JP7162675B2 - 注射用組成物 - Google Patents
注射用組成物 Download PDFInfo
- Publication number
- JP7162675B2 JP7162675B2 JP2020549451A JP2020549451A JP7162675B2 JP 7162675 B2 JP7162675 B2 JP 7162675B2 JP 2020549451 A JP2020549451 A JP 2020549451A JP 2020549451 A JP2020549451 A JP 2020549451A JP 7162675 B2 JP7162675 B2 JP 7162675B2
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- Prior art keywords
- peptide
- freeze
- seq
- cyclodextrin
- amino acid
- Prior art date
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- TUCIOBMMDDOEMM-RIYZIHGNSA-N tyrphostin B42 Chemical compound C1=C(O)C(O)=CC=C1\C=C(/C#N)C(=O)NCC1=CC=CC=C1 TUCIOBMMDDOEMM-RIYZIHGNSA-N 0.000 description 1
- 229950009811 ubenimex Drugs 0.000 description 1
- 229950007775 umirolimus Drugs 0.000 description 1
- AHXICHPPXIGCBN-GPWPDEGDSA-N uqc681jjiv Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](OC(C)=O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)OC)C(=O)C1=CC=CC=C1 AHXICHPPXIGCBN-GPWPDEGDSA-N 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 206010046766 uterine cancer Diseases 0.000 description 1
- 208000024719 uterine cervix neoplasm Diseases 0.000 description 1
- 229960002004 valdecoxib Drugs 0.000 description 1
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 1
- 125000002987 valine group Chemical group [H]N([H])C([H])(C(*)=O)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960000241 vandetanib Drugs 0.000 description 1
- UHTHHESEBZOYNR-UHFFFAOYSA-N vandetanib Chemical compound COC1=CC(C(/N=CN2)=N/C=3C(=CC(Br)=CC=3)F)=C2C=C1OCC1CCN(C)CC1 UHTHHESEBZOYNR-UHFFFAOYSA-N 0.000 description 1
- 229950010644 vidofludimus Drugs 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- 229960004982 vinblastine sulfate Drugs 0.000 description 1
- KDQAABAKXDWYSZ-PNYVAJAMSA-N vinblastine sulfate Chemical compound OS(O)(=O)=O.C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 KDQAABAKXDWYSZ-PNYVAJAMSA-N 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- 229960002110 vincristine sulfate Drugs 0.000 description 1
- AQTQHPDCURKLKT-JKDPCDLQSA-N vincristine sulfate Chemical compound OS(O)(=O)=O.C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C=O)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 AQTQHPDCURKLKT-JKDPCDLQSA-N 0.000 description 1
