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- Withdrawn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
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- 229940122199 Insulin secretagogue Drugs 0.000 claims 1
- NKWYBVCRLYYJIX-UHFFFAOYSA-N N1NC=C2C=C3CC3C21 Chemical compound N1NC=C2C=C3CC3C21 NKWYBVCRLYYJIX-UHFFFAOYSA-N 0.000 claims 1
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- 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
- 239000003288 aldose reductase inhibitor Substances 0.000 claims 1
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims 1
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- 230000003143 atherosclerotic effect Effects 0.000 claims 1
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- 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
- CUTZNERBKDMLAP-UHFFFAOYSA-N gtpl5785 Chemical compound C1C2=C(C(=O)O)NN=C2C2CC21 CUTZNERBKDMLAP-UHFFFAOYSA-N 0.000 claims 1
- 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 |
Publications (2)
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| JP2008525476A JP2008525476A (ja) | 2008-07-17 |
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| SI1901731T1 (sl) | 2005-06-28 | 2011-07-29 | Merck Sharp & Dohme | Niacin receptorski antagonisti, sestavki vsebujoäśi take spojine in postopki zdravljenja |
| JP2010500300A (ja) | 2006-08-08 | 2010-01-07 | サノフィ−アベンティス | アリールアミノアリール−アルキル−置換イミダゾリジン−２，４−ジオン、それらの製造法、それらの化合物を含有する薬剤、およびそれらの使用 |
| 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 |
| WO2010003624A2 (en) | 2008-07-09 | 2010-01-14 | Sanofi-Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| 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 |
| MX2012001729A (es) | 2009-08-26 | 2012-06-13 | Sanofi Sa | Nuevos hidratos cristalinos de fluoroglicosido heteroaromatico, productos farmaceuticos que comprenden estos compuestos, y su empleo. |
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| WO2011157827A1 (de) | 2010-06-18 | 2011-12-22 | 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 |
| 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 |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
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| CN103492369B (zh) * | 2011-02-25 | 2019-03-29 | 艾尼纳制药公司 | 大麻素受体调节剂 |
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| EP2683701B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683698B1 (de) | 2011-03-08 | 2017-10-04 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8828995B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Branched oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and 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 |
| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| WO2012120052A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, 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 |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
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-
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 WO PCT/US2005/046599 patent/WO2006069242A2/en not_active Ceased
- 2005-12-22 CN CN2011102214069A patent/CN102321024A/zh active Pending
- 2005-12-22 AU AU2005319121A patent/AU2005319121A1/en not_active Abandoned
- 2005-12-22 CN CN2011102214054A patent/CN102311378A/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 EP EP05857182A patent/EP1831178A2/en not_active Withdrawn
- 2005-12-22 NZ NZ555721A patent/NZ555721A/en not_active IP Right Cessation
- 2005-12-22 JP JP2007548472A patent/JP2008525476A/ja not_active Withdrawn
- 2005-12-22 BR BRPI0519262-5A patent/BRPI0519262A2/pt not_active IP Right Cessation
- 2005-12-22 EA EA200701361A patent/EA013184B1/ru not_active IP Right Cessation
- 2005-12-22 KR KR1020077016787A patent/KR20070088808A/ko not_active Ceased
- 2005-12-22 CA CA002589648A patent/CA2589648A1/en not_active Abandoned
- 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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