JP2009528273A5 - - Google Patents
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- JP2009528273A5 JP2009528273A5 JP2008552473A JP2008552473A JP2009528273A5 JP 2009528273 A5 JP2009528273 A5 JP 2009528273A5 JP 2008552473 A JP2008552473 A JP 2008552473A JP 2008552473 A JP2008552473 A JP 2008552473A JP 2009528273 A5 JP2009528273 A5 JP 2009528273A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- biphenyl
- methyl
- oxazol
- phenyl
- 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.)
- Ceased
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- 150000001875 compounds Chemical class 0.000 claims 48
- 125000000623 heterocyclic group Chemical group 0.000 claims 28
- 125000001072 heteroaryl group Chemical group 0.000 claims 26
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 24
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 23
- 125000000547 substituted alkyl group Chemical group 0.000 claims 23
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 23
- -1 benzamidazolyl Chemical group 0.000 claims 22
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 22
- 125000003107 substituted aryl group Chemical group 0.000 claims 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims 21
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 125000005843 halogen group Chemical group 0.000 claims 16
- 125000001188 haloalkyl group Chemical group 0.000 claims 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000003282 alkyl amino group Chemical group 0.000 claims 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000004414 alkyl thio group Chemical group 0.000 claims 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 239000000651 prodrug Substances 0.000 claims 4
- 229940002612 prodrug Drugs 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- UCQNKNQITPQKJF-UHFFFAOYSA-N 2-amino-3-methyl-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]butanamide Chemical compound C1=CC(NC(=O)C(N)C(C)C)=CC=C1C1=CC(C=2OC=CN=2)=CC=C1C UCQNKNQITPQKJF-UHFFFAOYSA-N 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- YRGWJOUGAJJWCB-UHFFFAOYSA-N 4-methyl-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]piperazine-1-carboxamide Chemical compound C1CN(C)CCN1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=CN=2)C)C=C1 YRGWJOUGAJJWCB-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 230000005931 immune cell recruitment Effects 0.000 claims 2
- 230000003834 intracellular effect Effects 0.000 claims 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
- WMHUOUZPWCALNT-UHFFFAOYSA-N n-[4-[2-chloro-5-(trifluoromethyl)phenyl]phenyl]-2-methylcyclohexane-1-carboxamide Chemical compound CC1CCCCC1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)C=C1 WMHUOUZPWCALNT-UHFFFAOYSA-N 0.000 claims 2
- LZMAXIVLNFMYRN-UHFFFAOYSA-N n-[4-[2-chloro-5-(trifluoromethyl)phenyl]phenyl]bicyclo[2.2.1]hept-2-ene-5-carboxamide Chemical compound FC(F)(F)C1=CC=C(Cl)C(C=2C=CC(NC(=O)C3C4CC(C=C4)C3)=CC=2)=C1 LZMAXIVLNFMYRN-UHFFFAOYSA-N 0.000 claims 2
- DCIKCTPQGJBSGF-UHFFFAOYSA-N n-[4-[2-chloro-5-(trifluoromethyl)phenyl]phenyl]cyclopentanecarboxamide Chemical compound FC(F)(F)C1=CC=C(Cl)C(C=2C=CC(NC(=O)C3CCCC3)=CC=2)=C1 DCIKCTPQGJBSGF-UHFFFAOYSA-N 0.000 claims 2
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims 2
- JOWNNSFMZBXPCX-UHFFFAOYSA-N 1-methyl-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]piperidine-2-carboxamide Chemical compound CN1CCCCC1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=CN=2)C)C=C1 JOWNNSFMZBXPCX-UHFFFAOYSA-N 0.000 claims 1