- 229960004355 vindesine Drugs 0.000 description 1
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
- 229960005212 vindesine sulfate Drugs 0.000 description 1
- 229960000922 vinflunine Drugs 0.000 description 1
- NMDYYWFGPIMTKO-HBVLKOHWSA-N vinflunine Chemical compound C([C@@](C1=C(C2=CC=CC=C2N1)C1)(C2=C(OC)C=C3N(C)[C@@H]4[C@@]5(C3=C2)CCN2CC=C[C@]([C@@H]52)([C@H]([C@]4(O)C(=O)OC)OC(C)=O)CC)C(=O)OC)[C@H]2C[C@@H](C(C)(F)F)CN1C2 NMDYYWFGPIMTKO-HBVLKOHWSA-N 0.000 description 1
- 229960002066 vinorelbine Drugs 0.000 description 1
- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
- 229950005839 vinzolidine Drugs 0.000 description 1
- 229950001212 volociximab Drugs 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 229960000237 vorinostat Drugs 0.000 description 1
- 229960001771 vorozole Drugs 0.000 description 1
- XLMPPFTZALNBFS-INIZCTEOSA-N vorozole Chemical compound C1([C@@H](C2=CC=C3N=NN(C3=C2)C)N2N=CN=C2)=CC=C(Cl)C=C1 XLMPPFTZALNBFS-INIZCTEOSA-N 0.000 description 1
- ORXQGKIUCDPEAJ-YRNVUSSQSA-N xanthohumol Chemical compound COC1=CC(O)=C(CC=C(C)C)C(O)=C1C(=O)\C=C\C1=CC=C(O)C=C1 ORXQGKIUCDPEAJ-YRNVUSSQSA-N 0.000 description 1
- UVBDKJHYMQEAQV-UHFFFAOYSA-N xanthohumol Natural products OC1=C(CC=C(C)C)C(OC)=CC(OC)=C1C(=O)C=CC1=CC=C(O)C=C1 UVBDKJHYMQEAQV-UHFFFAOYSA-N 0.000 description 1
- 235000008209 xanthohumol Nutrition 0.000 description 1
- 229950004227 zaltoprofen Drugs 0.000 description 1
- 229950008250 zalutumumab Drugs 0.000 description 1
- 229950009002 zanolimumab Drugs 0.000 description 1
- RPQZTTQVRYEKCR-WCTZXXKLSA-N zebularine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N=CC=C1 RPQZTTQVRYEKCR-WCTZXXKLSA-N 0.000 description 1
- SUPVGFZUWFMATN-UHFFFAOYSA-N zelavespib Chemical compound N1=CN=C2N(CCCNC(C)C)C(SC=3C(=CC=4OCOC=4C=3)I)=NC2=C1N SUPVGFZUWFMATN-UHFFFAOYSA-N 0.000 description 1
- 229950009268 zinostatin Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/10—Peptides having 12 to 20 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/0005—Vertebrate antigens
- A61K39/0011—Cancer antigens
- A61K39/001152—Transcription factors, e.g. SOX or c-MYC
- A61K39/001153—Wilms tumor 1 [WT1]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/40—Cyclodextrins; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
