JP2019523229A - 抗微生物化合物及びその使用方法 - Google Patents
抗微生物化合物及びその使用方法 Download PDFInfo
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- JP2019523229A JP2019523229A JP2018565820A JP2018565820A JP2019523229A JP 2019523229 A JP2019523229 A JP 2019523229A JP 2018565820 A JP2018565820 A JP 2018565820A JP 2018565820 A JP2018565820 A JP 2018565820A JP 2019523229 A JP2019523229 A JP 2019523229A
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Classifications
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
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Abstract
Description
本発明の目的はまた、既存の抗生物質の抗菌効果を増強する化合物を提供することである。
本発明の更なる目的は、細菌感染症を治療するための組成物を提供することである。
本発明の別の目的は、微生物感染を有する対象を治療するための方法を提供することである。
本発明の目的はまた、薬剤耐性細菌感染と戦うために使用可能な抗菌活性を有する化合物を提供することである。
Zは、O、S、CR11R12、又はNR13であり;
R1、R2、R9、R10、R11、R12、R13、R14、及びR15は、独立して、空位、水素、−C(O)R18、−C(W)NR19R20、又は、置換若しくは無置換のアルキル、アルケニル、アルキニル、アルコキシ、シクロアルキル、ヘテロサイクリル、シクロアルケニル、ヘテロシクロアルケニル、アリ−ル、ヘテロアリ−ル、アロキシ、アリ−ルアルキル、ヘテロアルキル、アルキルアリ−ル、ハロゲン、アルキルヘテロアリ−ル、−NR16R17であり;R16及びR17は、独立して、水素、置換若しくは無置換のアルキル、アルケニル、アルキニル、シクロアルキル、ヘテロサイクリル、シクロアルケニル、ヘテロシクロアルケニル、アリ−ル、ヘテロアリ−ル、アリ−ルアルキル、ヘテロアルキル、アルキルアリ−ル、又はアルキルヘテロアリ−ルであり;
R18は、水素、ヒドロキシル、又は、置換若しくは無置換のアルキル、アルケニル、アルキニル、シクロアルキル、アルコキシ、ヘテロサイクリル、シクロアルケニル、ヘテロシクロアルケニル、アリ−ル、アロキシ、ヘテロアリ−ル、アリ−ルアルキル、ヘテロアルキル、アルキルアリ−ル、又はアルキルヘテロアリ−ルであり;
Wは、O、S、又はNR21であり;
R19、R20、及びR21は、独立して、水素、置換若しくは無置換アルキル、アルケニル、アルキニル、シクロアルキル、ヘテロサイクリル、シクロアルケニル、ヘテロシクロアルケニル、アリ−ル、ヘテロアリ−ル、アリ−ルアルキル、ヘテロアルキル、アルキルアリ−ル、又はアルキルヘテロアリ−ルであり;
Aは、二重結合又は単結合であり;
R15は、Aが二重結合である場合には存在しない。
本明細書における値の範囲の列挙は、本明細書中に別段の指示がない限り、範囲内の各別個の値を個々に参照する簡易的な方法として役立つことを意図しており、それぞれの個別値は、本明細書中に、個別に列挙されているかのように組み入れられる。
「エマルジョン」は、共に均一に混合された非混和性成分の混合物を含有する組成物である。
本明細書で使用される「ゲル」は、分散相が連続相と組み合わされてゼリ−などの半固体材料を生成するコロイドである。
本明細書で使用する「疎水性」は、水に対する親和性を欠いた物質を指し、水と反発すると共に、水を吸収したり、水に溶けたり水と混ざり合ったりしない傾向にある。
本明細書で使用する「親油性」は、脂質に対する親和性を有する化合物を指す。
本明細書で使用される「オイル」は、少なくとも95重量%の親油性物質を含んだ組成物である。親油性物質の例としては、天然及び合成油、脂肪、脂肪酸、レシチン、トリグリセリド、並びにそれらの組み合わせが挙げられるが、これらに限定されるものではない。
「軟膏」は、軟膏基剤及び任意に1つ又は複数の活性剤を含有する半固体製剤である。
ハイスル−プットスクリ−ニングは、抗菌剤として新しい小分子を発見する良い機会を提供する。
開示された化合物は、以下の一般式Iによって表される:
Zは、O、S、CR11R12、又はNR13であり;
