JP2007532651A5 - - Google Patents
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- Publication number
- JP2007532651A5 JP2007532651A5 JP2007508428A JP2007508428A JP2007532651A5 JP 2007532651 A5 JP2007532651 A5 JP 2007532651A5 JP 2007508428 A JP2007508428 A JP 2007508428A JP 2007508428 A JP2007508428 A JP 2007508428A JP 2007532651 A5 JP2007532651 A5 JP 2007532651A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- substituted
- cycloalkyl
- halogen
- 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.)
- Granted
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- 229910052736 halogen Inorganic materials 0.000 claims 45
- 150000002367 halogens Chemical class 0.000 claims 43
- 150000001875 compounds Chemical class 0.000 claims 29
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 15
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 125000004076 pyridyl group Chemical group 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- 239000003112 inhibitor Substances 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 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 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims 3
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 125000001041 indolyl group Chemical group 0.000 claims 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 125000005493 quinolyl group Chemical group 0.000 claims 3
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 2
- -1 1-oxidepyridinyl Chemical group 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 claims 2
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 claims 2
- 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 2
- 102000004877 Insulin Human genes 0.000 claims 2
- 108090001061 Insulin Proteins 0.000 claims 2
- 102100031545 Microsomal triglyceride transfer protein large subunit Human genes 0.000 claims 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
- 102000002072 Non-Receptor Type 1 Protein Tyrosine Phosphatase Human genes 0.000 claims 2
- 108010015847 Non-Receptor Type 1 Protein Tyrosine Phosphatase Proteins 0.000 claims 2
- 102000023984 PPAR alpha Human genes 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 229940125396 insulin Drugs 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 108010038232 microsomal triglyceride transfer protein Proteins 0.000 claims 2
- 229960003512 nicotinic acid Drugs 0.000 claims 2
- 235000001968 nicotinic acid Nutrition 0.000 claims 2
- 239000011664 nicotinic acid Substances 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims 1
- 102000018616 Apolipoproteins B Human genes 0.000 claims 1
- 108010027006 Apolipoproteins B Proteins 0.000 claims 1
- 229940123208 Biguanide Drugs 0.000 claims 1
- 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 claims 1
- 229940122904 Glucagon receptor antagonist Drugs 0.000 claims 1
- 108010023302 HDL Cholesterol Proteins 0.000 claims 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- 229940110346 PPAR gamma partial agonist Drugs 0.000 claims 1
- 229940122054 Peroxisome proliferator-activated receptor delta agonist Drugs 0.000 claims 1
- 229940080774 Peroxisome proliferator-activated receptor gamma agonist Drugs 0.000 claims 1
- 102000013566 Plasminogen Human genes 0.000 claims 1
- 108010051456 Plasminogen Proteins 0.000 claims 1
- 102100040918 Pro-glucagon Human genes 0.000 claims 1
- 102000001494 Sterol O-Acyltransferase Human genes 0.000 claims 1
