JP2008525476A5 - - Google Patents
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- JP2008525476A5 JP2008525476A5 JP2007548472A JP2007548472A JP2008525476A5 JP 2008525476 A5 JP2008525476 A5 JP 2008525476A5 JP 2007548472 A JP2007548472 A JP 2007548472A JP 2007548472 A JP2007548472 A JP 2007548472A JP 2008525476 A5 JP2008525476 A5 JP 2008525476A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclopropa
- tetrahydro
- diaza
- pentalene
- compound according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- YZGJIENQZBJQNS-UHFFFAOYSA-N pentalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C21 YZGJIENQZBJQNS-UHFFFAOYSA-N 0.000 claims description 4
- TWKUMVSEPLJJQZ-UHFFFAOYSA-N 3-ethyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(CC)C2CC=2C1=NNC=2C(O)=O TWKUMVSEPLJJQZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 79
- 239000000203 mixture Substances 0.000 claims 28
- 150000003839 salts Chemical class 0.000 claims 26
- 239000012453 solvate Substances 0.000 claims 26
- 150000004677 hydrates Chemical class 0.000 claims 23
- 125000003545 alkoxy group Chemical group 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 18
- -1 alkyl thiocarboxamide Chemical compound 0.000 claims 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 16
- 229910052799 carbon Inorganic materials 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 125000004414 alkyl thio group Chemical group 0.000 claims 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
- 201000001320 Atherosclerosis Diseases 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 230000002503 metabolic effect Effects 0.000 claims 10
- 238000002560 therapeutic procedure Methods 0.000 claims 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims 8
- 125000004995 haloalkylthio group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims 7
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 7
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- 241001465754 Metazoa Species 0.000 claims 6
- 125000002252 acyl group Chemical group 0.000 claims 6
- 125000004423 acyloxy group Chemical group 0.000 claims 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- 150000003857 carboxamides Chemical class 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 6
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 208000032928 Dyslipidaemia Diseases 0.000 claims 4
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 4
- 125000005431 alkyl carboxamide group Chemical group 0.000 claims 4
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000005432 dialkylcarboxamide group Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 4
- 229940124530 sulfonamide Drugs 0.000 claims 4
- 150000003456 sulfonamides Chemical class 0.000 claims 4
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 4
- 229920002554 vinyl polymer Polymers 0.000 claims 4
- 206010022489 Insulin Resistance Diseases 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 208000029078 coronary artery disease Diseases 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- OTMHRRBDBDERSZ-UHFFFAOYSA-N 3-benzyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12CC3=C(C(=O)O)NN=C3C2C1CC1=CC=CC=C1 OTMHRRBDBDERSZ-UHFFFAOYSA-N 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- 208000002705 Glucose Intolerance Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 235000014676 Phragmites communis Nutrition 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000007536 Thrombosis Diseases 0.000 claims 2
