BRPI0719122A2 - Compostos orgânicos - Google Patents
Compostos orgânicos Download PDFInfo
- Publication number
- BRPI0719122A2 BRPI0719122A2 BRPI0719122-7A BRPI0719122A BRPI0719122A2 BR PI0719122 A2 BRPI0719122 A2 BR PI0719122A2 BR PI0719122 A BRPI0719122 A BR PI0719122A BR PI0719122 A2 BRPI0719122 A2 BR PI0719122A2
- Authority
- BR
- Brazil
- Prior art keywords
- methyl
- carboxylic acid
- pyrazol
- thiazole
- alkyl
- Prior art date
Links
- 150000002894 organic compounds Chemical class 0.000 title description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 110
- 108010087894 Fatty acid desaturases Proteins 0.000 claims abstract description 88
- 238000000034 method Methods 0.000 claims abstract description 75
- 230000000694 effects Effects 0.000 claims abstract description 48
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 33
- 102000016553 Stearoyl-CoA Desaturase Human genes 0.000 claims abstract 5
- 150000001875 compounds Chemical class 0.000 claims description 283
- -1 trifluoromethoxyl Chemical group 0.000 claims description 181
- 125000000217 alkyl group Chemical group 0.000 claims description 171
- 125000003118 aryl group Chemical group 0.000 claims description 145
- 239000002253 acid Substances 0.000 claims description 117
- 125000001072 heteroaryl group Chemical group 0.000 claims description 112
- 239000001257 hydrogen Substances 0.000 claims description 111
- 229910052739 hydrogen Inorganic materials 0.000 claims description 111
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 103
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 99
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 97
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 96
- 201000010099 disease Diseases 0.000 claims description 72
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 59
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 claims description 59
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 57
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 57
- JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 claims description 50
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 47
- 125000002947 alkylene group Chemical group 0.000 claims description 45
- 125000000304 alkynyl group Chemical group 0.000 claims description 39
- 125000001188 haloalkyl group Chemical group 0.000 claims description 39
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 38
- 230000001404 mediated effect Effects 0.000 claims description 35
- 125000003342 alkenyl group Chemical group 0.000 claims description 34
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 32
- IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 claims description 29
- 208000035475 disorder Diseases 0.000 claims description 25
- 125000004450 alkenylene group Chemical group 0.000 claims description 24
- 239000003112 inhibitor Substances 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
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- 239000000651 prodrug Substances 0.000 claims description 20
- 125000004419 alkynylene group Chemical group 0.000 claims description 19
- 241000124008 Mammalia Species 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 14
- 208000008589 Obesity Diseases 0.000 claims description 14
- 235000020824 obesity Nutrition 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- MBALKBRJRNEXCS-UHFFFAOYSA-N n-benzyl-4-methyl-2-(1h-pyrazol-5-yl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2NN=CC=2)SC=1C(=O)NCC1=CC=CC=C1 MBALKBRJRNEXCS-UHFFFAOYSA-N 0.000 claims description 12
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 230000005764 inhibitory process Effects 0.000 claims description 11
- YZVFSQQHQPPKNX-UHFFFAOYSA-N 1,3-thiazole-5-carboxylic acid Chemical compound OC(=O)C1=CN=CS1 YZVFSQQHQPPKNX-UHFFFAOYSA-N 0.000 claims description 10
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 10
