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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Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1706392A2 (en) * | 2004-01-08 | 2006-10-04 | Syngenta Participations AG | Pesticidal heterocyclic dihaloallyl compounds |
| WO2006081389A1 (en) * | 2005-01-25 | 2006-08-03 | Synta Pharmaceuticals Corp. | Thiophene compounds for inflammation and immune-related uses |
| CA2640090A1 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Substituted aromatic compounds for inflammation and immune-related uses |
| CA2639913A1 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceutical Corp. | Phenyl and pyridyl compounds for inflammation and immune-related uses |
| WO2007087443A2 (en) | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Vinyl-phenyl derivatives for inflammation and immune-related uses |
| JP2009524677A (ja) * | 2006-01-25 | 2009-07-02 | シンタ ファーマシューティカルズ コーポレーション | 炎症および免疫関連使用用のチアゾールおよびチアジアゾール化合物 |
| AU2007211276B2 (en) * | 2006-01-31 | 2013-06-06 | Synta Pharmaceuticals Corp. | Pyridylphenyl compounds for inflammation and immune-related uses |
| CA2645434A1 (en) | 2006-03-20 | 2007-09-27 | Synta Pharmaceutical Corp. | Benzoimidazolyl-parazine compounds for inflammation and immune-related uses |
| US8633175B2 (en) | 2006-08-09 | 2014-01-21 | Glaxosmithkline Llc | Compounds as antagonists or inverse agonists at opioid receptors |
| US8779154B2 (en) * | 2006-09-26 | 2014-07-15 | Qinglin Che | Fused ring compounds for inflammation and immune-related uses |
| EA015952B1 (ru) | 2007-05-03 | 2011-12-30 | Пфайзер Лимитед | 2-пиридинкарбоксамидные производные в качестве модуляторов натриевых каналов |
| RU2465272C2 (ru) | 2007-09-10 | 2012-10-27 | КалсиМедика, Инк. | Соединения, моделирующие внутриклеточный кальций |
| US20090148530A1 (en) * | 2007-12-08 | 2009-06-11 | Jamie Koufman | Method for prevention and treatment of reflux injury in the aerodigestive tract and laryngopharynx caused by pepsin |
| WO2009076454A2 (en) * | 2007-12-12 | 2009-06-18 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| CA2734500A1 (en) | 2008-08-27 | 2010-03-11 | Calcimedica Inc. | Compounds that modulate intracellular calcium |
| US8524763B2 (en) * | 2008-09-22 | 2013-09-03 | Calcimedica, Inc. | Inhibitors of store operated calcium release |
| US8143269B2 (en) * | 2008-10-03 | 2012-03-27 | Calcimedica, Inc. | Inhibitors of store operated calcium release |
| US8618307B2 (en) * | 2009-09-16 | 2013-12-31 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US8993612B2 (en) | 2009-10-08 | 2015-03-31 | Rhizen Pharmaceuticals Sa | Modulators of calcium release-activated calcium channel and methods for treatment of non-small cell lung cancer |
| US8377970B2 (en) | 2009-10-08 | 2013-02-19 | Rhizen Pharmaceuticals Sa | Modulators of calcium release-activated calcium channel |
| US10703722B2 (en) | 2010-04-27 | 2020-07-07 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| EP2563759B1 (en) | 2010-04-27 | 2022-04-06 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| JP6112486B2 (ja) | 2010-04-27 | 2017-04-12 | カルシメディカ，インク． | 細胞内カルシウムを調節する化合物 |
| CN103180316A (zh) | 2010-08-27 | 2013-06-26 | 钙医学公司 | 调节细胞内钙的化合物 |
| CN102010398B (zh) | 2010-10-20 | 2011-11-30 | 中国科学院昆明植物研究所 | 含氮类联苯化合物,含其的药物组合物,其制备方法及其在抗hiv-1中的应用 |
| AP3341A (en) | 2010-10-30 | 2015-07-31 | Lupin Ltd | Oxazoline and isoxazoline derivatives as crac modulators |
| WO2012170931A2 (en) | 2011-06-10 | 2012-12-13 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| WO2013059677A1 (en) | 2011-10-19 | 2013-04-25 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| EP2844655A1 (en) | 2012-05-02 | 2015-03-11 | Lupin Limited | Substituted pyridine compounds as crac modulators |
