JP2007503468A5 - - Google Patents
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- Publication number
- JP2007503468A5 JP2007503468A5 JP2006533199A JP2006533199A JP2007503468A5 JP 2007503468 A5 JP2007503468 A5 JP 2007503468A5 JP 2006533199 A JP2006533199 A JP 2006533199A JP 2006533199 A JP2006533199 A JP 2006533199A JP 2007503468 A5 JP2007503468 A5 JP 2007503468A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- propionic acid
- benzylamino
- trifluoromethyl
- benzyloxyimino
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 35
- -1 1H- tetrazol-5-yl Chemical group 0.000 claims description 15
- 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 claims description 9
- 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 102000036530 EDG receptors Human genes 0.000 claims description 8
- 108091007263 EDG receptors Proteins 0.000 claims description 8
- 229940002612 prodrug Drugs 0.000 claims description 7
- 239000000651 prodrug Substances 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 210000004698 lymphocyte Anatomy 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 43
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- LFRFHNNDPXJMKU-UHFFFAOYSA-N 3-[[2-chloro-4-[n-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-c-methylcarbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C(Cl)=CC=1C(C)=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 LFRFHNNDPXJMKU-UHFFFAOYSA-N 0.000 claims 2
- WKUPACYIFYSYLA-UHFFFAOYSA-N 3-[[4-[n-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-c-methylcarbonimidoyl]-2-ethylphenyl]methylamino]propanoic acid Chemical compound C1=C(CNCCC(O)=O)C(CC)=CC(C(C)=NOCC=2C=C(C(C3CCCCC3)=CC=2)C(F)(F)F)=C1 WKUPACYIFYSYLA-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 230000004075 alteration Effects 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 230000011664 signaling Effects 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- DPOJLQJUAVHWON-UHFFFAOYSA-N 1-[[2-chloro-4-[n-[(4-cyclohexyl-3-ethylphenyl)methoxy]-c-methylcarbonimidoyl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C=1C=C(C2CCCCC2)C(CC)=CC=1CON=C(C)C(C=C1Cl)=CC=C1CN1CC(C(O)=O)C1 DPOJLQJUAVHWON-UHFFFAOYSA-N 0.000 claims 1
- YXYRBRYAOOTOOA-UHFFFAOYSA-N 1-[[4-[[1-[4-cyclohexyl-3-(trifluoromethyl)phenyl]ethylideneamino]oxymethyl]-2-ethylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C=1C=C(CN2CC(C2)C(O)=O)C(CC)=CC=1CON=C(C)C(C=C1C(F)(F)F)=CC=C1C1CCCCC1 YXYRBRYAOOTOOA-UHFFFAOYSA-N 0.000 claims 1
- LHXSPFSQWRNNAH-UHFFFAOYSA-N 1-[[4-[c-methyl-n-[(4-phenylphenyl)methoxy]carbonimidoyl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C=1C=C(CN2CC(C2)C(O)=O)C=CC=1C(C)=NOCC(C=C1)=CC=C1C1=CC=CC=C1 LHXSPFSQWRNNAH-UHFFFAOYSA-N 0.000 claims 1
- AKPNJNPZMMRFFU-UHFFFAOYSA-N 1-[[4-[c-methyl-n-[(4-phenylphenyl)methoxy]carbonimidoyl]phenyl]methyl]piperidine-3-carboxylic acid Chemical compound C=1C=C(CN2CC(CCC2)C(O)=O)C=CC=1C(C)=NOCC(C=C1)=CC=C1C1=CC=CC=C1 AKPNJNPZMMRFFU-UHFFFAOYSA-N 0.000 claims 1
