C(=O)OCC)NC1=CC(Cl)=CC(Cl)=C1 UXCNLSRKTJDWAE-UHFFFAOYSA-N 0.000 claims 1
- BRVOMDLPVURAEL-UHFFFAOYSA-N ethyl 2-(3,5-dichloroanilino)-2-(5-propylthiophen-2-yl)acetate Chemical compound S1C(CCC)=CC=C1C(C(=O)OCC)NC1=CC(Cl)=CC(Cl)=C1 BRVOMDLPVURAEL-UHFFFAOYSA-N 0.000 claims 1
- JMXOQGWZOOZRIT-UHFFFAOYSA-N ethyl 2-(3,5-dichloroanilino)-2-[4-(hydroxymethyl)furan-2-yl]acetate Chemical compound C=1C(CO)=COC=1C(C(=O)OCC)NC1=CC(Cl)=CC(Cl)=C1 JMXOQGWZOOZRIT-UHFFFAOYSA-N 0.000 claims 1
- FCGPMLYGLDMOQJ-UHFFFAOYSA-N ethyl 2-(3,5-dichloroanilino)-2-thiophen-2-ylacetate Chemical compound C=1C=CSC=1C(C(=O)OCC)NC1=CC(Cl)=CC(Cl)=C1 FCGPMLYGLDMOQJ-UHFFFAOYSA-N 0.000 claims 1
- IHUDREJVBPDDEM-UHFFFAOYSA-N ethyl 2-(4-bromofuran-2-yl)-2-(3,5-dichloroanilino)acetate Chemical compound C=1C(Br)=COC=1C(C(=O)OCC)NC1=CC(Cl)=CC(Cl)=C1 IHUDREJVBPDDEM-UHFFFAOYSA-N 0.000 claims 1
- WMRPDWPZJKCXTJ-UHFFFAOYSA-N ethyl 2-(4-chloro-2-methylanilino)-2-[4-(hydroxymethyl)furan-2-yl]acetate Chemical compound C=1C(CO)=COC=1C(C(=O)OCC)NC1=CC=C(Cl)C=C1C WMRPDWPZJKCXTJ-UHFFFAOYSA-N 0.000 claims 1
- SDVPYZQCHSDHBG-UHFFFAOYSA-N ethyl 2-[(4-cyano-3-methylsulfanyl-1h-pyrazol-5-yl)amino]-2-[4-(hydroxymethyl)furan-2-yl]acetate Chemical compound C=1C(CO)=COC=1C(C(=O)OCC)NC1=NNC(SC)=C1C#N SDVPYZQCHSDHBG-UHFFFAOYSA-N 0.000 claims 1
- IZVBPHKOLJDKRZ-UHFFFAOYSA-N ethyl 2-[4-(hydroxymethyl)furan-2-yl]-2-(4-iodoanilino)acetate Chemical compound C=1C(CO)=COC=1C(C(=O)OCC)NC1=CC=C(I)C=C1 IZVBPHKOLJDKRZ-UHFFFAOYSA-N 0.000 claims 1
- NJESBPMVLDCWGF-UHFFFAOYSA-N ethyl 2-[4-(hydroxymethyl)furan-2-yl]-2-(4-phenoxyanilino)acetate Chemical compound C=1C(CO)=COC=1C(C(=O)OCC)NC(C=C1)=CC=C1OC1=CC=CC=C1 NJESBPMVLDCWGF-UHFFFAOYSA-N 0.000 claims 1
- BIMHZGTXXSCWKN-UHFFFAOYSA-N ethyl 2-[4-(hydroxymethyl)furan-2-yl]-2-[(5-oxo-4-phenyldiazenyl-1,2-dihydropyrazol-3-yl)amino]acetate Chemical compound C=1C(CO)=COC=1C(C(=O)OCC)NC1=NNC(O)=C1N=NC1=CC=CC=C1 BIMHZGTXXSCWKN-UHFFFAOYSA-N 0.000 claims 1
- RCTTXQJFUHLHEC-UHFFFAOYSA-N ethyl 2-[5-(2-ethoxy-2-oxoethyl)thiophen-2-yl]-2-[(5-oxo-4-phenyldiazenyl-1,2-dihydropyrazol-3-yl)amino]acetate Chemical compound S1C(CC(=O)OCC)=CC=C1C(C(=O)OCC)NC1=NNC(O)=C1N=NC1=CC=CC=C1 RCTTXQJFUHLHEC-UHFFFAOYSA-N 0.000 claims 1
- JVNFCFAADDPCNF-UHFFFAOYSA-N ethyl 5-[1-(2,3-dichloroanilino)-2-ethoxy-2-oxoethyl]-2-methylfuran-3-carboxylate Chemical compound C=1C(C(=O)OCC)=C(C)OC=1C(C(=O)OCC)NC1=CC=CC(Cl)=C1Cl JVNFCFAADDPCNF-UHFFFAOYSA-N 0.000 claims 1
- NVBMLSOGDQFATR-UHFFFAOYSA-N ethyl 5-[1-(2-chloro-4-fluoroanilino)-2-ethoxy-2-oxoethyl]-2-methylfuran-3-carboxylate Chemical compound C=1C(C(=O)OCC)=C(C)OC=1C(C(=O)OCC)NC1=CC=C(F)C=C1Cl NVBMLSOGDQFATR-UHFFFAOYSA-N 0.000 claims 1
- HWNAJLQFRBOZQA-UHFFFAOYSA-N ethyl 5-[1-(2-chloroanilino)-2-ethoxy-2-oxoethyl]-2-methylfuran-3-carboxylate Chemical compound C=1C(C(=O)OCC)=C(C)OC=1C(C(=O)OCC)NC1=CC=CC=C1Cl HWNAJLQFRBOZQA-UHFFFAOYSA-N 0.000 claims 1
- YUXIXCVBIQNJBC-UHFFFAOYSA-N ethyl 5-[1-(4-bromo-2-chloroanilino)-2-ethoxy-2-oxoethyl]-2-methylfuran-3-carboxylate Chemical compound C=1C(C(=O)OCC)=C(C)OC=1C(C(=O)OCC)NC1=CC=C(Br)C=C1Cl YUXIXCVBIQNJBC-UHFFFAOYSA-N 0.000 claims 1
