JP2006516592A5 - - Google Patents
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- Publication number
- JP2006516592A5 JP2006516592A5 JP2006501731A JP2006501731A JP2006516592A5 JP 2006516592 A5 JP2006516592 A5 JP 2006516592A5 JP 2006501731 A JP2006501731 A JP 2006501731A JP 2006501731 A JP2006501731 A JP 2006501731A JP 2006516592 A5 JP2006516592 A5 JP 2006516592A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- group
- acetamide
- pyrrol
- benzoyl
- 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
- -1 benzenesulfonyloxy Chemical group 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 4
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 229910003827 NRaRb Inorganic materials 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical group CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- 206010034277 Pemphigoid Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
- IDIDJDIHTAOVLG-VKHMYHEASA-N S-methylcysteine Chemical compound CSC[C@H](N)C(O)=O IDIDJDIHTAOVLG-VKHMYHEASA-N 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 229940024606 amino acid Drugs 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 208000000594 bullous pemphigoid Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000004761 fibrosis Effects 0.000 claims 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 2
- 125000001165 hydrophobic group Chemical group 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 230000010410 reperfusion Effects 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 claims 1
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- MDSMFFNGDIUDOF-UHFFFAOYSA-N 2-(1-benzoyl-2-chloropyrrol-3-yl)acetic acid Chemical compound ClC1=C(CC(=O)O)C=CN1C(=O)C1=CC=CC=C1 MDSMFFNGDIUDOF-UHFFFAOYSA-N 0.000 claims 1
- AZCOEIZFVQEQCU-UHFFFAOYSA-N 2-(1-benzoyl-2-methylindol-3-yl)acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CC=C2N1C(=O)C1=CC=CC=C1 AZCOEIZFVQEQCU-UHFFFAOYSA-N 0.000 claims 1
- XKYYONVQZFOHLX-UHFFFAOYSA-N 2-(1-benzoyl-2-methylpyrrol-3-yl)acetic acid Chemical compound CC1=C(CC(O)=O)C=CN1C(=O)C1=CC=CC=C1 XKYYONVQZFOHLX-UHFFFAOYSA-N 0.000 claims 1
- VYNWQRJLEFFYJW-UHFFFAOYSA-N 2-(2-chloro-3-propanoylphenyl)acetic acid Chemical compound CCC(=O)C1=CC=CC(CC(O)=O)=C1Cl VYNWQRJLEFFYJW-UHFFFAOYSA-N 0.000 claims 1
- IQCYKHUXUJYEQT-UHFFFAOYSA-N 2-(2-methyl-3-propan-2-ylphenyl)acetic acid Chemical compound CC(C)C1=CC=CC(CC(O)=O)=C1C IQCYKHUXUJYEQT-UHFFFAOYSA-N 0.000 claims 1
- OTSCNWKNPQLUII-UHFFFAOYSA-N 2-(3-benzoyl-2-methoxyphenyl)acetic acid Chemical compound COC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=CC=C1 OTSCNWKNPQLUII-UHFFFAOYSA-N 0.000 claims 1
- OGWHHEUWVCAJKC-UHFFFAOYSA-N 2-(3-benzoyl-2-methylphenyl)acetic acid Chemical compound CC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=CC=C1 OGWHHEUWVCAJKC-UHFFFAOYSA-N 0.000 claims 1
