JP2016512194A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2016512194A5 JP2016512194A5 JP2015561540A JP2015561540A JP2016512194A5 JP 2016512194 A5 JP2016512194 A5 JP 2016512194A5 JP 2015561540 A JP2015561540 A JP 2015561540A JP 2015561540 A JP2015561540 A JP 2015561540A JP 2016512194 A5 JP2016512194 A5 JP 2016512194A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- bromophenyl
- optionally substituted
- carbamoyl
- alkyl
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims 46
- 229910052739 hydrogen Inorganic materials 0.000 claims 34
- 239000001257 hydrogen Substances 0.000 claims 33
- 150000002431 hydrogen Chemical class 0.000 claims 29
- 125000003118 aryl group Chemical group 0.000 claims 25
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 9
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 201000004624 Dermatitis Diseases 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 208000017520 skin disease Diseases 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- DMYSYIXHXMXWBW-UHFFFAOYSA-N 1-(4-bromophenyl)-3-(4-ethyl-2,5-dioxo-4-propan-2-ylimidazolidin-1-yl)urea Chemical compound O=C1C(CC)(C(C)C)NC(=O)N1NC(=O)NC1=CC=C(Br)C=C1 DMYSYIXHXMXWBW-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 208000000069 hyperpigmentation Diseases 0.000 claims 2
- 230000003810 hyperpigmentation Effects 0.000 claims 2
- 125000003367 polycyclic group Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 230000037390 scarring Effects 0.000 claims 2
- ZCVLAKQKEWQJAO-CQSZACIVSA-N (2r)-2-[(4-bromophenyl)carbamoylamino]-3-phenylpropanoic acid Chemical compound C([C@H](C(=O)O)NC(=O)NC=1C=CC(Br)=CC=1)C1=CC=CC=C1 ZCVLAKQKEWQJAO-CQSZACIVSA-N 0.000 claims 1
- ARFPPUXKLADSLY-CQSZACIVSA-N (2r)-2-[(4-iodophenyl)carbamoylamino]-3-phenylpropanoic acid Chemical compound C([C@H](C(=O)O)NC(=O)NC=1C=CC(I)=CC=1)C1=CC=CC=C1 ARFPPUXKLADSLY-CQSZACIVSA-N 0.000 claims 1
- DAIPOHPEAYKUFJ-JTQLQIEISA-N (2s)-2-[(4-bromo-2-fluorophenyl)carbamoylamino]-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)NC1=CC=C(Br)C=C1F DAIPOHPEAYKUFJ-JTQLQIEISA-N 0.000 claims 1
- IUIJFVKTIGTRLF-AWEZNQCLSA-N (2s)-2-[(4-bromo-2-fluorophenyl)carbamoylamino]-4-methyl-n-(2-oxopropyl)pentanamide Chemical compound CC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(Br)C=C1F IUIJFVKTIGTRLF-AWEZNQCLSA-N 0.000 claims 1
- ISXHVEOMRHCILC-INIZCTEOSA-N (2s)-2-[(4-bromo-2-fluorophenyl)carbamoylamino]-n-(2-hydroxyethyl)-3-phenylpropanamide Chemical compound C([C@@H](C(=O)NCCO)NC(=O)NC=1C(=CC(Br)=CC=1)F)C1=CC=CC=C1 ISXHVEOMRHCILC-INIZCTEOSA-N 0.000 claims 1
- BIPYNHXPZUAITO-KRWDZBQOSA-N (2s)-2-[(4-bromo-2-fluorophenyl)carbamoylamino]-n-(2-oxopropyl)-3-phenylpropanamide Chemical compound C([C@@H](C(=O)NCC(=O)C)NC(=O)NC=1C(=CC(Br)=CC=1)F)C1=CC=CC=C1 BIPYNHXPZUAITO-KRWDZBQOSA-N 0.000 claims 1
- MUTURHQUUWAQAJ-ZDUSSCGKSA-N (2s)-2-[(4-bromophenyl)carbamoylamino]-2-phenylacetic acid Chemical compound N([C@H](C(=O)O)C=1C=CC=CC=1)C(=O)NC1=CC=C(Br)C=C1 MUTURHQUUWAQAJ-ZDUSSCGKSA-N 0.000 claims 1
- VMEDZAKIZFAOJL-JTQLQIEISA-N (2s)-2-[(4-bromophenyl)carbamoylamino]-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)NC1=CC=C(Br)C=C1 VMEDZAKIZFAOJL-JTQLQIEISA-N 0.000 claims 1
- ZCVLAKQKEWQJAO-AWEZNQCLSA-N (2s)-2-[(4-bromophenyl)carbamoylamino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)NC=1C=CC(Br)=CC=1)C1=CC=CC=C1 ZCVLAKQKEWQJAO-AWEZNQCLSA-N 0.000 claims 1
- JLYOCBBJLCFPLC-AWEZNQCLSA-N (2s)-2-[(4-bromophenyl)carbamoylamino]-4-methyl-n-(2-oxopropyl)pentanamide Chemical compound CC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(Br)C=C1 JLYOCBBJLCFPLC-AWEZNQCLSA-N 0.000 claims 1
- WNZAMPDJJNIFRR-LBPRGKRZSA-N (2s)-2-[(4-bromophenyl)carbamoylamino]-4-methyl-n-(2h-tetrazol-5-ylmethyl)pentanamide Chemical compound N([C@@H](CC(C)C)C(=O)NCC=1NN=NN=1)C(=O)NC1=CC=C(Br)C=C1 WNZAMPDJJNIFRR-LBPRGKRZSA-N 0.000 claims 1
- WCGZSGWHOKVWEC-AWEZNQCLSA-N (2s)-2-[(4-bromophenyl)carbamoylamino]-4-methyl-n-[(3-oxo-1,2-oxazol-5-yl)methyl]pentanamide Chemical compound N([C@@H](CC(C)C)C(=O)NCC=1ON=C(O)C=1)C(=O)NC1=CC=C(Br)C=C1 WCGZSGWHOKVWEC-AWEZNQCLSA-N 0.000 claims 1
- HJRBAXCENNDVGX-AWEZNQCLSA-N (2s)-2-[(4-bromophenyl)carbamoylamino]-n-(1,3-dihydroxypropan-2-yl)-4-methylpentanamide Chemical compound OCC(CO)NC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(Br)C=C1 HJRBAXCENNDVGX-AWEZNQCLSA-N 0.000 claims 1
- MEHDWYDBOQKHNL-KZUDCZAMSA-N (2s)-2-[(4-bromophenyl)carbamoylamino]-n-(2,3-dihydroxypropyl)-4-methylpentanamide Chemical compound OCC(O)CNC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(Br)C=C1 MEHDWYDBOQKHNL-KZUDCZAMSA-N 0.000 claims 1
- DMTOJWVPPCFMFC-INIZCTEOSA-N (2s)-2-[(4-bromophenyl)carbamoylamino]-n-(2-hydroxyethyl)-3-phenylpropanamide Chemical compound C([C@@H](C(=O)NCCO)NC(=O)NC=1C=CC(Br)=CC=1)C1=CC=CC=C1 DMTOJWVPPCFMFC-INIZCTEOSA-N 0.000 claims 1
- HIASXAKDYOCRPQ-ZDUSSCGKSA-N (2s)-2-[(4-bromophenyl)carbamoylamino]-n-(2-hydroxyethyl)-4-methylpentanamide Chemical compound OCCNC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(Br)C=C1 HIASXAKDYOCRPQ-ZDUSSCGKSA-N 0.000 claims 1
- DSBITWRMTGDNTD-RISCZKNCSA-N (2s)-2-[(4-bromophenyl)carbamoylamino]-n-[(2r)-1-hydroxypropan-2-yl]-4-methylpentanamide Chemical compound OC[C@@H](C)NC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(Br)C=C1 DSBITWRMTGDNTD-RISCZKNCSA-N 0.000 claims 1
- SPSDTWCAZAFLNC-AWEZNQCLSA-N (2s)-2-[(4-bromophenyl)carbamoylamino]-n-[2-(dimethylamino)-2-oxoethyl]-4-methylpentanamide Chemical compound CN(C)C(=O)CNC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(Br)C=C1 SPSDTWCAZAFLNC-AWEZNQCLSA-N 0.000 claims 1
