JP2014510739A - 新規のグルカゴン類似体 - Google Patents
新規のグルカゴン類似体 Download PDFInfo
- Publication number
- JP2014510739A JP2014510739A JP2014501586A JP2014501586A JP2014510739A JP 2014510739 A JP2014510739 A JP 2014510739A JP 2014501586 A JP2014501586 A JP 2014501586A JP 2014501586 A JP2014501586 A JP 2014501586A JP 2014510739 A JP2014510739 A JP 2014510739A
- Authority
- JP
- Japan
- Prior art keywords
- carboxybutanoyl
- amino
- glucagon
- compound
- acetamido
- 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- Withdrawn
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- MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical class 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 title description 86
- 108060003199 Glucagon Proteins 0.000 claims abstract description 355
- 150000001875 compounds Chemical class 0.000 claims abstract description 177
- 102000051325 Glucagon Human genes 0.000 claims abstract description 63
- 239000003814 drug Substances 0.000 claims abstract description 46
- 208000008589 Obesity Diseases 0.000 claims abstract description 28
- 235000020824 obesity Nutrition 0.000 claims abstract description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 23
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 21
- 201000010099 disease Diseases 0.000 claims abstract description 18
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 12
- 201000001421 hyperglycemia Diseases 0.000 claims abstract description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 601
- 229960004666 glucagon Drugs 0.000 claims description 211
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 158
- -1 succinoyl moiety Chemical group 0.000 claims description 94
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 87
- 125000001424 substituent group Chemical group 0.000 claims description 67
- 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 59
- 208000013016 Hypoglycemia Diseases 0.000 claims description 58
- 150000001413 amino acids Chemical class 0.000 claims description 58
- 239000008194 pharmaceutical composition Substances 0.000 claims description 58
- 230000002218 hypoglycaemic effect Effects 0.000 claims description 50
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 31
- 125000003275 alpha amino acid group Chemical group 0.000 claims description 31
- 101100285000 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) his-3 gene Proteins 0.000 claims description 30
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 30
- 125000000539 amino acid group Chemical group 0.000 claims description 29
- 102000004877 Insulin Human genes 0.000 claims description 28
- 108090001061 Insulin Proteins 0.000 claims description 28
- 229940125396 insulin Drugs 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 28
- 238000002360 preparation method Methods 0.000 claims description 23
- 238000006467 substitution reaction Methods 0.000 claims description 23
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 21
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 21
- 229940079593 drug Drugs 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 19
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 15
- 125000001992 L-gamma-glutamyl group Chemical group N[C@@H](CCC(=O)*)C(=O)O 0.000 claims description 13
- 150000001408 amides Chemical class 0.000 claims description 13
- 230000002496 gastric effect Effects 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 206010033307 Overweight Diseases 0.000 claims description 11
- 238000007911 parenteral administration Methods 0.000 claims description 10
- 230000037396 body weight Effects 0.000 claims description 9
- 208000032841 Bulimia Diseases 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 7
- 230000037406 food intake Effects 0.000 claims description 7
- 235000012631 food intake Nutrition 0.000 claims description 7
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 7
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 6
- 206010019708 Hepatic steatosis Diseases 0.000 claims description 6
- 206010020772 Hypertension Diseases 0.000 claims description 6
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 6
- 239000002876 beta blocker Substances 0.000 claims description 6
- 229940097320 beta blocking agent Drugs 0.000 claims description 6
- 208000029078 coronary artery disease Diseases 0.000 claims description 6
- 230000004584 weight gain Effects 0.000 claims description 6
