JP2013508385A5 - - Google Patents
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- JP2013508385A5 JP2013508385A5 JP2012535333A JP2012535333A JP2013508385A5 JP 2013508385 A5 JP2013508385 A5 JP 2013508385A5 JP 2012535333 A JP2012535333 A JP 2012535333A JP 2012535333 A JP2012535333 A JP 2012535333A JP 2013508385 A5 JP2013508385 A5 JP 2013508385A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- methoxy
- chromene
- carboxamide
- propyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 54
- 229910052739 hydrogen Inorganic materials 0.000 claims 41
- 239000001257 hydrogen Substances 0.000 claims 41
- 150000002431 hydrogen Chemical class 0.000 claims 22
- 229910052736 halogen Inorganic materials 0.000 claims 21
- 150000002367 halogens Chemical class 0.000 claims 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 19
- NKCLIAPKIOWPQI-UHFFFAOYSA-N 7-methoxy-n-(2-methyl-4-sulfamoylphenyl)-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(S(N)(=O)=O)C=C1C NKCLIAPKIOWPQI-UHFFFAOYSA-N 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- XDJBAFPKRDAYNN-UHFFFAOYSA-N n-(2-ethylpyridin-3-yl)-7-methoxy-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=CN=C1CC XDJBAFPKRDAYNN-UHFFFAOYSA-N 0.000 claims 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 7
- XMUJIPSGSVIHIW-SFHVURJKSA-N (3s)-3-amino-4-[4-[(7-methoxy-2-oxo-8-propylchromene-3-carbonyl)amino]-3-methylanilino]-4-oxobutanoic acid Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(NC(=O)[C@@H](N)CC(O)=O)C=C1C XMUJIPSGSVIHIW-SFHVURJKSA-N 0.000 claims 5
- RUDTYSGXBOPGQW-LJQANCHMSA-N (4r)-4-amino-5-[4-[(7-methoxy-2-oxo-8-propylchromene-3-carbonyl)amino]-3-methylanilino]-5-oxopentanoic acid Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(NC(=O)[C@H](N)CCC(O)=O)C=C1C RUDTYSGXBOPGQW-LJQANCHMSA-N 0.000 claims 5
- YFHRKOQRAMTMJH-UHFFFAOYSA-N 7,8-diethoxy-n-(2-methyl-4-sulfamoylphenyl)-2-oxochromene-3-carboxamide Chemical compound O=C1OC2=C(OCC)C(OCC)=CC=C2C=C1C(=O)NC1=CC=C(S(N)(=O)=O)C=C1C YFHRKOQRAMTMJH-UHFFFAOYSA-N 0.000 claims 5
- AWHRYVRERVXYJG-UHFFFAOYSA-N 7,8-diethoxy-n-[4-(methanesulfonamido)-2-(trifluoromethyl)phenyl]-2-oxochromene-3-carboxamide Chemical compound O=C1OC2=C(OCC)C(OCC)=CC=C2C=C1C(=O)NC1=CC=C(NS(C)(=O)=O)C=C1C(F)(F)F AWHRYVRERVXYJG-UHFFFAOYSA-N 0.000 claims 5
- ZLQHVRUEVDLCTM-UHFFFAOYSA-N 7-methoxy-2-oxo-8-propyl-n-[2-(trifluoromethyl)pyridin-3-yl]chromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=CN=C1C(F)(F)F ZLQHVRUEVDLCTM-UHFFFAOYSA-N 0.000 claims 5
- WGTSLOPIFXMGCD-UHFFFAOYSA-N 7-methoxy-n-(2-methoxypyridin-3-yl)-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=CN=C1OC WGTSLOPIFXMGCD-UHFFFAOYSA-N 0.000 claims 5
- RVTGAAIKWTUHCA-UHFFFAOYSA-N 7-methoxy-n-(2-methylpyridin-3-yl)-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=CN=C1C RVTGAAIKWTUHCA-UHFFFAOYSA-N 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- WBGRUXPFQJAYAE-UHFFFAOYSA-N n-(2-bromo-4-sulfamoylphenyl)-7-methoxy-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(S(N)(=O)=O)C=C1Br WBGRUXPFQJAYAE-UHFFFAOYSA-N 0.000 claims 5
