JP6944462B2 - チエノピリミジンジオンacc阻害剤の固体形態およびその生成のための方法 - Google Patents
チエノピリミジンジオンacc阻害剤の固体形態およびその生成のための方法 Download PDFInfo
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- 229960003048 vinblastine Drugs 0.000 description 1
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- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- 229940033942 zoladex Drugs 0.000 description 1
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- 229960002911 zonisamide Drugs 0.000 description 1
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- 229940039925 zyprexa Drugs 0.000 description 1
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Description
本願は、米国特許法第119条第(e)項の下で、米国仮出願第62/302,755号(2016年3月2日出願)および米国仮出願第62/303,237号(2016年3月3日出願)に対する利益を主張する。これらの両方は、本明細書中に参考として援用される。
肥満症は、並はずれて大規模な集団の健康的難局である。肥満症の健康負荷は、成人一人当たり失われた、質を調節された寿命により測定して、喫煙の健康負荷をしのぎ、最も重大な予防可能な死因になっている。米国において、約34%の成人が肥満症を罹患し、1999年の31%から、および1960年〜1980年の約15%から増大している。肥満症は、死亡率を、全ての原因から、男性と女性との両方について、全ての年代において、そして全ての人種および民族の集団において、増大させる。肥満症はまた、社会的非難および差別をもたらし、これは、生活の質を劇的に低下させる。肥満症から生じる慢性疾患は、米国の経済に、体重関連医療費において毎年1500億ドルより多くを支出させる。さらに、肥満集団の約半分、および一般集団の25%が、代謝症候群(腹部肥満症に関連する状態)、高血圧症、増大した血漿中トリグリセリド、低下したHDLコレステロール、およびインスリン抵抗性(2型糖尿病(T2DM)の危険性を増大させる)、脳卒中および灌頂心臓疾患を有する。(Harwood,Expert Opin.Ther.Targets 9:267,2005)。
別の進行中の問題は、広範な真菌性病原体に対して活性を有する抗真菌薬物を欠くことである。しばしば、与えられる抗真菌薬物は、1つの真菌種に対する活性を有するが、密接に関連する種(例えば、Candida albicans、Candida krusei、およびCandida parapsilosis)であってさえも、他の種に対する活性を欠く。
(項目1)
化合物1の結晶形態:
(項目2)
化合物1の結晶形態:
(項目3)
前記回折図が、16.0、24.0、25.8、および27.3°2θ±0.2°2θにおいて、1つまたはそれより多くのさらなるピークを含む、項目2に記載の結晶形態。
(項目4)
化合物1の結晶形態:
(項目5)
約189℃〜約193℃の間に吸熱を含む示差走査熱量測定(DSC)曲線によって特徴付けられる、項目2に記載の結晶形態。
(項目6)
前記結晶形態が、少なくとも約85%の形態Iである、項目2に記載の結晶形態。
(項目7)
化合物1の結晶形態:
化合物1の形態II、化合物1の形態III、化合物1の形態IV、化合物1の形態V、化合物1の形態VI、化合物1の形態VII、化合物1の形態VIII、化合物1ナトリウムの形態I、化合物1ナトリウムの形態II、化合物1カルシウムの形態I、化合物1マグネシウムの形態I、化合物1ジエタノールアミンの形態I、および化合物1ピペラジンの形態Iから選択される、結晶形態。
(項目8)
非晶質化合物1:
(項目9)
前記形態が、結晶性化合物1を実質的に含まない、項目8に記載の非晶質化合物1。
(項目10)
治療有効量の、項目1〜7のいずれか1項に記載の化合物1の結晶形態、および薬学的に受容可能なキャリア、アジュバントまたは希釈剤を含有する、薬学的組成物。
(項目11)
治療有効量の、項目9または10のいずれかに記載の非晶質化合物1、および薬学的に受容可能なキャリア、アジュバント、または希釈剤を含有する、薬学的組成物。
(項目12)
ACCにより媒介される障害を処置する方法であって、該処置を必要とする患者に、項目1〜7のいずれか1項に記載の結晶形態、項目8または9のいずれかに記載の非晶質化合物、あるいは項目10または11のいずれかに記載の薬学的組成物を投与する工程を包含する、方法。
(項目13)
前記ACCにより媒介される障害は、非アルコール性脂肪肝疾患である、項目12に記載の方法。
(項目14)
前記非アルコール性脂肪肝疾患は、非アルコール性脂肪性肝炎である、項目13に記載の方法。
(項目15)
前記ACCにより媒介される障害は、尋常性ざ瘡である、項目12に記載の方法。
(項目16)
化合物1:
化合物G−4−a:
(項目17)
化合物G−4−a:
(項目18)
R H はブロモである、項目17に記載のプロセス。
(項目19)
化合物1:
(項目20)
エナンチオマー富化された式(R)−G−5の化合物:
R 2 は、水素、または必要に応じて置換されたC 1〜6 脂肪族であり;そして
R 5 は、水素またはハロゲンであり;
該プロセスは:
c)式rac−G−5のラセミ化合物
b)該[アシル]基を除去する工程であって;
これによって、該エナンチオマー富化された式(R)−G−5の化合物を調製する、工程を包含する、プロセス。
(項目21)
前記式(R)−G−5の化合物は、(R)−G−5−a:
(項目22)
前記[アシル]ドナーは、必要に応じて置換された4員〜7員ラクトンまたは4員〜7員の必要に応じて置換された環状無水物;あるいは式R x C(O)OR y の化合物であり、ここでR x は、必要に応じて置換されたC 1〜4 脂肪族であり;そしてR y は、必要に応じて置換されたC 1〜4 脂肪族または必要に応じて置換されたC 1〜4 アシルである、項目20または21のいずれか1項に記載のプロセス。
(項目23)
[アシル]はC 4 アシル基である、項目20〜22のいずれか1項に記載のプロセス。
(項目24)
前記リパーゼ酵素は、Candida antarcticaリパーゼBである、項目20〜23のいずれか1項に記載のプロセス。
(項目25)
式:
(項目26)
式:
(項目27)
式(R)−G−8の化合物:
[アシル]はR x C(O)−であり、ここでR x は、必要に応じて置換されたC 1〜4 脂肪族であり;
R a は、窒素、酸素、および硫黄から選択される0個〜2個のヘテロ原子を有する3員〜7員環、ならびにC 1〜6 脂肪族から選択される、必要に応じて置換された基であり;
R 2 は、水素、または必要に応じて置換されたC 1〜6 脂肪族であり;そして
R 5 は、水素またはハロゲンである、
化合物。
(項目28)
R x は、必要に応じて置換されたC 3〜4 脂肪族である、項目27に記載の化合物。
(項目29)
前記化合物は、式(R)−I−1:
(項目30)
前記化合物は、式(R)−I−2:
(項目31)
式(R)−G−1の化合物:
R H は脱離基であり;
R a は、窒素、酸素、および硫黄から選択される0個〜2個のヘテロ原子を有する3員〜7員環、ならびにC 1〜6 脂肪族から選択される、必要に応じて置換された基であり;