- A61K2039/55511—Organic adjuvants
- A61K2039/55566—Emulsions, e.g. Freund's adjuvant, MF59
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/70—Multivalent vaccine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/82—Translation products from oncogenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K19/00—Hybrid peptides, i.e. peptides covalently bound to nucleic acids, or non-covalently bound protein-protein complexes
Description
RMFPNAPYL (配列番号:2)、
CMTWNQMNL (配列番号:3)、
CYTWNQMNL (配列番号:4)、
ALLPAVPSL (配列番号:5)、
SLGEQQYSV (配列番号:6)、
RVPGVAPTL (配列番号:7)、
VLDFAPPGA (配列番号:8)、
C-CMTWNQMNL (配列番号:9)(式中、CとCの間の結合はジスルフィド結合を表す。)、
C-CYTWNQMNL (配列番号:10)(式中、CとCの間の結合はジスルフィド結合を表す。)、
KRYFKLSHLQMHSRKH (配列番号:11)、
SGQARMFPNAPYLPSCLES (配列番号:12)、
RSDELVRHHNMHQRNMTKL (配列番号:13)、
PGCNKRYFKLSHLQMHSRKHTG (配列番号:14)、
CNKRYFKLSHLQMHSRK (配列番号:15)、
CNKRYFKLSHLQMHSRKH (配列番号:16)、
CNKRYFKLSHLQMHSRKHTG (配列番号:17)、
WAPVLDFAPPGASAYGSL (配列番号:18)、
CWAPVLDFAPPGASAYGSL (配列番号:19)、
WAPVLDFAPPGASAYGSLC (配列番号:20)、
SGQARMFPNAPYLPSC (配列番号:34)、
SGQAYMFPNAPYLPSC (配列番号:35)、
SGQARMFPNAPYLPSCLES (配列番号:36)、
SGQAYMFPNAPYLPSCLES (配列番号:37)、
PGCNKRYFKLSHLQMHSRK (配列番号:38)、
PGCNKRYFKLSHLQMHSRKH (配列番号:39)、および
PGCNKRYFKLSHLQMHSRKHTG (配列番号:40)、
から選択されるいずれかのアミノ酸配列を含むペプチド、または配列番号:11~20および34~40から選択されるいずれかのアミノ酸配列中にアミノ酸残基の改変を含有する改変アミノ酸配列を含み且つヘルパーT細胞誘導活性を有するペプチドである、項11に記載の凍結乾燥製剤。
CNKRYFKLSHLQMHSRK (配列番号:15)、
CNKRYFKLSHLQMHSRKH (配列番号:16)、
CNKRYFKLSHLQMHSRKHTG (配列番号:17)、
WAPVLDFAPPGASAYGSL (配列番号:18)、
CWAPVLDFAPPGASAYGSL (配列番号:19)および
WAPVLDFAPPGASAYGSLC (配列番号:20)
から選択されるいずれかのアミノ酸配列からなるペプチドである、項12に記載の凍結乾燥製剤。
ヘルパーペプチドとして、
WAPVLDFAPPGASAYGSL (配列番号:18)、
を含み、さらに
ヒドロキシプロピル-β-シクロデキストリン(HP-β-CD)を含む、項4~7のいずれか一項に記載の凍結乾燥製剤。
ヘルパーペプチドとして、
WAPVLDFAPPGASAYGSL (配列番号:18)、
を含み、さらに
ヒドロキシプロピル-β-シクロデキストリン(HP-β-CD)を含む、項4~7のいずれか一項に記載の凍結乾燥製剤。
さらに、適量のメチオニン等を添加して凍結乾燥させることで、ヘルパーペプチドに由来する類縁物質の発生、増加を抑えることができる。
AlaまたはA:アラニン残基
ArgまたはR:アルギニン残基
AsnまたはN:アスパラギン残基
AspまたはD:アスパラギン酸残基
CysまたはC:システイン残基
GlnまたはQ:グルタミン残基
GluまたはE:グルタミン酸残基
GlyまたはG:グリシン残基
HisまたはH:ヒスチジン残基
IleまたはI:イソロイシン残基
LeuまたはL:ロイシン残基
LysまたはK:リジン残基
MetまたはM:メチオニン残基
PheまたはF:フェニルアラニン残基
ProまたはP:プロリン残基
SerまたはS:セリン残基
ThrまたはT:スレオニン残基
TrpまたはW:トリプトファン残基
TyrまたはY:チロシン残基
ValまたはV:バリン残基
Abu:2-アミノ酪酸残基(α-アミノ酪酸残基とも言う)
Orn:オルニチン残基
Cit:シトルリン残基
RMFPNAPYL (配列番号:2)、
CMTWNQMNL (配列番号:3)、
CYTWNQMNL (配列番号:4)、