- QTPAUDWUWBSRLX-UHFFFAOYSA-N 2-(5-acetyl-1-methylpyrrol-2-yl)acetic acid Chemical compound CC(=O)C1=CC=C(CC(O)=O)N1C QTPAUDWUWBSRLX-UHFFFAOYSA-N 0.000 claims 1
- WVKPVCGHCFYVKZ-UHFFFAOYSA-N 2-(5-benzoyl-1-methylpyrrol-2-yl)acetic acid Chemical compound CN1C(CC(O)=O)=CC=C1C(=O)C1=CC=CC=C1 WVKPVCGHCFYVKZ-UHFFFAOYSA-N 0.000 claims 1
- QDAPWMKWLVMBBU-UHFFFAOYSA-N 2-[1-(4-chlorobenzoyl)-2-methylindol-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 QDAPWMKWLVMBBU-UHFFFAOYSA-N 0.000 claims 1
- FPVHGWJOLPNFOE-UHFFFAOYSA-N 2-[1-methyl-5-(2-methylpropanoyl)pyrrol-2-yl]acetic acid Chemical compound CC(C)C(=O)C1=CC=C(CC(O)=O)N1C FPVHGWJOLPNFOE-UHFFFAOYSA-N 0.000 claims 1
- NDJZTHKBZXIDHH-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethylsulfonyloxy)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=C(OS(=O)(=O)C(F)(F)F)C=C1Cl NDJZTHKBZXIDHH-UHFFFAOYSA-N 0.000 claims 1
- BXVGCNQIUDNXRC-UHFFFAOYSA-N 2-[2-methyl-4-(2-methylpropyl)phenyl]acetic acid Chemical compound CC(C)CC1=CC=C(CC(O)=O)C(C)=C1 BXVGCNQIUDNXRC-UHFFFAOYSA-N 0.000 claims 1
- DZGOOVJENNOITA-UHFFFAOYSA-N 2-[2-methyl-4-(trifluoromethylsulfonylamino)phenyl]acetic acid Chemical compound CC1=CC(NS(=O)(=O)C(F)(F)F)=CC=C1CC(O)=O DZGOOVJENNOITA-UHFFFAOYSA-N 0.000 claims 1
- ZNHYRLMPIUNEJW-UHFFFAOYSA-N 2-[4-(benzenesulfonamido)-2-methylphenyl]acetic acid Chemical compound C1=C(CC(O)=O)C(C)=CC(NS(=O)(=O)C=2C=CC=CC=2)=C1 ZNHYRLMPIUNEJW-UHFFFAOYSA-N 0.000 claims 1
- ZWUBGDPUVGOZMR-UHFFFAOYSA-N 2-[5-(4-chlorobenzoyl)-1-methylpyrrol-2-yl]acetic acid Chemical compound CN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C(Cl)C=C1 ZWUBGDPUVGOZMR-UHFFFAOYSA-N 0.000 claims 1
- MZDOZMBPEYIXBX-UHFFFAOYSA-N 2-[[2-(5-acetyl-1-methylpyrrol-2-yl)acetyl]amino]acetic acid Chemical compound CC(=O)C1=CC=C(CC(=O)NCC(O)=O)N1C MZDOZMBPEYIXBX-UHFFFAOYSA-N 0.000 claims 1
- PSNWQVRVRARAHU-UHFFFAOYSA-N 2-methyl-1-propan-2-ylpyrrole Chemical compound CC(C)N1C=CC=C1C PSNWQVRVRARAHU-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims 1
- JDZKKEZDNANCEJ-UHFFFAOYSA-N CC1=CC=C(C=C1)C(=O)C2=CC=C(N2C)N(C(=O)C)S(=O)(=O)C Chemical compound CC1=CC=C(C=C1)C(=O)C2=CC=C(N2C)N(C(=O)C)S(=O)(=O)C JDZKKEZDNANCEJ-UHFFFAOYSA-N 0.000 claims 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 102000004890 Interleukin-8 Human genes 0.000 claims 1
- 108090001007 Interleukin-8 Proteins 0.000 claims 1
- 150000007649 L alpha amino acids Chemical class 0.000 claims 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 1
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 claims 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 1
- XVPGPJRKVMVKJY-UHFFFAOYSA-N N-(3-benzoyl-2-methoxyphenyl)acetamide Chemical compound COc1c(NC(C)=O)cccc1C(=O)c1ccccc1 XVPGPJRKVMVKJY-UHFFFAOYSA-N 0.000 claims 1
- MLZOYRSGVAWKCO-UHFFFAOYSA-N N-(5-acetyl-1-methylpyrrol-2-yl)-N-methylsulfonylacetamide Chemical compound CC(=O)N(c1ccc(C(C)=O)n1C)S(C)(=O)=O MLZOYRSGVAWKCO-UHFFFAOYSA-N 0.000 claims 1