- 239000000556 agonist Substances 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 2
- 125000005110 aryl thio group Chemical group 0.000 claims 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 2
- 238000010276 construction Methods 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims 2
- DVJZLBFGLLGJNR-UHFFFAOYSA-N ethyl 3-ethyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylate Chemical compound C1C2=C(C(=O)OCC)NN=C2C2C(CC)C21 DVJZLBFGLLGJNR-UHFFFAOYSA-N 0.000 claims 2
- 239000003925 fat Substances 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 208000019622 heart disease Diseases 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 201000009104 prediabetes syndrome Diseases 0.000 claims 2
- 239000002464 receptor antagonist Substances 0.000 claims 2
- 229940044551 receptor antagonist Drugs 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- WVIAXGYIVDKKEC-UHFFFAOYSA-N (+/-)-1,1-dimethyl-1a,3,5,5a-tetrahydro-1h-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid Chemical compound C12C(C)(C)C2CC=2C1=NNC=2C(O)=O WVIAXGYIVDKKEC-UHFFFAOYSA-N 0.000 claims 1
- RAILBMQEZUOZPY-UHFFFAOYSA-N (+/-)-1,1-dimethyl-1a,3,5,5a-tetrahydro-1h-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid ethyl ester Chemical compound C1C2=C(C(=O)OCC)NN=C2C2C(C)(C)C12 RAILBMQEZUOZPY-UHFFFAOYSA-N 0.000 claims 1
- VSBDNNUJQGUHKD-UHFFFAOYSA-N (+/-)-1,1-dimethyl-4-(2h-tetrazol-5-yl)-1a,3,5,5a-tetrahydro-1h-2,3-diaza-cyclopropa[a]pentalene Chemical compound C12C(C)(C)C2CC=2C1=NNC=2C=1N=NNN=1 VSBDNNUJQGUHKD-UHFFFAOYSA-N 0.000 claims 1
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims 1
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims 1
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- ZNSMRESAJQMQFB-UHFFFAOYSA-N 3-(2-methylpropyl)-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12C(CC(C)C)C2CC=2C1=NNC=2C=1N=NNN=1 ZNSMRESAJQMQFB-UHFFFAOYSA-N 0.000 claims 1
- JQOLBGNVBHBYTN-UHFFFAOYSA-N 3-(2-methylpropyl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(CC(C)C)C2CC=2C1=NNC=2C(O)=O JQOLBGNVBHBYTN-UHFFFAOYSA-N 0.000 claims 1
- UZFHZWKLQQVCHG-UHFFFAOYSA-N 3-(ethoxymethyl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(COCC)C2CC=2C1=NNC=2C(O)=O UZFHZWKLQQVCHG-UHFFFAOYSA-N 0.000 claims 1
- ODUVQBROUWOBDH-UHFFFAOYSA-N 3-(hydroxymethyl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(CO)C2CC=2C1=NNC=2C(O)=O ODUVQBROUWOBDH-UHFFFAOYSA-N 0.000 claims 1
- SNHAYNGAPALUSS-UHFFFAOYSA-N 3-(methoxymethyl)-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12C(COC)C2CC=2C1=NNC=2C=1N=NNN=1 SNHAYNGAPALUSS-UHFFFAOYSA-N 0.000 claims 1
- APQANBAOGDTTDE-UHFFFAOYSA-N 3-(methoxymethyl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(COC)C2CC=2C1=NNC=2C(O)=O APQANBAOGDTTDE-UHFFFAOYSA-N 0.000 claims 1
- UDQHREJCGBMEQZ-UHFFFAOYSA-N 3-(methylsulfanylmethyl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(CSC)C2CC=2C1=NNC=2C(O)=O UDQHREJCGBMEQZ-UHFFFAOYSA-N 0.000 claims 1
- XJNZFQMEFRFJIV-UHFFFAOYSA-N 3-(phenoxymethyl)-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12CC(=C(NN=3)C4=NNN=N4)C=3C2C1COC1=CC=CC=C1 XJNZFQMEFRFJIV-UHFFFAOYSA-N 0.000 claims 1
- LUCHJPWHYQGXLE-NSCUHMNNSA-N 3-[(E)-prop-1-enyl]-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12C(/C=C/C)C2CC=2C1=NNC=2C=1N=NNN=1 LUCHJPWHYQGXLE-NSCUHMNNSA-N 0.000 claims 1