- BEVMVJHUDJGQIZ-ZANVPECISA-N (2s)-2-[[(2s)-2-[(4-bromo-2-fluorophenyl)carbamoylamino]-4-methylpentanoyl]amino]propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(Br)C=C1F BEVMVJHUDJGQIZ-ZANVPECISA-N 0.000 claims 1
- HILAEZFSMOFJEY-ROUUACIJSA-N (2s)-2-[[(2s)-2-[(4-bromophenyl)carbamoylamino]-4-methylpentanoyl]amino]-2-phenylacetic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@H](C(O)=O)C=1C=CC=CC=1)C(=O)NC1=CC=C(Br)C=C1 HILAEZFSMOFJEY-ROUUACIJSA-N 0.000 claims 1
- AMMVIGUFZGQAQO-GJZGRUSLSA-N (2s)-2-[[(2s)-2-[(4-bromophenyl)carbamoylamino]-4-methylpentanoyl]amino]-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(Br)C=C1 AMMVIGUFZGQAQO-GJZGRUSLSA-N 0.000 claims 1
- LZDASXAVFDPLHY-GJZGRUSLSA-N (2s)-2-[[(2s)-2-[(4-bromophenyl)carbamoylamino]-4-methylpentanoyl]amino]pentanoic acid Chemical compound CCC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(Br)C=C1 LZDASXAVFDPLHY-GJZGRUSLSA-N 0.000 claims 1
- VEUKJHBVYFMVSW-GWCFXTLKSA-N (2s)-2-[[(2s)-2-[(4-bromophenyl)carbamoylamino]-4-methylpentanoyl]amino]propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(Br)C=C1 VEUKJHBVYFMVSW-GWCFXTLKSA-N 0.000 claims 1
- JFQFHPOCFBTXQU-LBPRGKRZSA-N (2s)-4-methyl-n-(2h-tetrazol-5-ylmethyl)-2-[[4-(trifluoromethyl)phenyl]carbamoylamino]pentanamide Chemical compound N([C@@H](CC(C)C)C(=O)NCC=1NN=NN=1)C(=O)NC1=CC=C(C(F)(F)F)C=C1 JFQFHPOCFBTXQU-LBPRGKRZSA-N 0.000 claims 1
- SNQFANBVVDVQEX-LBPRGKRZSA-N (2s)-n-(2-amino-2-oxoethyl)-2-[(4-bromo-2-fluorophenyl)carbamoylamino]-4-methylpentanamide Chemical compound NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(Br)C=C1F SNQFANBVVDVQEX-LBPRGKRZSA-N 0.000 claims 1
- JYWZBPJPSWXWPV-NSHDSACASA-N (2s)-n-(2-amino-2-oxoethyl)-2-[(4-bromo-2-fluorophenyl)carbamoylamino]pentanamide Chemical compound NC(=O)CNC(=O)[C@H](CCC)NC(=O)NC1=CC=C(Br)C=C1F JYWZBPJPSWXWPV-NSHDSACASA-N 0.000 claims 1
- OYFVBKKHXOLILR-LBPRGKRZSA-N (2s)-n-(2-amino-2-oxoethyl)-2-[(4-bromophenyl)carbamoylamino]-4-methylpentanamide Chemical compound NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(Br)C=C1 OYFVBKKHXOLILR-LBPRGKRZSA-N 0.000 claims 1
- OAEMFLAPEVPJGH-NSHDSACASA-N (2s)-n-(2-amino-2-oxoethyl)-2-[(4-bromophenyl)carbamoylamino]pentanamide Chemical compound NC(=O)CNC(=O)[C@H](CCC)NC(=O)NC1=CC=C(Br)C=C1 OAEMFLAPEVPJGH-NSHDSACASA-N 0.000 claims 1
- YLBUEARKTSANET-GJZGRUSLSA-N (2s)-n-[(2s)-1-amino-3-methyl-1-oxobutan-2-yl]-2-[(4-bromophenyl)carbamoylamino]-4-methylpentanamide Chemical compound CC(C)[C@@H](C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(Br)C=C1 YLBUEARKTSANET-GJZGRUSLSA-N 0.000 claims 1
- WVLHIJZNLYUXDZ-CPCISQLKSA-N (2s,3s)-2-[(4-bromo-2-fluorophenyl)carbamoylamino]-3-methylpentanoic acid Chemical compound CC[C@H](C)[C@@H](C(O)=O)NC(=O)NC1=CC=C(Br)C=C1F WVLHIJZNLYUXDZ-CPCISQLKSA-N 0.000 claims 1
- QAFHGJAQMYSDFZ-HZMBPMFUSA-N (2s,3s)-2-[(4-bromophenyl)carbamoylamino]-3-methyl-n-(2-oxopropyl)pentanamide Chemical compound CC(=O)CNC(=O)[C@H]([C@@H](C)CC)NC(=O)NC1=CC=C(Br)C=C1 QAFHGJAQMYSDFZ-HZMBPMFUSA-N 0.000 claims 1
- VEYCFNXDYFEYRJ-KWQFWETISA-N (2s,3s)-2-[(4-bromophenyl)carbamoylamino]-3-methylpentanoic acid Chemical compound CC[C@H](C)[C@@H](C(O)=O)NC(=O)NC1=CC=C(Br)C=C1 VEYCFNXDYFEYRJ-KWQFWETISA-N 0.000 claims 1
- OQPOYHLMRHLEPF-SDBXPKJASA-N (2s,3s)-n-(2-amino-2-oxoethyl)-2-[(4-bromo-2-fluorophenyl)carbamoylamino]-3-methylpentanamide Chemical compound NC(=O)CNC(=O)[C@H]([C@@H](C)CC)NC(=O)NC1=CC=C(Br)C=C1F OQPOYHLMRHLEPF-SDBXPKJASA-N 0.000 claims 1
- RPGZGKDZPQRGRV-ZANVPECISA-N (2s,3s)-n-(2-amino-2-oxoethyl)-2-[(4-bromophenyl)carbamoylamino]-3-methylpentanamide Chemical compound NC(=O)CNC(=O)[C@H]([C@@H](C)CC)NC(=O)NC1=CC=C(Br)C=C1 RPGZGKDZPQRGRV-ZANVPECISA-N 0.000 claims 1
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 claims 1
- XEVINRXCIAOXHU-UHFFFAOYSA-N 1-(2-fluorophenyl)-3-[4-methyl-2,5-dioxo-4-(2-phenylethyl)imidazolidin-1-yl]urea Chemical compound N1C(=O)N(NC(=O)NC=2C(=CC=CC=2)F)C(=O)C1(C)CCC1=CC=CC=C1 XEVINRXCIAOXHU-UHFFFAOYSA-N 0.000 claims 1
- IMUUQAIZKAMZSY-UHFFFAOYSA-N 1-(4-bromo-2-fluorophenyl)-3-(4,4-diethyl-2,5-dioxoimidazolidin-1-yl)urea Chemical compound O=C1C(CC)(CC)NC(=O)N1NC(=O)NC1=CC=C(Br)C=C1F IMUUQAIZKAMZSY-UHFFFAOYSA-N 0.000 claims 1
- WIMHNGNXVXEQGZ-UHFFFAOYSA-N 1-(4-bromo-2-fluorophenyl)-3-(4-ethyl-2,5-dioxo-4-propan-2-ylimidazolidin-1-yl)urea Chemical compound O=C1C(CC)(C(C)C)NC(=O)N1NC(=O)NC1=CC=C(Br)C=C1F WIMHNGNXVXEQGZ-UHFFFAOYSA-N 0.000 claims 1
- MMKCRMGUBFIZFI-UHFFFAOYSA-N 1-(4-bromo-2-fluorophenyl)-3-[4-[2-(2-hydroxyphenyl)ethyl]-4-methyl-2,5-dioxoimidazolidin-1-yl]urea Chemical compound N1C(=O)N(NC(=O)NC=2C(=CC(Br)=CC=2)F)C(=O)C1(C)CCC1=CC=CC=C1O MMKCRMGUBFIZFI-UHFFFAOYSA-N 0.000 claims 1
- RTSHUPJIMHKRNG-UHFFFAOYSA-N 1-(4-bromo-2-fluorophenyl)-3-[4-[2-(3-fluoro-4-hydroxyphenyl)ethyl]-4-methyl-2,5-dioxoimidazolidin-1-yl]urea Chemical compound N1C(=O)N(NC(=O)NC=2C(=CC(Br)=CC=2)F)C(=O)C1(C)CCC1=CC=C(O)C(F)=C1 RTSHUPJIMHKRNG-UHFFFAOYSA-N 0.000 claims 1
- ZQLXEUGZZBJOPW-UHFFFAOYSA-N 1-(4-bromo-2-fluorophenyl)-3-[4-[2-(3-hydroxyphenyl)ethyl]-4-methyl-2,5-dioxoimidazolidin-1-yl]urea Chemical compound N1C(=O)N(NC(=O)NC=2C(=CC(Br)=CC=2)F)C(=O)C1(C)CCC1=CC=CC(O)=C1 ZQLXEUGZZBJOPW-UHFFFAOYSA-N 0.000 claims 1
- CNTTUVKUTSBXPI-UHFFFAOYSA-N 1-(4-bromo-2-fluorophenyl)-3-[4-[2-(4-hydroxyphenyl)ethyl]-4-methyl-2,5-dioxoimidazolidin-1-yl]urea Chemical compound N1C(=O)N(NC(=O)NC=2C(=CC(Br)=CC=2)F)C(=O)C1(C)CCC1=CC=C(O)C=C1 CNTTUVKUTSBXPI-UHFFFAOYSA-N 0.000 claims 1
