JP5489333B2 - 脂肪酸合成阻害剤を用いた治療の方法 - Google Patents
脂肪酸合成阻害剤を用いた治療の方法 Download PDFInfo
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- JP5489333B2 JP5489333B2 JP2009529213A JP2009529213A JP5489333B2 JP 5489333 B2 JP5489333 B2 JP 5489333B2 JP 2009529213 A JP2009529213 A JP 2009529213A JP 2009529213 A JP2009529213 A JP 2009529213A JP 5489333 B2 JP5489333 B2 JP 5489333B2
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Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- 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
- A61P31/10—Antimycotics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Description
本発明は、式I及びII
に示されている天然産物又は医薬として許容されるこれらの塩の、脂肪酸合成阻害剤としての使用を記載する。
式I及びIIに示されている天然産物は、肥満、癌、糖尿病、真菌感染、マイコバクテリウム・チュバキュロシス(Mycobacterium tuberculosis)感染、マラリア感染及び他のアピコンプレクサ原虫疾患を治療し、これらの症候を軽減し、これらを予防し、及び/又はこれらに罹患する確率を低減するために、これを必要としている患者に投与することができる。
びレプチンとは反対の様式で制御することを報告した。Makimura他は、セルレニンの反復注射が、視床下部のニューロペプチド遺伝子発現を調節せずに、マウスの体重を減少させ、代謝速度を増加させることも報告した。これらの相違は、生理的な状況及びモデルに関連している可能性がある。
(b)ビオタ、LP−100、ノバラピッド、インシュリンデテミル、インシュリンリスプロ、インシュリングラルジン、インシュリン亜鉛懸濁物(レンテ及びウルトラレンテ)、Lys−Proインシュリン、GLP−1(73−7)(インシュリントロピン);及びGLP−1(7−36)−NH2)などのインシュリン又はインシュリン模倣物質;
(c)アセトヘキサミド;クロルプロマミド;ダイアビネーゼ;グリベンクラミド;グリピジド;グリブリド;グリメピリド;グリクラジド;グリペンチド;グリキドン;グリソラミド;トラザミド及びトルブタミドなどのスルホニル尿素;
(d)アカルボース、アジポシン;カミグリボース;エミグリタート;ミグリトール;ボグリボース;プラジミシン−Q;サルボスタチン;CKD−711;MDL−25,637;MDL−73,945及びMOR14などのα−グルコシダーゼ阻害剤;
(e)(i)HMG−CoA還元酵素阻害剤(アトロバスタチン、イタバスタチン、フルバスタチン、ロバスタチン、プラバスタチン、リバスタチン、ロスバスタチン、シンバスタチン及び他のスタチン)、(ii)コレスチラミン、コレスチポール、架橋されたデキストランのジアルキルアミノアルキル誘導体;Colestid(R);LoCholest(R)などの胆汁酸吸収物質/捕捉剤、(ii)ニコチニルアルコール、ニコチン酸又はその塩、(iii)フェノフィブリン酸誘導体(ゲムフィブロジル、クロフィブラート、フェノフィブラート及びベンザフィブラート)などの増殖因子−活性化因子受容体αアゴニスト、(iv)スタノールエステル、β−シトステロール、チクエシドなどのステロールグリコシドなどのコレステロール吸収の阻害剤、並びにエゼチミブなどのアゼチジノン類、並びにアバシミブ及びメリナミドなどの(アシルCoA:コレステロールアシル転移酵素(ACAT))阻害剤、(v)プロブコールなどの抗酸化剤、(vi)ビタミンE及び(vii)甲状腺ホルモン様物質などのコレステロール降下剤;
(f)ベクロフィブラート、ベンザフィブラート、シプロフィブラート、クロフィブラート、エトフィブラート、フェノフィブラート及びゲムフィブロジル;並びにAtromid(R)、Lopid(R)及びTricor(R)などの他のフィブリン酸誘導体などのPPARαアゴニスト並びにGlaxoによってWO97/36579号に記載されているPPARαアゴニスト;
(g)WO97/28149に開示されているものなどのPPARδアゴニスト;
(h)ムラグリタザール及び米国特許第6,414,002号に開示されている化合物などのPPARα/δアゴニスト;
(i)バレニクリンなどのニコチンアゴニスト若しくは部分的ニコチンアゴニスト又はモノアミンオキシダーゼ阻害剤(MAOI)又は禁煙を補助する上で有効性が示されている別の活性成分、例えば、ブプロピオン、ドキセピン若しくはノルトリプチリンなどの抗うつ剤又はブスピロン若しくはクロニジンなどの抗不安薬などの喫煙剤;並びに
