JPS6264824A - 乳酸単位とグリコ−ル酸単位との不均一なコ−ポリマ−及びその製造法 - Google Patents

乳酸単位とグリコ−ル酸単位との不均一なコ−ポリマ−及びその製造法

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JPS6264824A
JPS6264824A JP61162196A JP16219686A JPS6264824A JP S6264824 A JPS6264824 A JP S6264824A JP 61162196 A JP61162196 A JP 61162196A JP 16219686 A JP16219686 A JP 16219686A JP S6264824 A JPS6264824 A JP S6264824A
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lactic acid
glycolic acid
acid unit
polylactide
copolymer
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JPH031330B2 (ja
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フランシス・ゴウランド・ハツチンソン
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Imperial Chemical Industries Ltd
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Abstract

(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。

Description

【発明の詳細な説明】 本発明は、乳酸単位とグリコール酸単位との不均一なコ
ーポリマー及びその製造法に関する。
単一投与による延長した期間にわたる一定の薬剤の連続
的放出は臨床上では実際に重要な利点を有し、既に組成
物は開発されて、経口投与後〔参照：例えばレミントン
ズ・ファーマンイテイカルφサイエンスズ（Ｒｅｍｉｎ
ｇｔｏｎ’ｓ　Ｐｈａ−ｒｍａｃｅｕｔｉｃａｌ　５ｃ
ｉｅｎｃｅｓＪ、　７ツク（ＭａＣｋＪ出版社版、米国
、ペンシルノ々ニア、イートン在、第１５版、１９７５
年、第１６１８〜１６３１頁〕、非経口投与後（同書、
第１６３１〜１６４３頁）及び局所的投与後（参照：例
えば英国特許第１３５１４０９号明細書）に、多くの臨
床上有用な薬剤の延長した放出が得られた。非経口投与
の適当な方法は皮下注射又は固体、例えば薬剤を含有す
るペレット又はフィルムの挿入であシ、かかる多くの挿
入することのできる調合物が記載されている。実際に多
くの薬剤に対して延長した薬剤の放出を得る適当な挿す
ることのできる調合物は、薬剤を生減成し得るポリマー
に装入する、か又は薬剤をかかるポリマーマトリックス
に分散させて得ることができ、それ故薬剤はポリマーマ
トリックスの減成が進行するにつれて放出これることは
公知である。
持Ｍした放出の調合物に使用するために適当な生減成す
るポリマーは公知であり、生理学的水性環境に入れると
加水分解によって徐々に減成するポリエステルを包含す
る。使用した特別のポリエステルはヒドロキシカルｌン
酸から誘導されたポリエステルであり、多くの文献はα
−ヒドロキシカルボン酸、殊にセラミ形及び光学活性の
乳酸及びグリコール酸から誘導きれたポリマー及びその
コーポリマーに関する−例えば米国特許第３７７３９１
９号及び第３８８７６９９号明細書；ジャツカニラ（Ｊ
ａｃｋａｎｉｃｚ　）その他、コントラセプシ９　：ｙ
　（ｃｏｎｔｒａｃｅｐｔ　ｉｏｎ　）、１９７３年、
第８巻、第２２７〜２３４頁；アンダーソン（Ａｎｄｅ
ｒｓｏｎ　）その他、同書、１９７６年、第１１巻、第
３７５〜３８４頁；ワイズ（ＷｊＳｅＪその他、サイ７
・サイエンセ！（Ｌｉｆｅ　５ｃｉｅｎ−ＣｅＳ）、１
９７６年、第１９巻、第８６７〜８７４頁；ラードラン
ド（Ｗｏｏｄ　Ｉ　ａｎｄ　）その他、ジャーナル・オ
ブ参メディカルｅケミストリー（Ｊｏｕ−ｒｎａｌ　ｏ
ｆ　Ｍｅｄｉｃｉｎａｌ　Ｃｈｅｍｉｓｔｒｙ　八１９
７３年、第１６巻、第８９７〜９０１頁；ヨーレス（Ｙ
ｏｌ　ｌｅｓ　）その他、ブレチン舎オブーザ・パレ７
テラル・ドラグ・アソシエーション（Ｂｕｌｌ−ｅｔｉ
ｎ　ｏｆ　ｔｈｅ　Ｐａｒｅｎｔｅｒａｌ　Ｄｒｕｇ　
Ａｓ５ｏｃｉａ−ｔｊＯｎ）、１９７６年、第３０巻、