| AU2013255441B2 (en) | 2012-05-02 | 2017-11-09 | Lupin Limited | Substituted pyrazole compounds as CRAC modulators |
| WO2014059333A1 (en) | 2012-10-12 | 2014-04-17 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US9725463B2 (en) | 2013-06-21 | 2017-08-08 | Lupin Limited | Substituted heterocyclic compounds as CRAC modulators |
| EP3013810A1 (en) | 2013-06-24 | 2016-05-04 | Lupin Limited | Chromane and chromene derivatives and their use as crac modulators |
| DE102014203011A1 (de) * | 2014-02-19 | 2015-08-20 | Beiersdorf Ag | Kosmetische oder dermatologische Zubereitungen mit einem Gehalt an einem oder mehreren Biphenylamin-Derivaten und Verwendung von einem oder mehreren Biphenylamin-Derivaten zur Bräunung der Haut |
| TWI771269B (zh) | 2015-02-27 | 2022-07-21 | 美商鈣系醫藥公司 | 胰腺炎治療 |
| CN107847548B (zh) | 2015-05-18 | 2022-06-14 | 贝思以色列女会吏医学中心公司 | P物质、肥大细胞脱颗粒抑制剂和周围神经病 |
| CA2995094A1 (en) | 2015-08-07 | 2017-02-16 | Calcimedica, Inc. | Use of crac channel inhibitors for the treatment of stroke and traumatic brain injury |
| TWI691486B (zh) * | 2016-01-29 | 2020-04-21 | 日商東麗股份有限公司 | 環狀胺衍生物及其醫藥用途 |
| JP2022508468A (ja) | 2018-09-14 | 2022-01-19 | ルヒゼン ファーマスティカルズ アクツィエンゲゼルシャフト | Ｃｒａｃ阻害剤およびコルチコステロイドを含む組成物ならびにそれらの使用方法 |
| KR102286897B1 (ko) * | 2019-06-25 | 2021-08-09 | (주)앰틱스바이오 | 신규한 아미노알칸산에 바이페닐기를 도입한 유도체 화합물 및 이를 포함하는 항진균성 약학적 조성물 |
| US12486274B2 (en) | 2020-01-13 | 2025-12-02 | Verge Analytics, Inc. | Substituted pyrazolo-pyrimidines and uses thereof |
| CA3172249A1 (en) | 2020-03-20 | 2021-09-23 | Calcimedica, Inc. | Methods and compositions for treating acute lung injury and acute respiratory distress syndrome |
| US20230192631A1 (en) * | 2020-04-16 | 2023-06-22 | Hoffmann-La Roche Inc. | Biphenyl Derivatives |
| JP7791898B2 (ja) | 2020-11-13 | 2025-12-24 | カルシメディカ，インク． | Ｃｒａｃチャネル阻害剤の合成の改善 |
| AU2021408790B2 (en) * | 2020-12-25 | 2025-12-18 | Amtixbio Co., Ltd. | Novel derivative compound having biphenyl group introduced into amino-alkanoic acid and anti-inflammatory composition comprising same |
| EP4351560A4 (en) * | 2021-06-08 | 2025-06-04 | The Regents of the University of California | ANTI-CANCER COMPOUNDS |
Family Cites Families (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3022166A (en) * | 1957-03-28 | 1962-02-20 | Polaroid Corp | Photographic products, processes and compositions |
| US3536809A (en) | 1969-02-17 | 1970-10-27 | Alza Corp | Medication method |
| US3598123A (en) | 1969-04-01 | 1971-08-10 | Alza Corp | Bandage for administering drugs |
| US3845770A (en) | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| US3916899A (en) | 1973-04-25 | 1975-11-04 | Alza Corp | Osmotic dispensing device with maximum and minimum sizes for the passageway |
| US4008719A (en) | 1976-02-02 | 1977-02-22 | Alza Corporation | Osmotic system having laminar arrangement for programming delivery of active agent |
| IE58110B1 (en) | 1984-10-30 | 1993-07-14 | Elan Corp Plc | Controlled release powder and process for its preparation |
| US5073543A (en) | 1988-07-21 | 1991-12-17 | G. D. Searle & Co. | Controlled release formulations of trophic factors in ganglioside-lipsome vehicle |
| IT1229203B (it) | 1989-03-22 | 1991-07-25 | Bioresearch Spa | Impiego di acido 5 metiltetraidrofolico, di acido 5 formiltetraidrofolico e dei loro sali farmaceuticamente accettabili per la preparazione di composizioni farmaceutiche in forma a rilascio controllato attive nella terapia dei disturbi mentali organici e composizioni farmaceutiche relative. |