(1)NN703、ヘキサレリン、MK−0677、SM−130686、CP−424,391、L−692,429及びL−163,255など、並びに米国特許第5,536,716号及び米国特許第6,358,951号、米国特許出願第2002/049196号及び米国特許出願第2002/022637号及びPCT出願WO01/56592号及びWO02/32888号に開示されているものなど、成長ホルモン分泌促進物質、成長ホルモン分泌促進物質受容体アゴニスト/アンタゴニスト;(2)タンパク質チロシンホスファターゼー1B(PTP−1B)阻害剤;(3)リモナバント(Sanofi Synthelabo)、AMT−251及びSR−14778及びSR141716A(Sanofi Synthelabo)、SLV−319(Solvay)、BAY65−2520(Bayer)並びに米国特許第5,532,237号、米国特許第4,973,587号、米国特許第5,013,837号、米国特許第5,081,122号、米国特許第5,112,820号、米国特許第5,292,736号、米国特許第5,624,941号、米国特許第6,028,084、PCT出願WO96/33159号、WO98/33765号、WO98/43636号、WO98/43635号、WO01/09120号、WO98/31227号、WO98/41519号、WO98/37061号、WO00/10967号、WO00/10968号、WO97/29079号、WO99/02499号、WO01/58869号、WO01/64632号、WO01/64633号、WO01/64634号、W002/076949号、WO03/007887号、WO04/048317号及びWO05/000809号;並びにEPO出願EP−658546号、EP−656354号、EP−576357号に開示されているものなど、カンナビノイドCB1受容体アンタゴニスト又は逆アゴニストなどカンナビノイド受容体リガンド;(4)フェンフルラミン、デクスフェンフルラミン、フェンテルミン及びシブトラミンなどの抗肥満セトロニン作動性因子;(5)AD9677/TAK677(Dainippon/Takeda)、CL−316,243、SB418790、BRL−37344、L−796568、BMS−196085、BRL−35135A、CGP12177A、BTA−243、Trecadrine、ZenecaD7114、SR59119など、並びに米国特許出願第5,705,515号及び米国特許第5,451,677号並びにPCT特許公開WO94/18161号、WO95/29159号、WO97/46556号、WO98/04526号及びWO98/32753号、WO01/74782号及びWO02/32897号に開示されているものなどのβ3アドレナリン受容体アゴニスト;(6)オリスタット(Xnical(R))、TritonWR1339、RHC80267、リプスタチン、テトラヒドロリプスタチン、ティーサポニン、ジエチルウンベリフェリルリン酸及びPCT出願WO01/77094号に開示されているものなど、膵臓のリパーゼ阻害剤;(7)BIBP3226、J−115814、BIBO3304、LY−357897、CP−671906、GI−264879A並びに米国特許第6,001,836号並びにPCT特許公開WO96/14307号、WO01/23387号、WO99/51600号、WO01/85690号、WO01/85098号、WO01/85173号及びWO01/89528号に開示されているものなどの、ニューロペプチドY1アンタゴニスト;(8)GW−569180A、GW−594884A、GW−587081X、GW−548118X、FR226928、FR240662、FR252384、1229U91、GI−264879A、CGP71683A、LY−377897、PD−160170、SR−120562A、SR−120819A及びJCF−104並びに米国特許第6,057,335号;米国特許第6,043,246号;米国特許第6,140,354号;米国特許第6,166,038号;米国特許第6,180,653号;米国特許第6,191,160号;米国特許第6,313,298号;米国特許第6,335,345号;米国特許第6,337,332号;米国特許第6,326,375号;米国特許第6,329,395号;米国特許第6,340,683号;米国特許第6,388,077号;米国特許第6,462,053号;米国特許第6,649,624号;及び米国特許第6,723,847号(参照により、その全体が本明細書に組み込まれる。);欧州特許EP−01010691号及び欧州特許EP−01044970号;並びにPCT国際特許公報WO97/19682号、WO97/20820号、WO97/20821号、WO97/20822号、WO97/20823号、WO98/24768号;WO98/25907号;WO98/25908号;WO98/27063号、WO98/47505号;WO98/40356号;WO99/15516号;WO99/27965号;WO00/64880号、WO00/68197号、WO00/69849号、WO01/09120号、WO01/14