- QKVURYOYZOXSLC-UHFFFAOYSA-N ethyl 5-[1-[(4-cyano-3-methylsulfanyl-1h-pyrazol-5-yl)amino]-2-ethoxy-2-oxoethyl]-2-methylfuran-3-carboxylate Chemical compound C=1C(C(=O)OCC)=C(C)OC=1C(C(=O)OCC)NC1=NNC(SC)=C1C#N QKVURYOYZOXSLC-UHFFFAOYSA-N 0.000 claims 1
- TZTBHHOIZRZUMB-UHFFFAOYSA-N ethyl 5-[[2-ethoxy-1-(4-ethoxycarbonyl-5-methylfuran-2-yl)-2-oxoethyl]amino]-1h-pyrazole-4-carboxylate Chemical compound C=1C(C(=O)OCC)=C(C)OC=1C(C(=O)OCC)NC1=NNC=C1C(=O)OCC TZTBHHOIZRZUMB-UHFFFAOYSA-N 0.000 claims 1
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical class OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims 1
- TXXQDZJFUOKVJV-UHFFFAOYSA-N methyl 5-[1-(3,5-dichloroanilino)-2-ethoxy-2-oxoethyl]-2-methylfuran-3-carboxylate Chemical compound C=1C(C(=O)OC)=C(C)OC=1C(C(=O)OCC)NC1=CC(Cl)=CC(Cl)=C1 TXXQDZJFUOKVJV-UHFFFAOYSA-N 0.000 claims 1
- WEADAQGZURKKEI-UHFFFAOYSA-N methyl 5-[1-(4-chloro-2-methylanilino)-2-ethoxy-2-oxoethyl]-2-methylfuran-3-carboxylate Chemical compound C=1C(C(=O)OC)=C(C)OC=1C(C(=O)OCC)NC1=CC=C(Cl)C=C1C WEADAQGZURKKEI-UHFFFAOYSA-N 0.000 claims 1
- VKKPNZLDKAPFES-UHFFFAOYSA-N methyl 5-[2-ethoxy-2-oxo-1-(4-phenoxyanilino)ethyl]-2-methylfuran-3-carboxylate Chemical compound C=1C(C(=O)OC)=C(C)OC=1C(C(=O)OCC)NC(C=C1)=CC=C1OC1=CC=CC=C1 VKKPNZLDKAPFES-UHFFFAOYSA-N 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 description 8
- 108090000862 Ion Channels Proteins 0.000 description 6
- 102000004310 Ion Channels Human genes 0.000 description 6
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 150000005840 aryl radicals Chemical class 0.000 description 3
- 229940005483 opioid analgesics Drugs 0.000 description 3
- XLMSKXASROPJNG-UHFFFAOYSA-N 2-azaniumyl-2-thiophen-2-ylacetate Chemical class OC(=O)C(N)C1=CC=CS1 XLMSKXASROPJNG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000000094 Chronic Pain Diseases 0.000 description 2
- 206010010774 Constipation Diseases 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 208000004756 Respiratory Insufficiency Diseases 0.000 description 2
- 206010038678 Respiratory depression Diseases 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229960005181 morphine Drugs 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 230000008673 vomiting Effects 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical group [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 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
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 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
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 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
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 230000002981 neuropathic effect Effects 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
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- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
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- 230000036280 sedation Effects 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10059864A DE10059864A1 (de) | 2000-11-30 | 2000-11-30 | Substituierte Amino-furan-2-yl-essigsäure- und Amino-thien-2-yl-essigsäure-Derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200305009B true ZA200305009B (en) | 2004-08-18 |