- QIBBBRDIJDCMNO-UHFFFAOYSA-N 1-methyl-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]piperidine-4-carboxamide Chemical compound C1CN(C)CCC1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=CN=2)C)C=C1 QIBBBRDIJDCMNO-UHFFFAOYSA-N 0.000 claims 1
- VTCREEJWHYLEPP-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]ethanethioamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=S)CC1=CC=C(F)C=C1F VTCREEJWHYLEPP-UHFFFAOYSA-N 0.000 claims 1
- CDQXHLRJARHGOI-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]acetamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)CC1=C(Cl)C=CC=C1Cl CDQXHLRJARHGOI-UHFFFAOYSA-N 0.000 claims 1
- FUTYSOUYFGQSCS-UHFFFAOYSA-N 2-(2,6-difluorophenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]acetamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)CC1=C(F)C=CC=C1F FUTYSOUYFGQSCS-UHFFFAOYSA-N 0.000 claims 1
- GKFHQXLETVACSV-UHFFFAOYSA-N 2-(2-fluorophenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]acetamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)CC1=CC=CC=C1F GKFHQXLETVACSV-UHFFFAOYSA-N 0.000 claims 1
- ONMLXXQMEFNUIV-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=CN=2)C)C=C1 ONMLXXQMEFNUIV-UHFFFAOYSA-N 0.000 claims 1
- KDOMWAVYWJJMQN-UHFFFAOYSA-N 2-(3-bromophenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]acetamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)CC1=CC=CC(Br)=C1 KDOMWAVYWJJMQN-UHFFFAOYSA-N 0.000 claims 1
- IOXMDSZFCNXWIR-UHFFFAOYSA-N 2-(3-fluorophenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]acetamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)CC1=CC=CC(F)=C1 IOXMDSZFCNXWIR-UHFFFAOYSA-N 0.000 claims 1
- ZYLGEYKBLCYQKR-UHFFFAOYSA-N 2-(3-methoxyphenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]acetamide Chemical compound COC1=CC=CC(CC(=O)NC=2C=CC(=CC=2)C=2C(=CC=C(C=2)C=2OC=CN=2)C)=C1 ZYLGEYKBLCYQKR-UHFFFAOYSA-N 0.000 claims 1
- MWDKZIHNGHELHT-UHFFFAOYSA-N 2-(4-bromophenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]acetamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)CC1=CC=C(Br)C=C1 MWDKZIHNGHELHT-UHFFFAOYSA-N 0.000 claims 1
- IYNXVJDVGTUIQS-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]acetamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)CC1=CC=C(Cl)C=C1 IYNXVJDVGTUIQS-UHFFFAOYSA-N 0.000 claims 1
- XOMFVQYSOAEFSH-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]acetamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)CC1=CC=C(F)C=C1 XOMFVQYSOAEFSH-UHFFFAOYSA-N 0.000 claims 1
- ABBBNTYNNCUCGP-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=CN=2)C)C=C1 ABBBNTYNNCUCGP-UHFFFAOYSA-N 0.000 claims 1
- QPPVRNVAVCLJFM-UHFFFAOYSA-N 2-(dimethylamino)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]butanamide;hydrochloride Chemical compound Cl.C1=CC(NC(=O)C(N(C)C)CC)=CC=C1C1=CC(C=2OC=CN=2)=CC=C1C QPPVRNVAVCLJFM-UHFFFAOYSA-N 0.000 claims 1
- LUVJMZLRAOGATM-UHFFFAOYSA-N 2-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]anilino]ethanol Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C1=CC=C(NCCO)C=C1 LUVJMZLRAOGATM-UHFFFAOYSA-N 0.000 claims 1
- JITAUCPEIVAKMF-UHFFFAOYSA-N 2-amino-3-(1h-indol-3-yl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]propanamide Chemical compound C1=C(C=2C=CC(NC(=O)C(N)CC=3C4=CC=CC=C4NC=3)=CC=2)C(C)=CC=C1C1=NC=CO1 JITAUCPEIVAKMF-UHFFFAOYSA-N 0.000 claims 1
- KTUKDWXIHVUOKV-UHFFFAOYSA-N 2-amino-3-methyl-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]pentanamide Chemical compound C1=CC(NC(=O)C(N)C(C)CC)=CC=C1C1=CC(C=2OC=CN=2)=CC=C1C KTUKDWXIHVUOKV-UHFFFAOYSA-N 0.000 claims 1
