JP2011521907A5 - - Google Patents
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- JP2011521907A5 JP2011521907A5 JP2011507806A JP2011507806A JP2011521907A5 JP 2011521907 A5 JP2011521907 A5 JP 2011521907A5 JP 2011507806 A JP2011507806 A JP 2011507806A JP 2011507806 A JP2011507806 A JP 2011507806A JP 2011521907 A5 JP2011521907 A5 JP 2011521907A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- cycloalkyl
- piperidine
- carbonyl
- 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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- 238000000034 method Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims 13
- -1 4-ethoxycarbonyl-thiazol-2-yl Chemical group 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims 10
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 10
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- 125000001207 fluorophenyl group Chemical group 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 230000020477 pH reduction Effects 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 claims 2
- KIRRXZPLONWSFO-UHFFFAOYSA-N 2-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]-1,3-thiazole-4-carboxylic acid Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=NC(C(O)=O)=CS1 KIRRXZPLONWSFO-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- QJUCSOLFYRYWRC-UHFFFAOYSA-N CCOC(=O)C(=O)CSC(=N)C1CCN(CC1)C(=O)O Chemical compound CCOC(=O)C(=O)CSC(=N)C1CCN(CC1)C(=O)O QJUCSOLFYRYWRC-UHFFFAOYSA-N 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 1
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 238000007259 addition reaction Methods 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 230000009435 amidation Effects 0.000 claims 1
- 238000007112 amidation reaction Methods 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 230000021235 carbamoylation Effects 0.000 claims 1
- 230000021523 carboxylation Effects 0.000 claims 1
- 238000006473 carboxylation reaction Methods 0.000 claims 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims 1
- LBRUPXMVELEXIV-UHFFFAOYSA-N ethyl 2-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(C2CCN(CC2)C(=O)OC(C)(C)C)=N1 LBRUPXMVELEXIV-UHFFFAOYSA-N 0.000 claims 1
- VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 230000006103 sulfonylation Effects 0.000 claims 1
- 238000005694 sulfonylation reaction Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 1
- MLNWKJZNTDVLNG-UHFFFAOYSA-N tert-butyl 4-[c-(3-ethoxy-2,3-dioxopropyl)sulfanylcarbonimidoyl]piperidine-1-carboxylate Chemical compound CCOC(=O)C(=O)CSC(=N)C1CCN(C(=O)OC(C)(C)C)CC1 MLNWKJZNTDVLNG-UHFFFAOYSA-N 0.000 claims 1
- SCGQNJHAAYUQOO-UHFFFAOYSA-N tert-butyl 4-carbamothioylpiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(C(N)=S)CC1 SCGQNJHAAYUQOO-UHFFFAOYSA-N 0.000 claims 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims 1
- 150000007979 thiazole derivatives Chemical class 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
- 208000035475 disorder Diseases 0.000 description 11
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 9
- 206010022489 Insulin Resistance Diseases 0.000 description 8
- 150000001875 compounds Chemical class 0.000 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 description 8
- 239000003814 drug Substances 0.000 description 7
- 150000002632 lipids Chemical class 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- 201000001320 Atherosclerosis Diseases 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- 208000031226 Hyperlipidaemia Diseases 0.000 description 5
- 206010020772 Hypertension Diseases 0.000 description 5
- 208000001145 Metabolic Syndrome Diseases 0.000 description 5
- 208000008589 Obesity Diseases 0.000 description 5
- 206010033645 Pancreatitis Diseases 0.000 description 5
- 208000017442 Retinal disease Diseases 0.000 description 5
- 206010038923 Retinopathy Diseases 0.000 description 5
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 201000001421 hyperglycemia Diseases 0.000 description 5
- 208000017169 kidney disease Diseases 0.000 description 5
- 230000004770 neurodegeneration Effects 0.000 description 5
- 208000015122 neurodegenerative disease Diseases 0.000 description 5
- 201000001119 neuropathy Diseases 0.000 description 5
- 230000007823 neuropathy Effects 0.000 description 5
- 235000020824 obesity Nutrition 0.000 description 5
- 208000033808 peripheral neuropathy Diseases 0.000 description 5
- 208000037803 restenosis Diseases 0.000 description 5
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 5
- 230000002792 vascular Effects 0.000 description 5
- 208000004611 Abdominal Obesity Diseases 0.000 description 4
- 206010065941 Central obesity Diseases 0.000 description 4
- 208000032928 Dyslipidaemia Diseases 0.000 description 4