R1、R2、R9、R10、R11、R12、R13、R14、及びR15は、独立して、空位、水素、−C(O)R18、−C(W)NR19R20、又は、置換若しくは無置換のアルキル、アルケニル、アルキニル、アルコキシ、シクロアルキル、ヘテロサイクリル、シクロアルケニル、ヘテロシクロアルケニル、アリ−ル、ヘテロアリ−ル、アロキシ、アリ−ルアルキル、ヘテロアルキル、アルキルアリ−ル、ハロゲン、アルキルヘテロアリ−ル、−NR16R17であり;R16及びR17は、独立して、水素、置換若しくは無置換のアルキル、アルケニル、アルキニル、シクロアルキル、ヘテロサイクリル、シクロアルケニル、ヘテロシクロアルケニル、アリ−ル、ヘテロアリ−ル、アリ−ルアルキル、ヘテロアルキル、アルキルアリ−ル、又はアルキルヘテロアリ−ルであり;
R18は、水素、ヒドロキシル、又は、置換若しくは無置換のアルキル、アルケニル、アルキニル、シクロアルキル、アルコキシ、ヘテロサイクリル、シクロアルケニル、ヘテロシクロアルケニル、アリ−ル、アロキシ、ヘテロアリ−ル、アリ−ルアルキル、ヘテロアルキル、アルキルアリ−ル、又はアルキルヘテロアリ−ルであり;
Wは、O、S、又はNR21であり;
R19、R20、及びR21は、独立して、水素、置換若しくは無置換アルキル、アルケニル、アルキニル、シクロアルキル、ヘテロサイクリル、シクロアルケニル、ヘテロシクロアルケニル、アリ−ル、ヘテロアリ−ル、アリ−ルアルキル、ヘテロアルキル、アルキルアリ−ル、又はアルキルヘテロアリ−ルであり;
Aは、二重結合又は単結合であり;
R15は、Aが二重結合である場合には存在しない。
表8:式IIAの置換基の例
いくつかの形態では、R1は3又は5位にあり;R1は4位にあり;R1は2又は6位にあり;いくつかの形態では、R6は4位にある。いくつかの形態では、R7は、2又は6位にある。いくつかの形態では、R2は、3、4又は5位にある。
いくつかの形態では、化合物は、式IIAによって表される。
式Iで表される化合物の薬学的に許容される塩、及びその誘導体、並びにDHFR(ジヒドロ葉酸レダクタ−ゼ)に結合すると判定された他の化合物も本明細書中に開示される。薬学的に許容される塩の例としては、アミンなどの塩基性残基の無機又は有機酸塩;カルボン酸などの酸性残基のアルカリ又は有機塩が挙げられるが、これらには限られない。薬学的に許容される塩には、例えば非毒性の無機酸又は有機酸から形成された親化合物の従来の非毒性塩又は第4級アンモニウム塩も含まれる。このような従来の非毒性塩には、塩酸、臭化水素酸、硫酸、スルファミン酸、リン酸、及び硝酸などの無機酸から誘導されるもの;並びに、酢酸、プロピオン酸、コハク酸、グリコ−ル酸、ステアリン酸、乳酸、リンゴ酸、酒石酸、クエン酸、アスコルビン酸、パモ酸、マレイン酸、ヒドロキシマレイン酸、フェニル酢酸、グルタミン酸、安息香酸、サリチル酸、スルファニル酸、2−アセトキシ安息香酸、フマル酸、トルエンスルホン酸、ナフタレンスルホン酸、メタンスルホン酸、エタンジスルホン酸、シュウ酸、及びイセチオン塩などの有機酸から誘導される塩が含まれる。
バ−チャルリガンドスクリ−ニングを用いて本明細書で同定された化合物は、出発化合物又は中間化合物として、出発化合物又は中間化合物と比較して、DHFRなどの酵素への結合の増強、又は、DHFRなどの酵素への抑制の増強を示す、最終化合物の産生に使用され得る。本明細書で同定された化合物は、バイオアベイラビリティを増加させ、血流中の半減期を延長し、溶解度を増加させ、親水性を増大させ、疎水性を増加させ、又はこれらの組合せをするために、従来技術を用いて修飾することができる。この化合物は、イオン化するか又は水との分子間力による親和性(水素結合)を比較的強くすることが可能な、アルコ−ル、アミン、アミド、カルボン酸、スルホン酸及びリン酸基などの極性官能基を導入するように修飾してもよく、これにより、通常は、水溶性が増した類似体(アナログ)が得られる。酸性及び塩基性基は、これらの基を用いて塩を形成し、最終製品のためのより広い範囲の剤形が得られるので、特に有用である。しかしながら、塩基又は塩基性基を含む構造に酸性基を導入するか、又は、酸性基を含む構造に塩基性基を導入することによって、両性イオンを形成することにより、水溶性を低下させることもできる。カルボン酸エステル、ハロゲン化アリ−ル、及びハロゲン化アルキルなどの弱極性基の導入は、水溶性を有意には向上させず、脂質溶解性を高めることができる。
本明細書に開示される化合物と共に使用することができる他の生物活性剤には、抗菌剤、特には、抗生物質、消毒剤、抗瘢痕剤、及び抗炎症剤が含まれるが、これらに限定されない。