- VIQDOSDFYBSVKH-NSCUHMNNSA-N 3-[(E)-prop-1-enyl]-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(/C=C/C)C2CC=2C1=NNC=2C(O)=O VIQDOSDFYBSVKH-NSCUHMNNSA-N 0.000 claims 1
- LUCHJPWHYQGXLE-IHWYPQMZSA-N 3-[(Z)-prop-1-enyl]-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12C(\C=C/C)C2CC=2C1=NNC=2C=1N=NNN=1 LUCHJPWHYQGXLE-IHWYPQMZSA-N 0.000 claims 1
- VIQDOSDFYBSVKH-IHWYPQMZSA-N 3-[(Z)-prop-1-enyl]-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(\C=C/C)C2CC=2C1=NNC=2C(O)=O VIQDOSDFYBSVKH-IHWYPQMZSA-N 0.000 claims 1
- VYWKYLOLYLNJFO-UHFFFAOYSA-N 3-butyl-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12C(CCCC)C2CC=2C1=NNC=2C=1N=NNN=1 VYWKYLOLYLNJFO-UHFFFAOYSA-N 0.000 claims 1
- HZGMLBXSQLGHIS-UHFFFAOYSA-N 3-butyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(CCCC)C2CC=2C1=NNC=2C(O)=O HZGMLBXSQLGHIS-UHFFFAOYSA-N 0.000 claims 1
- BUTFUADABNFVEZ-UHFFFAOYSA-N 3-cyclopropyl-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C1CC1C1C2C3=NNC(C4=NNN=N4)=C3CC21 BUTFUADABNFVEZ-UHFFFAOYSA-N 0.000 claims 1
- KRGVFHQAOMELTE-UHFFFAOYSA-N 3-cyclopropyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C1C2=C(C(=O)O)NN=C2C2C1C2C1CC1 KRGVFHQAOMELTE-UHFFFAOYSA-N 0.000 claims 1
- UCNBXLZANXGQAD-UHFFFAOYSA-N 3-ethenyl-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12C(C=C)C2CC=2C1=NNC=2C=1N=NNN=1 UCNBXLZANXGQAD-UHFFFAOYSA-N 0.000 claims 1
- RTJPVQFTNJBAAO-UHFFFAOYSA-N 3-ethenyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C1C2=C(C(=O)O)NN=C2C2C(C=C)C12 RTJPVQFTNJBAAO-UHFFFAOYSA-N 0.000 claims 1
- SYZZVQFBZIIAPM-UHFFFAOYSA-N 3-ethyl-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12C(CC)C2CC=2C1=NNC=2C=1N=NNN=1 SYZZVQFBZIIAPM-UHFFFAOYSA-N 0.000 claims 1
- NFZMLDIEJQTJDW-UHFFFAOYSA-N 3-methyl-7,8-diazatricyclo[4.3.0.02,4]nona-1(6),8-diene-9-carboxylic acid Chemical compound N1C(C(O)=O)=C2C3C(C)C3CC2=N1 NFZMLDIEJQTJDW-UHFFFAOYSA-N 0.000 claims 1
- SOPWSSMPKDHAFO-UHFFFAOYSA-N 3-methyl-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12C(C)C2CC=2C1=NNC=2C=1N=NNN=1 SOPWSSMPKDHAFO-UHFFFAOYSA-N 0.000 claims 1
- RTKOUBUTPYWYHC-UHFFFAOYSA-N 3-methyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(C)C2CC=2C1=NNC=2C(O)=O RTKOUBUTPYWYHC-UHFFFAOYSA-N 0.000 claims 1
- HGMKQXPTBSXDTB-UHFFFAOYSA-N 3-pentyl-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12C(CCCCC)C2CC=2C1=NNC=2C=1N=NNN=1 HGMKQXPTBSXDTB-UHFFFAOYSA-N 0.000 claims 1
- LRSWOBPCCZMIMT-UHFFFAOYSA-N 3-pentyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(CCCCC)C2CC=2C1=NNC=2C(O)=O LRSWOBPCCZMIMT-UHFFFAOYSA-N 0.000 claims 1
- ADDWQSJBENMLJW-UHFFFAOYSA-N 3-phenyl-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12=NNC(C3=NNN=N3)=C2CC2C1C2C1=CC=CC=C1 ADDWQSJBENMLJW-UHFFFAOYSA-N 0.000 claims 1
- HJVDLDUXOXOQJX-UHFFFAOYSA-N 3-phenyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C1C2=C(C(=O)O)NN=C2C2C1C2C1=CC=CC=C1 HJVDLDUXOXOQJX-UHFFFAOYSA-N 0.000 claims 1
- ULNGMOCVPKLURH-UHFFFAOYSA-N 3-propan-2-yl-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12C(C(C)C)C2CC=2C1=NNC=2C=1N=NNN=1 ULNGMOCVPKLURH-UHFFFAOYSA-N 0.000 claims 1
- ZAKPZERPWYRHOO-UHFFFAOYSA-N 3-propan-2-yl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(C(C)C)C2CC=2C1=NNC=2C(O)=O ZAKPZERPWYRHOO-UHFFFAOYSA-N 0.000 claims 1