| US5120548A (en) | 1989-11-07 | 1992-06-09 | Merck & Co., Inc. | Swelling modulated polymeric drug delivery device |
| US5733566A (en) | 1990-05-15 | 1998-03-31 | Alkermes Controlled Therapeutics Inc. Ii | Controlled release of antiparasitic agents in animals |
| US5580578A (en) | 1992-01-27 | 1996-12-03 | Euro-Celtique, S.A. | Controlled release formulations coated with aqueous dispersions of acrylic polymers |
| US5591767A (en) | 1993-01-25 | 1997-01-07 | Pharmetrix Corporation | Liquid reservoir transdermal patch for the administration of ketorolac |
| FR2708609B1 (fr) * | 1993-07-29 | 1995-10-20 | Sanofi Elf | Dérivés de méthylguanidine, leurs procédés de préparation ainsi que les compositions en contenant. |
| IT1270594B (it) | 1994-07-07 | 1997-05-07 | Recordati Chem Pharm | Composizione farmaceutica a rilascio controllato di moguisteina in sospensione liquida |
| US6274171B1 (en) | 1996-03-25 | 2001-08-14 | American Home Products Corporation | Extended release formulation of venlafaxine hydrochloride |
| US6458806B1 (en) * | 1996-08-15 | 2002-10-01 | Millennium Pharmaceuticals, Inc. | Aryl alkenamides derivatives as MCP-1 antagonists |
| US6677488B2 (en) * | 1997-11-17 | 2004-01-13 | G.D. Searle & Co. | Substituted biphenyl compounds for the treatment of inflammation |
| MY153569A (en) * | 1998-01-20 | 2015-02-27 | Mitsubishi Tanabe Pharma Corp | Inhibitors of ?4 mediated cell adhesion |
| DE19822041A1 (de) | 1998-05-16 | 1999-12-23 | Wella Ag | 2,5-Diamino-1-phenylbenzol-Derivate enthaltende Oxidationshaarfärbemittel sowie neue 2,5-Diamino-1-phenylbenzol-Derivate |
| CA2426430C (en) | 2000-10-20 | 2014-10-07 | Biocryst Pharmaceuticals, Inc. | Biaryl compounds as serine protease inhibitors |
| US20040087620A1 (en) * | 2001-01-18 | 2004-05-06 | Tatsuo Tsuri | Terphenyl compounds bearing substituted amino groups |
| DE60139510D1 (de) * | 2001-04-06 | 2009-09-17 | Biocryst Pharm Inc | Biarylverbindungen als serinproteaseinhibitoren |
| CN1668287B (zh) * | 2001-09-06 | 2012-03-28 | 赛诺克思公司 | 3-脱氧类黄酮在制备抑制t淋巴细胞活性的药物中的用途 |
| GB0124932D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124938D0 (en) | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| GB0124936D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| US6867320B2 (en) * | 2002-02-21 | 2005-03-15 | Asahi Kasei Pharma Corporation | Substituted phenylalkanoic acid derivatives and use thereof |
| EP1503997A1 (en) | 2002-05-14 | 2005-02-09 | Axys Pharmaceuticals, Inc. | Cysteine protease inhibitors |
| US6908935B2 (en) | 2002-05-23 | 2005-06-21 | Amgen Inc. | Calcium receptor modulating agents |
| US20060122184A1 (en) * | 2002-12-05 | 2006-06-08 | Axys Pharmaceuticals, Inc. | Cyanomethyl derivatives as cysteine protease inhibitors |
| SE0300010D0 (sv) * | 2003-01-07 | 2003-01-07 | Astrazeneca Ab | Novel Compounds |
| SE0301010D0 (sv) * | 2003-04-07 | 2003-04-07 | Astrazeneca Ab | Novel compounds |
| US6919483B2 (en) * | 2003-05-23 | 2005-07-19 | Mediquest Therapeutics, Inc. | Immunomodulation with novel pharmaceutical compositions |
| NZ545447A (en) * | 2003-07-23 | 2010-03-26 | Synta Pharmaceuticals Corp | Compounds for inflammation and immune-related uses |
| US20050090191A1 (en) * | 2003-10-22 | 2005-04-28 | Sun Yung Y. | Pneumatic handheld grinding apparatus |
| KR101195801B1 (ko) | 2004-06-18 | 2012-11-05 | 밀레니엄 파머슈티컬스 인코퍼레이티드 | Ｘａ 인자 억제제 |
| US20070275968A1 (en) * | 2004-09-07 | 2007-11-29 | Hitoshi Kurata | Substituted Biphenyl Derivative |
| JP2006104191A (ja) * | 2004-09-07 | 2006-04-20 | Sankyo Co Ltd | 置換ビフェニル誘導体 |
