JP2001517245A - 細胞接着阻害薬としてのビアリールアルカン酸類 - Google Patents
細胞接着阻害薬としてのビアリールアルカン酸類Info
- Publication number
- JP2001517245A JP2001517245A JP50093899A JP50093899A JP2001517245A JP 2001517245 A JP2001517245 A JP 2001517245A JP 50093899 A JP50093899 A JP 50093899A JP 50093899 A JP50093899 A JP 50093899A JP 2001517245 A JP2001517245 A JP 2001517245A
- Authority
- JP
- Japan
- Prior art keywords
- prolyl
- phenylalanine
- dichlorobenzenesulfonyl
- methyl
- 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.)
- Withdrawn
Links
- 230000021164 cell adhesion Effects 0.000 title claims abstract description 15
- 239000002253 acid Substances 0.000 title description 33
- 150000007513 acids Chemical class 0.000 title description 10
- 239000003112 inhibitor Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 126
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 230000001404 mediated effect Effects 0.000 claims abstract description 7
- 208000006673 asthma Diseases 0.000 claims abstract description 6
- 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 6
- 206010061218 Inflammation Diseases 0.000 claims abstract description 5
- 230000004054 inflammatory process Effects 0.000 claims abstract description 5
- -1 3,4-dimethoxybenzenesulfonyl Chemical group 0.000 claims description 78
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 125000001424 substituent group Chemical group 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 45
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 42
- 229960005190 phenylalanine Drugs 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 235000008729 phenylalanine Nutrition 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- CSTQBAFBBPINPO-ZEQRLZLVSA-N (2s)-2-[[(2s)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carbonyl]amino]-3-[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)[C@H]1N(CCC1)S(=O)(=O)C=1C=C(Cl)C=C(Cl)C=1)C(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 CSTQBAFBBPINPO-ZEQRLZLVSA-N 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- JFSVPFIOVGIBHH-ZEQRLZLVSA-N (2s)-3-[4-(2-carbamoylphenyl)phenyl]-2-[[(2s)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carbonyl]amino]propanoic acid Chemical compound NC(=O)C1=CC=CC=C1C(C=C1)=CC=C1C[C@@H](C(O)=O)NC(=O)[C@H]1N(S(=O)(=O)C=2C=C(Cl)C=C(Cl)C=2)CCC1 JFSVPFIOVGIBHH-ZEQRLZLVSA-N 0.000 claims description 4
- BQNRXIZVOZSMLS-DQEYMECFSA-N (2s)-3-[4-(2-cyanophenyl)phenyl]-2-[[(2s)-1-(3-fluorophenyl)sulfonylpyrrolidine-2-carbonyl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)[C@H]1N(CCC1)S(=O)(=O)C=1C=C(F)C=CC=1)C(C=C1)=CC=C1C1=CC=CC=C1C#N BQNRXIZVOZSMLS-DQEYMECFSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- XUTQXXFXBYIPCM-DQEYMECFSA-N (2s)-2-[[(2s)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carbonyl]-methylamino]-3-[4-(2-methoxyphenyl)phenyl]propanoic acid Chemical compound COC1=CC=CC=C1C(C=C1)=CC=C1C[C@@H](C(O)=O)N(C)C(=O)[C@H]1N(S(=O)(=O)C=2C=C(Cl)C=C(Cl)C=2)CCC1 XUTQXXFXBYIPCM-DQEYMECFSA-N 0.000 claims description 3