R 2 は、水素、または必要に応じて置換されたC 1〜6 脂肪族であり;そして
R 5 は、水素またはハロゲンである、
化合物。
(項目32)
前記化合物は、式H−1:
(項目33)
前記化合物は、式H−2:
(項目34)
R H は、ハロゲンまたはスルホネートである、項目31〜33のいずれか1項に記載の化合物。
(項目35)
R H はブロモである、項目31〜33のいずれか1項に記載の化合物。
(項目36)
R H はメシレートである、項目31〜33のいずれか1項に記載の化合物。
(項目37)
[アシル]はスクシニルである、項目20または21のいずれか1項に記載のプロセス。
(項目38)
前記[アシル]ドナーは無水コハク酸である、項目20〜22のいずれか1項に記載のプロセス。
(項目39)
前記化合物は、式:
(項目40)
前記化合物は、式:
(項目41)
化合物G−9−aを調製する工程は、化合物G−2−a:
(項目42)
化合物1:
(a)化合物G−2−a:
(b)化合物G−9−aを、化合物(R)−G−1−a:
(c)化合物G−4−aを、化合物1を形成するために十分な条件下で加水分解する工程
を包含する、プロセス。
(項目43)
化合物(R)−G−1−aを調製する工程は:
(d)化合物(R)−G−5−aまたはその酸素陰イオン:
(e)化合物(R)−G−6−aを、臭化物塩と、化合物(R)−G−1−aを形成するために十分な条件下で接触させること
を包含する、項目42に記載のプロセス。
(項目44)
化合物1:
(a)化合物(R)−G−5−aまたはその酸素陰イオン:
(b)化合物(R)−G−6−aを、臭化物塩と、化合物(R)−G−1−a:
(c)化合物G−2−a:
(d)化合物G−9−aを、化合物(R)−G−1−aと、化合物G−4−a:
および(e)化合物G−4−aを、化合物1を形成するために十分な条件下で加水分解する工程
を包含する、プロセス。
要旨
本明細書中で化合物1と指定される、化合物(R)−2−(1−(2−(2−メトキシフェニル)−2−((テトラヒドロ−2H−ピラン−4−イル)オキシ)エチル)−5−メチル−6−(オキサゾール−2−イル)−2,4−ジオキソ−1,2−ジヒドロチエノ[2,3−d]ピリミジン−3(4H)−イル)−2−メチルプロパン酸は、式:
(a)化合物G−2−a:
(b)化合物G−9−aを、化合物(R)−G−1−a:
(c)化合物G−4−aを、化合物1を形成するために十分な条件下で加水分解する工程
を包含する。
(a)化合物(R)−G−5−aまたはその酸素陰イオン:
(b)化合物(R)−G−6−aを、臭化物塩と、化合物(R)−G−1−a:
(c)化合物G−2−a:
(d)化合物G−9−aを、化合物(R)−G−1−aと、化合物G−4−a:
(e)化合物G−4−aを、化合物1を形成するために十分な条件下で加水分解する工程
を包含する。
1.一般説明
米国特許出願公開第2013/0123231 A1号(2013年5月16日公開、その全体が本明細書中に参考として援用される)は、アセチルCoAカルボキシラーゼ1および2を結合して阻害する、特定のチエノピリミジンジオン化合物を開示する。このような化合物としては、化合物1:
2.化合物1の固体形態
3.化合物および定義
4.本発明の化合物を提供するための一般方法
Raは、窒素、酸素、および硫黄から選択される0個〜2個のヘテロ原子を有する3員〜7員環、ならびにC1〜6脂肪族から選択される、必要に応じて置換された基であり;
R2は、水素、または必要に応じて置換されたC1〜6脂肪族であり;そして
R5は、水素またはハロゲンである。
スキーム1。式Iの化合物の合成。
スキーム2。式G−1の中間体の合成
スキーム3。式G−5の中間体の合成
スキーム4。式G−4の中間体の代替の合成
スキーム5。式G−2およびG−9の中間体の合成
スキーム6。中間体G−13−aの合成
