SK7782003A3 - Diphenyl azetidinone derivatives, method for the production thereof, medicaments containing these compounds, and their use - Google Patents

Diphenyl azetidinone derivatives, method for the production thereof, medicaments containing these compounds, and their use Download PDF

Info

Publication number: SK7782003A3
Authority: SK; Slovakia
Prior art keywords: alkyl; carbon atoms; phenyl; moiety; group
Prior art date: 2000-12-21

Application number

SK778-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Heiner Glombik

Werner Kramer

Stefanie Flohr

Wendelin Frick

Hubert Heuer

Gerhard Jaehne

Andreas Lindenschmidt

Hans-Ludwig Schaefer

Original Assignee

Aventis Pharma Gmbh

Priority date (The priority date 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 date listed.)

2000-12-21

Filing date

2001-12-11

Publication date

2003-12-02

2000-12-21 Priority claimed from DE10064402A external-priority patent/DE10064402A1/de

2001-12-11 Application filed by Aventis Pharma Gmbh filed Critical Aventis Pharma Gmbh

2003-12-02 Publication of SK7782003A3 publication Critical patent/SK7782003A3/sk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 109
239000003814 drug Substances 0.000 title claims abstract description 16
238000000034 method Methods 0.000 title claims abstract description 8
VDOXIAUNJCHYRC-UHFFFAOYSA-N 1,3-diphenylazetidin-2-one Chemical class O=C1C(C=2C=CC=CC=2)CN1C1=CC=CC=C1 VDOXIAUNJCHYRC-UHFFFAOYSA-N 0.000 title abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 175
125000000217 alkyl group Chemical group 0.000 claims description 166
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
239000000556 agonist Substances 0.000 claims description 35
229910052801 chlorine Inorganic materials 0.000 claims description 30
229910052731 fluorine Inorganic materials 0.000 claims description 30
125000002947 alkylene group Chemical group 0.000 claims description 28
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 25
125000001153 fluoro group Chemical group F* 0.000 claims description 24
229910052794 bromium Inorganic materials 0.000 claims description 22
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 22
239000000460 chlorine Substances 0.000 claims description 22
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 21
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 20
-1 lipase inhibitors Substances 0.000 claims description 18
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
239000011737 fluorine Substances 0.000 claims description 17
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 15
125000000304 alkynyl group Chemical group 0.000 claims description 13
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 12
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
239000013543 active substance Substances 0.000 claims description 11
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 11
239000000203 mixture Substances 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 11
125000002252 acyl group Chemical group 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 10
239000003112 inhibitor Substances 0.000 claims description 10
239000004480 active ingredient Substances 0.000 claims description 9
229910052740 iodine Inorganic materials 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
102000004877 Insulin Human genes 0.000 claims description 7
108090001061 Insulin Proteins 0.000 claims description 7
229940125396 insulin Drugs 0.000 claims description 7
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
229940100389 Sulfonylurea Drugs 0.000 claims description 6
239000005557 antagonist Substances 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
235000012000 cholesterol Nutrition 0.000 claims description 5
230000001419 dependent effect Effects 0.000 claims description 5
HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 4
239000003613 bile acid Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
230000037356 lipid metabolism Effects 0.000 claims description 4
102000004146 ATP citrate synthases Human genes 0.000 claims description 3
108090000662 ATP citrate synthases Proteins 0.000 claims description 3
229940123208 Biguanide Drugs 0.000 claims description 3
208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
102000016267 Leptin Human genes 0.000 claims description 3
108010092277 Leptin Proteins 0.000 claims description 3
102000004257 Potassium Channel Human genes 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
230000003178 anti-diabetic effect Effects 0.000 claims description 3
210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 claims description 3
239000000122 growth hormone Substances 0.000 claims description 3
229940039781 leptin Drugs 0.000 claims description 3
NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 claims description 3
239000002697 lyase inhibitor Substances 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
108020001213 potassium channel Proteins 0.000 claims description 3
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims description 2
SWLAMJPTOQZTAE-UHFFFAOYSA-N 4-[2-[(5-chloro-2-methoxybenzoyl)amino]ethyl]benzoic acid Chemical class COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(C(O)=O)C=C1 SWLAMJPTOQZTAE-UHFFFAOYSA-N 0.000 claims description 2
229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims description 2
102000013585 Bombesin Human genes 0.000 claims description 2
108010051479 Bombesin Proteins 0.000 claims description 2
102000019432 Galanin Human genes 0.000 claims description 2
101800002068 Galanin Proteins 0.000 claims description 2
102000018997 Growth Hormone Human genes 0.000 claims description 2
108010051696 Growth Hormone Proteins 0.000 claims description 2
229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 2
102000000853 LDL receptors Human genes 0.000 claims description 2
108010001831 LDL receptors Proteins 0.000 claims description 2
102000004882 Lipase Human genes 0.000 claims description 2
239000004367 Lipase Substances 0.000 claims description 2