ALLPAVPSL (配列番号:5)、
SLGEQQYSV (配列番号:6)、
RVPGVAPTL (配列番号:7)および
VLDFAPPGA (配列番号:8)
から選択されるいずれかのアミノ酸配列を含むペプチド、並びに配列番号:2~8から選択されるいずれかのアミノ酸配列中にアミノ酸残基の改変を含有する改変アミノ酸配列を含み且つCTL誘導活性を有するペプチドが挙げられる。好ましくは、配列番号:2~8から選択されるいずれかのアミノ酸配列からなるペプチド、および配列番号:2~8から選択されるいずれかのアミノ酸配列中にアミノ酸残基の改変を含有する改変アミノ酸配列からなり且つCTL誘導活性を有するペプチドが挙げられる。より好ましくは、配列番号:2~8から選択されるいずれかのアミノ酸配列からなるペプチドが挙げられる。さらにより好ましくは、配列番号:2~6および8から選択されるいずれかのアミノ酸配列からなるペプチドが挙げられる。
C-CMTWNQMNL (配列番号:9)(式中、CとCの間の結合はジスルフィド結合を表す。)または
C-CYTWNQMNL (配列番号:10)(式中、CとCの間の結合はジスルフィド結合を表す。)
のアミノ酸配列を含むペプチド、並びに配列番号:9または10のアミノ酸配列中にアミノ酸残基の改変を含有する改変アミノ酸配列を含み且つCTL誘導活性を有するペプチドが挙げられる。好ましくは、配列番号:9または10のアミノ酸配列からなるペプチド、および配列番号:9または10のアミノ酸配列中にアミノ酸残基の改変を含有する改変アミノ酸配列からなり且つCTL誘導活性を有するペプチドが挙げられる。より好ましくは、配列番号:9または10のアミノ酸配列からなるペプチドが挙げられる。さらにより好ましくは、配列番号:10のアミノ酸配列からなるペプチドが挙げられる。
RMFPNAPYL (配列番号:2)の改変キラーペプチドである、
RYFPNAPYL (配列番号:21)(国際公開第03/106682号参照)、
FMFPNAPYL (配列番号:22)、
RLFPNAPYL (配列番号:23)、
RMMPNAPYL (配列番号:24)、
RMFPNAPYV (配列番号:25)および
YMFPNAPYL (配列番号:26)(国際公開第2009/072610号参照);
CMTWNQMNL (配列番号:3)の改変キラーペプチドである、
CYTWNQMNL (配列番号:4)(国際公開第02/79253号参照)、
Xaa-Met-Thr-Trp-Asn-Gln-Met-Asn-Leu (配列番号:27)、
(本配列中XaaはSerまたはAlaを表す)および
Xaa-Tyr-Thr-Trp-Asn-Gln-Met-Asn-Leu (配列番号:28)
(本配列中XaaはSer、Ala、Abu、Arg、Lys、Orn、Cit、Leu、PheまたはAsnを表す)(国際公開2004/026897号参照);
ALLPAVPSL (配列番号:5)の改変キラーペプチドである、
AYLPAVPSL (配列番号:29)(国際公開第2003/106682号参照);
SLGEQQYSV (配列番号:6)の改変キラーペプチドである、
FLGEQQYSV (配列番号:30)、
SMGEQQYSV (配列番号:31)および
SLMEQQYSV (配列番号:32)(国際公開第2009/072610号参照);並びに
RVPGVAPTL (配列番号:7)の改変キラーペプチドである、
RYPGVAPTL (配列番号:33)(国際公開第2003/106682号参照)。
式(1):
癌抗原ペプチドAは、以下のアミノ酸配列:
RMFPNAPYL (配列番号:2)、
ALLPAVPSL (配列番号:5)、
SLGEQQYSV (配列番号:6)および
RVPGVAPTL (配列番号:7)
の中から選ばれるいずれかのアミノ酸配列からなるペプチドを表し、癌抗原ペプチドAのN末端アミノ酸のアミノ基が式(1)中のYaと結合し、癌抗原ペプチドAのC末端アミノ酸のカルボニル基が式(1)中の水酸基と結合し、
R1は、癌抗原ペプチドCを表し、
癌抗原ペプチドCは、癌抗原ペプチドAとは配列が異なり且つ以下のアミノ酸配列:
CMTWNQMNL (配列番号:3)および
CYTWNQMNL (配列番号:4)
の中から選ばれるいずれかのアミノ酸配列からなるペプチドを表し、癌抗原ペプチドCのシステイン残基のチオエーテル基が式(1)中のチオエーテル基と結合する。]
で表される化合物もしくはその薬学上許容される塩、並びに式(1)の化合物中にアミノ酸残基の改変を含有する改変化合物からなり且つCTL誘導活性を有する化合物である。
かかる改変キラーペプチドとして、これに限定されないが、例えば、以下の化合物:
式(2):
で表される化合物、または
式(3):
式(4):
で表される化合物、並びに式(1)~(4)から選択されるいずれかの化合物中にアミノ酸残基の改変を含有する改変化合物からなり且つCTL誘導活性を有する化合物が挙げられる。好ましくは、式(2)~(4)から選択されるいずれかの化合物が挙げられる。より好ましくは、式(3)または(4)から選択されるいずれかの化合物が挙げられる。さらにより好ましくは、式(3)で表される化合物が挙げられる。