- 235000019786 weight gain Nutrition 0.000 claims description 6
- 230000004580 weight loss Effects 0.000 claims description 6
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 5
- 206010012335 Dependence Diseases 0.000 claims description 5
- 206010061818 Disease progression Diseases 0.000 claims description 5
- 235000019789 appetite Nutrition 0.000 claims description 5
- 230000036528 appetite Effects 0.000 claims description 5
- 230000005750 disease progression Effects 0.000 claims description 5
- 206010022498 insulinoma Diseases 0.000 claims description 5
- 208000021255 pancreatic insulinoma Diseases 0.000 claims description 5
- 230000035935 pregnancy Effects 0.000 claims description 5
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims description 4
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 claims description 4
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims description 4
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims description 4
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 claims description 4
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 claims description 4
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 claims description 4
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 claims description 4
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 claims description 4
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 claims description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims description 4
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 claims description 4
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 claims description 4
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 claims description 4
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 claims description 4
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 claims description 4
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 claims description 4
- KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 claims description 4
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 claims description 4
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 claims description 4
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 claims description 4
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims description 4
- WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 claims description 4
- FQMZXMVHHKXGTM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCNCCO)=CC=C21 FQMZXMVHHKXGTM-UHFFFAOYSA-N 0.000 claims description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/605—Glucagons
-
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Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
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| US201161468285P | 2011-03-28 | 2011-03-28 | |
| EP11159967.6 | 2011-03-28 | ||
| EP11159967 | 2011-03-28 | ||
| US61/468,285 | 2011-03-28 | ||
| EP11182475.1 | 2011-09-23 | ||
| EP11182475 | 2011-09-23 | ||
| US201161539128P | 2011-09-26 | 2011-09-26 | |
| US61/539,128 | 2011-09-26 | ||
| PCT/EP2012/055481 WO2012130866A1 (en) | 2011-03-28 | 2012-03-28 | Novel glucagon analogues |
Publications (2)
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| JP2014510739A true JP2014510739A (ja) | 2014-05-01 |
| JP2014510739A5 JP2014510739A5 (https=) | 2015-05-07 |
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| JP2014501586A Withdrawn JP2014510739A (ja) | 2011-03-28 | 2012-03-28 | 新規のグルカゴン類似体 |
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| US (2) | US20140031278A1 (https=) |
| EP (1) | EP2691108A1 (https=) |
| JP (1) | JP2014510739A (https=) |
| KR (1) | KR20140020292A (https=) |
| CN (1) | CN103596583B (https=) |
| AU (1) | AU2012234276A1 (https=) |
| BR (1) | BR112013024076A2 (https=) |
| CA (1) | CA2830974A1 (https=) |
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| RU (1) | RU2013145013A (https=) |
| WO (1) | WO2012130866A1 (https=) |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014527975A (ja) * | 2011-09-23 | 2014-10-23 | ノヴォ ノルディスク アー／エス | 新規のグルカゴン類似体 |
| US9751927B2 (en) | 2013-04-18 | 2017-09-05 | Novo Nordisk A/S | Stable, protracted GLP-1/glucagon receptor co-agonists for medical use |
| US10570184B2 (en) | 2014-06-04 | 2020-02-25 | Novo Nordisk A/S | GLP-1/glucagon receptor co-agonists for medical use |
| JP2021511386A (ja) * | 2018-01-23 | 2021-05-06 | ゼリス ファーマシューティカルズ インコーポレイテッド | 低用量の安定なグルカゴンを使用する肥満治療手術後の低血糖症の処置 |