376号;WO01/85714号、WO01/85730号、WO01/07409号、WO01/02379号、WO01/02379号、WO01/23388号、WO01/23389号、WO01/44201号、WO01/62737号、WO01/62738号、WO01/09120号、WO02/22592号、WO0248152号、及びWO02/49648号;WO02/094825号;WO03/014083号;WO03/10191号;WO03/092889号;WO04/002986;及びWO04/031175号などのニューロペプチドY5アンタゴニスト、;(9)WO01/21577号及びWO01/21169号に開示されているものなどの、メラニン凝集ホルモン(MCH)受容体アンタゴニスト;(10)T−226296(Takeda)並びにPCT特許出願WO01/82925号、WO01/87834号、WO02/051809号、WO02/06245号、WO02/076929号、WO02/076947号、WO02/04433号、WO02/51809号、WO02/083134号、WO02/094799号、WO03/004027号並びに日本国特許出願JP13226269号及びJP2004−139909号に開示されているものなどの、メラニン凝集ホルモン1受容体(MCH1R)アンタゴニスト;(11)メラニン凝集ホルモン2受容体(MCH2R)アゴニスト/アンタゴニスト;(12)SB−334867−A並びにPCT特許出願WO01/96302号、WO01/68609号、WO02/51232号及びWO02/51838号に開示されているものなどのオレキシン−1受容体アンタゴニスト;(13)フルオキセチン、パロキセチン及びセルトラリンなどの米国特許第6,365,633号及びPCT特許出願WO01/27060号及びWO01/162341号に開示されているものなどの、セロトニン再取り込み阻害剤;(14)メラノタンII又はWO99/64002号及びWO00/74679号に記載されているものなどのメラノコルチンアゴニスト;(15)CHIR86036(Chiron)、ME−10142及びME−10145(Melacure)、CHJR86036(Chiron);PT−141及びPT−14(Palatin)並びに米国特許第6,410,548号;6,294,534号、米国特許第6,350,760号、米国特許第6,458,790号、米国特許第6,472,398号、米国特許第6,376,509号及び米国特許第6,818,658号、米国特許公報US2002/0137664号;米国特許公報US2003/0236262号;米国特許公報US2004/009751号;米国特許公報US2004/0092501号;及びPCT出願WO99/64002号;WO00/74679号;WO01/70708号;WO01/70337号;WO01/74844号;WO01/91752号;WO01/991752号;WO02/15909号;WO02/059095号;WO02/059107号;WO02/059108号;WO02/059117号;WO02/067869号;WO02/068387号;WO02/068388号;WO02/067869号;WO02/11715号;WO02/12166号;WO02/12178号;WO03/007949号;WO03/009847号;WO04/024720号;WO04/078716号;WO04/078717号;WO04/087159号;WO04/089307号;及びWO05/009950号に開示されているものなど、他のMc4r(メラノコルチン4受容体)アゴニスト);(16)5HT−2アゴニスト;(17)BVT933、DPCA37215、WAY161503、R−1065並びに米国特許第3,914,250号並びにPCT出願WO02/36596号、WO02/48124号、WO02/10169号、WO01/66548号、WO02/44152号、WO02/51844号、WO02/40456号及びWO02/40457号に開示されているものなどの5HT2C(セロトニン受容体2C)アゴニスト;(18)ガラニンアンタゴニスト;(19)CCKアゴニスト;(20)AR−R15849、GI181771、JMV−180、A−71378、A−71623及びSR146131並びに米国特許第5,739,106号に記載されているものなどのCCK−A(コレシストキニン−A)アゴニスト;(21)GLP−1アゴニスト;(22)コルチコトロピン放出ホルモンアゴニスト;(23)ヒスタミン受容体−3(H3)調節物質;(24)ヒオペラアミド、3−(1H−イミダゾール−4−イル)プロピルN−(4−ペンテニル)カルバマート、クロベンプロピト、ヨードフェンプロピト、イモプロキイファン、GT2394(Gliatech)並びにPCT出願WO02/15905号に記載及び開示されているもの;並びにO−[3−(1H−イミダゾール−4−イル)プロパノール]−カルバマート(Kiec−Kononowicz,K.et al.,Pharmazie,55:349−55(2000))、ピペリジン含有ヒスタミンH3受容体アンタゴニスト(Lazewska,D.et al.,Pharmazie,56:927−32(2001))、ベンゾフェノン誘導体及び関連化合物(Sasse,A.et al.,Arch.Pharm.