JP2002537336A5 - - Google Patents
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- JP2002537336A5 JP2002537336A5 JP2000600648A JP2000600648A JP2002537336A5 JP 2002537336 A5 JP2002537336 A5 JP 2002537336A5 JP 2000600648 A JP2000600648 A JP 2000600648A JP 2000600648 A JP2000600648 A JP 2000600648A JP 2002537336 A5 JP2002537336 A5 JP 2002537336A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- hydrogen
- nitric oxide
- lower 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.)
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- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 56
- 150000001875 compounds Chemical class 0.000 description 49
- 229910052739 hydrogen Inorganic materials 0.000 description 49
- 239000001257 hydrogen Substances 0.000 description 49
- 125000000217 alkyl group Chemical group 0.000 description 45
- 125000003118 aryl group Chemical group 0.000 description 38
- 150000002431 hydrogen Chemical class 0.000 description 33
- 239000002253 acid Substances 0.000 description 30
- 125000000623 heterocyclic group Chemical group 0.000 description 23
- 229920001184 polypeptide Polymers 0.000 description 20
- 125000003545 alkoxy group Chemical group 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 18
- 125000001931 aliphatic group Chemical group 0.000 description 16
- 125000002877 alkyl aryl group Chemical group 0.000 description 16
- 125000000753 cycloalkyl group Chemical group 0.000 description 16
- 229910052736 halogen Inorganic materials 0.000 description 16
- 150000002367 halogens Chemical class 0.000 description 16
- 229920006395 saturated elastomer Polymers 0.000 description 16
- -1 alkoxyhaloalkyl Chemical group 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- 125000004438 haloalkoxy group Chemical group 0.000 description 14
- 239000004215 Carbon black (E152) Substances 0.000 description 12
- 102000008299 Nitric Oxide Synthase Human genes 0.000 description 12
- 108010021487 Nitric Oxide Synthase Proteins 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 239000000066 endothelium dependent relaxing factor Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 9
- 125000004414 alkyl thio group Chemical group 0.000 description 9
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- 125000004103 aminoalkyl group Chemical group 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 150000003857 carboxamides Chemical class 0.000 description 7
- 229940124530 sulfonamide Drugs 0.000 description 7
- 150000003456 sulfonamides Chemical class 0.000 description 7
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 6
- 229930064664 L-arginine Natural products 0.000 description 6
- 235000014852 L-arginine Nutrition 0.000 description 6
- FQWRAVYMZULPNK-UHFFFAOYSA-N N(5)-[(Z)-amino(hydroxyimino)methyl]ornithine Chemical compound OC(=O)C(N)CCCNC(N)=NO FQWRAVYMZULPNK-UHFFFAOYSA-N 0.000 description 6
- 229910002651 NO3 Inorganic materials 0.000 description 6
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 6
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 6
- 125000005431 alkyl carboxamide group Chemical group 0.000 description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 6
- 235000001014 amino acid Nutrition 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 6
- 125000005001 aminoaryl group Chemical group 0.000 description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- KWDSFGYQALRPMG-UHFFFAOYSA-N delta-N-Hydroxy-L-orginin Natural products OC(=O)C(N)CCCN(O)C(N)=N KWDSFGYQALRPMG-UHFFFAOYSA-N 0.000 description 6
- 125000004663 dialkyl amino group Chemical group 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- ICRHORQIUXBEPA-UHFFFAOYSA-N thionitrous acid Chemical group SN=O ICRHORQIUXBEPA-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 5
- 229940069428 antacid Drugs 0.000 description 5
- 239000003159 antacid agent Substances 0.000 description 5
- 230000001458 anti-acid effect Effects 0.000 description 5
- 239000004599 antimicrobial Substances 0.000 description 5
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 229910052797 bismuth Inorganic materials 0.000 description 5
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 5
- 150000001733 carboxylic acid esters Chemical class 0.000 description 5