KRYFKLSHLQMHSRKH (配列番号:11)、
SGQARMFPNAPYLPSCLES (配列番号:12)、
RSDELVRHHNMHQRNMTKL (配列番号:13)、
PGCNKRYFKLSHLQMHSRKHTG (配列番号:14)、
CNKRYFKLSHLQMHSRK (配列番号:15)、
CNKRYFKLSHLQMHSRKH (配列番号:16)、
CNKRYFKLSHLQMHSRKHTG (配列番号:17)、
WAPVLDFAPPGASAYGSL (配列番号:18)、
CWAPVLDFAPPGASAYGSL (配列番号:19)、
WAPVLDFAPPGASAYGSLC (配列番号:20)、
SGQARMFPNAPYLPSC (配列番号:34)、
SGQAYMFPNAPYLPSC (配列番号:35)、
SGQARMFPNAPYLPSCLES (配列番号:36)、
SGQAYMFPNAPYLPSCLES (配列番号:37)、
PGCNKRYFKLSHLQMHSRK (配列番号:38)、
PGCNKRYFKLSHLQMHSRKH (配列番号:39)、および
PGCNKRYFKLSHLQMHSRKHTG (配列番号:40)、
から選択されるいずれかのアミノ酸配列を含むペプチド、および配列番号:11~20および34~40から選択されるいずれかのアミノ酸配列中にアミノ酸残基の改変を含有する改変アミノ酸配列を含み且つヘルパーT細胞誘導活性を有するペプチドが挙げられる。好ましくは、配列番号:11~20および34~40から選択されるいずれかのアミノ酸配列からなるペプチド、および配列番号:11~20および34~40から選択されるいずれかのアミノ酸配列中にアミノ酸残基の改変を含有する改変アミノ酸配列からなり且つヘルパーT細胞誘導活性を有するペプチドが挙げられる。より好ましくは、配列番号:11~20および34~40から選択されるいずれかのアミノ酸配列からなるペプチドであり、さらにより好ましくは、配列番号:11~20から選択されるいずれかのアミノ酸配列からなるペプチドが挙げられる。
SGQARMFPNAPYLPSCLES (配列番号:36)の改変ヘルパーペプチドである、
SGQAYMFPNAPYLPSCLES (配列番号:37)(国際公開第2007/120673号参照)、
SGQARMFPNAPYLPSC (配列番号:34)および
SGQAYMFPNAPYLPSC (配列番号:35);並びに
PGCNKRYFKLSHLQMHSRKHTG (配列番号:40)の改変ヘルパーペプチドである、
PGCNKRYFKLSHLQMHSRK (配列番号:38)、
PGCNKRYFKLSHLQMHSRKH (配列番号:39)、
KRYFKLSHLQMHSRKH (配列番号:11)、
CNKRYFKLSHLQMHSRK (配列番号:15)、
CNKRYFKLSHLQMHSRKH (配列番号:16)、
CNKRYFKLSHLQMHSRKHTG (配列番号:17)、
CWAPVLDFAPPGASAYGSL (配列番号:19)および
WAPVLDFAPPGASAYGSLC (配列番号:20)。
このような本発明の化合物を有効成分する製剤をWT1陽性の患者に投与することにより、癌を治療または予防するための方法を提供することができる。
(1)凍結乾燥製剤の調製
下記の処方表の添加量(濃度)となるようにペプチドおよび各製剤成分を注射用水に溶解させ、pH調節剤(1mol/L塩酸)でpHを2~3に調整した。上記で調製した溶液を0.2μmの滅菌フィルターに通してろ過した後、ガラスバイアルに所定量(2~2.4mL)を充填し、凍結乾燥機を用いて凍結乾燥を行った。凍結乾燥工程は、-40℃付近で溶液を凍結させた後、庫内を真空に減圧すると同時に庫内を-20℃付近まで上昇させ、そのまま20時間程度乾燥を行った後、さらに庫内の温度を30℃付近に上昇させ、そのまま12時間程度乾燥させる条件により行った。
キラーペプチドを含有する製剤またはヘルパーペプチドを含有する製剤のいずれであっても、シクロデキストリンを添加しない場合の再溶解時間は3分未満と比較的良好であった。
一方、キラーペプチドおよびヘルパーペプチドを混合した製剤では、シクロデキストリンを添加しない場合の再溶解時間は10分以上になることが示された(下記実施例1を参照)。
これらの結果から、実施例1のようにキラーペプチドおよびヘルパーペプチドを混合した製剤が再溶解するまでに時間を要する原因は、キラーペプチドまたはヘルパーペプチドの溶解度が小さいことにあるわけではなく、キラーペプチドおよびヘルパーペプチドが相互に凝集してしまうことにあると推測される。
(1)凍結乾燥製剤の調製
下記の各処方表(a)~(g)の添加量(濃度)となるように各ペプチドおよび各製剤成分を注射用水に溶解させ、pH調節剤(1mol/L塩酸)でpHを2~3に調整した。上記で調製した溶液を0.2μmの滅菌フィルターに通してろ過した後、ガラスバイアルに所定量(1.2~4mL)を充填し、凍結乾燥機を用いて凍結乾燥を行った。凍結乾燥工程は、-40℃付近で溶液を凍結させた後、庫内を真空に減圧すると同時に庫内を-20℃付近まで上昇させ、そのまま20時間程度乾燥を行った後、さらに庫内の温度を30℃付近に上昇させ、そのまま12時間程度乾燥させる条件により行った。