- DBYWEUNEJPEGEJ-UHFFFAOYSA-N 2-amino-4-methyl-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]pentanamide Chemical compound C1=CC(NC(=O)C(N)CC(C)C)=CC=C1C1=CC(C=2OC=CN=2)=CC=C1C DBYWEUNEJPEGEJ-UHFFFAOYSA-N 0.000 claims 1
- HPXGHVXABRKILF-UHFFFAOYSA-N 2-amino-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]-3-phenylpropanamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)C(N)CC1=CC=CC=C1 HPXGHVXABRKILF-UHFFFAOYSA-N 0.000 claims 1
- UHJXEZUXVPEWJI-UHFFFAOYSA-N 2-amino-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]-4-methylsulfanylbutanamide Chemical compound C1=CC(NC(=O)C(N)CCSC)=CC=C1C1=CC(C=2OC=CN=2)=CC=C1C UHJXEZUXVPEWJI-UHFFFAOYSA-N 0.000 claims 1
- HZMIEUCUBBIFDK-UHFFFAOYSA-N 2-amino-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]acetamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C1=CC=C(NC(=O)CN)C=C1 HZMIEUCUBBIFDK-UHFFFAOYSA-N 0.000 claims 1
- WTOLZLALSIRXGR-UHFFFAOYSA-N 2-amino-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]butanamide Chemical compound C1=CC(NC(=O)C(N)CC)=CC=C1C1=CC(C=2OC=CN=2)=CC=C1C WTOLZLALSIRXGR-UHFFFAOYSA-N 0.000 claims 1
- NERACDKTFODCKU-UHFFFAOYSA-N 2-amino-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]propanamide Chemical compound C1=CC(NC(=O)C(N)C)=CC=C1C1=CC(C=2OC=CN=2)=CC=C1C NERACDKTFODCKU-UHFFFAOYSA-N 0.000 claims 1
- PKPGNMNJGMIOGR-UHFFFAOYSA-N 2-methyl-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]propanamide Chemical compound C1=CC(NC(=O)C(C)C)=CC=C1C1=CC(C=2OC=CN=2)=CC=C1C PKPGNMNJGMIOGR-UHFFFAOYSA-N 0.000 claims 1
- YNZHESZIXUECBD-UHFFFAOYSA-N 2-methyl-n-[4-[2-methyl-5-(1,3-thiazol-2-yl)phenyl]phenyl]propanamide Chemical compound C1=CC(NC(=O)C(C)C)=CC=C1C1=CC(C=2SC=CN=2)=CC=C1C YNZHESZIXUECBD-UHFFFAOYSA-N 0.000 claims 1
- OLIOPBNPTGBEAC-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]prop-2-enamide Chemical compound COC1=CC=CC(C=CC(=O)NC=2C=CC(=CC=2)C=2C(=CC=C(C=2)C=2OC=CN=2)C)=C1OC OLIOPBNPTGBEAC-UHFFFAOYSA-N 0.000 claims 1
- GKECJKFMDAFING-UHFFFAOYSA-N 3-(2,5-dimethoxyphenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]prop-2-enamide Chemical compound COC1=CC=C(OC)C(C=CC(=O)NC=2C=CC(=CC=2)C=2C(=CC=C(C=2)C=2OC=CN=2)C)=C1 GKECJKFMDAFING-UHFFFAOYSA-N 0.000 claims 1
- OTTBPDJHZYHBDV-UHFFFAOYSA-N 3-(2,6-difluorophenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]prop-2-enamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)C=CC1=C(F)C=CC=C1F OTTBPDJHZYHBDV-UHFFFAOYSA-N 0.000 claims 1
- QTBXMJOWNQHIEN-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]prop-2-enamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)C=CC1=CC=CC=C1Cl QTBXMJOWNQHIEN-UHFFFAOYSA-N 0.000 claims 1
- YWFGEHRNLGACME-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]prop-2-enamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)C=CC1=CC=C(Cl)C(Cl)=C1 YWFGEHRNLGACME-UHFFFAOYSA-N 0.000 claims 1
- RABQXOMBFGLURQ-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]prop-2-enamide Chemical compound C1=C(OC)C(OC)=CC=C1C=CC(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=CN=2)C)C=C1 RABQXOMBFGLURQ-UHFFFAOYSA-N 0.000 claims 1
- QZLVXPDFQOCWBX-UHFFFAOYSA-N 3-(3-bromophenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]prop-2-enamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)C=CC1=CC=CC(Br)=C1 QZLVXPDFQOCWBX-UHFFFAOYSA-N 0.000 claims 1
- PBHGXWFEXSPKHZ-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]prop-2-enamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)C=CC1=CC=CC(Cl)=C1 PBHGXWFEXSPKHZ-UHFFFAOYSA-N 0.000 claims 1