本明細書に記載の化合物は、経腸、非経口、局所、又は肺投与用に製剤化することができる。化合物は、安全かつ有効であると考えられ、望ましくない生物学的副作用又は望ましくない相互作用を引き起こすことなく個体に投与され得る、1つ又は複数の薬学的に許容される担体及び/又は賦形剤と組み合わせることができる。担体は、1つ又は複数の活性成分以外の医薬製剤中に存在する全ての成分である。
本明細書に記載の化合物は、非経口投与のために製剤化することができる。例えば、非経口投与は、静脈内、皮内、動脈内、腹腔内、病巣内、頭蓋内、関節内、静翼内、胸腔内、気管内、硝子体内、腫瘍内、筋肉内、皮下、結膜下、結膜内、嚢内、腔内、注射、及び注入による患者への投与が含まれ得る。
本明細書に記載の非経口製剤は、即時放出、遅延放出、延長放出、拍動放出、及びそれらの組み合わせを含む制御放出のために製剤化することができる。
非経口投与のために、1つ又は複数の化合物及び任意の1つ又は複数の追加の活性成分を、微粒子、ナノ粒子、又はそれらの組み合わせに組み込むことができる。これにより、1つ又は複数の化合物及び/又は1つ又は複数の追加の活性成分の制御された放出が提供される。製剤が2種以上の薬剤を含有する形態では、同じタイプの制御放出(例えば、遅延型、延長型、即時型、又は拍動性)を行うように製剤化することができる。また、この形態では、薬剤を独立に配合して、異なった形態の放出(例えば、即時及び遅延、即時及び拡張、遅延及び拡張、遅延及び脈動など)を行うように製剤化することもできる。
薬剤含有微粒子を生成するための担体材料へのカプセル化又は薬物の組み込みは、既知の医薬製剤技術によって達成することができる。脂肪、ワックス、又はワックス様物質の製剤の場合、担体物質は、典型的には、その融解温度より上に加熱され、薬剤が添加されて、担体物質中に薬剤粒子が懸濁した混合物、担体物質中に溶解した薬剤、又はこれらの組合せが形成される。マイクロ粒子は、限定するものではないが、凝結、押出、噴霧冷却又は水性分散のプロセスを含むいくつかの方法によって次いで配合され得る。好ましい方法では、ワックスがその融点以上に加熱され、薬剤が加えられ、混合物が冷却するにつれて、溶融したワックス−薬剤混合物が一定の攪拌下で凝固される。或いは、溶融したワックス−薬剤混合物を押し出し、球状化して、ペレット又はビ−ズを形成することができる。これらのプロセスは、当該技術分野で知られている。
本明細書に記載の化合物は、ポリマ−インプラントなどの注射可能/移植可能な固体又は半固体のインプラントに組み込むことができる。いくつかの形態では、化合物は、室温で液体又はペ−ストであるポリマ−に組み込まれるが、生理学的流体などの水性媒体と接触すると、粘性の増加を示して、半固体又は固体材料を形成する。代表的なポリマ−には、少なくとも1つの不飽和ヒドロキシ脂肪酸とヒドロキシアルカン酸との共重合に由来する、ヒドロキシアルカン酸ポリエステルが含まれるが、これに限定されない。ポリマ−は、溶融され、活性物質と混合され、キャスティング又は射出成形されて、デバイスに入れることができる。このような溶融製作には、供給されるべき物質及びポリマ−が分解するか又は反応性になる温度よりも低い融点を有するポリマ−が必要である。このデバイスはまた、ポリマ−を溶媒に溶解し、薬剤をポリマ−溶液に溶解又は分散させ、溶媒を蒸発させる、溶媒キャスティングによって調製することもできる。溶媒プロセスは、ポリマ−が有機溶媒に可溶であることを必要とする。別の方法は、ポリマ−と薬剤又は活性剤が充填されたポリマ−粒子との混合粉末の圧縮成形である。
経口製剤は、医薬グレ−ドのマンニト−ル、ラクト−ス、ナトリウムサッカリン、デンプン、ステアリン酸マグネシウム、セルロ−ス、炭酸マグネシウムなどの標準的な担体を含むことができる。このような組成物は、使用される投与様式に基づいて患者に適切な形態を提供するために、治療有効量の化合物及び/又は抗生物質を適切な量の担体と一緒に含むであろう。適切な経口剤形には、錠剤、カプセル、溶液、懸濁液、シロップ、及びロゼンジが含まれる。錠剤は、当技術分野で周知の圧縮又は成形技術を用いて作製することができる。ゼラチンカプセル又は非ゼラチンカプセルは、当技術分野で周知の技術を用いて、液体、固体及び半固体の充填材料をカプセル化することができる硬質又は軟質カプセル殻として調製することができる。
カプセル、錠剤、溶液及び懸濁液などの経口剤形は、制御放出のために製剤することができる。例えば、1つ又は複数の化合物及び任意の1つ又は複数の追加の活性成分は、ナノ粒子、マイクロ粒子、及びそれらの組み合わせへと配合され、軟質若しくは硬質ゼラチン又は非ゼラチンカプセルにカプセル化されるか、又は、分散媒体中に分散されて、経口懸濁液又はシロップを形成することができる。粒子は、薬剤及び制御放出ポリマ−又はマトリックスから形成することができる。或いは、薬剤粒子は、最終剤形に組み込む前に、1つ以上の制御放出コ−ティングで被覆することができる。
