JP2005539013A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2005539013A5 JP2005539013A5 JP2004526261A JP2004526261A JP2005539013A5 JP 2005539013 A5 JP2005539013 A5 JP 2005539013A5 JP 2004526261 A JP2004526261 A JP 2004526261A JP 2004526261 A JP2004526261 A JP 2004526261A JP 2005539013 A5 JP2005539013 A5 JP 2005539013A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- nitrosated
- compound
- ono
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 70
- 229910052739 hydrogen Inorganic materials 0.000 claims 54
- 239000001257 hydrogen Substances 0.000 claims 54
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims 45
- 125000000217 alkyl group Chemical group 0.000 claims 43
- 239000000203 mixture Substances 0.000 claims 37
- 150000002431 hydrogen Chemical class 0.000 claims 36
- 125000003118 aryl group Chemical group 0.000 claims 28
- 238000000034 method Methods 0.000 claims 24
- 125000000623 heterocyclic group Chemical group 0.000 claims 23
- 125000003545 alkoxy group Chemical group 0.000 claims 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- -1 lower alkyl-OX Chemical group 0.000 claims 14
- 229910052760 oxygen Inorganic materials 0.000 claims 14
- 239000001301 oxygen Substances 0.000 claims 14
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 102000008299 Nitric Oxide Synthase Human genes 0.000 claims 10
- 108010021487 Nitric Oxide Synthase Proteins 0.000 claims 10
- 238000004519 manufacturing process Methods 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 239000000758 substrate Substances 0.000 claims 10
- 208000035143 Bacterial infection Diseases 0.000 claims 9
- 208000025865 Ulcer Diseases 0.000 claims 9
- 208000022362 bacterial infectious disease Diseases 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 9
- 229940124597 therapeutic agent Drugs 0.000 claims 9
- 231100000397 ulcer Toxicity 0.000 claims 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims 8
- 229940037467 helicobacter pylori Drugs 0.000 claims 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 7
- 125000004414 alkyl thio group Chemical group 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 208000036142 Viral infection Diseases 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 210000003038 endothelium Anatomy 0.000 claims 6
- 230000035876 healing Effects 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 229920001184 polypeptide Polymers 0.000 claims 6
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- 230000009385 viral infection Effects 0.000 claims 6
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims 5
- 241000590002 Helicobacter pylori Species 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 5
- 125000001931 aliphatic group Chemical group 0.000 claims 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 5
- 229940069428 antacid Drugs 0.000 claims 5
- 239000003159 antacid agent Substances 0.000 claims 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 239000011593 sulfur Substances 0.000 claims 5
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 239000004215 Carbon black (E152) Substances 0.000 claims 4
- 102000010907 Cyclooxygenase 2 Human genes 0.000 claims 4
- 108010037462 Cyclooxygenase 2 Proteins 0.000 claims 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 4
- 230000003110 anti-inflammatory effect Effects 0.000 claims 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 4
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 4
- 239000000066 endothelium dependent relaxing factor Substances 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims 4
- 239000003112 inhibitor Substances 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 230000003637 steroidlike Effects 0.000 claims 4
- 208000016557 Acute basophilic leukemia Diseases 0.000 claims 3
- 241000701242 Adenoviridae Species 0.000 claims 3
- 241000712892 Arenaviridae Species 0.000 claims 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims 3
- 206010010774 Constipation Diseases 0.000 claims 3
- 241000711573 Coronaviridae Species 0.000 claims 3
- 208000011231 Crohn disease Diseases 0.000 claims 3