各凍結乾燥製剤に所定量の注射用水(1mLまたは0.6mL)を加え、復水した時の溶解時間を測定した。
コハク酸を含まない製剤では、再溶解時間を10分以上要したのに対し、コハク酸を含有することで再溶解時間が大幅に短縮した。コハク酸を含有する凍結乾燥製剤のうち、HP-β-シクロデキストリンまたはγシクロデキストリンを有するものでは、さらに再溶解時間を短縮した。
したがって、これらの結果から、実施例に記載するキラーペプチドおよびヘルパーペプチドに対しては、コハク酸の添加およびシクロデキストリンとしてHP-β-シクロデキストリンまたはγ-シクロデキストリンの添加が、再溶解時間の短縮に有効であることが示唆された。
コハク酸およびHP-β-シクロデキストリンを含有する凍結乾燥製剤のうち、D-マンニトール、トレハロースまたはL-メチオニンの含有量の変化に対しては再溶解時間に顕著な差は認められなかった。
したがって、これらの結果より、上記コハク酸およびHP-β-シクロデキストリンを含む製剤では、D-マンニトール、トレハロースまたはL-メチオニンの含有量は再溶解時間に影響しないことが示唆された。
HP-β-シクロデキストリン含有量による相違では、含有濃度2.5m/Lに比べ、6.25m/Lで再溶解時間の大幅な短縮が確認された。7.5m/L以上では再溶解時間の顕著な短縮が確認されたが、一方で再溶解時の激しい泡立ちが確認された。また、酒石酸の有無による再溶解性への影響は認められなかった。
したがって、これらの結果より、HP-β-シクロデキストリン含有量の多い方が再溶解時間の短縮に有効であることが示唆された。一方で、一定以上の濃度では再溶解時の泡立ちのため、製剤の調製工程の観点からは好ましくないことが示唆された。また、HP-β-シクロデキストリン含有製剤では、コハク酸の添加が再溶解時間の短縮に有効であることが示唆された。
高濃度調製された凍結乾燥製剤では、コハク酸濃度による再溶解時間の差は認められなかった。また、実施例5または8と比較し、高濃度製剤(実施例22~25)では再溶解時間の短縮が確認された。一方、コハク酸または酒石酸処方におけるHP-β-シクロデキストリン濃度による変化では、HP-β-シクロデキストリン高濃度処方(実施例26または28)において再溶解時間の短縮が確認されたが、同時に再溶解時の泡立ちが確認された。
したがって、これらの結果より、高濃度製剤では再溶解時間はコハク酸濃度に依存しないこと、およびHP-β-シクロデキストリン高濃度処方では泡立ちのため製剤の調製工程の観点からは好ましくないことが示唆された。
高濃度調製された凍結乾燥製剤では、HP-β-シクロデキストリン濃度によって、再溶解時間の明らかな差が確認された。一方、HP-β-シクロデキストリン濃度20m/L(実施例29)の場合には、再溶解時の泡立ちが確認された。
高濃度調製された凍結乾燥製剤では、D-マンニトールまたはトレハロース濃度による再溶解時間の差は見られなかった。
したがって、これらの結果より、再溶解時間はHP-β-シクロデキストリン濃度に依存するが、HP-β-シクロデキストリン高濃度処方では泡立ちのため製剤の調製工程の観点からは好ましくないことが示唆された。
高濃度調製された凍結乾燥製剤では、メチオニン低濃度またはメチオニンなしの場合に再溶解時間の短縮が見られた。一方、HP-β-シクロデキストリンが20m/Lの場合(実施例44)には、再溶解時の泡立ちが見られた。
したがって、これらの結果より、再溶解時間とメチオニン濃度には負の相関があり、再溶解時間の短縮にはメチオニン濃度の低減が有効であることが示唆された。
D-マンニトール、トレハロースまたはL-メチオニン等の賦形剤の比率による再溶解時間の影響はなかった。一方、L-メチオニンの非添加または低濃度での添加(1.25m/L)では、再溶解時間に差は見られなかった。
したがって、これらの結果より、再溶解時間は、D-マンニトールの濃度、およびトレハロースまたはL-メチオニンの有無には影響しないことが示唆された。
上記の各処方表(a)~(g)の添加量(濃度)となるように、キラーペプチドおよびヘルパーペプチドの代わりに、1種または複数種の配列番号2~10、21~33のペプチドもしくは式(2)、(4)の化合物、または/および配列番号11~20、34~40のペプチド、および各製剤成分を注射用水に溶解させ、pH調節剤(1mol/L塩酸)でpHを2~3に調整する。上記で調製した溶液を0.2μmの滅菌フィルターに通してろ過した後、ガラスバイアルに所定量(1.2~4mL)を充填し、凍結乾燥機を用いて凍結乾燥を行う。凍結乾燥工程は、-40℃付近で溶液を凍結させた後、庫内を真空に減圧すると同時に庫内を-20℃付近まで上昇させ、そのまま20時間程度乾燥を行った後、さらに庫内の温度を30℃付近に上昇させ、そのまま12時間程度乾燥させる条件により行う。