- PYRZKFBGDCLWKA-UHFFFAOYSA-N n-(2-bromopyridin-3-yl)-7-methoxy-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=CN=C1Br PYRZKFBGDCLWKA-UHFFFAOYSA-N 0.000 claims 5
- LKKRZVXANCKBMN-UHFFFAOYSA-N n-(2-chloro-4-sulfamoylphenyl)-7-methoxy-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(S(N)(=O)=O)C=C1Cl LKKRZVXANCKBMN-UHFFFAOYSA-N 0.000 claims 5
- PPCGAUUHIZBQBZ-UHFFFAOYSA-N n-(2-chloropyridin-3-yl)-7-methoxy-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=CN=C1Cl PPCGAUUHIZBQBZ-UHFFFAOYSA-N 0.000 claims 5
- CMGHANZFDCUKLR-UHFFFAOYSA-N n-(4-hydroxy-2-methylphenyl)-7-methoxy-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(O)C=C1C CMGHANZFDCUKLR-UHFFFAOYSA-N 0.000 claims 5
- QLPYUWGDRIETKX-UHFFFAOYSA-N n-[4-(methanesulfonamido)-2-(trifluoromethyl)phenyl]-7-methoxy-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(NS(C)(=O)=O)C=C1C(F)(F)F QLPYUWGDRIETKX-UHFFFAOYSA-N 0.000 claims 5
- WORBNZQIKVAUHD-UHFFFAOYSA-N n-[4-(methanesulfonamido)-2-methylphenyl]-7-methoxy-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(NS(C)(=O)=O)C=C1C WORBNZQIKVAUHD-UHFFFAOYSA-N 0.000 claims 5
- MQZHNBNUESVTAF-UHFFFAOYSA-N n-[4-acetamido-2-(trifluoromethyl)phenyl]-7-methoxy-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(NC(C)=O)C=C1C(F)(F)F MQZHNBNUESVTAF-UHFFFAOYSA-N 0.000 claims 5
- GBFCZNHXFLLWCX-UHFFFAOYSA-N n-[4-hydroxy-2-(trifluoromethyl)phenyl]-7-methoxy-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(O)C=C1C(F)(F)F GBFCZNHXFLLWCX-UHFFFAOYSA-N 0.000 claims 5
- AHUKBXBEQVAPBO-UHFFFAOYSA-N n-[6-(methanesulfonamido)-2-methylpyridin-3-yl]-7-methoxy-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(NS(C)(=O)=O)N=C1C AHUKBXBEQVAPBO-UHFFFAOYSA-N 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 4
- 208000027418 Wounds and injury Diseases 0.000 claims 4
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 4
- 230000006378 damage Effects 0.000 claims 4
- 208000014674 injury Diseases 0.000 claims 4
- SXUJCMLUKCPOQB-UHFFFAOYSA-N n-[4-(methanesulfonamido)-2-methoxyphenyl]-7-methoxy-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(NS(C)(=O)=O)C=C1OC SXUJCMLUKCPOQB-UHFFFAOYSA-N 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- CWULJNQDUNLNDV-UHFFFAOYSA-N 7-methoxy-2-oxo-8-propyl-n-(4-sulfamoylphenyl)chromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(S(N)(=O)=O)C=C1 CWULJNQDUNLNDV-UHFFFAOYSA-N 0.000 claims 3
- OQGSMEKXDGUYGI-UHFFFAOYSA-N 7-methoxy-2-oxo-8-propyl-n-[2-(trifluoromethoxy)phenyl]chromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=CC=C1OC(F)(F)F OQGSMEKXDGUYGI-UHFFFAOYSA-N 0.000 claims 3
- LFLVZDAQVYLTCG-UHFFFAOYSA-N 7-methoxy-2-oxo-8-propyl-n-[2-(trifluoromethyl)phenyl]chromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=CC=C1C(F)(F)F LFLVZDAQVYLTCG-UHFFFAOYSA-N 0.000 claims 3
- HBVMOPHHBLLBBL-UHFFFAOYSA-N 7-methoxy-2-oxo-8-propyl-n-[3-(trifluoromethyl)pyridin-4-yl]chromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=NC=C1C(F)(F)F HBVMOPHHBLLBBL-UHFFFAOYSA-N 0.000 claims 3