徐放性製剤は、一般に、当該分野で公知の拡散システム又は浸透システムとして調製される。拡散システムは、典型的には、リザ−バとマトリクスとの2種類のデバイスからなる。これは周知であり、当技術分野で説明されている。マトリックスデバイスは、一般に、徐々に溶解するポリマ−担体を用いて薬剤を錠剤の形態に圧縮することによって調製される。マトリックスデバイスの調製に使用される3つの主なタイプの材料は、不溶性プラスチック、親水性ポリマ−、及び脂肪族化合物である。プラスチックマトリックスには、メチルアクリレ−ト−メチルメタクリレ−ト、ポリ塩化ビニル、及びポリエチレンが含まれるが、これらに限定されない。親水性ポリマ−には、メチル及びエチルセルロ−スなどのセルロ−ス系ポリマ−、ヒドロキシプロピルセルロ−ス、ヒドロキシプロピルメチルセルロ−スなどのヒドロキシアルキルセルロ−ス、カルボキシメチルセルロ−スナトリウム、カ−ボポル(登録商標)934、ポリエチレンオキシド、及びそれらの混合物が含まれるが、これらに限定されない。脂肪酸化合物には、カルナウバワックス及びグリセリルトリステアレ−トなどの様々なワックス、水素化ヒマシ油又は水素化植物油を含むワックス型物質、又はそれらの混合物が含まれるが、これらに限定されない。
遅延放出製剤は、固体投与形態を、胃の酸性環境に不溶であり、小腸の中性環境に可溶なポリマ−フィルムで被覆することによって作製することができる。
局所投与のための適切な剤形としては、クリ−ム、軟膏、膏薬、スプレ−、ゲル、ロ−ション、エマルジョン、及び経皮パッチが挙げられる。製剤は、経粘膜、経上皮、経内皮、又は経皮投与のために処方され得る。化合物はまた、鼻腔内送達、肺送達、又は吸入のために処方され得る。組成物は、1つ又は複数の化学的浸透増強剤、膜透過性剤、膜輸送剤、皮膚軟化剤、界面活性剤、安定剤、緩衝剤、及びそれらの組み合わせをさらに含み得る。
エマルジョンは、第2の液体の全体に小さな球として分布する1つの液体の調製物である。特定の形態では、エマルジョンの非混和性成分は、親油性成分及び水性成分を含む。分散液は不連続相であり、分散媒は連続相である。油が分散液であり、水溶液が連続相である場合、それは水中油型エマルジョンとして知られ、一方、水又は水溶液が分散相であり、油又は油性物質が連続相である場合、それは油中水型エマルジョンとして知られている。油相及び水相のいずれか又は両方は、1つ又は複数の界面活性剤、乳化剤、乳化安定剤、緩衝剤、及び他の賦形剤を含有してもよい。好ましい賦形剤としては、界面活性剤、特に非イオン性界面活性剤;乳化剤、特に乳化ワックス;液体不揮発性非水性材料、特にプロピレングリコ−ルなどのグリコ−ルが挙げられる。油相は、他の薬学的に認可された油性の賦形剤を含み得る。例えば、ヒドロキシル化ヒマシ油又はゴマ油などの物質は、界面活性剤又は乳化剤として油相に使用され得る。
ロ−ションは、懸濁剤及び分散剤の使用によって分散媒体に可溶性である細かく粉末化された物質を含有することができる。或いは、ロ−ションは、ビヒクルと不混和性の液体物質を分散相として有することができ、通常、乳化剤又は他の適切な安定剤によって分散される。いくつかの形態では、ロ−ションは、100〜1000センチスト−クスの粘度を有するエマルジョンの形態である。ロ−ションの流動性は、広い表面積にわたって迅速かつ均一な適用を可能にする。ロ−ションは、典型的には、皮膚上で乾燥させることを意図しており、これにより、医薬成分の薄い被膜が皮膚の表面上に残る。
クリ−ムは、乳化剤及び/又は他の安定化剤を含有してもよい。いくつかの形態では、製剤は、1000センチスト−クスを超える、典型的には20,000〜50,000センチスト−クスの範囲の粘度を有するクリ−ムの形態である。クリ−ムは、一般に、より広がりやすく、簡単に取り除くことができるため、軟膏に比べて好まれることがしばしばある。クリ−ムとロ−ションとの違いは粘度であり、これは様々な油の量/使用や製剤を調製するために使用される水の割合に依存する。クリ−ムは、典型的にはロ−ションよりも厚く、様々な用途があり、多くの場合、より多くの様々なオイル/バタ−を使用し、所望の効果を皮膚に与える。クリ−ム処方では、水ベ−スの割合は約60〜75%であり、油ベ−スは全体の約20〜30%であり、他の割合は乳化剤、防腐剤、及び添加剤であり、合計で100%である。
適切な軟膏基剤の例には、炭化水素基剤(例えば、ペトロラタム、白色ワセリン、黄色軟膏、及び鉱油);吸収基剤(親水性ペトロラタム、無水ラノリン、ラノリン、及び冷たいクリ−ム);水−除去可能基剤(例えば、親水性軟膏)、及び水溶性基剤(例えば、ポリエチレングリコ−ル軟膏)を含むが、これらに限定されない。ペ−ストは、典型的には、固形分の割合がより多いという点で、軟膏とは異なる。ペ−ストは、典型的には、同じ成分で調製された軟膏よりも吸収性があり、滑りにくい。
