NO322910B1 - 4-Pyridyl-N-acyl-L-fenylalaniner, anvendelse av disse som medikamenter, farmasoytiske preparater inneholdende slike forbindelser og fremgangsmate for fremstilling av disse. - Google Patents
4-Pyridyl-N-acyl-L-fenylalaniner, anvendelse av disse som medikamenter, farmasoytiske preparater inneholdende slike forbindelser og fremgangsmate for fremstilling av disse. Download PDFInfo
- Publication number
- NO322910B1 NO322910B1 NO20022650A NO20022650A NO322910B1 NO 322910 B1 NO322910 B1 NO 322910B1 NO 20022650 A NO20022650 A NO 20022650A NO 20022650 A NO20022650 A NO 20022650A NO 322910 B1 NO322910 B1 NO 322910B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- hydrogen
- oxo
- carbonyl
- pyridinyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 154
- 238000000034 method Methods 0.000 title claims description 33
- 239000003814 drug Substances 0.000 title claims description 10
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 133
- 239000001257 hydrogen Substances 0.000 claims description 132
- -1 Q-C6alkylsulfinyl Chemical group 0.000 claims description 106
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 99
- 150000002431 hydrogen Chemical class 0.000 claims description 76
- 229910052736 halogen Inorganic materials 0.000 claims description 53
- 150000002367 halogens Chemical class 0.000 claims description 53
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 49
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 229960005190 phenylalanine Drugs 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 125000001624 naphthyl group Chemical group 0.000 claims description 26
- 239000000460 chlorine Substances 0.000 claims description 23
- 108010008212 Integrin alpha4beta1 Proteins 0.000 claims description 19
- 108010000134 Vascular Cell Adhesion Molecule-1 Proteins 0.000 claims description 19
- 102100023543 Vascular cell adhesion protein 1 Human genes 0.000 claims description 19
- 230000027455 binding Effects 0.000 claims description 17
- 125000004494 ethyl ester group Chemical group 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- UJSGTHFOHGFQMM-KRWDZBQOSA-N (2s)-2-[(2,6-dichlorobenzoyl)amino]-3-[4-[1,4-dimethyl-2-oxo-6-(trifluoromethyl)pyridin-3-yl]phenyl]propanoic acid Chemical compound C1=C(C(F)(F)F)N(C)C(=O)C(C=2C=CC(C[C@H](NC(=O)C=3C(=CC=CC=3Cl)Cl)C(O)=O)=CC=2)=C1C UJSGTHFOHGFQMM-KRWDZBQOSA-N 0.000 claims description 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 208000006673 asthma Diseases 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- WVTAFEUTNNWYQO-SFHVURJKSA-N (2s)-2-[(2,6-dichlorobenzoyl)amino]-3-[4-(1,4-dimethyl-2-oxopyridin-3-yl)phenyl]propanoic acid Chemical compound C1=CN(C)C(=O)C(C=2C=CC(C[C@H](NC(=O)C=3C(=CC=CC=3Cl)Cl)C(O)=O)=CC=2)=C1C WVTAFEUTNNWYQO-SFHVURJKSA-N 0.000 claims description 8
- SQKRZWKSHPTTCU-IBGZPJMESA-N (2s)-2-[(2-chloro-6-methylbenzoyl)amino]-3-[4-(1,4-dimethyl-2-oxopyridin-3-yl)phenyl]propanoic acid Chemical compound CC1=CC=CC(Cl)=C1C(=O)N[C@H](C(O)=O)CC1=CC=C(C=2C(N(C)C=CC=2C)=O)C=C1 SQKRZWKSHPTTCU-IBGZPJMESA-N 0.000 claims description 8
