JP2017509679A5 - - Google Patents
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- Publication number
- JP2017509679A5 JP2017509679A5 JP2016560725A JP2016560725A JP2017509679A5 JP 2017509679 A5 JP2017509679 A5 JP 2017509679A5 JP 2016560725 A JP2016560725 A JP 2016560725A JP 2016560725 A JP2016560725 A JP 2016560725A JP 2017509679 A5 JP2017509679 A5 JP 2017509679A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- oxo
- membered
- oxy
- pyrrolidin
- 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.)
- Abandoned
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- 239000003112 inhibitor Substances 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 17
- 229910052731 fluorine Inorganic materials 0.000 claims 15
- 229910052757 nitrogen Inorganic materials 0.000 claims 15
- 229910052799 carbon Inorganic materials 0.000 claims 10
- 229910052801 chlorine Inorganic materials 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- -1 Cyclopropylmethoxy Chemical group 0.000 claims 8
- 229910052794 bromium Inorganic materials 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 239000000556 agonist Substances 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 230000009977 dual effect Effects 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 4
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims 4
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims 4
- 102100040918 Pro-glucagon Human genes 0.000 claims 4
- 239000005557 antagonist Substances 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- DGENZVKCTGIDRZ-UHFFFAOYSA-N 3-[4-[(3-phenoxyphenyl)methylamino]phenyl]propanoic acid Chemical compound C1=CC(CCC(=O)O)=CC=C1NCC1=CC=CC(OC=2C=CC=CC=2)=C1 DGENZVKCTGIDRZ-UHFFFAOYSA-N 0.000 claims 3
- 108010067722 Dipeptidyl Peptidase 4 Proteins 0.000 claims 3
- 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 claims 3
- 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 claims 3
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 3
- 229940123518 Sodium/glucose cotransporter 2 inhibitor Drugs 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 3
- 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 3
- 229940044601 receptor agonist Drugs 0.000 claims 3
- 239000000018 receptor agonist Substances 0.000 claims 3
- 229960005486 vaccine Drugs 0.000 claims 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 102100035765 Angiotensin-converting enzyme 2 Human genes 0.000 claims 2
- 108090000975 Angiotensin-converting enzyme 2 Proteins 0.000 claims 2
- 108010064733 Angiotensins Proteins 0.000 claims 2
- 102000015427 Angiotensins Human genes 0.000 claims 2
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 2
- 108030001679 Endothelin-converting enzyme 1 Proteins 0.000 claims 2
- 102000048186 Endothelin-converting enzyme 1 Human genes 0.000 claims 2
- 229940125827 GPR40 agonist Drugs 0.000 claims 2
- 102000036770 Islet Amyloid Polypeptide Human genes 0.000 claims 2
- 108010041872 Islet Amyloid Polypeptide Proteins 0.000 claims 2
- 102000016267 Leptin Human genes 0.000 claims 2
- 108010092277 Leptin Proteins 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 229940126033 PPAR agonist Drugs 0.000 claims 2
- 102000001253 Protein Kinase Human genes 0.000 claims 2
- 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 claims 2
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims 2
- 230000003276 anti-hypertensive effect Effects 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000002308 endothelin receptor antagonist Substances 0.000 claims 2
- 239000002792 enkephalinase inhibitor Substances 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 229940039781 leptin Drugs 0.000 claims 2
- 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 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 claims 2
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 108060006633 protein kinase Proteins 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 claims 2
- 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 claims 1
- 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 1
- 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 claims 1
- 229940124681 11 beta HSD inhibitor Drugs 0.000 claims 1
- GIZXZQYFCIFYES-HXUWFJFHSA-N 2-[6-[(3R)-3-[6-(4-fluorophenoxy)pyridin-3-yl]oxy-2-oxopyrrolidin-1-yl]-3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2-yl]-N,N-dimethylacetamide Chemical compound FC1=CC=C(OC2=CC=C(C=N2)O[C@H]2C(N(CC2)C=2C=CC=3N(C2)C(N(N3)CC(=O)N(C)C)=O)=O)C=C1 GIZXZQYFCIFYES-HXUWFJFHSA-N 0.000 claims 1
- GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 claims 1
- IGRCWJPBLWGNPX-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-(4-chlorophenyl)-n,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl IGRCWJPBLWGNPX-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 102100036009 5'-AMP-activated protein kinase catalytic subunit alpha-2 Human genes 0.000 claims 1