- DVPRKEHZURSZOL-UHFFFAOYSA-N 3-propyl-7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene Chemical compound C12C(CCC)C2CC=2C1=NNC=2C=1N=NNN=1 DVPRKEHZURSZOL-UHFFFAOYSA-N 0.000 claims 1
- CSMSFPLNDIGDBG-UHFFFAOYSA-N 3-propyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylic acid Chemical compound C12C(CCC)C2CC=2C1=NNC=2C(O)=O CSMSFPLNDIGDBG-UHFFFAOYSA-N 0.000 claims 1
- UKQFEWRNKWDNBW-UHFFFAOYSA-N 7,8-diazatricyclo[4.3.0.02,4]nona-1(6),8-diene-9-carboxylic acid Chemical compound C1C2CC2C2=C(C(=O)O)NN=C21 UKQFEWRNKWDNBW-UHFFFAOYSA-N 0.000 claims 1
- UTILKUIIYSZFGD-UHFFFAOYSA-N 7-(2H-tetrazol-5-yl)spiro[8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-3,1'-cyclohexane] Chemical compound C=12CC(C34CCCCC4)C3C2=NNC=1C1=NN=NN1 UTILKUIIYSZFGD-UHFFFAOYSA-N 0.000 claims 1
- ZUADEZLTQJTWKW-UHFFFAOYSA-N 7-(2H-tetrazol-5-yl)spiro[8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-3,1'-cyclopentane] Chemical compound C1CCCC21C1C3=NNC(C=4NN=NN=4)=C3CC12 ZUADEZLTQJTWKW-UHFFFAOYSA-N 0.000 claims 1
- 239000005541 ACE inhibitor Substances 0.000 claims 1
- 229940118148 Aldose reductase inhibitor Drugs 0.000 claims 1
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims 1
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims 1
- 229940123208 Biguanide Drugs 0.000 claims 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims 1
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims 1
- AVUUOKAXFDRGKK-UHFFFAOYSA-N C12CC3=C(C(=O)O)NN=C3C2C1COC1=CC=CC=C1 Chemical compound C12CC3=C(C(=O)O)NN=C3C2C1COC1=CC=CC=C1 AVUUOKAXFDRGKK-UHFFFAOYSA-N 0.000 claims 1
- ZYICRESAGWVMJD-UHFFFAOYSA-N C=1C=CC=CC=1CC(C12)C2CC=2C1=NNC=2C=1N=NNN=1 Chemical compound C=1C=CC=CC=1CC(C12)C2CC=2C1=NNC=2C=1N=NNN=1 ZYICRESAGWVMJD-UHFFFAOYSA-N 0.000 claims 1
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- 229940122199 Insulin secretagogue Drugs 0.000 claims 1
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- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 claims 1
- 229940123464 Thiazolidinedione Drugs 0.000 claims 1
- SSWAVSFICWGNDI-UHFFFAOYSA-N [7-(2H-tetrazol-5-yl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-dien-3-yl]methanol Chemical compound C12C(CO)C2CC=2C1=NNC=2C=1N=NNN=1 SSWAVSFICWGNDI-UHFFFAOYSA-N 0.000 claims 1
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- ADQXTVQLMDRXSS-UHFFFAOYSA-N chembl2057611 Chemical compound C1C2=C(C(=O)O)NN=C2C2C1C21CCCCC1 ADQXTVQLMDRXSS-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- CVGCMDRAPYDYKU-UHFFFAOYSA-N ethyl 3-(hydroxymethyl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylate Chemical compound C1C2=C(C(=O)OCC)NN=C2C2C(CO)C21 CVGCMDRAPYDYKU-UHFFFAOYSA-N 0.000 claims 1
- RTTVBWWZIFWXIM-UHFFFAOYSA-N ethyl 3-(methoxymethyl)-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylate Chemical compound C1C2=C(C(=O)OCC)NN=C2C2C(COC)C21 RTTVBWWZIFWXIM-UHFFFAOYSA-N 0.000 claims 1
- LEVIRGHKZOJUSM-UHFFFAOYSA-N ethyl 3-benzyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylate Chemical compound C12CC3=C(C(=O)OCC)NN=C3C2C1CC1=CC=CC=C1 LEVIRGHKZOJUSM-UHFFFAOYSA-N 0.000 claims 1
- KDQCNWZFNDCEFU-UHFFFAOYSA-N ethyl 3-ethenyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylate Chemical compound C1C2=C(C(=O)OCC)NN=C2C2C(C=C)C12 KDQCNWZFNDCEFU-UHFFFAOYSA-N 0.000 claims 1
- DXRBIJZTOKZLLK-UHFFFAOYSA-N ethyl 3-methyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylate Chemical compound C1C2=C(C(=O)OCC)NN=C2C2C(C)C21 DXRBIJZTOKZLLK-UHFFFAOYSA-N 0.000 claims 1