Family
ID=7665508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200305009A ZA200305009B (en) | 2000-11-30 | 2003-06-26 | Substituted derivatives of aminofuran-2-yl-acetic acid and aminothien-2-yl-acetic and the use thereof for treating migraines and pain. |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US6797712B2 (enExample) |
| EP (1) | EP1341786B9 (enExample) |
| JP (1) | JP4340063B2 (enExample) |
| KR (1) | KR20030055334A (enExample) |
| CN (1) | CN1326854C (enExample) |
| AR (1) | AR035658A1 (enExample) |
| AT (1) | ATE418552T1 (enExample) |
| AU (2) | AU2002220735B2 (enExample) |
| BR (1) | BR0115883A (enExample) |
| CA (1) | CA2430280A1 (enExample) |
| CY (1) | CY1108871T1 (enExample) |
| CZ (1) | CZ20031509A3 (enExample) |
| DE (2) | DE10059864A1 (enExample) |
| DK (1) | DK1341786T3 (enExample) |
| EC (1) | ECSDI034631S (enExample) |
| ES (1) | ES2320198T3 (enExample) |
| HU (1) | HUP0303041A3 (enExample) |
| IL (2) | IL156139A0 (enExample) |
| MX (1) | MXPA03004303A (enExample) |
| NO (1) | NO20032340L (enExample) |
| NZ (1) | NZ526554A (enExample) |
| PE (1) | PE20020599A1 (enExample) |
| PL (1) | PL362978A1 (enExample) |
| PT (1) | PT1341786E (enExample) |
| RU (1) | RU2003117703A (enExample) |
| SI (1) | SI1341786T1 (enExample) |
| SK (1) | SK5942003A3 (enExample) |
| WO (1) | WO2002044171A1 (enExample) |
| ZA (1) | ZA200305009B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6794506B2 (en) * | 2000-07-21 | 2004-09-21 | Elan Pharmaceuticals, Inc. | 3-(heteroaryl) alanine derivatives-inhibitors of leukocyte adhesion mediated by VLA-4 |
| DE10125145A1 (de) | 2001-05-22 | 2002-11-28 | Gruenenthal Gmbh | Substituierte C-Furan-2-yl-methylamin- und C-Thiophen-2-yl-methylamin-Derivate |
| GB0302094D0 (en) * | 2003-01-29 | 2003-02-26 | Pharmagene Lab Ltd | EP4 receptor antagonists |
| DE10306202A1 (de) * | 2003-02-13 | 2004-08-26 | Grünenthal GmbH | Arzneimittel enthaltend substituierte 2-Aryl-Aminoessigsäure-Verbindungen und/oder substituierte 2-Heteroaryl-Aminoessigsäure-Verbindungen |
| DE10306203A1 (de) | 2003-02-13 | 2004-08-26 | Grünenthal GmbH | Arzneimittel enthaltend substituierte 2-Heteroaryl-Aminoessigsäure-Verbindungen |
| GB0324269D0 (en) * | 2003-10-16 | 2003-11-19 | Pharmagene Lab Ltd | EP4 receptor antagonists |
| US9259426B2 (en) | 2006-07-20 | 2016-02-16 | Gilead Sciences, Inc. | 4,6-di- and 2,4,6-trisubstituted quinazoline derivatives useful for treating viral infections |
| WO2008009079A2 (en) * | 2006-07-20 | 2008-01-24 | Gilead Sciences, Inc. | Substituted pteridines useful for the treatment and prevention of viral infections |
| AU2016216673B2 (en) | 2015-03-04 | 2017-02-02 | Gilead Sciences, Inc. | Toll like receptor modulator compounds |
| US10640499B2 (en) | 2016-09-02 | 2020-05-05 | Gilead Sciences, Inc. | Toll like receptor modulator compounds |
| AU2017318601B2 (en) | 2016-09-02 | 2020-09-03 | Gilead Sciences, Inc. | Toll like receptor modulator compounds |
| TWI751516B (zh) | 2019-04-17 | 2022-01-01 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
| TW202212339A (zh) | 2019-04-17 | 2022-04-01 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