108090001060 Lipase Proteins 0.000 claims description 2
108010013563 Lipoprotein Lipase Proteins 0.000 claims description 2
102100022119 Lipoprotein lipase Human genes 0.000 claims description 2
108090001030 Lipoproteins Proteins 0.000 claims description 2
102000004895 Lipoproteins Human genes 0.000 claims description 2
229940124757 MC-4 agonist Drugs 0.000 claims description 2
239000000637 Melanocyte-Stimulating Hormone Substances 0.000 claims description 2
108010007013 Melanocyte-Stimulating Hormones Proteins 0.000 claims description 2
102000002512 Orexin Human genes 0.000 claims description 2
229940124754 PPAR-alpha/gamma agonist Drugs 0.000 claims description 2
102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 2
108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 2
102000005630 Urocortins Human genes 0.000 claims description 2
108010059705 Urocortins Proteins 0.000 claims description 2
239000003888 alpha glucosidase inhibitor Substances 0.000 claims description 2
229940025084 amphetamine Drugs 0.000 claims description 2
239000003392 amylase inhibitor Substances 0.000 claims description 2
239000003963 antioxidant agent Substances 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
150000004283 biguanides Chemical class 0.000 claims description 2
DNDCVAGJPBKION-DOPDSADYSA-N bombesin Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC=1NC2=CC=CC=C2C=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1NC(=O)CC1)C(C)C)C1=CN=CN1 DNDCVAGJPBKION-DOPDSADYSA-N 0.000 claims description 2
OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 claims description 2
229960002802 bromocriptine Drugs 0.000 claims description 2
239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 claims description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
208000035475 disorder Diseases 0.000 claims description 2
229940125753 fibrate Drugs 0.000 claims description 2
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 2
239000000411 inducer Substances 0.000 claims description 2
235000019421 lipase Nutrition 0.000 claims description 2
229950004994 meglitinide Drugs 0.000 claims description 2
SLZIZIJTGAYEKK-CIJSCKBQSA-N molport-023-220-247 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)CN)[C@@H](C)O)C1=CNC=N1 SLZIZIJTGAYEKK-CIJSCKBQSA-N 0.000 claims description 2
230000002474 noradrenergic effect Effects 0.000 claims description 2
108060005714 orexin Proteins 0.000 claims description 2
239000000952 serotonin receptor agonist Substances 0.000 claims description 2
230000002295 serotoninergic effect Effects 0.000 claims description 2
239000000777 urocortin Substances 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
229940127470 Lipase Inhibitors Drugs 0.000 claims 2
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
102100036883 Cyclin-H Human genes 0.000 claims 1
101000713120 Homo sapiens Cyclin-H Proteins 0.000 claims 1
206010022489 Insulin Resistance Diseases 0.000 claims 1
102000000536 PPAR gamma Human genes 0.000 claims 1
108010016731 PPAR gamma Proteins 0.000 claims 1
229940125388 beta agonist Drugs 0.000 claims 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
230000002218 hypoglycaemic effect Effects 0.000 claims 1
229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims 1
229940076155 protein modulator Drugs 0.000 claims 1
230000009103 reabsorption Effects 0.000 claims 1
229940076279 serotonin Drugs 0.000 claims 1
208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
239000003524 antilipemic agent Substances 0.000 abstract description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 17
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 12
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
210000004185 liver Anatomy 0.000 description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 6
239000003826 tablet Substances 0.000 description 6
OLNTVTPDXPETLC-XPWALMASSA-N ezetimibe Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(O)=CC=1)C1=CC=C(F)C=C1 OLNTVTPDXPETLC-XPWALMASSA-N 0.000 description 5
XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 5
229960003105 metformin Drugs 0.000 description 5
239000008194 pharmaceutical composition Substances 0.000 description 5
241000699666 Mus <mouse, genus> Species 0.000 description 4
229960000815 ezetimibe Drugs 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 4
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
MPWASJLGYZIDCP-UHFFFAOYSA-N 6-[2-[3-hydroxy-3-phenyl-2-pyridin-2-yl-1-(pyridin-2-ylamino)propyl]anilino]-6-oxohexanoic acid Chemical compound C=1C=CC=CC=1C(O)C(C=1N=CC=CC=1)C(C=1C(=CC=CC=1)NC(=O)CCCCC(O)=O)NC1=CC=CC=N1 MPWASJLGYZIDCP-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
FAEKWTJYAYMJKF-QHCPKHFHSA-N GlucoNorm Chemical compound C1=C(C(O)=O)C(OCC)=CC(CC(=O)N[C@@H](CC(C)C)C=2C(=CC=CC=2)N2CCCCC2)=C1 FAEKWTJYAYMJKF-QHCPKHFHSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 3
WBWWGRHZICKQGZ-UHFFFAOYSA-N Taurocholic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCCS(O)(=O)=O)C)C1(C)C(O)C2 WBWWGRHZICKQGZ-UHFFFAOYSA-N 0.000 description 3
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000002775 capsule Substances 0.000 description 3
230000001906 cholesterol absorption Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229940079593 drug Drugs 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000008187 granular material Substances 0.000 description 3
229940028435 intralipid Drugs 0.000 description 3
229960004844 lovastatin Drugs 0.000 description 3
PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 3
QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 3
229960005095 pioglitazone Drugs 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000000651 prodrug Substances 0.000 description 3
229940002612 prodrug Drugs 0.000 description 3
229960002354 repaglinide Drugs 0.000 description 3
229960004586 rosiglitazone Drugs 0.000 description 3
239000000126 substance Substances 0.000 description 3
GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 3
