JP2005539013A5 - - Google Patents
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- 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
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- 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
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| AU2277201A (en) | 1999-12-17 | 2001-06-25 | Ariad Pharmaceuticals, Inc. | Novel purines |
| 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. |
| CZ20032398A3 (cs) | 2001-03-08 | 2004-02-18 | Astrazeneca Ab | Nové použití derivátů 6-karboxamidoimidazo [1,2-a] pyridinu |
| SE0102993D0 (sv) | 2001-09-07 | 2001-09-07 | Astrazeneca Ab | New self emulsifying drug delivery system |
| WO2003022269A1 (en) | 2001-09-12 | 2003-03-20 | Merck Patent Gmbh | Novel use of substituted aminomethyl chromans for the treatment of movement disorders and of adverse effects induced by drugs administered to treat extrapyramidal movement disorders |
| AU2002366796A1 (en) | 2001-12-19 | 2003-07-09 | Eisai Co. Ltd | Methods using proton pump inhibitors |
| SE0200895D0 (sv) | 2002-03-22 | 2002-03-22 | Astrazeneca Ab | New pharmaceutical composition |
| WO2003097011A1 (en) | 2002-05-17 | 2003-11-27 | Eisai Co., Ltd. | Compositions and methods using proton pump inhibitors |
| KR100788778B1 (ko) | 2002-07-19 | 2007-12-27 | 윈스턴 파마슈티컬즈, 엘엘씨 | 벤즈이미다졸 유도체 및 이들의 프로톤 펌프 억제제의프로드럭으로서의 이용 |
-
2003
- 2003-08-01 AU AU2003254282A patent/AU2003254282A1/en not_active Abandoned
- 2003-08-01 JP JP2004526261A patent/JP4634144B2/ja not_active Expired - Fee Related
- 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
-
2007
- 2007-03-22 US US11/689,568 patent/US20070179150A1/en not_active Abandoned
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