- 241000701022 Cytomegalovirus Species 0.000 claims 3
- 208000007882 Gastritis Diseases 0.000 claims 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 3
- 206010059024 Gastrointestinal toxicity Diseases 0.000 claims 3
- 208000007514 Herpes zoster Diseases 0.000 claims 3
- 241000700586 Herpesviridae Species 0.000 claims 3
- 241000701027 Human herpesvirus 6 Species 0.000 claims 3
- 206010020601 Hyperchlorhydria Diseases 0.000 claims 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 3
- QUOGESRFPZDMMT-UHFFFAOYSA-N L-Homoarginine Natural products OC(=O)C(N)CCCCNC(N)=N QUOGESRFPZDMMT-UHFFFAOYSA-N 0.000 claims 3
- QUOGESRFPZDMMT-YFKPBYRVSA-N L-homoarginine Chemical compound OC(=O)[C@@H](N)CCCCNC(N)=N QUOGESRFPZDMMT-YFKPBYRVSA-N 0.000 claims 3
- FQWRAVYMZULPNK-UHFFFAOYSA-N N(5)-[(Z)-amino(hydroxyimino)methyl]ornithine Chemical compound OC(=O)C(N)CCCNC(N)=NO FQWRAVYMZULPNK-UHFFFAOYSA-N 0.000 claims 3
- 241000712464 Orthomyxoviridae Species 0.000 claims 3
- 241000711504 Paramyxoviridae Species 0.000 claims 3
- 208000008469 Peptic Ulcer Diseases 0.000 claims 3
- 241000150350 Peribunyaviridae Species 0.000 claims 3
- 241000709664 Picornaviridae Species 0.000 claims 3
- 241000712907 Retroviridae Species 0.000 claims 3
- 241000711931 Rhabdoviridae Species 0.000 claims 3
- 206010051497 Rhinotracheitis Diseases 0.000 claims 3
- 241000700584 Simplexvirus Species 0.000 claims 3
- 206010042220 Stress ulcer Diseases 0.000 claims 3
- 201000008736 Systemic mastocytosis Diseases 0.000 claims 3
- 241000710924 Togaviridae Species 0.000 claims 3
- 206010061577 Ulcer haemorrhage Diseases 0.000 claims 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 3
- 201000008629 Zollinger-Ellison syndrome Diseases 0.000 claims 3
- 108700010877 adenoviridae proteins Proteins 0.000 claims 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims 3
- 230000003872 anastomosis Effects 0.000 claims 3
- 230000001458 anti-acid effect Effects 0.000 claims 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 3
- 150000001767 cationic compounds Chemical class 0.000 claims 3
- 229940111134 coxibs Drugs 0.000 claims 3
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims 3
- KWDSFGYQALRPMG-UHFFFAOYSA-N delta-N-Hydroxy-L-orginin Natural products OC(=O)C(N)CCCN(O)C(N)=N KWDSFGYQALRPMG-UHFFFAOYSA-N 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 208000000718 duodenal ulcer Diseases 0.000 claims 3
- 201000006549 dyspepsia Diseases 0.000 claims 3
- CHNUOJQWGUIOLD-NFZZJPOKSA-N epalrestat Chemical compound C=1C=CC=CC=1\C=C(/C)\C=C1/SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-NFZZJPOKSA-N 0.000 claims 3
- 230000002496 gastric effect Effects 0.000 claims 3
- 201000000052 gastrinoma Diseases 0.000 claims 3
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims 3
- 231100000414 gastrointestinal toxicity Toxicity 0.000 claims 3
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 3
- 230000002178 gastroprotective effect Effects 0.000 claims 3
- 229910001411 inorganic cation Inorganic materials 0.000 claims 3
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 3
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 3
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 3
- 208000011906 peptic ulcer disease Diseases 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 230000001737 promoting effect Effects 0.000 claims 3
- 229940126409 proton pump inhibitor Drugs 0.000 claims 3
- 239000000612 proton pump inhibitor Substances 0.000 claims 3
- 208000009305 pseudorabies Diseases 0.000 claims 3
- 208000011580 syndromic disease Diseases 0.000 claims 3
- ICRHORQIUXBEPA-UHFFFAOYSA-N thionitrous acid Chemical group SN=O ICRHORQIUXBEPA-UHFFFAOYSA-N 0.000 claims 3
- MXBVNILGVJVVMH-UHFFFAOYSA-N 1,7-naphthyridine Chemical compound C1=NC=CC2=CC=CN=C21 MXBVNILGVJVVMH-UHFFFAOYSA-N 0.000 claims 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 2
- JCZAVVUIFWZMQI-UHFFFAOYSA-N 1h-thieno[2,3-d]imidazole Chemical compound N1C=NC2=C1C=CS2 JCZAVVUIFWZMQI-UHFFFAOYSA-N 0.000 claims 2
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 claims 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims 2