- KYOLVRYITVDLJJ-UHFFFAOYSA-N 1-[[4-[c-methyl-n-[(4-phenylphenyl)methoxy]carbonimidoyl]phenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound C=1C=C(CN2CC(CC2)C(O)=O)C=CC=1C(C)=NOCC(C=C1)=CC=C1C1=CC=CC=C1 KYOLVRYITVDLJJ-UHFFFAOYSA-N 0.000 claims 1
- BXLZLJZXXFKXLR-UHFFFAOYSA-N 1-[[4-[c-methyl-n-[[4-phenyl-3-(trifluoromethyl)phenyl]methoxy]carbonimidoyl]phenyl]methyl]azetidine-3-carboxylic acid Chemical compound C=1C=C(CN2CC(C2)C(O)=O)C=CC=1C(C)=NOCC(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1 BXLZLJZXXFKXLR-UHFFFAOYSA-N 0.000 claims 1
- AOYDOTIZLIPZDW-UHFFFAOYSA-N 1-[[4-[c-methyl-n-[[4-phenyl-3-(trifluoromethyl)phenyl]methoxy]carbonimidoyl]phenyl]methyl]piperidine-3-carboxylic acid Chemical compound C=1C=C(CN2CC(CCC2)C(O)=O)C=CC=1C(C)=NOCC(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1 AOYDOTIZLIPZDW-UHFFFAOYSA-N 0.000 claims 1
- XJMYYQIGVSNZHJ-UHFFFAOYSA-N 1-[[4-[n-[(4-cyclohexyl-3-ethylphenyl)methoxy]-c-methylcarbonimidoyl]-2-ethylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound CCC1=CC(C(C)=NOCC=2C=C(CC)C(C3CCCCC3)=CC=2)=CC=C1CN1CC(C(O)=O)C1 XJMYYQIGVSNZHJ-UHFFFAOYSA-N 0.000 claims 1
- XIQZYBFOFIPUEQ-UHFFFAOYSA-N 1-[[4-[n-[(4-cyclohexyl-3-methylphenyl)methoxy]-c-methylcarbonimidoyl]-2-ethylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound CCC1=CC(C(C)=NOCC=2C=C(C)C(C3CCCCC3)=CC=2)=CC=C1CN1CC(C(O)=O)C1 XIQZYBFOFIPUEQ-UHFFFAOYSA-N 0.000 claims 1
- KVLVNCSAGUJXBX-UHFFFAOYSA-N 1-[[4-[n-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-c-methylcarbonimidoyl]-2-cyclopropylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C=1C=C(CN2CC(C2)C(O)=O)C(C2CC2)=CC=1C(C)=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 KVLVNCSAGUJXBX-UHFFFAOYSA-N 0.000 claims 1
- KIHYPELVXPAIDH-UHFFFAOYSA-N 1-[[4-[n-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-c-methylcarbonimidoyl]-2-ethylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound CCC1=CC(C(C)=NOCC=2C=C(C(C3CCCCC3)=CC=2)C(F)(F)F)=CC=C1CN1CC(C(O)=O)C1 KIHYPELVXPAIDH-UHFFFAOYSA-N 0.000 claims 1
- DCOLWTCXKAPHTJ-UHFFFAOYSA-N 1-[[4-[n-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-c-methylcarbonimidoyl]-2-fluorophenyl]methyl]azetidine-3-carboxylic acid Chemical compound C=1C=C(CN2CC(C2)C(O)=O)C(F)=CC=1C(C)=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 DCOLWTCXKAPHTJ-UHFFFAOYSA-N 0.000 claims 1
- GCWXAXRCSPZYSS-UHFFFAOYSA-N 1-[[4-[n-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-c-methylcarbonimidoyl]-2-methylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound C=1C=C(CN2CC(C2)C(O)=O)C(C)=CC=1C(C)=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 GCWXAXRCSPZYSS-UHFFFAOYSA-N 0.000 claims 1
- WWGKJVRKHMOAQM-UHFFFAOYSA-N 2-fluoro-3-[[4-[c-methyl-n-[[4-phenyl-3-(trifluoromethyl)phenyl]methoxy]carbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCC(F)C(O)=O)C=CC=1C(C)=NOCC(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1 WWGKJVRKHMOAQM-UHFFFAOYSA-N 0.000 claims 1