- TYMTVCVZIZRYCD-UHFFFAOYSA-N 7-methoxy-n-(2-methyl-4-sulfamoylphenyl)-2-oxo-8-propan-2-yloxychromene-3-carboxamide Chemical compound O=C1OC2=C(OC(C)C)C(OC)=CC=C2C=C1C(=O)NC1=CC=C(S(N)(=O)=O)C=C1C TYMTVCVZIZRYCD-UHFFFAOYSA-N 0.000 claims 3
- UWFNLFSFXRZEDL-UHFFFAOYSA-N 8-ethoxy-7-methoxy-2-oxo-n-[2-(trifluoromethyl)pyridin-3-yl]chromene-3-carboxamide Chemical compound O=C1OC=2C(OCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=CN=C1C(F)(F)F UWFNLFSFXRZEDL-UHFFFAOYSA-N 0.000 claims 3
- HCYBNWMYOVXHEN-UHFFFAOYSA-N 8-ethoxy-7-methoxy-n-(2-methyl-4-sulfamoylphenyl)-2-oxochromene-3-carboxamide Chemical compound O=C1OC=2C(OCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(S(N)(=O)=O)C=C1C HCYBNWMYOVXHEN-UHFFFAOYSA-N 0.000 claims 3
- UPSMEWJCKGINAV-UHFFFAOYSA-N [3-chloro-4-[(7-methoxy-2-oxo-8-propylchromene-3-carbonyl)amino]phenyl]boronic acid Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(B(O)O)C=C1Cl UPSMEWJCKGINAV-UHFFFAOYSA-N 0.000 claims 3
- RJASNKXSDPCQFI-UHFFFAOYSA-N [4-[(7-methoxy-2-oxo-8-propylchromene-3-carbonyl)amino]-3-methylphenyl]phosphonic acid Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(P(O)(O)=O)C=C1C RJASNKXSDPCQFI-UHFFFAOYSA-N 0.000 claims 3
- 150000001299 aldehydes Chemical class 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 3
- OLTQZVZQPRTXCK-UHFFFAOYSA-N n-(2-bromophenyl)-7-methoxy-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=CC=C1Br OLTQZVZQPRTXCK-UHFFFAOYSA-N 0.000 claims 3
- MPHJLIUHCGDFSW-UHFFFAOYSA-N n-(2-ethylphenyl)-7-methoxy-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=CC=C1CC MPHJLIUHCGDFSW-UHFFFAOYSA-N 0.000 claims 3
- OUNWBTAPLPTHBE-UHFFFAOYSA-N n-(3-chloropyridin-4-yl)-7-methoxy-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=NC=C1Cl OUNWBTAPLPTHBE-UHFFFAOYSA-N 0.000 claims 3
- ATLWOZNXBZCXBT-UHFFFAOYSA-N n-(4-acetamido-2-methylphenyl)-7-methoxy-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(NC(C)=O)C=C1C ATLWOZNXBZCXBT-UHFFFAOYSA-N 0.000 claims 3
- VIVCQZNCRYMURD-UHFFFAOYSA-N n-[2-(difluoromethoxy)phenyl]-7-methoxy-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=CC=C1OC(F)F VIVCQZNCRYMURD-UHFFFAOYSA-N 0.000 claims 3
- 238000001356 surgical procedure Methods 0.000 claims 3
- 208000006820 Arthralgia Diseases 0.000 claims 2
- -1 diastereoisomers Chemical class 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 230000029663 wound healing Effects 0.000 claims 2
- PYZTVFPPTAGDBT-UHFFFAOYSA-N 3-[[4-[(7-methoxy-2-oxo-8-propylchromene-3-carbonyl)amino]-3-methylphenyl]sulfonylamino]propanoic acid Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(S(=O)(=O)NCCC(O)=O)C=C1C PYZTVFPPTAGDBT-UHFFFAOYSA-N 0.000 claims 1
- NCOSSPBRMMNNBZ-UHFFFAOYSA-N 7-methoxy-2-oxo-8-propan-2-yloxy-n-[2-(trifluoromethyl)phenyl]chromene-3-carboxamide Chemical compound O=C1OC2=C(OC(C)C)C(OC)=CC=C2C=C1C(=O)NC1=CC=CC=C1C(F)(F)F NCOSSPBRMMNNBZ-UHFFFAOYSA-N 0.000 claims 1
- OSNPYWDOSPYMKB-UHFFFAOYSA-N 7-methoxy-2-oxo-8-propan-2-yloxy-n-[2-(trifluoromethyl)pyridin-3-yl]chromene-3-carboxamide Chemical compound O=C1OC2=C(OC(C)C)C(OC)=CC=C2C=C1C(=O)NC1=CC=CN=C1C(F)(F)F OSNPYWDOSPYMKB-UHFFFAOYSA-N 0.000 claims 1