ゲルは、液体ビヒクル中に溶解又は懸濁した増粘剤又はポリマ−材料の作用によって半固体にされる、液体ビヒクル中の小分子又は大分子の分散体を含む半固体システムである。液体は、親油性成分、水性成分、又はその両方を含むことができる。いくつかのエマルジョンはゲルであってもよく、そうでなければゲル成分を含んでいてもよい。しかしながら、一部のゲルは、混和しない成分の均質な混合物を含まないため、エマルジョンではない。適切なゲル化剤としては、ヒドロキシプロピルセルロ−ス及びヒドロキシエチルセルロ−スなどの変性セルロ−ス;カルボポ−ルホモポリマ−及びコポリマ−;並びにそれらの組み合わせが挙げられるが、これらには限定されない。液体ビヒクル中の適切な溶媒には、ジグリコ−ルモノエチルエ−テル;プロピレングリコ−ルなどのアルキレングリコ−ル;ジメチルイソソルビド;イソプロピルアルコ−ル及びエタノ−ルアルコ−ルが挙げられるが、これらには限定されない。溶媒は、典型的には、薬剤を溶解する能力のために選択される。製剤の皮膚感触及び/又はエモリエンシ−を改善する他の添加剤も組み込むことができる。このような添加剤の例には、ミリスチン酸イソプロピル、酢酸エチル、C12−C15アルキルベンゾエ−ト、鉱油、スクワラン、シクロメチコン、カプリン酸/カプリル酸トリグリセリド、及びそれらの組み合わせが挙げられるが、これらには限定されない。
発泡体は、エマルジョンとガス状推進剤との組み合わせで構成される。ガス状推進剤は、主としてヒドロフルオロアルカン(HFAs)から構成される。適切な推進剤には、1,1,1,2−テトラフルオロエタン(HFA 134a)及び1,1,1,2,3,3,3−ヘプタフルオロプロパン(HFA 227)などのHFAsが含まれるが、医療用途のために現在承認されているか、又は承認されるかもしれない、これらと他のHFAの混合物及び混和物も好適である。推進剤は、好ましくは、噴霧中に可燃性又は爆発性の蒸気を発生させ得る炭化水素推進剤ガスではない。更に、組成物は、好ましくは、使用中に可燃性又は爆発性の蒸気を生成し得る揮発性アルコ−ルを含まない。
これらの化合物は、洗浄用組成物に配合することができる。清浄用組成物は、家庭用洗浄用途(例えば、床、カウンタ−トップ、タブ、皿などの硬い表面、衣類、スポンジ、ペ−パ−タオルなどの柔らかい布材料)、パ−ソナルケア用途(例えば、ロ−ション、シャワ−ジェル、石鹸、シャンプ−、ワイプ)、工業用及び病院用用途(例えば、器具、医療機器、手袋の滅菌)に非常に有効である。これらの製剤は、グラム陰性細菌及びグラム陽性細菌に感染又は汚染された表面を洗浄するのに有効である。
本明細書に開示される方法は、抗バクテリア剤に対する細菌耐性に対抗するための2つのアプロ−チを使用する。第1の方法は、既存の抗生物質と組み合わせて本明細書に開示される化合物を使用する。この戦略は、細菌が生存するのに必要な抵抗因子を獲得するためのハ−ドルを高くし、同時に抵抗性株の上昇を遅らせる。本明細書に記載された方法は、既存の抗生物質の使用を維持し、これにより、これらの抗生物質の臨床寿命を延ばし、新しい世代の抗生物質の開発のための時間をもたらす。この併用療法は、耐性株の出現のためのより大きなハ−ドルを据え付けるのみならず、本明細書中に開示される化合物は、共投与される抗生物質の効果を強化する。第2のアプロ−チは、細菌の病原因子を標的とするものである。病原因子は、細菌の生存のための補助遺伝子であるため、化学遺伝学的方法によって不活性化されたそれらの遺伝子を有することは、細菌に対して直接的な増殖の問題をもたらさないだろう。これは、エスケ−プ突然変異体を発生させる可能性を低減し、耐性株の発生を減少させるであろう。
開示された化合物で阻害することができる例示的な微生物には、限定されるものではないが、Staphylococcus aureus、Pseudomonas aeruginosa、Burkholderia cepacia Enterococcus faecalis、Enterococcus faecium、及び、Streptococcus pneumoniaeが含まれる。好ましい形態には、Staphylococcus aureusのメチシリン耐性株、及び、多剤耐性のListeria monocytogenes、Pseudomonas aeruginosa、Burkholderia cepacia、Enterococcus faecalis、Streptococcus pneumoniaeが含まれる。
開示された化合物及びその誘導体並びにそれらの組み合わせは、対象、好ましくはヒト対象に感染する上記の微生物によって引き起こされる感染から生じる症状を改善又は治療するのに有効な量で、上述したように投与することができる。感染症は、全身性又は局所性であり得る。感染症は、皮膚、目、喉、鼻、若しくは耳、又は、肺、腸、心臓、脳及び肝臓を含むがこれらに限定されない任意の器官の感染症であり得る。感染症は、膿瘍又は傷であってもよい。