- XRVLTDMUOCFNNS-UHFFFAOYSA-N 3-(4-bromophenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]prop-2-enamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)C=CC1=CC=C(Br)C=C1 XRVLTDMUOCFNNS-UHFFFAOYSA-N 0.000 claims 1
- WNXLRQNMVVRSEI-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]prop-2-enamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)C=CC1=CC=C(Cl)C=C1 WNXLRQNMVVRSEI-UHFFFAOYSA-N 0.000 claims 1
- IOKAMTMGXUKJAS-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]prop-2-enamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)C=CC1=CC=C(F)C=C1 IOKAMTMGXUKJAS-UHFFFAOYSA-N 0.000 claims 1
- UDECGIDYYYHFTL-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]prop-2-enamide Chemical compound C1=CC(OC)=CC=C1C=CC(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=CN=2)C)C=C1 UDECGIDYYYHFTL-UHFFFAOYSA-N 0.000 claims 1
- ZLGGPJNFPYBGKA-UHFFFAOYSA-N 3-(dimethylamino)-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]propanamide Chemical compound C1=CC(NC(=O)CCN(C)C)=CC=C1C1=CC(C=2OC=CN=2)=CC=C1C ZLGGPJNFPYBGKA-UHFFFAOYSA-N 0.000 claims 1
- NXXJVSLUBBCBFY-UHFFFAOYSA-N 3-amino-n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]propanamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C1=CC=C(NC(=O)CCN)C=C1 NXXJVSLUBBCBFY-UHFFFAOYSA-N 0.000 claims 1
- OAEIDCQLWWAZRZ-UHFFFAOYSA-N 4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]-n-(2-methylpropyl)aniline Chemical compound C1=CC(NCC(C)C)=CC=C1C1=CC(C=2OC=CN=2)=CC=C1C OAEIDCQLWWAZRZ-UHFFFAOYSA-N 0.000 claims 1
- QMIUJLOXUDUBIF-UHFFFAOYSA-N 6-[4-(butylamino)phenyl]-1,3-benzodioxole-5-carbaldehyde Chemical compound C1=CC(NCCCC)=CC=C1C(C(=C1)C=O)=CC2=C1OCO2 QMIUJLOXUDUBIF-UHFFFAOYSA-N 0.000 claims 1
- 102000004310 Ion Channels Human genes 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- 210000001744 T-lymphocyte Anatomy 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- XOUQVLDFAALEMT-UHFFFAOYSA-N [6-[4-(butylamino)phenyl]-1,3-benzodioxol-5-yl]methanol Chemical compound C1=CC(NCCCC)=CC=C1C(C(=C1)CO)=CC2=C1OCO2 XOUQVLDFAALEMT-UHFFFAOYSA-N 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 239000000427 antigen Substances 0.000 claims 1
- 102000036639 antigens Human genes 0.000 claims 1
- 108091007433 antigens Proteins 0.000 claims 1
- 210000003719 b-lymphocyte Anatomy 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 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 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
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- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims 1
- 230000004968 inflammatory condition Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- ZHBQVNBWMUCVOE-UHFFFAOYSA-N methyl 3-(6-acetamidopyridin-3-yl)-4-chlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(C)=O)=CC=2)=C1 ZHBQVNBWMUCVOE-UHFFFAOYSA-N 0.000 claims 1
- FNHWRICEGXQSGK-UHFFFAOYSA-N methyl 3-[4-(butanoylamino)phenyl]-4-ethylbenzoate Chemical compound C1=CC(NC(=O)CCC)=CC=C1C1=CC(C(=O)OC)=CC=C1CC FNHWRICEGXQSGK-UHFFFAOYSA-N 0.000 claims 1
- YYHOXNXGCQFEIQ-UHFFFAOYSA-N methyl 3-[4-(butanoylamino)phenyl]-4-methylbenzoate Chemical compound C1=CC(NC(=O)CCC)=CC=C1C1=CC(C(=O)OC)=CC=C1C YYHOXNXGCQFEIQ-UHFFFAOYSA-N 0.000 claims 1
- CJPNFYWKANCPSV-UHFFFAOYSA-N methyl 3-[4-(butylamino)phenyl]-4-methylbenzoate Chemical compound C1=CC(NCCCC)=CC=C1C1=CC(C(=O)OC)=CC=C1C CJPNFYWKANCPSV-UHFFFAOYSA-N 0.000 claims 1
- WCKXPANLJRBKGI-UHFFFAOYSA-N methyl 3-[6-(butanoylamino)pyridin-3-yl]-4-chlorobenzoate Chemical compound C1=NC(NC(=O)CCC)=CC=C1C1=CC(C(=O)OC)=CC=C1Cl WCKXPANLJRBKGI-UHFFFAOYSA-N 0.000 claims 1