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- 239000003937 drug carrier Substances 0.000 claims description 10
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- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 7
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims description 6
- 206010022489 Insulin Resistance Diseases 0.000 claims description 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 5
- 101000631826 Homo sapiens Stearoyl-CoA desaturase Proteins 0.000 claims description 5
- 102000055981 human SCD1 Human genes 0.000 claims description 5
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- OQFBNFVTGUSVEQ-UHFFFAOYSA-N 2-[1-[2-(4-fluorophenyl)ethyl]pyrazol-3-yl]-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(O)=O)=C(C)N=C1C1=NN(CCC=2C=CC(F)=CC=2)C=C1 OQFBNFVTGUSVEQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 4
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 4
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 4
- 230000037396 body weight Effects 0.000 claims description 4
- RRLZEMBDKSCPJD-UHFFFAOYSA-N n-benzyl-2-(5-bromopyrazin-2-yl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=CC(Br)=NC=2)SC=1C(=O)NCC1=CC=CC=C1 RRLZEMBDKSCPJD-UHFFFAOYSA-N 0.000 claims description 4
- OHNWRCKCGSXMOS-UHFFFAOYSA-N n-benzyl-2-(6-chloropyrazin-2-yl)-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2N=C(Cl)C=NC=2)SC=1C(=O)NCC1=CC=CC=C1 OHNWRCKCGSXMOS-UHFFFAOYSA-N 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
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- COFXNWIKPNAICQ-UHFFFAOYSA-N 2-[1-(2-anilinoethyl)pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCNC=3C=CC=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 COFXNWIKPNAICQ-UHFFFAOYSA-N 0.000 claims description 2
- NVNBSOWRMZEZCP-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CC=3C=CC(Cl)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 NVNBSOWRMZEZCP-UHFFFAOYSA-N 0.000 claims description 2
- UNFYXLDSTKSWOV-UHFFFAOYSA-N 2-[1-[(4-ethylphenyl)methyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound C1=CC(CC)=CC=C1CN1N=C(C=2SC(=C(C)N=2)C(=O)NCC=2C=NC=CC=2)C=C1 UNFYXLDSTKSWOV-UHFFFAOYSA-N 0.000 claims description 2
- QTKLPOWQQUEGNX-UHFFFAOYSA-N 2-[1-[2-[(4-fluorobenzoyl)amino]ethyl]pyrazol-3-yl]-4-methyl-n-(pyridin-3-ylmethyl)-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C2=NN(CCNC(=O)C=3C=CC(F)=CC=3)C=C2)SC=1C(=O)NCC1=CC=CN=C1 QTKLPOWQQUEGNX-UHFFFAOYSA-N 0.000 claims description 2
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- LFQXILYITNIVCS-UHFFFAOYSA-N 2-[6-[[4-(difluoromethoxy)phenyl]methyl-methylamino]pyrazin-2-yl]-n-[(4-fluorophenyl)methyl]-4-methyl-1,3-thiazole-5-carboxamide Chemical compound C=1N=CC(C=2SC(=C(C)N=2)C(=O)NCC=2C=CC(F)=CC=2)=NC=1N(C)CC1=CC=C(OC(F)F)C=C1 LFQXILYITNIVCS-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
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- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Nutrition Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82342506P | 2006-08-24 | 2006-08-24 | |
| US60/823,425 | 2006-08-24 | ||
| PCT/US2007/018554 WO2008024390A2 (en) | 2006-08-24 | 2007-08-22 | 2- (pyrazin-2-yl) -thiazole and 2- (1h-pyraz0l-3-yl) -thiazole derivatives as well as related compounds as stearoyl-coa desaturase (scd) inhibitors for the treatment of metabolic, cardiovascular and other disorders |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0719122A2 true BRPI0719122A2 (pt) | 2013-12-10 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0719122-7A BRPI0719122A2 (pt) | 2006-08-24 | 2007-08-22 | Compostos orgânicos |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8314138B2 (enExample) |
| EP (1) | EP2086970B1 (enExample) |
| JP (1) | JP2010501567A (enExample) |
| KR (1) | KR20090040478A (enExample) |
| CN (1) | CN101506203B (enExample) |
| AU (1) | AU2007288245A1 (enExample) |
| BR (1) | BRPI0719122A2 (enExample) |
| CA (1) | CA2661017A1 (enExample) |