(Weinheim)334:45−52(2001))、置換されたN−フェニルカルバマート(Reidemeister,S.et al.,Pharmazie,55:83−6(2000))及びプロキシファン誘導体(Sasse,A.et al.,J.Med.Chem.43:3335−43(2000))などのヒスタミン受容体−3(H3)アンタゴニスト/逆アゴニスト;(25)β−ヒドロキシステロイド脱水素酵素−1阻害剤(β−HSD−1);(26)テオフィリン、ペントキシフィリン、ザプリナスト、シルデナフィル、アムリノン、ミルリノン、シロスタミド、ロリプラム及びシロミラストなどのPDE(ホスホジエステラーゼ)阻害剤;(27)ホスホジエステラーゼ3B(PDE3B)阻害剤;(28)GW320659、デスピラミン、タルスプラム及びノミフェンシンなどのNE(ノルエピネフリン)輸送阻害剤;(29)PCT出願WO01/87335号及びWO02/08250号に開示されているものなどのグレリン受容体アンタゴニスト;(30)組み換えヒトレプチン(PEG−OB,Hoffman La Roche)及び組み換えメチオニルヒトレプチン(Amgen)を含むレプチン;(31)米国特許第5,552,524号、米国特許
第5,552,523号、米国特許第5,552,522号、米国特許第5,521,283号並びにPCT国際公開WO96/23513号、WO96/23514号、WO96/23515号、WO96/23516号、WO96/23517号、WO96/23518号、WO96/23519号及びWO96/23520号;(32)[D−Phe6,β−Ala11,Phe13,Nle14]Bn(6−14)及び[D−Phe6,Phe13]Bn(6−13)プロピルアミド並びにPept.Sci.2002Aug;8(8):461−75に開示されている化合物などのBRS3(ボンベシン受容体サブタイプ3)アゴニスト;(33)GI−181771(Glaxo−SmithKline)、SR146131(SanofiSynthelabo)、ブタビンジド、PD170,292及びPD149164(Pfizer)などのCNTF(毛様体神経栄養因子);(34)アクソキン(Regeneron)並びにPCT出願WO94/09134号、WO98/22128号及びWO99/43813号に開示されているものなどのCNTF誘導体;(35)シブトラミン並びに米国特許第4,746,680号、米国特許第4,806,570号及び米国特許第5,436,272号、米国特許公開2002/0006964並びにPCT出願WO01/27068号及びWO01/62341号に開示されているものなどのモノアミン再取り込み阻害剤;(36)フィタン酸、4−[(E)−2−(5,6,7,8−テトラヒドロ−5,5,8,8−テトラメチル−2−ナフタレニル)−1−プロペニル]安息香酸(TTNPB)、レチノイン酸及びPCT特許出願WO99/00123号に開示されているものなど、UCP−1(脱共役タンパク質−1、2又は3活性化因子);(37)KB−2611(KaroBioBMS)並びにPCT出願WO02/15845号及び日本国特許出願JP2000256190号に開示されているものなどの甲状腺ホルモンβアゴニスト;(38)セルレニン及びC75などのFAS(脂肪酸合成酵素)阻害剤;(39)DGAT1(ジアシルグリセロールアシル転移酵素1)阻害剤;(40)DGAT2(ジアシルグリセロールアシル転移酵素2)阻害剤;(41)ACC2(アセチル−CoAカルボキシラーゼ−2)阻害剤;(42)グルココルチコイドアンタゴニスト;(43)「del Mar−Grasa,M.et al.,Obesity Research,9:202−9(2001)」に開示されているオレオイル−エストロンなどの、アシル−エストロゲン;(44)イソロイシン、チアゾリジド、バリンピロリジド、NVP−DPP728、LAF237、P93/01、TSL225、TMC−2A/2B/2C、FE999011、P9310/K364、VIP0177、SDZ274−444;並びに米国特許第6,699,871号(参照により、本明細書に組み込まれる。);及び国際特許出願WO03/004498号;WO03/004496号;EP1258476号;WO02/083128号;WO02/062764号;WO03/000250号;WO03/002530号;WO03/002531号;WO03/002553号;WO03/002593号;WO03/000180号;及びWO03/000181号に開示されている化合物などの、ジペプチジルペプチダーゼIV(DP−IV)阻害剤;(46)ジカルボキシラート輸送体阻害剤;(47)グルコース輸送体阻害剤;(48)リン酸輸送体阻害剤;(49)メトフォルミン(Glucophage(R));及び(50)トピラマート(Topimax(R));並びに(50)BIM−43073D、BIM−43004C(Olitvak,D.A.et al.,Dig.Dis.Sci.44(3):643−48(1999))並びに米国特許第5,026,685号、米国特許第5,604,203号、米国特許第5,574,010号、米国特許第5,696,093号、米国特許第5,936,092号、米国特許第6,046,162号、米国特許第6,046,167号、米国特許第6,093,692号、米国特許第6,225,445、米国特許第5,604,203号、米国特許第4,002,531号、米国特許第4,179,337号、米国特許第5,122,614号、米国特許第5,349,052号、米国特許第5,552,520号、米国特許第6,127,355、WO95/06058号、WO98/32466号、WO03/026591号、WO03/057235号、WO03/027637及びWO2004/066966(参照により、本明細書に組み込まれる。)