JP2008519080A5 - - Google Patents
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- Publication number
- JP2008519080A5 JP2008519080A5 JP2007540384A JP2007540384A JP2008519080A5 JP 2008519080 A5 JP2008519080 A5 JP 2008519080A5 JP 2007540384 A JP2007540384 A JP 2007540384A JP 2007540384 A JP2007540384 A JP 2007540384A JP 2008519080 A5 JP2008519080 A5 JP 2008519080A5
- Authority
- JP
- Japan
- Prior art keywords
- niacin
- analog
- composition
- tetrazol
- pyrazole
- 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.)
- Pending
Links
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 26
- 150000006636 nicotinic acid Chemical class 0.000 claims 26
- 229960003512 nicotinic acid Drugs 0.000 claims 26
- 235000001968 nicotinic acid Nutrition 0.000 claims 26
- 239000011664 nicotinic acid Substances 0.000 claims 26
- 108700010041 Nicotinic acid receptor Proteins 0.000 claims 16
- 239000004031 partial agonist Substances 0.000 claims 16
- 238000011010 flushing procedure Methods 0.000 claims 14
- 150000002632 lipids Chemical class 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 6
- LTQYSJKGRPGMPO-UHFFFAOYSA-N 3-(2h-tetrazol-5-yl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazole Chemical compound C1=2CCCC=2NN=C1C1=NN=NN1 LTQYSJKGRPGMPO-UHFFFAOYSA-N 0.000 claims 3
- PWTAIWVYJBIWDV-UHFFFAOYSA-N 3-(2h-tetrazol-5-yl)-1,4-dihydrocyclopenta[c]pyrazole Chemical compound C1=2CC=CC=2NN=C1C=1N=NNN=1 PWTAIWVYJBIWDV-UHFFFAOYSA-N 0.000 claims 3
- SWSJDJYGSQGAFF-UHFFFAOYSA-N 3-(2h-tetrazol-5-yl)-1,6-dihydrocyclopenta[c]pyrazole Chemical compound C1C=CC2=C1NN=C2C1=NN=NN1 SWSJDJYGSQGAFF-UHFFFAOYSA-N 0.000 claims 3
- FTXOPGWMJLXSRU-UHFFFAOYSA-N 3-(2h-tetrazol-5-yl)-4,6-dihydro-1h-furo[3,4-c]pyrazole Chemical compound C1OCC=2C1=NNC=2C1=NN=NN1 FTXOPGWMJLXSRU-UHFFFAOYSA-N 0.000 claims 3
- CXBPIKBDSFXEMF-UHFFFAOYSA-N 3-(2h-tetrazol-5-yl)-4,6-dihydro-1h-thieno[3,4-c]pyrazole Chemical compound C1SCC=2C1=NNC=2C1=NN=NN1 CXBPIKBDSFXEMF-UHFFFAOYSA-N 0.000 claims 3
- 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 claims 3
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 3
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 3
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 3
- HEPHDXKADNILNS-UHFFFAOYSA-N 5-(5-propan-2-yl-1h-pyrazol-3-yl)-2h-tetrazole Chemical compound N1C(C(C)C)=CC(C=2NN=NN=2)=N1 HEPHDXKADNILNS-UHFFFAOYSA-N 0.000 claims 3
- VYGUDGUPIFVQNE-UHFFFAOYSA-N 5-[(3-bromophenyl)methyl]-1h-pyrazole-3-carboxylic acid Chemical compound N1N=C(C(=O)O)C=C1CC1=CC=CC(Br)=C1 VYGUDGUPIFVQNE-UHFFFAOYSA-N 0.000 claims 3
- UYMDSFKYOCEPFN-UHFFFAOYSA-N 5-[(3-chlorophenyl)methyl]-1h-pyrazole-3-carboxylic acid Chemical compound N1N=C(C(=O)O)C=C1CC1=CC=CC(Cl)=C1 UYMDSFKYOCEPFN-UHFFFAOYSA-N 0.000 claims 3
- DWGHGHIWIZJJKX-UHFFFAOYSA-N 5-[(3-fluorophenyl)methyl]-1h-pyrazole-3-carboxylic acid Chemical compound N1C(C(=O)O)=CC(CC=2C=C(F)C=CC=2)=N1 DWGHGHIWIZJJKX-UHFFFAOYSA-N 0.000 claims 3
- SECXDPVXDUGTCU-UHFFFAOYSA-N 5-ethyl-3-(2h-tetrazol-5-yl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazole Chemical compound C=12CC(CC)CC2=NNC=1C1=NN=NN1 SECXDPVXDUGTCU-UHFFFAOYSA-N 0.000 claims 3
- QFLSWJUOMICBKB-UHFFFAOYSA-N 6-methyl-3-(2h-tetrazol-5-yl)-4,6-dihydro-1h-furo[3,4-c]pyrazole Chemical compound CC1OCC=2C1=NNC=2C1=NN=NN1 QFLSWJUOMICBKB-UHFFFAOYSA-N 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 3
- 239000003623 enhancer Substances 0.000 claims 2
- 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
- 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
- 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
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- 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
- 239000003288 aldose reductase inhibitor Substances 0.000 claims 1
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 230000001925 catabolic effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 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
- 229940125753 fibrate Drugs 0.000 claims 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000003914 insulin secretion Effects 0.000 claims 1
