JPWO2019073379A5 - - Google Patents
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- JPWO2019073379A5 JPWO2019073379A5 JP2020540865A JP2020540865A JPWO2019073379A5 JP WO2019073379 A5 JPWO2019073379 A5 JP WO2019073379A5 JP 2020540865 A JP2020540865 A JP 2020540865A JP 2020540865 A JP2020540865 A JP 2020540865A JP WO2019073379 A5 JPWO2019073379 A5 JP WO2019073379A5
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- pharmaceutical composition
- crystalline psilocybin
- less
- psilocybin
- determined
- Prior art date
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- QKTAAWLCLHMUTJ-UHFFFAOYSA-N Psilocybin Chemical compound C1C=CC(OP(O)(O)=O)=C2C(CCN(C)C)=CN=C21 QKTAAWLCLHMUTJ-UHFFFAOYSA-N 0.000 claims description 83
- 239000008194 pharmaceutical composition Substances 0.000 claims description 56
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 20
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 19
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 19
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 19
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 19
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 11
- 239000002245 particle Substances 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 229940079593 drugs Drugs 0.000 claims description 5
- 239000012535 impurity Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229920002472 Starch Polymers 0.000 claims description 4
- 229940032147 Starch Drugs 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical group [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 4
- 239000000546 pharmaceutic aid Substances 0.000 claims description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 4
- 239000008107 starch Substances 0.000 claims description 4
- 235000019698 starch Nutrition 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- 239000007884 disintegrant Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 239000000314 lubricant Substances 0.000 claims description 3
- 229960003563 Calcium Carbonate Drugs 0.000 claims description 2
- 229960001681 Croscarmellose Sodium Drugs 0.000 claims description 2
- 229920002785 Croscarmellose sodium Polymers 0.000 claims description 2
- FBPFZTCFMRRESA-KAZBKCHUSA-N D-Mannitol Natural products OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KAZBKCHUSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinylpyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- 229940069328 Povidone Drugs 0.000 claims description 2
- 229940033134 Talc Drugs 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 claims description 2
- 229940075614 colloidal silicon dioxide Drugs 0.000 claims description 2
- 229920001531 copovidone Polymers 0.000 claims description 2
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 claims description 2
- 235000019700 dicalcium phosphate Nutrition 0.000 claims description 2
- 235000019359 magnesium stearate Nutrition 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
- 229960001855 mannitol Drugs 0.000 claims description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 235000012239 silicon dioxide Nutrition 0.000 claims description 2
- 229960001866 silicon dioxide Drugs 0.000 claims description 2
- 229940079832 sodium starch glycolate Drugs 0.000 claims description 2
- 239000008109 sodium starch glycolate Substances 0.000 claims description 2
- 229920003109 sodium starch glycolate Polymers 0.000 claims description 2
- 229940045902 sodium stearyl fumarate Drugs 0.000 claims description 2
- STFSJTPVIIDAQX-LTRPLHCISA-M sodium;(E)-4-octadecoxy-4-oxobut-2-enoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOC(=O)\C=C\C([O-])=O STFSJTPVIIDAQX-LTRPLHCISA-M 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 235000012222 talc Nutrition 0.000 claims description 2
- 238000001757 thermogravimetry curve Methods 0.000 claims description 2
- 230000000996 additive Effects 0.000 claims 3
- 206010018075 Generalised anxiety disease Diseases 0.000 claims 2
- 206010034721 Personality disease Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 201000006529 generalized anxiety disease Diseases 0.000 claims 2
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 claims 2
- 201000003895 major depressive disease Diseases 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- 201000008430 obsessive-compulsive disease Diseases 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