- CJRXBXIWPHBQBI-UHFFFAOYSA-N methyl 4-bromo-3-[4-(2-methylpropanoylamino)phenyl]benzoate Chemical compound COC(=O)C1=CC=C(Br)C(C=2C=CC(NC(=O)C(C)C)=CC=2)=C1 CJRXBXIWPHBQBI-UHFFFAOYSA-N 0.000 claims 1
- CXIUEHWAYNODAW-UHFFFAOYSA-N methyl 4-bromo-3-[4-(butanoylamino)phenyl]benzoate Chemical compound C1=CC(NC(=O)CCC)=CC=C1C1=CC(C(=O)OC)=CC=C1Br CXIUEHWAYNODAW-UHFFFAOYSA-N 0.000 claims 1
- HAKOOVWTWUZQLS-UHFFFAOYSA-N methyl 4-bromo-3-[4-(prop-2-enoylamino)phenyl]benzoate Chemical compound COC(=O)C1=CC=C(Br)C(C=2C=CC(NC(=O)C=C)=CC=2)=C1 HAKOOVWTWUZQLS-UHFFFAOYSA-N 0.000 claims 1
- BAERRFKVJZQYCH-UHFFFAOYSA-N methyl 4-bromo-3-[4-(propanoylamino)phenyl]benzoate Chemical compound C1=CC(NC(=O)CC)=CC=C1C1=CC(C(=O)OC)=CC=C1Br BAERRFKVJZQYCH-UHFFFAOYSA-N 0.000 claims 1
- VHPSJRFRHHQART-UHFFFAOYSA-N methyl 4-chloro-3-[6-(cyclobutanecarbonylamino)pyridin-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(=O)C3CCC3)=CC=2)=C1 VHPSJRFRHHQART-UHFFFAOYSA-N 0.000 claims 1
- WHHCNQQGQVOEND-UHFFFAOYSA-N methyl 4-chloro-3-[6-(cyclohexanecarbonylamino)pyridin-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(=O)C3CCCCC3)=CC=2)=C1 WHHCNQQGQVOEND-UHFFFAOYSA-N 0.000 claims 1
- MMUHITYCEITFFT-UHFFFAOYSA-N methyl 4-chloro-3-[6-(cyclopentanecarbonylamino)pyridin-3-yl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2C=NC(NC(=O)C3CCCC3)=CC=2)=C1 MMUHITYCEITFFT-UHFFFAOYSA-N 0.000 claims 1
- ZZIXVVIFAKRTDE-UHFFFAOYSA-N methyl 4-chloro-3-[6-(propanoylamino)pyridin-3-yl]benzoate Chemical compound C1=NC(NC(=O)CC)=CC=C1C1=CC(C(=O)OC)=CC=C1Cl ZZIXVVIFAKRTDE-UHFFFAOYSA-N 0.000 claims 1
- VSGMHGMKHOJHKD-UHFFFAOYSA-N methyl 4-ethyl-3-[4-(2-methylpropanoylamino)phenyl]benzoate Chemical compound CCC1=CC=C(C(=O)OC)C=C1C1=CC=C(NC(=O)C(C)C)C=C1 VSGMHGMKHOJHKD-UHFFFAOYSA-N 0.000 claims 1
- CWHBCPHYUBWQSV-UHFFFAOYSA-N methyl 4-ethyl-3-[4-(prop-2-enoylamino)phenyl]benzoate Chemical compound CCC1=CC=C(C(=O)OC)C=C1C1=CC=C(NC(=O)C=C)C=C1 CWHBCPHYUBWQSV-UHFFFAOYSA-N 0.000 claims 1
- GQNWJVKKCYOJCH-UHFFFAOYSA-N methyl 4-ethyl-3-[4-(propanoylamino)phenyl]benzoate Chemical compound C1=CC(NC(=O)CC)=CC=C1C1=CC(C(=O)OC)=CC=C1CC GQNWJVKKCYOJCH-UHFFFAOYSA-N 0.000 claims 1
- RPGZDCNYJQTYKN-UHFFFAOYSA-N methyl 4-methyl-3-[4-(2-methylpropanoylamino)phenyl]benzoate Chemical compound COC(=O)C1=CC=C(C)C(C=2C=CC(NC(=O)C(C)C)=CC=2)=C1 RPGZDCNYJQTYKN-UHFFFAOYSA-N 0.000 claims 1
- WPOKUKYNGRUICD-UHFFFAOYSA-N methyl 4-methyl-3-[4-(prop-2-enoylamino)phenyl]benzoate Chemical compound COC(=O)C1=CC=C(C)C(C=2C=CC(NC(=O)C=C)=CC=2)=C1 WPOKUKYNGRUICD-UHFFFAOYSA-N 0.000 claims 1
- PFZBNVIAPKLWOU-UHFFFAOYSA-N methyl 4-methyl-3-[4-(propanoylamino)phenyl]benzoate Chemical compound C1=CC(NC(=O)CC)=CC=C1C1=CC(C(=O)OC)=CC=C1C PFZBNVIAPKLWOU-UHFFFAOYSA-N 0.000 claims 1
- KRSFXPLAAMWTLR-UHFFFAOYSA-N n-[4-[2-bromo-5-(1,3-oxazol-2-yl)phenyl]phenyl]-2-methylpropanamide Chemical compound C1=CC(NC(=O)C(C)C)=CC=C1C1=CC(C=2OC=CN=2)=CC=C1Br KRSFXPLAAMWTLR-UHFFFAOYSA-N 0.000 claims 1
- KMABCLPYFRXSSD-UHFFFAOYSA-N n-[4-[2-bromo-5-(1,3-oxazol-2-yl)phenyl]phenyl]butanamide Chemical compound C1=CC(NC(=O)CCC)=CC=C1C1=CC(C=2OC=CN=2)=CC=C1Br KMABCLPYFRXSSD-UHFFFAOYSA-N 0.000 claims 1
- HCBSBVLZPWIIBX-UHFFFAOYSA-N n-[4-[2-bromo-5-(1,3-oxazol-2-yl)phenyl]phenyl]prop-2-enamide Chemical compound BrC1=CC=C(C=2OC=CN=2)C=C1C1=CC=C(NC(=O)C=C)C=C1 HCBSBVLZPWIIBX-UHFFFAOYSA-N 0.000 claims 1
- KTXZLMNGAKEKNM-UHFFFAOYSA-N n-[4-[2-bromo-5-(1,3-oxazol-2-yl)phenyl]phenyl]propanamide Chemical compound C1=CC(NC(=O)CC)=CC=C1C1=CC(C=2OC=CN=2)=CC=C1Br KTXZLMNGAKEKNM-UHFFFAOYSA-N 0.000 claims 1