| JP2022519620A (ja) * | 2019-02-05 | 2022-03-24 | イーライ リリー アンド カンパニー | グルカゴン類似体アゴニストおよびその使用方法 |
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| US8515257B2 (en) * | 2007-10-17 | 2013-08-20 | International Business Machines Corporation | Automatic announcer voice attenuation in a presentation of a televised sporting event |
| AP3329A (en) | 2009-07-13 | 2015-06-30 | Zealand Pharma As | Acylated glucagon analogues |
| JP6228187B2 (ja) | 2012-05-03 | 2017-11-08 | ジーランド ファーマ アクティーゼルスカブ | Ｇｉｐ−ｇｌｐ−１デュアルアゴニスト化合物及び方法 |
| AU2013295035B2 (en) | 2012-07-23 | 2017-08-03 | Zealand Pharma A/S | Glucagon analogues |
| TWI608013B (zh) | 2012-09-17 | 2017-12-11 | 西蘭製藥公司 | 升糖素類似物 |
| WO2015055801A1 (en) | 2013-10-17 | 2015-04-23 | Zealand Pharma A/S | Acylated glucagon analogues |
| US9988429B2 (en) | 2013-10-17 | 2018-06-05 | Zealand Pharma A/S | Glucagon analogues |
| MX2016005556A (es) | 2013-11-06 | 2016-07-15 | Zealand Pharma As | Compuestos agonistas duales de gip-glp-1 y procedimientos. |
| AU2014345570B2 (en) | 2013-11-06 | 2019-01-24 | Zealand Pharma A/S | Glucagon-GLP-1-GIP triple agonist compounds |
| AR098616A1 (es) | 2013-12-18 | 2016-06-01 | Lilly Co Eli | Péptido para el tratamiento de hipoglicemia severa |
| WO2015124612A1 (en) * | 2014-02-18 | 2015-08-27 | Novo Nordisk A/S | Stable glucagon analogues and use for treatment of hypoglycaemia |
| US10253078B2 (en) | 2014-10-29 | 2019-04-09 | Zealand Pharma A/S | GIP agonist compounds and methods |
| EA034820B1 (ru) | 2015-02-17 | 2020-03-25 | Эли Лилли Энд Компани | Порошковый состав для интраназального введения для лечения гипогликемии |
| US10336802B2 (en) | 2015-04-16 | 2019-07-02 | Zealand Pharma A/S | Acylated glucagon analogue |
| TWI622596B (zh) | 2015-10-26 | 2018-05-01 | 美國禮來大藥廠 | 升糖素受體促效劑 |
| CN111683675A (zh) * | 2017-12-07 | 2020-09-18 | 阿道恰公司 | 包含人胰高血糖素和共聚氨基酸的呈可注射水溶液形式的组合物 |
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2012
- 2012-03-28 JP JP2014501586A patent/JP2014510739A/ja not_active Withdrawn
- 2012-03-28 EP EP12710748.0A patent/EP2691108A1/en not_active Withdrawn
- 2012-03-28 KR KR1020137027799A patent/KR20140020292A/ko not_active Withdrawn
- 2012-03-28 CA CA2830974A patent/CA2830974A1/en not_active Withdrawn
- 2012-03-28 CN CN201280015759.6A patent/CN103596583B/zh not_active Expired - Fee Related
- 2012-03-28 US US13/984,185 patent/US20140031278A1/en not_active Abandoned
- 2012-03-28 AU AU2012234276A patent/AU2012234276A1/en not_active Withdrawn
- 2012-03-28 MX MX2013011175A patent/MX2013011175A/es unknown
- 2012-03-28 BR BR112013024076A patent/BR112013024076A2/pt not_active IP Right Cessation
- 2012-03-28 WO PCT/EP2012/055481 patent/WO2012130866A1/en not_active Ceased
- 2012-03-28 RU RU2013145013/04A patent/RU2013145013A/ru unknown
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2013
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- 2013-08-29 ZA ZA2013/06514A patent/ZA201306514B/en unknown
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2015
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014527975A (ja) * | 2011-09-23 | 2014-10-23 | ノヴォ ノルディスク アー／エス | 新規のグルカゴン類似体 |
| US9751927B2 (en) | 2013-04-18 | 2017-09-05 | Novo Nordisk A/S | Stable, protracted GLP-1/glucagon receptor co-agonists for medical use |
| US10570184B2 (en) | 2014-06-04 | 2020-02-25 | Novo Nordisk A/S | GLP-1/glucagon receptor co-agonists for medical use |
| JP2021511386A (ja) * | 2018-01-23 | 2021-05-06 | ゼリス ファーマシューティカルズ インコーポレイテッド | 低用量の安定なグルカゴンを使用する肥満治療手術後の低血糖症の処置 |
| JP7444786B2 (ja) | 2018-01-23 | 2024-03-06 | ゼリス ファーマシューティカルズ インコーポレイテッド | 低用量の安定なグルカゴンを使用する肥満治療手術後の低血糖症の処置 |
| JP2022519620A (ja) * | 2019-02-05 | 2022-03-24 | イーライ リリー アンド カンパニー | グルカゴン類似体アゴニストおよびその使用方法 |
| JP7212171B2 (ja) | 2019-02-05 | 2023-01-24 | イーライ リリー アンド カンパニー | グルカゴン類似体アゴニストおよびその使用方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20140020292A (ko) | 2014-02-18 |
| BR112013024076A2 (pt) | 2016-12-06 |
| IL227869A0 (en) | 2013-09-30 |
| US20140031278A1 (en) | 2014-01-30 |
| WO2012130866A1 (en) | 2012-10-04 |
| CA2830974A1 (en) | 2012-10-04 |
| AU2012234276A1 (en) | 2013-08-29 |
| CN103596583A (zh) | 2014-02-19 |
| MX2013011175A (es) | 2013-11-01 |
| EP2691108A1 (en) | 2014-02-05 |
| ZA201306514B (en) | 2014-05-28 |
| US20150368313A1 (en) | 2015-12-24 |
| RU2013145013A (ru) | 2015-05-10 |
| CN103596583B (zh) | 2016-07-27 |
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