- 208000007848 Alcoholism Diseases 0.000 claims 1
- 208000006561 Cluster Headache Diseases 0.000 claims 1
- 206010013663 Drug dependence Diseases 0.000 claims 1
- 206010057852 Nicotine dependence Diseases 0.000 claims 1
- 208000001908 Opioid-Related Disorders Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 206010034158 Pathological gambling Diseases 0.000 claims 1
- ZBWSBXGHYDWMAK-UHFFFAOYSA-N Psilocin Chemical compound C1=CC=C(O)[C]2C(CCN(C)C)=CN=C21 ZBWSBXGHYDWMAK-UHFFFAOYSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 201000007930 alcohol dependence Diseases 0.000 claims 1
- AMUOHENPQIBKPS-UHFFFAOYSA-N benzyl [3-[2-[benzyl(dimethyl)azaniumyl]ethyl]-1H-indol-4-yl] phosphate Chemical compound C=1C=CC=CC=1C[N+](C)(C)CCC(C=12)=CNC2=CC=CC=1OP([O-])(=O)OCC1=CC=CC=C1 AMUOHENPQIBKPS-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 238000004166 bioassay Methods 0.000 claims 1
- 201000008176 body dysmorphic disease Diseases 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 201000006145 cocaine dependence Diseases 0.000 claims 1
- 201000009929 conduct disease Diseases 0.000 claims 1
- NSBNXCZCLRBQTA-UHFFFAOYSA-N dibenzyl bis(phenylmethoxy)phosphoryl phosphate Chemical compound C=1C=CC=CC=1COP(OP(=O)(OCC=1C=CC=CC=1)OCC=1C=CC=CC=1)(=O)OCC1=CC=CC=C1 NSBNXCZCLRBQTA-UHFFFAOYSA-N 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 201000006180 eating disease Diseases 0.000 claims 1
- 238000000921 elemental analysis Methods 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000004067 bulking agent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000005712 crystallization Effects 0.000 description 2
- 238000011031 large scale production Methods 0.000 description 2
- 208000009025 Nervous System Disease Diseases 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- -1 hydroxylpropyl Chemical group 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Description
本発明の第三の態様にしたがい、結晶性シロシビンと１又はそれを超える添加剤とを含む薬学的調合物が提供される。 According to a third aspect of the invention there is provided a pharmaceutical formulation comprising crystalline psilocybin and one or more excipients .
一実施形態において、高純度シロシビン及び１又はそれを超える添加剤を含む薬学的調合物が提供される。別の実施形態において、結晶性シロシビン多形Ａと１又はそれを超える添加剤とを含む薬学的調合物が提供される。別の実施形態において、結晶性シロシビン多形Ａ’と１又はそれを超える添加剤とを含む薬学的調合物が提供される。別の実施形態において、高純度結晶性シロシビン、多形Ａ又は多形Ａ’と１又はそれを超える添加剤とを含む薬学的調合物が提供される。別の実施形態において、高純度結晶性シロシビン多形Ａと１又はそれを超える添加剤とを含む薬学的調合物が提供される。別の実施形態において、高純度結晶性シロシビン多形Ａ’と１又はそれを超える添加剤とを含む薬学的調合物が提供される。 In one embodiment, pharmaceutical formulations are provided comprising highly purified psilocybin and one or more excipients . In another embodiment, pharmaceutical formulations are provided comprising crystalline psilocybin polymorph A and one or more excipients . In another embodiment, pharmaceutical formulations are provided comprising crystalline psilocybin polymorph A' and one or more excipients . In another embodiment, a pharmaceutical formulation is provided comprising highly pure crystalline psilocybin, polymorph A or polymorph A' and one or more excipients . In another embodiment, pharmaceutical formulations are provided comprising highly pure crystalline psilocybin polymorph A and one or more excipients . In another embodiment, a pharmaceutical formulation is provided comprising highly pure crystalline psilocybin polymorph A' and one or more excipients .
経口調合物用の好ましい薬学的添加剤には、微結晶セルロース、デンプン、マンニトール、リン酸水素カルシウム無水物、又は二酸化ケイ素、炭酸カルシウム、微結晶セルロース及びタルクの共混合物（ｃｏ－ｍｉｘｔｕｒｅｓ）などの希釈剤；デンプングリコール酸ナトリウム又はクロスカルメロースナトリウムなどの崩壊剤；ポビドン、コポビドン又はヒドロキシルプロピルセルロースなどの結合剤；ステアリン酸マグネシウム又はステアリルフマル酸ナトリウムなどの滑沢剤；コロイド状二酸化ケイ素などの流動促進剤；及びＯｐａｄｒｙＩＩホワイト又はＰＶＡをベースとするブラウンＯｐａｄｒｙＩＩなどのフィルムコートが含まれる。 Preferred pharmaceutical excipients for oral formulations include microcrystalline cellulose, starch, mannitol, calcium hydrogen phosphate anhydrous, or co-mixtures of silicon dioxide, calcium carbonate, microcrystalline cellulose and talc. Diluents; disintegrants such as sodium starch glycolate or croscarmellose sodium; binders such as povidone, copovidone or hydroxylpropyl cellulose; lubricants such as magnesium stearate or sodium stearyl fumarate; flow agents such as colloidal silicon dioxide. accelerators; and film coats such as Opadry II white or PVA-based brown Opadry II.