- 150000001767 cationic compounds Chemical class 0.000 description 5
- 229940111134 coxibs Drugs 0.000 description 5
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229910001411 inorganic cation Inorganic materials 0.000 description 5
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 5
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 5
- 150000002892 organic cations Chemical class 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229940126409 proton pump inhibitor Drugs 0.000 description 5
- 239000000612 proton pump inhibitor Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 description 4
- JCZAVVUIFWZMQI-UHFFFAOYSA-N 1h-thieno[2,3-d]imidazole Chemical compound N1C=NC2=C1C=CS2 JCZAVVUIFWZMQI-UHFFFAOYSA-N 0.000 description 4
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 4
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- XOWVFANEOZMPKG-REOHCLBHSA-N S-nitroso-L-cysteine Chemical compound OC(=O)[C@@H](N)CSN=O XOWVFANEOZMPKG-REOHCLBHSA-N 0.000 description 4
- 125000004947 alkyl aryl amino group Chemical group 0.000 description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 4
- 125000001769 aryl amino group Chemical group 0.000 description 4
- 125000005110 aryl thio group Chemical group 0.000 description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- LKWFWCBKOFKSKI-UHFFFAOYSA-N n-sulfinylpyridine-3-carboxamide Chemical compound O=S=NC(=O)C1=CC=CN=C1 LKWFWCBKOFKSKI-UHFFFAOYSA-N 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 102000004196 processed proteins & peptides Human genes 0.000 description 4
- 108090000765 processed proteins & peptides Proteins 0.000 description 4
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 125000004422 alkyl sulphonamide group Chemical group 0.000 description 3
- 125000000747 amidyl group Chemical group [H][N-]* 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 description 3
- 125000004421 aryl sulphonamide group Chemical group 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 125000005366 cycloalkylthio group Chemical group 0.000 description 3
- 125000004986 diarylamino group Chemical group 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 125000005343 heterocyclic alkyl group Chemical group 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- QTJKCQPXTOYYHJ-BYPYZUCNSA-N (2r)-2-acetamido-3-nitrososulfanylpropanoic acid Chemical compound CC(=O)N[C@H](C(O)=O)CSN=O QTJKCQPXTOYYHJ-BYPYZUCNSA-N 0.000 description 2
- HNIULCDUASSKOM-RQJHMYQMSA-N (2s)-1-[(2s)-2-methyl-3-nitrososulfanylpropanoyl]pyrrolidine-2-carboxylic acid Chemical compound O=NSC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O HNIULCDUASSKOM-RQJHMYQMSA-N 0.000 description 2
- QWPCKAAAWDCDCW-VKHMYHEASA-N (2s)-2-amino-4-nitrososulfanylbutanoic acid Chemical compound OC(=O)[C@@H](N)CCSN=O QWPCKAAAWDCDCW-VKHMYHEASA-N 0.000 description 2
- YFJPZUQXBSAIKG-UHFFFAOYSA-N (4-amino-2h-quinolin-3-ylidene)methanone Chemical group C1=CC=CC2=NCC(=C=O)C(N)=C21 YFJPZUQXBSAIKG-UHFFFAOYSA-N 0.000 description 2
- BMCBJKLELCZGBF-UHFFFAOYSA-N 1-[8-(2-hydroxyethoxy)-4-(2-methylanilino)quinolin-3-yl]butan-1-one Chemical compound CCCC(=O)C1=CN=C2C(OCCO)=CC=CC2=C1NC1=CC=CC=C1C BMCBJKLELCZGBF-UHFFFAOYSA-N 0.000 description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
- ARFGGIRJBPTBPP-UHFFFAOYSA-N 2-[[4-(2,2,3,3,4,4,4-heptafluorobutoxy)pyridin-2-yl]methylsulfinyl]-1h-thieno[3,4-d]imidazole Chemical compound FC(F)(F)C(F)(F)C(F)(F)COC1=CC=NC(CS(=O)C=2NC3=CSC=C3N=2)=C1 ARFGGIRJBPTBPP-UHFFFAOYSA-N 0.000 description 2
- YNFBMDWHEHETJW-UHFFFAOYSA-N 2-pyridin-2-yl-1h-benzimidazole Chemical compound N1=CC=CC=C1C1=NC2=CC=CC=C2N1 YNFBMDWHEHETJW-UHFFFAOYSA-N 0.000 description 2
- LNIVYCWEFYEKNR-UHFFFAOYSA-N 2-pyrimidin-2-yl-3,4,4a,5-tetrahydro-1h-isoquinoline Chemical compound C1C2=CC=CCC2CCN1C1=NC=CC=N1 LNIVYCWEFYEKNR-UHFFFAOYSA-N 0.000 description 2
- YZVXCSZASWLVLC-UHFFFAOYSA-N 2-sulfinyl-3h-pyridine-3-carboxamide Chemical group NC(=O)C1C=CC=NC1=S=O YZVXCSZASWLVLC-UHFFFAOYSA-N 0.000 description 2
- MMVYXORYIKSBLT-UHFFFAOYSA-N 4-fluoro-2-(pyridin-2-ylmethylsulfinyl)-1h-benzimidazole Chemical compound N1C=2C(F)=CC=CC=2N=C1S(=O)CC1=CC=CC=N1 MMVYXORYIKSBLT-UHFFFAOYSA-N 0.000 description 2
