JP2006527215A5 - - Google Patents
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- Publication number
- JP2006527215A5 JP2006527215A5 JP2006515710A JP2006515710A JP2006527215A5 JP 2006527215 A5 JP2006527215 A5 JP 2006527215A5 JP 2006515710 A JP2006515710 A JP 2006515710A JP 2006515710 A JP2006515710 A JP 2006515710A JP 2006527215 A5 JP2006527215 A5 JP 2006527215A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- compound according
- carbamic acid
- amino
- methyl
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 claims 57
- -1 hydroxy, sulfanyl Chemical group 0.000 claims 52
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 16
- 239000008194 pharmaceutical composition Substances 0.000 claims 16
- 125000001072 heteroaryl group Chemical group 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 12
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 11
- 238000000034 method Methods 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 10
- 125000003277 amino group Chemical group 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 8
- 230000002265 prevention Effects 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- 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 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Natural products 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 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- 208000002705 Glucose Intolerance Diseases 0.000 claims 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- 102000004877 Insulin Human genes 0.000 claims 3
- 108090001061 Insulin Proteins 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 102000000019 Sterol Esterase Human genes 0.000 claims 3
- 108010055297 Sterol Esterase Proteins 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 3
- 235000012000 cholesterol Nutrition 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 150000001982 diacylglycerols Chemical class 0.000 claims 3
- 229940125396 insulin Drugs 0.000 claims 3
- 201000009104 prediabetes syndrome Diseases 0.000 claims 3
- 230000001105 regulatory effect Effects 0.000 claims 3
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims 3
- 210000002237 B-cell of pancreatic islet Anatomy 0.000 claims 2
- BPQMCHLXMUICHV-WGSAOQKQSA-N CN(C(=O)Oc1ccc(NC(=O)[C@H]2CC[C@@H](CC2)C(C)(C)C)cc1)c1ccccc1 Chemical compound CN(C(=O)Oc1ccc(NC(=O)[C@H]2CC[C@@H](CC2)C(C)(C)C)cc1)c1ccccc1 BPQMCHLXMUICHV-WGSAOQKQSA-N 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- GAMBJVPQOBYEEA-UHFFFAOYSA-N [4-[(6-chloropyridine-3-carbonyl)amino]phenyl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)N=C1 GAMBJVPQOBYEEA-UHFFFAOYSA-N 0.000 claims 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 229930195729 fatty acid Natural products 0.000 claims 2
- 239000000194 fatty acid Substances 0.000 claims 2
- 201000001421 hyperglycemia Diseases 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 230000002366 lipolytic effect Effects 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 2
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 108010028554 LDL Cholesterol Proteins 0.000 claims 1
- 238000008214 LDL Cholesterol Methods 0.000 claims 1