229960001641 troglitazone Drugs 0.000 description 3
GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 3
XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 2
ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 2
VMLJPISAOKPHHX-UHFFFAOYSA-N 12-[2-[3-hydroxy-3-phenyl-2-pyridin-2-yl-1-(pyridin-2-ylamino)propyl]anilino]-12-oxododecanoic acid Chemical compound C=1C=CC=CC=1C(O)C(C=1N=CC=CC=1)C(C=1C(=CC=CC=1)NC(=O)CCCCCCCCCCC(O)=O)NC1=CC=CC=N1 VMLJPISAOKPHHX-UHFFFAOYSA-N 0.000 description 2
GUSVHVVOABZHAH-OPZWKQDFSA-N 1aw8p77hkj Chemical compound O([C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4C[C@H]5[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@@H]([C@]1(OC[C@H](C)CC1)O5)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GUSVHVVOABZHAH-OPZWKQDFSA-N 0.000 description 2
ZCLFJPYGSCRMSL-UHFFFAOYSA-N 9-[2-[3-hydroxy-3-phenyl-2-pyridin-2-yl-1-(pyridin-2-ylamino)propyl]anilino]-9-oxononanoic acid Chemical compound C=1C=CC=CC=1C(O)C(C=1N=CC=CC=1)C(C=1C(=CC=CC=1)NC(=O)CCCCCCCC(O)=O)NC1=CC=CC=N1 ZCLFJPYGSCRMSL-UHFFFAOYSA-N 0.000 description 2
241000220479 Acacia Species 0.000 description 2
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 2
XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 2
PTQXTEKSNBVPQJ-UHFFFAOYSA-N Avasimibe Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1CC(=O)NS(=O)(=O)OC1=C(C(C)C)C=CC=C1C(C)C PTQXTEKSNBVPQJ-UHFFFAOYSA-N 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
235000010643 Leucaena leucocephala Nutrition 0.000 description 2
229940086609 Lipase inhibitor Drugs 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
229960002632 acarbose Drugs 0.000 description 2
XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
229960005370 atorvastatin Drugs 0.000 description 2
229950010046 avasimibe Drugs 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
229960000516 bezafibrate Drugs 0.000 description 2
IIBYAHWJQTYFKB-UHFFFAOYSA-N bezafibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 IIBYAHWJQTYFKB-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
229960001214 clofibrate Drugs 0.000 description 2
KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
229960002297 fenofibrate Drugs 0.000 description 2
YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 description 2
229960003765 fluvastatin Drugs 0.000 description 2
235000013305 food Nutrition 0.000 description 2
210000004051 gastric juice Anatomy 0.000 description 2
229960004580 glibenclamide Drugs 0.000 description 2
ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 description 2
229960001381 glipizide Drugs 0.000 description 2
ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 2
229940126904 hypoglycaemic agent Drugs 0.000 description 2
230000001976 improved effect Effects 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 2
229960001243 orlistat Drugs 0.000 description 2
VWMZIGBYZQUQOA-QEEMJVPDSA-N pamaqueside Chemical compound O([C@@H]1[C@@H](CO)O[C@H]([C@@H]([C@H]1O)O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4C[C@H]5[C@@H]([C@]4(CC(=O)[C@@H]3[C@@]2(C)CC1)C)[C@@H]([C@]1(OC[C@H](C)CC1)O5)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VWMZIGBYZQUQOA-QEEMJVPDSA-N 0.000 description 2
229950005482 pamaqueside Drugs 0.000 description 2
229960003562 phentermine Drugs 0.000 description 2
229960002965 pravastatin Drugs 0.000 description 2
TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000007493 shaping process Methods 0.000 description 2
229960002855 simvastatin Drugs 0.000 description 2
RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
229950004437 tiqueside Drugs 0.000 description 2
229960005371 tolbutamide Drugs 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
DBGIVFWFUFKIQN-VIFPVBQESA-N (+)-Fenfluramine Chemical compound CCN[C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-VIFPVBQESA-N 0.000 description 1
DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical group CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
LAWHHRXCBUNWFI-UHFFFAOYSA-N 2-pentylpropanedioic acid Chemical compound CCCCCC(C(O)=O)C(O)=O LAWHHRXCBUNWFI-UHFFFAOYSA-N 0.000 description 1
MLZFHMHFCYXHLF-UHFFFAOYSA-N 3-(2-aminophenyl)-1-phenyl-2-pyridin-2-yl-3-(pyridin-2-ylamino)propan-1-ol Chemical compound NC1=CC=CC=C1C(C(C(O)C=1C=CC=CC=1)C=1N=CC=CC=1)NC1=CC=CC=N1 MLZFHMHFCYXHLF-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 description 1
GOMUHAODASRBBA-UHFFFAOYSA-N 4-[4-(aminomethyl)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one Chemical compound C1=CC(CN)=CC=C1C1N(C=2C=CC(F)=CC=2)C(=O)C1CCC(O)C1=CC=C(F)C=C1 GOMUHAODASRBBA-UHFFFAOYSA-N 0.000 description 1
QBQLYIISSRXYKL-UHFFFAOYSA-N 4-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-1,2-oxazolidine-3,5-dione Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC1C(=O)NOC1=O QBQLYIISSRXYKL-UHFFFAOYSA-N 0.000 description 1
AUEUBSJNKBZSKK-UHFFFAOYSA-N 5-benzylsulfonyl-2-[2-(dimethylamino)ethyl-ethylamino]-n,n-diethyl-4-(4-phenylpiperidin-1-yl)benzamide Chemical compound C1=C(N(CC)CCN(C)C)C(C(=O)N(CC)CC)=CC(S(=O)(=O)CC=2C=CC=CC=2)=C1N(CC1)CCC1C1=CC=CC=C1 AUEUBSJNKBZSKK-UHFFFAOYSA-N 0.000 description 1
206010003210 Arteriosclerosis Diseases 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
229920001268 Cholestyramine Polymers 0.000 description 1
241000699800 Cricetinae Species 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
101710198884 GATA-type zinc finger protein 1 Proteins 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
102000051325 Glucagon Human genes 0.000 description 1
108060003199 Glucagon Proteins 0.000 description 1
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 description 1
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 1
102000004366 Glucosidases Human genes 0.000 description 1
108010056771 Glucosidases Proteins 0.000 description 1
239000000095 Growth Hormone-Releasing Hormone Substances 0.000 description 1
208000035150 Hypercholesterolemia Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
108010057186 Insulin Glargine Proteins 0.000 description 1
