JPH08502266A - O−アルキル化ラパマイシン誘導体および、特に免疫抑制剤としてのその使用 - Google Patents
O−アルキル化ラパマイシン誘導体および、特に免疫抑制剤としてのその使用Info
- Publication number
- JPH08502266A JPH08502266A JP6509552A JP50955294A JPH08502266A JP H08502266 A JPH08502266 A JP H08502266A JP 6509552 A JP6509552 A JP 6509552A JP 50955294 A JP50955294 A JP 50955294A JP H08502266 A JPH08502266 A JP H08502266A
- Authority
- JP
- Japan
- Prior art keywords
- rapamycin
- ethyl
- och
- relative
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/18—Bridged systems
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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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Transplantation (AREA)
- Epidemiology (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Dental Preparations (AREA)
- Steroid Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.式I: 〔式中、Xは(H,H)またはO; Yは(H,OH)またはO; R1およびR2は、それぞれ独立してH、アルキル、チオアルキル、アリールアル キル、ヒドロキシアルキル、ジヒドロキシアルキル、ヒドロキシアルキルアリー ルアルキル、ジヒドロキシアルキルアリールアルキル、アルコキシアルキル、ア シルオキシアルキル、アミノアルキル、アルキルアミノアルキル、アルコキシカ ルボニルアミノアルキル、アシルアミノアルキル、アリールスルホンアミドアル キル、アリル、ジヒドロキシアルキルアリル、ジオキソラニルアリル、カルボア ルコキシアルキルおよび(R3)3Si(式中、R3はそれぞれ独立してH、メチ ル、エチル、イソプロピル、t−ブチルおよびフェニルから選択される)からな る群から選択されるものである;ここで、“アルコ(alk-)”または“アルキル (alkyl)”の語は、直鎖または分枝鎖C1-6アルキル、好ましくはC1-3アルキ ルを意味し、 その炭素鎖は所望によりエーテル(−O−)架橋により中断されていてもよい; および R4はメチルまたはR4とR1が一緒になってC2-6アルキレンを形成する; 但し、R1およびR2は両方ともにHではない;および R1がカルボアルコキシアルキルまたは(R3)3Siである場合、XおよびYは 両方ともにOではない。〕 で示される構造式を有する化合物。 2. 1.40−O−ベンジル−ラパマイシン 2.40−O−(4’−ヒドロキシメチル)ベンジル−ラパマイシン 3.40−O−[4’−(1,2−ジヒドロキシエチル)]ベンジル−ラパマイ シン 4.40−O−アリル−ラパマイシン 5.40−O−[3’−(2,2−ジメチル−1,3−ジオキソラン−4(S) −イル)−プロプ−2’−エン−1’−イル]−ラパマイシン 6.(2’E,4’S)−40−O−(4’,5’−ジヒドロキシペント−2’ −エン−1’−イル)−ラパマイシン 7.40−O−(2−ヒドロキシ)エトキシカルボニルメチル−ラパマイシン 8.40−O−(2−ヒドロキシ)エチル−ラパマイシン 9.40−O−(3−ヒドロキシ)プロピル−ラパマイシン 10.40−O−(6−ヒドロキシ)ヘキシル−ラパマイシン 11.40−O−[2−(2−ヒドロキシ)エトキシ]エチル−ラパマイシン 12.40−O−[(3S)−2,2−ジメチルジオキソラン−3−イル]メチル −ラパマイシン 13.40−O−[(2S)−2,3−ジヒドロキシプロプ−1−イル]−ラパマ イシン 14.40−O−(2−アセトキシ)エチル−ラパマイシン 15.40−O−(2−ニコチノイルオキシ)エチル−ラパマイシン 16.40−O−[2−(N−モルホリノ)アセトキシ]エチル−ラパマイシン 17.40−O−(2−N−イミダゾリルアセトキシ)エチル−ラパマイシン 18.40−O−[2−(N−メチル−N’−ピペラジニル)アセトキシ]エチル −ラパマイシン 19.39−O−デスメチル−39,40−O,O−エチレン−ラパマイシン 20.(26R)−26−ジヒドロ−40−O−(2−ヒドロキシ)エチル−ラパ マイシン 21.28−O−メチル−ラパマイシン 22.40−O−(2−アミノエチル)−ラパマイシン 23.40−O−(2−アセトアミノエチル)−ラパマイシン 24.40−O−(2−ニコチンアミドエチル)−ラパマイシン 25.40−O−(2−(N−メチル−イミダゾ−2’−イルカルボエトキシアミ ド)エチル)−ラパマイシン 26.40−O−(2−エトキシカルボニルアミノエチル)−ラパマイシン 27.40−O−(2−トリスルホンアミドエチル)−ラパマイシン 28.40−O−[2−(4’,5’−ジカルボエトキシ−1’,2’,3’−ト リアゾル−1’−イル)−エチル]−ラパマイシン からなる群から選択される、請求項1記載の化合物。 3.XおよびYが両方O、R2はH、R4はメチルおよびR1はH以外である、請 求項1記載の化合物。 4.40−O−(2−ヒドロキシ)エチル−ラパマイシン。 5.(i)ラパマイシン、デオキシラパマイシンまたはジヒドロラパマイシン( 所望によりO−保護形)を、遊離基に結合した有機ラジカルと、好適な酸性また は中性条件下で反応させ、および(ii)所望により生産物を還元することにより 得られ、または得られ得る、請求項1から4のいずれかに記載の化合物。 6.医薬として使用される、請求項1から5のいずれかに記載の化合物。 7.請求項1から5のいずれかに記載の化合物と医薬的に許容可能な希釈剤また は担体を含む、医薬組成物。 8.以下の状態: (i)自己免疫疾患、 (ii)同種移植片拒絶反応、 (iii)移植片対宿主疾病、 (iv)喘息、 (v)多剤耐性、 (vi)癌または過増殖性疾患、または (vii)真菌感染、 (viii)炎症、 (ix)MipまたはMip様因子を有する病原菌による感染、または (x)マクロフィリン結合免疫抑制剤の過剰投与 の処置または予防のための医薬を製造するための、請求項1から5のいずれかに 記載の化合物の使用。 9.本明細書に実質的に記載の新規生産物、方法および実用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9221220.8 | 1992-10-09 | ||