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims 2
- 229930064664 L-arginine Natural products 0.000 claims 2
- 235000014852 L-arginine Nutrition 0.000 claims 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 2
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims 2
- 229960001138 acetylsalicylic acid Drugs 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004171 alkoxy aryl group Chemical group 0.000 claims 2
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims 2
- 125000005431 alkyl carboxamide group Chemical group 0.000 claims 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 2
- 125000005001 aminoaryl group Chemical group 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 230000000845 anti-microbial effect Effects 0.000 claims 2
- 125000001769 aryl amino group Chemical group 0.000 claims 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 2
- 125000005110 aryl thio group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 229910052797 bismuth Inorganic materials 0.000 claims 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims 2
- 229960001259 diclofenac Drugs 0.000 claims 2
- 208000010643 digestive system disease Diseases 0.000 claims 2
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 229960001680 ibuprofen Drugs 0.000 claims 2
- 229960000905 indomethacin Drugs 0.000 claims 2
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims 2
- 229960000991 ketoprofen Drugs 0.000 claims 2
- LKWFWCBKOFKSKI-UHFFFAOYSA-N n-sulfinylpyridine-3-carboxamide Chemical compound O=S=NC(=O)C1=CC=CN=C1 LKWFWCBKOFKSKI-UHFFFAOYSA-N 0.000 claims 2
- 229960002009 naproxen Drugs 0.000 claims 2
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 150000002892 organic cations Chemical class 0.000 claims 2
- 229960005489 paracetamol Drugs 0.000 claims 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 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 claims 1
- 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 claims 1
- QWPCKAAAWDCDCW-VKHMYHEASA-N (2s)-2-amino-4-nitrososulfanylbutanoic acid Chemical compound OC(=O)[C@@H](N)CCSN=O QWPCKAAAWDCDCW-VKHMYHEASA-N 0.000 claims 1
- YFJPZUQXBSAIKG-UHFFFAOYSA-N (4-amino-2h-quinolin-3-ylidene)methanone Chemical compound C1=CC=CC2=NCC(=C=O)C(N)=C21 YFJPZUQXBSAIKG-UHFFFAOYSA-N 0.000 claims 1
- GDIGSOKSULHYID-UHFFFAOYSA-N 1-[4-(2-aminophenyl)sulfanyl-8-methoxyquinolin-3-yl]butan-1-one Chemical compound CCCC(=O)C1=CN=C2C(OC)=CC=CC2=C1SC1=CC=CC=C1N GDIGSOKSULHYID-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 claims 1
- JVIHSTYYPRUSFG-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfinylmethyl)-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1CS(=O)C1=NC2=CC=CC=C2N1 JVIHSTYYPRUSFG-UHFFFAOYSA-N 0.000 claims 1
- PYKJFEPAUKAXNN-UHFFFAOYSA-N 2-(2-methyl-8-phenylmethoxy-3-imidazo[1,2-a]pyridinyl)acetonitrile Chemical compound C=1C=CN2C(CC#N)=C(C)N=C2C=1OCC1=CC=CC=C1 PYKJFEPAUKAXNN-UHFFFAOYSA-N 0.000 claims 1
- HBDKFZNDMVLSHM-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfinyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1S(=O)CC1=CC=CC=N1 HBDKFZNDMVLSHM-UHFFFAOYSA-N 0.000 claims 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims 1
- PAWVQNQQYYLBNN-UHFFFAOYSA-N 2-[4-(1h-indol-3-yl)-5-methyl-1,3-thiazol-2-yl]guanidine Chemical compound S1C(N=C(N)N)=NC(C=2C3=CC=CC=C3NC=2)=C1C PAWVQNQQYYLBNN-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- RZFLMMQTBGBSSE-UHFFFAOYSA-N 2-[[5-(1H-pyrrol-2-yl)pyridin-2-yl]methylsulfinyl]-1H-benzimidazole Chemical compound N1C(=CC=C1)C=1C=CC(=NC=1)CS(=O)C=1NC2=C(N=1)C=CC=C2 RZFLMMQTBGBSSE-UHFFFAOYSA-N 0.000 claims 1
- YNFBMDWHEHETJW-UHFFFAOYSA-N 2-pyridin-2-yl-1h-benzimidazole Chemical compound N1=CC=CC=C1C1=NC2=CC=CC=C2N1 YNFBMDWHEHETJW-UHFFFAOYSA-N 0.000 claims 1
- YZVXCSZASWLVLC-UHFFFAOYSA-N 2-sulfinyl-3h-pyridine-3-carboxamide Chemical compound NC(=O)C1C=CC=NC1=S=O YZVXCSZASWLVLC-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 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 claims 1
- 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 claims 1
