RU2009132108A - Иммунодепрессантные соединения и композиции - Google Patents
Иммунодепрессантные соединения и композиции Download PDFInfo
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- RU2009132108A RU2009132108A RU2009132108/04A RU2009132108A RU2009132108A RU 2009132108 A RU2009132108 A RU 2009132108A RU 2009132108/04 A RU2009132108/04 A RU 2009132108/04A RU 2009132108 A RU2009132108 A RU 2009132108A RU 2009132108 A RU2009132108 A RU 2009132108A
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- Prior art keywords
- ethyl
- propionic acid
- benzylamino
- alkyl
- group
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract 27
- 239000003018 immunosuppressive agent Substances 0.000 title claims 2
- 239000000203 mixture Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 39
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 14
- 125000003118 aryl group Chemical group 0.000 claims abstract 14
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 14
- 239000001257 hydrogen Substances 0.000 claims abstract 14
- 125000005843 halogen group Chemical group 0.000 claims abstract 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract 4
- 125000004429 atom Chemical group 0.000 claims abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 3
- 125000004450 alkenylene group Chemical group 0.000 claims abstract 2
- 125000005842 heteroatom Chemical group 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 20
- -1 1H-tetrazol-5-yl Chemical group 0.000 claims 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 12
- 201000010099 disease Diseases 0.000 claims 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 11
- 230000002757 inflammatory effect Effects 0.000 claims 11
- 208000035475 disorder Diseases 0.000 claims 9
- 235000019260 propionic acid Nutrition 0.000 claims 6
- 206010052779 Transplant rejections Diseases 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 238000011282 treatment Methods 0.000 claims 5
- 230000033115 angiogenesis Effects 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 230000001771 impaired effect Effects 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 201000006417 multiple sclerosis Diseases 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 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 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims 3
- 201000004624 Dermatitis Diseases 0.000 claims 3
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- 208000009525 Myocarditis Diseases 0.000 claims 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 239000003112 inhibitor Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 239000000651 prodrug Substances 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
- PAZFHMRKUCGGMT-UHFFFAOYSA-N 3-[[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=NC=1C(C)=NOCC(C=C1C(F)(F)F)=CC=C1C1CCCCC1 PAZFHMRKUCGGMT-UHFFFAOYSA-N 0.000 claims 2
- 201000004384 Alopecia Diseases 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 208000035473 Communicable disease Diseases 0.000 claims 2
- 206010010356 Congenital anomaly Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 102000036530 EDG receptors Human genes 0.000 claims 2
- 108091007263 EDG receptors Proteins 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 2
- 208000003084 Graves Ophthalmopathy Diseases 0.000 claims 2
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims 2
- 206010022680 Intestinal ischaemia Diseases 0.000 claims 2
- 206010067125 Liver injury Diseases 0.000 claims 2
- 206010029113 Neovascularisation Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 208000001647 Renal Insufficiency Diseases 0.000 claims 2
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 claims 2
- 206010039966 Senile dementia Diseases 0.000 claims 2
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 2
- 208000031709 Skin Manifestations Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000000389 T-cell leukemia Diseases 0.000 claims 2
- 208000028530 T-cell lymphoblastic leukemia/lymphoma Diseases 0.000 claims 2
- 206010042971 T-cell lymphoma Diseases 0.000 claims 2
- 210000001744 T-lymphocyte Anatomy 0.000 claims 2
- 206010044541 Traumatic shock Diseases 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 206010046851 Uveitis Diseases 0.000 claims 2