- BRMJWCXGHCUXIT-UHFFFAOYSA-N n-[4-[2-bromo-5-(1,3-thiazol-2-yl)phenyl]phenyl]-2-methylpropanamide Chemical compound C1=CC(NC(=O)C(C)C)=CC=C1C1=CC(C=2SC=CN=2)=CC=C1Br BRMJWCXGHCUXIT-UHFFFAOYSA-N 0.000 claims 1
- QIOIFFGTWVRGTF-UHFFFAOYSA-N n-[4-[2-bromo-5-(1,3-thiazol-2-yl)phenyl]phenyl]butanamide Chemical compound C1=CC(NC(=O)CCC)=CC=C1C1=CC(C=2SC=CN=2)=CC=C1Br QIOIFFGTWVRGTF-UHFFFAOYSA-N 0.000 claims 1
- DATYLLCVGYCDJP-UHFFFAOYSA-N n-[4-[2-bromo-5-(1,3-thiazol-2-yl)phenyl]phenyl]prop-2-enamide Chemical compound BrC1=CC=C(C=2SC=CN=2)C=C1C1=CC=C(NC(=O)C=C)C=C1 DATYLLCVGYCDJP-UHFFFAOYSA-N 0.000 claims 1
- YUMWOVIJIDUVNT-UHFFFAOYSA-N n-[4-[2-bromo-5-(1,3-thiazol-2-yl)phenyl]phenyl]propanamide Chemical compound C1=CC(NC(=O)CC)=CC=C1C1=CC(C=2SC=CN=2)=CC=C1Br YUMWOVIJIDUVNT-UHFFFAOYSA-N 0.000 claims 1
- DSWBLNDHIVATNB-UHFFFAOYSA-N n-[4-[2-chloro-5-(1,3-oxazol-2-yl)phenyl]phenyl]-2-methylpropanamide Chemical compound C1=CC(NC(=O)C(C)C)=CC=C1C1=CC(C=2OC=CN=2)=CC=C1Cl DSWBLNDHIVATNB-UHFFFAOYSA-N 0.000 claims 1
- WBZLFONKRYXOQS-UHFFFAOYSA-N n-[4-[2-chloro-5-(1,3-oxazol-2-yl)phenyl]phenyl]butanamide Chemical compound C1=CC(NC(=O)CCC)=CC=C1C1=CC(C=2OC=CN=2)=CC=C1Cl WBZLFONKRYXOQS-UHFFFAOYSA-N 0.000 claims 1
- AVFYTESMTZBFMI-UHFFFAOYSA-N n-[4-[2-chloro-5-(1,3-oxazol-2-yl)phenyl]phenyl]prop-2-enamide Chemical compound ClC1=CC=C(C=2OC=CN=2)C=C1C1=CC=C(NC(=O)C=C)C=C1 AVFYTESMTZBFMI-UHFFFAOYSA-N 0.000 claims 1
- PLLKNLFMKWJVHA-UHFFFAOYSA-N n-[4-[2-chloro-5-(1,3-oxazol-2-yl)phenyl]phenyl]propanamide Chemical compound C1=CC(NC(=O)CC)=CC=C1C1=CC(C=2OC=CN=2)=CC=C1Cl PLLKNLFMKWJVHA-UHFFFAOYSA-N 0.000 claims 1
- QIUSZRIJYLSPIF-UHFFFAOYSA-N n-[4-[2-chloro-5-(1,3-thiazol-2-yl)phenyl]phenyl]-2-methylpropanamide Chemical compound C1=CC(NC(=O)C(C)C)=CC=C1C1=CC(C=2SC=CN=2)=CC=C1Cl QIUSZRIJYLSPIF-UHFFFAOYSA-N 0.000 claims 1
- IZUHMHCAVKBIBV-UHFFFAOYSA-N n-[4-[2-chloro-5-(1,3-thiazol-2-yl)phenyl]phenyl]butanamide Chemical compound C1=CC(NC(=O)CCC)=CC=C1C1=CC(C=2SC=CN=2)=CC=C1Cl IZUHMHCAVKBIBV-UHFFFAOYSA-N 0.000 claims 1
- RGDQVNHNXHEWBW-UHFFFAOYSA-N n-[4-[2-chloro-5-(1,3-thiazol-2-yl)phenyl]phenyl]prop-2-enamide Chemical compound ClC1=CC=C(C=2SC=CN=2)C=C1C1=CC=C(NC(=O)C=C)C=C1 RGDQVNHNXHEWBW-UHFFFAOYSA-N 0.000 claims 1
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- UJYVGDUOPWAWKN-UHFFFAOYSA-N n-[4-[2-chloro-5-(trifluoromethyl)phenyl]phenyl]-1-methylpyrrolidine-2-carboxamide Chemical compound CN1CCCC1C(=O)NC1=CC=C(C=2C(=CC=C(C=2)C(F)(F)F)Cl)C=C1 UJYVGDUOPWAWKN-UHFFFAOYSA-N 0.000 claims 1
- FMICPAKZTYANDY-UHFFFAOYSA-N n-[4-[2-chloro-5-(trifluoromethyl)phenyl]phenyl]bicyclo[2.2.1]heptane-3-carboxamide Chemical compound FC(F)(F)C1=CC=C(Cl)C(C=2C=CC(NC(=O)C3C4CCC(C4)C3)=CC=2)=C1 FMICPAKZTYANDY-UHFFFAOYSA-N 0.000 claims 1
- DVKDBLQLDFVGRX-UHFFFAOYSA-N n-[4-[2-chloro-5-(trifluoromethyl)phenyl]phenyl]cyclohex-3-ene-1-carboxamide Chemical compound FC(F)(F)C1=CC=C(Cl)C(C=2C=CC(NC(=O)C3CC=CCC3)=CC=2)=C1 DVKDBLQLDFVGRX-UHFFFAOYSA-N 0.000 claims 1
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- AVRVXMIEPVTKKS-UHFFFAOYSA-N n-[4-[2-chloro-5-(trifluoromethyl)phenyl]phenyl]piperidine-4-carboxamide Chemical compound FC(F)(F)C1=CC=C(Cl)C(C=2C=CC(NC(=O)C3CCNCC3)=CC=2)=C1 AVRVXMIEPVTKKS-UHFFFAOYSA-N 0.000 claims 1
- KNRNNSJUECXXQE-UHFFFAOYSA-N n-[4-[2-chloro-5-(trifluoromethyl)phenyl]phenyl]pyrrolidine-2-carboxamide Chemical compound FC(F)(F)C1=CC=C(Cl)C(C=2C=CC(NC(=O)C3NCCC3)=CC=2)=C1 KNRNNSJUECXXQE-UHFFFAOYSA-N 0.000 claims 1