- 102000006902 5-HT2C Serotonin Receptor Human genes 0.000 claims 1
- 108010072553 5-HT2C Serotonin Receptor Proteins 0.000 claims 1
- MPLLLQUZNJSVTK-UHFFFAOYSA-N 5-[3-[4-[2-(4-fluorophenyl)ethoxy]phenyl]propyl]furan-2-carboxylic acid Chemical compound O1C(C(=O)O)=CC=C1CCCC(C=C1)=CC=C1OCCC1=CC=C(F)C=C1 MPLLLQUZNJSVTK-UHFFFAOYSA-N 0.000 claims 1
- HFDKKNHCYWNNNQ-YOGANYHLSA-N 75976-10-2 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@@H](NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)N)C(C)C)[C@@H](C)O)C1=CC=C(O)C=C1 HFDKKNHCYWNNNQ-YOGANYHLSA-N 0.000 claims 1
- 239000005541 ACE inhibitor Substances 0.000 claims 1
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 claims 1
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 claims 1
- 229940121969 Aminopeptidase A inhibitor Drugs 0.000 claims 1
- 102000008873 Angiotensin II receptor Human genes 0.000 claims 1
- 108050000824 Angiotensin II receptor Proteins 0.000 claims 1
- 102000005666 Apolipoprotein A-I Human genes 0.000 claims 1
- 108010059886 Apolipoprotein A-I Proteins 0.000 claims 1
- 101100460776 Arabidopsis thaliana NPY2 gene Proteins 0.000 claims 1
- 101100460782 Arabidopsis thaliana NPY4 gene Proteins 0.000 claims 1
- 101100460788 Arabidopsis thaliana NPY5 gene Proteins 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 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 claims 1
- 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 claims 1
- 102100034159 Beta-3 adrenergic receptor Human genes 0.000 claims 1
- 229940123208 Biguanide Drugs 0.000 claims 1
- WSSYGOGBNLYAIM-OAQYLSRUSA-N C1(CC1)CC(=O)C1=CC=C(O[C@H]2C(N(CC2)C=2C=C(C=3N(C2)C(N(N3)CC(=O)N(C)C)=O)F)=O)C=C1 Chemical compound C1(CC1)CC(=O)C1=CC=C(O[C@H]2C(N(CC2)C=2C=C(C=3N(C2)C(N(N3)CC(=O)N(C)C)=O)F)=O)C=C1 WSSYGOGBNLYAIM-OAQYLSRUSA-N 0.000 claims 1
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- RHDWPMOPDWBOGA-GOSISDBHSA-N C1(CC1)COC1=CC=C(C=N1)O[C@H]1C(N(CC1)C1=CC=2C(=NN(N2)C)C=C1)=O Chemical compound C1(CC1)COC1=CC=C(C=N1)O[C@H]1C(N(CC1)C1=CC=2C(=NN(N2)C)C=C1)=O RHDWPMOPDWBOGA-GOSISDBHSA-N 0.000 claims 1
- PNAGYNUDTZWUIY-HXUWFJFHSA-N C1(CC1)COC1=CC=C(C=N1)O[C@H]1C(N(CC1)C1=CC=2C(=NN(N2)CC(=O)N(C)C)C=C1)=O Chemical compound C1(CC1)COC1=CC=C(C=N1)O[C@H]1C(N(CC1)C1=CC=2C(=NN(N2)CC(=O)N(C)C)C=C1)=O PNAGYNUDTZWUIY-HXUWFJFHSA-N 0.000 claims 1
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- JVVHBEHMROGHBB-GOSISDBHSA-N C1(CC1)COC1=CC=C(C=N1)O[C@H]1C(N(CC1)C=1C=C(C=2N(C1)C(N(N2)CC(=O)N(C)C)=O)F)=O Chemical compound C1(CC1)COC1=CC=C(C=N1)O[C@H]1C(N(CC1)C=1C=C(C=2N(C1)C(N(N2)CC(=O)N(C)C)=O)F)=O JVVHBEHMROGHBB-GOSISDBHSA-N 0.000 claims 1
- ITPBFKVQPLBWOC-MRXNPFEDSA-N C1(CC1)COC1=CC=C(C=N1)O[C@H]1C(N(CC1)C=1C=C(C=2N(C1)C(N(N2)CC(=O)O)=O)F)=O Chemical compound C1(CC1)COC1=CC=C(C=N1)O[C@H]1C(N(CC1)C=1C=C(C=2N(C1)C(N(N2)CC(=O)O)=O)F)=O ITPBFKVQPLBWOC-MRXNPFEDSA-N 0.000 claims 1
- CBZVBMJMTOTJFX-OAHLLOKOSA-N C1(CC1)COC1=CC=C(C=N1)O[C@H]1C(N(CC1)C=1C=C(C=2N(C1)C(NN2)=O)F)=O Chemical compound C1(CC1)COC1=CC=C(C=N1)O[C@H]1C(N(CC1)C=1C=C(C=2N(C1)C(NN2)=O)F)=O CBZVBMJMTOTJFX-OAHLLOKOSA-N 0.000 claims 1
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| TWI784968B (zh) | 2016-09-09 | 2022-12-01 | 丹麥商西蘭製藥公司 | 澱粉素類似物 |
| AR110988A1 (es) | 2017-02-21 | 2019-05-22 | Sanofi Sa | Compuestos de azetidina como moduladores de gpr119 para el tratamiento de la diabetes, la obesidad, la dislipidemia y trastornos relacionados |
| WO2019043635A1 (en) | 2017-09-01 | 2019-03-07 | Richter Gedeon Nyrt. | COMPOUNDS INHIBITING THE ACTIVITY OF D-AMINO ACID OXIDASE |
| SG11202011883RA (en) * | 2018-05-31 | 2020-12-30 | Hua Medicine Shanghai Ltd | Pharmaceutical combination, composition, and combination formulation containing glucokinase activator and ppar receptor activator, and preparation methods and uses thereof |
| KR102131359B1 (ko) * | 2018-09-07 | 2020-07-07 | 오토텔릭바이오 주식회사 | 안정성이 향상된 의약 조성물 |
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| BR112021024165A2 (pt) | 2019-05-31 | 2022-04-26 | Avolynt | Composições e métodos para o tratamento de doenças metabólicas |
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| US8299070B2 (en) * | 2009-11-25 | 2012-10-30 | Japan Tobacco Inc. | Indole compounds and pharmaceutical use thereof |
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| AU2011202239C1 (en) | 2010-05-19 | 2017-03-16 | Sanofi | Long-acting formulations of insulins |
| US20130184257A1 (en) | 2010-09-17 | 2013-07-18 | Thomas Daniel Aicher | Piperidinyl-substituted lactams as gpr119 modulators |
| CA2853784A1 (en) | 2011-11-11 | 2013-05-16 | Glaxosmithkline Llc | Treatment of blood lipid abnormalities and other conditions |
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