- GZQKNULLWNGMCW-PWQABINMSA-N lipid A (E. coli) Chemical compound O1[C@H](CO)[C@@H](OP(O)(O)=O)[C@H](OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H]1OC[C@@H]1[C@@H](O)[C@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OP(O)(O)=O)O1 GZQKNULLWNGMCW-PWQABINMSA-N 0.000 claims 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 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
- 150000001467 thiazolidinediones Chemical class 0.000 claims 1
- AWYMFBJJKFTCFO-UHFFFAOYSA-N C(C1)C2C1CCC2 Chemical compound C(C1)C2C1CCC2 AWYMFBJJKFTCFO-UHFFFAOYSA-N 0.000 description 1
- 0 Cc1c(*)[n]nc1* Chemical compound Cc1c(*)[n]nc1* 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62553604P | 2004-11-05 | 2004-11-05 | |
| PCT/US2005/039560 WO2006052569A1 (en) | 2004-11-05 | 2005-11-01 | Compositions for treating flushing and lipid-associated disorders comprising niacin receptor partial agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008519080A JP2008519080A (ja) | 2008-06-05 |
| JP2008519080A5 true JP2008519080A5 (https=) | 2008-12-25 |
Family
ID=36046632
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007540384A Pending JP2008519080A (ja) | 2004-11-05 | 2005-11-01 | ナイアシン受容体部分的アゴニストを含む、潮紅および脂質関連障害を処置するための組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20080139628A1 (https=) |
| EP (1) | EP1811996A1 (https=) |
| JP (1) | JP2008519080A (https=) |
| CN (1) | CN101076331A (https=) |
| AU (1) | AU2005305086A1 (https=) |
| CA (1) | CA2584225A1 (https=) |
| WO (1) | WO2006052569A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| PL364348A1 (en) | 2004-01-12 | 2005-07-25 | PHARMENA Sp.z o.o. | Application of quaternary pyridine salts as vessel protection agent |
| AU2006329564A1 (en) | 2005-07-11 | 2007-07-05 | Pharmena North America Inc. | Formulations for treatment of lipoprotein abnormalities comprising a statin a statin and a methylnicotinamide derivative |
| US20100204278A1 (en) * | 2006-10-20 | 2010-08-12 | Beresis Richard T | Niacin Receptor Agonists, Compositions Containing Such Compounds and Methods of Treatment |
| CN102149680B (zh) | 2008-07-08 | 2014-12-10 | 第一三共株式会社 | 含氮芳族杂环化合物 |
| JP5925771B2 (ja) | 2010-06-24 | 2016-05-25 | トラスティーズ オブ タフツ カレッジ | ナイアシン模倣体、およびその使用方法 |
| WO2011163612A1 (en) * | 2010-06-24 | 2011-12-29 | Trustees Of Tufts College | Niacin mimetics, and methods of use thereof |
| CN103755637A (zh) * | 2013-12-26 | 2014-04-30 | 平湖优康药物研发有限公司 | 一种医药中间体1,4,5,6-四氢-3-环戊并吡唑甲腈的合成工艺 |
| US9456982B2 (en) | 2014-05-18 | 2016-10-04 | Be-Warm Llc | Solid formulations of niacin to counteract cold extremities |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5126145A (en) * | 1989-04-13 | 1992-06-30 | Upsher Smith Laboratories Inc | Controlled release tablet containing water soluble medicament |
| US5268181A (en) * | 1989-04-13 | 1993-12-07 | Upsher-Smith Laboratories, Inc. | Method of using niacin to control nocturnal cholesterol synthesis |
| AU5787996A (en) * | 1995-04-19 | 1996-11-07 | Lipoprotein Technologies, Inc. | Compositions, kits, and methods for administration of antilipemic and anti-platelet aggregation drugs |
| US6902902B2 (en) * | 2001-11-27 | 2005-06-07 | Arena Pharmaceuticals, Inc. | Human G protein-coupled receptors and modulators thereof for the treatment of metabolic-related disorders |
| EP1551403B1 (en) * | 2002-10-10 | 2009-04-29 | Arena Pharmaceuticals, Inc. | 5-substituted 2h-pyrazone-3-carboxylic acid derivatives as antilipolytic agents for the treatment of metabolic-related disorders such as dyslipidemia |
| 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 |
-
2005
- 2005-11-01 CN CNA2005800375213A patent/CN101076331A/zh active Pending
- 2005-11-01 WO PCT/US2005/039560 patent/WO2006052569A1/en not_active Ceased
- 2005-11-01 US US11/718,539 patent/US20080139628A1/en not_active Abandoned
- 2005-11-01 CA CA002584225A patent/CA2584225A1/en not_active Abandoned
- 2005-11-01 JP JP2007540384A patent/JP2008519080A/ja active Pending
- 2005-11-01 AU AU2005305086A patent/AU2005305086A1/en not_active Abandoned
- 2005-11-01 EP EP05816215A patent/EP1811996A1/en not_active Withdrawn
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