- 108010054082 Sterol O-acyltransferase Proteins 0.000 claims 1
- 229940100389 Sulfonylurea Drugs 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 230000003579 anti-obesity Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 150000004283 biguanides Chemical class 0.000 claims 1
- 229920000080 bile acid sequestrant Polymers 0.000 claims 1
- 230000001906 cholesterol absorption Effects 0.000 claims 1
- 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 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229940125542 dual agonist Drugs 0.000 claims 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
- 229940121380 ileal bile acid transporter inhibitor Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229960003966 nicotinamide Drugs 0.000 claims 1
- 235000005152 nicotinamide Nutrition 0.000 claims 1
- 239000011570 nicotinamide Substances 0.000 claims 1
- 229960004738 nicotinyl alcohol Drugs 0.000 claims 1
- 239000004031 partial agonist Substances 0.000 claims 1
- 239000002530 phenolic antioxidant Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 claims 1
- 229960003912 probucol Drugs 0.000 claims 1
- 230000028327 secretion Effects 0.000 claims 1
- 235000002639 sodium chloride Nutrition 0.000 claims 1
- 0 C*(**)NCC1=CC=CC(C)(*)C=C1[Al] Chemical compound C*(**)NCC1=CC=CC(C)(*)C=C1[Al] 0.000 description 32
- UJCFZCTTZWHRNL-UHFFFAOYSA-N Cc(cc1)cc(C)c1OC Chemical compound Cc(cc1)cc(C)c1OC UJCFZCTTZWHRNL-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N Cc1c(C)cccc1 Chemical compound Cc1c(C)cccc1 CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- GWHJZXXIDMPWGX-UHFFFAOYSA-N Cc1cc(C)c(C)cc1 Chemical compound Cc1cc(C)c(C)cc1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 2
- FZCZSYJDBMEHIV-UHFFFAOYSA-N CC(C(F)(F)F)(c(cc1)cc(-c2ccc(C(F)(F)F)cc2CN(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)C(OC)=O)c1OC)O Chemical compound CC(C(F)(F)F)(c(cc1)cc(-c2ccc(C(F)(F)F)cc2CN(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)C(OC)=O)c1OC)O FZCZSYJDBMEHIV-UHFFFAOYSA-N 0.000 description 1
- ZHFZHPCAJKWAAY-UHFFFAOYSA-N CC(C(F)(F)F)c(cc1)cc(-c2ccc(C(F)(F)F)cc2CN(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)C(OC)=O)c1OC Chemical compound CC(C(F)(F)F)c(cc1)cc(-c2ccc(C(F)(F)F)cc2CN(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)C(OC)=O)c1OC ZHFZHPCAJKWAAY-UHFFFAOYSA-N 0.000 description 1
- IPERTFJAVPQRGJ-RMKNXTFCSA-N CC(C)=C(C)/C=C(/C(F)(F)F)\C=C Chemical compound CC(C)=C(C)/C=C(/C(F)(F)F)\C=C IPERTFJAVPQRGJ-RMKNXTFCSA-N 0.000 description 1
- YHVUGDRAEMKWCE-UHFFFAOYSA-N CC(C)C(C=C1c(cc2)c(CN(Cc3cc(C(F)(F)F)cc(C(F)(F)F)c3)C(OC)=O)cc2-c2cnccc2)=CCC1OC Chemical compound CC(C)C(C=C1c(cc2)c(CN(Cc3cc(C(F)(F)F)cc(C(F)(F)F)c3)C(OC)=O)cc2-c2cnccc2)=CCC1OC YHVUGDRAEMKWCE-UHFFFAOYSA-N 0.000 description 1
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- QMDMWGKKJUHPCO-UHFFFAOYSA-N CC(C)c(cc1)cc(-c(c(CN(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)C(OC)=O)c2)ccc2N)c1OC Chemical compound CC(C)c(cc1)cc(-c(c(CN(Cc2cc(C(F)(F)F)cc(C(F)(F)F)c2)C(OC)=O)c2)ccc2N)c1OC QMDMWGKKJUHPCO-UHFFFAOYSA-N 0.000 description 1
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- NHDGGTJXXOAYKR-UHFFFAOYSA-N CC(C)c(cc1)cc(-c2ccc(C(F)(F)F)cc2CN(Cc2cc(NS(C)(=O)=O)cc(C(F)(F)F)c2)C(OC)=O)c1OC Chemical compound CC(C)c(cc1)cc(-c2ccc(C(F)(F)F)cc2CN(Cc2cc(NS(C)(=O)=O)cc(C(F)(F)F)c2)C(OC)=O)c1OC NHDGGTJXXOAYKR-UHFFFAOYSA-N 0.000 description 1
