JP2008525476A - 代謝関連障害の処置法における縮合ピラゾール誘導体およびその使用 - Google Patents
代謝関連障害の処置法における縮合ピラゾール誘導体およびその使用 Download PDFInfo
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- JP2008525476A JP2008525476A JP2007548472A JP2007548472A JP2008525476A JP 2008525476 A JP2008525476 A JP 2008525476A JP 2007548472 A JP2007548472 A JP 2007548472A JP 2007548472 A JP2007548472 A JP 2007548472A JP 2008525476 A JP2008525476 A JP 2008525476A
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- Prior art keywords
- tetrahydro
- cyclopropa
- diaza
- pentalene
- carboxylic acid
- 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.)
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- 238000000034 method Methods 0.000 title claims abstract description 125
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- 208000030159 metabolic disease Diseases 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 552
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 90
- 238000011282 treatment Methods 0.000 claims abstract description 58
- 150000003839 salts Chemical class 0.000 claims abstract description 52
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 50
- 230000002503 metabolic effect Effects 0.000 claims abstract description 44
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 42
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 36
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 35
- 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 29
- 208000017170 Lipid metabolism disease Diseases 0.000 claims abstract description 26
- 239000000556 agonist Substances 0.000 claims abstract description 26
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- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims abstract description 16
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims abstract description 16
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 15
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims abstract description 13
- 239000002464 receptor antagonist Substances 0.000 claims abstract description 13
- 229940044551 receptor antagonist Drugs 0.000 claims abstract description 13
- 229940123208 Biguanide Drugs 0.000 claims abstract description 12
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims abstract description 11
- 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 abstract description 10
- 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 abstract description 10
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims abstract description 10
- 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 abstract description 10
- 229940031439 squalene Drugs 0.000 claims abstract description 10
- 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 abstract description 10
- 208000011580 syndromic disease Diseases 0.000 claims abstract description 9
- 229940125753 fibrate Drugs 0.000 claims abstract description 8
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229940118148 Aldose reductase inhibitor Drugs 0.000 claims abstract description 6
- 239000003288 aldose reductase inhibitor Substances 0.000 claims abstract description 6
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- -1 alkyl thiocarboxamide Chemical compound 0.000 claims description 216
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 239000003814 drug Substances 0.000 claims description 52
- 239000012453 solvate Substances 0.000 claims description 46
- 125000003545 alkoxy group Chemical group 0.000 claims description 45
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- YZGJIENQZBJQNS-UHFFFAOYSA-N pentalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C21 YZGJIENQZBJQNS-UHFFFAOYSA-N 0.000 claims description 36
- GUVXZFRDPCKWEM-UHFFFAOYSA-N pentalene Chemical compound C1=CC2=CC=CC2=C1 GUVXZFRDPCKWEM-UHFFFAOYSA-N 0.000 claims description 35
- 201000010099 disease Diseases 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 32
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
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- 125000001424 substituent group Chemical group 0.000 claims description 23
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 125000002252 acyl group Chemical group 0.000 claims description 20
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 19
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 17
- 239000003937 drug carrier Substances 0.000 claims description 17
- 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 description 17
- 150000003857 carboxamides Chemical class 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 16
- 125000004423 acyloxy group Chemical group 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 15
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 15
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 14