第３０６〜３１２頁；ワイズ（ＷｉｓｅＪその他、ジャ
ーナル・オブ・７アマシー・アンド・ファマコロシー（
Ｊｏｕｒｎａｌ　ｏｆ　Ｐｈａｒｍａｃｙ　ａｎｄ　Ｐ
ｈａｒｍａｃｏｌｏ−ｇｌ、１９７８年、第３０巻、第
６８６〜６８９頁及び１９７９年、第３１巻、第２０１
〜２０４頁参照。
本発明の目的は、薬剤を調合するのに適当な乳酸単位と
グリコール酸単位とからなる不均一なコーポリマーを得
ることである。
本明細書中で一ポリラクチドｌという用語は通常の意味
で使用され、・乳酸だけのポリマー、ｆｌＪｌグリコー
ル酸とのコーポリマー、か＼るポリマー混合物、か＼る
コーポリマー混合物及びか＼るポリマーとコーポリマー
との混合物を包含し、乳酸はラセミ形か又は光学活性形
である。
ポリラクチド、特に乳酸単位及びグリコール酸単位を有
するコーポリマーに関する公知方法には、低分子量のコ
ーポリマーの製造及びか＼るコーポリマーで大きい多分
散性を得る方法は記載されていない、ポリラクチドの公
知方法の記載では、ポリラクチドは無水条件下で連鎖停
止剤全添加しないその製造のために、一般に約３０００
０〜６００００以上（固有粘度０．５以上）の分子ｉ１
（Ｍｗ＋及び低い多分散性である。乳酸及びグリコール
酸の環状二量体の重合条件下における異なる反応性のた
めに、ポリマーに関して不均一性の大きいコーポリマー
は、２つの環状二量体混合物を連φ０停止剤の存在で開
環重合させて得ることができ、固Ｍ粘度０．５以下を有
するポリラクチドが得られる。グリコール酸の環状二量
体は重合条件下で反応性であり、このようにして重合で
形成する最初のコーポリマー分子はグリコール酸が多い
。従って形成する彼のコーポリマー分子は必然的に乳酸
が多く、所望の大きい不均一性の乳酸とグリコール酸と
のコーポリマーが得られる。
更に、所望の低ＭＷの範囲内のコーポリマーを得るため
には、常用のポリマー技術によって混合環状二量体の開
環共重合を水、乳酸含櫓水又は他の一定の公知連鎖増大
調整剤の存托で行なうことによって重合を調節する。
適当な１会触媒は酸化亜鉛、炭酸亜鉛、塩基性炭酸亜鉛
、ジエチル亜鉛、有機錫化合物、ρりえばオクタン酸第
１錫、トリブチルアルミニウム、チタン、マグネシウム
又はノセリウム化合物又はリサージであり、これらのう
ちオクタン酸第１錫が好ましい。
混合環状二針体の共重合は、他の点で時…１及び温度に
関してはポリマー分野で公知の常法で行なう。
低分子量のポリラクチドは、埋状二１体よりもむしろそ
れ自体ヒドロキシ酸全共重合させても得られる。この方
法では不均一性の小さいポリマーが得られるが、ポリペ
プチドの連続的放出に適当なマトリックスは、この方法
で得られた異なる組成のか＼るポリラクチドを混合する
か、又はこの方法で得られたポリラクチドを、環状二量
体の開埋東合によって得られた１種以上のポリマクチＦ
と混合して得ることができる。
前述の乳酸／グリコール酸コーポリマーの成るものは新
規であり、本発明の特徴をなす。
このようにして本発明の特徴によって、乳酸単位２５〜
１００モルチ及びグリコール酸単位θ〜７５モルチを含
有し、ベンゼンに可溶で固有粘度（ベンゼンにとかした
ｉＦ／１００＋＋＋ｊｌ液）０．５以下を有するか又は
ベンゼンに不溶で固有粘度（クロロホルム又はジオキサ
ンにとかした１ｒ／１ｏｏｉ＠液Ｊ４以下を有する不均
一なポリラクチドが得られる。Ｓ不均一なポリラクチド
〃とは、前述のようにグリコリドの多い及びラクチドの
多い分子に関して高度の４く均−性又は大きい多分散性
を有するポリラクチドか又は前述のようにラクチド／グ
リコリド含量及び／又はＭｗの異なる種々のポリラクチ
ド２種又は数種の配合物である。
この童味で個々のコーポリマーが不均一であるかどうか
は、例えばジューテロ化ジメチルスルホキシド中でコー
ポリマーの２５　ＭＨｚ１６Ｃ核磁、気共鳴スペクトル
の測定から容易に測定することができる。公知方法の乳
酸及びグリコール酸モノマーの共重合で得られる不均一
なコーポリマーでは、グリコール酸単囲のカルボニルカ
ーボンの共鳴（δ＝１．６６．０〜１６６．２）は、こ
の分子、即ちＧＧＧ、ＬＧＧ、ＧＧＬ及びＬＧＬ（Ｇ＝
ニブリコール単位、Ｌ−乳酸単位、星印は考慮中のグリ
コール酸単位を示す）の結果として２つの二重線として
表わｆ＋、る、こわに反して、本発明で使用するイξ均
−人コーポリマーでは、ＬＧＬは生じ々いので、不均一
なコーポリマーのスペクトル中の二重線の１つは一重線
として表われる。実際に不均一なコーポリマーのスペク
トル中では、このグリコール酸単位のカルボニルカーボ