- 102000004877 Insulin Human genes 0.000 description 4
- 108090001061 Insulin Proteins 0.000 description 4
- 208000017170 Lipid metabolism disease Diseases 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- 208000006575 hypertriglyceridemia Diseases 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 229940125396 insulin Drugs 0.000 description 4
- 208000035150 Hypercholesterolemia Diseases 0.000 description 3
- 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 description 2
- 102100039994 Gastric inhibitory polypeptide Human genes 0.000 description 2
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 102000002072 Non-Receptor Type 1 Protein Tyrosine Phosphatase Human genes 0.000 description 2
- 108010015847 Non-Receptor Type 1 Protein Tyrosine Phosphatase Proteins 0.000 description 2
- 102000002808 Pituitary adenylate cyclase-activating polypeptide Human genes 0.000 description 2
- 108010004684 Pituitary adenylate cyclase-activating polypeptide Proteins 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000003862 glucocorticoid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 description 2
- MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 1
- 229940123324 Acyltransferase inhibitor Drugs 0.000 description 1
- 108010064733 Angiotensins Proteins 0.000 description 1
- 102000015427 Angiotensins Human genes 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- 208000019838 Blood disease Diseases 0.000 description 1
- 239000002083 C09CA01 - Losartan Substances 0.000 description 1
- 239000004072 C09CA03 - Valsartan Substances 0.000 description 1
- 239000002081 C09CA05 - Tasosartan Substances 0.000 description 1
- 239000005537 C09CA07 - Telmisartan Substances 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 208000028698 Cognitive impairment Diseases 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical class 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 description 1
- 229940089838 Glucagon-like peptide 1 receptor agonist Drugs 0.000 description 1
- 206010018429 Glucose tolerance impaired Diseases 0.000 description 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
- 229940122199 Insulin secretagogue Drugs 0.000 description 1
- 206010024229 Leprosy Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 102000023984 PPAR alpha Human genes 0.000 description 1
- 102000000536 PPAR gamma Human genes 0.000 description 1
- 108010016731 PPAR gamma Proteins 0.000 description 1
- 102000014743 Pituitary Adenylate Cyclase-Activating Polypeptide Receptors Human genes 0.000 description 1
- 108010064032 Pituitary Adenylate Cyclase-Activating Polypeptide Receptors Proteins 0.000 description 1
- 208000001280 Prediabetic State Diseases 0.000 description 1
- 102100040918 Pro-glucagon Human genes 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 102100028255 Renin Human genes 0.000 description 1
- 108090000783 Renin Proteins 0.000 description 1
- 102000001494 Sterol O-Acyltransferase Human genes 0.000 description 1
- 108010054082 Sterol O-acyltransferase Proteins 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000002404 acyltransferase inhibitor Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003579 anti-obesity Effects 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 230000001906 cholesterol absorption Effects 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 108010036598 gastric inhibitory polypeptide receptor Proteins 0.000 description 1
- 208000014951 hematologic disease Diseases 0.000 description 1
- 208000018706 hematopoietic system disease Diseases 0.000 description 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
- 229940121380 ileal bile acid transporter inhibitor Drugs 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229960004773 losartan Drugs 0.000 description 1
- KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960004738 nicotinyl alcohol Drugs 0.000 description 1
- 230000004963 pathophysiological condition Effects 0.000 description 1
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
- 201000009104 prediabetes syndrome Diseases 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229960000651 tasosartan Drugs 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- 229960005187 telmisartan Drugs 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 229960004699 valsartan Drugs 0.000 description 1
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08290424 | 2008-05-05 | ||
| EP08290424.4 | 2008-05-05 | ||
| PCT/EP2009/002607 WO2009135581A2 (en) | 2008-05-05 | 2009-04-08 | Novel nip thiazole derivatives as inhibitors of 11-beta-hydroxysteroid dehydrogenase-1 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011521907A JP2011521907A (ja) | 2011-07-28 |