多くの薬学的錠剤に対して、標準的な添加剤、特に増量剤を使用することができる。しかしながら、シロシビン錠剤を調合する際に、出願人は、満足できる製品を達成するためには、標準的でない増量剤が好ましいことを見出した。 Standard excipients , especially bulking agents, can be used for many pharmaceutical tablets. However, in formulating psilocybin tablets, Applicants have found that non-standard bulking agents are preferred in order to achieve a satisfactory product.
シロシビンは、１又はそれを超える添加剤と一緒に存在するであろう。好ましい添加剤には、微結晶セルロース及びデンプン、より好ましくは、珪化された微結晶セルロースが含まれる。 Psilocybin will be present with one or more additives . Preferred additives include microcrystalline cellulose and starch, more preferably silicified microcrystalline cellulose.
その結果、出願人は改変された添加剤、より具体的には、異なる粒径を有する珪化された増量剤に注目した。これらの調合物は、下表４０に記載されている。
混和均一性の一貫性（誤差を考慮して９５％超）と同様に、含量均一性の主要なパラメータ（９０％超、実際には９４％超）及びＡＶ（１０未満、実際には７未満）が優れていることを認めることができる。
本発明は、例えば、以下の項目を提供する。
（項目１）
多形Ａ又は多形Ａ’の形態の結晶性シロシビンであって、
ａ．１１．５、１２．０及び１４．５°２θ±０．１°２θにおけるＸＲＰＤディフラクトグラム中のピーク；
ｂ．１１．５、１２．０及び１４．５°２θ±０．１°２θにおけるＸＲＰＤディフラクトグラム中のピーク［１９．７、２０．４、２２．２、２４．３若しくは２５．７°２θ±０．１°２θにおける少なくとも１つのさらなるピークによってさらに特徴付けられる］；
ｃ．図７ａ若しくは７ｂに実質的に図示されているＸＲＰＤディフラクトグラム；又は
ｄ．図８ａ若しくは図８ｂに実質的に図示されている、２０５～２２０℃の開始温度を有するＤＳＣサーモグラムにおける吸熱事象
の１つ又はそれより多くによって特徴付けられる、多形Ａ又は多形Ａ’の形態の結晶性シロシビン。
（項目２）
２１０～２１５℃の開始温度を有するＤＳＣサーモグラムにおける吸熱事象によってさらに特徴付けられる、項目１に記載の、多形Ａ又は多形Ａ’の形態の結晶性シロシビン。
（項目３）
ａ．１１．５、１２．０、１４．５、及び１７．５°２θ±０．１°２θにおけるＸＲＰＤディフラクトグラム中のピーク；
ｂ．１１．５、１２．０、１４．５及び１７．５°２θ±０．１°２θにおけるＸＲＰＤディフラクトグラム中のピーク［１９．７、２０．４、２２．２、２４．３若しくは２５．７°２θ±０．１°２θにおける少なくとも１つのさらなるピークによってさらに特徴付けられる］；
ｃ．図７ａに実質的に図示されているＸＲＰＤディフラクトグラム；又は
ｄ．図８ａに実質的に図示されている、２０５～２２０℃の開始温度を有するＤＳＣサーモグラムにおける吸熱事象
の１つ又はそれより多くによって特徴付けられる、項目１又は２に記載の、多形Ａの形態の結晶性シロシビン。
（項目４）
１７．５°２θ±０．１°２θにおけるピークが、１４．５°２θ±０．１°２θにおけるピークと比べて、少なくとも５％の相対強度を有する、項目３に記載の、多形Ａの形態の結晶性シロシビン。
（項目５）
ａ．１１．５、１２．０及び１４．５°２θ±０．１°２θにおけるＸＲＰＤディフラクトグラム中のピーク［ただし、１７．５°２θ±０．１°２θにおけるピークが非存在又は実質的に非存在である］；
ｂ．１１．５、１２．０及び１４．５°２θ±０．１°２θにおけるＸＲＰＤディフラクトグラム中のピーク［ただし、１７．５°２θ±０．１°２θにおけるピークが非存在又は実質的に非存在であり、１９．７、２０．４、２２．２、２４．３若しくは２５．７°２θ±０．１°２θにおける少なくとも１つのさらなるピークによってさらに特徴付けられる］；
ｃ．図７ｂに実質的に図示されているＸＲＰＤディフラクトグラム；又は
ｄ．図８ｂに実質的に図示されている、２０５～２２０℃の開始温度を有するＤＳＣサーモグラムにおける吸熱事象
の１つ又はそれより多くによって特徴付けられる、項目１又は２に記載の、多形Ａ’の形態の結晶性シロシビン。
（項目６）
１７．５°２θ±０．１°２θにおけるいずれのピークも、１４．５°２θ±０．１°２θにおけるピークと比べて、５％未満の相対強度を有する、項目５に記載の多形Ａ’の形態の結晶性シロシビン。
（項目７）
ｉｉ）０．５％ｗ／ｗ未満の水含量又は
ｉｉｉ）２５℃などの周囲温度～２００℃でのＴＧＡサーモグラムにおける０．５％ｗ／ｗ未満の損失
のいずれかを有することによってさらに特徴付けられる、項目１から６のいずれかに記載の、多形Ａ又は多形Ａ’の形態の結晶性シロシビン。
（項目８）