- SSDFWQQQLZIBPZ-UHFFFAOYSA-N ethyl 3-pentyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylate Chemical compound C12C(CCCCC)C2CC=2C1=NNC=2C(=O)OCC SSDFWQQQLZIBPZ-UHFFFAOYSA-N 0.000 claims 1
- MCFPMJSSFCJQNZ-UHFFFAOYSA-N ethyl 3-phenyl-8,9-diazatricyclo[4.3.0.02,4]nona-1(6),7-diene-7-carboxylate Chemical compound C1C2=C(C(=O)OCC)NN=C2C2C1C2C1=CC=CC=C1 MCFPMJSSFCJQNZ-UHFFFAOYSA-N 0.000 claims 1
- 229940125753 fibrate Drugs 0.000 claims 1
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- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 239000004031 partial agonist Substances 0.000 claims 1
- GUVXZFRDPCKWEM-UHFFFAOYSA-N pentalene Chemical compound C1=CC2=CC=CC2=C1 GUVXZFRDPCKWEM-UHFFFAOYSA-N 0.000 claims 1
- 229940031439 squalene Drugs 0.000 claims 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 150000003536 tetrazoles Chemical class 0.000 claims 1
- DKSPRNJUDCWTID-QWWZWVQMSA-N C1[C@H]2c3n[nH]c(-c4n[nH]nn4)c3C[C@@H]12 Chemical compound C1[C@H]2c3n[nH]c(-c4n[nH]nn4)c3C[C@@H]12 DKSPRNJUDCWTID-QWWZWVQMSA-N 0.000 description 1
- GEIJZLPFMLXVQN-KVWYPCGYSA-N C=CCC1[C@H]2c3n[nH]c(-c4n[nH]nn4)c3C[C@@H]12 Chemical compound C=CCC1[C@H]2c3n[nH]c(-c4n[nH]nn4)c3C[C@@H]12 GEIJZLPFMLXVQN-KVWYPCGYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
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| US67652105P | 2005-04-29 | 2005-04-29 | |
| PCT/US2005/046599 WO2006069242A2 (en) | 2004-12-23 | 2005-12-22 | Fused pyrazole derivatives and uses thereof in methods of treatment of metabolic-related?disorders |
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Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI258478B (en) | 2003-10-31 | 2006-07-21 | Arena Pharm Inc | Tetrazole derivatives and methods of treatment of metabolic-related disorders thereof |
| ES2331521T3 (es) * | 2003-11-21 | 2010-01-07 | Arena Pharmaceuticals, Inc. | Derivados de acido 4-oxo-4,5-dihidro-furan-2-carboxilico y procedimientos de tratamiento de trastornos metabolicos relacionados del mismo. |
| PE20060949A1 (es) * | 2004-12-23 | 2006-10-11 | Arena Pharm Inc | Derivados fusionados de pirazol como agonistas del receptor de niacina |
| PT1901731E (pt) | 2005-06-28 | 2011-05-11 | Merck Sharp & Dohme | Agonistas de receptor de niacina, composi??es que cont?m tais compostos e m?todos de tratamento |
| EP2061767B1 (de) | 2006-08-08 | 2014-12-17 | Sanofi | Arylaminoaryl-alkyl-substituierte Imidazolidin-2,4-dione, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Arzneimittel und ihre Verwendung |
| DE102007005045B4 (de) | 2007-01-26 | 2008-12-18 | Sanofi-Aventis | Phenothiazin Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE102007054497B3 (de) | 2007-11-13 | 2009-07-23 | Sanofi-Aventis Deutschland Gmbh | Neue kristalline Diphenylazetidinonhydrate und Verfahren zu deren Herstellung |
| UY31968A (es) | 2008-07-09 | 2010-01-29 | Sanofi Aventis | Nuevos derivados heterocíclicos, sus procesos para su preparación, y sus usos terapéuticos |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| KR20120060207A (ko) | 2009-08-26 | 2012-06-11 | 사노피 | 신규한 결정성 헤테로방향족 플루오로글리코시드 수화물, 이들 화합물을 포함하는 약제 및 이들의 용도 |
| IN2012DN02474A (https=) * | 2009-08-28 | 2015-08-21 | Arena Pharm Inc | |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| AU2012222149B2 (en) | 2011-02-25 | 2017-06-29 | Arena Pharmaceuticals, Inc. | Cannabinoid receptor modulators |