- NRBGRNSVXHQIDM-UHFFFAOYSA-N 7-methoxy-2-oxo-8-propyl-n-(2-propylphenyl)chromene-3-carboxamide Chemical compound CCCC1=CC=CC=C1NC(=O)C1=CC2=CC=C(OC)C(CCC)=C2OC1=O NRBGRNSVXHQIDM-UHFFFAOYSA-N 0.000 claims 1
- GGFZKDUJSVUAAS-UHFFFAOYSA-N 7-methoxy-2-oxo-8-propyl-n-[4-(pyrrolidin-3-ylamino)phenyl]chromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC(C=C1)=CC=C1NC1CCNC1 GGFZKDUJSVUAAS-UHFFFAOYSA-N 0.000 claims 1
- ISIILKKXLMQZHJ-UHFFFAOYSA-N 7-methoxy-2-oxo-8-propyl-n-[4-sulfamoyl-2-(trifluoromethyl)phenyl]chromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(S(N)(=O)=O)C=C1C(F)(F)F ISIILKKXLMQZHJ-UHFFFAOYSA-N 0.000 claims 1
- TUKSXTIVZJKEKW-UHFFFAOYSA-N 7-methoxy-2-oxo-8-propyl-n-pyridin-3-ylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=CN=C1 TUKSXTIVZJKEKW-UHFFFAOYSA-N 0.000 claims 1
- GXYFIRQILLOEBQ-UHFFFAOYSA-N 7-methoxy-2-oxo-8-propyl-n-pyridin-4-ylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=NC=C1 GXYFIRQILLOEBQ-UHFFFAOYSA-N 0.000 claims 1
- SINYPPASKWIFSG-UHFFFAOYSA-N 7-methoxy-2-oxo-n-[4-(piperidin-2-ylmethylamino)phenyl]-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC(C=C1)=CC=C1NCC1CCCCN1 SINYPPASKWIFSG-UHFFFAOYSA-N 0.000 claims 1
- ILRCIVHDFGDFPH-UHFFFAOYSA-N 7-methoxy-2-oxo-n-[4-(piperidin-3-ylamino)phenyl]-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC(C=C1)=CC=C1NC1CCCNC1 ILRCIVHDFGDFPH-UHFFFAOYSA-N 0.000 claims 1
- BQWOTCCYTUXCFA-UHFFFAOYSA-N 7-methoxy-2-oxo-n-[4-(piperidin-3-ylmethylamino)phenyl]-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC(C=C1)=CC=C1NCC1CCCNC1 BQWOTCCYTUXCFA-UHFFFAOYSA-N 0.000 claims 1
- HPZYHKCYYQFJOF-UHFFFAOYSA-N 7-methoxy-n-(2-methoxyphenyl)-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=CC=C1OC HPZYHKCYYQFJOF-UHFFFAOYSA-N 0.000 claims 1
- BYSNZIZAKOHOAW-UHFFFAOYSA-N 7-methoxy-n-(2-methylphenyl)-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=CC=C1C BYSNZIZAKOHOAW-UHFFFAOYSA-N 0.000 claims 1
- VCTQOVLQQGIXOQ-UHFFFAOYSA-N 7-methoxy-n-(2-methylpyridin-3-yl)-2-oxo-8-propan-2-yloxychromene-3-carboxamide Chemical compound O=C1OC2=C(OC(C)C)C(OC)=CC=C2C=C1C(=O)NC1=CC=CN=C1C VCTQOVLQQGIXOQ-UHFFFAOYSA-N 0.000 claims 1
- IYNGBTMWYNYEEC-UHFFFAOYSA-N 7-methoxy-n-(2-methylsulfanylphenyl)-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=CC=C1SC IYNGBTMWYNYEEC-UHFFFAOYSA-N 0.000 claims 1
- YAWLMRDQYLGVKG-UHFFFAOYSA-N 7-methoxy-n-(3-methylpyridin-2-yl)-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=NC=CC=C1C YAWLMRDQYLGVKG-UHFFFAOYSA-N 0.000 claims 1
- XSXJNEQUWLJUPS-UHFFFAOYSA-N 7-methoxy-n-(3-methylpyridin-4-yl)-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=NC=C1C XSXJNEQUWLJUPS-UHFFFAOYSA-N 0.000 claims 1
- OFYIJONCOOYTEO-UHFFFAOYSA-N 7-methoxy-n-[2-methyl-4-(methylsulfamoyl)phenyl]-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(S(=O)(=O)NC)C=C1C OFYIJONCOOYTEO-UHFFFAOYSA-N 0.000 claims 1
- FVEJGQHYMNHDBY-UHFFFAOYSA-N 7-methoxy-n-[2-methyl-4-(methylsulfonylmethyl)phenyl]-2-oxo-8-propylchromene-3-carboxamide Chemical compound O=C1OC=2C(CCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(CS(C)(=O)=O)C=C1C FVEJGQHYMNHDBY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- NRTHJBQQHIOGRJ-UHFFFAOYSA-N 8-ethoxy-7-methoxy-2-oxo-n-[2-(trifluoromethyl)phenyl]chromene-3-carboxamide Chemical compound O=C1OC=2C(OCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=CC=C1C(F)(F)F NRTHJBQQHIOGRJ-UHFFFAOYSA-N 0.000 claims 1