ンは屡々２つの一重線として表われるっこのようにして
、前述のように定義した嘱不均−なコーポリマーｌは、
Ｃｎ、ｍ、ｒ、のグリコール酸のカルボニルカーボンは
１対の二重線とは異なったものとして表われるコーポリ
マーである。
乳酸／クリコール酸コーポリマーの不均一性又は均一性
は、それらの減成試験で証明することもできる。即ち、
コーポリマーをｐＨ７，４の緩衝液に３７℃で入れ、周
期的に取出し、乾燥し、ザンプル金取り、サンプル中の
乳酸対グリコール酸の割合をｎ、ｍ、ｒ、によって測定
し、モ均一なコーポリマーに対しては、Ｌ／Ｇの割合は
グリコール酸が加水分解するのに従って増大する。これ
に対して、均一なコーポリマーに対しては、Ｌ／Ｇの割
合は減成が進行するのに従って一定である。
コーポリマーの乳酸は、好ましくはラセミ（Ｄ、Ｌ＋形
か又は光学活性し形である。
更に本発明の特徴によって、前述のような乳酸及びグリ
コール酸の新規コーポリマーの製造法が得られ、これは
乳酸及びグリコール酸の環状二量体混合物を、場合によ
り連鎖増大調節剤の存在で開環共重合させることからな
る。
適当な連鎖増大調節剤は、例えば水、乳酸、グリコール
酸又は他のヒドロキシ酸、アルコール又はカルゲン酸で
あるっ 次に実施例につき本発明を説明する。
調合剤１ 酸化亜鉛（１６ｆＪｉ、Ｄ、Ｌ−乳酸（８００ｆ’＋に
撹拌機、温度計及び水のコンデンサーに結合した蒸溜頭
を備えた２ｔの三相円形フラスコ中で添加したつ混合物
を攪拌し、約１３５℃に加熱し、この温度で水が溜出し
始めたつ加熱を８時間続け、この時間の間に温度は約１
９０℃に上った。水の蒸溜が止むと、圧力が減じ、蒸溜
を固体がコンデンサー中に集まシ始めるまで続けた。こ
の段階で水のコンデンサー全空気のコンデンサーに代え
、残渣全冷却し、次いで高真空（２〜８ＩＨｔｘ下に蒸
溜し、１３０〜１６０℃の間に溜出するフラクション（
約３００ｆ　Ｊを集め、これはり、Ｌ−ラクチド（３，
６−シメチルー１．４−ジオキサン−２，５−ジオン八
り、Ｌ−乳酸の環状二量体であった。
粗製り、Ｌ−ラクチドを酢酸エチル（約６００ｄＪから
３回結晶させ、再結晶生成物を最後に減圧（Ｚ　ｗＨｇ
　Ｊ下に４５℃で２４〜４８時間乾燥し、この彼に融点
１２４〜１２５℃を有していた。
調合剤２ グリコリド（１，４−ジオキサン−２，５−ジオン）、
グリコール酸の環状二量体を、亀ゾリパレーテイブ、メ
ソーズ昏イン書ポリマー・ケミストリー（Ｐｒｅｐａｒ
ａｔｉｖｅ　Ｍｅｔｈｏｄｓ　　ｉｎＰｏｌｙｍｅｒ　
ｃｈｅｍｉｓｔｒｙ　）　ｌ　［７Ｖ　ンサン（Ｗ。
Ｒ、５ｏｒｅｎｓｏｎ　）及び力ンプペル（Ｔ　、Ｗ、
　Ｃａｍｐ−ｂｅｌｌ）著、第２版、第３６３頁、１９
６８年、イｙｐ−サイエフ　ス（Ｉｎｔｅｒｓｃｉｅｎ
ｃｅ　Ｊ社刊〕に記載の方法で製造した。和製グリコリ
ドを乾燥した酢酸エチルから３回結晶させて精製し、次
いで減圧（２〜８１１ｍＨ２）下に４５℃で２４〜４８
時間乾燥した。融点８２〜８４℃。
例１〜１３ Ｄ、Ｌ−ラクチド及びグリコリドのポリマーを、次のよ
うにして製造した： 純粋の乾燥り、Ｌ−ラクチド（調合剤１３゜純粋の乾燥
グリコリド（調合剤２］（全体で４２１）、市場で得ら
れる水約１２重量％ヲ含有するり、Ｌ−乳酸及びオクタ
ン酸第１錫をヘキサンにとかした８重量係のｍ液１−を
、予め乾燥したガラス管に装入した。ヘキサンを減圧下
に蒸発させ、管を一定に攪拌しながら１６０℃で６時間
力ロ熱した。管を粉末状固体二酸什炭素中で冷却し、ポ
リラクチド全取出し、小片に粉砕し、クロロホルム（４
００ｄＪにとがした。クロロホルム溶液ｋ濾過し、Ｐ液
ケメタノール（２ｔ）中に注いでポリラクチドを沈殿さ
せ、これを戸取し、真空下に４０℃で２４時間、次いで
８０℃で２４時間乾燥した。こうして得られたポリラク
チド全部をクロロホルム及びジオキサンにとかした。次
表のポリラクチド１〜９はベンゼンに溶解したが、ポリ
ラクチド１０〜１３はベンゼンに不浴であった。
次にポリラクチドを、この方法で製造した：選択的にラ
クチド、グリコリド及び乳酸（存在する場合）ｆ１６０
℃で加熱し、次いでオクタン酸第１錫ｏ、ｏ　ｓ　ｙを
添加して重合を開始してもよい。
図１１４ 図］１〜１３の方法を、ポリラクチドをクロロホルムの
代りにジオキサンにとかした点を除いてくり返し、同］
−ポリラクチドが得られたつ１４１１５〜２２ 列１〜１３の方法を、ポリラクチドを沈殿させるために
、ポリラクチドを氷酢酸にとかし、こうして得られた氷
酢酸溶液ケメタノールに滴加した点を除いてくり返し、
ポリラクチドを沖取し、真空下に４０℃で２４時間、次
いで８０℃で２４時間乾燥した。