- NTQYZHHWFGOWNJ-UHFFFAOYSA-N 2-hydroxy-3-[[4-[c-methyl-n-[[4-phenyl-3-(trifluoromethyl)phenyl]methoxy]carbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCC(O)C(O)=O)C=CC=1C(C)=NOCC(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1 NTQYZHHWFGOWNJ-UHFFFAOYSA-N 0.000 claims 1
- IAPIULQBGXQZAM-UHFFFAOYSA-N 3-[6-[n-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-c-methylcarbonimidoyl]-3,4-dihydro-1h-isoquinolin-2-yl]propanoic acid Chemical compound C=1C=C2CN(CCC(O)=O)CCC2=CC=1C(C)=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 IAPIULQBGXQZAM-UHFFFAOYSA-N 0.000 claims 1
- GXDNCXSZIRTCAL-UHFFFAOYSA-N 3-[[2-[n-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-c-methylcarbonimidoyl]pyridin-4-yl]methylamino]propanoic acid Chemical compound C=1C(CNCCC(O)=O)=CC=NC=1C(C)=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 GXDNCXSZIRTCAL-UHFFFAOYSA-N 0.000 claims 1
- MKLBCKJXIOCLSN-UHFFFAOYSA-N 3-[[2-bromo-4-[n-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-c-methylcarbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C(Br)=CC=1C(C)=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 MKLBCKJXIOCLSN-UHFFFAOYSA-N 0.000 claims 1
- HQOOTDPMLLRBCD-UHFFFAOYSA-N 3-[[2-chloro-4-[n-[(4-cyclohexyl-3-ethylphenyl)methoxy]-c-methylcarbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(C2CCCCC2)C(CC)=CC=1CON=C(C)C1=CC=C(CNCCC(O)=O)C(Cl)=C1 HQOOTDPMLLRBCD-UHFFFAOYSA-N 0.000 claims 1
- SDGIPQJVFIMNII-UHFFFAOYSA-N 3-[[2-chloro-6-[n-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-c-methylcarbonimidoyl]pyridin-3-yl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C(Cl)=NC=1C(C)=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 SDGIPQJVFIMNII-UHFFFAOYSA-N 0.000 claims 1
- CSWCSFULCJNOKW-UHFFFAOYSA-N 3-[[2-ethyl-4-[c-methyl-n-[[4-piperidin-1-yl-3-(trifluoromethyl)phenyl]methoxy]carbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C1=C(CNCCC(O)=O)C(CC)=CC(C(C)=NOCC=2C=C(C(N3CCCCC3)=CC=2)C(F)(F)F)=C1 CSWCSFULCJNOKW-UHFFFAOYSA-N 0.000 claims 1
- VGSGLNHGSGLSRK-UHFFFAOYSA-N 3-[[2-methoxy-6-[c-methyl-n-[[4-phenyl-3-(trifluoromethyl)phenyl]methoxy]carbonimidoyl]pyridin-3-yl]methylamino]propanoic acid Chemical compound C1=C(CNCCC(O)=O)C(OC)=NC(C(C)=NOCC=2C=C(C(C=3C=CC=CC=3)=CC=2)C(F)(F)F)=C1 VGSGLNHGSGLSRK-UHFFFAOYSA-N 0.000 claims 1
- GHDLKVYLFMCSEI-UHFFFAOYSA-N 3-[[4-[N-[1-(4-cyclopentylphenyl)-2,2,2-trifluoroethoxy]-C-methylcarbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C1(CCCC1)C1=CC=C(C(ON=C(C)C2=CC=C(CNCCC(=O)O)C=C2)C(F)(F)F)C=C1 GHDLKVYLFMCSEI-UHFFFAOYSA-N 0.000 claims 1
- DPRWSQDYRUMUJG-UHFFFAOYSA-N 3-[[4-[[1-[4-cyclohexyl-3-(trifluoromethyl)phenyl]ethylideneamino]oxymethyl]-2-ethylphenyl]methylamino]propanoic acid Chemical compound C1=C(CNCCC(O)=O)C(CC)=CC(CON=C(C)C=2C=C(C(C3CCCCC3)=CC=2)C(F)(F)F)=C1 DPRWSQDYRUMUJG-UHFFFAOYSA-N 0.000 claims 1
- MGAWCZLYCGCMEK-UHFFFAOYSA-N 3-[[4-[[1-[4-phenyl-3-(trifluoromethyl)phenyl]ethylideneamino]oxymethyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(C=2C=CC=CC=2)C(C(F)(F)F)=CC=1C(C)=NOCC1=CC=C(CNCCC(O)=O)C=C1 MGAWCZLYCGCMEK-UHFFFAOYSA-N 0.000 claims 1