本明細書に開示される化合物は、例えば病院又は医療施設からのハ−ドウェアなどの高リスク環境において、滅菌剤として使用することができる。世界保健機関(WHO)は、いつでも、世界中の140万人以上の人々が病院で得た感染症の影響を受けていると推定している。洗浄、消毒、及び滅菌は命を救い、患者の結果を改善する。先進国の現代病院に入院した患者の5%〜10%が、1つ又は複数の医療関連感染症を発症する。疾病管理予防センタ−(CDC)は、米国の病院で毎年約170万件の医療関連感染が発生し、毎年約10万人の死亡に関連していると推定している。医療関連感染症は、介護施設やリハビリテ−ション施設などの介護施設の重要な問題でもある。医療関連病原体の伝達は、様々な患者ケア活動中に不注意に手を汚染する医療従事者の手によって、最も頻繁に起こる。それほど頻繁ではないが、医療施設内の汚染された表面は、医療関連病原体の拡散に寄与する可能性がある。
さらに、記載された治療方法は、対象における治療に適用されるだけでなく、細胞培養物、器官、組織又は個々の細胞に、in vivo、ex vivo又はin vitroで適用され得ることが、当業者に理解されるであろう。
さらに、医薬組成物を包装するために包装材料が利用される場合、それは、プラスチックポリマ−、シリコ−ンなどのように、生物学的に不活性であるか生物活性が欠如していてもよく、化合物/抗生物質の有効性に影響を及ぼすことなく、包装され及び/又はそれと共に運搬される。
細菌株:Mu3(ATCC 700698)、USA300、COLは、Staphylococcus aureusのメチシリン耐性株である。Newman、ATCC29213、RN4220、RN6390は、メチシリン感受性株である。AE−052、ST−45−502、ST−239−IIIA−503、ST−239−III−AH−504は、香港のクイ−ン・メアリ−病院の臨床分離株である。Listeria monocytogenes(L.monocytogenes)、Pseudomonas aeruginosa(P.aeruginosa)PA01、Streptococcus pneumoniae(S.pneumonia)R6は、参照株であり、Burkholderia cepacia、Enterococcus faecalis、Escherichia coli(NDM−1)は、香港のクイ−ン・メアリ−病院の多剤耐性臨床分離株であり、Escherichia coli(IMP)は、実験室株である。全ての細菌は、37℃における、対応する増殖培地のブレインハ−トインフュ−ジョン(BHI)ブロス(OXOID)、ミュ−ラ−ヒントン(MH)ブロス(BD)、又はカチオン調整ミュ−ラ−ヒントン(CAMH)ブロス(BD)中の培養である。
MRSA Mu3に対する3種の抗生物質(ゲンタマイシン、セフトリアキソン、及びレボフロキサシン)のMIC値の予備試験を、マイクロブロス希釈法に従って行った。これは、相乗的活性を有するか又は抗生物質の抗菌効果を増強することができる化合物のヒット同定のためにHTSに使用される適切な量の抗生物質についての基準を確立するために行われた。MRSA Mu3に対するゲンタマイシンのMIC値は1000μg/mLであると決定された。抗生物質の調整されたサブMIC濃度をスクリ−ニングに用いた;すなわち、156.25μg/mLの最終濃度のゲンタマイシンを個々のスクリ−ニング実験に用いた。
以前、本出願人は、ハイスル−プットスクリ−ニングプラットフォ−ムを介して、インフルエンザA核タンパク質を標的とする小分子核種を首尾よく分離した(Kao et al.,Nature biotechnology,28(6):600−605(2010))。構造的に多様な小分子化合物の同じライブラリをスクリ−ニングした。バックグラウンドスクリ−ニング(抗生物質を含まないBHI培地によるスクリ−ニング)を最終濃度20μg/mLで実施することにより、直接細菌阻害を有する小分子化合物をスクリ−ニングから除外した。サブMIC抗生物質の存在下でのスクリ−ニングは、抗生物質と組み合わせて潜在的な細菌増殖阻害効果を有する小分子の同定を可能にする。抗生物質とのコンビナトリアル効果を示す化合物の上位10%をさらなる研究のために選択した。二重濃度二次スクリ−ニングを行った;化合物を100μg/mL及び10μg/mLの最終濃度で添加した。この方法は、一次スクリ−ニングからの偽陽性を減らし、成功の再現性を強化することによってスクリ−ニング結果の精度を高めた。
Claims (28)
- 対象における微生物感染症を治療するための組成物であって、薬学的に許容される担体と、式Iで表される有効量の化合物とを含み、