- 206010047115 Vasculitis Diseases 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 208000007502 anemia Diseases 0.000 claims 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 208000010668 atopic eczema Diseases 0.000 claims 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 230000008859 change Effects 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 230000001434 glomerular Effects 0.000 claims 2
- 208000024908 graft versus host disease Diseases 0.000 claims 2
- 231100000234 hepatic damage Toxicity 0.000 claims 2
- 208000006454 hepatitis Diseases 0.000 claims 2
- 231100000283 hepatitis Toxicity 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 230000002519 immonomodulatory effect Effects 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 208000037906 ischaemic injury Diseases 0.000 claims 2
- 230000000302 ischemic effect Effects 0.000 claims 2
- 201000006370 kidney failure Diseases 0.000 claims 2
- 150000002632 lipids Chemical class 0.000 claims 2
- 230000008818 liver damage Effects 0.000 claims 2
- 231100000516 lung damage Toxicity 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 206010028417 myasthenia gravis Diseases 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 230000007170 pathology Effects 0.000 claims 2
- 102000004169 proteins and genes Human genes 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 208000008742 seborrheic dermatitis Diseases 0.000 claims 2
- 230000035939 shock Effects 0.000 claims 2
- 230000019491 signal transduction Effects 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 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
- ACVUEXXPBUTTGY-UHFFFAOYSA-N 1-[[4-[[1-(4-cyclohexyl-3-ethylphenyl)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=C1CC)=CC=C1C1CCCCC1 ACVUEXXPBUTTGY-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
- JEFPHVLREABUOM-UHFFFAOYSA-N 1-[[4-[c-methyl-n-[[4-phenyl-3-(trifluoromethyl)phenyl]methoxy]carbonimidoyl]phenyl]methyl]pyrrolidine-3-carboxylic acid Chemical compound C=1C=C(CN2CC(CC2)C(O)=O)C=CC=1C(C)=NOCC(C=C1C(F)(F)F)=CC=C1C1=CC=CC=C1 JEFPHVLREABUOM-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
- 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
- HOBHCEUKJKGXOT-UHFFFAOYSA-N 1-[[6-[n-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-c-methylcarbonimidoyl]-2-ethylpyridin-3-yl]methyl]azetidine-3-carboxylic acid Chemical compound CCC1=NC(C(C)=NOCC=2C=C(C(C3CCCCC3)=CC=2)C(F)(F)F)=CC=C1CN1CC(C(O)=O)C1 HOBHCEUKJKGXOT-UHFFFAOYSA-N 0.000 claims 1
- QKJMCQQUCXYMHN-UHFFFAOYSA-N 2-[[4-[c-methyl-n-[(4-phenylphenyl)methoxy]carbonimidoyl]phenyl]methylamino]acetic acid Chemical compound C=1C=C(CNCC(O)=O)C=CC=1C(C)=NOCC(C=C1)=CC=C1C1=CC=CC=C1 QKJMCQQUCXYMHN-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
- QZLPAOIXGOKMPX-UHFFFAOYSA-N 3-[6-[n-[(4-cyclohexyl-3-ethylphenyl)methoxy]-c-methylcarbonimidoyl]-3,4-dihydro-1h-isoquinolin-2-yl]propanoic acid Chemical compound CCC1=CC(CON=C(C)C=2C=C3CCN(CCC(O)=O)CC3=CC=2)=CC=C1C1CCCCC1 QZLPAOIXGOKMPX-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
- HEXYCPNMTPVDCQ-UHFFFAOYSA-N 3-[[2-ethyl-4-[c-methyl-n-[[4-phenyl-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(C=3C=CC=CC=3)=CC=2)C(F)(F)F)=C1 HEXYCPNMTPVDCQ-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
- 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
- QENHSMUMYSRWEL-UHFFFAOYSA-N 3-[[4-[[1-[4-cyclohexyl-3-(trifluoromethyl)phenyl]ethylideneamino]oxymethyl]phenyl]methylamino]propanoic acid Chemical compound C=1C=C(C2CCCCC2)C(C(F)(F)F)=CC=1C(C)=NOCC1=CC=C(CNCCC(O)=O)C=C1 QENHSMUMYSRWEL-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
- DFSXJEXLZGAFLB-UHFFFAOYSA-N 3-[[4-[c-methyl-n-[(4-phenylphenyl)methoxy]carbonimidoyl]phenyl]methylamino]cyclopentane-1-carboxylic acid Chemical compound C=1C=C(CNC2CC(CC2)C(O)=O)C=CC=1C(C)=NOCC(C=C1)=CC=C1C1=CC=CC=C1 DFSXJEXLZGAFLB-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
- ZUWBMGNZVMEQLJ-UHFFFAOYSA-N 3-[[4-[c-methyl-n-[(4-pyridin-3-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=CN=C1 ZUWBMGNZVMEQLJ-UHFFFAOYSA-N 0.000 claims 1
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- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
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| US47193103P | 2003-05-19 | 2003-05-19 | |
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| US56196804P | 2004-04-14 | 2004-04-14 | |
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