上記実施例から、(a)実施例に記載するペプチドに対しては、コハク酸の添加およびHP-β-シクロデキストリンまたはγ-シクロデキストリンの添加が、再溶解時間の短縮に有効であることが分かる。(b)コハク酸およびHP-β-シクロデキストリンを含む製剤では、D-マンニトール、トレハロースまたはL-メチオニンの含有量は再溶解時間に影響しないことが分かる。(c)HP-β-シクロデキストリン含有量の多い方が再溶解時間の短縮に有効であることが示唆される一方で、一定以上の濃度では再溶解時の泡立ちのため、製剤の調製工程の観点からは好ましくないことが分かる。また、HP-β-シクロデキストリン含有製剤では、コハク酸の添加が再溶解時間の短縮に有効であることが分かる。(d)高濃度製剤では再溶解時間はコハク酸濃度に依存しないこと、およびHP-β-シクロデキストリン高濃度処方では泡立ちのため製剤の調製工程の観点からは好ましくないことが分かる。(e)再溶解時間はHP-β-シクロデキストリン濃度に依存するが、HP-β-シクロデキストリン高濃度処方では泡立ちのため製剤の調製工程の観点からは好ましくないことが分かる。(f)再溶解時間とメチオニン濃度には負の相関があり、再溶解時間の短縮にはメチオニン濃度の低減が有効であることが分かる。(g)コハク酸およびHP-β-シクロデキストリンを含む製剤では、D-マンニトール、トレハロースまたはL-メチオニンの含有量は再溶解時間に影響しないことが分かる。
以上より、1種または複数種の配列番号2~10、21~33のペプチドもしくは式(2)、(4)の化合物、または/および配列番号11~20、34~40のペプチドとシクロデキストリンを含む製剤についても、同様に溶解時間の短縮が見られる。また、当該製剤についても同様に、コハク酸等の有機酸、D-マンニトール、トレハロースまたはL-メチオニン等の添加剤等を適宜含めることができる。
以下の各処方について、製造工程中の不溶物抑制効果を確認した。
処方表の添加量(濃度)となるように、各ペプチドおよび各製剤成分を注射用水に溶解させ、pH調節剤(1mol/L塩酸)でpHを2~3に調整した。上記の溶液を室温下で一晩(14~16時間)攪拌し、性状を確認した。
上記処方表を基に調製した液剤を一晩(14または16時間)静置し、溶液中の不溶物の有無を確認した。また、実施例57および59については、23時間後の溶液中の不溶物の有無を確認した。
実施例46~53において、HP-β-シクロデキストリン高濃度処方では不溶物の生成を抑制することができなかったが、実施例47のメチオニンの非添加により不溶物の生成を抑制することができた。
その他凝集抑制剤、溶解補助剤の添加によっても不溶物の生成を抑制することができなかったが、バルク濃度を1/2濃度とすることで不溶物の生成を抑制することができた。
したがって、これらの結果より、メチオニンの非添加またはバルク濃度の低減が、不溶物の生成抑制に効果的であることが示唆された。
その他、いずれも調製直後は澄明であったが、実施例54、55、56、60では14時間後に微粒子の発生および/または凝集物が確認された。PEG4000の添加では、23時間後において、微粒子の発生および凝集物が確認された。一方、バルク濃度を1/2濃度とした実施例57では23時間後の澄明な性状を維持していた。
したがって、これらの結果より、メチオニン非添加または低濃度の条件において、製造工程中の不溶物の生成が抑制されることが示唆された。また、バルク濃度が低濃度の場合には、さらに長時間の不溶物生成を抑制することが示唆された。
上記の各処方の添加量(濃度)となるように、キラーペプチドおよびヘルパーペプチドの代わりに、1種または複数種の配列番号2~10、21~33のペプチドもしくは式(2)、(4)の化合物、または/および配列番号11~20、34~40のペプチド、および各製剤成分を注射用水に溶解させ、pH調節剤(1mol/L塩酸)でpHを2~3に調整する。上記の溶液を室温下で一晩(14~16時間)攪拌し、性状を確認する。
上記実施例から、これらの結果より、メチオニンの非添加またはバルク濃度の低減が、不溶物の生成抑制に効果的であることが分かる。また、メチオニン非添加または低濃度の条件において、製造工程中の不溶物の生成が抑制されることが分かる。また、バルク濃度が低濃度の場合には、さらに長時間の不溶物生成を抑制することが分かる。
以上より、1種または複数種の配列番号2~10、21~33のペプチドもしくは式(2)、(4)の化合物、または/および配列番号11~20、34~40のペプチドとシクロデキストリンを含む製剤についても、同様に不溶物の抑制効果が見られる。また、当該製剤についても同様に、バルク濃度が一定の場合において長時間の不溶物生成を抑制することができる。
処方表の添加量(濃度)となるように各ペプチドおよび各製剤成分を注射用水に溶解させ、pH調節剤(1mol/L塩酸)でpHを2~3に調整した。上記で調整した溶液を0.2μmの滅菌フィルターに通してろ過した後、ガラスバイアルに所定量(4mL)を充填し、凍結乾燥機を用いて凍結乾燥を行った。凍結乾燥工程は、-40℃付近で溶液を凍結させた後、庫内を真空に減圧すると同時に庫内を-20℃付近まで上昇させ、そのまま20時間程度乾燥を行った後、さらに庫内の温度を30℃付近に上昇させ、そのまま12時間程度乾燥させる条件により行った。