- NXWMZOOVXOBFIC-UHFFFAOYSA-N N-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetamide Chemical compound COc1ccc2n(C(=O)c3ccc(Cl)cc3)c(C)c(NC(C)=O)c2c1 NXWMZOOVXOBFIC-UHFFFAOYSA-N 0.000 claims 1
- LZZPWHRFUZKKBB-UHFFFAOYSA-N N-methylsulfonyl-N-[2-methyl-4-(trifluoromethylsulfonylamino)phenyl]acetamide Chemical compound CC(=O)N(c1ccc(NS(=O)(=O)C(F)(F)F)cc1C)S(C)(=O)=O LZZPWHRFUZKKBB-UHFFFAOYSA-N 0.000 claims 1
- IDIDJDIHTAOVLG-UHFFFAOYSA-N S-methyl-L-cysteine Natural products CSCC(N)C(O)=O IDIDJDIHTAOVLG-UHFFFAOYSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 1
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- 229960003767 alanine Drugs 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000001769 aryl amino group Chemical group 0.000 claims 1
- 229940000635 beta-alanine Drugs 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 239000007806 chemical reaction intermediate Substances 0.000 claims 1
- 230000035605 chemotaxis Effects 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims 1
- 229960002449 glycine Drugs 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229960000310 isoleucine Drugs 0.000 claims 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 1
- 229960003136 leucine Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- OIPKFSCAQQEJDF-UHFFFAOYSA-N n-(1-benzoyl-2-methylindol-3-yl)acetamide Chemical compound C12=CC=CC=C2C(NC(=O)C)=C(C)N1C(=O)C1=CC=CC=C1 OIPKFSCAQQEJDF-UHFFFAOYSA-N 0.000 claims 1
- AIKIPTMUDMVQJH-UHFFFAOYSA-N n-(3-benzoyl-2-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1C AIKIPTMUDMVQJH-UHFFFAOYSA-N 0.000 claims 1
- LRJZKWXVWFQBMV-UHFFFAOYSA-N n-(5-acetyl-1-methylpyrrol-2-yl)acetamide Chemical compound CC(=O)NC1=CC=C(C(C)=O)N1C LRJZKWXVWFQBMV-UHFFFAOYSA-N 0.000 claims 1
- CKCQCGCCIDMXIP-UHFFFAOYSA-N n-[1-(4-chlorobenzoyl)-2-methylindol-3-yl]acetamide Chemical compound C12=CC=CC=C2C(NC(=O)C)=C(C)N1C(=O)C1=CC=C(Cl)C=C1 CKCQCGCCIDMXIP-UHFFFAOYSA-N 0.000 claims 1
- GNFVGZYSNLZISU-UHFFFAOYSA-N n-[1-methyl-5-(2-methylpropanoyl)pyrrol-2-yl]acetamide Chemical compound CC(C)C(=O)C1=CC=C(NC(C)=O)N1C GNFVGZYSNLZISU-UHFFFAOYSA-N 0.000 claims 1
- IZTCNMANEXXNBG-UHFFFAOYSA-N n-[2-methyl-4-(2-methylpropyl)phenyl]-n-methylsulfonylacetamide Chemical compound CC(C)CC1=CC=C(N(C(C)=O)S(C)(=O)=O)C(C)=C1 IZTCNMANEXXNBG-UHFFFAOYSA-N 0.000 claims 1
- YGTZOCNQAGVWON-UHFFFAOYSA-N n-[2-methyl-4-(2-methylpropyl)phenyl]acetamide Chemical compound CC(C)CC1=CC=C(NC(C)=O)C(C)=C1 YGTZOCNQAGVWON-UHFFFAOYSA-N 0.000 claims 1
- WBASTPBNZXCEJH-UHFFFAOYSA-N n-[5-(4-chlorobenzoyl)-1-methylpyrrol-2-yl]acetamide Chemical compound CN1C(NC(=O)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 WBASTPBNZXCEJH-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 claims 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims 1
- 239000004474 valine Substances 0.000 claims 1
- 229960004295 valine Drugs 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03002716.3 | 2003-02-06 | ||