- VRTVMFISQDKPQM-UHFFFAOYSA-N 1-(4-bromo-2-fluorophenyl)-3-[4-ethyl-2,5-dioxo-4-(2-phenylethyl)imidazolidin-1-yl]urea Chemical compound N1C(=O)N(NC(=O)NC=2C(=CC(Br)=CC=2)F)C(=O)C1(CC)CCC1=CC=CC=C1 VRTVMFISQDKPQM-UHFFFAOYSA-N 0.000 claims 1
- LFAJLUPDADECSJ-UHFFFAOYSA-N 1-(4-bromophenyl)-3-(2,4-dioxo-1,3-diazaspiro[4.5]decan-3-yl)urea Chemical compound C1=CC(Br)=CC=C1NC(=O)NN1C(=O)C2(CCCCC2)NC1=O LFAJLUPDADECSJ-UHFFFAOYSA-N 0.000 claims 1
- BANUQILERIYGRP-UHFFFAOYSA-N 1-(4-bromophenyl)-3-(4,4-dicyclopropyl-2,5-dioxoimidazolidin-1-yl)urea Chemical compound C1=CC(Br)=CC=C1NC(=O)NN1C(=O)C(C2CC2)(C2CC2)NC1=O BANUQILERIYGRP-UHFFFAOYSA-N 0.000 claims 1
- AXJMAFCPYUOIEO-UHFFFAOYSA-N 1-(4-bromophenyl)-3-(4,4-diethyl-2,5-dioxoimidazolidin-1-yl)urea Chemical compound O=C1C(CC)(CC)NC(=O)N1NC(=O)NC1=CC=C(Br)C=C1 AXJMAFCPYUOIEO-UHFFFAOYSA-N 0.000 claims 1
- GMHUILWFSUMZOU-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[2,5-dioxo-4,4-di(propan-2-yl)imidazolidin-1-yl]urea Chemical compound O=C1C(C(C)C)(C(C)C)NC(=O)N1NC(=O)NC1=CC=C(Br)C=C1 GMHUILWFSUMZOU-UHFFFAOYSA-N 0.000 claims 1
- CEZPOASFNJODLF-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[4-(hydroxymethyl)-2,5-dioxo-4-propan-2-ylimidazolidin-1-yl]urea Chemical compound O=C1C(C(C)C)(CO)NC(=O)N1NC(=O)NC1=CC=C(Br)C=C1 CEZPOASFNJODLF-UHFFFAOYSA-N 0.000 claims 1
- JAKMGETWSWBBKI-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[4-[2-(2-fluorophenyl)ethyl]-4-methyl-2,5-dioxoimidazolidin-1-yl]urea Chemical compound N1C(=O)N(NC(=O)NC=2C=CC(Br)=CC=2)C(=O)C1(C)CCC1=CC=CC=C1F JAKMGETWSWBBKI-UHFFFAOYSA-N 0.000 claims 1
- NDJARFOWPZXRND-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[4-[2-(2-hydroxyphenyl)ethyl]-4-methyl-2,5-dioxoimidazolidin-1-yl]urea Chemical compound N1C(=O)N(NC(=O)NC=2C=CC(Br)=CC=2)C(=O)C1(C)CCC1=CC=CC=C1O NDJARFOWPZXRND-UHFFFAOYSA-N 0.000 claims 1
- LAICXIUZNXHCAS-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[4-[2-(3-fluoro-4-hydroxyphenyl)ethyl]-4-methyl-2,5-dioxoimidazolidin-1-yl]urea Chemical compound N1C(=O)N(NC(=O)NC=2C=CC(Br)=CC=2)C(=O)C1(C)CCC1=CC=C(O)C(F)=C1 LAICXIUZNXHCAS-UHFFFAOYSA-N 0.000 claims 1
- WHFAIGNZULEGEE-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[4-[2-(3-fluorophenyl)ethyl]-4-methyl-2,5-dioxoimidazolidin-1-yl]urea Chemical compound N1C(=O)N(NC(=O)NC=2C=CC(Br)=CC=2)C(=O)C1(C)CCC1=CC=CC(F)=C1 WHFAIGNZULEGEE-UHFFFAOYSA-N 0.000 claims 1
- RIJGYMHBXJHWKJ-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[4-[2-(3-hydroxyphenyl)ethyl]-4-methyl-2,5-dioxoimidazolidin-1-yl]urea Chemical compound N1C(=O)N(NC(=O)NC=2C=CC(Br)=CC=2)C(=O)C1(C)CCC1=CC=CC(O)=C1 RIJGYMHBXJHWKJ-UHFFFAOYSA-N 0.000 claims 1
- ULVPSGVKNAVGBA-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[4-[2-(4-fluorophenyl)ethyl]-4-methyl-2,5-dioxoimidazolidin-1-yl]urea Chemical compound N1C(=O)N(NC(=O)NC=2C=CC(Br)=CC=2)C(=O)C1(C)CCC1=CC=C(F)C=C1 ULVPSGVKNAVGBA-UHFFFAOYSA-N 0.000 claims 1
- UNUZQNKTEGFHKS-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[4-[2-(4-hydroxyphenyl)ethyl]-4-methyl-2,5-dioxoimidazolidin-1-yl]urea Chemical compound N1C(=O)N(NC(=O)NC=2C=CC(Br)=CC=2)C(=O)C1(C)CCC1=CC=C(O)C=C1 UNUZQNKTEGFHKS-UHFFFAOYSA-N 0.000 claims 1
- XVAFRERGGZCLSC-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[4-[2-(furan-2-yl)ethyl]-4-methyl-2,5-dioxoimidazolidin-1-yl]urea Chemical compound N1C(=O)N(NC(=O)NC=2C=CC(Br)=CC=2)C(=O)C1(C)CCC1=CC=CO1 XVAFRERGGZCLSC-UHFFFAOYSA-N 0.000 claims 1
- WZUBWDFMPJHXBA-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[4-ethyl-2,5-dioxo-4-(2-phenylethyl)imidazolidin-1-yl]urea Chemical compound N1C(=O)N(NC(=O)NC=2C=CC(Br)=CC=2)C(=O)C1(CC)CCC1=CC=CC=C1 WZUBWDFMPJHXBA-UHFFFAOYSA-N 0.000 claims 1
- CGBOCDQDPMBHIP-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[4-methyl-2,5-dioxo-4-(2-phenylethyl)imidazolidin-1-yl]urea Chemical compound N1C(=O)N(NC(=O)NC=2C=CC(Br)=CC=2)C(=O)C1(C)CCC1=CC=CC=C1 CGBOCDQDPMBHIP-UHFFFAOYSA-N 0.000 claims 1
- OXKOCISLSWJJJB-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[4-methyl-2,5-dioxo-4-(2-thiophen-2-ylethyl)imidazolidin-1-yl]urea Chemical compound N1C(=O)N(NC(=O)NC=2C=CC(Br)=CC=2)C(=O)C1(C)CCC1=CC=CS1 OXKOCISLSWJJJB-UHFFFAOYSA-N 0.000 claims 1
- JWDNVUMPEGUWHM-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[4-methyl-4-[2-(5-methylfuran-2-yl)ethyl]-2,5-dioxoimidazolidin-1-yl]urea Chemical compound O1C(C)=CC=C1CCC1(C)C(=O)N(NC(=O)NC=2C=CC(Br)=CC=2)C(=O)N1 JWDNVUMPEGUWHM-UHFFFAOYSA-N 0.000 claims 1
- ZBXUTNJNUSUWHP-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(2,4-dioxo-1,3-diazaspiro[4.5]decan-3-yl)urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NN1C(=O)C2(CCCCC2)NC1=O ZBXUTNJNUSUWHP-UHFFFAOYSA-N 0.000 claims 1
- ZGKLRHHWQLBTCW-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(4-ethyl-4-methyl-2,5-dioxoimidazolidin-1-yl)urea Chemical compound O=C1C(CC)(C)NC(=O)N1NC(=O)NC1=CC=C(Cl)C=C1 ZGKLRHHWQLBTCW-UHFFFAOYSA-N 0.000 claims 1
- DRLYWWBSFZDWQA-UHFFFAOYSA-N 1-(8-methyl-2,4-dioxo-1,3-diazaspiro[4.5]decan-3-yl)-3-(4-methylphenyl)urea Chemical compound C1CC(C)CCC21C(=O)N(NC(=O)NC=1C=CC(C)=CC=1)C(=O)N2 DRLYWWBSFZDWQA-UHFFFAOYSA-N 0.000 claims 1
- CJHLQOOKWGKLJY-UHFFFAOYSA-N 1-[4-methyl-2,5-dioxo-4-(2-phenylethyl)imidazolidin-1-yl]-3-phenylurea Chemical compound N1C(=O)N(NC(=O)NC=2C=CC=CC=2)C(=O)C1(C)CCC1=CC=CC=C1 CJHLQOOKWGKLJY-UHFFFAOYSA-N 0.000 claims 1
- SBUMMNCNWGVRLJ-UHFFFAOYSA-N 2-(4,4-diethyl-2,5-dioxoimidazolidin-1-yl)-n-(4-fluorophenyl)acetamide Chemical compound O=C1C(CC)(CC)NC(=O)N1CC(=O)NC1=CC=C(F)C=C1 SBUMMNCNWGVRLJ-UHFFFAOYSA-N 0.000 claims 1