以下、5℃、25℃または40℃の条件下、調製時、2週間保存後及び1ヶ月保存後の各凍結乾燥製剤を所定量の注射用水(1mL又は1.2mL)を加えて溶解し、類縁物質(RRT.0.875)の含有量を評価した。類縁物質(RRT.0.875)の含有量は、C18逆相カラム(2.1mm×100mm,1.7μm)を用い、純水、アセトニトリル、トリフルオロ酢酸を移動相に用いた。逆相高速クロマトグラフィー法(検出波長:220nm)により測定した。以下の式により類縁物質(RRT.0875)の含有量を算出した。
メチオニン非添加の処方に比べ、メチオニン低濃度(1.25mg/mLまたは2.5mg/mL)の処方では、長時間保管における類縁物質の発生を抑制した。
したがって、これらの結果より、メチオニンの添加が長時間における類縁物質の発生抑制に寄与することが示唆された。
上記処方表の添加量(濃度)となるように、キラーペプチドおよびヘルパーペプチドの代わりに、1種または複数種の配列番号2~10、21~33のペプチドもしくは式(2)、(4)の化合物、または/および配列番号11~20、34~40のペプチド、および各製剤成分を注射用水に溶解させ、pH調節剤(1mol/L塩酸)でpHを2~3に調整する。上記で調整した溶液を0.2μmの滅菌フィルターに通してろ過した後、ガラスバイアルに所定量(4mL)を充填し、凍結乾燥機を用いて凍結乾燥を行う。凍結乾燥工程は、-40℃付近で溶液を凍結させた後、庫内を真空に減圧すると同時に庫内を-20℃付近まで上昇させ、そのまま20時間程度乾燥を行った後、さらに庫内の温度を30℃付近に上昇させ、そのまま12時間程度乾燥させる条件により行う。
上記実施例から、これらの結果より、メチオニンの添加が長時間における類縁物質の発生抑制に寄与することがわかる。
以上より、1種または複数種の配列番号2~10、21~33のペプチドもしくは式(2)、(4)の化合物、または/および配列番号11~20、34~40のペプチドとシクロデキストリンを含む製剤についても、同様に類縁物質の発生を抑制することができる。
Claims (20)
- WT1キラーペプチド、WT1ヘルパーペプチドおよびシクロデキストリンを含む凍結乾燥製剤であって、キラーペプチドとして、
ヘルパーペプチドとして、
WAPVLDFAPPGASAYGSL (配列番号:18)
を含み、
シクロデキストリンが、α-シクロデキストリン(α-CD)、γ-シクロデキストリン(γ-CD)、ヒドロキシプロピル-β-シクロデキストリン(HP-β-CD)、およびこれらの薬学上許容される塩からなる群から選択される1または2以上であり、
キラーペプチド1重量部に対し、ヘルパーペプチドが0.1~2.0重量部であり、シクロデキストリンが0.2~5.0重量部であり、
さらにpH調整剤を含有し、pHが2~3である、凍結乾燥製剤。 - キラーペプチド1重量部に対し、ヘルパーペプチドが0.5~1.0重量部であり、シクロデキストリンが0.5~2.0重量部である、請求項1または2に記載の凍結乾燥製剤。
- キラーペプチド1重量部に対し、ヘルパーペプチドが0.75重量部であり、シクロデキストリンが1.0重量部である、請求項1~3のいずれか一項に記載の凍結乾燥製剤。
- シクロデキストリンが、ヒドロキシプロピル-β-シクロデキストリン(HP-β-CD)、またはその薬学上許容される塩である、請求項1~4のいずれか一項に記載の凍結乾燥製剤。
- さらにアルギニンまたはメチオニンを含む、請求項1~5のいずれか一項に記載の凍結乾燥製剤。
- アルギニンまたはメチオニンの量が、ヘルパーペプチド1重量部に対し0.01~1.0重量部である、請求項6に記載の凍結乾燥製剤。
- アルギニンまたはメチオニンの量が、ヘルパーペプチド1重量部に対し0.1~0.5重量部である、請求項6または7に記載の凍結乾燥製剤。
- メチオニンとして、L-メチオニンを含む、請求項6~8のいずれか一項に記載の凍結乾燥製剤。
- さらに有機酸を含有する、請求項1~9のいずれか一項に記載の凍結乾燥製剤。
- 有機酸の量が、ヘルパーペプチド1重量部に対し0.01~1.0重量部である、請求項10に記載の凍結乾燥製剤。
- 有機酸の量が、ヘルパーペプチド1重量部に対し0.05~0.5重量部である、請求項10または11に記載の凍結乾燥製剤。
- 有機酸が酒石酸および/またはコハク酸である、請求項10~12のいずれか一項に記載の凍結乾燥製剤。
- さらにアジュバントを含有する、請求項1~13のいずれか一項に記載の凍結乾燥製剤。
- アジュバンドの量が、キラーペプチド1重量部に対し1~500重量部である、請求項14に記載の凍結乾燥製剤。
- アジュバンドの量が、キラーペプチド1重量部に対し5~100重量部である、請求項14または15に記載の凍結乾燥製剤。
- アジュバンドが、フロイントアジュバント、モンタナイドおよびW/Oエマルションの中から選ばれるいずれか一つである、請求項14~16のいずれか一項に記載の凍結乾燥製剤。
- アジュバントがモンタナイドである、請求項14~17のいずれか一項に記載の凍結乾燥製剤。
- pH調整剤の量が、キラーペプチド1重量部に対し0.001~1000重量部である、請求項1~18のいずれか一項に記載の凍結乾燥製剤。
- pH調整剤が塩酸である、請求項1~19のいずれか一項に記載の凍結乾燥製剤。
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