- APVDSPBBKYMHQH-IBGZPJMESA-N (2s)-2-[(2-chloro-6-methylbenzoyl)amino]-3-[4-[1,6-dimethyl-2-oxo-4-(trifluoromethyl)pyridin-3-yl]phenyl]propanoic acid Chemical compound CC1=CC=CC(Cl)=C1C(=O)N[C@H](C(O)=O)CC1=CC=C(C=2C(N(C)C(C)=CC=2C(F)(F)F)=O)C=C1 APVDSPBBKYMHQH-IBGZPJMESA-N 0.000 claims description 8
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 8
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 8
- IBAZQIKVHCLTHH-SFHVURJKSA-N N-(2,6-dichlorobenzoyl)-4-[1,6-dimethyl-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl]-L-phenylalanine Chemical compound O=C1N(C)C(C)=CC(C(F)(F)F)=C1C(C=C1)=CC=C1C[C@@H](C(O)=O)NC(=O)C1=C(Cl)C=CC=C1Cl IBAZQIKVHCLTHH-SFHVURJKSA-N 0.000 claims description 8
- LFMFPKKYRXFHHZ-UHFFFAOYSA-N R24 Chemical compound C1=C(Cl)C(C)=CC=C1NC1=NC(N)=C(C=CC=C2)C2=N1 LFMFPKKYRXFHHZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 201000006417 multiple sclerosis Diseases 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- CGDRAVDJURFDMP-SFHVURJKSA-N (2s)-2-[(2-chloro-6-methylbenzoyl)amino]-3-[4-[1,4-dimethyl-2-oxo-6-(trifluoromethyl)pyridin-3-yl]phenyl]propanoic acid Chemical compound CC1=CC=CC(Cl)=C1C(=O)N[C@H](C(O)=O)CC1=CC=C(C=2C(N(C)C(=CC=2C)C(F)(F)F)=O)C=C1 CGDRAVDJURFDMP-SFHVURJKSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
- BWJPNBIUIHZRPA-FQEVSTJZSA-N (2s)-2-[(2-bromo-5-methoxybenzoyl)amino]-3-[4-(1-methyl-2-oxopyridin-3-yl)phenyl]propanoic acid Chemical compound COC1=CC=C(Br)C(C(=O)N[C@@H](CC=2C=CC(=CC=2)C=2C(N(C)C=CC=2)=O)C(O)=O)=C1 BWJPNBIUIHZRPA-FQEVSTJZSA-N 0.000 claims description 5
- CBPNUSPLCWQDTD-NRFANRHFSA-N (2s)-3-[4-[1,6-dimethyl-2-oxo-4-(trifluoromethyl)pyridin-3-yl]phenyl]-2-[(2-ethyl-6-methylbenzoyl)amino]propanoic acid Chemical compound CCC1=CC=CC(C)=C1C(=O)N[C@H](C(O)=O)CC1=CC=C(C=2C(N(C)C(C)=CC=2C(F)(F)F)=O)C=C1 CBPNUSPLCWQDTD-NRFANRHFSA-N 0.000 claims description 5
- QWKCHTVWYPJVFD-QFIPXVFZSA-N (2s)-3-[4-[1,6-dimethyl-2-oxo-4-(trifluoromethyl)pyridin-3-yl]phenyl]-2-[(2-methyl-6-propan-2-ylbenzoyl)amino]propanoic acid Chemical compound CC(C)C1=CC=CC(C)=C1C(=O)N[C@H](C(O)=O)CC1=CC=C(C=2C(N(C)C(C)=CC=2C(F)(F)F)=O)C=C1 QWKCHTVWYPJVFD-QFIPXVFZSA-N 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- RFEBDZANCVHDLP-UHFFFAOYSA-N 3-[(4-cyanophenyl)methylamino]-6-(trifluoromethyl)quinoxaline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=C(C(F)(F)F)C=C2N=C1NCC1=CC=C(C#N)C=C1 RFEBDZANCVHDLP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- LCEHGBPILWMVQF-DEOSSOPVSA-N 2-(diethylamino)ethyl (2s)-2-[(2,6-dichlorobenzoyl)amino]-3-[4-[1,6-dimethyl-2-oxo-4-(trifluoromethyl)pyridin-3-yl]phenyl]propanoate Chemical compound C([C@@H](C(=O)OCCN(CC)CC)NC(=O)C=1C(=CC=CC=1Cl)Cl)C(C=C1)=CC=C1C1=C(C(F)(F)F)C=C(C)N(C)C1=O LCEHGBPILWMVQF-DEOSSOPVSA-N 0.000 claims description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