| KR20070057965A (ko) * | 2004-09-21 | 2007-06-07 | 신타 파마슈티칼스 코프. | 염증 및 면역 관련 용도를 위한 화합물 |
| KR101316992B1 (ko) * | 2004-12-23 | 2013-10-11 | 갈데르마 리써어치 앤드 디벨로프먼트 | Ｒａｒ 수용체를 조절하는 신규 리간드, 및 인간 의학 및화장품에서의 그의 용도 |
| WO2006083477A2 (en) * | 2005-01-07 | 2006-08-10 | Synta Pharmaceuticals Corp. | Compounds for inflammation and immune-related uses |
| AU2006208045B2 (en) * | 2005-01-25 | 2012-08-30 | Synta Pharmaceuticals Corp. | Compounds for inflammation and immune-related uses |
| WO2006081389A1 (en) * | 2005-01-25 | 2006-08-03 | Synta Pharmaceuticals Corp. | Thiophene compounds for inflammation and immune-related uses |
| CA2598043A1 (en) * | 2005-02-25 | 2006-08-31 | Rigel Pharmaceuticals, Inc. | Benzisothiazoles useful for treating or preventing hcv infection |
| EP1860941B1 (en) * | 2005-03-16 | 2008-11-12 | Basf Se | Biphenyl-n-(4-pyridyl) methylsufonamides |
| MY144590A (en) * | 2005-07-11 | 2011-10-14 | Wyeth Corp | Glutamate aggrecanase inhibitors |
| EP1912970A2 (en) * | 2005-08-10 | 2008-04-23 | Bayer Schering Pharma Aktiengesellschaft | Acyltryptophanols for fertility control |
| CA2639913A1 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceutical Corp. | Phenyl and pyridyl compounds for inflammation and immune-related uses |
| JP2009524677A (ja) * | 2006-01-25 | 2009-07-02 | シンタ ファーマシューティカルズ コーポレーション | 炎症および免疫関連使用用のチアゾールおよびチアジアゾール化合物 |
| WO2007087443A2 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Vinyl-phenyl derivatives for inflammation and immune-related uses |
| CA2640090A1 (en) * | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Substituted aromatic compounds for inflammation and immune-related uses |
| AU2007211276B2 (en) * | 2006-01-31 | 2013-06-06 | Synta Pharmaceuticals Corp. | Pyridylphenyl compounds for inflammation and immune-related uses |
| CA2645434A1 (en) * | 2006-03-20 | 2007-09-27 | Synta Pharmaceutical Corp. | Benzoimidazolyl-parazine compounds for inflammation and immune-related uses |
| AU2007230911A1 (en) * | 2006-03-23 | 2007-10-04 | 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 |
| EP2086326B1 (en) * | 2006-11-13 | 2014-01-08 | Synta Pharmaceuticals Corp. | Cyclohexenyl-aryl 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 |
| ES2440267T3 (es) | 2007-08-01 | 2014-01-28 | Synta Pharmaceuticals Corporation | Compuestos de heterociclo-arilo para la inflamación y usos inmunorrelacionados |
| TW200911800A (en) | 2007-08-01 | 2009-03-16 | Synta Pharmaceuticals Corp | Pyridine compounds for inflammation and immune-related uses |
| EP2185514A4 (en) | 2007-08-01 | 2011-05-18 | Synta Pharmaceuticals Corp | VINYL-ARYL DERIVATIVES FOR INFLAMMATORY AND IMMUNE DISORDERS |
| US8324219B2 (en) | 2007-09-20 | 2012-12-04 | Synta Pharmaceuticals Corp. | Substituted benzoimidazolyl-pyrazine compounds for inflammation and immune-related uses |
| US20110052643A1 (en) | 2008-01-07 | 2011-03-03 | Synta Pharmaceuticals Corp. | Compounds for inflammation and immune-related uses |
-
2007
- 2007-01-25 JP JP2008552473A patent/JP2009528273A/ja not_active Ceased
- 2007-01-25 EP EP07762586A patent/EP1998612A4/en not_active Withdrawn
- 2007-01-25 TW TW096102791A patent/TW200806290A/zh unknown
- 2007-01-25 CA CA002639927A patent/CA2639927A1/en not_active Abandoned
- 2007-01-25 WO PCT/US2007/002306 patent/WO2007087442A2/en not_active Ceased
- 2007-01-25 US US11/698,781 patent/US8623871B2/en not_active Expired - Fee Related
- 2007-01-25 AU AU2007208240A patent/AU2007208240B2/en not_active Ceased
-
2014
- 2014-01-02 US US14/146,415 patent/US20140121217A1/en not_active Abandoned
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