GB929221220A GB9221220D0 (en) | 1992-10-09 | 1992-10-09 | Organic componds |
PCT/EP1993/002604 WO1994009010A1 (en) | 1992-10-09 | 1993-09-24 | O-alkylated rapamycin derivatives and their use, particularly as immunosuppressants |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP30835598A Division JP3568800B2 (ja) | 1992-10-09 | 1998-10-29 | O−アルキル化ラパマイシン誘導体および、特に免疫抑制剤としてのその使用 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH08502266A true JPH08502266A (ja) | 1996-03-12 |
JP3117462B2 JP3117462B2 (ja) | 2000-12-11 |
Family
ID=10723188
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP06509552A Expired - Lifetime JP3117462B2 (ja) | 1992-10-09 | 1993-09-24 | O−アルキル化ラパマイシン誘導体および、特に免疫抑制剤としてのその使用 |
JP30835598A Expired - Lifetime JP3568800B2 (ja) | 1992-10-09 | 1998-10-29 | O−アルキル化ラパマイシン誘導体および、特に免疫抑制剤としてのその使用 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP30835598A Expired - Lifetime JP3568800B2 (ja) | 1992-10-09 | 1998-10-29 | O−アルキル化ラパマイシン誘導体および、特に免疫抑制剤としてのその使用 |
Country Status (28)
Country | Link |
---|---|
US (2) | US5665772A (ja) |
EP (3) | EP0867438B1 (ja) |
JP (2) | JP3117462B2 (ja) |
KR (2) | KR100308598B1 (ja) |
AT (2) | ATE272063T1 (ja) |
AU (1) | AU676198B2 (ja) |
BR (1) | BR1100353A (ja) |
CA (2) | CA2145383C (ja) |
CY (2) | CY2125B1 (ja) |
CZ (1) | CZ283333B6 (ja) |
DE (3) | DE122004000033I2 (ja) |
DK (2) | DK0663916T3 (ja) |
ES (2) | ES2124793T3 (ja) |
FI (2) | FI109540B (ja) |
FR (1) | FR04C0012I2 (ja) |
GB (1) | GB9221220D0 (ja) |
GE (1) | GEP20002331B (ja) |
HU (1) | HU224074B1 (ja) |
LU (1) | LU91104I2 (ja) |
NL (1) | NL300154I2 (ja) |
NO (3) | NO307053B1 (ja) |
NZ (1) | NZ256026A (ja) |
PL (1) | PL176174B1 (ja) |
PT (1) | PT867438E (ja) |
RO (1) | RO114451B1 (ja) |
RU (1) | RU2143434C1 (ja) |
SK (2) | SK286054B6 (ja) |
WO (1) | WO1994009010A1 (ja) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005200429A (ja) * | 1998-12-07 | 2005-07-28 | Novartis Ag | マクロライドの安定化 |
JP2006515017A (ja) * | 2003-03-17 | 2006-05-18 | ノバルティス アクチエンゲゼルシャフト | 炎症性および免疫介在疾患の処置のための、ラパマイシンまたはその誘導体とピメクロリムスの組み合わせを含む、医薬組成物 |
JP2007512381A (ja) * | 2003-12-01 | 2007-05-17 | ノバルティス アクチエンゲゼルシャフト | 医薬的組み合わせ |
JP2007231017A (ja) * | 2006-02-28 | 2007-09-13 | Cordis Corp | 抗酸化部分を含有するラパマイシン類似体 |
JP2007262057A (ja) * | 2006-02-28 | 2007-10-11 | Cordis Corp | ラパマイシンアルキルエーテル類似体の異性体および42−エピマー、同物質の製造法および使用法 |