に開示されているものなどのペプチドYY、PYY3−36、ペプチドYY類縁体、誘導体及び断片;(51)NPY3−36、Nアセチル[Leu(28,31)]NPY24−36、TASP−V及びシクロ−(28/32)−Ac−[Lys28−Glu32]−(25−36)−pNPYなどのニューロペプチドY2(NPY2)受容体アゴニスト;(52)「Batterham et al.,J.Clin.Endocrinol.Metab.88:3989−3992(2003)」に記載されているような膵臓ペプチド(PP)及び1229U91などの他のY4アゴニストなどのニューロペプチドY4(NPY4)アゴニスト;(54)エトリコキシブ、セレコキシブ、バルデコキシブ、パレコキシブ、ルミラコキシブ、BMS347070、チラコキシブ又はJTE522、ABT963、CS502及びGW406381並びに医薬として許容されるこれらの塩などのシクロオキシゲナーゼ−2阻害剤;(55)BIBP3226、J−115814、BIBO3304、LY−357897、CP−671906、GI−264879A並びに米国特許第6,001,836号並びにWO96/14307号、WO01/23387号、WO99/51600号、WO01/85690号、WO01/85098号、WO01/85173号及びWO01/89528号に開示されているものなどの、ニューロペプチドY1(NPY1)アンタゴニスト;(56)ナルメフェン(Revex(R))、3−メトキシナルトレキソン、ナロキソン、ナルトレキソン及びPCT出願WO0/21509号に開示されているものなどのオピオイドアンタゴニスト;(57)BVT3498、BVT2733並びにWO01/90091号、WO01/90090号、WO01/90092号並びに米国特許第6,730,690号及び米国特許公開US2004−0133011(これらは、参照により、全体が本明細書中に組み込まれる。)に開示されているものなどの11βHSD−1(11−βヒドロキシステロイド脱水素酵素1型)阻害剤;並びに(58)アミノレックス;(59)アムフェクロラール;(60)アンフェタミン;(61)ベンゾフェタミン;(62)クロルフェンテルミン;(63)クロベンゾレックス;(64)クロフォレックス;(65)クロミノレックス;(66)クロルテルミン;(67)シクレキセドリン;(68)デキストロアンフェタミン;(69)ジフェメトキシジン;(70)N−エチルアンフェタミン;(71)フェンブトラザート;(72)フェニソレックス;(73)フェンプロポレックス;(74)フルドレックス;(75)フルミノレックス;(76)フルフリルメチルアンフェタミン;(77)レバムフェタミン;(78)レボファセトペラン;(79)メフェノレックス;(80)メタムフェプラモン;(81)メタアンフェタミン;(82)ノルシュードエフェドリン;(83)ペントレックス;(84)フェンジメトラジン;(85)フェンメトラジン;(86)ピシロレックス;(87)フィロファーム57;(88)ゾニサミド並びに(89)米国特許第5,162,339号、5,232,929号、米国特許第5,242,930号、米国特許第5,373,003号、米国特許第5,387,595号、米国特許第5,459,270号、米国特許第5,494,926号、米国特許第5,496,833号及び米国特許第5,637,699号;PCT国際公開WO90/05525号、同90/05729号、同91/09844号、同91/18899号、同92/01688号、同92/06079号、同92/12151号、同92/15585号、同92/17449号、同92/20661号、同92/20676号、同92/21677号、同92/22569号、同93/00330号、同93/00331号、同93/01159号、同93/01165号、同93/01169号、同93/01170号、同93/06099号、同93/09116号、同93/10073号、同93/14084号、同93/14113号、同93/18023号、同93/19064号、同93/21155号、同93/21181号、同93/23380号、同93/24465号、同94/00440号、同94/01402号、同94/02461号、同94/02595号、同94/03429号、同94/03445号、同94/04494号、同94/04496号、同94/05625号、同94/07843号、同94/08997号、同94/10