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| US9663534B2 (en) | 2013-12-17 | 2017-05-30 | Merck Sharp & Dohme Corp. | Fused bicyclic isoxazolines as inhibitors of cholesterol ester transfer protein |
| EP3174537B1 (en) | 2014-07-29 | 2021-06-23 | Merck Sharp & Dohme Corp. | Monocyclic isoxazolines as inhibitors of cholesterol ester transfer protein |
| BR112022008131A2 (pt) | 2019-11-01 | 2022-07-19 | Syngenta Crop Protection Ag | Compostos heteroaromáticos bicíclicos fundidos pesticidamente ativos |
| CN110639018B (zh) * | 2019-11-14 | 2020-06-26 | 牡丹江医学院 | 一种防治老年性高血压的药物组合物及其用途 |
| US20240294517A1 (en) | 2021-06-24 | 2024-09-05 | Syngenta Crop Protection Ag | 2-[3-[1 [(quinazolin-4-yl)amino]ethyl]pyrazin-2-yl]thiazole-5-carbonitrile derivatives and similar compounds as pesticides |
| WO2023247360A1 (en) | 2022-06-21 | 2023-12-28 | Syngenta Crop Protection Ag | Pesticidally active fused bicyclic heteroaromatic compounds |
| WO2024110554A1 (en) | 2022-11-23 | 2024-05-30 | Syngenta Crop Protection Ag | N-[(1 -[2-[6-(pyridazin-3-yl]-1,2,4-triazol-3-yl]ethyl]-quinazolin-4-amine and n-[1-[3-(6-(pyridazin-3-yl)pyrazin-2-yl]ethyl]-8-quinazolin-4-amine derivatives as pesticides |
| WO2025022008A1 (en) | 2023-07-27 | 2025-01-30 | Syngenta Crop Protection Ag | Pesticidally active quinazoline compounds |
| WO2025022007A1 (en) | 2023-07-27 | 2025-01-30 | Syngenta Crop Protection Ag | Pesticidally active quinazoline compounds |
| WO2025132349A1 (en) | 2023-12-19 | 2025-06-26 | Syngenta Crop Protection Ag | Pesticidally active quinazoline compounds |
| WO2025132754A1 (en) | 2023-12-21 | 2025-06-26 | Syngenta Crop Protection Ag | Pesticidally active quinazoline compounds |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002525350A (ja) * | 1998-09-25 | 2002-08-13 | モンサント カンパニー | コレステロールエステル輸送タンパク質活性阻害に有効な置換されたｎ−脂肪族−ｎ−芳香族第三級ヘテロアルキルアミン |
| EP1115695B1 (en) * | 1998-09-25 | 2005-06-01 | Monsanto Company | (r)-chiral halogenated 1-substitutedamino-(n+1)-alkanols useful for inhibiting cholesteryl ester transfer protein activity |
| CO5271716A1 (es) * | 1999-11-30 | 2003-04-30 | Pfizer Prod Inc | Cristales de 4- carboxamino 1,2,3,4-tetrahidroquinolina 2- sustituida |
| DZ3409A1 (fr) * | 2000-08-15 | 2002-02-21 | Pfizer Prod Inc | Association therapeuthique |
| US6627767B2 (en) * | 2000-08-29 | 2003-09-30 | Abbott Laboratories | Amino(oxo) acetic acid protein tyrosine phosphatase inhibitors |
| JP2003221376A (ja) * | 2001-11-21 | 2003-08-05 | Japan Tobacco Inc | Ｃｅｔｐ活性阻害剤 |
| EP1470102B1 (en) * | 2002-01-29 | 2011-05-25 | Merck Serono SA | Substituted methylene amide derivatives as modulators of protein tyrosine phosphatases (ptps) |
| SI1533292T1 (sl) | 2002-08-30 | 2007-08-31 | Japan Tobacco Inc | Dibenzilaminska spojina in njena medicinska uporaba |
| EP1616862A4 (en) * | 2003-04-18 | 2008-07-16 | Ono Pharmaceutical Co | HETEROCYCLIC NITROGEN COMPOUND AND USE THEREOF |
-
2005
- 2005-04-08 JP JP2007508428A patent/JP4922924B2/ja not_active Expired - Fee Related
- 2005-04-08 US US11/578,694 patent/US7737295B2/en active Active
- 2005-04-08 CA CA2562082A patent/CA2562082C/en not_active Expired - Fee Related
- 2005-04-08 WO PCT/US2005/012196 patent/WO2005100298A1/en not_active Ceased
- 2005-04-08 AU AU2005233160A patent/AU2005233160B2/en not_active Ceased
- 2005-04-08 CN CNA2005800110706A patent/CN1942428A/zh active Pending
- 2005-04-08 EP EP05736159.4A patent/EP1737811B1/en not_active Expired - Lifetime
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