| EP2678330A1 (en) | 2011-02-25 | 2014-01-01 | Arena Pharmaceuticals, Inc. | Crystalline forms and processes for the preparation of condensed azacycles ( cannabinoid receptor modulators) |
| US9597340B2 (en) | 2011-02-25 | 2017-03-21 | Arena Pharmaceuticals, Inc. | Cannabinoid receptor modulators |
| WO2012116278A1 (en) * | 2011-02-25 | 2012-08-30 | Arena Pharmaceuticals, Inc. | Cannabinoid receptor modulators |
| EP2683702B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8895547B2 (en) | 2011-03-08 | 2014-11-25 | Sanofi | Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| WO2012120058A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120051A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| HK1210825A1 (en) | 2012-07-11 | 2016-05-06 | Elcelyx Therapeutics, Inc. | Compositions comprising statins, biguanides and further agents for reducing cardiometabolic risk |
| US20200078358A1 (en) | 2017-05-08 | 2020-03-12 | Arena Pharmaceuticals, Inc. | Compounds and Methods for Treatment of Visceral Pain |
| AU2019318209B2 (en) | 2018-08-10 | 2025-09-25 | Diapin Therapeutics, Llc | Tri-peptides and treatment of metabolic, cardiovascular and inflammatory disorders |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3105336A (en) * | 1961-05-16 | 1963-10-01 | Package Machinery Co | Converting wrapping machines to wrap different size articles |
| US4613610A (en) * | 1984-06-22 | 1986-09-23 | Sandoz Pharmaceuticals Corp. | Cholesterol biosynthesis inhibiting pyrazole analogs of mevalonolactone and its derivatives |
| US5134155A (en) | 1991-08-08 | 1992-07-28 | Ortho Pharmaceutical Corporation | Tetrahydroindazole, tetrahydrocyclopentapyrazole, and hexahydrocycloheptapyrazole compounds and their use as HMG-coA reductase inhibitors |
| WO2000007996A2 (en) * | 1998-08-07 | 2000-02-17 | Chiron Corporation | Pyrazoles as estrogen receptor modulators |
| EP1262475A4 (en) | 2000-03-09 | 2005-01-05 | Ono Pharmaceutical Co | INDOIND DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE |
| US20010047027A1 (en) | 2000-04-12 | 2001-11-29 | Marc Labelle | Prostaglandin D2 receptor antagonists |
| US6410583B1 (en) | 2000-07-25 | 2002-06-25 | Merck Frosst Canada & Co. | Cyclopentanoindoles, compositions containing such compounds and methods of treatment |
| AU2002302248B2 (en) | 2001-05-23 | 2008-03-06 | Merck Frosst Canada Ltd. | Dihydropyrrolo[1,2-A]indole and tetrahydropyrido[1,2-A]-indole derivatives as prostaglandin D2 receptor antagonists |
| JP3968076B2 (ja) | 2001-06-27 | 2007-08-29 | アールエス テック コーポレイション | 新しいキラルサレン化合物、キラルサレン触媒及びこれを利用したラセミックエポキシ化合物からキラル化合物を製造する方法 |
| CA2459515A1 (en) | 2001-09-07 | 2003-03-20 | Kazuhiko Torisu | Indole derivatives |
| DE10148617A1 (de) * | 2001-09-25 | 2003-04-24 | Schering Ag | Substituierte N-(1,4,5,6-Tetrahydro-cyclopentapyrazol-3-yl)-Derivate, deren Herstellung und Verwendung als Arzneimittel |
| AR038136A1 (es) | 2002-01-24 | 2004-12-29 | Merck Frosst Canada Inc | Cicloalcanindoles con sustitucion con fluor composiciones que contienen estos compuestos y metodos de tratamiento |
| MXPA04009095A (es) | 2002-03-19 | 2004-12-06 | Ono Pharmaceutical Co | Compuesto de acido carboxilico y agente farmaceutico que comprende el compuesto como ingrediente activo. |