165号、同94/10167号、同94/10168号、同94/10170号、同94/11368号、同94/13639号、同94/13663号、同94/14767号、同94/15903号、同94/19320号、同94/19323号、同94/20500号、同94/26735号、同94/26740号、同94/29309号、同95/02595号、同95/04040号、同95/04042号、同95/06645号、同95/07886号、同95/07908号、同95/08549号、同95/11880号、同95/14017号、同95/15311号、同95/16679号、同95/17382号、同95/18124号、同95/18129号、同95/19344号、同95/20575号、同95/21819号、同95/22525号、同95/23798号、同95/26338号、同95/28418号、同95/30674号、同95/30687号、同95/33744号、同96/05181号、同96/05193号、同96/05203号、同96/06094号、同96/07649号、同96/10562号、同96/16939号、同96/18643号、同96/20197号、同96/21661号、同96/29304号、同96/29317号、同96/29326号、同96/29328号、同96/31214号、同96/32385号、同96/37489号、同97/01553号、同97/01554号、同97/03066号、同97/08144号、同97/14671号、同97/17362号、同97/18206号、同97/19084号、同97/19942号、同97/21702号、同97/49710号に開示されている化合物などの、ニューロキニン−1受容体アンタゴニスト(NK−1アンタゴニスト)などの肥満抑制剤。
ATCC#PTA−5316(MA7327)及びATCC#PTA−5317(MA7331)の両方に対して、同じ方法を適用した。
発酵ブロス43Lへ、MeOH29Lを添加し、pH3.0に酸性化して、72Lの最終容量を得た。この抽出物をろ過し、1.5Lのアンバークロム上にろ液を直接添加し、40から100%MeOH水溶液の勾配で溶出し、各画分600mLを収集した。主に化合物Iを含有する画分11から13をプールし、主として水性の200mLまで濃縮し、これを水300mLで希釈して、500mLの最終容量を得た。固体の重炭酸ナトリウムを添加して、pHを9.0に上昇させた。塩化メチレンの同等量を用い、この溶液を3回抽出した。水層を6NHCl(塩酸)でpH2.0まで酸性化し、塩化メチレンの同等量で4回抽出し、合わせた抽出物(1900cc)を半精製された化合物I2.6gに濃縮した。
発酵ブロス5Lを4NHClで酸性化し、重炭酸ナトリウムの5%水溶液300mlで抽出された酢酸イソプロピル2.5リットルで抽出した。重炭酸層を150mLのアンバークロムに添加し、溶出剤のpHが中性になるまで水で洗浄した。0.1NHClの1カラム容量でカラムを洗浄し、溶出剤のpHが中性になるまで水で洗浄した。20、40、60、80、90及び100%メタノール水溶液の各2カラム容量でカラムを溶出した。化合物Iは、90及び100%水性メタノール画分中に溶出された。プールされた画分を、減圧下で主に水溶液に濃縮し、塩化メチレンの同等量(酢酸イソプロピル及び酢酸エチルが同等に効果的であった。)で抽出した。有機層を濃縮乾固して、化合物I193mgを非晶質粉末として得て、熱いニトロメタン、酢酸イソプロピル、酢酸エチル又はアセトニトリル−水から結晶化し得る。
化合物Iは、もみ革色の針状物として、融点220から223℃(230℃で分解)で、ニトロメタンから結晶化された。
FTIR(ZnSe)3400、2964、1713(w)、1650(br、強)、1535、1446、1378、1296、1240、1153、1105、1091、1024、953、828、791、608cm−1、
HEESIFTMS:検出442.1853、C24H27NO7+Hに対する計算値:442.1866、
1HNMR(500MHz)C5D5NδH:1.14(3H,s),1.40(3H,s),1.48(3H,d,J=11Hz),1.57(1H,dd,J=11.5,6.5Hz),1.73(1H,dd,J=10.5,3Hz),1.81(2H,brd,J=11.5Hz),1.90(1H,m),2.0(1H,m),2.20(1H,t,J=6.5Hz),2.45(1H,brs),2.68(1H,m),2.75(1H,ddd,J=14.5,11.5,5),2.83(1H,ddd,J=14.5,11.5,5.5Hz),4.49(1H,t,J=3.5Hz),5.94(1H,d,J=10Hz),6.37(1H,d,J=10Hz),6.87(1H,d,J=9Hz),8.12(1H,d,J=9Hz),10.5(1H,s);
13CNMR(125MHz)C5D5Nδc:23.9,25.1,32.4,32.8,41.4,43.7,45.7,46.8,47.2,47.4,55.6,77.1,87.5,107.8,110.5,115.9,127.9,130.1,154.6,158.5,159.1,175.0,175.2,203.8。