ＨＰＬＣによれば９７％より大きい化学的純度を有し、並びに３１Ｐ ＮＭＲによって測定されるリン酸及びＨＰＬＣによって測定されるサイロシンを含めた、１％より大きい単一の不純物を有さない、先行する項目のいずれかに記載の、多形Ａ又は多形Ａ’の形態の結晶性シロシビン。
（項目９）
前記結晶性シロシビンが白色ないし灰白色の固体である、先行する項目のいずれかに記載の多形Ａ又は多形Ａ’の形態の結晶性シロシビン。
（項目１０）
図１０～図１３のいずれか１つ又はそれより多くと合致するスペクトルを含む、先行する項目のいずれかに記載の多形Ａ又は多形Ａ’の形態の結晶性シロシビン。
（項目１１）
表９の点６～１３の、１又はそれを超える品質特性の受容基準を含む、先行する項目のいずれかに記載の多形Ａ又は多形Ａ’の形態の結晶性シロシビン。
（項目１２）
少なくとも１００ｇを含む、項目１～４又は７～１１に記載の結晶性シロシビン多形Ａのバッチ。
（項目１３）
先行する項目のいずれかに記載の多形Ａ又は多形Ａ’の形態の結晶性シロシビンを含む薬学的調合物。
（項目１４）
経口剤形である項目１３に記載の薬学的調合物。
（項目１５）
前記多形Ａ又は多形Ａ’の形態の結晶性シロシビンが０．０１ｍｇ／ｋｇ～１ｍｇ／ｋｇの用量を与える量で存在する、項目１３又は１４に記載の薬学的調合物。
（項目１６）
１又はそれを超える添加剤を含む、項目１３～１５のいずれかに記載の薬学的調合物。
（項目１７）
前記１又はそれを超える添加剤が微結晶セルロース又はデンプンを含む、項目１６に記載の薬学的調合物。
（項目１８）
前記１又はそれを超える添加剤が珪化された微結晶セルロースを含む、項目１６に記載の薬学的調合物。
（項目１９）
医薬において使用するための、項目１～１１に記載の多形Ａ又は多形Ａ’の形態の結晶性シロシビン。
（項目２０）
中枢神経障害を処置することにおいて使用するための、項目１～１１に記載の多形Ａ又は多形Ａ’の形態の結晶性シロシビン。
（項目２１）
薬物抵抗性うつ病を処置することにおいて使用するための、項目１～１１に記載の多形Ａ又は多形Ａ’の形態の結晶性シロシビン。
（項目２２）
多型Ａの形態のシロシビン（１２）の大規模製造のための方法であって、前記方法が、項目１～４又は７～１１のいずれかに記載の結晶性シロシビン多形Ａを生産するために、制御された乾燥とともに、シロシビン（１２）を水結晶化工程に供することを含むことを特徴とする、方法。
（項目２３）
医薬において使用するための、多形Ａ（１２Ａ）の形態の結晶性シロシビン。
（項目２４）
薬物抵抗性うつ病を処置することにおいて使用するための、多形Ａ（１２Ａ）の形態の結晶性シロシビン。
（項目２５）
薬物抵抗性うつ病を処置することを必要とする対象に、有効用量の多形Ａ（１２Ａ）の形態の結晶性シロシビンを投与することを含む、薬物抵抗性うつ病を処置する方法。
（項目２６）
ａ．１１．５、１２．０、１４．５及び１７．５°２θ±０．１°２θにおけるＸＲＰＤディフラクトグラム中のピーク；
ｂ．１１．５、１２．０、１４．５及び１７．５°２θ±０．１°２θにおけるＸＲＰＤディフラクトグラム中のピーク［１９．７、２０．４、２２．２、２４．３若しくは２５．７°２θ±０．１°２θにおける少なくとも１つのさらなるピークによってさらに特徴付けられる］；
ｃ．図７ａに実質的に図示されているＸＲＰＤディフラクトグラム；又は
ｄ．図８ａに実質的に図示されている、２０５～２２０℃の開始温度を有するＤＳＣサーモグラムにおける吸熱事象
の１つ又はそれより多くによって特徴付けられる、結晶を生産するために、制御された乾燥とともに、シロシビン（１２）を水結晶化工程に供することを含むことを特徴とする、多形Ａ（１２Ａ）の形態のシロシビン（１２）の大規模製造のための方法。
（項目２７）
前記シロシビンが、約１０～２０容量の水中で再結晶され、少なくとも７０℃の温度に撹拌しながら加熱され、仕上げろ過され、約７０℃の温度でシードされ、２時間を超える期間にわたって約５℃に冷却される、項目２６に記載の方法。
Key parameters of content uniformity (>90%, actually >94%) and AV (<10, actually <7), as well as blend uniformity consistency (>95% considering error) ) can be recognized as superior.
The present invention provides, for example, the following items.
(Item 1)
crystalline psilocybin in the form of polymorph A or polymorph A',
a. Peaks in the XRPD diffractogram at 11.5, 12.0 and 14.5 degrees 2-theta ± 0.1 degrees 2-theta;
b. Peaks in XRPD diffractograms at 11.5, 12.0 and 14.5 °2θ ± 0.1 °2θ [19.7, 20.4, 22.2, 24.3 or 25.7 °2θ ± further characterized by at least one additional peak at 0.1° 2-theta];