JP2008106074A (ja) * | 2000-01-14 | 2008-05-08 | Univ Pennsylvania | リンパ増殖症候群の緩和および阻害のためのo−メチル化ラパマイシン誘導体 |
JP2008532991A (ja) * | 2005-03-11 | 2008-08-21 | バイオティカ テクノロジー リミテッド | ラパマイシンの39−デスメトキシ誘導体 |
JP2009513522A (ja) * | 2003-07-08 | 2009-04-02 | ノバルティス アクチエンゲゼルシャフト | 骨減少の処置のための、ラパマイシンおよびラパマイシン誘導体の使用 |
JP2009102349A (ja) * | 1996-03-27 | 2009-05-14 | Novartis Ag | 血管疾病および異種移植におけるラパマイシン誘導体の使用 |
JP2009525294A (ja) * | 2006-02-02 | 2009-07-09 | ノバルティス アクチエンゲゼルシャフト | 結節性硬化症処置 |
JP2009537504A (ja) * | 2006-05-19 | 2009-10-29 | バイオティカ テクノロジー リミテッド | 癌および他の疾患の治療のための39−デスメトキシ−39−メチルラパマイシン誘導体 |
JP4716280B2 (ja) * | 2004-03-01 | 2011-07-06 | テルモ株式会社 | O−アルキル化ラパマイシン誘導体の製造法 |
JP2011525890A (ja) * | 2008-03-11 | 2011-09-29 | エリクサー・メディカル・コーポレイション | 大環状ラクトン化合物およびそれらの使用方法 |
JP2014177469A (ja) * | 2001-02-19 | 2014-09-25 | Novartis Ag | 癌の処置 |
JP2016523246A (ja) * | 2013-06-20 | 2016-08-08 | ノバルティス アーゲー | アルキルフルオロアルキルスルホネートによるアルキル化 |
JP2022137237A (ja) * | 2019-01-22 | 2022-09-21 | エオビアン ファーマシューティカルズ, インコーポレイテッド | Mtorcモジュレーターおよびその使用 |
Families Citing this family (404)
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USRE40596E1 (en) * | 1993-04-08 | 2008-12-02 | Novartis Ag | Rapamycin assay |
GB9307491D0 (en) * | 1993-04-08 | 1993-06-02 | Sandoz Ltd | Organic compounds |
US7279561B1 (en) | 1993-04-23 | 2007-10-09 | Wyeth | Anti-rapamycin monoclonal antibodies |
DE69430060T2 (de) | 1993-04-23 | 2002-11-07 | Abbott Lab | Antikörper von rapamycinen mit offenem ring |
USRE37421E1 (en) | 1993-07-16 | 2001-10-23 | Smithkline Beecham Corporation | Rapamycin derivatives |
ES2308955T5 (es) * | 1993-09-28 | 2012-04-03 | R.P. Scherer Gmbh | Fabricación de cápsulas de gelatina blanda |
EP0729471A1 (en) * | 1993-11-19 | 1996-09-04 | Abbott Laboratories | Semisynthetic analogs of rapamycin (macrolides) being immunomodulators |
US5527907A (en) * | 1993-11-19 | 1996-06-18 | Abbott Laboratories | Macrolide immunomodulators |
SK78196A3 (en) * | 1993-12-17 | 1997-02-05 | Sandoz Ag | Rapamycin demethoxy-derivatives, preparation method thereof and pharmaceutical agent containing them |
GB9405350D0 (en) * | 1994-03-18 | 1994-05-04 | Sandoz Ltd | Organic compounds |
EP0786986B1 (en) * | 1994-10-26 | 2002-03-20 | Novartis AG | Use of an unsaturated fatty alcohol |
US7205279B2 (en) * | 1995-10-25 | 2007-04-17 | Novartis Ag | Pharmaceutical compositions |
PE52896A1 (es) | 1994-10-26 | 1996-12-12 | Novartis Ag | Composicion farmaceutica |
US5561138A (en) * | 1994-12-13 | 1996-10-01 | American Home Products Corporation | Method of treating anemia |
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IL147803A0 (en) | 1999-08-24 | 2002-08-14 | Ariad Gene Therapeutics Inc | 28-epirapalogs |
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