- XHCXORPSNPUSKF-ZEQRLZLVSA-N (2s)-2-[[(2s)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carbonyl]amino]-3-[4-(4-fluorophenyl)phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)[C@H]1N(CCC1)S(=O)(=O)C=1C=C(Cl)C=C(Cl)C=1)C(C=C1)=CC=C1C1=CC=C(F)C=C1 XHCXORPSNPUSKF-ZEQRLZLVSA-N 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- MMYBBVWYPAIKBK-DQEYMECFSA-N (2s)-2-[[(2s)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carbonyl]amino]-3-[4-(2-formylphenyl)phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)[C@H]1N(CCC1)S(=O)(=O)C=1C=C(Cl)C=C(Cl)C=1)C(C=C1)=CC=C1C1=CC=CC=C1C=O MMYBBVWYPAIKBK-DQEYMECFSA-N 0.000 claims description 2
- SITGJFUZUFHSHU-ZEQRLZLVSA-N (2s)-2-[[(2s)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carbonyl]amino]-3-[4-(2-methoxyphenyl)phenyl]propanoic acid Chemical compound COC1=CC=CC=C1C(C=C1)=CC=C1C[C@@H](C(O)=O)NC(=O)[C@H]1N(S(=O)(=O)C=2C=C(Cl)C=C(Cl)C=2)CCC1 SITGJFUZUFHSHU-ZEQRLZLVSA-N 0.000 claims description 2
- FRQKIVHZBNERQJ-QAVFMOBOSA-N (2s)-2-[[(2s)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carbonyl]amino]-3-[4-(2-methylsulfinylphenyl)phenyl]propanoic acid Chemical compound CS(=O)C1=CC=CC=C1C(C=C1)=CC=C1C[C@@H](C(O)=O)NC(=O)[C@H]1N(S(=O)(=O)C=2C=C(Cl)C=C(Cl)C=2)CCC1 FRQKIVHZBNERQJ-QAVFMOBOSA-N 0.000 claims description 2
- HBHMXAWUVLNJOM-ZEQRLZLVSA-N (2s)-2-[[(2s)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carbonyl]amino]-3-[4-(2-methylsulfonylphenyl)phenyl]propanoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(C=C1)=CC=C1C[C@@H](C(O)=O)NC(=O)[C@H]1N(S(=O)(=O)C=2C=C(Cl)C=C(Cl)C=2)CCC1 HBHMXAWUVLNJOM-ZEQRLZLVSA-N 0.000 claims description 2
- OTYRYXBQALGUOQ-ZEQRLZLVSA-N (2s)-2-[[(2s)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carbonyl]amino]-3-[4-[4-(trifluoromethyl)phenyl]phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)[C@H]1N(CCC1)S(=O)(=O)C=1C=C(Cl)C=C(Cl)C=1)C(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 OTYRYXBQALGUOQ-ZEQRLZLVSA-N 0.000 claims description 2
- HYAQNAKWIMLYPS-ZODMCCGTSA-N (2s)-2-[[(2s,4r)-4-amino-1-(benzenesulfonyl)pyrrolidine-2-carbonyl]amino]-3-[4-(2-cyanophenyl)phenyl]propanoic acid Chemical compound N1([C@@H](C[C@H](C1)N)C(=O)N[C@@H](CC=1C=CC(=CC=1)C=1C(=CC=CC=1)C#N)C(O)=O)S(=O)(=O)C1=CC=CC=C1 HYAQNAKWIMLYPS-ZODMCCGTSA-N 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 2
- 201000010105 allergic rhinitis Diseases 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- PZNZQTFPTMVVJA-PMACEKPBSA-N (2S)-3-[4-(2-cyanophenyl)phenyl]-2-[[(2S)-1-methylpyrrolidine-2-carbonyl]amino]propanoic acid Chemical compound CN1[C@@H](CCC1)C(=O)N[C@@H](CC1=CC=C(C=C1)C1=C(C=CC=C1)C#N)C(=O)O PZNZQTFPTMVVJA-PMACEKPBSA-N 0.000 claims 5