c. an XRPD diffractogram substantially as illustrated in Figure 7a or 7b; or d. of polymorph A or polymorph A′ characterized by one or more endothermic events in a DSC thermogram having an onset temperature of 205-220° C., substantially illustrated in FIG. 8a or 8b. Form of crystalline psilocybin.
(Item 2)
Crystalline psilocybin in the form of polymorph A or polymorph A' according to item 1, further characterized by an endothermic event in the DSC thermogram with an onset temperature of 210-215°C.
(Item 3)
a. peaks in the XRPD diffractogram at 11.5, 12.0, 14.5, and 17.5 degrees 2-theta ± 0.1 degrees 2-theta;
b. Peaks in XRPD diffractograms at 11.5, 12.0, 14.5 and 17.5 °2θ ± 0.1 °2θ [19.7, 20.4, 22.2, 24.3 or 25. further characterized by at least one additional peak at 7° 2-theta ± 0.1° 2-theta];
c. an XRPD diffractogram substantially as illustrated in Figure 7a; or d. Polymorph A, according to items 1 or 2, characterized by one or more endothermic events in a DSC thermogram with an onset temperature of 205-220° C., substantially illustrated in FIG. 8a. Form of crystalline psilocybin.
(Item 4)
Polymorph A, according to item 3, wherein the peak at 17.5° 2-theta ± 0.1° 2-theta has a relative intensity of at least 5% compared to the peak at 14.5° 2-theta ± 0.1° 2-theta crystalline psilocybin in the form of
(Item 5)
a. Peaks in the XRPD diffractogram at 11.5, 12.0 and 14.5 °2θ ± 0.1 °2θ [provided that the peak at 17.5 °2θ ± 0.1 °2θ is absent or substantially is non-existent];
b. Peaks in the XRPD diffractogram at 11.5, 12.0 and 14.5 °2θ ± 0.1 °2θ [provided that the peak at 17.5 °2θ ± 0.1 °2θ is absent or substantially is absent and further characterized by at least one additional peak at 19.7, 20.4, 22.2, 24.3 or 25.7 degrees 2-theta ± 0.1 degrees 2-theta];
c. an XRPD diffractogram substantially as illustrated in Figure 7b; or d. Polymorph A′ according to items 1 or 2, characterized by one or more endothermic events in a DSC thermogram with an onset temperature of 205-220° C., substantially illustrated in FIG. 8b. crystalline psilocybin in the form of
(Item 6)
6. The polymorph of item 5, wherein any peak at 17.5 degrees 2-theta ± 0.1 degrees 2-theta has a relative intensity of less than 5% compared to the peak at 14.5 degrees 2-theta ± 0.1 degrees 2-theta. Crystalline psilocybin in form A'.