R2は、水素、または必要に応じて置換されたC1〜6脂肪族であり;そして
R5は、水素またはハロゲンであり;
このプロセスは:
a)式rac−G−5のラセミ化合物:
b)この[アシル]基を除去する工程;
を包含し、これによって、エナンチオマー富化された式(R)−G−5の化合物を調製する。
(a)化合物(R)−G−5−aまたはその酸素陰イオン:
(b)化合物(R)−G−6−aを、臭化物塩と、化合物(R)−G−1−aを形成するために十分な条件下で接触させる工程
を包含する。
(a)化合物G−2−a:
(b)化合物G−9−aを、化合物(R)−G−1−a:
および(c)化合物G−4−aを、化合物1を形成するために十分な条件下で加水分解する工程
を包含する。
(a)化合物(R)−G−6−a:
(b)化合物G−2−a:
(c)化合物G−9−aを、化合物(R)−G−1−aと、化合物G−4−a:
および(d)化合物G−4−aを、化合物1を形成するために十分な条件下で加水分解する工程
を包含する。
(a)化合物(R)−G−5−aまたはその酸素陰イオン:
(b)化合物(R)−G−6−aを、臭化物塩と、化合物(R)−G−1−a:
(c)化合物G−2−a:
(d)化合物G−9−aを、化合物(R)−G−1−aと、化合物G−4−a:
および(e)化合物G−4−aを、化合物1を形成するために十分な条件下で加水分解する工程
を包含する。
5.中間体化合物
[アシル]はRxC(O)−であり、ここでRxは、必要に応じて置換されたC1〜4脂肪族であり;
Raは、窒素、酸素、および硫黄から選択される0個〜2個のヘテロ原子を有する3員〜7員環、ならびにC1〜6脂肪族から選択される、必要に応じて置換された基であり;
R2は、水素、または必要に応じて置換されたC1〜6脂肪族であり;そして
R5は、水素またはハロゲンである。
RHは脱離基であり;
Raは、窒素、酸素、および硫黄から選択される0個〜2個のヘテロ原子を有する3員〜7員環、ならびにC1〜6脂肪族から選択される、必要に応じて置換された基であり;
R2は、水素、または必要に応じて置換されたC1〜6脂肪族であり;そして
R5は、水素またはハロゲンである。
薬学的使用
併用療法
nTM、Zinecard(登録商標)、Zoladex(登録商標)、ゾレドロン酸、ゾリンザ(Zolinza)、ゾメタ(登録商標)、あるいは上記のものの任意のものの組み合わせが挙げられるが、これらに限定されない。
いくつかの実施形態において、提供される化合物、またはその薬学的に受容可能な組成物は、1つまたはそれより多くのさらなる治療剤と併用して投与され、ここでこのさらなる治療剤のうちの少なくとも1つは、ファルネソイドX受容体(FXR)アゴニストである。いくつかの実施形態において、このFXRアゴニストは、INT−747(オベチコール酸)である。いくつかの実施形態において、このFXRアゴニストはPX−102である。
以下の実施例に記載されるように、特定の例示的実施形態において、化合物および固体形態は、前述の一般手順に従って調製される。本発明の化合物の合成を記載するが、以下の方法および当業者に公知である他の方法が、全ての化合物、ならびに本明細書中に記載されるようなこれらの化合物の各々のサブクラスおよび種に適用され得ることが、理解される。
実験手順:
実施例1。非晶質化合物1の生成
実施例2。化合物1の形態Iの生成
実施例3。化合物1の形態IIの生成
実施例4。化合物1の形態IIIの生成
実施例5。化合物1の形態IVの生成
実施例6。化合物1の形態Vの生成
実施例7。化合物1の形態VIの生成
実施例8。化合物1の形態VIIの生成
実施例9。化合物1の形態VIIIの生成
実施例10。形態Iと形態VIIとの競合的スラリー化
実施例11。形態Iと形態VIIIとの競合的スラリー化
実施例12。形態Iと形態VIIIとの競合的スラリー化
実施例13。化合物1ナトリウムの形態Iの生成
実施例14。化合物1ナトリウムの形態IIの生成
実施例15。化合物1カルシウムの形態Iの生成