| JP2011521907A5 true JP2011521907A5 (cg-RX-API-DMAC7.html) | 2012-06-28 |
| JP5735412B2 JP5735412B2 (ja) | 2015-06-17 |
Family
ID=40935480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011507806A Expired - Fee Related JP5735412B2 (ja) | 2008-05-05 | 2009-04-08 | １１−ベータ−ヒドロキシステロイドデヒドロゲナーゼ−１の阻害剤としてのｎｉｐチアゾール誘導体 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US8546575B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2271405B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5735412B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR101604366B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN102015026B (cg-RX-API-DMAC7.html) |
| AR (1) | AR072666A1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2009243812B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BRPI0911497B8 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2723431C (cg-RX-API-DMAC7.html) |
| CO (1) | CO6331305A2 (cg-RX-API-DMAC7.html) |
| EA (2) | EA018920B1 (cg-RX-API-DMAC7.html) |
| EC (1) | ECSP10010656A (cg-RX-API-DMAC7.html) |
| ES (1) | ES2432383T3 (cg-RX-API-DMAC7.html) |
| IL (1) | IL208989A (cg-RX-API-DMAC7.html) |
| MX (1) | MX2010011917A (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ589691A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2009135581A2 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA201008723B (cg-RX-API-DMAC7.html) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2369315T3 (es) * | 2007-06-01 | 2011-11-29 | F. Hoffmann-La Roche Ag | Derivados de piperidina-amida. |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| 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 |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| 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 |
| 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 |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| JP6354757B2 (ja) | 2013-07-09 | 2018-07-11 | 小野薬品工業株式会社 | Ａｌｘｒ作動化合物 |
| CN104910084A (zh) * | 2015-07-13 | 2015-09-16 | 佛山市赛维斯医药科技有限公司 | 末端胺基取代的三氮唑亚砜类化合物、其制备方法及其用途 |
| CN104910083A (zh) * | 2015-07-13 | 2015-09-16 | 佛山市赛维斯医药科技有限公司 | 烷氧苯基三氮唑亚砜类11β-HSD1抑制剂、制备方法及其用途 |
| EP3235813A1 (en) | 2016-04-19 | 2017-10-25 | Cidqo 2012, S.L. | Aza-tetra-cyclo derivatives |
| KR20200105652A (ko) * | 2017-09-08 | 2020-09-08 | 피아이 인더스트리스 엘티디. | 새로운 살균성 헤테로시클릭 화합물 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7754709B2 (en) * | 2003-06-10 | 2010-07-13 | Solvay Pharmaceuticals Bv | Tetracyclic thiophenepyrimidinone compounds as inhibitors of 17β hydroxysteroid dehydrogenase compounds |
| US20070231263A1 (en) | 2004-04-13 | 2007-10-04 | Jun Qiu | Human G protein-coupled receptor and modulators thereof for the treatment of hyperglycemia and related disorders |
| EP1637529A1 (en) * | 2004-09-20 | 2006-03-22 | 4Sc Ag | Novel piperidin-4-yl-thiazole-carboxamide analogues as inhibitors of T-cell proliferation and uses thereof |
| DE102006010923A1 (de) * | 2006-03-09 | 2007-09-13 | Saltigo Gmbh | Verfahren zur Herstellung von Chlor-1,4-dimethoxybenzol |
| BRPI0709595A2 (pt) * | 2006-03-15 | 2011-07-19 | 4Sc Ag | inibidores de nf-kapab heterocìclicos |
| CN101405278A (zh) | 2006-03-15 | 2009-04-08 | 4Sc股份公司 | 新颖的杂环NF-κB抑制剂 |
-
2009
- 2009-04-08 BR BRPI0911497A patent/BRPI0911497B8/pt not_active IP Right Cessation
- 2009-04-08 EA EA201001737A patent/EA018920B1/ru not_active IP Right Cessation
- 2009-04-08 US US12/991,016 patent/US8546575B2/en not_active Expired - Fee Related
- 2009-04-08 MX MX2010011917A patent/MX2010011917A/es active IP Right Grant
- 2009-04-08 EP EP09741800.8A patent/EP2271405B1/en active Active
- 2009-04-08 WO PCT/EP2009/002607 patent/WO2009135581A2/en not_active Ceased
- 2009-04-08 KR KR1020107027260A patent/KR101604366B1/ko not_active Expired - Fee Related
- 2009-04-08 JP JP2011507806A patent/JP5735412B2/ja not_active Expired - Fee Related
- 2009-04-08 CA CA2723431A patent/CA2723431C/en active Active
- 2009-04-08 AU AU2009243812A patent/AU2009243812B2/en not_active Ceased
- 2009-04-08 CN CN200980116875.5A patent/CN102015026B/zh not_active Expired - Fee Related
- 2009-04-08 NZ NZ589691A patent/NZ589691A/xx not_active IP Right Cessation
- 2009-04-08 EA EA201300759A patent/EA201300759A1/ru unknown
- 2009-04-08 ES ES09741800T patent/ES2432383T3/es active Active
- 2009-04-30 AR ARP090101563A patent/AR072666A1/es unknown
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2010
- 2010-10-28 IL IL208989A patent/IL208989A/en active IP Right Grant
- 2010-10-29 CO CO10134879A patent/CO6331305A2/es not_active Application Discontinuation
- 2010-12-02 EC EC2010010656A patent/ECSP10010656A/es unknown
- 2010-12-03 ZA ZA2010/08723A patent/ZA201008723B/en unknown
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