- WIRZOLKKGXATQC-OALUTQOASA-N (2S)-3-[4-(2-methoxyphenyl)phenyl]-2-[[(2S)-1-methylpyrrolidine-2-carbonyl]amino]propanoic acid Chemical compound CN1[C@@H](CCC1)C(=O)N[C@@H](CC1=CC=C(C=C1)C1=C(C=CC=C1)OC)C(=O)O WIRZOLKKGXATQC-OALUTQOASA-N 0.000 claims 3
- PZNZQTFPTMVVJA-WOJBJXKFSA-N (2R)-3-[4-(2-cyanophenyl)phenyl]-2-[[(2R)-1-methylpyrrolidine-2-carbonyl]amino]propanoic acid Chemical compound CN1[C@H](CCC1)C(=O)N[C@H](CC1=CC=C(C=C1)C1=C(C=CC=C1)C#N)C(=O)O PZNZQTFPTMVVJA-WOJBJXKFSA-N 0.000 claims 1
- WTCPOKULWMVYBW-ROUUACIJSA-N (2S)-2-[[(2S)-1-methylpyrrolidine-2-carbonyl]amino]-3-(4-pyridin-3-ylphenyl)propanoic acid Chemical compound CN1[C@@H](CCC1)C(=O)N[C@@H](CC1=CC=C(C=C1)C=1C=NC=CC=1)C(=O)O WTCPOKULWMVYBW-ROUUACIJSA-N 0.000 claims 1
- UPFZSDJHIPCUQO-IRXDYDNUSA-N (2S)-2-[[(2S)-1-methylpyrrolidine-2-carbonyl]amino]-3-(4-pyrimidin-5-ylphenyl)propanoic acid Chemical compound CN1[C@@H](CCC1)C(=O)N[C@@H](CC1=CC=C(C=C1)C=1C=NC=NC=1)C(=O)O UPFZSDJHIPCUQO-IRXDYDNUSA-N 0.000 claims 1
- MTXLIOUFHKEABE-GJZGRUSLSA-N (2S)-2-[[(2S)-1-methylpyrrolidine-2-carbonyl]amino]-3-[4-(1,3-thiazol-2-yl)phenyl]propanoic acid Chemical compound CN1[C@@H](CCC1)C(=O)N[C@@H](CC1=CC=C(C=C1)C=1SC=CN=1)C(=O)O MTXLIOUFHKEABE-GJZGRUSLSA-N 0.000 claims 1
- BRSIDIMEKMMBJV-OALUTQOASA-N (2S)-2-[[(2S)-1-methylpyrrolidine-2-carbonyl]amino]-3-[4-(2-methylsulfanylphenyl)phenyl]propanoic acid Chemical compound CN1[C@@H](CCC1)C(=O)N[C@@H](CC1=CC=C(C=C1)C1=C(C=CC=C1)SC)C(=O)O BRSIDIMEKMMBJV-OALUTQOASA-N 0.000 claims 1
- LLRAXQXGVCCOHX-IRXDYDNUSA-N (2S)-2-[[(2S)-1-methylpyrrolidine-2-carbonyl]amino]-3-[4-[2-(trifluoromethyl)-1,3-benzoxazol-4-yl]phenyl]propanoic acid Chemical compound CN1[C@@H](CCC1)C(=O)N[C@@H](CC1=CC=C(C=C1)C1=CC=CC2=C1N=C(O2)C(F)(F)F)C(=O)O LLRAXQXGVCCOHX-IRXDYDNUSA-N 0.000 claims 1
- IGYDCCRXOGZIFO-DPFTZIENSA-N (2S)-2-[[(2S,4R)-1-(benzenesulfonyl)-4-[(2-phenylacetyl)amino]pyrrolidine-2-carbonyl]amino]-3-[4-(2-cyanophenyl)phenyl]propanoic acid Chemical compound OC(=O)[C@H](Cc1ccc(cc1)-c1ccccc1C#N)NC(=O)[C@@H]1C[C@H](CN1S(=O)(=O)c1ccccc1)NC(=O)Cc1ccccc1 IGYDCCRXOGZIFO-DPFTZIENSA-N 0.000 claims 1
- RFYLBZHBHBINBS-HOJAQTOUSA-N (2S)-2-[[(2S,4R)-4-amino-1-methylsulfonylpyrrolidine-2-carbonyl]amino]-3-[4-(2-cyanophenyl)phenyl]propanoic acid Chemical compound CS(=O)(=O)N1[C@@H](C[C@H](C1)N)C(=O)N[C@@H](CC1=CC=C(C=C1)C1=C(C=CC=C1)C#N)C(=O)O RFYLBZHBHBINBS-HOJAQTOUSA-N 0.000 claims 1
- CVTXAEMRSIPWRY-HJNYFJLDSA-N (2S)-2-[[(2S,4R)-4-amino-1-propan-2-ylsulfonylpyrrolidine-2-carbonyl]amino]-3-[4-(2-cyanophenyl)phenyl]propanoic acid Chemical compound C(C)(C)S(=O)(=O)N1[C@@H](C[C@H](C1)N)C(=O)N[C@@H](CC1=CC=C(C=C1)C1=C(C=CC=C1)C#N)C(=O)O CVTXAEMRSIPWRY-HJNYFJLDSA-N 0.000 claims 1