- VIHTWMCPNIWCRD-UHFFFAOYSA-N 8-ethoxy-7-methoxy-n-(2-methylpyridin-3-yl)-2-oxochromene-3-carboxamide Chemical compound O=C1OC=2C(OCC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=CN=C1C VIHTWMCPNIWCRD-UHFFFAOYSA-N 0.000 claims 1
- STFPIVSYKOUENW-UHFFFAOYSA-N 8-ethyl-7-methoxy-n-(2-methyl-4-sulfamoylphenyl)-2-oxochromene-3-carboxamide Chemical compound O=C1OC=2C(CC)=C(OC)C=CC=2C=C1C(=O)NC1=CC=C(S(N)(=O)=O)C=C1C STFPIVSYKOUENW-UHFFFAOYSA-N 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010003645 Atopy Diseases 0.000 claims 1
- 206010003694 Atrophy Diseases 0.000 claims 1
- 208000023328 Basedow disease Diseases 0.000 claims 1
- 208000010392 Bone Fractures Diseases 0.000 claims 1
- KWNCOOWERVGCBT-UHFFFAOYSA-N CCCc1c(OC)ccc2cc(C(=O)Nc3ccc(CS(O)(=O)=O)cc3C)c(=O)oc12 Chemical compound CCCc1c(OC)ccc2cc(C(=O)Nc3ccc(CS(O)(=O)=O)cc3C)c(=O)oc12 KWNCOOWERVGCBT-UHFFFAOYSA-N 0.000 claims 1
- 208000033379 Chorioretinopathy Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
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| US12478503B2 (en) | 2009-05-18 | 2025-11-25 | Glaukos Corporation | Implants with controlled drug delivery features and methods of using same |
| US10206813B2 (en) | 2009-05-18 | 2019-02-19 | Dose Medical Corporation | Implants with controlled drug delivery features and methods of using same |
| EP2491023B1 (en) * | 2009-10-23 | 2014-12-31 | Allergan, Inc. | Coumarin compounds as receptor modulators with therapeutic utility |
| CN107868069A (zh) * | 2017-10-31 | 2018-04-03 | 山东新华制药股份有限公司 | 7‑羟基‑8‑甲基‑6‑硝基‑2‑氧‑2h‑苯并吡喃‑3‑羧酸的制备工艺 |
| CN107935976B (zh) * | 2017-11-13 | 2020-01-17 | 山东大学 | 香豆素酰胺衍生物及其应用 |
| CN111683682A (zh) | 2018-02-02 | 2020-09-18 | 国立大学法人京都大学 | 用于预防或治疗伴有眼内血管新生和/或眼内血管通透性亢进的眼科疾病的药物 |
| CN110713497A (zh) * | 2019-10-30 | 2020-01-21 | 成都海杰亚医药科技有限公司 | 一种Brigatinib的中间体2-氨基苯基二甲基氧化膦制备方法 |
| US12273086B2 (en) * | 2022-08-31 | 2025-04-08 | Apple Inc. | Adjustable radio-frequency splitter-combiner |
| CN116478173B (zh) * | 2023-04-20 | 2025-03-25 | 山西师范大学 | 一种靶向高尔基体监测极性的荧光探针及其制备与应用 |
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| MXPA05011597A (es) * | 2003-04-30 | 2005-12-15 | Novartis Ag | Derivados de aminopropanol como moduladores del receptor 1-fosfato de esfingosina. |
| CN1777575B (zh) * | 2003-04-30 | 2010-05-12 | 诺瓦提斯公司 | 作为1-磷酸-鞘氨醇受体调节剂的氨基-丙醇衍生物 |
| GB0607389D0 (en) * | 2006-04-12 | 2006-05-24 | Novartis Ag | Organic compounds |
| US20100144729A1 (en) * | 2007-02-02 | 2010-06-10 | Rolf Baenteli | Coumarin derivatives |
| CN101790519B (zh) | 2007-08-08 | 2013-10-16 | 默克雪兰诺有限公司 | 用于治疗多发性硬化症的结合于鞘氨醇1-磷酸(s1p)的6-氨基-嘧啶-4-羧酰胺衍生物及相关化合物 |
| EP2491023B1 (en) * | 2009-10-23 | 2014-12-31 | Allergan, Inc. | Coumarin compounds as receptor modulators with therapeutic utility |
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