NZ534125A - A formulation comprising a GLP-1 compound and a delivery agent - Google Patents
A formulation comprising a GLP-1 compound and a delivery agentInfo
- Publication number
- NZ534125A NZ534125A NZ534125A NZ53412503A NZ534125A NZ 534125 A NZ534125 A NZ 534125A NZ 534125 A NZ534125 A NZ 534125A NZ 53412503 A NZ53412503 A NZ 53412503A NZ 534125 A NZ534125 A NZ 534125A
- Authority
- NZ
- New Zealand
- Prior art keywords
- xaa
- feature
- misc
- glu
- lys
- Prior art date
Links
- 229940124447 delivery agent Drugs 0.000 title claims abstract description 112
- -1 GLP-1 compound Chemical class 0.000 title claims abstract description 86
- 239000000203 mixture Substances 0.000 title claims abstract description 82
- 238000009472 formulation Methods 0.000 title claims abstract description 72
- 102100025101 GATA-type zinc finger protein 1 Human genes 0.000 title claims abstract 21
- 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 title claims abstract 21
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 206
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical class C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims description 141
- 150000001413 amino acids Chemical class 0.000 claims description 128
- 229940024606 amino acid Drugs 0.000 claims description 119
- 239000007983 Tris buffer Substances 0.000 claims description 57
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 53
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 52
- 239000000243 solution Substances 0.000 claims description 52
- 229960002885 histidine Drugs 0.000 claims description 42
- 239000000725 suspension Substances 0.000 claims description 30
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 29
- 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 24
- HNDVDQJCIGZPNO-RXMQYKEDSA-N D-histidine Chemical compound OC(=O)[C@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-RXMQYKEDSA-N 0.000 claims description 19
- 229930195721 D-histidine Natural products 0.000 claims description 19
- JUFFVKRROAPVBI-PVOYSMBESA-N chembl1210015 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=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](CCCCN)C(=O)N[C@@H](CC(=O)N[C@H]1[C@@H]([C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO[C@]3(O[C@@H](C[C@H](O)[C@H](O)CO)[C@H](NC(C)=O)[C@@H](O)C3)C(O)=O)O2)O)[C@@H](CO)O1)NC(C)=O)C(=O)NCC(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)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)CNC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 JUFFVKRROAPVBI-PVOYSMBESA-N 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 229960001519 exenatide Drugs 0.000 claims description 19
- MSECZMWQBBVGEN-LURJTMIESA-N (2s)-2-azaniumyl-4-(1h-imidazol-5-yl)butanoate Chemical compound OC(=O)[C@@H](N)CCC1=CN=CN1 MSECZMWQBBVGEN-LURJTMIESA-N 0.000 claims description 18
- UYEGXSNFZXWSDV-BYPYZUCNSA-N (2s)-3-(2-amino-1h-imidazol-5-yl)-2-azaniumylpropanoate Chemical compound OC(=O)[C@@H](N)CC1=CNC(N)=N1 UYEGXSNFZXWSDV-BYPYZUCNSA-N 0.000 claims description 18
- 108010011459 Exenatide Proteins 0.000 claims description 18
- ZCKYOWGFRHAZIQ-UHFFFAOYSA-N dihydrourocanic acid Chemical compound OC(=O)CCC1=CNC=N1 ZCKYOWGFRHAZIQ-UHFFFAOYSA-N 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 239000003755 preservative agent Substances 0.000 claims description 13
- 102000004877 Insulin Human genes 0.000 claims description 12
- 108090001061 Insulin Proteins 0.000 claims description 12
- 229940125396 insulin Drugs 0.000 claims description 12
- 108010015174 exendin 3 Proteins 0.000 claims description 10