- ZNBNOZQRBNYCLY-UHFFFAOYSA-N n-[4-[2-ethyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]-2-methylpropanamide Chemical compound CCC1=CC=C(C=2OC=CN=2)C=C1C1=CC=C(NC(=O)C(C)C)C=C1 ZNBNOZQRBNYCLY-UHFFFAOYSA-N 0.000 claims 1
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- HXTUISIIRAMAIQ-UHFFFAOYSA-N n-[4-[2-iodo-5-(1,3-thiazol-2-yl)phenyl]phenyl]prop-2-enamide Chemical compound IC1=CC=C(C=2SC=CN=2)C=C1C1=CC=C(NC(=O)C=C)C=C1 HXTUISIIRAMAIQ-UHFFFAOYSA-N 0.000 claims 1
- LWGYSPMNKFMSHC-UHFFFAOYSA-N n-[4-[2-iodo-5-(1,3-thiazol-2-yl)phenyl]phenyl]propanamide Chemical compound C1=CC(NC(=O)CC)=CC=C1C1=CC(C=2SC=CN=2)=CC=C1I LWGYSPMNKFMSHC-UHFFFAOYSA-N 0.000 claims 1
- LRLKKVYRBJIQGP-UHFFFAOYSA-N n-[4-[2-methoxy-5-(1,3-thiazol-2-yl)phenyl]phenyl]-2-methylpropanamide Chemical compound COC1=CC=C(C=2SC=CN=2)C=C1C1=CC=C(NC(=O)C(C)C)C=C1 LRLKKVYRBJIQGP-UHFFFAOYSA-N 0.000 claims 1
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- IXRNBIVPEIDKAE-UHFFFAOYSA-N n-[4-[2-methoxy-5-(1,3-thiazol-2-yl)phenyl]phenyl]prop-2-enamide Chemical compound COC1=CC=C(C=2SC=CN=2)C=C1C1=CC=C(NC(=O)C=C)C=C1 IXRNBIVPEIDKAE-UHFFFAOYSA-N 0.000 claims 1
- FODLWILYRCYELZ-UHFFFAOYSA-N n-[4-[2-methoxy-5-(1,3-thiazol-2-yl)phenyl]phenyl]propanamide Chemical compound C1=CC(NC(=O)CC)=CC=C1C1=CC(C=2SC=CN=2)=CC=C1OC FODLWILYRCYELZ-UHFFFAOYSA-N 0.000 claims 1
- YVOIHXQZYBTATL-UHFFFAOYSA-N n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]-2-(2-methylphenyl)acetamide Chemical compound CC1=CC=CC=C1CC(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=CN=2)C)C=C1 YVOIHXQZYBTATL-UHFFFAOYSA-N 0.000 claims 1
- MLVXYNXOYIUXJL-UHFFFAOYSA-N n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]-2-(3-methylpyridin-4-yl)acetamide Chemical compound CC1=CN=CC=C1CC(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=CN=2)C)C=C1 MLVXYNXOYIUXJL-UHFFFAOYSA-N 0.000 claims 1
- DEMNFLPKOHEILF-UHFFFAOYSA-N n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]-2-(4-methylphenyl)acetamide Chemical compound C1=CC(C)=CC=C1CC(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=CN=2)C)C=C1 DEMNFLPKOHEILF-UHFFFAOYSA-N 0.000 claims 1
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- XYNZGNDYQZMWBT-UHFFFAOYSA-N n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]-2-(4-nitrophenyl)acetamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)CC1=CC=C([N+]([O-])=O)C=C1 XYNZGNDYQZMWBT-UHFFFAOYSA-N 0.000 claims 1
- ILZDHFRAOVTCKQ-UHFFFAOYSA-N n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]-2-[3-(trifluoromethyl)phenyl]acetamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)CC1=CC=CC(C(F)(F)F)=C1 ILZDHFRAOVTCKQ-UHFFFAOYSA-N 0.000 claims 1
- IJZWSMCIQYVBLO-UHFFFAOYSA-N n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]-2-[4-(trifluoromethyl)phenyl]acetamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)CC1=CC=C(C(F)(F)F)C=C1 IJZWSMCIQYVBLO-UHFFFAOYSA-N 0.000 claims 1
- JRDVJSHMPVLHRA-UHFFFAOYSA-N n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]-2-phenylacetamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)CC1=CC=CC=C1 JRDVJSHMPVLHRA-UHFFFAOYSA-N 0.000 claims 1
- YNSKWXXHJQRYCD-UHFFFAOYSA-N n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]-3-(2,3,4-trimethoxyphenyl)prop-2-enamide Chemical compound COC1=C(OC)C(OC)=CC=C1C=CC(=O)NC1=CC=C(C=2C(=CC=C(C=2)C=2OC=CN=2)C)C=C1 YNSKWXXHJQRYCD-UHFFFAOYSA-N 0.000 claims 1
- YWOSMRGVMDKSJY-UHFFFAOYSA-N n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]-3-(2-nitrophenyl)prop-2-enamide Chemical compound CC1=CC=C(C=2OC=CN=2)C=C1C(C=C1)=CC=C1NC(=O)C=CC1=CC=CC=C1[N+]([O-])=O YWOSMRGVMDKSJY-UHFFFAOYSA-N 0.000 claims 1