- IGYDCCRXOGZIFO-MHDHXZMLSA-N (2S)-2-[[(2S,4S)-1-(benzenesulfonyl)-4-[(2-phenylacetyl)amino]pyrrolidine-2-carbonyl]amino]-3-[4-(2-cyanophenyl)phenyl]propanoic acid Chemical compound OC(=O)[C@H](Cc1ccc(cc1)-c1ccccc1C#N)NC(=O)[C@@H]1C[C@@H](CN1S(=O)(=O)c1ccccc1)NC(=O)Cc1ccccc1 IGYDCCRXOGZIFO-MHDHXZMLSA-N 0.000 claims 1
- HYAQNAKWIMLYPS-TUSQITKMSA-N (2S)-2-[[(2S,4S)-4-amino-1-(benzenesulfonyl)pyrrolidine-2-carbonyl]amino]-3-[4-(2-cyanophenyl)phenyl]propanoic acid Chemical compound C1(=CC=CC=C1)S(=O)(=O)N1[C@@H](C[C@@H](C1)N)C(=O)N[C@@H](CC1=CC=C(C=C1)C1=C(C=CC=C1)C#N)C(=O)O HYAQNAKWIMLYPS-TUSQITKMSA-N 0.000 claims 1
- OJEVLKCEYYVHJZ-BBRMVZONSA-N (2S)-2-[[4-(2-methoxyphenyl)thiophen-2-yl]-[(2S)-1-methylpyrrolidine-2-carbonyl]amino]propanoic acid Chemical compound CN1[C@@H](CCC1)C(=O)N([C@@H](C)C(=O)O)C=1SC=C(C=1)C1=C(C=CC=C1)OC OJEVLKCEYYVHJZ-BBRMVZONSA-N 0.000 claims 1
- ZDLGDQUOUXQLSR-SFTDATJTSA-N (2S)-3-[4-(1-methylindol-7-yl)phenyl]-2-[[(2S)-1-methylpyrrolidine-2-carbonyl]amino]propanoic acid Chemical compound CN1[C@@H](CCC1)C(=O)N[C@@H](CC1=CC=C(C=C1)C=1C=CC=C2C=CN(C=12)C)C(=O)O ZDLGDQUOUXQLSR-SFTDATJTSA-N 0.000 claims 1
- MESBSMYPCKDLHO-PMACEKPBSA-N (2S)-3-[4-(1H-indol-7-yl)phenyl]-2-[[(2S)-1-methylpyrrolidine-2-carbonyl]amino]propanoic acid Chemical compound CN1[C@@H](CCC1)C(=O)N[C@@H](CC1=CC=C(C=C1)C=1C=CC=C2C=CNC=12)C(=O)O MESBSMYPCKDLHO-PMACEKPBSA-N 0.000 claims 1
- PZNZQTFPTMVVJA-VQTJNVASSA-N (2S)-3-[4-(2-cyanophenyl)phenyl]-2-[[(2R)-1-methylpyrrolidine-2-carbonyl]amino]propanoic acid Chemical compound CN1[C@H](CCC1)C(=O)N[C@@H](CC1=CC=C(C=C1)C1=C(C=CC=C1)C#N)C(=O)O PZNZQTFPTMVVJA-VQTJNVASSA-N 0.000 claims 1
- YOSDYTWRMLQQEJ-SFTDATJTSA-N (2S)-3-[4-(2-cyanophenyl)phenyl]-2-[methyl-[(2S)-piperidine-2-carbonyl]amino]propanoic acid Chemical compound CN([C@@H](CC1=CC=C(C=C1)C1=C(C=CC=C1)C#N)C(=O)O)C([C@H]1NCCCC1)=O YOSDYTWRMLQQEJ-SFTDATJTSA-N 0.000 claims 1
- WCPPZSFWRLFLIG-PMACEKPBSA-N (2S)-3-[4-(2-formylphenyl)phenyl]-2-[[(2S)-1-methylpyrrolidine-2-carbonyl]amino]propanoic acid Chemical compound CN1[C@@H](CCC1)C(=O)N[C@@H](CC1=CC=C(C=C1)C1=C(C=CC=C1)C=O)C(=O)O WCPPZSFWRLFLIG-PMACEKPBSA-N 0.000 claims 1
- UJKBNSURMMMXJU-PMACEKPBSA-N (2S)-3-[4-(3-cyanophenyl)phenyl]-2-[[(2S)-1-methylpyrrolidine-2-carbonyl]amino]propanoic acid Chemical compound CN1[C@@H](CCC1)C(=O)N[C@@H](CC1=CC=C(C=C1)C1=CC(=CC=C1)C#N)C(=O)O UJKBNSURMMMXJU-PMACEKPBSA-N 0.000 claims 1
- VWRHWNNVYAIWTJ-OALUTQOASA-N (2S)-3-[4-(4-fluorophenyl)phenyl]-2-[[(2S)-1-methylpyrrolidine-2-carbonyl]amino]propanoic acid Chemical compound CN1[C@@H](CCC1)C(=O)N[C@@H](CC1=CC=C(C=C1)C1=CC=C(C=C1)F)C(=O)O VWRHWNNVYAIWTJ-OALUTQOASA-N 0.000 claims 1