| AU2003282679A1 (en) | 2002-10-04 | 2004-05-04 | Arena Pharmaceuticals, Inc. | Hydroxypyrazoles for use against metabolic-related disorders |
| CA2501134A1 (en) * | 2002-10-10 | 2004-04-22 | Arena Pharmaceuticals, Inc. | 5-substituted 2h-pyrazole-3-carboxylic acid derivatives as antilipolytic agents for the treatment of metabolic-related disorders such as dyslipidemia |
| AR041089A1 (es) | 2003-05-15 | 2005-05-04 | Merck & Co Inc | Procedimiento y composiciones farmaceutiicas para tratar aterosclerosis, dislipidemias y afecciones relacionadas |
| WO2005011677A1 (en) * | 2003-06-13 | 2005-02-10 | Arena Pharmaceuticals, Inc. | 5-substituted 2h-pyrazole-3-carboxylic acid derivatives as agonists for the nicotinic acid receptor rup25 for the treatment of dyslipidemia and related diseases |
| GB0319126D0 (en) | 2003-08-14 | 2003-09-17 | Smithkline Beecham Corp | Chemical compounds |
| GB0319124D0 (en) | 2003-08-14 | 2003-09-17 | Smithkline Beecham Corp | Chemical compounds |
| TWI258478B (en) | 2003-10-31 | 2006-07-21 | Arena Pharm Inc | Tetrazole derivatives and methods of treatment of metabolic-related disorders thereof |
| PL1781657T3 (pl) | 2004-02-14 | 2013-08-30 | Glaxosmithkline Ip Dev Ltd | Leki o aktywności wobec receptora HM74A |
| PE20060949A1 (es) * | 2004-12-23 | 2006-10-11 | Arena Pharm Inc | Derivados fusionados de pirazol como agonistas del receptor de niacina |
-
2005
- 2005-12-15 PE PE2005001472A patent/PE20060949A1/es not_active Application Discontinuation
- 2005-12-20 GT GT200500379A patent/GT200500379A/es unknown
- 2005-12-21 HN HN2005036256A patent/HN2005036256A/es unknown
- 2005-12-21 TW TW094145549A patent/TW200635904A/zh unknown
- 2005-12-21 AR ARP050105438A patent/AR055015A1/es not_active Application Discontinuation
- 2005-12-22 JP JP2007548472A patent/JP2008525476A/ja not_active Withdrawn
- 2005-12-22 CA CA002589648A patent/CA2589648A1/en not_active Abandoned
- 2005-12-22 EA EA200701361A patent/EA013184B1/ru not_active IP Right Cessation
- 2005-12-22 WO PCT/US2005/046599 patent/WO2006069242A2/en not_active Ceased
- 2005-12-22 BR BRPI0519262-5A patent/BRPI0519262A2/pt not_active IP Right Cessation
- 2005-12-22 AU AU2005319121A patent/AU2005319121A1/en not_active Abandoned
- 2005-12-22 CN CN2011102214069A patent/CN102321024A/zh active Pending
- 2005-12-22 US US11/315,753 patent/US7241792B2/en not_active Expired - Lifetime
- 2005-12-22 GE GEAP200510188A patent/GEP20105126B/en unknown
- 2005-12-22 NZ NZ555721A patent/NZ555721A/en not_active IP Right Cessation
- 2005-12-22 EP EP05857182A patent/EP1831178A2/en not_active Withdrawn
- 2005-12-22 KR KR1020077016787A patent/KR20070088808A/ko not_active Ceased
- 2005-12-22 CN CN2011102214054A patent/CN102311378A/zh active Pending
- 2005-12-23 PA PA20058658301A patent/PA8658301A1/es unknown
-
2006
- 2006-11-17 US US11/601,184 patent/US7612106B2/en not_active Expired - Fee Related
-
2007
- 2007-06-04 IL IL183654A patent/IL183654A0/en unknown
- 2007-06-20 CU CU20070144A patent/CU23691B7/es not_active IP Right Cessation
- 2007-06-20 TN TNP2007000236A patent/TNSN07236A1/fr unknown
- 2007-06-21 NI NI200700161A patent/NI200700161A/es unknown
- 2007-07-12 MA MA30071A patent/MA29148B1/fr unknown
- 2007-07-19 NO NO20073766A patent/NO20073766L/no not_active Application Discontinuation
-
2009
- 2009-04-30 US US12/433,704 patent/US20090258892A1/en not_active Abandoned
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