| EP03002716 | 2003-02-06 | ||
| PCT/EP2004/001021 WO2004069782A2 (en) | 2003-02-06 | 2004-02-04 | 2-aryl-acetic acids, their derivatives and pharmaceutical compositions containing them |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006516592A JP2006516592A (ja) | 2006-07-06 |
| JP2006516592A5 true JP2006516592A5 (https=) | 2007-03-22 |
| JP5208411B2 JP5208411B2 (ja) | 2013-06-12 |
Family
ID=32842696
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006501731A Expired - Fee Related JP5208411B2 (ja) | 2003-02-06 | 2004-02-04 | ２−アリール−酢酸、その誘導体、及びそれらを含有する医薬組成物 |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US7776909B2 (https=) |
| EP (1) | EP1590314B1 (https=) |
| JP (1) | JP5208411B2 (https=) |
| CN (1) | CN100562511C (https=) |
| AU (2) | AU2004210082B2 (https=) |
| CA (1) | CA2511582C (https=) |
| DK (1) | DK1590314T3 (https=) |
| ES (1) | ES2551929T3 (https=) |
| HU (1) | HUE026285T2 (https=) |
| NO (1) | NO334149B1 (https=) |
| PT (1) | PT1590314E (https=) |
| RU (1) | RU2356887C2 (https=) |
| SI (1) | SI1590314T1 (https=) |
| WO (1) | WO2004069782A2 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2477604A1 (en) | 2002-03-13 | 2003-09-25 | Signum Biosciences, Inc. | Modulation of protein methylation and phosphoprotein phosphate |
| ATE444286T1 (de) * | 2004-03-23 | 2009-10-15 | Dompe Pha R Ma Spa Res & Mfg | 2-phenylpropionsäurederivate und diese enthaltende pharmazeutische zusammensetzung |
| US7923041B2 (en) | 2005-02-03 | 2011-04-12 | Signum Biosciences, Inc. | Compositions and methods for enhancing cognitive function |
| WO2006084033A1 (en) | 2005-02-03 | 2006-08-10 | Signum Biosciences, Inc. | Compositions and methods for enhancing cognitive function |
| GB0525143D0 (en) | 2005-12-09 | 2006-01-18 | Novartis Ag | Organic compounds |
| GB0525144D0 (en) * | 2005-12-09 | 2006-01-18 | Novartis Ag | Organic compounds |
| JP5607025B2 (ja) | 2008-04-21 | 2014-10-15 | シグナム バイオサイエンシーズ， インコーポレイテッド | 化合物、組成物およびそれらを作製する方法 |
| CN103159674A (zh) * | 2013-04-03 | 2013-06-19 | 苏州安诺生物医药技术有限公司 | 2-苯烷酰胺类化合物及其制备方法、药物组合物和用途 |
| CN107398233B (zh) * | 2016-05-20 | 2019-07-05 | 中国石油天然气股份有限公司 | 一种酰胺基苯磺酸盐表面活性剂及其制备方法和应用 |
| MA53188A1 (fr) * | 2018-10-11 | 2021-12-31 | Basf As | Composés aromatiques et leurs utilisations pharmaceutiques |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB119562A (en) * | 1917-10-22 | 1918-10-10 | William Davidson | Improvements in Implements for Cultivating or Pulverising the Soil. |
| US2425821A (en) * | 1944-04-19 | 1947-08-19 | Paul A Peters | Method and apparatus for determining the eye color reflex sensation |
| US2425721A (en) | 1945-08-06 | 1947-08-19 | Univ Michigan | Thiophene compounds and methods of obtaining the same |
| GB1148909A (en) * | 1965-04-19 | 1969-04-16 | Sumitomo Chemical Co | Process for production of novel phenylhydrazone and phenylhydrazine derivatives |