- GDTCIMYEJLYEBZ-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)carbamoylamino]-3-phenylpropanoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1NC(=O)NC(C(=O)O)CC1=CC=CC=C1 GDTCIMYEJLYEBZ-UHFFFAOYSA-N 0.000 claims 1
- ISENOEPGABALTE-UHFFFAOYSA-N 2-[(3,4-dimethoxyphenyl)carbamoylamino]-3-phenylpropanoic acid Chemical compound C1=C(OC)C(OC)=CC=C1NC(=O)NC(C(O)=O)CC1=CC=CC=C1 ISENOEPGABALTE-UHFFFAOYSA-N 0.000 claims 1
- IPOHNVXMLANJTR-UHFFFAOYSA-N 2-[(4-bromophenyl)carbamoylamino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C=1NC2=CC=CC=C2C=1CC(C(=O)O)NC(=O)NC1=CC=C(Br)C=C1 IPOHNVXMLANJTR-UHFFFAOYSA-N 0.000 claims 1
- ZNLCEPJDHBSVKN-UHFFFAOYSA-N 2-[(4-chlorophenyl)carbamoylamino]-3-phenylpropanoic acid Chemical compound C=1C=C(Cl)C=CC=1NC(=O)NC(C(=O)O)CC1=CC=CC=C1 ZNLCEPJDHBSVKN-UHFFFAOYSA-N 0.000 claims 1
- ROLQGUCDHGPXCI-UHFFFAOYSA-N 2-[(4-methoxyphenyl)carbamoylamino]-3-phenylpropanoic acid Chemical compound C1=CC(OC)=CC=C1NC(=O)NC(C(O)=O)CC1=CC=CC=C1 ROLQGUCDHGPXCI-UHFFFAOYSA-N 0.000 claims 1
- HHILIFOAVORNLC-UHFFFAOYSA-N 2-[1-[(4-bromo-2-fluorophenyl)carbamoylamino]-2,5-dioxo-4-propan-2-ylimidazolidin-4-yl]-n-(2-hydroxyethyl)acetamide Chemical compound O=C1C(C(C)C)(CC(=O)NCCO)NC(=O)N1NC(=O)NC1=CC=C(Br)C=C1F HHILIFOAVORNLC-UHFFFAOYSA-N 0.000 claims 1
- CLOKOIGWQXYIQV-UHFFFAOYSA-N 2-[1-[(4-bromophenyl)carbamoylamino]-2,5-dioxo-4-propan-2-ylimidazolidin-4-yl]-n-(2-diethoxyphosphorylethyl)acetamide Chemical compound O=C1C(CC(=O)NCCP(=O)(OCC)OCC)(C(C)C)NC(=O)N1NC(=O)NC1=CC=C(Br)C=C1 CLOKOIGWQXYIQV-UHFFFAOYSA-N 0.000 claims 1
- WDEOQUSGGWZNGR-UHFFFAOYSA-N 2-[1-[(4-bromophenyl)carbamoylamino]-2,5-dioxo-4-propan-2-ylimidazolidin-4-yl]-n-(2-hydroxyethyl)acetamide Chemical compound O=C1C(C(C)C)(CC(=O)NCCO)NC(=O)N1NC(=O)NC1=CC=C(Br)C=C1 WDEOQUSGGWZNGR-UHFFFAOYSA-N 0.000 claims 1
- MUMNJJSIAKMOIQ-UHFFFAOYSA-N 2-[2-[1-[(4-bromo-2-fluorophenyl)carbamoylamino]-4-ethyl-2,5-dioxoimidazolidin-4-yl]ethyl]benzoic acid Chemical compound N1C(=O)N(NC(=O)NC=2C(=CC(Br)=CC=2)F)C(=O)C1(CC)CCC1=CC=CC=C1C(O)=O MUMNJJSIAKMOIQ-UHFFFAOYSA-N 0.000 claims 1
- LONIAWYGZGQBSJ-UHFFFAOYSA-N 2-[2-[1-[(4-bromophenyl)carbamoylamino]-2,5-dioxo-4-propan-2-ylimidazolidin-4-yl]ethyl]benzoic acid Chemical compound N1C(=O)N(NC(=O)NC=2C=CC(Br)=CC=2)C(=O)C1(C(C)C)CCC1=CC=CC=C1C(O)=O LONIAWYGZGQBSJ-UHFFFAOYSA-N 0.000 claims 1
- SEDWRZCVHBRJMW-UHFFFAOYSA-N 2-[2-[1-[(4-bromophenyl)carbamoylamino]-4-ethyl-2,5-dioxoimidazolidin-4-yl]ethyl]benzoic acid Chemical compound N1C(=O)N(NC(=O)NC=2C=CC(Br)=CC=2)C(=O)C1(CC)CCC1=CC=CC=C1C(O)=O SEDWRZCVHBRJMW-UHFFFAOYSA-N 0.000 claims 1
- GWOULRCUFTYSHG-LBPRGKRZSA-N 2-[[(2s)-2-[(4-bromo-2-fluorophenyl)carbamoylamino]-4-methylpentanoyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(Br)C=C1F GWOULRCUFTYSHG-LBPRGKRZSA-N 0.000 claims 1
- QYDQTIDVJOKRJM-NSHDSACASA-N 2-[[(2s)-2-[(4-bromo-2-fluorophenyl)carbamoylamino]pentanoyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)[C@H](CCC)NC(=O)NC1=CC=C(Br)C=C1F QYDQTIDVJOKRJM-NSHDSACASA-N 0.000 claims 1
- VKACGCIFXOGMSV-HNNXBMFYSA-N 2-[[(2s)-2-[(4-bromophenyl)carbamoylamino]-3-phenylpropanoyl]amino]acetic acid Chemical compound C([C@@H](C(=O)NCC(=O)O)NC(=O)NC=1C=CC(Br)=CC=1)C1=CC=CC=C1 VKACGCIFXOGMSV-HNNXBMFYSA-N 0.000 claims 1
- WUZBUPYJADEKRK-ZDUSSCGKSA-N 2-[[(2s)-2-[(4-bromophenyl)carbamoylamino]-4-methylpentanoyl]amino]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)NC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(Br)C=C1 WUZBUPYJADEKRK-ZDUSSCGKSA-N 0.000 claims 1
- LASJSIMHDHTROE-LBPRGKRZSA-N 2-[[(2s)-2-[(4-bromophenyl)carbamoylamino]-4-methylpentanoyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(Br)C=C1 LASJSIMHDHTROE-LBPRGKRZSA-N 0.000 claims 1
- APOCNKWKDAQCPO-NSHDSACASA-N 2-[[(2s)-2-[(4-bromophenyl)carbamoylamino]-4-methylsulfanylbutanoyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)[C@H](CCSC)NC(=O)NC1=CC=C(Br)C=C1 APOCNKWKDAQCPO-NSHDSACASA-N 0.000 claims 1
- ARRWDYXSLZNBRO-NSHDSACASA-N 2-[[(2s)-2-[(4-bromophenyl)carbamoylamino]pentanoyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)[C@H](CCC)NC(=O)NC1=CC=C(Br)C=C1 ARRWDYXSLZNBRO-NSHDSACASA-N 0.000 claims 1
- NOUPHQZUCIKPRJ-ZDUSSCGKSA-N 2-[[(2s)-4-methyl-2-[(4-methylsulfanylphenyl)carbamoylamino]pentanoyl]amino]acetic acid Chemical compound CSC1=CC=C(NC(=O)N[C@@H](CC(C)C)C(=O)NCC(O)=O)C=C1 NOUPHQZUCIKPRJ-ZDUSSCGKSA-N 0.000 claims 1
- WGOPETHLVCCHMW-LBPRGKRZSA-N 2-[[(2s)-4-methyl-2-[[4-(trifluoromethyl)phenyl]carbamoylamino]pentanoyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(C(F)(F)F)C=C1 WGOPETHLVCCHMW-LBPRGKRZSA-N 0.000 claims 1
- QTXGBSUJMGBGRI-SDBXPKJASA-N 2-[[(2s,3s)-2-[(4-bromo-2-fluorophenyl)carbamoylamino]-3-methylpentanoyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)[C@H]([C@@H](C)CC)NC(=O)NC1=CC=C(Br)C=C1F QTXGBSUJMGBGRI-SDBXPKJASA-N 0.000 claims 1
- WKPPVFWLQCDKQE-ZANVPECISA-N 2-[[(2s,3s)-2-[(4-bromophenyl)carbamoylamino]-3-methylpentanoyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)[C@H]([C@@H](C)CC)NC(=O)NC1=CC=C(Br)C=C1 WKPPVFWLQCDKQE-ZANVPECISA-N 0.000 claims 1
- ABRLDZBSIGBGNO-UHFFFAOYSA-N 2-[[2-[(4-bromophenyl)carbamoylamino]-2,4-dimethylpentanoyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)C(C)(CC(C)C)NC(=O)NC1=CC=C(Br)C=C1 ABRLDZBSIGBGNO-UHFFFAOYSA-N 0.000 claims 1
- DABXKTZCTUPXLJ-UHFFFAOYSA-N 2-[[2-[(4-bromophenyl)carbamoylamino]-2-ethylbutanoyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)C(CC)(CC)NC(=O)NC1=CC=C(Br)C=C1 DABXKTZCTUPXLJ-UHFFFAOYSA-N 0.000 claims 1