Zは、O、S、CR11R12、又はNR13であり;
R1、R2、R9、R10、R11、R12、R13、R14、及びR15は、独立して、空位、水素、−C(O)R18、−C(W)NR19R20、又は、置換若しくは無置換のアルキル、アルケニル、アルキニル、アルコキシ、シクロアルキル、ヘテロサイクリル、シクロアルケニル、ヘテロシクロアルケニル、アリ−ル、ヘテロアリ−ル、アロキシ、アリ−ルアルキル、ヘテロアルキル、アルキルアリ−ル、ハロゲン、アルキルヘテロアリ−ル、−NR16R17であり;R16及びR17は、独立して、水素、置換若しくは無置換のアルキル、アルケニル、アルキニル、シクロアルキル、ヘテロサイクリル、シクロアルケニル、ヘテロシクロアルケニル、アリ−ル、ヘテロアリ−ル、アリ−ルアルキル、ヘテロアルキル、アルキルアリ−ル、又はアルキルヘテロアリ−ルであり;
R18は、水素、ヒドロキシル、又は、置換若しくは無置換のアルキル、アルケニル、アルキニル、シクロアルキル、アルコキシ、ヘテロサイクリル、シクロアルケニル、ヘテロシクロアルケニル、アリ−ル、アロキシ、ヘテロアリ−ル、アリ−ルアルキル、ヘテロアルキル、アルキルアリ−ル、又はアルキルヘテロアリ−ルであり;
Wは、O、S、又はNR21であり;
R19、R20、及びR21は、独立して、水素、置換若しくは無置換アルキル、アルケニル、アルキニル、シクロアルキル、ヘテロサイクリル、シクロアルケニル、ヘテロシクロアルケニル、アリ−ル、ヘテロアリ−ル、アリ−ルアルキル、ヘテロアルキル、アルキルアリ−ル、又はアルキルヘテロアリ−ルであり;
Aは、二重結合又は単結合であり;
R15は、Aが二重結合である場合には存在せず、
前記化合物の有効量は、微生物中のジヒドロ葉酸レダクタ−ゼを阻害するのに有効である、組成物。 - 前記化合物は、
式II中、
R1は、−O−R4、−NR5R8、又は−CH2−R5であり;
R2は、ハロゲン、空位、−O−CH3、又は−O−CH2−CH3であり;
R9は、−COOH、−CH2−COOH、−CH2−O−CH3、又は−CH2−CH2−O−CH3であり;
R4は、−CH2−R5又は−CO−R5であり;R5は、
R6はハロゲン又は空位であり;
R7はハロゲン又は空位である、
請求項1に記載の組成物。 - 請求項2に記載の組成物であって、R1は2、3、4、5及び6位からなる群から選択される位置にあり;
任意に、R6は4位にあり;
任意に、R7は2又は6位にあり;
任意に、R2は、3、4又は5位にある、組成物。 - 請求項2に記載の組成物であって、前記化合物は式IIA
式中、R1は、−O−R4、−NR5R8、又は−CH2−R5であり;
R2は、ハロゲン、空位、−O−CH3、又は−O−CH2−CH3であり;
R3は、−COOH又は−CH2−COOHであり;
R4は、−CH2−R5又は−CO−R5であり;
R5は、
R6はハロゲン又は空位であり;
R7はハロゲン又は空位である、組成物。 - 請求項4に記載の組成物であって、R1は2、3、4、5及び6位からなる群から選択される位置にあり;
任意に、R6は4位にあり;
任意に、R7は2位又は6位にあり;
任意に、R2は、3、4又は5位にある、組成物。 - 前記化合物が、化合物2−4、6−7、10、13、15、17−20、22、24−25、27−31、34−37、42、44、48−50、52−53、56、60、62−63、69、80−82及び87からなる群より選択される、請求項1乃至5の何れか1項に記載の組成物。
- 治療有効量の抗生物質を更に含む、請求項1乃至6の何れか1項に記載の組成物。
- 前記抗生物質が、ゲンタマイシン、アミカシン、カナマイシン、ネオマイシン、スペクチノマイシン、ネアミン、及びこれらの組み合わせからなる群より選択される、請求項7に記載の組成物。
- 前記抗生物質の治療有効量は、前記組成物の非存在下で対象に投与された場合の抗生物質の治療上有効量又は治療上最適量未満である、請求項7又は8に記載の組成物。
- 対象において微生物感染症を治療する方法であって、前記方法は、請求項1乃至9の何れか1項に記載の組成物を投与することを含み、前記微生物感染症は1つ又は複数の微生物によって引き起こされ、前記組成物は感染を引き起こす少なくとも1つの微生物中のジヒドロ葉酸レダクタ−ゼを抑制するために有効である、方法。
- 感染を引き起こす前記微生物の少なくとも1つが、メチシリン感受性Staphyloccous aureus、Pseudomonas aeruginosa、Listeria monocytogenes、Burkholderia cepacia、Escherichia coli、Enterococcus faecalis、Streptococcus pneumoniae、又はこれらの組合せからなる群より選択されるバクテリアである、請求項10に記載の方法。