- BZUQBPXFWRLGCI-FQEVSTJZSA-N ethyl (2s)-2-[(2,6-dichlorobenzoyl)amino]-3-[4-[1,6-dimethyl-2-oxo-4-(trifluoromethyl)pyridin-3-yl]phenyl]propanoate Chemical compound C([C@@H](C(=O)OCC)NC(=O)C=1C(=CC=CC=1Cl)Cl)C(C=C1)=CC=C1C1=C(C(F)(F)F)C=C(C)N(C)C1=O BZUQBPXFWRLGCI-FQEVSTJZSA-N 0.000 claims description 3
- PBIAFEAQIMQDNE-FQEVSTJZSA-N (2s)-3-[4-[1,6-dimethyl-2-oxo-4-(trifluoromethyl)pyridin-3-yl]phenyl]-2-[[1-(2-methoxyethyl)cyclopentanecarbonyl]amino]propanoic acid Chemical compound N([C@@H](CC=1C=CC(=CC=1)C=1C(N(C)C(C)=CC=1C(F)(F)F)=O)C(O)=O)C(=O)C1(CCOC)CCCC1 PBIAFEAQIMQDNE-FQEVSTJZSA-N 0.000 claims description 2
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 2
- KAJHDLSDJFIURS-XLDIYJRPSA-N 1-acetyloxyethyl (2s)-2-[(2,6-dichlorobenzoyl)amino]-3-[4-[1,6-dimethyl-2-oxo-4-(trifluoromethyl)pyridin-3-yl]phenyl]propanoate Chemical compound C([C@@H](C(=O)OC(OC(C)=O)C)NC(=O)C=1C(=CC=CC=1Cl)Cl)C(C=C1)=CC=C1C1=C(C(F)(F)F)C=C(C)N(C)C1=O KAJHDLSDJFIURS-XLDIYJRPSA-N 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
- 125000006727 (C1-C6) alkenyl group Chemical class 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 189
- 239000000243 solution Substances 0.000 description 110
- 239000000203 mixture Substances 0.000 description 91
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 57
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 52
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 46
- 239000007787 solid Substances 0.000 description 44
- 238000001704 evaporation Methods 0.000 description 41
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- 239000011734 sodium Substances 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- 239000012267 brine Substances 0.000 description 38
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000000725 suspension Substances 0.000 description 35
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 34
- 238000001914 filtration Methods 0.000 description 34
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 31
- 239000002274 desiccant Substances 0.000 description 30
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 150000002500 ions Chemical class 0.000 description 15
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000000872 buffer Substances 0.000 description 14
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
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- 230000000694 effects Effects 0.000 description 8
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 7
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
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- 210000003979 eosinophil Anatomy 0.000 description 7
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- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 6
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 210000004698 lymphocyte Anatomy 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- 102000016359 Fibronectins Human genes 0.000 description 5
- 108010067306 Fibronectins Proteins 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