| FR8113M (https=) * | 1967-07-26 | 1970-08-03 | ||
| ES356485A1 (es) * | 1967-07-26 | 1970-01-16 | Mcneilab Inc | Un procedimiento para la preparacion de nuevos acidos 5- aroilpirrol-2-carboxilicos y derivados de acido carboxilico. |
| US3752826A (en) * | 1970-01-26 | 1973-08-14 | Mcneilab Inc | Aroyl substituted pyrroles |
| US3833608A (en) * | 1970-11-23 | 1974-09-03 | Merck Sharp & Dohme | Indole-3-methanesulfonamides |
| US3883541A (en) | 1971-02-22 | 1975-05-13 | Dow Chemical Co | 4-Amino-3,5,6-trichloro-2-(functionally substituted methyl) pyridine compounds |
| AU5429699A (en) * | 1998-08-19 | 2000-03-14 | Theramark Limited | Drug targeting |
| NZ518376A (en) | 1999-11-18 | 2004-01-30 | Novartis Ag | Pesticidal aminoheterocyclamide compounds |
| IT1317826B1 (it) * | 2000-02-11 | 2003-07-15 | Dompe Spa | Ammidi, utili nell'inibizione della chemiotassi dei neutrofiliindotta da il-8. |
| US7135495B2 (en) * | 2000-03-09 | 2006-11-14 | Ono Pharmaceutical Co., Ltd. | Indole derivatives |
| ITMI20010395A1 (it) * | 2001-02-27 | 2002-08-27 | Dompe Spa | Omega-amminoalchilammidi di acidi r-2-aril-propionici come inibitori della chemiotassi di cellule polimorfonucleate e mononucleate |
| WO2003013526A1 (en) | 2001-08-08 | 2003-02-20 | Merck & Co. Inc. | Anticoagulant compounds |
| KR20040044856A (ko) * | 2001-09-07 | 2004-05-31 | 오노 야꾸힝 고교 가부시키가이샤 | 인돌 유도체 화합물 |
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2004
- 2004-02-04 RU RU2005127777/04A patent/RU2356887C2/ru not_active IP Right Cessation
- 2004-02-04 ES ES04707926.4T patent/ES2551929T3/es not_active Expired - Lifetime
- 2004-02-04 WO PCT/EP2004/001021 patent/WO2004069782A2/en not_active Ceased
- 2004-02-04 PT PT47079264T patent/PT1590314E/pt unknown
- 2004-02-04 JP JP2006501731A patent/JP5208411B2/ja not_active Expired - Fee Related
- 2004-02-04 DK DK04707926.4T patent/DK1590314T3/en active
- 2004-02-04 US US10/541,429 patent/US7776909B2/en not_active Expired - Fee Related
- 2004-02-04 SI SI200432275T patent/SI1590314T1/sl unknown
- 2004-02-04 EP EP04707926.4A patent/EP1590314B1/en not_active Expired - Lifetime
- 2004-02-04 CA CA2511582A patent/CA2511582C/en not_active Expired - Fee Related
- 2004-02-04 CN CNB2004800087419A patent/CN100562511C/zh not_active Expired - Fee Related
- 2004-02-04 AU AU2004210082A patent/AU2004210082B2/en not_active Ceased
- 2004-02-04 HU HUE04707926A patent/HUE026285T2/en unknown
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2005
- 2005-08-30 NO NO20054017A patent/NO334149B1/no not_active IP Right Cessation
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2010
- 2010-06-30 US US12/828,181 patent/US8871784B2/en not_active Expired - Fee Related
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2011
- 2011-03-22 AU AU2011201305A patent/AU2011201305B2/en not_active Ceased
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