- NSGLALSGUVSATD-UHFFFAOYSA-N 3-[[4-[c-methyl-n-[(3-phenylphenyl)methoxy]carbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C=CC=1C(C)=NOCC(C=1)=CC=CC=1C1=CC=CC=C1 NSGLALSGUVSATD-UHFFFAOYSA-N 0.000 claims 1
- PWPIIHLTBNNXGM-UHFFFAOYSA-N 3-[[4-[c-methyl-n-[(4-phenylphenyl)methoxy]carbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C=CC=1C(C)=NOCC(C=C1)=CC=C1C1=CC=CC=C1 PWPIIHLTBNNXGM-UHFFFAOYSA-N 0.000 claims 1
- JSMXWHMYDAGXQL-UHFFFAOYSA-N 3-[[4-[c-methyl-n-[(4-phenylthiophen-2-yl)methoxy]carbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C=CC=1C(C)=NOCC(SC=1)=CC=1C1=CC=CC=C1 JSMXWHMYDAGXQL-UHFFFAOYSA-N 0.000 claims 1
- DIGDERQXDDJALZ-UHFFFAOYSA-N 3-[[4-[c-methyl-n-[(4-pyridin-4-ylphenyl)methoxy]carbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C=CC=1C(C)=NOCC(C=C1)=CC=C1C1=CC=NC=C1 DIGDERQXDDJALZ-UHFFFAOYSA-N 0.000 claims 1
- YPCMWKNKUFSBTA-UHFFFAOYSA-N 3-[[4-[c-methyl-n-[(5-phenylfuran-2-yl)methoxy]carbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C=CC=1C(C)=NOCC(O1)=CC=C1C1=CC=CC=C1 YPCMWKNKUFSBTA-UHFFFAOYSA-N 0.000 claims 1
- XWNIJNAKDQSWKI-UHFFFAOYSA-N 3-[[4-[c-methyl-n-[(5-phenylthiophen-2-yl)methoxy]carbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C=CC=1C(C)=NOCC(S1)=CC=C1C1=CC=CC=C1 XWNIJNAKDQSWKI-UHFFFAOYSA-N 0.000 claims 1
- PXVNFRLACUSXDF-UHFFFAOYSA-N 3-[[4-[c-methyl-n-[[4-[3-(trifluoromethoxy)phenyl]phenyl]methoxy]carbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C=CC=1C(C)=NOCC(C=C1)=CC=C1C1=CC=CC(OC(F)(F)F)=C1 PXVNFRLACUSXDF-UHFFFAOYSA-N 0.000 claims 1
- BEPPOTGFICHHRU-UHFFFAOYSA-N 3-[[4-[c-methyl-n-[[4-[3-(trifluoromethyl)phenyl]phenyl]methoxy]carbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C=CC=1C(C)=NOCC(C=C1)=CC=C1C1=CC=CC(C(F)(F)F)=C1 BEPPOTGFICHHRU-UHFFFAOYSA-N 0.000 claims 1
- KXDBQQXZJPVUBR-UHFFFAOYSA-N 3-[[4-[c-methyl-n-[[4-phenyl-3-(trifluoromethyl)phenyl]methoxy]carbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C=CC=1C(C)=NOCC(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1 KXDBQQXZJPVUBR-UHFFFAOYSA-N 0.000 claims 1
- WPZOGBHZDWXKSH-UHFFFAOYSA-N 3-[[4-[c-methyl-n-[[4-thiophen-2-yl-3-(trifluoromethyl)phenyl]methoxy]carbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C=CC=1C(C)=NOCC(C=C1C(F)(F)F)=CC=C1C1=CC=CS1 WPZOGBHZDWXKSH-UHFFFAOYSA-N 0.000 claims 1
- MYKVCQCUWLWJJL-UHFFFAOYSA-N 3-[[4-[c-methyl-n-[[4-thiophen-3-yl-2-(trifluoromethyl)phenyl]methoxy]carbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C=CC=1C(C)=NOCC(C(=C1)C(F)(F)F)=CC=C1C=1C=CSC=1 MYKVCQCUWLWJJL-UHFFFAOYSA-N 0.000 claims 1
- BNQIWHKSAPEYBI-UHFFFAOYSA-N 3-[[4-[c-methyl-n-[[4-thiophen-3-yl-3-(trifluoromethyl)phenyl]methoxy]carbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C=CC=1C(C)=NOCC(C=C1C(F)(F)F)=CC=C1C=1C=CSC=1 BNQIWHKSAPEYBI-UHFFFAOYSA-N 0.000 claims 1
- IOGFZDMRKKVGJF-UHFFFAOYSA-N 3-[[4-[n-[(2-fluoro-4-phenylphenyl)methoxy]-c-methylcarbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C=CC=1C(C)=NOCC(C(=C1)F)=CC=C1C1=CC=CC=C1 IOGFZDMRKKVGJF-UHFFFAOYSA-N 0.000 claims 1