- 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 claims 1
- 229940080328 Arginase inhibitor Drugs 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- MBHLHUJHLZNWCJ-UHFFFAOYSA-N C1CC2=CC=CC=C2NC1C1=NC=CC=N1 Chemical compound C1CC2=CC=CC=C2NC1C1=NC=CC=N1 MBHLHUJHLZNWCJ-UHFFFAOYSA-N 0.000 claims 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims 1
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 claims 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims 1
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 claims 1
- 108091034117 Oligonucleotide Proteins 0.000 claims 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 108010001742 S-Nitrosoglutathione Proteins 0.000 claims 1
- XOWVFANEOZMPKG-REOHCLBHSA-N S-nitroso-L-cysteine Chemical compound OC(=O)[C@@H](N)CSN=O XOWVFANEOZMPKG-REOHCLBHSA-N 0.000 claims 1
- UOHAKHBEJRPHQZ-VKHMYHEASA-N S-nitroso-L-cysteinylglycine Chemical compound O=NSC[C@H](N)C(=O)NCC(O)=O UOHAKHBEJRPHQZ-VKHMYHEASA-N 0.000 claims 1
- 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 claims 1
- HYHSBSXUHZOYLX-WDSKDSINSA-N S-nitrosoglutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CSN=O)C(=O)NCC(O)=O HYHSBSXUHZOYLX-WDSKDSINSA-N 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000000747 amidyl group Chemical group [H][N-]* 0.000 claims 1
- 235000001014 amino acid Nutrition 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims 1
- 150000001556 benzimidazoles Chemical class 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 238000003763 carbonization Methods 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 125000005518 carboxamido group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 235000013477 citrulline Nutrition 0.000 claims 1
- 229960002173 citrulline Drugs 0.000 claims 1
- 125000004986 diarylamino group Chemical group 0.000 claims 1
- 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 claims 1
- 229960004770 esomeprazole Drugs 0.000 claims 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 1
- 229960002743 glutamine Drugs 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 1
- 150000007857 hydrazones Chemical class 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 229960003174 lansoprazole Drugs 0.000 claims 1
- 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 claims 1
- 229960003646 lysine Drugs 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 claims 1
- 229960000381 omeprazole Drugs 0.000 claims 1
- 229960003104 ornithine Drugs 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 229960005019 pantoprazole Drugs 0.000 claims 1
- YIBBMDDEXKBIAM-UHFFFAOYSA-M potassium;pentoxymethanedithioate Chemical compound [K+].CCCCCOC([S-])=S YIBBMDDEXKBIAM-UHFFFAOYSA-M 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- 102000004196 processed proteins & peptides Human genes 0.000 claims 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
- 229960004157 rabeprazole Drugs 0.000 claims 1
- YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 claims 1
- 230000002040 relaxant effect Effects 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- IPAJARTUAXFVLF-UHFFFAOYSA-N sodium;9-(1h-benzimidazol-2-ylsulfinyl)-4-methoxy-2,5,6,7,8,9-hexahydrocyclohepta[b]pyridin-1-ide Chemical compound [Na+].COC1=CC[N-]C2=C1CCCCC2S(=O)C1=NC2=CC=CC=C2N1 IPAJARTUAXFVLF-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- 150000003459 sulfonic acid esters Chemical class 0.000 claims 1
- 229950008375 tenatoprazole Drugs 0.000 claims 1
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 claims 1
- 229940125670 thienopyridine Drugs 0.000 claims 1
- 239000002175 thienopyridine Substances 0.000 claims 1
- 229950011585 timoprazole Drugs 0.000 claims 1
- 0 CC(C)(*)CC[n]1c(nccc2)c2nc1* Chemical compound CC(C)(*)CC[n]1c(nccc2)c2nc1* 0.000 description 1
- WGRCBDNOOOBSRQ-UHFFFAOYSA-N CCc1c(CCN(C)C)nc2[n]1cccc2 Chemical compound CCc1c(CCN(C)C)nc2[n]1cccc2 WGRCBDNOOOBSRQ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39971502P | 2002-08-01 | 2002-08-01 | |
| PCT/US2003/023963 WO2004012659A2 (en) | 2002-08-01 | 2003-08-01 | Nitrosated proton pump inhibitors, compositions and methods of use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005539013A JP2005539013A (ja) | 2005-12-22 |