- MXJJTHDBFXAKDT-UHFFFAOYSA-N 2-[[2-[(4-bromophenyl)carbamoylamino]-3-(1h-indol-3-yl)propanoyl]amino]acetic acid Chemical compound C=1NC2=CC=CC=C2C=1CC(C(=O)NCC(=O)O)NC(=O)NC1=CC=C(Br)C=C1 MXJJTHDBFXAKDT-UHFFFAOYSA-N 0.000 claims 1
- DCLHXYQPZHIEBY-ZDUSSCGKSA-N 2-methyl-2-[[(2s)-4-methyl-2-[[4-(trifluoromethyl)phenyl]carbamoylamino]pentanoyl]amino]propanoic acid Chemical compound OC(=O)C(C)(C)NC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(C(F)(F)F)C=C1 DCLHXYQPZHIEBY-ZDUSSCGKSA-N 0.000 claims 1
- SZWNUFZCGVXWAA-INIZCTEOSA-N 3-[[(2s)-2-[(4-bromophenyl)carbamoylamino]-3-phenylpropanoyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)NCCC(=O)O)NC(=O)NC=1C=CC(Br)=CC=1)C1=CC=CC=C1 SZWNUFZCGVXWAA-INIZCTEOSA-N 0.000 claims 1
- ZGVMLLVJMVVXBC-UHFFFAOYSA-N 3-[[2-[1-[(4-bromo-2-fluorophenyl)carbamoylamino]-2,5-dioxo-4-propan-2-ylimidazolidin-4-yl]acetyl]amino]propanoic acid Chemical compound O=C1C(C(C)C)(CC(=O)NCCC(O)=O)NC(=O)N1NC(=O)NC1=CC=C(Br)C=C1F ZGVMLLVJMVVXBC-UHFFFAOYSA-N 0.000 claims 1
- WPFDTZMZCVLQNC-UHFFFAOYSA-N 3-[[2-[1-[(4-bromophenyl)carbamoylamino]-2,5-dioxo-4-propan-2-ylimidazolidin-4-yl]acetyl]amino]propanoic acid Chemical compound O=C1C(C(C)C)(CC(=O)NCCC(O)=O)NC(=O)N1NC(=O)NC1=CC=C(Br)C=C1 WPFDTZMZCVLQNC-UHFFFAOYSA-N 0.000 claims 1
- WOEXOKHOZTZPNP-UHFFFAOYSA-N 3-phenyl-2-(pyridin-3-ylcarbamoylamino)propanoic acid Chemical compound C=1C=CN=CC=1NC(=O)NC(C(=O)O)CC1=CC=CC=C1 WOEXOKHOZTZPNP-UHFFFAOYSA-N 0.000 claims 1
- GAADLCAGWAYSGH-UHFFFAOYSA-N 3-phenyl-2-[[4-(trifluoromethoxy)phenyl]carbamoylamino]propanoic acid Chemical compound C=1C=C(OC(F)(F)F)C=CC=1NC(=O)NC(C(=O)O)CC1=CC=CC=C1 GAADLCAGWAYSGH-UHFFFAOYSA-N 0.000 claims 1
- SLIMOPZXCUSPOX-UHFFFAOYSA-N 3-phenyl-2-[[4-(trifluoromethyl)phenyl]carbamoylamino]propanoic acid Chemical compound C=1C=C(C(F)(F)F)C=CC=1NC(=O)NC(C(=O)O)CC1=CC=CC=C1 SLIMOPZXCUSPOX-UHFFFAOYSA-N 0.000 claims 1
- 208000002874 Acne Vulgaris Diseases 0.000 claims 1
- 201000004384 Alopecia Diseases 0.000 claims 1
- 206010004146 Basal cell carcinoma Diseases 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
- 206010008570 Chloasma Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000002260 Keloid Diseases 0.000 claims 1
- 206010023330 Keloid scar Diseases 0.000 claims 1
- 208000003351 Melanosis Diseases 0.000 claims 1
- 206010051246 Photodermatosis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 241001303601 Rosacea Species 0.000 claims 1
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 claims 1
- 206010072170 Skin wound Diseases 0.000 claims 1
- LENLZYPMKWPZDQ-UHFFFAOYSA-O [4-[(1-carboxy-2-phenylethyl)carbamoylamino]phenyl]-oxoazanium Chemical compound C1=CC=CC(=C1)CC(C(=O)O)NC(=O)NC1=CC=C([NH+]=O)C=C1 LENLZYPMKWPZDQ-UHFFFAOYSA-O 0.000 claims 1
- 235000011054 acetic acid Nutrition 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 claims 1
- 206010000496 acne Diseases 0.000 claims 1
- 208000009621 actinic keratosis Diseases 0.000 claims 1
- 231100000360 alopecia Toxicity 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 210000000981 epithelium Anatomy 0.000 claims 1
- ALQCCNUYRKDOMQ-UHFFFAOYSA-N ethyl 3-[(4-bromophenyl)carbamoylamino]-2,4-dioxo-1,3-diazaspiro[4.5]decane-8-carboxylate Chemical compound C1CC(C(=O)OCC)CCC21C(=O)N(NC(=O)NC=1C=CC(Br)=CC=1)C(=O)N2 ALQCCNUYRKDOMQ-UHFFFAOYSA-N 0.000 claims 1
- 230000001969 hypertrophic effect Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 210000001117 keloid Anatomy 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- YXELRUXLSGTZEG-UHFFFAOYSA-N methyl 2-[2-[1-[(4-bromophenyl)carbamoylamino]-4-ethyl-2,5-dioxoimidazolidin-4-yl]ethyl]benzoate Chemical compound N1C(=O)N(NC(=O)NC=2C=CC(Br)=CC=2)C(=O)C1(CC)CCC1=CC=CC=C1C(=O)OC YXELRUXLSGTZEG-UHFFFAOYSA-N 0.000 claims 1
- SKHUYSZEXQZFCZ-LBPRGKRZSA-N methyl 2-[[(2s)-2-[(4-bromophenyl)carbamoylamino]pentanoyl]amino]acetate Chemical compound COC(=O)CNC(=O)[C@H](CCC)NC(=O)NC1=CC=C(Br)C=C1 SKHUYSZEXQZFCZ-LBPRGKRZSA-N 0.000 claims 1
- BSDVLPAKRFBAAT-UHFFFAOYSA-N n-(4-bromophenyl)-2-(1,3-dioxo-3a,4,7,7a-tetrahydroisoindol-2-yl)acetamide Chemical compound C1=CC(Br)=CC=C1NC(=O)CN1C(=O)C2CC=CCC2C1=O BSDVLPAKRFBAAT-UHFFFAOYSA-N 0.000 claims 1
- UUIRITXPYAOMCC-UHFFFAOYSA-N n-(4-bromophenyl)-2-(2,4-dioxo-1,3-diazaspiro[4.5]decan-3-yl)acetamide Chemical compound C1=CC(Br)=CC=C1NC(=O)CN1C(=O)C2(CCCCC2)NC1=O UUIRITXPYAOMCC-UHFFFAOYSA-N 0.000 claims 1
- CJPRDIDULAXJBO-UHFFFAOYSA-N n-(4-bromophenyl)-2-(2,5-dioxo-4,4-dipropylimidazolidin-1-yl)acetamide Chemical compound O=C1C(CCC)(CCC)NC(=O)N1CC(=O)NC1=CC=C(Br)C=C1 CJPRDIDULAXJBO-UHFFFAOYSA-N 0.000 claims 1
- SIZAXIVFKSSJKA-UHFFFAOYSA-N n-(4-bromophenyl)-2-(4,4-diethyl-2,5-dioxoimidazolidin-1-yl)acetamide Chemical compound O=C1C(CC)(CC)NC(=O)N1CC(=O)NC1=CC=C(Br)C=C1 SIZAXIVFKSSJKA-UHFFFAOYSA-N 0.000 claims 1
- DEQTXYOBBWGLMS-UHFFFAOYSA-N n-(4-bromophenyl)-2-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)acetamide Chemical compound O=C1C(C)(C)NC(=O)N1CC(=O)NC1=CC=C(Br)C=C1 DEQTXYOBBWGLMS-UHFFFAOYSA-N 0.000 claims 1
- VFHJIKCFNPPHJA-UHFFFAOYSA-N n-(4-bromophenyl)-2-(4-cyclopropyl-4-methyl-2,5-dioxoimidazolidin-1-yl)acetamide Chemical compound O=C1C(C)(C2CC2)NC(=O)N1CC(=O)NC1=CC=C(Br)C=C1 VFHJIKCFNPPHJA-UHFFFAOYSA-N 0.000 claims 1
- KHDSTUZMHJIGKK-UHFFFAOYSA-N n-(4-bromophenyl)-2-(4-ethyl-2,5-dioxo-4-phenylimidazolidin-1-yl)acetamide Chemical compound O=C1C(CC)(C=2C=CC=CC=2)NC(=O)N1CC(=O)NC1=CC=C(Br)C=C1 KHDSTUZMHJIGKK-UHFFFAOYSA-N 0.000 claims 1
- LTSWISVZDXQGQX-UHFFFAOYSA-N n-(4-bromophenyl)-2-(4-ethyl-4-methyl-2,5-dioxoimidazolidin-1-yl)acetamide Chemical compound O=C1C(CC)(C)NC(=O)N1CC(=O)NC1=CC=C(Br)C=C1 LTSWISVZDXQGQX-UHFFFAOYSA-N 0.000 claims 1