- KQGLPLHGCTWGOU-UHFFFAOYSA-N 3-[[4-[n-[(3-chloro-4-cyclohexylphenyl)methoxy]-c-methylcarbonimidoyl]-2-ethylphenyl]methylamino]propanoic acid Chemical compound C1=C(CNCCC(O)=O)C(CC)=CC(C(C)=NOCC=2C=C(Cl)C(C3CCCCC3)=CC=2)=C1 KQGLPLHGCTWGOU-UHFFFAOYSA-N 0.000 claims 1
- MOUNBUWZTSSCCM-UHFFFAOYSA-N 3-[[4-[n-[(3-fluoro-4-phenylphenyl)methoxy]-c-methylcarbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C=CC=1C(C)=NOCC(C=C1F)=CC=C1C1=CC=CC=C1 MOUNBUWZTSSCCM-UHFFFAOYSA-N 0.000 claims 1
- AVVRSZLPEOCJFW-UHFFFAOYSA-N 3-[[4-[n-[(4-cyclohexyl-3-fluorophenyl)methoxy]-c-methylcarbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C=CC=1C(C)=NOCC(C=C1F)=CC=C1C1CCCCC1 AVVRSZLPEOCJFW-UHFFFAOYSA-N 0.000 claims 1
- LEDNNULRIWDNHM-UHFFFAOYSA-N 3-[[4-[n-[(4-cyclohexyl-3-methylphenyl)methoxy]-c-methylcarbonimidoyl]-2-ethylphenyl]methylamino]propanoic acid Chemical compound C1=C(CNCCC(O)=O)C(CC)=CC(C(C)=NOCC=2C=C(C)C(C3CCCCC3)=CC=2)=C1 LEDNNULRIWDNHM-UHFFFAOYSA-N 0.000 claims 1
- VXBXROYQOOEMRL-UHFFFAOYSA-N 3-[[4-[n-[[4-(3,3-dimethylbutyl)-3-(trifluoromethyl)phenyl]methoxy]-c-methylcarbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C=CC=1C(C)=NOCC1=CC=C(CCC(C)(C)C)C(C(F)(F)F)=C1 VXBXROYQOOEMRL-UHFFFAOYSA-N 0.000 claims 1
- VTLKTGLYBKFMGH-UHFFFAOYSA-N 3-[[4-[n-[[4-(3-methoxyphenyl)phenyl]methoxy]-c-methylcarbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound COC1=CC=CC(C=2C=CC(CON=C(C)C=3C=CC(CNCCC(O)=O)=CC=3)=CC=2)=C1 VTLKTGLYBKFMGH-UHFFFAOYSA-N 0.000 claims 1
- WHVIRHWAJRUOKN-UHFFFAOYSA-N 3-[[4-[n-[[4-(4-fluorophenyl)-3-(trifluoromethyl)phenyl]methoxy]-c-methylcarbonimidoyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(CNCCC(O)=O)C=CC=1C(C)=NOCC(C=C1C(F)(F)F)=CC=C1C1=CC=C(F)C=C1 WHVIRHWAJRUOKN-UHFFFAOYSA-N 0.000 claims 1
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- 2004-05-19 EP EP11183758.9A patent/EP2514743B1/en not_active Expired - Lifetime
- 2004-05-19 US US10/849,323 patent/US20050014728A1/en not_active Abandoned
- 2004-05-19 BR BRPI0410741A patent/BRPI0410741B8/pt not_active IP Right Cessation
- 2004-05-19 CL CL200401119A patent/CL2004001119A1/es unknown
- 2004-05-19 EP EP04752597.7A patent/EP1633336B1/en not_active Expired - Lifetime
-
2005
- 2005-10-31 IL IL171683A patent/IL171683A/en not_active IP Right Cessation
- 2005-11-10 EC EC2005006148A patent/ECSP056148A/es unknown
- 2005-11-15 MA MA28608A patent/MA27807A1/fr unknown
- 2005-11-18 TN TNP2005000294A patent/TNSN05294A1/en unknown
- 2005-12-08 NO NO20055837A patent/NO334457B1/no unknown
-
2008
- 2008-02-01 US US12/024,992 patent/US7939519B2/en active Active
- 2008-07-11 AU AU2008203087A patent/AU2008203087A1/en not_active Abandoned
-
2009
- 2009-08-26 RU RU2009132108/04A patent/RU2009132108A/ru not_active Application Discontinuation
-
2010
- 2010-08-20 JP JP2010185021A patent/JP2011012069A/ja active Pending
-
2016
- 2016-09-20 CY CY20161100933T patent/CY1118299T1/el unknown
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