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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    • A61K9/00Medicinal preparations characterised by special physical form
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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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)

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

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

Country Status (20)

Country Link
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) ES8307845A1 (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)
NZ (1) NZ199732A (ja)
PT (1) PT74434B (ja)
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ZA82565B (en) 1982-10-27
HU199695B (en) 1990-03-28
IE820165L (en) 1982-08-16
DK59182A (da) 1982-08-17
NO820433L (no) 1982-08-17
AU2840789A (en) 1989-05-04
YU31582A (en) 1985-04-30
GR76791B (ja) 1984-09-04
ES509647A0 (es) 1983-08-01
JPH05271051A (ja) 1993-10-19
MY101545A (en) 1991-12-17
CA1169090A (en) 1984-06-12
NZ199732A (en) 1985-08-30
AU6498886A (en) 1987-02-19
YU44066B (en) 1990-02-28
AU7998682A (en) 1982-08-26
US4767628B1 (ja) 1990-07-17
DE3273501D1 (en) 1986-11-06
EP0058481A1 (en) 1982-08-25
PT74434A (en) 1982-03-01
EP0058481B1 (en) 1986-10-01
IE52535B1 (en) 1987-12-09
HU186904B (en) 1985-10-28
FI80594B (fi) 1990-03-30
JPH0774143B2 (ja) 1995-08-09
ES8307845A1 (es) 1983-08-01
JPH0157098B2 (ja) 1989-12-04
US4767628A (en) 1988-08-30
ATE22535T1 (de) 1986-10-15
NO162103B (no) 1989-07-31
AU582920B2 (en) 1989-04-13
HK107890A (en) 1990-12-28
NO162103C (no) 1992-03-04
EP0058481B2 (en) 2003-05-21
US5004602A (en) 1991-04-02
FI820467L (fi) 1982-08-17
JPH0686390B2 (ja) 1994-11-02
AU602623B2 (en) 1990-10-18
JPS57150609A (en) 1982-09-17
JPH031330B2 (ja) 1991-01-10
PT74434B (en) 1983-07-14

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