COCFEDIXXNGUNL-RFKWWTKHSA-N Insulin glargine Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3NC=NC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(=O)NCC(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 COCFEDIXXNGUNL-RFKWWTKHSA-N 0.000 description 1
229940122355 Insulin sensitizer Drugs 0.000 description 1
108010028554 LDL Cholesterol Proteins 0.000 description 1
238000008214 LDL Cholesterol Methods 0.000 description 1
229940122014 Lyase inhibitor Drugs 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
ZPXSCAKFGYXMGA-UHFFFAOYSA-N Mazindol Chemical group N12CCN=C2C2=CC=CC=C2C1(O)C1=CC=C(Cl)C=C1 ZPXSCAKFGYXMGA-UHFFFAOYSA-N 0.000 description 1
241000699673 Mesocricetus auratus Species 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
IBAQFPQHRJAVAV-ULAWRXDQSA-N Miglitol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO IBAQFPQHRJAVAV-ULAWRXDQSA-N 0.000 description 1
241000237536 Mytilus edulis Species 0.000 description 1
238000011785 NMRI mouse Methods 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
229940080774 Peroxisome proliferator-activated receptor gamma agonist Drugs 0.000 description 1
229940127315 Potassium Channel Openers Drugs 0.000 description 1
102100040918 Pro-glucagon Human genes 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
102100022831 Somatoliberin Human genes 0.000 description 1
101710142969 Somatoliberin Proteins 0.000 description 1
229940123495 Squalene synthetase inhibitor Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
230000009858 acid secretion Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
229920006318 anionic polymer Polymers 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
239000003472 antidiabetic agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
RCHHVVGSTHAVPF-ZPHPLDECSA-N apidra Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3N=CNC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CNC=N1 RCHHVVGSTHAVPF-ZPHPLDECSA-N 0.000 description 1
208000011775 arteriosclerosis disease Diseases 0.000 description 1
239000002585 base Substances 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
239000013553 cell monolayer Substances 0.000 description 1
229940081734 cellulose acetate phthalate Drugs 0.000 description 1
229960005110 cerivastatin Drugs 0.000 description 1
SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
229940125881 cholesteryl ester transfer protein inhibitor Drugs 0.000 description 1
YZFWTZACSRHJQD-UHFFFAOYSA-N ciglitazone Chemical compound C=1C=C(CC2C(NC(=O)S2)=O)C=CC=1OCC1(C)CCCCC1 YZFWTZACSRHJQD-UHFFFAOYSA-N 0.000 description 1
229950009226 ciglitazone Drugs 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
239000007891 compressed tablet Substances 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
229960004597 dexfenfluramine Drugs 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000002532 enzyme inhibitor Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
229960001582 fenfluramine Drugs 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
230000037406 food intake Effects 0.000 description 1
235000012631 food intake Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)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(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 description 1
229960004666 glucagon Drugs 0.000 description 1
230000004110 gluconeogenesis Effects 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
230000004116 glycogenolysis Effects 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
230000000055 hyoplipidemic effect Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
210000004347 intestinal mucosa Anatomy 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229940099563 lactobionic acid Drugs 0.000 description 1
229940060975 lantus Drugs 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
229960001110 miglitol Drugs 0.000 description 1
239000007932 molded tablet Substances 0.000 description 1
238000000465 moulding Methods 0.000 description 1
235000020638 mussel Nutrition 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
229910017604 nitric acid Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical class O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 description 1
238000005192 partition Methods 0.000 description 1
235000014594 pastries Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940100467 polyvinyl acetate phthalate Drugs 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
230000002265 prevention Effects 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
239000000700 radioactive tracer Substances 0.000 description 1
229960000672 rosuvastatin Drugs 0.000 description 1
BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000003772 serotonin uptake inhibitor Substances 0.000 description 1
229960004425 sibutramine Drugs 0.000 description 1
UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000004059 squalene synthase inhibitor Substances 0.000 description 1
235000000891 standard diet Nutrition 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
WBWWGRHZICKQGZ-GIHLXUJPSA-N taurocholic acid Chemical compound C([C@@H]1C[C@H]2O)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@H](O)C1 WBWWGRHZICKQGZ-GIHLXUJPSA-N 0.000 description 1
235000021195 test diet Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000032258 transport Effects 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Hematology (AREA)
Obesity (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SK778-2003A 2000-12-21 2001-12-11 Diphenyl azetidinone derivatives, method for the production thereof, medicaments containing these compounds, and their use SK7782003A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE10064402A DE10064402A1 (de)	2000-12-21	2000-12-21	Diphenylazetidinonderivate, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung
DE10154518		2001-11-07
PCT/EP2001/014533 WO2002050060A1 (fr)	2000-12-21	2001-12-11	Derives de diphenylazetinone, procede permettant de les produire, medicaments contenant lesdits composes et leur utilisation