- OUBSCADNRKXOMJ-UHFFFAOYSA-N n-(4-bromophenyl)-2-[4-methyl-2,5-dioxo-4-(2-phenylethyl)imidazolidin-1-yl]acetamide Chemical compound N1C(=O)N(CC(=O)NC=2C=CC(Br)=CC=2)C(=O)C1(C)CCC1=CC=CC=C1 OUBSCADNRKXOMJ-UHFFFAOYSA-N 0.000 claims 1
- QJCHCMGTTSZGEE-UHFFFAOYSA-N n-(4-chlorophenyl)-2-(4,4-diethyl-2,5-dioxoimidazolidin-1-yl)acetamide Chemical compound O=C1C(CC)(CC)NC(=O)N1CC(=O)NC1=CC=C(Cl)C=C1 QJCHCMGTTSZGEE-UHFFFAOYSA-N 0.000 claims 1
- 230000008845 photoaging Effects 0.000 claims 1
- 230000008832 photodamage Effects 0.000 claims 1
- DVNAAJJNFZBNOH-AWEZNQCLSA-N propan-2-yl 2-[[(2s)-2-[(4-bromophenyl)carbamoylamino]pentanoyl]amino]acetate Chemical compound CC(C)OC(=O)CNC(=O)[C@H](CCC)NC(=O)NC1=CC=C(Br)C=C1 DVNAAJJNFZBNOH-AWEZNQCLSA-N 0.000 claims 1
- 201000004700 rosacea Diseases 0.000 claims 1
- 231100000241 scar Toxicity 0.000 claims 1
- 208000008742 seborrheic dermatitis Diseases 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 201000010153 skin papilloma Diseases 0.000 claims 1
- QVSRSKPJAWLALL-UHFFFAOYSA-N stk257733 Chemical compound C1=CC(Br)=CC=C1NC(=O)CN1C(=O)C2C(C=C3)CC3C2C1=O QVSRSKPJAWLALL-UHFFFAOYSA-N 0.000 claims 1
- PQECWSRQAOCYDI-ROUUACIJSA-N tert-butyl (2s)-2-[[(2s)-2-[(4-bromophenyl)carbamoylamino]-4-methylpentanoyl]amino]pentanoate Chemical compound CC(C)(C)OC(=O)[C@H](CCC)NC(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(Br)C=C1 PQECWSRQAOCYDI-ROUUACIJSA-N 0.000 claims 1
- PDQSMERWJDWTOG-INIZCTEOSA-N tert-butyl 2-[[(2s)-2-[(4-bromophenyl)carbamoylamino]-4-methylpentanoyl]-methylamino]acetate Chemical compound CC(C)(C)OC(=O)CN(C)C(=O)[C@H](CC(C)C)NC(=O)NC1=CC=C(Br)C=C1 PDQSMERWJDWTOG-INIZCTEOSA-N 0.000 claims 1
- 230000029663 wound healing Effects 0.000 claims 1
- -1 —CH 2 -heterocycle Chemical group 0.000 claims 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
- 239000012981 Hank's balanced salt solution Substances 0.000 description 4
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 239000012091 fetal bovine serum Substances 0.000 description 2
- BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- YQYJSBFKSSDGFO-UHFFFAOYSA-N Epihygromycin Natural products OC1C(O)C(C(=O)C)OC1OC(C(=C1)O)=CC=C1C=C(C)C(=O)NC1C(O)C(O)C2OCOC2C1O YQYJSBFKSSDGFO-UHFFFAOYSA-N 0.000 description 1
- 229940125634 FPR2 agonist Drugs 0.000 description 1
- OUVXYXNWSVIOSJ-UHFFFAOYSA-N Fluo-4 Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(OCCOC=2C(=CC=C(C=2)C2=C3C=C(F)C(=O)C=C3OC3=CC(O)=C(F)C=C32)N(CC(O)=O)CC(O)=O)=C1 OUVXYXNWSVIOSJ-UHFFFAOYSA-N 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 101000818546 Homo sapiens N-formyl peptide receptor 2 Proteins 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 102000057492 human FPR2 Human genes 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361773778P | 2013-03-06 | 2013-03-06 | |
| US61/773,778 | 2013-03-06 | ||
| PCT/US2014/020273 WO2014138046A1 (en) | 2013-03-06 | 2014-03-04 | Use of agonists of formyl peptide receptor 2 for treating dermatological diseases |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017157336A Division JP6496787B2 (ja) | 2013-03-06 | 2017-08-17 | 皮膚疾患を治療するためのホルミルペプチド受容体２アゴニストの使用 |
| JP2017157337A Division JP6496788B2 (ja) | 2013-03-06 | 2017-08-17 | 皮膚疾患を治療するためのホルミルペプチド受容体２アゴニストの使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016512194A JP2016512194A (ja) | 2016-04-25 |
| JP2016512194A5 true JP2016512194A5 (enExample) | 2017-04-13 |
| JP6196328B2 JP6196328B2 (ja) | 2017-09-13 |
Family
ID=50389505
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015561540A Expired - Fee Related JP6196328B2 (ja) | 2013-03-06 | 2014-03-04 | 皮膚疾患を治療するためのホルミルペプチド受容体２アゴニストの使用 |
| JP2017157337A Expired - Fee Related JP6496788B2 (ja) | 2013-03-06 | 2017-08-17 | 皮膚疾患を治療するためのホルミルペプチド受容体２アゴニストの使用 |
| JP2017157336A Expired - Fee Related JP6496787B2 (ja) | 2013-03-06 | 2017-08-17 | 皮膚疾患を治療するためのホルミルペプチド受容体２アゴニストの使用 |
| JP2019043933A Expired - Fee Related JP6672499B2 (ja) | 2013-03-06 | 2019-03-11 | 皮膚疾患を治療するためのホルミルペプチド受容体２アゴニストの使用 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017157337A Expired - Fee Related JP6496788B2 (ja) | 2013-03-06 | 2017-08-17 | 皮膚疾患を治療するためのホルミルペプチド受容体２アゴニストの使用 |
| JP2017157336A Expired - Fee Related JP6496787B2 (ja) | 2013-03-06 | 2017-08-17 | 皮膚疾患を治療するためのホルミルペプチド受容体２アゴニストの使用 |
| JP2019043933A Expired - Fee Related JP6672499B2 (ja) | 2013-03-06 | 2019-03-11 | 皮膚疾患を治療するためのホルミルペプチド受容体２アゴニストの使用 |
Country Status (13)
| Country | Link |
|---|---|
| US (5) | US20140256685A1 (enExample) |
| EP (1) | EP2964214A1 (enExample) |
| JP (4) | JP6196328B2 (enExample) |
| KR (2) | KR20210024691A (enExample) |
| CN (2) | CN107714683A (enExample) |
| AR (1) | AR095035A1 (enExample) |
| AU (3) | AU2014226001B2 (enExample) |
| BR (2) | BR112015021392B1 (enExample) |
| CA (3) | CA3114347A1 (enExample) |
| HK (2) | HK1219661A1 (enExample) |
| RU (1) | RU2696487C2 (enExample) |
| TW (1) | TW201446241A (enExample) |
| WO (1) | WO2014138046A1 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106518742B (zh) | 2011-10-26 | 2020-01-21 | 阿勒根公司 | 作为甲酰肽受体样-1(fprl-1)受体调节剂的n-脲取代的氨基酸的酰胺衍生物 |
| JP2015520130A (ja) * | 2012-04-16 | 2015-07-16 | アラーガン、インコーポレイテッドＡｌｌｅｒｇａｎ，Ｉｎｃｏｒｐｏｒａｔｅｄ | ホルミルペプチド受容体２調節物質としての（２−ウレイドアセトアミド）アルキル誘導体 |
| MA37618B1 (fr) | 2012-05-16 | 2017-08-31 | Actelion Pharmaceuticals Ltd | Dérivés pontés fluorés de spiro[2.4]heptane en tant qu'agonistes de récepteur alx |