| MX (1) | MX2009002019A (enExample) |
| RU (1) | RU2009110254A (enExample) |
| WO (1) | WO2008024390A2 (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2008127349A2 (en) | 2006-08-15 | 2008-10-23 | Novartis Ag | Heterocyclic compounds suitable for the treatment of diseases related to elevated lipid level |
| EP2121671A1 (en) * | 2006-12-20 | 2009-11-25 | Novartis AG | 2-substituted 5-membered heterocycles as scd inhibitors |
| CA2683948A1 (en) * | 2007-04-20 | 2008-10-30 | Merck Frosst Canada Ltd. | Novel heteroaromatic compounds as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| WO2009073973A1 (en) * | 2007-12-11 | 2009-06-18 | Merck Frosst Canada Ltd. | Novel heteroaromatic compounds as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| KR101584826B1 (ko) * | 2008-02-20 | 2016-01-18 | 노파르티스 아게 | 스테아로일-ＣｏＡ 데새투라제의 헤테로시클릭 억제제 |
| GB0810913D0 (en) * | 2008-06-13 | 2008-07-23 | Smithkline Beecham Corp | Comppounds |
| US20110184027A1 (en) * | 2008-09-25 | 2011-07-28 | Glenmark Pharmaceuticals S.A. | Tissue selective stearoyl-coa desaturase 1 inhibitors and cell based screening assay for their identification |
| DE102009041242A1 (de) | 2009-09-11 | 2011-12-15 | Bayer Schering Pharma Aktiengesellschaft | Heterocyclisch substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102008057364A1 (de) | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102008057344A1 (de) | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | Aminoalkyl-substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102009041241A1 (de) | 2009-09-11 | 2011-08-04 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102008057343A1 (de) | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | Heterocyclisch substituierte Aryl-Verbindungen und ihre Verwendung |
| FR2938538B1 (fr) * | 2008-11-17 | 2011-08-05 | Univ Nice Sophia Antipolis | Procede de preparation d'acides et d'esters boroniques en presence de magnesium metallique |
| WO2010094120A1 (en) | 2009-02-17 | 2010-08-26 | Merck Frosst Canada Ltd. | Novel spiro compounds useful as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| WO2011011872A1 (en) | 2009-07-28 | 2011-02-03 | Merck Frosst Canada Ltd. | Novel spiro compounds useful as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| EP2483264A1 (en) * | 2009-10-01 | 2012-08-08 | Novartis AG | Pyrazole derivatives which modulate stearoyl-coa desaturase |
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- 2007-08-22 RU RU2009110254/04A patent/RU2009110254A/ru not_active Application Discontinuation
- 2007-08-22 KR KR1020097005864A patent/KR20090040478A/ko not_active Withdrawn
- 2007-08-22 EP EP07811474.1A patent/EP2086970B1/en not_active Not-in-force
- 2007-08-22 MX MX2009002019A patent/MX2009002019A/es not_active Application Discontinuation
- 2007-08-22 WO PCT/US2007/018554 patent/WO2008024390A2/en not_active Ceased
- 2007-08-22 CA CA002661017A patent/CA2661017A1/en not_active Abandoned
- 2007-08-22 US US12/438,654 patent/US8314138B2/en not_active Expired - Fee Related
- 2007-08-22 CN CN200780031571XA patent/CN101506203B/zh not_active Expired - Fee Related
- 2007-08-22 BR BRPI0719122-7A patent/BRPI0719122A2/pt not_active Application Discontinuation
- 2007-08-22 AU AU2007288245A patent/AU2007288245A1/en not_active Abandoned
- 2007-08-22 JP JP2009525617A patent/JP2010501567A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP2086970B1 (en) | 2014-02-26 |
| CA2661017A1 (en) | 2008-02-28 |
| US8314138B2 (en) | 2012-11-20 |
| WO2008024390A3 (en) | 2008-04-17 |
| MX2009002019A (es) | 2009-03-09 |
| JP2010501567A (ja) | 2010-01-21 |
| CN101506203B (zh) | 2013-10-16 |
| KR20090040478A (ko) | 2009-04-24 |
| RU2009110254A (ru) | 2010-09-27 |
| WO2008024390A2 (en) | 2008-02-28 |
| US20100239520A1 (en) | 2010-09-23 |
| EP2086970A2 (en) | 2009-08-12 |
| CN101506203A (zh) | 2009-08-12 |
| AU2007288245A1 (en) | 2008-02-28 |
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