- LMHMJYMCGJNXRS-IOPUOMRJSA-N exendin-3 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=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](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)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](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@H](C)O)[C@H](C)O)C(C)C)C1=CC=CC=C1 LMHMJYMCGJNXRS-IOPUOMRJSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 230000002335 preservative effect Effects 0.000 claims description 10
- KZNQNBZMBZJQJO-UHFFFAOYSA-N N-glycyl-L-proline Natural products NCC(=O)N1CCCC1C(O)=O KZNQNBZMBZJQJO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 239000000872 buffer Substances 0.000 claims description 8
- KZNQNBZMBZJQJO-YFKPBYRVSA-N glyclproline Chemical compound NCC(=O)N1CCC[C@H]1C(O)=O KZNQNBZMBZJQJO-YFKPBYRVSA-N 0.000 claims description 8
- 108010077515 glycylproline Proteins 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 239000006184 cosolvent Substances 0.000 claims description 7
- 239000002245 particle Substances 0.000 claims description 7
- 239000000375 suspending agent Substances 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 2
- 206010056997 Impaired fasting glucose Diseases 0.000 claims description 2
- 206010033645 Pancreatitis Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 230000001925 catabolic effect Effects 0.000 claims description 2
- 201000006549 dyspepsia Diseases 0.000 claims description 2
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- 239000003826 tablet Substances 0.000 claims description 2
- AJFGLTPLWPTALJ-SSDOTTSWSA-N (2s)-2-azaniumyl-2-(fluoromethyl)-3-(1h-imidazol-5-yl)propanoate Chemical compound FC[C@@](N)(C(O)=O)CC1=CN=CN1 AJFGLTPLWPTALJ-SSDOTTSWSA-N 0.000 claims 9
- HRRYYCWYCMJNGA-ZETCQYMHSA-N alpha-methyl-L-histidine Chemical compound OC(=O)[C@](N)(C)CC1=CN=CN1 HRRYYCWYCMJNGA-ZETCQYMHSA-N 0.000 claims 9
- IVDFVBVIVLJJHR-LKXGYXEUSA-N Thr-Ser-Asp Chemical compound [H]N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(O)=O IVDFVBVIVLJJHR-LKXGYXEUSA-N 0.000 claims 8
- HPJLZFTUUJKWAJ-JHEQGTHGSA-N Glu-Gly-Thr Chemical compound [H]N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(O)=O HPJLZFTUUJKWAJ-JHEQGTHGSA-N 0.000 claims 7
- KQMBIBBJWXGSEI-ROLXFIACSA-N (2s)-2-amino-3-hydroxy-3-(1h-imidazol-5-yl)propanoic acid Chemical compound OC(=O)[C@@H](N)C(O)C1=CNC=N1 KQMBIBBJWXGSEI-ROLXFIACSA-N 0.000 claims 6
- 230000009435 amidation Effects 0.000 claims 6
- 238000007112 amidation reaction Methods 0.000 claims 6
- YXXPVUOMPSZURS-ZLIFDBKOSA-N Ala-Trp-Leu Chemical compound C1=CC=C2C(C[C@@H](C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@H](C)N)=CNC2=C1 YXXPVUOMPSZURS-ZLIFDBKOSA-N 0.000 claims 4
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- GNRMAQSIROFNMI-IXOXFDKPSA-N Phe-Thr-Ser Chemical compound [H]N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(O)=O GNRMAQSIROFNMI-IXOXFDKPSA-N 0.000 claims 4
- OLKICIBQRVSQMA-SRVKXCTJSA-N Ser-Ser-Tyr Chemical compound [H]N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC1=CC=C(O)C=C1)C(O)=O OLKICIBQRVSQMA-SRVKXCTJSA-N 0.000 claims 4
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- 108010080629 tryptophan-leucine Proteins 0.000 claims 4
- LLWQVJNHMYBLLK-CDMKHQONSA-N Gly-Thr-Phe Chemical compound [H]NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O LLWQVJNHMYBLLK-CDMKHQONSA-N 0.000 claims 3
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- FJVAQLJNTSUQPY-CIUDSAMLSA-N Ala-Ala-Lys Chemical compound C[C@H](N)C(=O)N[C@@H](C)C(=O)N[C@H](C(O)=O)CCCCN FJVAQLJNTSUQPY-CIUDSAMLSA-N 0.000 claims 2
- IIAXFBUTKIDDIP-ULQDDVLXSA-N Arg-Leu-Phe Chemical compound [H]N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O IIAXFBUTKIDDIP-ULQDDVLXSA-N 0.000 claims 2
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- 241000270449 Heloderma sp. Species 0.000 claims 2