- 前記組成物が非経口的又は経口的に投与される、請求項10又は11に記載の方法。
- 感染を引き起こす前記微生物の少なくとも1つが、Streptococcus pneumoniae、Campylobacter、Neisseria gonorrhoeae、Salmonella(薬物耐性非腸チフスSalmonella及び薬物耐性Salmonella血清型チフスを含む)、Shigella、バンコマイシン耐性Enterococcus(VRE)、バンコマイシン耐性Staphylococcus aureus(VRSA)、エリスロマイシン耐性A群Streptococcus、クリンダマイシン耐性B群Streptococcus、カルバペネム耐性Enterobacteriaceae(CRE)、薬剤耐性結核、拡張型Enterobacteriaceae(ESBL)、多剤耐性Acinetobacter(MRABを含む)、Clostridium difficile、腸管病原性E.coli(EPEC)、Pseudomonas aeruginosa、H.pylori、Streptococcus anginosus、及び、尿路病原性E.coli(UPEC)からなる群より選択される抗生物質耐性微生物である、請求項10乃至12の何れか1項に記載の方法。
- 感染を引き起こす前記微生物が、メチシリン耐性Staphylococcus aureus(MRSA)である、請求項13に記載の方法。
- 感染を引き起こす前記微生物が、Listeria monocytogenes、Pseudomonas aeruginosa、Burkholderia cepacia、Enterococcus faecalis、及びStreptococcus pneumoniaeの多剤耐性株である、請求項10又は11に記載の方法。
- 前記感染が、膿痂疹、吹出物、膿瘍、毛包炎、蜂巣炎、壊死性筋膜炎、化膿性筋炎、外科的/外傷性創傷感染症、感染潰瘍及び火傷、骨髄炎、器材関連骨関節感染症、膿痂疹、二次感染皮膚病変、髄膜炎、脳膿瘍、硬膜下膿瘍、並びに脊髄硬膜外膿瘍からなる群より選択される、請求項10乃至15の何れか1項に記載の方法。
- 前記感染が、尿路感染症である、請求項10乃至16の何れか1項に記載の方法。
- 前記対象が、入院しているか免疫不全である、請求項10乃至17の何れか1項に記載の方法。
- 必要な表面を消毒する方法であって、請求項1乃至9の何れか1項に記載の化合物又は組成物を前記表面と接触させることを含んだ方法。
- 前記化合物が、スプレ−、エアロゾル、又はフォ−ムの形態で前記表面に適用される、請求項19に記載の方法。
- 前記化合物が、消毒されるべき表面を拭くのに適した布に吸収される、請求項20に記載の方法。
- 前記表面が、手術器具、心臓及び尿カテ−テル、インプラント、並びに滅菌体腔で使用される超音波プロ−ブからなる群より選択される器具の表面である、請求項19乃至21の何れか1項に記載の方法。
- 前記器具が、内視鏡、喉頭鏡ブレ−ド、食道圧測定プロ−ブ、膀胱鏡、肛門直腸マノメトリカテ−テル、ダイアフラムフィッティングリング、胃鏡、十二指腸鏡、S状結腸鏡、直腸鏡、結腸鏡、気管支鏡、及び喉頭鏡からなる群より選択される、請求項19乃至22の何れか1項に記載の方法。
- 抗生物質の有効性を増加させる方法であって、前記抗生物質と、前記抗生物質の有効性を増加させるのに有効な量の請求項1乃至9の何れか1項に記載の化合物又は組成物とを共投与することを含んだ方法。
- 前記化合物又は組成物が、前記抗生物質と別々に、同時に、又は逐次的に投与される、請求項25に記載の方法。
- 前記抗生物質の効力が、前記抗生物質単独に応答するin vitroアッセイにおける微生物の成長の抑制として測定した場合と比較して、前記抗生物質と前記化合物又は組成物との組み合わせに対する前記微生物の成長の抑制が少なくとも2倍に増加する、請求項26に記載の方法。
- 対象における細菌の毒性を低減させる方法であって、前記細菌は、メシチリン耐性Staphyloccous aureus、Pseudomonas aeruginosa、Listeria monocytogenes、Burkholderia cepacia、Escherichia coli、Enterococcus faecalis、Streptococcus pneumoniae、又はこれらの組合せからなる群より選択され、前記方法は、有効量の請求項1乃至9の何れか1項に記載の化合物又は組成物を前記対象に投与することを含んだ方法。
- 前記化合物が、化合物3、48、49、及び87からなる群から選択される、請求項27に記載の方法。
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