- BDFFOEAQENGFSK-UHFFFAOYSA-N 5-[cyano(nitroso)amino]-2-hydroxypentanamide Chemical compound NC(=O)C(O)CCCN(N=O)C#N BDFFOEAQENGFSK-UHFFFAOYSA-N 0.000 description 2
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 2
- ZBFDAUIVDSSISP-UHFFFAOYSA-N 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methylsulfinyl]-1H-imidazo[4,5-b]pyridine Chemical compound N=1C2=NC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C ZBFDAUIVDSSISP-UHFFFAOYSA-N 0.000 description 2
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 2
- 102000004452 Arginase Human genes 0.000 description 2
- 108700024123 Arginases Proteins 0.000 description 2
- QUOGESRFPZDMMT-UHFFFAOYSA-N L-Homoarginine Natural products OC(=O)C(N)CCCCNC(N)=N QUOGESRFPZDMMT-UHFFFAOYSA-N 0.000 description 2
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 2
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- QUOGESRFPZDMMT-YFKPBYRVSA-N L-homoarginine Chemical compound OC(=O)[C@@H](N)CCCCNC(N)=N QUOGESRFPZDMMT-YFKPBYRVSA-N 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 description 2
- 108091034117 Oligonucleotide Proteins 0.000 description 2
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 2
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 2
- IQPSEEYGBUAQFF-UHFFFAOYSA-N Pantoprazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC=C(OC(F)F)C=C3N=2)=C1OC IQPSEEYGBUAQFF-UHFFFAOYSA-N 0.000 description 2
- ZIIQCSMRQKCOCT-YFKPBYRVSA-N S-nitroso-N-acetyl-D-penicillamine Chemical compound CC(=O)N[C@@H](C(O)=O)C(C)(C)SN=O ZIIQCSMRQKCOCT-YFKPBYRVSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- 229960002173 citrulline Drugs 0.000 description 2
- 235000013477 citrulline Nutrition 0.000 description 2
- SUBDBMMJDZJVOS-DEOSSOPVSA-N esomeprazole Chemical compound C([S@](=O)C1=NC2=CC=C(C=C2N1)OC)C1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-DEOSSOPVSA-N 0.000 description 2
- 229960004770 esomeprazole Drugs 0.000 description 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 2
- 229960002743 glutamine Drugs 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 229960003174 lansoprazole Drugs 0.000 description 2
- MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 description 2
- 229960003646 lysine Drugs 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- MALPZYQJEDBIAK-UHFFFAOYSA-N n-(4-fluorophenyl)-4,5-dimethyl-6-(1-methyl-3,4-dihydro-1h-isoquinolin-2-yl)pyrimidin-2-amine;hydron;chloride Chemical compound Cl.C1CC2=CC=CC=C2C(C)N1C(C(=C(C)N=1)C)=NC=1NC1=CC=C(F)C=C1 MALPZYQJEDBIAK-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229960000381 omeprazole Drugs 0.000 description 2
- 229960003104 ornithine Drugs 0.000 description 2
- 229960005019 pantoprazole Drugs 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 229960004157 rabeprazole Drugs 0.000 description 2
- YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 description 2
- 230000002040 relaxant effect Effects 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229950008375 tenatoprazole Drugs 0.000 description 2
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 2
- 229940125670 thienopyridine Drugs 0.000 description 2
- 239000002175 thienopyridine Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 description 1
- 125000004171 alkoxy aryl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000005140 aralkylsulfonyl group Chemical group 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 210000003038 endothelium Anatomy 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000002840 nitric oxide donor Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12211199P | 1999-02-26 | 1999-02-26 | |
| US60/122,111 | 1999-02-26 | ||
| PCT/US2000/002524 WO2000050037A1 (en) | 1999-02-26 | 2000-02-25 | Nitrosated and nitrosylated proton pump inhibitors, compositions and methods of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002537336A JP2002537336A (ja) | 2002-11-05 |
| JP2002537336A5 true JP2002537336A5 (https=) | 2007-04-05 |
Family
ID=22400684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000600648A Pending JP2002537336A (ja) | 1999-02-26 | 2000-02-25 | ニトロソ化およびニトロシル化されたプロトンポンプ阻害剤、組成物および使用方法 |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1154771A4 (https=) |
| JP (1) | JP2002537336A (https=) |
| AU (2) | AU781133B2 (https=) |
| CA (1) | CA2362930C (https=) |