(Item 7)
further characterized by having either ii) less than 0.5% w/w water content or iii) less than 0.5% w/w loss in TGA thermogram from ambient temperature such as 25°C to 200°C 7. Crystalline psilocybin in the form of polymorph A or polymorph A' according to any of items 1 to 6, labeled.
(Item 8)
A predecessor having a chemical purity greater than 97% by HPLC and no single impurity greater than 1%, including phosphoric acid as determined by 31 P NMR and thyrosine as determined by HPLC. Crystalline psilocybin in the form of polymorph A or polymorph A' according to any of the preceding items.
(Item 9)
Crystalline psilocybin in the form of polymorph A or polymorph A' according to any of the preceding items, wherein said crystalline psilocybin is a white to off-white solid.
(Item 10)
Crystalline psilocybin in the form of polymorph A or polymorph A' according to any of the preceding items comprising a spectrum matching any one or more of Figures 10-13.
(Item 11)
Crystalline psilocybin in the form of polymorph A or polymorph A' according to any of the preceding items, including acceptance criteria for one or more quality attributes, points 6-13 of Table 9.
(Item 12)
A batch of crystalline psilocybin polymorph A according to items 1-4 or 7-11 comprising at least 100 g.
(Item 13)
A pharmaceutical formulation comprising crystalline psilocybin in the form of polymorph A or polymorph A' according to any of the preceding items.
(Item 14)
14. A pharmaceutical formulation according to item 13, which is an oral dosage form.
(Item 15)
15. Pharmaceutical formulation according to item 13 or 14, wherein said crystalline psilocybin in the form of polymorph A or polymorph A' is present in an amount to give a dose of 0.01 mg/kg to 1 mg/kg.
(Item 16)
16. A pharmaceutical formulation according to any of items 13-15, comprising one or more excipients .
(Item 17)
17. Pharmaceutical formulation according to item 16, wherein said one or more additives comprise microcrystalline cellulose or starch.
(Item 18)
17. The pharmaceutical formulation of item 16, wherein said one or more additives comprise silicified microcrystalline cellulose.
(Item 19)
Crystalline psilocybin in the form of polymorph A or polymorph A' according to items 1 to 11 for use in medicine.
(Item 20)
Crystalline psilocybin in the form of polymorph A or polymorph A' according to items 1-11 for use in treating a central nervous system disorder.
(Item 21)
Crystalline psilocybin in the form of polymorph A or polymorph A' according to items 1-11 for use in treating drug-resistant depression.
(Item 22)
A process for the large-scale production of psilocybin (12) in the form of polymorph A, said process producing crystalline psilocybin polymorph A according to any of items 1-4 or 7-11. 2., subjecting the psilocybin (12) to a water crystallization step with controlled drying.
(Item 23)
Crystalline psilocybin in the form of polymorph A (12A) for use in medicine.
(Item 24)
Crystalline psilocybin in the form of polymorph A (12A) for use in treating drug-resistant depression.
(Item 25)
A method of treating drug-resistant depression comprising administering an effective dose of crystalline psilocybin in the form of polymorph A (12A) to a subject in need thereof.
(Item 26)
a. Peaks in the XRPD diffractogram at 11.5, 12.0, 14.5 and 17.5 degrees 2-theta ± 0.1 degrees 2-theta;
b. Peaks in XRPD diffractograms at 11.5, 12.0, 14.5 and 17.5 °2θ ± 0.1 °2θ [19.7, 20.4, 22.2, 24.3 or 25. further characterized by at least one additional peak at 7° 2-theta ± 0.1° 2-theta];
c. an XRPD diffractogram substantially as illustrated in Figure 7a; or d. with controlled drying to produce crystals characterized by one or more of the endothermic events in the DSC thermogram with an onset temperature of 205-220° C., substantially illustrated in FIG. 8a. , a process for the large-scale production of psilocybin (12) in the form of polymorph A (12A), comprising subjecting psilocybin (12) to a water crystallization process.