- NEEOBPIXKWSBRF-IUCAKERBSA-N Leu-Glu-Gly Chemical compound [H]N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(O)=O NEEOBPIXKWSBRF-IUCAKERBSA-N 0.000 claims 2
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- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
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- 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
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Environmental Sciences (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
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Applications Claiming Priority (2)
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| US35818402P | 2002-02-20 | 2002-02-20 | |
| PCT/US2003/003111 WO2003072195A2 (en) | 2002-02-20 | 2003-02-07 | Method for administering glp-1 molecules |
Publications (1)
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| NZ534125A true NZ534125A (en) | 2006-11-30 |
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| Application Number | Title | Priority Date | Filing Date |
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| NZ534125A NZ534125A (en) | 2002-02-20 | 2003-02-07 | A formulation comprising a GLP-1 compound and a delivery agent |
Country Status (16)
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| RU (1) | RU2332229C2 (https=) |
| WO (1) | WO2003072195A2 (https=) |
| ZA (1) | ZA200406626B (https=) |
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| GB0621576D0 (en) | 2006-10-30 | 2006-12-06 | Reckitt Benckiser Nv | Device status indicator |
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2003
- 2003-02-07 PL PL371736A patent/PL209734B1/pl unknown
- 2003-02-07 RU RU2004127916/15A patent/RU2332229C2/ru not_active Application Discontinuation
- 2003-02-07 ES ES03707669.2T patent/ES2614603T3/es not_active Expired - Lifetime
- 2003-02-07 JP JP2003570937A patent/JP4417113B2/ja not_active Expired - Fee Related
- 2003-02-07 EP EP11186033.4A patent/EP2409569B1/en not_active Expired - Lifetime
- 2003-02-07 BR BR0307727-6A patent/BR0307727A/pt active Search and Examination
- 2003-02-07 KR KR10-2004-7012920A patent/KR20040085205A/ko not_active Ceased
- 2003-02-07 CA CA2473340A patent/CA2473340C/en not_active Expired - Fee Related
- 2003-02-07 AU AU2003208945A patent/AU2003208945B2/en not_active Ceased
- 2003-02-07 US US10/504,717 patent/US20050148497A1/en not_active Abandoned
- 2003-02-07 WO PCT/US2003/003111 patent/WO2003072195A2/en not_active Ceased
- 2003-02-07 EP EP03707669.2A patent/EP1478233B1/en not_active Expired - Lifetime
- 2003-02-07 CN CNB038043653A patent/CN1332711C/zh not_active Expired - Fee Related
- 2003-02-07 KR KR1020117007409A patent/KR101165431B1/ko not_active Expired - Fee Related
- 2003-02-07 NZ NZ534125A patent/NZ534125A/en not_active IP Right Cessation
- 2003-02-07 MX MXPA04008068A patent/MXPA04008068A/es active IP Right Grant
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2004
- 2004-07-29 IL IL163278A patent/IL163278A/en active IP Right Revival
- 2004-08-19 ZA ZA2004/06626A patent/ZA200406626B/en unknown
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2009
- 2009-04-09 US US12/421,590 patent/US7939494B2/en not_active Expired - Fee Related
- 2009-10-05 JP JP2009231896A patent/JP5657230B2/ja not_active Expired - Fee Related
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2011
- 2011-01-12 US US13/004,964 patent/US8492330B2/en not_active Expired - Fee Related
-
2013
- 2013-07-16 US US13/943,610 patent/US20140005106A1/en not_active Abandoned
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2014
- 2014-01-05 IL IL230315A patent/IL230315A/en active IP Right Grant
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2015
- 2015-01-22 US US14/603,239 patent/US20150202296A1/en not_active Abandoned
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