| US9284288B2 (en) | 2012-05-16 | 2016-03-15 | Actelion Pharmaceuticals Ltd. | 1-(p-tolyl) cyclopropyl substituted bridged spiro[2.4]heptane derivatives as ALX receptor agonists |
| CN103665043B (zh) | 2012-08-30 | 2017-11-10 | 江苏豪森药业集团有限公司 | 一种替诺福韦前药及其在医药上的应用 |
| BR112015021392B1 (pt) * | 2013-03-06 | 2021-11-16 | Allergan, Inc | Uso de agonistas do receptor de peptídeo formil 2 para tratar doenças dermatológicas |
| AR096686A1 (es) | 2013-06-25 | 2016-01-27 | Actelion Pharmaceuticals Ltd | Derivados de espiro[2.4]heptano puenteados sustituidos con difluoroetil-oxazol como agonistas del receptor de alx |
| JP6653253B2 (ja) * | 2013-07-16 | 2020-02-26 | アラーガン、インコーポレイテッドＡｌｌｅｒｇａｎ，Ｉｎｃｏｒｐｏｒａｔｅｄ | ホルミルペプチド受容体モジュレーターとしてのｎ−尿素置換アミノ酸の誘導体 |
| WO2015007830A1 (en) | 2013-07-18 | 2015-01-22 | Actelion Pharmaceuticals Ltd | Piperazine substituted bridged spiro[2.4]heptane derivatives as alx receptor agonists |
| AR097279A1 (es) | 2013-08-09 | 2016-03-02 | Actelion Pharmaceuticals Ltd | Derivados de benzimidazolil-metil urea como agonistas del receptor de alx |
| US9920013B2 (en) | 2014-01-29 | 2018-03-20 | Allergan, Inc. | 2,5-dioxoimidazolidin-1-yl-3-urea derivatives as formyl peptide modulators |
| US9663457B2 (en) | 2014-04-09 | 2017-05-30 | Allergan, Inc. | Carbamoyl hydrazine derivatives as formyl peptide modulators |
| AU2015264021B2 (en) | 2014-05-21 | 2020-02-27 | Allergan, Inc. | Imidazole derivatives as formyl peptide receptor modulators |
| US10717708B2 (en) * | 2015-12-10 | 2020-07-21 | Bristol-Myers Squibb Company | Piperidinone formyl peptide 2 receptor and formyl peptide 1 receptor agonists |
| EP3436431A1 (en) | 2016-03-28 | 2019-02-06 | Allergan, Inc. | Phenyl urea derivatives as n-formyl peptide receptor modulators |
| CA3020316A1 (en) * | 2016-04-12 | 2017-10-19 | Allergan, Inc. | Phenyl urea derivatives as n-formyl peptide receptor modulators |
| TWI746660B (zh) * | 2016-10-06 | 2021-11-21 | 日商第一三共股份有限公司 | 尿素衍生物及其用途 |
| GB2561540A (en) * | 2017-03-13 | 2018-10-24 | Nodthera Ltd | Chemical compounds |
| ES2799098B2 (es) * | 2019-06-10 | 2021-12-10 | Univ Madrid Carlos Iii | Aptameros agonistas del receptor fpr2 y usos de los mismos |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4521210A (en) | 1982-12-27 | 1985-06-04 | Wong Vernon G | Eye implant for relieving glaucoma, and device and method for use therewith |
| JPS63232846A (ja) | 1987-03-20 | 1988-09-28 | Haruo Ogura | 新規な固定相担体 |
| WO2001014328A2 (en) * | 1999-08-20 | 2001-03-01 | Merck & Co., Inc. | Substituted ureas as cell adhesion inhibitors |
| DE10005275A1 (de) * | 2000-02-07 | 2001-08-09 | Bayer Ag | Neuartige Glycokonjugate |
| EP1162194A1 (en) | 2000-06-06 | 2001-12-12 | Aventis Pharma Deutschland GmbH | Factor VIIa inhibitory (thio)urea derivatives, their preparation and their use |
| DE10063008A1 (de) | 2000-12-16 | 2002-06-20 | Merck Patent Gmbh | Carbonsäureamidderivate |
| MXPA05002493A (es) * | 2002-09-05 | 2005-05-27 | Neurosearch As | Derivados de diarilurea y su uso como bloqueadores del canal del cloro. |
| US7576206B2 (en) | 2003-08-14 | 2009-08-18 | Cephalon, Inc. | Proteasome inhibitors and methods of using the same |
| JP4769082B2 (ja) | 2003-12-17 | 2011-09-07 | 武田薬品工業株式会社 | ウレア誘導体、その製造法及び用途 |
| WO2006065755A2 (en) | 2004-12-13 | 2006-06-22 | Glaxo Group Limited | Quaternary ammonium salts of fused hetearomatic amines as novel muscarinic acetylcholine receptor antagonists |
| WO2007076055A2 (en) * | 2005-12-22 | 2007-07-05 | Entremed, Inc. | Compositions and methods comprising proteinase activated receptor antagonists |
| KR20090121832A (ko) * | 2008-05-23 | 2009-11-26 | 인제대학교 산학협력단 | 2-(2-히드록시벤조일)히드라진카르복시아미드 유도체 또는이의 약학적으로 허용가능한 염, 이의 제조방법, 및 이를유효 성분으로 함유하는 선택적 면역 억제용 약학적 조성물 |
| DK2362866T3 (en) * | 2008-11-11 | 2015-10-12 | Signum Biosciences Inc | Isoprenylforbindelser and their methods |
| KR20100101055A (ko) * | 2009-03-07 | 2010-09-16 | 주식회사 메디젠텍 | 세포핵에서 세포질로의 ｇｓｋ３의 이동을 억제하는 화합물을 함유하는 세포핵에서 세포질로의 ｇｓｋ３ 이동 관련 질환의 치료 또는 예방용 약학적 조성물 |
| WO2011073918A2 (en) * | 2009-12-16 | 2011-06-23 | Actelion Pharmaceuticals Ltd | Peptides as modulators of fprl1 and/or fprl2 |
| EP2585054A1 (en) * | 2010-06-24 | 2013-05-01 | Allergan, Inc. | Derivatives of cycloalkyl- and cycloalkenyl-1,2-dicarboxylic acid compounds having formyl peptide receptor like-1 (fprl-1) agonist or antagonist activity |
| AU2011336973A1 (en) * | 2010-12-03 | 2013-07-11 | Allergan, Inc. | Pharmaceutical compositions comprising 3,4- dihydroisoquinolin-2(1 H)-yl-3-phenylurea derivatives having formyl peptide receptor like-1 (FPRL-1) agonist or antagonist activity |
| US8580817B2 (en) | 2011-02-11 | 2013-11-12 | Allergan, Inc. | 1-(1-OXO-1,2,3,4-tetrahydroisoquinolin-7-YL)urea derivatives as N-formyl peptide receptor like-1 (FPRL-1) receptor modulators |
| US8653299B2 (en) | 2011-03-17 | 2014-02-18 | Allergan, Inc. | Dihydronaphthalene and naphthalene derivatives as N-formyl peptide receptor like-1 (FPRL-1) receptor modulators |
| AU2012271562A1 (en) | 2011-06-17 | 2014-01-30 | Allergan, Inc. | D -serine for the treatment of visual system disorders |
| AU2012282977A1 (en) | 2011-07-11 | 2014-02-06 | Allergan, Inc. | Polycyclic pyrrolidine-2,5-dione derivatives as -formyl peptide receptor like-1 (FPRLl-1) receptor modulators |
| CN106518742B (zh) * | 2011-10-26 | 2020-01-21 | 阿勒根公司 | 作为甲酰肽受体样-1(fprl-1)受体调节剂的n-脲取代的氨基酸的酰胺衍生物 |
| US8541577B2 (en) * | 2011-11-10 | 2013-09-24 | Allergan, Inc. | Aryl urea derivatives as N-formyl peptide receptors like-1 (FPRL-1) receptor modulators |