| JP2005539013A5 true JP2005539013A5 (enExample) | 2006-09-14 |
| JP4634144B2 JP4634144B2 (ja) | 2011-02-16 |
Family
ID=31495759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004526261A Expired - Fee Related JP4634144B2 (ja) | 2002-08-01 | 2003-08-01 | ニトロソ化プロトンポンプ阻害剤、組成物および使用方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7211590B2 (enExample) |
| EP (1) | EP1534278A4 (enExample) |
| JP (1) | JP4634144B2 (enExample) |
| AU (1) | AU2003254282A1 (enExample) |
| CA (1) | CA2493618A1 (enExample) |
| WO (1) | WO2004012659A2 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6345481B1 (en) | 1997-11-25 | 2002-02-12 | Premark Rwp Holdings, Inc. | Article with interlocking edges and covering product prepared therefrom |
| US6852739B1 (en) * | 1999-02-26 | 2005-02-08 | Nitromed Inc. | Methods using proton pump inhibitors and nitric oxide donors |
| TW200613301A (en) * | 2004-06-15 | 2006-05-01 | Altana Pharma Ag | Novel amino-halogen-imidazopyridines |
| TW200616604A (en) | 2004-08-26 | 2006-06-01 | Nicholas Piramal India Ltd | Nitric oxide releasing prodrugs containing bio-cleavable linker |
| ES2329930T3 (es) | 2005-02-11 | 2009-12-02 | Nolabs Ab | Dispositivo, metodo y uso para el tratamiento de la neuropatia con oxido nitrico. |
| EP1846009A2 (en) * | 2005-02-11 | 2007-10-24 | NOLabs AB | Improved device for application of medicaments, manufacturing method therefor, and method of treatment |
| EP1690554A1 (en) * | 2005-02-11 | 2006-08-16 | NOLabs AB | Device for treatment of infections, including dermatophytosis and onychomycosis |
| EP1871433B1 (en) | 2005-03-24 | 2009-04-22 | NOLabs AB | Cosmetic treatment with nitric oxide, device for performing said treatment and manufacturing method therefor |
| TW200745080A (en) * | 2005-09-16 | 2007-12-16 | Takeda Pharmaceuticals Co | Polymorphs of tartrate salt of 2-[2-(3-(R)-amino-piperidin-1-yl)-5-fluoro-6-oxo-6H-pyrimidin-1-ylmethyl]-benzonitrile and methods of use therefor |
| US7994205B2 (en) * | 2006-03-31 | 2011-08-09 | Takeda Pharmaceutical Company Limited | Aryl-or heteroaryl-sulfonyl compounds as acid secretion inhibitors |
| CN101415414B (zh) * | 2006-04-04 | 2013-06-12 | 雀巢产品技术援助有限公司 | 瓜氨酸在制备治疗矫正脓毒症患者中精氨酸缺乏的药物中的用途 |
| MX2008012723A (es) * | 2006-04-04 | 2008-10-14 | Nestec Sa | Tratamientos que usan citrulina. |
| US20090156642A1 (en) * | 2007-09-28 | 2009-06-18 | Takeda Pharmaceutical Company Limited | 5-Membered heterocyclic compound |
| EP2048129A1 (en) * | 2007-10-12 | 2009-04-15 | Lonza Ag | Method for the preparation of organic nitrates |
| EP2412713B1 (en) | 2009-03-26 | 2016-11-30 | Takeda Pharmaceutical Company Limited | Pyrazole compound |
| DE102009037555A1 (de) * | 2009-08-13 | 2011-03-03 | Synovo Gmbh | Ein neuartiges, schonendes Verfahren zur direkten Nitrierung von Hydroxyl-, Thiol- und Aminogruppen in organischen Molekülen mittels in situ generiertem Kohlensäuredinitrat |
| 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 |
| ES2804263T3 (es) | 2011-07-05 | 2021-02-05 | Novan Inc | Composiciones tópicas |
| US9855211B2 (en) | 2013-02-28 | 2018-01-02 | Novan, Inc. | Topical compositions and methods of using the same |
| WO2016022170A1 (en) | 2014-08-08 | 2016-02-11 | Novan, Inc. | Topical emulsions |
| AU2014305778B2 (en) | 2013-08-08 | 2019-11-21 | Ligand Pharmaceuticals Incorporated | Topical compositions and methods of using the same |
| JP7090549B2 (ja) | 2016-03-02 | 2022-06-24 | ノヴァン，インコーポレイテッド | 炎症のための治療用組成物およびその治療方法 |
| EP3442502A4 (en) | 2016-04-13 | 2019-11-06 | Novan, Inc. | COMPOSITIONS, SYSTEMS, KITS AND METHODS FOR TREATING INFECTIONS |
| IT202200001022A1 (it) * | 2022-01-21 | 2023-07-21 | Exo Lab Italia | Composti farmaceutici ibridi ottenuti mediante coniugazione di un inibitore delle pompe protoniche e un inibitore delle anidrasi carboniche |
Family Cites Families (80)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE416649B (sv) * | 1974-05-16 | 1981-01-26 | Haessle Ab | Forfarande for framstellning av foreningar som paverkar magsyrasekretionen |
| SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
| ZA81219B (en) | 1980-01-23 | 1982-01-27 | Schering Corp | Imidazo (1,2-a) pyridines ,process for their preparation and pharmaceutical compositions containing them |
| US4359465A (en) | 1980-07-28 | 1982-11-16 | The Upjohn Company | Methods for treating gastrointestinal inflammation |
| ZW4585A1 (en) * | 1984-04-19 | 1985-11-20 | Hoffmann La Roche | Imidazole derivatives |
| IL75400A (en) * | 1984-06-16 | 1988-10-31 | Byk Gulden Lomberg Chem Fab | Dialkoxypyridine methyl(sulfinyl or sulfonyl)benzimidazoles,processes for the preparation thereof and pharmaceutical compositions containing the same |
| JPS6150978A (ja) * | 1984-08-16 | 1986-03-13 | Takeda Chem Ind Ltd | ピリジン誘導体およびその製造法 |
| KR890000387B1 (ko) * | 1984-09-24 | 1989-03-16 | 디 엎존 캄파니 | 2-(피리딜알켄술 피닐)벤즈 이미드아졸류의 n-치환 유도체의 제조방법 |
| GB8610607D0 (en) | 1986-04-30 | 1986-06-04 | Smith Kline French Lab | Chemical compounds |
| SE8505112D0 (sv) | 1985-10-29 | 1985-10-29 | Haessle Ab | Novel pharmacological compounds |
| EP0234485B1 (de) * | 1986-02-20 | 1992-04-01 | Hoechst Aktiengesellschaft | Substituierte Thienoimidazol-Derivate, Verfahren zu ihrer Herstellung, sie enthaltende pharmazeutische Zubereitungen und ihre Verwendung als Magensäuresekretionshemmer |
| JPH0643426B2 (ja) * | 1986-07-25 | 1994-06-08 | 東京田辺製薬株式会社 | イミダゾ〔４，５−ｂ〕ピリジン誘導体、その製造法及びそれを含有する抗潰瘍剤 |
| GB8621425D0 (en) * | 1986-09-05 | 1986-10-15 | Smith Kline French Lab | Compounds |
| CA1256109A (en) * | 1986-09-10 | 1989-06-20 | Franz Rovenszky | Process for the preparation of derivatives of 4, 5-dihydrooxazoles |
| FI90544C (fi) * | 1986-11-13 | 1994-02-25 | Eisai Co Ltd | Menetelmä lääkeaineina käyttökelpoisten 2-pyridin-2-yyli-metyylitio- ja sulfinyyli-1H-bensimidatsolijohdannaisten valmistamiseksi |
| DE3639926A1 (de) * | 1986-11-22 | 1988-06-01 | Hoechst Ag | Substituierte thienoimidazoltoluidin-derivate, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung als magensaeuresekretionshemmer |
| ATE81011T1 (de) * | 1987-03-09 | 1992-10-15 | Procter & Gamble | Zusammensetzungen und ihre verwendung zur behandlung von magen-darmstoerungen. |
| US4839365A (en) * | 1987-05-19 | 1989-06-13 | Shinogi & Co., Ltd. | Thienopyridine derivatives useful in treating gastric ulcers |
| DE3723327A1 (de) * | 1987-07-15 | 1989-02-02 | Hoechst Ag | Substituierte thienoimidazol-derivate, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung als magensaeuresekretionshemmer, magenschutzmittel sowie als medikament gegen intestinale entzuendungen |
| ES2060672T3 (es) * | 1987-11-13 | 1994-12-01 | Hoechst Ag | Derivados de tienoimidazol sustituidos, procedimiento para su preparacion, preparados farmaceuticos que los contienen y su utilizacion como inhibidores de la secrecion de acidos gastricos. |
| GB8804444D0 (en) | 1988-02-25 | 1988-03-23 | Smithkline Beckman Intercredit | Compounds |
| ES2057338T3 (es) * | 1989-11-29 | 1994-10-16 | Toa Eiyo Ltd | Derivados de cicloheptenopiridina, procedimiento para su preparacion y agentes antiulcerosos que los contienen. |
| HUT67609A (en) | 1991-01-29 | 1995-04-28 | Smithkline Beecham Intercredit | Salts of a 4-amino-3-acyl-quinoline derivative, their preparation and pharmaceutical compositions comprising them |
| SE9100920D0 (sv) * | 1991-03-27 | 1991-03-27 | Astra Ab | New active compounds |
| US5380758A (en) * | 1991-03-29 | 1995-01-10 | Brigham And Women's Hospital | S-nitrosothiols as smooth muscle relaxants and therapeutic uses thereof |
| NZ244301A (en) * | 1991-09-20 | 1994-08-26 | Merck & Co Inc | Preparation of 2-pyridylmethylsulphinylbenzimidazole and pyridoimidazole derivatives from the corresponding sulphenyl compounds |
| TW276996B (enExample) * | 1992-04-24 | 1996-06-01 | Astra Ab | |
| US5504082A (en) * | 1992-06-01 | 1996-04-02 | Yoshitomi Pharmaceutical Industries, Ltd. | Pyridine compound and pharmaceutical compostions |
| KR0144833B1 (ko) * | 1992-12-28 | 1998-07-15 | 김태훈 | 신규의 퀴나졸린 유도체 및 그의 제조방법 |
