CA2777899C

CA2777899C - Composition for inhalation comprising a pharmaceutically acceptable glassy matrix

Composition for inhalation comprising a pharmaceutically acceptable glassy matrix Download PDF

Info

Publication number: CA2777899C
Authority: CA; Canada
Prior art keywords: composition; metal ion; calcium lactate; ion salt; composition according
Prior art date: 2009-10-21
Legal status : Active

Application number

CA2777899A

Other languages

English (en)

French (fr)

Other versions

CA2777899A1 (en

Inventor

Glen Martyn

Current Assignee

Innovata Ltd

Original Assignee

Innovata Ltd

Priority date

2009-10-21

Filing date

2010-10-21

Publication date

2016-03-29

2010-10-21 Application filed by Innovata Ltd filed Critical Innovata Ltd

2011-04-28 Publication of CA2777899A1 publication Critical patent/CA2777899A1/en

2016-03-29 Application granted granted Critical

2016-03-29 Publication of CA2777899C publication Critical patent/CA2777899C/en

Status Active legal-status Critical Current

2030-10-21 Anticipated expiration legal-status Critical

Links

239000000203 mixture Substances 0.000 title claims abstract description 284
239000011159 matrix material Substances 0.000 title claims abstract description 40
150000003839 salts Chemical class 0.000 claims abstract description 216
229910021645 metal ion Inorganic materials 0.000 claims abstract description 170
239000002245 particle Substances 0.000 claims abstract description 142
239000000463 material Substances 0.000 claims abstract description 110
239000000843 powder Substances 0.000 claims abstract description 109
230000000975 bioactive effect Effects 0.000 claims abstract description 89
229920005862 polyol Polymers 0.000 claims abstract description 15
150000003077 polyols Chemical class 0.000 claims abstract description 15
MKJXYGKVIBWPFZ-UHFFFAOYSA-L calcium lactate Chemical group [Ca+2].CC(O)C([O-])=O.CC(O)C([O-])=O MKJXYGKVIBWPFZ-UHFFFAOYSA-L 0.000 claims description 63
239000001527 calcium lactate Substances 0.000 claims description 63
229960002401 calcium lactate Drugs 0.000 claims description 63
235000011086 calcium lactate Nutrition 0.000 claims description 63
238000000034 method Methods 0.000 claims description 63
229910001868 water Inorganic materials 0.000 claims description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
238000007496 glass forming Methods 0.000 claims description 18
230000036571 hydration Effects 0.000 claims description 17
238000006703 hydration reaction Methods 0.000 claims description 17
238000001694 spray drying Methods 0.000 claims description 17
239000006185 dispersion Substances 0.000 claims description 15
239000000243 solution Substances 0.000 claims description 14
230000002776 aggregation Effects 0.000 claims description 13
238000005054 agglomeration Methods 0.000 claims description 12
108090000765 processed proteins & peptides Proteins 0.000 claims description 12
108090000623 proteins and genes Proteins 0.000 claims description 11
150000003431 steroids Chemical class 0.000 claims description 11
239000000126 substance Substances 0.000 claims description 11
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims description 10
229920000669 heparin Polymers 0.000 claims description 10
102000004169 proteins and genes Human genes 0.000 claims description 10
230000002685 pulmonary effect Effects 0.000 claims description 10
229960005486 vaccine Drugs 0.000 claims description 10
PWKNEBQRTUXXLT-ZBHRUSISSA-L calcium lactate gluconate Chemical compound [Ca+2].CC(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O PWKNEBQRTUXXLT-ZBHRUSISSA-L 0.000 claims description 9
229940041131 calcium lactate gluconate Drugs 0.000 claims description 9
XHHXAYSRQQBVFL-UHFFFAOYSA-L calcium;3-carboxy-3-hydroxypentanedioate;2-hydroxypropanoic acid Chemical compound [Ca+2].CC(O)C([O-])=O.OC(=O)CC(O)(C(O)=O)CC([O-])=O XHHXAYSRQQBVFL-UHFFFAOYSA-L 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 9
102000004196 processed proteins & peptides Human genes 0.000 claims description 8
208000023504 respiratory system disease Diseases 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
230000001965 increasing effect Effects 0.000 claims description 7
229960002897 heparin Drugs 0.000 claims description 6
102000004190 Enzymes Human genes 0.000 claims description 5
108090000790 Enzymes Proteins 0.000 claims description 5
229940057801 calcium lactate pentahydrate Drugs 0.000 claims description 5
JCFHGKRSYPTRSS-UHFFFAOYSA-N calcium;2-hydroxypropanoic acid;hydrate Chemical compound O.[Ca].CC(O)C(O)=O JCFHGKRSYPTRSS-UHFFFAOYSA-N 0.000 claims description 5
229920001184 polypeptide Polymers 0.000 claims description 5
239000000556 agonist Substances 0.000 claims description 4
150000004683 dihydrates Chemical class 0.000 claims description 4
239000000839 emulsion Substances 0.000 claims description 4
ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 claims description 4
229960001008 heparin sodium Drugs 0.000 claims description 4
239000003018 immunosuppressive agent Substances 0.000 claims description 4
230000000069 prophylactic effect Effects 0.000 claims description 4
239000006104 solid solution Substances 0.000 claims description 4
239000000725 suspension Substances 0.000 claims description 4
230000001225 therapeutic effect Effects 0.000 claims description 4
LERNTVKEWCAPOY-VOGVJGKGSA-N C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 Chemical compound C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 LERNTVKEWCAPOY-VOGVJGKGSA-N 0.000 claims description 3
PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 3
229930105110 Cyclosporin A Natural products 0.000 claims description 3
108010036949 Cyclosporine Proteins 0.000 claims description 3
QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 claims description 3
229960001265 ciclosporin Drugs 0.000 claims description 3
229960003444 immunosuppressant agent Drugs 0.000 claims description 3
229960001967 tacrolimus Drugs 0.000 claims description 3
QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 claims description 3
229960000257 tiotropium bromide Drugs 0.000 claims description 3
229930182912 cyclosporin Natural products 0.000 claims description 2
241000284466 Antarctothoa delta Species 0.000 claims 3
230000001861 immunosuppressant effect Effects 0.000 claims 1
-1 monosaccharide sugar alcohols Chemical class 0.000 description 97
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 58
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
150000001875 compounds Chemical class 0.000 description 45
239000011859 microparticle Substances 0.000 description 40
229910052739 hydrogen Inorganic materials 0.000 description 33
HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 32
HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 32
HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 32
239000001257 hydrogen Substances 0.000 description 32
229940074410 trehalose Drugs 0.000 description 32
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 31
102000004877 Insulin Human genes 0.000 description 30
108090001061 Insulin Proteins 0.000 description 30
229940125396 insulin Drugs 0.000 description 28
239000000546 pharmaceutical excipient Substances 0.000 description 27
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 24
229910052731 fluorine Chemical group 0.000 description 24
239000011737 fluorine Chemical group 0.000 description 24
208000006673 asthma Diseases 0.000 description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
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 description 20
238000009472 formulation Methods 0.000 description 19
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 17
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 17
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 16
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 16
GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 description 16
239000008186 active pharmaceutical agent Substances 0.000 description 16
NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 16
239000011521 glass Substances 0.000 description 16
150000002431 hydrogen Chemical class 0.000 description 16
239000003814 drug Substances 0.000 description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
229960004017 salmeterol Drugs 0.000 description 15
LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical compound O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 description 15
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BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 description 14
229910052736 halogen Chemical group 0.000 description 14
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GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 13
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 13
238000000113 differential scanning calorimetry Methods 0.000 description 13
229960002848 formoterol Drugs 0.000 description 13
239000008101 lactose Substances 0.000 description 13
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239000001509 sodium citrate Substances 0.000 description 13
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 13
238000001035 drying Methods 0.000 description 12
239000006260 foam Substances 0.000 description 12
FIMXSEMBHGTNKT-UHFFFAOYSA-N Scopine Natural products CN1C2CC(O)CC1C1C2O1 FIMXSEMBHGTNKT-UHFFFAOYSA-N 0.000 description 11
230000000996 additive effect Effects 0.000 description 11
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229960000289 fluticasone propionate Drugs 0.000 description 11
WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 description 11
150000002367 halogens Chemical group 0.000 description 11
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
229910052794 bromium Inorganic materials 0.000 description 10
125000004432 carbon atom Chemical group C* 0.000 description 10
239000012876 carrier material Substances 0.000 description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
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210000003097 mucus Anatomy 0.000 description 10
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 10
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238000007792 addition Methods 0.000 description 9
229960005069 calcium Drugs 0.000 description 9
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150000004684 trihydrates Chemical class 0.000 description 9
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 8
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
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KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 7
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VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
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QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
229960004436 budesonide Drugs 0.000 description 6
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 6
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
229960002052 salbutamol Drugs 0.000 description 6
FIMXSEMBHGTNKT-RZVDLVGDSA-N scopine Chemical compound C([C@@H]1N2C)[C@H](O)C[C@@H]2[C@@H]2[C@H]1O2 FIMXSEMBHGTNKT-RZVDLVGDSA-N 0.000 description 6
229910052725 zinc Inorganic materials 0.000 description 6
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XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 5
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