| WO (1) | WO2000050037A1 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0002476D0 (sv) | 2000-06-30 | 2000-06-30 | Astrazeneca Ab | New compounds |
| EP1453493A2 (en) * | 2001-11-19 | 2004-09-08 | ALTANA Pharma AG | Reversible proton pump inhibitors for the treatment of airway disorders |
| TW200403072A (en) * | 2002-01-23 | 2004-03-01 | Upjohn Co | Combination therapy for the treatment of bacterial infections |
| EP1487447A1 (en) * | 2002-03-14 | 2004-12-22 | ALTANA Pharma AG | Use of proton pump inhibitors for the treatment of airway disorders |
| WO2003082854A1 (en) * | 2002-03-29 | 2003-10-09 | Zeria Pharmaceutical Co., Ltd. | 1-n-aminobenzimidazole derivatives |
| JP2005537223A (ja) * | 2002-04-05 | 2005-12-08 | ニトロメッド，インク． | 酸化窒素供与体、組成物および使用法 |
| WO2004012659A2 (en) * | 2002-08-01 | 2004-02-12 | Nitromed, Inc. | Nitrosated proton pump inhibitors, compositions and methods of use |
| FR2845915B1 (fr) * | 2002-10-21 | 2006-06-23 | Negma Gild | Utilisation du tenatoprazole pour le traitement du reflux gastro-oesophagien |
| FR2845917B1 (fr) * | 2002-10-21 | 2006-07-07 | Negma Gild | Composition pharmaceutique associant le tenatoprazole et un anti-inflammatoire |
| EP1718303A4 (en) * | 2004-02-10 | 2010-09-01 | Santarus Inc | COMBINATION OF INHIBITOR OF PROTON PUMP, BUFFER AND NON-STEROIDAL ANTI-INFLAMMATORY DRUG |
| TW200606163A (en) * | 2004-04-22 | 2006-02-16 | Eisai Co Ltd | Imidazopyridine compound |
| US20070015782A1 (en) | 2005-04-15 | 2007-01-18 | Eisai Co., Ltd. | Benzimidazole compound |
| US9040564B2 (en) | 2005-04-28 | 2015-05-26 | Eisai R&D Management Co., Ltd. | Stabilized composition |
| WO2007016677A2 (en) | 2005-08-02 | 2007-02-08 | Nitromed, Inc. | Nitric oxide enhancing antimicrobial compounds, compositions and methods of use |
| JP5075254B2 (ja) | 2011-01-07 | 2012-11-21 | スノーデン株式会社 | 胃酸及びガストリンの産生を抑制する乳酸菌 |
| CN115569196B (zh) * | 2020-02-26 | 2024-06-18 | 上海科技大学 | 多酚类物质在抗冠状病毒中的应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05117268A (ja) * | 1991-10-22 | 1993-05-14 | Yoshitomi Pharmaceut Ind Ltd | ピリジン化合物 |
| TW276996B (https=) * | 1992-04-24 | 1996-06-01 | Astra Ab | |
| EP0639644A1 (de) * | 1993-08-16 | 1995-02-22 | Ciba-Geigy Ag | Neue Makrolide und ihre Verwendung |
| WO1995034554A1 (de) * | 1994-06-10 | 1995-12-21 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Substituierte arylalkylthioalkylthiopyridine zur bekämpfung von helicobacter-bakterien |
| FI964908L (fi) * | 1994-06-10 | 1996-12-09 | Byk Gulden Lomberg Chem Fab | Helicobacter-bakteerien torjuntaan tarkoitetut tiopyridiinit |
| DE4420523A1 (de) * | 1994-06-13 | 1995-12-14 | Cassella Ag | Verwendung von NO-freisetzenden Verbindungen zur Behandlung und Vorbeugung von systemischen Entzündungssyndromen |
| SE9500422D0 (sv) * | 1995-02-06 | 1995-02-06 | Astra Ab | New oral pharmaceutical dosage forms |
| US5703073A (en) * | 1995-04-19 | 1997-12-30 | Nitromed, Inc. | Compositions and methods to prevent toxicity induced by nonsteroidal antiinflammatory drugs |
| US6132768A (en) * | 1995-07-05 | 2000-10-17 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Oral pharmaceutical composition with delayed release of active ingredient for reversible proton pump inhibitors |
| EP0941102A1 (en) * | 1996-11-22 | 1999-09-15 | The Procter & Gamble Company | Compositions for the treatment of gastrointestinal disorders containing bismuth and nsaid |
| EE03690B1 (et) * | 1996-12-20 | 2002-04-15 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Imidasopüridasiinid, neid sisaldav ravim ja nendekasutamine |
| EP0983263A1 (en) * | 1997-05-30 | 2000-03-08 | Dr. Reddy's Research Foundation | Novel benzimidazole derivatives as antiulcer agents, process for their preparation and pharmaceutical compositions containing them |
-
2000
- 2000-02-25 JP JP2000600648A patent/JP2002537336A/ja active Pending
- 2000-02-25 EP EP00910039A patent/EP1154771A4/en not_active Withdrawn
- 2000-02-25 AU AU32196/00A patent/AU781133B2/en not_active Ceased
- 2000-02-25 CA CA2362930A patent/CA2362930C/en not_active Expired - Fee Related
- 2000-02-25 WO PCT/US2000/002524 patent/WO2000050037A1/en not_active Ceased
-
2005
- 2005-06-10 AU AU2005202553A patent/AU2005202553A1/en not_active Abandoned
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