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 13
- 238000002560 therapeutic procedure Methods 0.000 claims description 13
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 12
- 125000005431 alkyl carboxamide group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 230000003143 atherosclerotic effect Effects 0.000 claims description 12
- 125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 229940124530 sulfonamide Drugs 0.000 claims description 12
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 11
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 10
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 10
- 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 description 10
- 208000008589 Obesity Diseases 0.000 claims description 9
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 9
- 235000020824 obesity Nutrition 0.000 claims description 9
- 239000004031 partial agonist Substances 0.000 claims description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
- 239000005541 ACE inhibitor Substances 0.000 claims description 8
- 206010020772 Hypertension Diseases 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 7
- 208000006011 Stroke Diseases 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 7
- 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 description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
- 229940122199 Insulin secretagogue Drugs 0.000 claims description 6
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 6
- 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 description 5
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
- 229940123464 Thiazolidinedione Drugs 0.000 claims description 5
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 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 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 4
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 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 description 4
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims description 4
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- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims description 4
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 4
- CUTZNERBKDMLAP-UHFFFAOYSA-N gtpl5785 Chemical compound C1C2=C(C(=O)O)NN=C2C2CC21 CUTZNERBKDMLAP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 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 description 2
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
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- CYZOEHLTHQQWSY-UHFFFAOYSA-N chembl2057610 Chemical compound C1C2=C(C(=O)O)NN=C2C2C1C21CCCC1 CYZOEHLTHQQWSY-UHFFFAOYSA-N 0.000 claims description 2
- ADQXTVQLMDRXSS-UHFFFAOYSA-N chembl2057611 Chemical compound C1C2=C(C(=O)O)NN=C2C2C1C21CCCCC1 ADQXTVQLMDRXSS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 4
- 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
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- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 2
- 238000010276 construction Methods 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
- 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
- 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
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- 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
- 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 1
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- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- PBVNHDMBCZSEMD-CYCLDIHTSA-K trisodium;[[(2r,3s,4r,5r)-5-(2-amino-6-oxo-3h-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-oxidophosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O PBVNHDMBCZSEMD-CYCLDIHTSA-K 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 239000000777 urocortin Substances 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 229940046001 vitamin b complex Drugs 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000011680 zucker rat Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63866804P | 2004-12-23 | 2004-12-23 | |
| 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)
| Publication Number | Publication Date |
|---|---|
| JP2008525476A true JP2008525476A (ja) | 2008-07-17 |
| JP2008525476A5 JP2008525476A5 (https=) | 2009-02-12 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007548472A Withdrawn JP2008525476A (ja) | 2004-12-23 | 2005-12-22 | 代謝関連障害の処置法における縮合ピラゾール誘導体およびその使用 |
Country Status (24)
| Country | Link |
|---|---|
| US (3) | US7241792B2 (https=) |
| EP (1) | EP1831178A2 (https=) |
| JP (1) | JP2008525476A (https=) |
| KR (1) | KR20070088808A (https=) |
| CN (2) | CN102321024A (https=) |
| AR (1) | AR055015A1 (https=) |
| AU (1) | AU2005319121A1 (https=) |