- ZMSFXIYMZGKTJU-ZEQRLZLVSA-N (2s)-2-[[(2s)-1-(1,3-benzothiazol-2-ylsulfonyl)pyrrolidine-2-carbonyl]amino]-3-[4-(2-cyanophenyl)phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)[C@H]1N(CCC1)S(=O)(=O)C=1SC2=CC=CC=C2N=1)C(C=C1)=CC=C1C1=CC=CC=C1C#N ZMSFXIYMZGKTJU-ZEQRLZLVSA-N 0.000 claims 1
- BZHTUPYVTUYUCZ-GOTSBHOMSA-N (2s)-2-[[(2s)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carbonyl]amino]-3-(4-pyridin-2-ylphenyl)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)[C@H]1N(CCC1)S(=O)(=O)C=1C=C(Cl)C=C(Cl)C=1)C(C=C1)=CC=C1C1=CC=CC=N1 BZHTUPYVTUYUCZ-GOTSBHOMSA-N 0.000 claims 1
- VVYXQHACKYVQHE-GOTSBHOMSA-N (2s)-2-[[(2s)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carbonyl]amino]-3-(4-pyridin-3-ylphenyl)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)[C@H]1N(CCC1)S(=O)(=O)C=1C=C(Cl)C=C(Cl)C=1)C(C=C1)=CC=C1C1=CC=CN=C1 VVYXQHACKYVQHE-GOTSBHOMSA-N 0.000 claims 1
- ZZBLMTRHJGUOQN-VXKWHMMOSA-N (2s)-2-[[(2s)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carbonyl]amino]-3-(4-pyrimidin-5-ylphenyl)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)[C@H]1N(CCC1)S(=O)(=O)C=1C=C(Cl)C=C(Cl)C=1)C(C=C1)=CC=C1C1=CN=CN=C1 ZZBLMTRHJGUOQN-VXKWHMMOSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06165—Dipeptides with the first amino acid being heterocyclic and Pro-amino acid; Derivatives thereof
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
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- 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
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- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- Pulmonology (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Otolaryngology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Optical Filters (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Peptides Or Proteins (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4785697P | 1997-05-29 | 1997-05-29 | |
| GBGB9714316.8A GB9714316D0 (en) | 1997-07-07 | 1997-07-07 | Biarylalkanoic acids as cell adhesion inhibitors |
| US6683197P | 1997-11-25 | 1997-11-25 | |
| GB9800680.2 | 1998-01-14 | ||
| GB60/066,831 | 1998-01-14 | ||
| GB60/047,856 | 1998-01-14 | ||
| GB9714316.8 | 1998-01-14 | ||
| GBGB9800680.2A GB9800680D0 (en) | 1998-01-14 | 1998-01-14 | Biarylalkanoic acids as cell adhesion inhibitors |
| PCT/US1998/010951 WO1998053817A1 (en) | 1997-05-29 | 1998-05-29 | Biarylalkanoic acids as cell adhesion inhibitors |
Publications (2)
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| JP2001517245A true JP2001517245A (ja) | 2001-10-02 |
| JP2001517245A5 JP2001517245A5 (enExample) | 2005-12-02 |
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| JP (1) | JP2001517245A (enExample) |
| AT (1) | ATE318841T1 (enExample) |
| AU (1) | AU726585B2 (enExample) |
| CA (1) | CA2291762A1 (enExample) |