| US8492556B2 (en) * | 2011-11-10 | 2013-07-23 | Allergan, Inc. | 2,5-Dioxoimidazolidin-1-yl-3-phenylurea derivatives as formyl peptide receptor like-1 (FPRL-1) receptor modulators |
| EP2814815A1 (en) | 2012-02-16 | 2014-12-24 | Allergan, Inc. | Imidazolidine-2,4-dione derivatives as n-formyl peptide receptor 2 modulators |
| JP2015520130A (ja) * | 2012-04-16 | 2015-07-16 | アラーガン、インコーポレイテッドＡｌｌｅｒｇａｎ，Ｉｎｃｏｒｐｏｒａｔｅｄ | ホルミルペプチド受容体２調節物質としての（２−ウレイドアセトアミド）アルキル誘導体 |
| BR112015021392B1 (pt) * | 2013-03-06 | 2021-11-16 | Allergan, Inc | Uso de agonistas do receptor de peptídeo formil 2 para tratar doenças dermatológicas |
| BR112015021371B1 (pt) * | 2013-03-06 | 2021-04-13 | Allergan, Inc | Uso de agonistas de receptor de formil peptídeo 2 para tratar doenças inflamatórias oculares |
| JP6653253B2 (ja) * | 2013-07-16 | 2020-02-26 | アラーガン、インコーポレイテッドＡｌｌｅｒｇａｎ，Ｉｎｃｏｒｐｏｒａｔｅｄ | ホルミルペプチド受容体モジュレーターとしてのｎ−尿素置換アミノ酸の誘導体 |
| WO2015042071A1 (en) | 2013-09-19 | 2015-03-26 | Allergan, Inc. | Diphenyl urea derivatives as formyl peptide receptor modulators |
| WO2015077451A1 (en) | 2013-11-21 | 2015-05-28 | Allergan, Inc. | Phenylcarbamate derivatives as formyl peptide receptor modulators |
| AU2015264021B2 (en) * | 2014-05-21 | 2020-02-27 | Allergan, Inc. | Imidazole derivatives as formyl peptide receptor modulators |
-
2014
- 2014-03-04 BR BR112015021392-8A patent/BR112015021392B1/pt not_active IP Right Cessation
- 2014-03-04 KR KR1020217005968A patent/KR20210024691A/ko not_active Ceased
- 2014-03-04 BR BR122017004256A patent/BR122017004256A2/pt not_active Application Discontinuation
- 2014-03-04 CA CA3114347A patent/CA3114347A1/en not_active Abandoned
- 2014-03-04 JP JP2015561540A patent/JP6196328B2/ja not_active Expired - Fee Related
- 2014-03-04 CN CN201711029910.2A patent/CN107714683A/zh active Pending
- 2014-03-04 WO PCT/US2014/020273 patent/WO2014138046A1/en not_active Ceased
- 2014-03-04 HK HK16107753.4A patent/HK1219661A1/zh unknown
- 2014-03-04 CN CN201480011861.8A patent/CN105007908B/zh not_active Expired - Fee Related
- 2014-03-04 AU AU2014226001A patent/AU2014226001B2/en not_active Ceased
- 2014-03-04 RU RU2015134778A patent/RU2696487C2/ru active
- 2014-03-04 CA CA2899804A patent/CA2899804A1/en not_active Abandoned
- 2014-03-04 CA CA3114477A patent/CA3114477A1/en not_active Abandoned
- 2014-03-04 US US14/196,155 patent/US20140256685A1/en not_active Abandoned
- 2014-03-04 KR KR1020157024039A patent/KR102223384B1/ko not_active Expired - Fee Related
- 2014-03-04 EP EP14713302.9A patent/EP2964214A1/en not_active Withdrawn
- 2014-03-06 AR ARP140100733A patent/AR095035A1/es unknown
- 2014-03-06 TW TW103107759A patent/TW201446241A/zh unknown
-
2017
- 2017-04-18 US US15/490,127 patent/US10434112B2/en not_active Expired - Fee Related
- 2017-08-17 JP JP2017157337A patent/JP6496788B2/ja not_active Expired - Fee Related
- 2017-08-17 JP JP2017157336A patent/JP6496787B2/ja not_active Expired - Fee Related
-
2018
- 2018-08-22 HK HK18110777.8A patent/HK1251185A1/zh unknown
-
2019
- 2019-03-06 AU AU2019201538A patent/AU2019201538B2/en not_active Ceased
- 2019-03-11 JP JP2019043933A patent/JP6672499B2/ja not_active Expired - Fee Related
- 2019-09-10 US US16/566,682 patent/US10799518B2/en not_active Expired - Fee Related
-
2020
- 2020-09-22 US US17/028,440 patent/US20210008085A1/en not_active Abandoned
- 2020-09-22 US US17/028,416 patent/US20210000846A1/en not_active Abandoned
-
2021
- 2021-05-18 AU AU2021203183A patent/AU2021203183A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2016512194A5 (enExample) | ||
| RU2015134778A (ru) | Применение агонистов формилпептидного рецептора 2 для лечения дерматологических заболеваний | |
| RU2015136774A (ru) | Применение агонистов формилпептидного рецептора 2 для лечения воспалительных заболеваний глаз | |
| JP2016512193A5 (enExample) | ||
| RU2424233C2 (ru) | Производные бензимидазола, методы их получения, применение их в качестве агонистов фарнезоид-х-рецептора (fxr) и содержащие их фармацевтические препараты | |
| ES2556772T3 (es) | Nicotinamidas sustituidas como moduladores de KCNQ2/3 | |
| RU2011146363A (ru) | Производные n-ацил-n-фенилпиперазина, используемые (кроме того) для профилактики или лечения диабета | |
| JP2010531345A5 (enExample) | ||
| RU2012117885A (ru) | 2,3,5-тризамещенные пирролы, фармацевтическая композиция и лекарственное средство (варианты) на их основе, способ получения соединений (варианты) | |
| JP2013506637A5 (enExample) | ||
| RU2011107227A (ru) | Бензоимидазольные производные и ингибиторы гликоген-синтаза-киназы-3 бета, содержащие такие производные | |
| NZ589504A (en) | Substituted carbinol compound having cyclic linker | |
| HRP20140588T1 (hr) | Spojevi kondenziranog prstena i njihova uporaba | |
| AR047185A1 (es) | Derivados de 4-aril pirimidinas 2-(amino-sustituidas), compuestos relacionados de utilidad para el tratamiento de enfermedades inflamatorias y composiciones farmaceuticas que los contienen como principio activo. | |
| BG65858B1 (bg) | 1,2-диарилбензимидазоли и фармацевтичното им използване | |
| JP2011507883A (ja) | Ｋｖ１．５カリウムチャネル阻害剤としての４−イミダゾリジノン | |
| RU2011136719A (ru) | Фенилимидазольные соединения | |
| HK40045091A (en) | Use of agonists of formyl peptide receptor 2 for treating ocular inflammatory diseases | |
| TH152679A (th) | สารยับยั้งเปปไทด์ดีฟอร์มิเลส | |
| TH93934B (th) | เกลือมาเอลเอต, ทอสิเลต, ฟิวมาเรต, และออกซาเลตของ5-(1(s)-อะมิโน-2-ไฮดรอกซีเอธิล)- -n-[(2,4-ไดฟลูออโร-เฟนิล)-เมธิล]-2-[8-เมธอกซี-2-(ไตรฟลูออโรเมธิล)-5-ควิโนลีน]-4-ออกซาโซลคาร์บอกซามีด และกระบวนการของการเตรียมเพื่อประสงค์อย่างนั้น |