成長の観察、一般的な培養の特性及び炭素源利用は、Shirling and Gottliebの方法(Int.J.Syst.Bacteriol.(1996)16:313−340)に従って行った。培養の着色は、Methuen Handbook of Colour(A.Kornerup and J.H.Wauscher、第三版、1978)に含有される色度標準と比較することによって決定した。
株ATCC#PTA−5316(MA7327)は、Eastern Cape,South Africaで収集された土壌から得られた。土壌試料は、フィンボス及び砂丘の沿岸地域において、マヌレ・オボバータ(Manulea obovbata)の根圏に関連した。土壌試料を段階希釈し、20μg/mlのナリジクス酸を含有するデンブンカゼイン寒天培地上に播種した後、菌株を単離した。
株ATCCPTA−5316(MA7327)は、酵母麦芽抽出物、オートミール、グリセロールアスパラギン、無機塩デンプン及びトリプチカーゼ大豆寒天培地などの多種の寒天培地上で、28℃で、良好に成長する。全体のコロニーの形態は、ストレプトマイセト(Streptomycete)に典型的なものであり、胞子集団の色調、基質菌糸体の色素沈着及び様々な色素の産生を含む、その成長の特性を様々な寒天培地において記録した(表2)。
当初黄白色であった基質菌糸体は、温置の21日後、橙褐色(5C6)に変化する。21日の温置後、当初白色であった気菌糸は成長を続け、黄灰色に変化し、最終的に、褐色の湿潤した浸出液の液滴を伴い灰色(5D2)となる。
光学顕微鏡により、400x及び1000xの倍率下において、胞子鎖の形態をプレート上で直接調べた。麦芽酵母抽出物寒天培地上において、培養の7日、14日及び21日間後に、観察を行った。気菌糸は、大きく分枝した基質菌糸から生じる。分枝した疎らな気中菌糸は、最初に、短く不規則で堅固な胞子鎖の螺旋物に分化する。10から20個未満の胞子によって担胞子体が形成され、時間が経つにつれて、より古い培養液中で、暗色の粘液状の胞子集団に合着する傾向がある。同様の形態が、他の試験培地の大部分おいても観察されたが、合着の程度は様々であった。これに対して、グリセロールアスパラギン寒天培地において、菌株は、不稔性の栄養菌子として成長する。
当初黄白色であった基質菌糸体は、温置の21日後、黄褐色(5E7)に変化する。21日の温置後、当初黄白色であった気菌糸は成長を続け、均一に灰色(5E1)になる。
光学顕微鏡により、400x及び1000xの倍率下において、胞子鎖の形態をプレート上で直接調べた。麦芽酵母抽出物寒天培地上において、培養の7日、14日及び21日間後に、観察を行った。大きな気菌糸が、分枝した基質菌糸から生じる。担胞子体は、気中菌糸の頂端部に又は二次分枝菌糸中に生じる。それらは、ループ状又はコイル状の短く堅固で不規則な胞子鎖を形成し、より長時間の温置後に合着する。菌株が不稔性の栄養菌糸として成長するグリセロールアスパラギン寒天培地を除く他の試験培地において、合着の程度が異なる同様の形態が観察された。
細胞壁組成の分析は、株ATCC#PTA−5316(MA7327)及びATCC#PTA−5317(MA7331)が、全生物体の加水分解物において、ストレプトミセスの特徴であるLL−A2pmを含有していることを示している。株ATCC#PTA−5316(MA7327)は、主要な細胞壁糖質としてグルコースを含有するのに対して、株ATCC#PTA−5317(MA7331)では、特徴的な糖としてグルコース及びガラクトースが見出される。両株は、直鎖並びにイソ及びアンテイソ飽和脂肪酸に富んでいるが、完全に異なる脂肪酸パターンを示す。完全な脂肪酸組成が表2に提供されている。完全な細胞の加メタノール分解物中に見出される主な脂肪酸は、15:0アンテイソ及び16:0イソに相当し、これもまた、ストレプトミセスに典型的である。これらの化学分類学的分析は全て、両株がストレプトミセス属のメンバーに相当することを示している。
これらの株は、僅かに異なる炭素利用パターンを示している(表4)。
両株に対して、16SrDNAの完全な配列を決定した。配列は、Genbank(AB045882)からのストレプトミセスヌクレオチド配列と整列させ、126種類の実証されたストレプトミセス種の整列された16SrDNA配列の系統発生的分析により、両株の分類学的位置を決定した。最節約法を使用し、これらの16SrDNA配列に基づいた系統樹を構築した。各分類からのブートストラップ反復データを統計信頼度の基準として使用した。ブートストラップ反復データの95%で見られる分類は、統計的に有意であるとみなされた。
発酵ブロス2リットルへ、アセトン2リットルを添加し、振盪器上で2時間振盪して、ろ過した。ろ液を減圧下で濃縮し、アセトンの大部分を除去して、75mLのアンバークロム(CG161s)カラム上に入れた。カラムは、広帯域で化合物を溶出する90%水から100%メタノールの勾配で溶出し、濃縮及び凍結乾燥すると、半精製された画分170mgが得られた。0.1%トリフルオロ酢酸を含有する20から98%アセトニトリル水溶液の勾配で、分取HPLC(Zorbax Rx C8 21.4×250mm)により、画分の80mg部分を精製し、化合物Iの1.1mgを生成した。スペクトル分析により、構造を解明した(下記参照)。