(Item 27)
The psilocybin is recrystallized in about 10-20 volumes of water, heated with stirring to a temperature of at least 70° C., polish filtered, seeded at a temperature of about 70° C. and seeded at a temperature of about 5° C. over a period of more than 2 hours. 27. The method of item 26, wherein the method is cooled to
Claims (68)
ａ）２％ｗ／ｗ以下の乾燥時減量； a) loss on drying of 2% w/w or less;
ｂ）０．５％ｗ／ｗ以下の強熱残分； b) residue on ignition not more than 0.5% w/w;
ｃ）ＨＰＬＣにより測定される９５～１０３重量％のアッセイ（乾燥ベース）； c) 95-103 wt% assay (dry basis) as determined by HPLC;
ｄ）ＨＲＧＣにより測定される３０００ｐｐｍメタノール；５０００ｐｐｍエタノール、７２０ｐｐｍＴＨＦ、および８９０ｐｐｍトルエン以下の残存溶媒含量；および d) 3000 ppm methanol as measured by HRGC; residual solvent content not greater than 5000 ppm ethanol, 720 ppm THF, and 890 ppm toluene; and
ｅ）以下の誘導結合プラズマ質量分析（ＩＣＰ－ＭＳ）元素分析： e) Inductively Coupled Plasma Mass Spectrometry (ICP-MS) elemental analysis of:
ｉ． １．５ｐｐｍ以下 Ｃｄ； i. 1.5 ppm or less Cd;
ｉｉ． １．５ｐｐｍ以下 Ｐｂ； ii. 1.5 ppm or less Pb;
ｉｉｉ． ４．５ｐｐｍ以下 Ａｓ； iii. 4.5 ppm or less As;
ｉｖ． ９．０ｐｐｍ以下 Ｈｇ； iv. 9.0 ppm or less Hg;
ｖ． １５ｐｐｍ以下 Ｃｏ； v. 15 ppm or less Co;
ｖｉ． ３０ｐｐｍ以下 Ｖ； vi. 30 ppm or less V;
ｖｉｉ． ６０ｐｐｍ以下 Ｎｉ； vii. 60 ppm or less Ni;
ｖｉｉｉ．１６５ｐｐｍ以下 Ｌｉ；および viii. 165 ppm or less Li; and
ｉｘ． ３０ｐｐｍ以下 Ｐｄ ix. 30ppm or less Pd
のうちの１つ以上によって特徴付けられる、結晶性シロシビン。Crystalline psilocybin, characterized by one or more of
（１） １１．５±０．１、１２．０±０．１、１４．５±０．１、１７．５±０．１および１９．７±０．１°２θにおける粉末Ｘ線回折（ＸＲＰＤ）ピークにより特徴付けられる結晶性シロシビン組成物を提供すること；および (1) Powder X-ray diffraction at 11.5 ± 0.1, 12.0 ± 0.1, 14.5 ± 0.1, 17.5 ± 0.1 and 19.7 ± 0.1 ° 2θ ( providing a crystalline psilocybin composition characterized by an XRPD) peak; and
（２） 少なくとも１つの薬学的に受容可能な添加剤とともに前記組成物を調合すること (2) formulating said composition with at least one pharmaceutically acceptable excipient;
を含んで前記薬学的組成物を与える、方法。and providing said pharmaceutical composition comprising:
（１）サイロシンをテトラベンジルピロホスフェートと反応させて、ベンジル３－［２－（ベンジルジメチルアザニウムイル）エチル］－１Ｈ－インドール－４－イルホスフェートを形成すること； (1) reacting thyrosine with tetrabenzylpyrophosphate to form benzyl 3-[2-(benzyldimethylazaniumyl)ethyl]-1H-indol-4-ylphosphate;
（２）触媒の存在下で、ベンジル３－［２－（ベンジルジメチルアザニウムイル）エチル］－１Ｈ－インドール－４－イルホスフェートを水素と反応させて、少なくとも約１００ｇ以上のシロシビンを形成すること；および (2) reacting benzyl 3-[2-(benzyldimethylazaniumyl)ethyl]-1H-indol-4-yl phosphate with hydrogen in the presence of a catalyst to form at least about 100 g or more of psilocybin; ;and
（３）前記結晶性シロシビンを水から結晶化すること (3) crystallizing the crystalline psilocybin from water;
を含んで前記結晶性シロシビンを提供するプロセスによって調製される、結晶性シロシビン。crystalline psilocybin prepared by a process for providing said crystalline psilocybin comprising:
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