CA2748268C - Compositions for drug administration - Google Patents
Compositions for drug administration Download PDFInfo
- Publication number
- CA2748268C CA2748268C CA2748268A CA2748268A CA2748268C CA 2748268 C CA2748268 C CA 2748268C CA 2748268 A CA2748268 A CA 2748268A CA 2748268 A CA2748268 A CA 2748268A CA 2748268 C CA2748268 C CA 2748268C
- Authority
- CA
- Canada
- Prior art keywords
- composition
- drug
- alkylsaccharide
- maltoside
- less
- 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.)
- Active
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- 239000000203 mixture Substances 0.000 title claims abstract description 248
- 238000001647 drug administration Methods 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 49
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 12
- 239000000952 serotonin receptor agonist Substances 0.000 claims abstract description 12
- 206010027599 migraine Diseases 0.000 claims abstract description 11
- 208000002193 Pain Diseases 0.000 claims abstract description 10
- 230000036407 pain Effects 0.000 claims abstract description 10
- 210000004369 blood Anatomy 0.000 claims description 106
- 239000008280 blood Substances 0.000 claims description 106
- KQKPFRSPSRPDEB-UHFFFAOYSA-N sumatriptan Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 KQKPFRSPSRPDEB-UHFFFAOYSA-N 0.000 claims description 50
- 229960003708 sumatriptan Drugs 0.000 claims description 37
- ZISSAWUMDACLOM-UHFFFAOYSA-N triptane Chemical class CC(C)C(C)(C)C ZISSAWUMDACLOM-UHFFFAOYSA-N 0.000 claims description 29
- NLEBIOOXCVAHBD-QKMCSOCLSA-N dodecyl beta-D-maltoside Chemical group O[C@@H]1[C@@H](O)[C@H](OCCCCCCCCCCCC)O[C@H](CO)[C@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 NLEBIOOXCVAHBD-QKMCSOCLSA-N 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 20
- 230000002829 reductive effect Effects 0.000 claims description 14
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 12
- 229960005254 naratriptan Drugs 0.000 claims description 12
- 230000002459 sustained effect Effects 0.000 claims description 10
- 230000002685 pulmonary effect Effects 0.000 claims description 9
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims description 8
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 claims description 8
- WKEMJKQOLOHJLZ-UHFFFAOYSA-N Almogran Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CS(=O)(=O)N1CCCC1 WKEMJKQOLOHJLZ-UHFFFAOYSA-N 0.000 claims description 7
- 229960002133 almotriptan Drugs 0.000 claims description 7
- 229960002472 eletriptan Drugs 0.000 claims description 7
- OTLDLQZJRFYOJR-LJQANCHMSA-N eletriptan Chemical compound CN1CCC[C@@H]1CC1=CN=C2[C]1C=C(CCS(=O)(=O)C=1C=CC=CC=1)C=C2 OTLDLQZJRFYOJR-LJQANCHMSA-N 0.000 claims description 7
- 229960002284 frovatriptan Drugs 0.000 claims description 7
- SIBNYOSJIXCDRI-SECBINFHSA-N frovatriptan Chemical compound C1=C(C(N)=O)[CH]C2=C(C[C@H](NC)CC3)C3=NC2=C1 SIBNYOSJIXCDRI-SECBINFHSA-N 0.000 claims description 7
- 229960001360 zolmitriptan Drugs 0.000 claims description 7
- UTAZCRNOSWWEFR-ZDUSSCGKSA-N zolmitriptan Chemical compound C=1[C]2C(CCN(C)C)=CN=C2C=CC=1C[C@H]1COC(=O)N1 UTAZCRNOSWWEFR-ZDUSSCGKSA-N 0.000 claims description 7
- 230000036765 blood level Effects 0.000 claims description 5
- UNHGSHHVDNGCFN-UHFFFAOYSA-N naratriptan Chemical compound C=12[CH]C(CCS(=O)(=O)NC)=CC=C2N=CC=1C1CCN(C)CC1 UNHGSHHVDNGCFN-UHFFFAOYSA-N 0.000 claims description 5
- 239000000693 micelle Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 abstract description 264
- -1 alkyl glycoside Chemical class 0.000 abstract description 173
- 229930182470 glycoside Natural products 0.000 abstract description 99
- 238000000034 method Methods 0.000 abstract description 65
- 230000001965 increasing effect Effects 0.000 abstract description 48
- 229940124597 therapeutic agent Drugs 0.000 abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 12
- 229940079593 drug Drugs 0.000 description 229
- 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 description 145
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- 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 91
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 89