実施例16。化合物1マグネシウムの形態Iの生成
実施例17。化合物1ジエタノールアミンの形態Iの生成
実施例18。化合物1ピペラジンの形態Iの生成
実施例19。X線粉末回折(XRPD)分析方法A
実施例22。熱重量/示差熱分析(TG/DTA)
実施例23。示差走査熱量測定法(DSC)
実施例24。カール−フィッシャークーロン滴定(KF)
実施例25。赤外分光器(IR)
実施例27。高速液体クロマトグラフィー−紫外吸収検出(HPLC−UV)。
実施例29。LogPおよびLogDの決定
実施例30。薬学的組成物
実施例31。微粒化
実施例32。ホットメルト高剪断造粒、粉砕、およびブレンド
実施例33。カプセル調製
実施例34。中間体(R)−G−1−aの合成
代替の工程1:rac−G−7−aの合成
工程2。rac−G−5−aの合成
代替の工程2:rac−G−5−aの合成
工程3。(R)−G−5−aの合成
代替の工程3:(R)−G−5−aの代替の合成
工程4。(R)−G−6−aの合成
代替の工程4。(R)−G−6−aの合成
工程5。(R)−G−1−aの合成
(R)−G−1−aの代替の合成
実施例35。化合物1の合成−経路A
工程2。5−ブロモ−4−メチル−2−[3−(1−メチル−1−tert−ブトキシカルボニルエチル)ウレイド]−3−テン酸エチルの合成
工程3。2−(2−ブロモ−3−メチル−4,6−ジオキソ−1−チア−5,7−ジアザ−5,7−ジヒドロインデン−5−イル)−2−メチルプロピオン酸tert−ブチル(G−2−a)の合成
G−2−aへの代替のプロセス
工程4。2−(2−ブロモ−3−メチル−4,6−ジオキソ−1−チア−5,7−ジアザ−5,7−ジヒドロインデン−5−イル)−2−メチルプロピオン酸の合成
工程5。2−(2−ブロモ−3−メチル−4,6−ジオキソ−1−チア−5,7−ジアザ−5,7−ジヒドロインデン−5−イル)−2−メチルプロピオン酸ベンジル(G−2−b)の合成
工程6。2−{7−[(R)−2−(o−メトキシフェニル)−2−(テトラヒドロ−2H−ピラン−4−イルオキシ)エチル]−2−ブロモ−3−メチル−4,6−ジオキソ−1−チア−5,7−ジアザ−5,7−ジヒドロインデン−5−イル}−2−メチルプロピオン酸ベンジル(G−3−b)の合成
工程7。G−4−bの合成
工程8。G−4−bからの化合物1の合成
実施例36。化合物1の合成−経路B
G−9−aの代替の合成2
G−9−aの代替の合成3
G−9−aの代替の合成4
G−9−aの代替の合成5
G−9−aの代替の合成6
工程2。2−{7−[(R)−2−(o−メトキシフェニル)−2−(テトラヒドロ−2H−ピラン−4−イルオキシ)エチル]−3−メチル−2−(1,3−オキサゾール−2−イル)−4,6−ジオキソ−1−チア−5,7−ジアザ−5,7−ジヒドロインデン−5−イル}−2−メチルプロピオン酸tert−ブチル(G−4−a)の合成
G−4−aの代替の合成
工程3。化合物1の合成
化合物1の代替の合成
実施例37。酵素分割スクリーニング
研究A
実施例40。正常および損なわれた肝機能を有する被験体における化合物1の研究
組み入れ基準
・肝臓の機能不全は別として、研究者の意見では、被験体は、病歴、健康診断、バイタルサインそしてスクリーニングの実験室評価に基づき、研究に参加するために十分に健康でなければならない
・研究薬投与(1日目)前の3ヵ月(または90日)以内に、臨床的に有意な変化のない、長期的(6ヵ月超)の安定した肝障害の診断を有し得る
・スクリーニング時の以下の実験室パラメーターの全てを満たし得る:
・アラニンアミノトランスフェラーゼ(以前は、血清グルタミン酸ピルビン酸トランスアミナーゼ)(ALT)値≦10×正常値上限(ULN)
・アスパラギン酸アミノトランスフェラーゼ(AST)≦10×ULN
・好中球絶対数≧1,000/mm3
・血小板≧25,000/mm3
・ヘモグロビン≧8g/dL
・α−フェトプロテイン≦50ng/mL