- LTYOQGRJFJAKNA-KKIMTKSISA-N Malonyl CoA Natural products S(C(=O)CC(=O)O)CCNC(=O)CCNC(=O)[C@@H](O)C(CO[P@](=O)(O[P@](=O)(OC[C@H]1[C@@H](OP(=O)(O)O)[C@@H](O)[C@@H](n2c3ncnc(N)c3nc2)O1)O)O)(C)C LTYOQGRJFJAKNA-KKIMTKSISA-N 0.000 claims 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- YWLQTEZKPWHZGX-UHFFFAOYSA-N [3-[(4-piperidin-1-ylbenzoyl)amino]phenyl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(C=1)=CC=CC=1NC(=O)C(C=C1)=CC=C1N1CCCCC1 YWLQTEZKPWHZGX-UHFFFAOYSA-N 0.000 claims 1
- YWKFJOURGJJBND-UHFFFAOYSA-N [3-[[4-(2-methylpiperidin-1-yl)benzoyl]amino]phenyl] n-methyl-n-phenylcarbamate Chemical compound CC1CCCCN1C1=CC=C(C(=O)NC=2C=C(OC(=O)N(C)C=3C=CC=CC=3)C=CC=2)C=C1 YWKFJOURGJJBND-UHFFFAOYSA-N 0.000 claims 1
- LZSGJZZLHLBIGV-UHFFFAOYSA-N [3-[[4-(3-methylpiperidin-1-yl)benzoyl]amino]phenyl] n-methyl-n-phenylcarbamate Chemical compound C1C(C)CCCN1C1=CC=C(C(=O)NC=2C=C(OC(=O)N(C)C=3C=CC=CC=3)C=CC=2)C=C1 LZSGJZZLHLBIGV-UHFFFAOYSA-N 0.000 claims 1
- KJSVTGIKIADKHO-UHFFFAOYSA-N [4-(3,3-dimethylbutanoylamino)phenyl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC1=CC=C(NC(=O)CC(C)(C)C)C=C1 KJSVTGIKIADKHO-UHFFFAOYSA-N 0.000 claims 1
- KCTIYEXUAMVIKJ-UHFFFAOYSA-N [4-(butanoylamino)phenyl] n-methyl-n-phenylcarbamate Chemical compound C1=CC(NC(=O)CCC)=CC=C1OC(=O)N(C)C1=CC=CC=C1 KCTIYEXUAMVIKJ-UHFFFAOYSA-N 0.000 claims 1
- AOPSJVSUTOOHJP-UHFFFAOYSA-N [4-(cyclohexanecarbonylamino)phenyl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(C=C1)=CC=C1NC(=O)C1CCCCC1 AOPSJVSUTOOHJP-UHFFFAOYSA-N 0.000 claims 1
- SEDIREFCNGXMQD-UHFFFAOYSA-N [4-(pyridine-2-carbonylamino)phenyl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(C=C1)=CC=C1NC(=O)C1=CC=CC=N1 SEDIREFCNGXMQD-UHFFFAOYSA-N 0.000 claims 1
- UTTGOFDWPWPGSW-UHFFFAOYSA-N [4-[(2-cyclohexylacetyl)amino]phenyl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(C=C1)=CC=C1NC(=O)CC1CCCCC1 UTTGOFDWPWPGSW-UHFFFAOYSA-N 0.000 claims 1
- VPLHITCARRRVSD-UHFFFAOYSA-N [4-[(2-phenoxyacetyl)amino]phenyl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(C=C1)=CC=C1NC(=O)COC1=CC=CC=C1 VPLHITCARRRVSD-UHFFFAOYSA-N 0.000 claims 1
- MFSZJAXUMCPKOJ-UHFFFAOYSA-N [4-[(4-chlorophenyl)carbamoylamino]phenyl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(C=C1)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 MFSZJAXUMCPKOJ-UHFFFAOYSA-N 0.000 claims 1
- PWOMVIFLUSDZAT-UHFFFAOYSA-N [4-[[2-(3-oxo-2,4-dihydro-1h-quinoxalin-2-yl)acetyl]amino]phenyl] n-methyl-n-phenylcarbamate Chemical compound C=1C=C(NC(=O)CC2C(NC3=CC=CC=C3N2)=O)C=CC=1OC(=O)N(C)C1=CC=CC=C1 PWOMVIFLUSDZAT-UHFFFAOYSA-N 0.000 claims 1
- WRSUVNFOGBJWRX-UHFFFAOYSA-N [4-[[4-[methyl(phenyl)carbamoyl]oxy-2-oxo-1h-quinoline-3-carbonyl]amino]phenyl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(C=C1)=CC=C1NC(=O)C(C(NC1=CC=CC=C11)=O)=C1OC(=O)N(C)C1=CC=CC=C1 WRSUVNFOGBJWRX-UHFFFAOYSA-N 0.000 claims 1
- VYULUKVWASFTCO-UHFFFAOYSA-N [4-[methyl(thiophene-2-carbonyl)amino]phenyl] n-methyl-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C)C(=O)OC(C=C1)=CC=C1N(C)C(=O)C1=CC=CS1 VYULUKVWASFTCO-UHFFFAOYSA-N 0.000 claims 1
- 230000005856 abnormality Effects 0.000 claims 1
- 239000000370 acceptor Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 210000000577 adipose tissue Anatomy 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 230000003178 anti-diabetic effect Effects 0.000 claims 1
- 230000003276 anti-hypertensive effect Effects 0.000 claims 1
- 230000003579 anti-obesity Effects 0.000 claims 1