| IL108520A (en) * | 1993-02-15 | 1997-09-30 | Byk Gulden Lomberg Chem Fab | 2, 3, 8-TRISUBSTITUTED IMIDAZO £1, 2-a| PYRIDINE DERIVATIVES, PROCESSES FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| SE9301830D0 (sv) * | 1993-05-28 | 1993-05-28 | Ab Astra | New compounds |
| EP0639644A1 (de) * | 1993-08-16 | 1995-02-22 | Ciba-Geigy Ag | Neue Makrolide und ihre Verwendung |
| US5374730A (en) * | 1993-11-04 | 1994-12-20 | Torcan Chemical Ltd. | Preparation of omeprazole and lansoprazole |
| KR0142815B1 (ko) * | 1994-12-02 | 1998-07-15 | 정도언 | 신규한 5-피롤릴-6-할로게노-2피리딜메틸설피닐벤즈이미다졸 유도체 |
| KR0179401B1 (ko) * | 1994-02-28 | 1999-03-20 | 송택선 | 신규한 5-피롤릴-2-피리딜메틸설피닐벤즈이미다졸 유도체 |
| SE9401197D0 (sv) | 1994-04-11 | 1994-04-11 | Astra Ab | Active compounds |
| WO1995029897A1 (en) * | 1994-04-29 | 1995-11-09 | G.D. Searle & Co. | METHOD OF USING (H+/K+) ATPase INHIBITORS AS ANTIVIRAL AGENTS |
| DE4420523A1 (de) | 1994-06-13 | 1995-12-14 | Cassella Ag | Verwendung von NO-freisetzenden Verbindungen zur Behandlung und Vorbeugung von systemischen Entzündungssyndromen |
| JP2896532B2 (ja) * | 1994-08-13 | 1999-05-31 | ユーハン コーポレーション | 新規なピリミジン誘導体およびその製造方法 |
| DE4432106A1 (de) * | 1994-09-09 | 1996-03-14 | Hoechst Ag | Mit Heterocyclen-N-Oxid-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum, sie enthaltendes Medikament sowie Zwischenprodukte zu ihrer Herstellung |
| DE4432101A1 (de) * | 1994-09-09 | 1996-03-14 | Hoechst Ag | Aminosäure-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| 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 |
| KR0169813B1 (ko) * | 1995-07-12 | 1999-01-15 | 김종인 | 4-아미노-3-아실나프티리딘 유도체 |
| SE9600070D0 (sv) * | 1996-01-08 | 1996-01-08 | Astra Ab | New oral pharmaceutical dosage forms |
| CN1154246A (zh) | 1996-01-09 | 1997-07-16 | 李宏 | 一种抗菌抗病毒药物的组方 |
| US5677302A (en) * | 1996-02-26 | 1997-10-14 | Apotex Inc. | Thiadiazole compounds useful as proton pump inhibitors |
| SE9600791L (sv) | 1996-02-27 | 1997-08-28 | Holdingbolaget Vid Goeteborgs | Metod för eradikering av Helicobacter pylori infektion |
| AU4845196A (en) | 1996-03-04 | 1997-09-22 | Dainippon Pharmaceutical Co. Ltd. | 2-sulfinylnicotinamide derivatives, intermediate thereof, process for producing 2-sulfinylnicotinamide derivatives, and medicinal composition containing the same as active ingredient |
| EP0900214B1 (en) * | 1996-05-04 | 2001-09-26 | Yuhan Corporation | Process for preparation of pyrimidine derivatives |
| WO1998018784A1 (en) | 1996-10-29 | 1998-05-07 | Yuhan Corporation | Process for preparation of pyrimidine derivatives |
| HUP9904073A3 (en) | 1996-11-22 | 2000-04-28 | Procter & Gamble | Compositions for the treatment of gastrointestinal disorders containing bismuth and nsaid |
| IN188411B (enExample) | 1997-03-27 | 2002-09-21 | Yuhan Corp | |
| AU6551198A (en) | 1997-05-30 | 1998-12-30 | Dr. Reddy's Research Foundation | Novel benzimidazole derivatives as antiulcer agents, process for their preparation and pharmaceutical compositions containing them |
| US6156771A (en) * | 1997-08-28 | 2000-12-05 | Rubin; Walter | Method for alleviation of lower gastrointestinal disorders in a human patient |
| JPH11171791A (ja) | 1997-10-07 | 1999-06-29 | Kanegafuchi Chem Ind Co Ltd | 蛋白質分解酵素を含むヘリコバクター属細菌の除菌剤及び／又は殺菌剤、並びに該細菌に起因する疾患の治療剤及び／又は発症抑制剤 |
| US6174548B1 (en) | 1998-08-28 | 2001-01-16 | Andrx Pharmaceuticals, Inc. | Omeprazole formulation |
| IT1298338B1 (it) | 1998-03-05 | 1999-12-20 | Nicox Sa | Composizioni farmaceutiche per l'ulcera |
| IT1299198B1 (it) | 1998-03-05 | 2000-02-29 | Nicox Sa | Sali nitrati di farmaci antiulcera |
| AU771061B2 (en) | 1999-02-23 | 2004-03-11 | Merck Sharp & Dohme Corp. | Pharmaceutical composition containing proton pump inhibitors |
| US6852739B1 (en) * | 1999-02-26 | 2005-02-08 | Nitromed Inc. | Methods using proton pump inhibitors and nitric oxide donors |
| EP1154771A4 (en) * | 1999-02-26 | 2005-04-20 | Nitromed Inc | INHIBITORS OF THE PROTON NITROSIS AND NITROSYL PUMP, COMPOSITIONS AND METHODS OF USE |
| IT1311923B1 (it) | 1999-04-13 | 2002-03-20 | Nicox Sa | Composti farmaceutici. |
| IT1311924B1 (it) | 1999-04-13 | 2002-03-20 | Nicox Sa | Composti farmaceutici. |