Publications (1)

Publication Number	Publication Date
SK7782003A3 true SK7782003A3 (en)	2003-12-02

Family

ID=26008044

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK778-2003A SK7782003A3 (en)	2000-12-21	2001-12-11	Diphenyl azetidinone derivatives, method for the production thereof, medicaments containing these compounds, and their use

Country Status (23)

Country	Link
US (1)	US6703386B2 (fr)
EP (1)	EP1345924B1 (fr)
JP (1)	JP2004516289A (fr)
KR (1)	KR20030063462A (fr)
CN (1)	CN1221546C (fr)
AR (1)	AR033600A1 (fr)
AT (1)	ATE338039T1 (fr)
AU (1)	AU2002231688A1 (fr)
BR (1)	BR0116322A (fr)
CA (1)	CA2431995A1 (fr)
CZ (1)	CZ20031733A3 (fr)
DE (1)	DE50110906D1 (fr)
EE (1)	EE200300238A (fr)
HR (1)	HRP20030501A2 (fr)
HU (1)	HUP0401073A2 (fr)
IL (1)	IL156548A0 (fr)
MX (1)	MXPA03005019A (fr)
NO (1)	NO20032735L (fr)
NZ (1)	NZ526594A (fr)
PL (1)	PL362512A1 (fr)
SK (1)	SK7782003A3 (fr)
WO (1)	WO2002050060A1 (fr)
YU (1)	YU47803A (fr)