Claims (1)

  1. 【特許請求の範囲】 １、乳酸単位２５〜１００モル％及びグリコール酸単位
    ０〜７５モル％を有し、ベンゼンに可溶で固有粘度０．
    ５以下（ベンゼンにとかした１ｇ／１００ｍｌ溶液）を
    有するか、又はベンゼンに不溶で固有粘度４以下（クロ
    ロホルム又はジオキサンにとかした１ｇ／１００ｍｌ溶
    液）を有する、乳酸単位とグリコール酸単位との不均一
    なコーポリマー。 ２、乳酸単位２５〜１００モル％及びグリコール酸単位
    ０〜７５モル％を有し、ベンゼンに可溶で固有粘度０．
    ５以下（ベンゼンにとかした１ｇ／１００ｍｌ溶液）を
    有するか、又はベンゼンに不溶で固有粘度４以下（クロ
    ロホルム又はジオキサンにとかした１ｇ／１００ｍｌ溶
    液）を有する乳酸単位とグリコール酸単位との不均一な
    コーポリマーを製造する方法において、乳酸とグリコー
    ル酸との環状二量体混合物を開環共重合させることを特
    徴とする、不均一なコーポリマーの製造法。
JP61162196A 1981-02-16 1986-07-11 乳酸単位とグリコ−ル酸単位との不均一なコ−ポリマ−及びその製造法 Granted JPS6264824A (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8104734 1981-02-16
GB8104734 1981-02-16