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- 239000012312 sodium hydride Substances 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
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- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
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- REDSKZBUUUQMSK-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC.CCCC[Sn](CCCC)CCCC REDSKZBUUUQMSK-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16909099P | 1999-12-06 | 1999-12-06 | |
| PCT/EP2000/011979 WO2001042215A1 (en) | 1999-12-06 | 2000-11-29 | 4-pyridinyl-n-acyl-l-phenylalanines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20022650L NO20022650L (no) | 2002-06-05 |
| NO20022650D0 NO20022650D0 (no) | 2002-06-05 |
| NO322910B1 true NO322910B1 (no) | 2006-12-18 |
Family
ID=22614226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20022650A NO322910B1 (no) | 1999-12-06 | 2002-06-05 | 4-Pyridyl-N-acyl-L-fenylalaniner, anvendelse av disse som medikamenter, farmasoytiske preparater inneholdende slike forbindelser og fremgangsmate for fremstilling av disse. |
Country Status (34)
| Country | Link |
|---|---|
| EP (1) | EP1244625B1 (pt) |
| JP (2) | JP2003516392A (pt) |
| KR (1) | KR100492111B1 (pt) |
| CN (1) | CN1196682C (pt) |
| AR (1) | AR031083A1 (pt) |
| AT (1) | ATE297895T1 (pt) |
| AU (1) | AU779063B2 (pt) |
| BR (1) | BR0016172A (pt) |
| CA (1) | CA2392566A1 (pt) |
| CO (1) | CO5080771A1 (pt) |
| CZ (1) | CZ20022352A3 (pt) |
| DE (1) | DE60020883T2 (pt) |
| DK (1) | DK1244625T3 (pt) |
| ES (1) | ES2243335T3 (pt) |
| GC (1) | GC0000214A (pt) |
| HK (1) | HK1053470A1 (pt) |
| HR (1) | HRP20020467A2 (pt) |
| HU (1) | HUP0203735A3 (pt) |
| IL (2) | IL149622A0 (pt) |
| JO (1) | JO2281B1 (pt) |
| MA (1) | MA26849A1 (pt) |
| MX (1) | MXPA02005240A (pt) |
| MY (1) | MY128003A (pt) |
| NO (1) | NO322910B1 (pt) |
| NZ (1) | NZ518888A (pt) |
| PE (1) | PE20010960A1 (pt) |
| PL (1) | PL364814A1 (pt) |
| PT (1) | PT1244625E (pt) |
| RU (1) | RU2270193C2 (pt) |
| TW (1) | TWI276629B (pt) |
| UY (1) | UY26470A1 (pt) |
| WO (1) | WO2001042215A1 (pt) |
| YU (1) | YU40502A (pt) |
| ZA (1) | ZA200203762B (pt) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6960597B2 (en) | 2000-06-30 | 2005-11-01 | Orth-Mcneil Pharmaceutical, Inc. | Aza-bridged-bicyclic amino acid derivatives as α4 integrin antagonists |
| KR100675036B1 (ko) | 2000-08-18 | 2007-01-29 | 아지노모토 가부시키가이샤 | 신규한 페닐알라닌 유도체 및 이를 포함하는 의약품 |
| DE60124573T2 (de) * | 2000-09-29 | 2007-06-21 | Ajinomoto Co., Inc. | Neue phenylalanin-derivate |
| JP4452899B2 (ja) | 2001-12-13 | 2010-04-21 | 味の素株式会社 | 新規フェニルアラニン誘導体 |
| US7482366B2 (en) | 2001-12-21 | 2009-01-27 | X-Ceptor Therapeutics, Inc. | Modulators of LXR |
| EP1465869B1 (en) | 2001-12-21 | 2013-05-15 | Exelixis Patent Company LLC | Modulators of lxr |
| RU2390520C2 (ru) | 2003-12-22 | 2010-05-27 | Адзиномото Ко., Инк. | Новые производные фенилаланина |
| US7618981B2 (en) * | 2004-05-06 | 2009-11-17 | Cytokinetics, Inc. | Imidazopyridinyl-benzamide anti-cancer agents |