Families Citing this family (55)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6982251B2 (en)	2000-12-20	2006-01-03	Schering Corporation	Substituted 2-azetidinones useful as hypocholesterolemic agents
AR034204A1 (es) *	2001-01-26	2004-02-04	Schering Corp	Composiciones y combinaciones de acido nicotinico y derivados del mismo con inhibidor(es) de la absorcion de los esteroles, y el uso de los mismos para preparar medicamentos para el tratamiento para indicaciones vasculares
US7071181B2 (en)	2001-01-26	2006-07-04	Schering Corporation	Methods and therapeutic combinations for the treatment of diabetes using sterol absorption inhibitors
RU2756946C2 (ru)	2001-01-26	2021-10-07	Мерк Шарп И Доум Корп.	Применение замещенных азетидинонов для лечения ситостеролемии
AU2002247019C1 (en) *	2001-01-26	2017-05-11	Organon Llc	Combinations of peroxisome proliferator-activated receptor (PPAR) activator(s) and sterol absorption inhibitor(s) and treatments for vascular indications
ATE369851T1 (de) *	2001-01-26	2007-09-15	Schering Corp	Kombinationen von gallensäuresequestriermitteln und hemmern der sterolabsorption zur behandlung von kardiovaskulären indikationen
ES2296894T3 (es) *	2001-01-26	2008-05-01	Schering Corporation	Combinaciones de ezetimiba con aspirina para tratar estados vasculares.
CN1582168A (zh) *	2001-01-26	2005-02-16	先灵公司	用于治疗血管性疾病的固醇吸收抑制剂与心血管药剂的组合
TWI291957B (en) *	2001-02-23	2008-01-01	Kotobuki Pharmaceutical Co Ltd	Beta-lactam compounds, process for repoducing the same and serum cholesterol-lowering agents containing the same
US7056906B2 (en)	2001-09-21	2006-06-06	Schering Corporation	Combinations of hormone replacement therapy composition(s) and sterol absorption inhibitor(s) and treatments for vascular conditions in post-menopausal women
US7053080B2 (en)	2001-09-21	2006-05-30	Schering Corporation	Methods and therapeutic combinations for the treatment of obesity using sterol absorption inhibitors
US20030119808A1 (en) *	2001-09-21	2003-06-26	Schering Corporation	Methods of treating or preventing cardiovascular conditions while preventing or minimizing muscular degeneration side effects
DE60216300T2 (de)	2001-09-21	2007-06-28	Schering Corp.	Behandlung von xanthom mittels azetidinon-derivate als hemmer der sterol absorption
US7176193B2 (en)	2002-06-19	2007-02-13	Sanofi-Aventis Deutschland Gmbh	Acid-group-substituted diphenylazetidinones, process for their preparation, medicaments comprising these compounds, and their use
US7671047B2 (en)	2002-06-19	2010-03-02	Sanofi-Aventis Deutschland Gmbh	Cationically substituted diphenylazetidinones, process for their preparation, medicaments comprising these compounds, and their use
US7176194B2 (en)	2002-06-19	2007-02-13	Sanofi-Aventis Deutschland Gmbh	Ring-substituted diphenylazetidinones, process for their preparation, medicaments comprising these compounds, and their use
DE10227507A1 (de) *	2002-06-19	2004-01-08	Aventis Pharma Deutschland Gmbh	Kationisch substituierte Diphenylazetidinone, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung
DE10227508A1 (de) *	2002-06-19	2004-01-08	Aventis Pharma Deutschland Gmbh	Säuregruppen-substituierte Diphenylazetidinone, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung
GB0215579D0 (en) *	2002-07-05	2002-08-14	Astrazeneca Ab	Chemical compounds
DE10303900A1 (de) *	2003-01-31	2004-08-12	Nutrinova Nutrition Specialties & Food Ingredients Gmbh	Cholesterinsenkendes Mittel, enthaltend Levane
CA2504878A1 (fr)	2002-11-06	2004-05-27	Schering Corporation	Inhibiteurs d'absorption du cholesterol pour le traitement de la demyelination
MXPA05009502A (es)	2003-03-07	2005-10-18	Schering Corp	Compuestos de azetidinona sustituidos, formulaciones y usos de los mismos para el tratamiento de hipercolesterolemia.
MXPA05009501A (es)	2003-03-07	2005-10-18	Schering Corp	Compuestos de azetidinona sustituidos, formulaciones y usos de los mismos para el tratamiento de hipercolesterolemia.
EP1601668B1 (fr)	2003-03-07	2008-08-27	Schering Corporation	Composes d'azetidinone substitues, leurs formulations et utilisations en vue du traitement de l'hypercholesterolemie
US7459442B2 (en)	2003-03-07	2008-12-02	Schering Corporation	Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof
WO2005021497A2 (fr) *	2003-08-28	2005-03-10	Microbia, Inc.	Trimeres et dimeres fixes de 1,4-diphenylazetidin-2-ones
EP1918000A2 (fr)	2003-11-05	2008-05-07	Schering Corporation	Combinaisons d'agents de modulation lipide et azétidinones substitués et traitements pour conditions vasculaires
JP4688819B2 (ja) *	2003-12-23	2011-05-25	アストラゼネカアクチボラグ	コレステロール吸収阻害活性を有するジフェニルアゼチジノン誘導体
RU2380360C2 (ru) *	2003-12-23	2010-01-27	Астразенека Аб	Дифенилазетидиноновые производные, обладающие активностью, ингибирующей всасывание холестерина
GB0329778D0 (en) *	2003-12-23	2004-01-28	Astrazeneca Ab	Chemical compounds
DE102004024454A1 (de) *	2004-05-14	2005-12-08	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Neue Enantiomerenreine Betaagonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel
EP1807070A1 (fr) *	2004-09-29	2007-07-18	Schering Corporation	Combinaisons d'azetidinones substituees et d'antagonistes cb1
NZ555320A (en)	2004-12-03	2010-11-26	Schering Corp	Substituted piperazines as CB1 antagonists
EP1902046B1 (fr) *	2005-06-20	2009-12-02	Schering Corporation	Dérivés de la pipéridine utiles comme antagonistes du récepteur h3 de l'histamine
SA06270191B1 (ar)	2005-06-22	2010-03-29	استرازينيكا ايه بي	مشتقات من 2- أزيتيدينون جديدة باعتبارها مثبطات لامتصاص الكوليسترول لعلاج حالات فرط نسبة الدهون في الدم
US7897601B2 (en) *	2006-01-18	2011-03-01	Intervet, Inc.	Cannabinoid receptor modulators
AR060623A1 (es)	2006-04-27	2008-07-02	Astrazeneca Ab	Compuestos derivados de 2-azetidinona y un metodo de preparacion
AU2007283113A1 (en)	2006-08-08	2008-02-14	Sanofi-Aventis	Arylaminoaryl-alkyl-substituted imidazolidine-2,4-diones, processes for preparing them, medicaments comprising these compounds, and their use
EP2059241A1 (fr) *	2006-09-05	2009-05-20	Schering Corporation	Compositions pharmaceutiques pour un traitement des lipides et dans le traitement de l'athérosclérose et de la stéatose hépatique
WO2008130616A2 (fr) *	2007-04-19	2008-10-30	Schering Corporation	Diaryl morpholines comme modulateurs des récepteurs cb1
CN101796033A (zh) *	2007-06-28	2010-08-04	英特维特国际股份有限公司	作为cb1拮抗剂的取代的哌嗪
CN101790521A (zh) *	2007-06-28	2010-07-28	英特维特国际股份有限公司	作为cb1拮抗剂的取代哌嗪
EP2025674A1 (fr)	2007-08-15	2009-02-18	sanofi-aventis	Tetrahydronaphthaline substituée, son procédé de fabrication et son utilisation en tant que médicament
DE102007054497B3 (de)	2007-11-13	2009-07-23	Sanofi-Aventis Deutschland Gmbh	Neue kristalline Diphenylazetidinonhydrate und Verfahren zu deren Herstellung
US8470841B2 (en)	2008-07-09	2013-06-25	Sanofi	Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof
WO2010068601A1 (fr)	2008-12-08	2010-06-17	Sanofi-Aventis	Hydrate de fluoroglycoside hétéroaromatique cristallin, ses procédés de fabrication, ses procédés d'utilisation et compositions pharmaceutiques le contenant
US9212175B2 (en)	2009-03-06	2015-12-15	Lipideon Biotechnology Ag	Pharmaceutical hypocholesterolemic compositions
CN101993403B (zh)	2009-08-11	2012-07-11	浙江海正药业股份有限公司	氮杂环丁酮类化合物及医药应用
JP2013503135A (ja)	2009-08-26	2013-01-31	サノフイ	新規な結晶性複素芳香族フルオログリコシド水和物、その化合物を含んでなる医薬及びその使用
EP2582709B1 (fr)	2010-06-18	2018-01-24	Sanofi	Dérivés d'azolopyridin-3-one en tant qu'inhibiteurs de lipases et de phospholipases
EP2766349B1 (fr)	2011-03-08	2016-06-01	Sanofi	Dérivés d'oxathiazine substitués par des carbocycles ou des hétérocycles, leur procédé de préparation, médicaments contenant ces composés et leur utilisation
WO2012120056A1 (fr)	2011-03-08	2012-09-13	Sanofi	Dérivés oxathiazine tétra-substitués, procédé pour leur préparation, utilisation en tant que médicament, agent pharmaceutique contenant ces dérivés et utilisation
WO2012120054A1 (fr)	2011-03-08	2012-09-13	Sanofi	Dérivés oxathiazine di- et tri-substitués, procédé pour leur préparation, utilisation en tant que médicament, agent pharmaceutique contenant ces dérivés et utilisation
EP2683699B1 (fr)	2011-03-08	2015-06-24	Sanofi	Dérivés oxathiazine di- et tri-substitués, procédé pour leur préparation, utilisation en tant que médicament, agent pharmaceutique contenant ces dérivés et utilisation
EP2683704B1 (fr)	2011-03-08	2014-12-17	Sanofi	Dérivés oxathiazine ramifiés, procédé pour leur préparation, utilisation en tant que médicament, agents pharmaceutiques contenant ces dérivés et leur utilisation