| TWI879779B (zh) | 2019-06-28 | 2025-04-11 | 美商基利科學股份有限公司 | 類鐸受體調節劑化合物的製備方法 |
| CN115382297B (zh) * | 2022-04-12 | 2023-10-31 | 江阴市华思诚无纺布有限公司 | 熔体直纺双组分pet纺粘液体过滤材料及其制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0923544B1 (en) * | 1996-06-28 | 2008-10-15 | University of Southern California | Method for the synthesis of amines and amino acids with organoboron derivatives |
| US6441237B1 (en) | 1999-02-20 | 2002-08-27 | Boehringer Ingelheim Pharma Kg | Substituted 3-phenoxy- and 3-phenylalkyloxy-2-phenyl-propylamines |
| DE19907385A1 (de) * | 1999-02-20 | 2000-08-24 | Boehringer Ingelheim Pharma | Neue substituierte 3-Phenoxy- und 3-Phenylalkyloxy-2-phenyl-propylamine |
| GB0030304D0 (en) * | 2000-12-13 | 2001-01-24 | Lilly Co Eli | Compounds |
-
2000
- 2000-11-30 DE DE10059864A patent/DE10059864A1/de not_active Ceased
-
2001
- 2001-11-26 AR ARP010105486A patent/AR035658A1/es not_active Application Discontinuation
- 2001-11-28 BR BR0115883-0A patent/BR0115883A/pt not_active IP Right Cessation
- 2001-11-28 IL IL15613901A patent/IL156139A0/xx active IP Right Grant
- 2001-11-28 NZ NZ526554A patent/NZ526554A/en unknown
- 2001-11-28 CA CA002430280A patent/CA2430280A1/en not_active Abandoned
- 2001-11-28 SI SI200130905T patent/SI1341786T1/sl unknown
- 2001-11-28 DE DE50114605T patent/DE50114605D1/de not_active Expired - Lifetime
- 2001-11-28 DK DK01998547T patent/DK1341786T3/da active
- 2001-11-28 JP JP2002546541A patent/JP4340063B2/ja not_active Expired - Fee Related
- 2001-11-28 CN CNB018197876A patent/CN1326854C/zh not_active Expired - Fee Related
- 2001-11-28 KR KR10-2003-7007315A patent/KR20030055334A/ko not_active Withdrawn
- 2001-11-28 AU AU2002220735A patent/AU2002220735B2/en not_active Ceased
- 2001-11-28 PT PT01998547T patent/PT1341786E/pt unknown
- 2001-11-28 HU HU0303041A patent/HUP0303041A3/hu unknown
- 2001-11-28 PL PL01362978A patent/PL362978A1/xx not_active Application Discontinuation
- 2001-11-28 CZ CZ20031509A patent/CZ20031509A3/cs unknown
- 2001-11-28 SK SK594-2003A patent/SK5942003A3/sk not_active Application Discontinuation
- 2001-11-28 RU RU2003117703/04A patent/RU2003117703A/ru not_active Application Discontinuation
- 2001-11-28 AT AT01998547T patent/ATE418552T1/de active
- 2001-11-28 ES ES01998547T patent/ES2320198T3/es not_active Expired - Lifetime
- 2001-11-28 WO PCT/EP2001/013910 patent/WO2002044171A1/de not_active Ceased
- 2001-11-28 MX MXPA03004303A patent/MXPA03004303A/es active IP Right Grant
- 2001-11-28 AU AU2073502A patent/AU2073502A/xx active Pending
- 2001-11-28 EP EP01998547A patent/EP1341786B9/de not_active Expired - Lifetime
- 2001-11-29 PE PE2001001195A patent/PE20020599A1/es not_active Application Discontinuation
-
2003
- 2003-05-23 NO NO20032340A patent/NO20032340L/no not_active Application Discontinuation
- 2003-05-27 IL IL156139A patent/IL156139A/en not_active IP Right Cessation
- 2003-05-29 EC EC2003004631F patent/ECSDI034631S/es unknown
- 2003-05-30 US US10/448,323 patent/US6797712B2/en not_active Expired - Fee Related
- 2003-06-26 ZA ZA200305009A patent/ZA200305009B/en unknown
-
2009
- 2009-03-12 CY CY20091100279T patent/CY1108871T1/el unknown
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