| BR (1) | BRPI0519262A2 (https=) |
| CA (1) | CA2589648A1 (https=) |
| CU (1) | CU23691B7 (https=) |
| EA (1) | EA013184B1 (https=) |
| GE (1) | GEP20105126B (https=) |
| GT (1) | GT200500379A (https=) |
| HN (1) | HN2005036256A (https=) |
| IL (1) | IL183654A0 (https=) |
| MA (1) | MA29148B1 (https=) |
| NI (1) | NI200700161A (https=) |
| NO (1) | NO20073766L (https=) |
| NZ (1) | NZ555721A (https=) |
| PA (1) | PA8658301A1 (https=) |
| PE (1) | PE20060949A1 (https=) |
| TN (1) | TNSN07236A1 (https=) |
| TW (1) | TW200635904A (https=) |
| WO (1) | WO2006069242A2 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013503161A (ja) * | 2009-08-28 | 2013-01-31 | アリーナ ファーマシューティカルズ， インコーポレイテッド | カンナビノイド受容体モジュレーター |
| JP2014507445A (ja) * | 2011-02-25 | 2014-03-27 | アリーナ ファーマシューティカルズ， インコーポレイテッド | カンナビノイド受容体モジュレーター |
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| PE20050483A1 (es) | 2003-10-31 | 2005-08-25 | Arena Pharm Inc | Derivados de tetrazol de formula (i), sus composiciones farmaceuticas y procesos para producir composiciones farmaceuticas |
| DE602004022864D1 (de) | 2003-11-21 | 2009-10-08 | Arena Pharm Inc | 4-oxo-4,5-dihydro-furan-2-carbonsäure und derivate und verfahren zur behandlung von stoffwechselerkrankungen mit diesen verbindungen |
| PE20060949A1 (es) * | 2004-12-23 | 2006-10-11 | Arena Pharm Inc | Derivados fusionados de pirazol como agonistas del receptor de niacina |
| 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. |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| 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 |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| US9458136B2 (en) | 2011-02-25 | 2016-10-04 | Arena Pharmaceuticals, Inc. | Crystalline forms and processes for the preparation of cannabinoid receptor modulators |
| WO2012116278A1 (en) * | 2011-02-25 | 2012-08-30 | Arena Pharmaceuticals, Inc. | Cannabinoid receptor modulators |
| US9597340B2 (en) | 2011-02-25 | 2017-03-21 | 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 |
| EP2683705B1 (de) | 2011-03-08 | 2015-04-22 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes 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 |
| 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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| EP3621619B1 (en) | 2017-05-08 | 2023-06-28 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of visceral pain |
| KR102919209B1 (ko) | 2018-08-10 | 2026-01-28 | 다이아핀 테라퓨틱스, 엘엘씨 | 트리-펩타이드 그리고 대사, 심장혈관 및 염증성 장애의 치료 |
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| KR20040044856A (ko) | 2001-09-07 | 2004-05-31 | 오노 야꾸힝 고교 가부시키가이샤 | 인돌 유도체 화합물 |
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- 2005-12-20 GT GT200500379A patent/GT200500379A/es unknown
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- 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
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2006
- 2006-11-17 US US11/601,184 patent/US7612106B2/en not_active Expired - Fee Related
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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
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013503161A (ja) * | 2009-08-28 | 2013-01-31 | アリーナ ファーマシューティカルズ， インコーポレイテッド | カンナビノイド受容体モジュレーター |
| JP2022009408A (ja) * | 2009-08-28 | 2022-01-14 | アリーナ ファーマシューティカルズ， インコーポレイテッド | カンナビノイド受容体モジュレーター |
| JP2014507445A (ja) * | 2011-02-25 | 2014-03-27 | アリーナ ファーマシューティカルズ， インコーポレイテッド | カンナビノイド受容体モジュレーター |
| JP2022066289A (ja) * | 2011-02-25 | 2022-04-28 | アリーナ ファーマシューティカルズ， インコーポレイテッド | カンナビノイド受容体モジュレーター |
Also Published As
| Publication number | Publication date |
|---|---|
| US20090258892A1 (en) | 2009-10-15 |
| CA2589648A1 (en) | 2006-06-29 |
| GEP20105126B (en) | 2010-12-10 |
| CU23691B7 (es) | 2011-09-21 |
| KR20070088808A (ko) | 2007-08-29 |
| US20060205955A1 (en) | 2006-09-14 |
| GT200500379A (es) | 2006-10-25 |
| US20070073062A1 (en) | 2007-03-29 |
| BRPI0519262A2 (pt) | 2009-01-06 |
| US7612106B2 (en) | 2009-11-03 |
| AR055015A1 (es) | 2007-08-01 |
| WO2006069242A2 (en) | 2006-06-29 |
| EA013184B1 (ru) | 2010-02-26 |
| PE20060949A1 (es) | 2006-10-11 |
| PA8658301A1 (es) | 2006-10-13 |
| US7241792B2 (en) | 2007-07-10 |
| AU2005319121A1 (en) | 2006-06-29 |
| IL183654A0 (en) | 2007-09-20 |
| TNSN07236A1 (en) | 2008-11-21 |
| EA200701361A1 (ru) | 2007-12-28 |
| WO2006069242A3 (en) | 2006-08-31 |
| NO20073766L (no) | 2007-09-21 |
| CN102311378A (zh) | 2012-01-11 |
| CU20070144A7 (es) | 2010-01-22 |
| EP1831178A2 (en) | 2007-09-12 |
| NZ555721A (en) | 2011-02-25 |
| TW200635904A (en) | 2006-10-16 |
| HN2005036256A (es) | 2010-02-08 |
| CN102321024A (zh) | 2012-01-18 |
| NI200700161A (es) | 2008-04-21 |
| MA29148B1 (fr) | 2008-01-02 |
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