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH10501811A (ja) *	1994-06-20	1998-02-17	シェーリングコーポレイション	低コレステロール化剤として有用な置換アゼチジノン化合物
WO1997026265A1 (fr)	1996-01-17	1997-07-24	Novo Nordisk A/S	Derives de 1,2,4-thiadiazine fusionnee et de 1,4-thiazine fusionnee, leur preparation et utilisation
JP3149958B2 (ja)	1996-08-30	2001-03-26	ノボノルディスクアクティーゼルスカブ	Ｇｌｐ―１誘導体
ES2223091T3 (es) *	1997-04-04	2005-02-16	Aventis Pharma Deutschland Gmbh	Derivados de propanolamina hipolipidemicos.
DE19845402B4 (de) *	1998-10-02	2005-04-07	Aventis Pharma Deutschland Gmbh	Mit Heterocyclen substituierte Propanolaminderivate, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung
KR20010021936A (ko)	1997-07-16	2001-03-15	한센 핀 베네드, 안네 제헤르, 웨이콥 마리안느	융합된 1,2,4-티아디아진 유도체, 그의 제조와 사용
DE19845406C2 (de) *	1998-10-02	2001-10-18	Aventis Pharma Gmbh	Substituierte 1,3-Diaryl-2-pyridin-2-yl-3-(pyridin-2-ylamino)- propanolderivate, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung

2001
- 2001-12-11 HR HR20030501A patent/HRP20030501A2/xx not_active Application Discontinuation
- 2001-12-11 AT AT01991821T patent/ATE338039T1/de not_active IP Right Cessation
- 2001-12-11 PL PL01362512A patent/PL362512A1/xx not_active Application Discontinuation
- 2001-12-11 NZ NZ526594A patent/NZ526594A/en unknown
- 2001-12-11 DE DE50110906T patent/DE50110906D1/de not_active Expired - Lifetime
- 2001-12-11 JP JP2002551556A patent/JP2004516289A/ja not_active Abandoned
- 2001-12-11 CN CNB018210430A patent/CN1221546C/zh not_active Expired - Fee Related
- 2001-12-11 EP EP01991821A patent/EP1345924B1/fr not_active Expired - Lifetime
- 2001-12-11 YU YU47803A patent/YU47803A/sh unknown
- 2001-12-11 KR KR10-2003-7008503A patent/KR20030063462A/ko not_active Withdrawn
- 2001-12-11 WO PCT/EP2001/014533 patent/WO2002050060A1/fr not_active Ceased
- 2001-12-11 EE EEP200300238A patent/EE200300238A/xx unknown
- 2001-12-11 MX MXPA03005019A patent/MXPA03005019A/es active IP Right Grant
- 2001-12-11 IL IL15654801A patent/IL156548A0/xx unknown
- 2001-12-11 CA CA002431995A patent/CA2431995A1/fr not_active Abandoned
- 2001-12-11 BR BR0116322-1A patent/BR0116322A/pt not_active IP Right Cessation
- 2001-12-11 CZ CZ20031733A patent/CZ20031733A3/cs unknown
- 2001-12-11 HU HU0401073A patent/HUP0401073A2/hu unknown
- 2001-12-11 SK SK778-2003A patent/SK7782003A3/sk unknown
- 2001-12-11 AU AU2002231688A patent/AU2002231688A1/en not_active Abandoned
- 2001-12-19 AR ARP010105908A patent/AR033600A1/es unknown
- 2001-12-19 US US10/021,044 patent/US6703386B2/en not_active Expired - Lifetime
2003
- 2003-06-16 NO NO20032735A patent/NO20032735L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
CN1481378A (zh)	2004-03-10
WO2002050060A1 (fr)	2002-06-27
PL362512A1 (en)	2004-11-02
KR20030063462A (ko)	2003-07-28
MXPA03005019A (es)	2003-09-25
EE200300238A (et)	2003-08-15
BR0116322A (pt)	2003-10-14
JP2004516289A (ja)	2004-06-03
CA2431995A1 (fr)	2002-06-27
US6703386B2 (en)	2004-03-09
CZ20031733A3 (cs)	2003-09-17
NO20032735D0 (no)	2003-06-16
NZ526594A (en)	2004-08-27
YU47803A (sh)	2006-05-25
US20020128253A1 (en)	2002-09-12
CN1221546C (zh)	2005-10-05
DE50110906D1 (de)	2006-10-12
IL156548A0 (en)	2004-01-04
ATE338039T1 (de)	2006-09-15
AU2002231688A1 (en)	2002-07-01
HK1060119A1 (en)	2004-07-30
NO20032735L (no)	2003-08-06
HUP0401073A2 (hu)	2004-09-28
EP1345924B1 (fr)	2006-08-30
EP1345924A1 (fr)	2003-09-24
AR033600A1 (es)	2003-12-26
HRP20030501A2 (en)	2005-04-30

Publication	Publication Date	Title
SK7782003A3 (en)	2003-12-02	Diphenyl azetidinone derivatives, method for the production thereof, medicaments containing these compounds, and their use
US6498156B2 (en)	2002-12-24	Diphenylazetidinone derivatives, process for their preparation, medicaments comprising these compounds and their use
RU2287522C2 (ru)	2006-11-20	Замещенные кислотными группами дифенилазетидиноны, способ их получения, содержащие эти соединения лекарственные средства и их применение
RU2315753C2 (ru)	2008-01-27	Катионозамещенные дифенилазетидиноны, способ их получения, лекарственные средства, содержащие эти соединения, и их применение
US7388004B2 (en)	2008-06-17	Acid-group-substituted diphenylazetidinones, process for their preparation, medicaments comprising these compounds, and their use
US7671047B2 (en)	2010-03-02	Cationically substituted diphenylazetidinones, process for their preparation, medicaments comprising these compounds, and their use
RU2282628C2 (ru)	2006-08-27	Производные дифенилазетидинона, фармацевтическая композиция на их основе и способ ее получения
NZ537302A (en)	2006-06-30	Diphenyl azetidinones substituted by acidic groups, method for their production, medicaments containing said compounds and use thereof
NZ537303A (en)	2006-06-30	Cationically substituted diphenyl azetidinones, method for their production, medicaments containing said compounds and use thereof
HK1079511B (en)	2009-07-03	Diphenyl azetidinones substituted by acidic groups, method for their production, medicaments containing said compounds and use thereof

Legal Events

Date	Code	Title	Description
2010-03-08	FD9A	Suspended procedure due to non-payment of fee