| JP4649476B2 (ja) * | 2004-08-16 | 2011-03-09 | メルク・シャープ・エンド・ドーム・コーポレイション | Ｖｌａ−４拮抗薬 |
| JP4784224B2 (ja) | 2004-09-24 | 2011-10-05 | 味の素株式会社 | 糖鎖転移方法および糖鎖転移酵素 |
| EP2007392A4 (en) * | 2006-02-28 | 2010-04-07 | Elan Pharm Inc | METHOD FOR THE TREATMENT OF INFLAMMATORY AND AUTOIMMUNE DISEASES WITH ALPHA-4-INHIBITABLE COMPOUNDS |
| AR060901A1 (es) * | 2006-05-12 | 2008-07-23 | Jerini Ag | Compuestos heterociclicos para la inhibicion de integrinas y uso de estos |
| CA2714335A1 (en) | 2007-02-20 | 2008-08-28 | Merrimack Pharmaceuticals, Inc. | Methods of treating multiple sclerosis by administration of alpha-fetoprotein in combination with an integrin antagonist |
| AU2009234253C1 (en) | 2008-04-11 | 2015-05-07 | Merrimack Pharmaceuticals, Inc. | Human serum albumin linkers and conjugates thereof |
| IN2012DN00638A (pt) * | 2009-07-23 | 2015-08-21 | Bayer Cropscience Ag | |
| US8877815B2 (en) | 2010-11-16 | 2014-11-04 | Novartis Ag | Substituted carbamoylcycloalkyl acetic acid derivatives as NEP |
| WO2013110680A1 (en) * | 2012-01-27 | 2013-08-01 | F. Hoffmann-La Roche Ag | Integrin antagonist conjugates for targeted delivery to cells expressing vla-4 |
| EP3008056B8 (en) * | 2013-06-11 | 2021-03-03 | Receptos Llc | Novel glp-1 receptor modulators |
| PT3412660T (pt) | 2016-02-05 | 2021-01-13 | Ea Pharma Co Ltd | Derivado de sulfonamida e composição farmacêutica contendo o mesmo |
| PE20211866A1 (es) | 2018-10-30 | 2021-09-21 | Gilead Sciences Inc | Derivados de quinolina como inhibidores de la integrina alfa4beta7 |
| US11174256B2 (en) | 2018-10-30 | 2021-11-16 | Gilead Sciences, Inc. | Imidazopyridine derivatives |
| WO2020092401A1 (en) | 2018-10-30 | 2020-05-07 | Gilead Sciences, Inc. | COMPOUNDS FOR INHIBITION OF ALPHA 4β7 INTEGRIN |
| EP3873897B1 (en) | 2018-10-30 | 2024-08-14 | Gilead Sciences, Inc. | N-benzoyl-phenylalanine derivatives as alpha4beta7 integrin inhibitors for treating inflammatory diseases |
| WO2021030438A1 (en) | 2019-08-14 | 2021-02-18 | Gilead Sciences, Inc. | Compounds for inhibition of alpha 4 beta 7 integrin |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998053817A1 (en) * | 1997-05-29 | 1998-12-03 | Merck & Co., Inc. | Biarylalkanoic acids as cell adhesion inhibitors |
| EP1001764A4 (en) * | 1997-05-29 | 2005-08-24 | Merck & Co Inc | Heterocyclic amides as cell adhesion inhibitors |
| US6197794B1 (en) * | 1998-01-08 | 2001-03-06 | Celltech Therapeutics Limited | Phenylalanine derivatives |
| MY153569A (en) * | 1998-01-20 | 2015-02-27 | Mitsubishi Tanabe Pharma Corp | Inhibitors of ?4 mediated cell adhesion |
| US6329372B1 (en) * | 1998-01-27 | 2001-12-11 | Celltech Therapeutics Limited | Phenylalanine derivatives |
| JP2002504534A (ja) * | 1998-02-26 | 2002-02-12 | セルテック・セラピューティクス・リミテッド | α４インテグリンの阻害剤としてのフェニルアラニン誘導体 |
| GB9811159D0 (en) * | 1998-05-22 | 1998-07-22 | Celltech Therapeutics Ltd | Chemical compounds |