・軽度の肝障害を有する被験体は、スクリーニング時にChild Pugh Turcotte尺度で5〜6のスコアを有さなければならない。被験体のスコアが研究の過程で変化する場合、スクリーニング時のスコアが分類に使用される
・中等度の肝障害を有する被験体は、スクリーニング時にChild Pugh Turcotte尺度で7〜9のスコアを有さなければならない。被験体のスコアが研究の過程で変化する場合、スクリーニング時のスコアが分類に使用される
・重度の肝障害を有する被験体は、スクリーニング時にChild Pugh Turcotte尺度で10〜15のスコアを有さなければならない。被験体のスコアが研究の過程で変化する場合、スクリーニング時のスコアが分類に使用される
・薬物治療を要する肝障害と関連しない併存疾患を伴う、肝障害を有する被験体は、スクリーニング前の少なくとも4週(または5半減期のどちらか長い方)にわたり、用量を変化させることなく薬物治療を受けなければならない。この時間枠中の投薬量のあらゆる変更が、スポンサーによって再考および承認されるべきである。
投薬と投与
・処置群A:化合物1 5mgを1日1回経口投与;
・処置群B:化合物1 20mgを1日1回経口投与;
・処置群C:プラセボを1日1回経口投与。
・QoL質問票(Short Form(36)健康調査(SF−36)、労働生産性および活動障害(World Productivity and Activity Impairment(WPAI))ならびに慢性肝疾患質問票(Chronic Liver Disease questionnaire(CLDQ)))。注記:QoL質問票は、実施されるあらゆる研究手順の前でかつ、被験体が医療提供者に会う前に完了されることが推奨される。
・症状に合った(Symptom driven)身体検査
・バイタルサイン、腹囲および体重を記録する
・化学、血液学、凝固パネル、脂質プロフィール、ヘモグロビンA1c、バイオマーカー、またはゲノム検査(被験体が任意のゲノム研究への参加に同意した場合のみ)のための血液試料を取得する
・標準12誘導ECGを実施する
・FibroScan(登録商標)を実施する(利用可能な場合)
・妊娠可能な女性のみに関する尿妊娠検査またはバイオマーカーのための尿サンプルを採取する
・バイオマーカーのための大便サンプルを採取する(指示についてはStudy Reference Binderを参照)
・研究薬を配り、適切な投薬および投与に関する指示を被験体に提供する;被験体は、現場で研究薬のベースライン/1日目の用量を摂取する
・MREデータを採取する
・MRI−PDFFデータを採取する
・以前の来診以降に被験体が摂取したすべての併用薬物治療を記録する
・任意の重篤な有害事象、そして、スクリーニング来診以降に生じたすべての有害事象を記録する。
Claims (8)
- 前記回折図が、16.0、24.0、25.8、および27.3°2θ±0.2°2θにおいて、1つまたはそれより多くのさらなるピークを含む、請求項1に記載の結晶。
- 189℃〜193℃の間に吸熱を含む示差走査熱量測定(DSC)曲線によって特徴付けられる、請求項1に記載の結晶。
- 治療有効量の、請求項1〜3のいずれか1項に記載の化合物1の結晶、および薬学的に受容可能なキャリア、アジュバントまたは希釈剤を含有する、薬学的組成物。
- ACCにより媒介される障害を処置するための組成物であって、請求項1〜3のいずれか1項に記載の化合物1の結晶、あるいは請求項4に記載の薬学的組成物を含有する、組成物。
- 前記ACCにより媒介される障害は、非アルコール性脂肪肝疾患である、請求項5に記載の組成物。
- 前記非アルコール性脂肪肝疾患は、非アルコール性脂肪性肝炎である、請求項6に記載の組成物。
- 前記ACCにより媒介される障害は、尋常性ざ瘡である、請求項5に記載の組成物。
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