- DWYIJDHEEXJKFS-UHFFFAOYSA-N n-[4-[2-methyl-5-(1,3-oxazol-2-yl)phenyl]phenyl]-3-(3,4,5-trimethoxyphenyl)prop-2-enamide Chemical compound COC1=C(OC)C(OC)=CC(C=CC(=O)NC=2C=CC(=CC=2)C=2C(=CC=C(C=2)C=2OC=CN=2)C)=C1 DWYIJDHEEXJKFS-UHFFFAOYSA-N 0.000 claims 1
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| JP2008531596A (ja) * | 2005-02-25 | 2008-08-14 | ライジェル ファーマシューティカルズ， インコーポレイテッド | Ｈｃｖ感染を治療または予防するのに有用なベンゾイソチアゾール |
| PL1860941T3 (pl) * | 2005-03-16 | 2009-04-30 | Basf Se | Bifenylo-n-(4-pirydylo)metylosulfonoamidy |
| KR20080031379A (ko) * | 2005-07-11 | 2008-04-08 | 와이어쓰 | 글루타메이트 아그레카나제 저해제 |
| EP1912970A2 (en) * | 2005-08-10 | 2008-04-23 | Bayer Schering Pharma Aktiengesellschaft | Acyltryptophanols for fertility control |
| WO2007087443A2 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Vinyl-phenyl derivatives for inflammation and immune-related uses |
| CA2639910A1 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Thiazole and thiadiazole compounds for inflammation and immune-related uses |
| US20070275960A1 (en) * | 2006-01-25 | 2007-11-29 | Synta Pharmaceuticals Corp. | Phenyl and pyridyl compounds for inflammation and immune-related uses |
| WO2007087441A2 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Substituted aromatic compounds for inflammation and immune-related uses |
| US20070254926A1 (en) * | 2006-01-31 | 2007-11-01 | Jun Jiang | Pyridylphenyl compounds for inflammation and immune-related uses |
| US8119643B2 (en) * | 2006-03-20 | 2012-02-21 | Synta Pharmaceuticals Corp. | Benzoimidazolyl-pyrazine compounds for inflammation and immune-related uses |
| US8163777B2 (en) * | 2006-03-23 | 2012-04-24 | Synta Pharmaceuticals Corp. | Benzimidazolyl-pyridine compounds for inflammation and immune-related uses |
| US8779154B2 (en) * | 2006-09-26 | 2014-07-15 | Qinglin Che | Fused ring compounds for inflammation and immune-related uses |
| CA2669695C (en) * | 2006-11-13 | 2012-10-30 | Synta Pharmaceuticals Corp. | Tetrahydropyridinyl compounds for inflammation and immune-related uses |
| EP2129219A4 (en) | 2007-02-16 | 2012-08-29 | Synta Pharmaceuticals Corp | SUBSTITUTED FUSED CYCLE COMPOUNDS USED IN CASES OF INFLAMMATION OR IMMUNE DISORDERS |
| TW200911800A (en) | 2007-08-01 | 2009-03-16 | Synta Pharmaceuticals Corp | Pyridine compounds for inflammation and immune-related uses |
| EP2184994B1 (en) | 2007-08-01 | 2013-09-25 | Synta Pharmaceuticals Corp. | Heterocycle-aryl compounds for inflammation and immune-related uses |
| US8349841B2 (en) | 2007-08-01 | 2013-01-08 | Synta Pharmaceuticals Corp. | Vinyl-aryl derivatives for inflammation and immune-related uses |
| US8324219B2 (en) | 2007-09-20 | 2012-12-04 | Synta Pharmaceuticals Corp. | Substituted benzoimidazolyl-pyrazine compounds for inflammation and immune-related uses |
| EP2240029A4 (en) | 2008-01-07 | 2012-08-22 | Synta Pharmaceuticals Corp | COMPOUNDS FOR USE AGAINST INFLAMMATORY AND IMMUNOMIC DISEASES |
-
2007
- 2007-01-25 WO PCT/US2007/002306 patent/WO2007087442A2/en not_active Ceased
- 2007-01-25 JP JP2008552473A patent/JP2009528273A/ja not_active Ceased
- 2007-01-25 US US11/698,781 patent/US8623871B2/en not_active Expired - Fee Related
- 2007-01-25 EP EP07762586A patent/EP1998612A4/en not_active Withdrawn
- 2007-01-25 AU AU2007208240A patent/AU2007208240B2/en not_active Ceased
- 2007-01-25 CA CA002639927A patent/CA2639927A1/en not_active Abandoned
- 2007-01-25 TW TW096102791A patent/TW200806290A/zh unknown
-
2014
- 2014-01-02 US US14/146,415 patent/US20140121217A1/en not_active Abandoned
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