| GB9911017D0 (en) | 1999-05-13 | 1999-07-14 | Zeneca Ltd | Pharmaceutical compositions |
| TWI243672B (en) | 1999-06-01 | 2005-11-21 | Astrazeneca Ab | New use of compounds as antibacterial agents |
| IT1314184B1 (it) | 1999-08-12 | 2002-12-06 | Nicox Sa | Composizioni farmaceutiche per la terapia di condizioni di stressossidativo |
| WO2001044257A1 (en) | 1999-12-17 | 2001-06-21 | Ariad Pharmaceuticals, Inc. | Proton pump inhibitors |
| SE0000773D0 (sv) | 2000-03-08 | 2000-03-08 | Astrazeneca Ab | New formulation |
| GB0011098D0 (en) | 2000-05-08 | 2000-06-28 | Black James Foundation | Pharmaceutical compositions comprising protpn pump inhibitors and gastrin/cholecystokinin receptor ligands |
| SE0002476D0 (sv) * | 2000-06-30 | 2000-06-30 | Astrazeneca Ab | New compounds |
| IT1320176B1 (it) | 2000-12-22 | 2003-11-26 | Nicox Sa | Dispersioni solide di principi attivi nitrati. |
| US20040082605A1 (en) * | 2001-03-08 | 2004-04-29 | Arne Eek | Use |
| SE0102993D0 (sv) | 2001-09-07 | 2001-09-07 | Astrazeneca Ab | New self emulsifying drug delivery system |
| CA2458628A1 (en) | 2001-09-12 | 2003-03-20 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Use of substituted aminomethyl chromans in the treatment of movement disorders |
| WO2003053221A2 (en) | 2001-12-19 | 2003-07-03 | Eisai Co. Ltd | Methods using proton pump inhibitors |
| SE0200895D0 (sv) | 2002-03-22 | 2002-03-22 | Astrazeneca Ab | New pharmaceutical composition |
| AU2003241464A1 (en) | 2002-05-17 | 2003-12-02 | Eisai Co., Ltd. | Compositions and methods using proton pump inhibitors |
| PT1556371E (pt) * | 2002-07-19 | 2006-09-29 | Winston Pharmateuticals Llc | Derivados de benzimidazole e sua utilizacao como pro-farmacos de inibadores da bomba de protoes. |
-
2003
- 2003-08-01 WO PCT/US2003/023963 patent/WO2004012659A2/en not_active Ceased
- 2003-08-01 US US10/631,782 patent/US7211590B2/en not_active Expired - Fee Related
- 2003-08-01 EP EP03767016A patent/EP1534278A4/en not_active Withdrawn
- 2003-08-01 CA CA002493618A patent/CA2493618A1/en not_active Abandoned
- 2003-08-01 JP JP2004526261A patent/JP4634144B2/ja not_active Expired - Fee Related
- 2003-08-01 AU AU2003254282A patent/AU2003254282A1/en not_active Abandoned
-
2007
- 2007-03-22 US US11/689,568 patent/US20070179150A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2005539013A5 (enExample) | ||
| DK2588465T3 (en) | SGC stimulators | |
| ES2896960T3 (es) | Agentes alquilantes del ADN para su uso en el tratamiento del cáncer | |
| ES2652287T3 (es) | 1H-pirazol [3,4-b] piridinas y usos terapéuticos de las mismas | |
| JP6290203B2 (ja) | ヘッジホッグ経路阻害剤としてのｎ−（３−ヘテロアリールアリール）−４−アリールアリールカルボキサミド及び類似体並びにそれらの使用 | |
| ES2383766T3 (es) | Remedio o preventivo para úlcera digestiva | |
| KR100472126B1 (ko) | 양성자 펌프 억제제의 프로드러그 | |
| RU2020112759A (ru) | Гетероциклические соединения в качестве ингибиторов PAD | |
| NZ590784A (en) | Pyrazolopyridine kinase inhibitors | |
| ZA200100560B (en) | Prodrugs of proton pump inhibitors. | |
| CA2362930A1 (en) | Nitrosated and nitrosylated proton pump inhibitors, compositions and methods of use | |
| JP4634144B2 (ja) | ニトロソ化プロトンポンプ阻害剤、組成物および使用方法 | |
| BRPI0719195B1 (pt) | inibidores de quinase, seus usos, e composição farmacêutica | |
| JP2002537336A5 (enExample) | ||
| CA2422354A1 (en) | Pyrazole compounds useful as protein kinase inhibitors | |
| RU2009131454A (ru) | Способы предупреждения или уменьшения числа обострений подагры с применением ингибиторов ксантиноксидоредуктазы и противовоспалительных средств | |
| JP2012506848A5 (enExample) | ||
| WO2010035745A1 (ja) | ヘテロ環ビアリール誘導体及びそれらを有効成分とするｐｄｅ阻害剤 | |
| RU2139286C1 (ru) | Замещенные арилалкилтиоалкилтиопиридины для борьбы с бактериями helicobacter | |
| ES2468221T3 (es) | Derivados de bencimidazol y composiciones farmacéuticas del mismo | |
| JP6231195B2 (ja) | スルホニルインドール誘導体およびその製造方法 | |
| ES2372600T3 (es) | Derivado de pirazolonaftiridina. | |
| RU2006141255A (ru) | Соединение имидазопиридина | |
| ES2300796T3 (es) | Nuevo compuesto de imidazopiridina ii con efecto terapeutico. | |
| KR102161674B1 (ko) | 이사틴 유도체 및 이의 제조방법 |