Publications (2)

Publication Number Publication Date
JPS6264824A true JPS6264824A (ja) 1987-03-23
JPH031330B2 JPH031330B2 (ja) 1991-01-10

Family

ID=10519727

Family Applications (4)

Application Number Title Priority Date Filing Date
JP57023497A Granted JPS57150609A (en) 1981-02-16 1982-02-16 Pharmaceutical composition, heterogeneous copolymer comprising lactic acid and glycolic acid units and manufacture
JP61162196A Granted JPS6264824A (ja) 1981-02-16 1986-07-11 乳酸単位とグリコ−ル酸単位との不均一なコ−ポリマ−及びその製造法
JP3098686A Expired - Lifetime JPH0686390B2 (ja) 1981-02-16 1991-04-30 薬理学上活性で酸に安定なポリペプチドの製剤
JP3098688A Expired - Lifetime JPH0774143B2 (ja) 1981-02-16 1991-04-30 ポリ（ラクチド−共−グリコリド）ポリマーの製造法

Family Applications Before (1)

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JP57023497A Granted JPS57150609A (en) 1981-02-16 1982-02-16 Pharmaceutical composition, heterogeneous copolymer comprising lactic acid and glycolic acid units and manufacture

Family Applications After (2)

Application Number Title Priority Date Filing Date
JP3098686A Expired - Lifetime JPH0686390B2 (ja) 1981-02-16 1991-04-30 薬理学上活性で酸に安定なポリペプチドの製剤
JP3098688A Expired - Lifetime JPH0774143B2 (ja) 1981-02-16 1991-04-30 ポリ（ラクチド−共−グリコリド）ポリマーの製造法

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US (2) US5004602A (ja)
EP (1) EP0058481B2 (ja)
JP (4) JPS57150609A (ja)
AT (1) ATE22535T1 (ja)
AU (3) AU560829B2 (ja)
CA (1) CA1169090A (ja)
DE (1) DE3273501D1 (ja)
DK (1) DK164845B (ja)
ES (1) ES509647A0 (ja)
FI (1) FI80594B (ja)
GR (1) GR76791B (ja)
HK (1) HK107890A (ja)
HU (2) HU199695B (ja)
IE (1) IE52535B1 (ja)
MY (1) MY101545A (ja)
NO (1) NO162103C (ja)
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NO162103B (no) 1989-07-31
US4767628A (en) 1988-08-30
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JPS57150609A (en) 1982-09-17
AU7998682A (en) 1982-08-26
NO162103C (no) 1992-03-04
JPH05221871A (ja) 1993-08-31
ZA82565B (en) 1982-10-27
MY101545A (en) 1991-12-17
EP0058481B2 (en) 2003-05-21
JPH05271051A (ja) 1993-10-19
ES8307845A1 (es) 1983-08-01
AU2840789A (en) 1989-05-04
ATE22535T1 (de) 1986-10-15
JPH0774143B2 (ja) 1995-08-09
HU199695B (en) 1990-03-28
CA1169090A (en) 1984-06-12
FI80594B (fi) 1990-03-30
EP0058481A1 (en) 1982-08-25
PT74434B (en) 1983-07-14
IE820165L (en) 1982-08-16
DE3273501D1 (en) 1986-11-06
JPH0686390B2 (ja) 1994-11-02
JPH0157098B2 (ja) 1989-12-04
US5004602A (en) 1991-04-02
PT74434A (en) 1982-03-01
AU582920B2 (en) 1989-04-13
AU560829B2 (en) 1987-04-16
AU6498886A (en) 1987-02-19
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FI820467L (fi) 1982-08-17
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DK59182A (da) 1982-08-17
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JPH031330B2 (ja) 1991-01-10
US4767628B1 (ja) 1990-07-17
ES509647A0 (es) 1983-08-01
GR76791B (ja) 1984-09-04
HU186904B (en) 1985-10-28
DK164845B (da) 1992-08-31
NO820433L (no) 1982-08-17

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