- 150000001875 compounds Chemical class 0.000 description 77
- 239000008103 glucose Substances 0.000 description 77
- 229940125396 insulin Drugs 0.000 description 71
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- 238000009472 formulation Methods 0.000 description 66
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- 230000000694 effects Effects 0.000 description 54
- 150000001720 carbohydrates Chemical class 0.000 description 45
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- 239000005720 sucrose Substances 0.000 description 43
- 108010011459 Exenatide Proteins 0.000 description 36
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- 230000003000 nontoxic effect Effects 0.000 description 35
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- 206010012601 diabetes mellitus Diseases 0.000 description 34
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- 235000018102 proteins Nutrition 0.000 description 31
- 239000000243 solution Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 102000051325 Glucagon Human genes 0.000 description 26
- 108060003199 Glucagon Proteins 0.000 description 26
- 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 26
- 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 26
- 229960004666 glucagon Drugs 0.000 description 26
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- 241000700159 Rattus Species 0.000 description 25
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 25
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- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 description 24
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- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 description 22
- 229960003987 melatonin Drugs 0.000 description 22
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 21
- 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 description 21
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- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 17
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| US12/341,696 US8268791B2 (en) | 2004-08-25 | 2008-12-22 | Alkylglycoside compositions for drug administration |
| PCT/US2009/069326 WO2010075465A1 (en) | 2008-12-22 | 2009-12-22 | Compositions for drug administration |
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2008
- 2008-12-22 US US12/341,696 patent/US8268791B2/en active Active
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2009
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- 2009-12-22 WO PCT/US2009/069326 patent/WO2010075465A1/en not_active Ceased
- 2009-12-22 BR BRPI0923403-9A patent/BRPI0923403B1/pt active IP Right Grant
- 2009-12-22 RU RU2011130526/15A patent/RU2554814C2/ru active
- 2009-12-22 EP EP09835809.6A patent/EP2381773B1/en active Active
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- 2009-12-22 CN CN200980157305.0A patent/CN102325450B/zh active Active
- 2009-12-22 KR KR1020117017361A patent/KR101719008B1/ko active Active
- 2009-12-22 DK DK09835809.6T patent/DK2381773T3/en active
- 2009-12-22 JP JP2011542586A patent/JP5752048B2/ja active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| RU2011130526A (ru) | 2013-01-27 |
| US20090163447A1 (en) | 2009-06-25 |
| BRPI0923403A2 (pt) | 2020-08-11 |
| MX2011006790A (es) | 2011-09-27 |
| HK1164059A1 (en) | 2012-09-21 |
| KR20110099049A (ko) | 2011-09-05 |
| MX356271B (es) | 2018-05-21 |
| EP2381773B1 (en) | 2018-02-14 |
| AU2009329952A1 (en) | 2011-07-21 |
| CN102325450A (zh) | 2012-01-18 |
| KR101719008B1 (ko) | 2017-03-22 |
| CA2748268A1 (en) | 2010-07-01 |
| CN102325450B (zh) | 2015-06-17 |
| EP2381773A1 (en) | 2011-11-02 |
| JP2012513412A (ja) | 2012-06-14 |
| BRPI0923403B1 (pt) | 2022-02-08 |
| RU2554814C2 (ru) | 2015-06-27 |
| AU2009329952B2 (en) | 2014-01-09 |
| EP2381773A4 (en) | 2012-12-12 |
| JP2015108008A (ja) | 2015-06-11 |
| DK2381773T3 (en) | 2018-05-28 |
| NZ593782A (en) | 2012-11-30 |
| WO2010075465A1 (en) | 2010-07-01 |
| JP5752048B2 (ja) | 2015-07-22 |
| ES2667248T3 (es) | 2018-05-10 |
| US8268791B2 (en) | 2012-09-18 |
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