- 239000003472 antidiabetic agent Substances 0.000 claims 1
- 230000036528 appetite Effects 0.000 claims 1
- 235000019789 appetite Nutrition 0.000 claims 1
- 230000002252 carbamoylating effect Effects 0.000 claims 1
- 230000021235 carbamoylation Effects 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001840 cholesterol esters Chemical class 0.000 claims 1
- 239000012973 diazabicyclooctane Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 235000021588 free fatty acids Nutrition 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000003914 insulin secretion Effects 0.000 claims 1
- 230000003834 intracellular effect Effects 0.000 claims 1
- 230000037041 intracellular level Effects 0.000 claims 1
- 230000008604 lipoprotein metabolism Effects 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 210000005229 liver cell Anatomy 0.000 claims 1
- LTYOQGRJFJAKNA-DVVLENMVSA-N malonyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 LTYOQGRJFJAKNA-DVVLENMVSA-N 0.000 claims 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims 1
- 229960003105 metformin Drugs 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 230000036470 plasma concentration Effects 0.000 claims 1
- QAQREVBBADEHPA-IEXPHMLFSA-N propionyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 QAQREVBBADEHPA-IEXPHMLFSA-N 0.000 claims 1
- 230000002685 pulmonary effect Effects 0.000 claims 1
- 210000002363 skeletal muscle cell Anatomy 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200300875 | 2003-06-12 | ||
| US47852503P | 2003-06-13 | 2003-06-13 | |
| PCT/DK2004/000402 WO2004111025A1 (en) | 2003-06-12 | 2004-06-10 | Para-substituted phenyl carbamates as inhibitors of hormone sensitive lipase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006527215A JP2006527215A (ja) | 2006-11-30 |
| JP2006527215A5 true JP2006527215A5 (enExample) | 2007-07-12 |
Family
ID=33553686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006515710A Withdrawn JP2006527215A (ja) | 2003-06-12 | 2004-06-10 | パラ置換されたフェニルカルバメート |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP1636201A1 (enExample) |
| JP (1) | JP2006527215A (enExample) |
| WO (1) | WO2004111025A1 (enExample) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1593520C3 (de) * | 1966-09-05 | 1974-07-11 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 3-(Carbamoyloxyphenyl)-harnstoffe bzw. -thioharnstoffe, diese enthaltende Mittel mit selektiver herbizider Wirkung sowie Verfahren zu deren Herstellung |
| NZ511572A (en) * | 1998-11-12 | 2003-06-30 | Alteon Inc | Eudesmadienolide derivatives useful as glucose and lipid lowering compounds |
| WO2001087843A1 (en) * | 2000-05-15 | 2001-11-22 | Novo Nordisk A/S | Compounds for treating disorders where a decreased level of plasma ffa is desired |
| AU8964201A (en) * | 2000-07-18 | 2002-01-30 | Hoffmann La Roche | Novel aniline derivatives |
| US7279470B2 (en) * | 2001-12-14 | 2007-10-09 | Novo Nordisk A/S | Compounds and uses thereof for decreasing activity of hormone-sensitive lipase |
-
2004
- 2004-06-10 EP EP04736508A patent/EP1636201A1/en not_active Withdrawn
- 2004-06-10 WO PCT/DK2004/000402 patent/WO2004111025A1/en not_active Ceased
- 2004-06-10 JP JP2006515710A patent/JP2006527215A/ja not_active Withdrawn
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