| DE (1) | DE69833654T2 (enExample) |
| ES (1) | ES2257808T3 (enExample) |
| WO (1) | WO1998053817A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2006516624A (ja) * | 2003-01-24 | 2006-07-06 | エラン ファーマシューティカルズ，インコーポレイテッド | 脱髄疾患および麻痺のための組成物ならびに再有髄化剤を投与することによるそれらの治療 |
| JP2007536355A (ja) * | 2004-05-07 | 2007-12-13 | ラボラトワール フルニエ エス・アー | Ｌｘｒ受容体モジュレーター |
| JP2009536961A (ja) * | 2006-05-12 | 2009-10-22 | イエリニ・アクチェンゲゼルシャフト | インテグリンを阻害する新規複素環化合物及びその使用 |
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| TW223629B (enExample) * | 1992-03-06 | 1994-05-11 | Hoffmann La Roche | |
| US6306840B1 (en) * | 1995-01-23 | 2001-10-23 | Biogen, Inc. | Cell adhesion inhibitors |
| US5707985A (en) * | 1995-06-07 | 1998-01-13 | Tanabe Seiyaku Co. Ltd. | Naphthyl-, quinolyl- and isoquinolyl- sulfonamide derivatives as cell adhesion modulators |
| US6248713B1 (en) * | 1995-07-11 | 2001-06-19 | Biogen, Inc. | Cell adhesion inhibitors |
| EP1001764A4 (en) * | 1997-05-29 | 2005-08-24 | Merck & Co Inc | HETEROCYCLIC AMIDE COMPOUNDS AS INHIBITORS OF CELL ADHESION |
| JP2002501537A (ja) * | 1997-05-29 | 2002-01-15 | メルク エンド カンパニー インコーポレーテッド | 細胞接着阻害薬としてのスルホンアミド類 |
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- 1998-05-29 AU AU77031/98A patent/AU726585B2/en not_active Ceased
- 1998-05-29 CA CA002291762A patent/CA2291762A1/en not_active Abandoned
- 1998-05-29 DE DE69833654T patent/DE69833654T2/de not_active Expired - Fee Related
- 1998-05-29 AT AT98924988T patent/ATE318841T1/de not_active IP Right Cessation
- 1998-05-29 JP JP50093899A patent/JP2001517245A/ja not_active Withdrawn
- 1998-05-29 ES ES98924988T patent/ES2257808T3/es not_active Expired - Lifetime
- 1998-05-29 EP EP98924988A patent/EP1017382B1/en not_active Expired - Lifetime
- 1998-05-29 WO PCT/US1998/010951 patent/WO1998053817A1/en not_active Ceased
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006516624A (ja) * | 2003-01-24 | 2006-07-06 | エラン ファーマシューティカルズ，インコーポレイテッド | 脱髄疾患および麻痺のための組成物ならびに再有髄化剤を投与することによるそれらの治療 |
| JP2007536355A (ja) * | 2004-05-07 | 2007-12-13 | ラボラトワール フルニエ エス・アー | Ｌｘｒ受容体モジュレーター |
| JP4892475B2 (ja) * | 2004-05-07 | 2012-03-07 | ラボラトワール フルニエ エス・アー | Ｌｘｒ受容体モジュレーター |
| JP2009536961A (ja) * | 2006-05-12 | 2009-10-22 | イエリニ・アクチェンゲゼルシャフト | インテグリンを阻害する新規複素環化合物及びその使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE318841T1 (de) | 2006-03-15 |
| AU726585B2 (en) | 2000-11-09 |
| EP1017382A1 (en) | 2000-07-12 |
| DE69833654D1 (de) | 2006-04-27 |
| EP1017382B1 (en) | 2006-03-01 |
| CA2291762A1 (en) | 1998-12-03 |
| EP1017382A4 (en) | 2000-08-30 |
| ES2257808T3 (es) | 2006-08-01 |
| WO1998053817A1 (en) | 1998-12-03 |
| AU7703198A (en) | 1998-12-30 |
| DE69833654T2 (de) | 2006-12-14 |
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