| EP1144365B1 (en) * | 1998-12-22 | 2004-03-17 | Tanabe Seiyaku Co., Ltd. | Inhibitors of alpha-4 beta-1 mediated cell adhesion |
| ATE299490T1 (de) * | 1999-01-22 | 2005-07-15 | Elan Pharm Inc | Multizyklische verbindungen zur hemmung der durch vla-4 vermittelten leukozytenadhäsion |
-
2000
- 2000-11-29 CN CNB008164800A patent/CN1196682C/zh not_active Expired - Fee Related
- 2000-11-29 YU YU40502A patent/YU40502A/sh unknown
- 2000-11-29 JP JP2001543516A patent/JP2003516392A/ja active Pending
- 2000-11-29 AU AU21639/01A patent/AU779063B2/en not_active Ceased
- 2000-11-29 JO JO2000189A patent/JO2281B1/en active
- 2000-11-29 WO PCT/EP2000/011979 patent/WO2001042215A1/en active IP Right Grant
- 2000-11-29 MX MXPA02005240A patent/MXPA02005240A/es active IP Right Grant
- 2000-11-29 AT AT00985117T patent/ATE297895T1/de not_active IP Right Cessation
- 2000-11-29 PL PL00364814A patent/PL364814A1/xx not_active Application Discontinuation
- 2000-11-29 EP EP00985117A patent/EP1244625B1/en not_active Expired - Lifetime
- 2000-11-29 CA CA002392566A patent/CA2392566A1/en not_active Abandoned
- 2000-11-29 HU HU0203735A patent/HUP0203735A3/hu unknown
- 2000-11-29 PT PT00985117T patent/PT1244625E/pt unknown
- 2000-11-29 RU RU2002117419/04A patent/RU2270193C2/ru not_active IP Right Cessation
- 2000-11-29 CZ CZ20022352A patent/CZ20022352A3/cs unknown
- 2000-11-29 NZ NZ518888A patent/NZ518888A/en unknown
- 2000-11-29 ES ES00985117T patent/ES2243335T3/es not_active Expired - Lifetime
- 2000-11-29 KR KR10-2002-7007201A patent/KR100492111B1/ko not_active IP Right Cessation
- 2000-11-29 IL IL14962200A patent/IL149622A0/xx active IP Right Grant
- 2000-11-29 DK DK00985117T patent/DK1244625T3/da active
- 2000-11-29 DE DE60020883T patent/DE60020883T2/de not_active Expired - Lifetime
- 2000-11-29 BR BR0016172-1A patent/BR0016172A/pt not_active Application Discontinuation
- 2000-12-02 GC GCP20001072 patent/GC0000214A/en active
- 2000-12-04 MY MYPI20005689A patent/MY128003A/en unknown
- 2000-12-04 AR ARP000106416A patent/AR031083A1/es not_active Application Discontinuation
- 2000-12-05 CO CO00092690A patent/CO5080771A1/es unknown
- 2000-12-05 TW TW089125889A patent/TWI276629B/zh not_active IP Right Cessation
- 2000-12-05 UY UY26470A patent/UY26470A1/es not_active Application Discontinuation
- 2000-12-06 PE PE2000001306A patent/PE20010960A1/es not_active Application Discontinuation
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2002
- 2002-05-10 ZA ZA200203762A patent/ZA200203762B/xx unknown
- 2002-05-13 IL IL149622A patent/IL149622A/en not_active IP Right Cessation
- 2002-05-28 HR HR20020467A patent/HRP20020467A2/xx not_active Application Discontinuation
- 2002-06-05 NO NO20022650A patent/NO322910B1/no unknown
- 2002-06-05 MA MA26672A patent/MA26849A1/fr unknown
-
2003
- 2003-08-13 HK HK03105803A patent/HK1053470A1/xx not_active IP Right Cessation
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2007
- 2007-10-05 JP JP2007262543A patent/JP2008094842A/ja active Pending
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