MF C24H27NO6
HEESIFTMS 実測:426.1911;M+Hに対する計算値:426.1911
[α]23 D +2.1°(c0.96、CH3OH)
UV(CH3OH)λmax 226(ε16,837)296(2,663)nm
化合物IIの培養MA−7339産生株の一般的概要を説明する。
菌株MA7339は、Mallorca,Balearic Islands,Spainで収集された土壌から得た。菌株は、1%(w/v)クロラミンTで土壌を前処理し、20μg/mlのナリジクス酸が補充されたフミン酸ベースの寒天培地に播種した後に単離された。酵母麦芽抽出物寒天上での精製後、FabF SPAR C中で寒天プラグとして検査したときに、単離株は活性を有することが検出された。
株MA7339は、酵母麦芽抽出物、オートミール、グリセロールアスパラギン、無機塩デンプン及びトリプチカーゼ大豆寒天培地などの多様な寒天培地上で、28℃にて、良好に成長する。全体のコロニーの形態は、ストレプトミセトに典型的なものであり、胞子集団の色調、基質菌糸体の色素沈着及び様々な色素の産生を含む、その成長の特性を様々な寒天培地において記録する(表7)。
当初白黄色であった基質菌糸体は、温置の21日後、黄褐色(5D7)に変化する。21日の温置後、当初白色であった気菌糸は成長を続け、褐色の湿潤した浸出液の液滴を伴い白灰色(5E1/5E2)に変化する。
細胞壁組成の分析は、株MA7339が、全生物体の加水分解物中に、ストレプトミセスの特徴であるLL−A2pm、並びにグルコース及びリボースを主な細胞壁糖として含有していることを示している。菌株は、直鎖並びにイソ及びアンテイソ飽和脂肪酸に富んでおり、全細胞の加メタノール分解物は、同じくストレプトミセスに典型的である主な脂肪酸の15:0アンテイソ(12.43%)及び16:0イソ(17.94%)を含有する。しかしながら、主成分は、脂肪酸種15:0イソ(20.43%)である。完全な脂肪酸組成は、表8に提供されている。
株MA7339は、次の炭素利用パターンを示している(表9)。
スクロース、D−キシロース、D−フルクトース及びラフィノースの良好な利用;D−グルコース、I−イノシトール及びD−マンニトールの中程度の利用;L−アラビノース、セルロース及びラムノースの利用なし。
株MA−7339について、16SrDNAの完全な配列を決定した。配列は、Genbank(AB045882)からのストレプトミセスヌクレオチド配列並びにS.プラテンシス株MA7327及びMA7331と並列させた。最節約法を使用して、これらの16SrDNA配列に基づいた系統樹を構築した。各分類からのブートストラップ反復データを統計信頼度の基準として使用した。ブートストラップ反復データの95%で見られる分類は、統計的に有意であるとみなされた。
初代肝細胞を雄CDラット(250g)から調製し、0.8×106細胞/ウェルの密度にて、10%ウシ胎仔血清を加えた肝細胞付着培地中のPrimaria6ウェル上に一晩配置した。PBSで細胞を2回洗浄し、DMEM高グルコース培地2mLと加えた。肝細胞中の脂肪酸及びステロール合成は、改変を加えて、以前に記載したとおりに測定された(Jiang G,Li Z、Liu F,Ellsworth K,Dallas−Yang Q,Wu M、Ronan J,Essau C,Murphy C,Szalkowski D,Bergeron R,Doebber T and Zhang B.Prevention of obesity in mice by antisense oligonucleotide inhibitors of stearoyl−CoA desaturase−1.J.Clin.Invest.115:1030−1038(2003);Jiang G,Li Z,Liu F,Ellsworth K,Dallas−Yang Q,Wu M,Ronan J,Essau C,Murphy C,Szalkowski D,Bergeron R,Doebber T and Zhang B.Prevention of obesity in mice by antisense oligonucleotide inhibitors of stearoyl−CoA desaturase−1.J.Clin.Invest.115:1030−1038(2003))。DMSO5μl中の化合物とともに、60分間にわたって細胞を予め温置し、次いでウェル当たり0.5μCiにて、C14−アセタート(NEN)を添加した。ウェルは、O2−CO2(95%−5%)でガス供給され、更に2時間温置するため、プレートをパラフィルムで密閉した。温置後、PBSで細胞を2回洗浄し、ウェル当たりメタノール中の10%KOH2.5mL及び蒸留水1.0mLと混合した。混合物を90℃で3時間加熱し、石油エーテル(PE)4mLで抽出した。上部のPE層3mLをシンチレーション瓶中へ移し、低熱下で乾燥させ、次いでC14−ステロールのレベルを計数した。下部の水層3mlを10MH2SO4(PH<2.0)1.0mlに添加し、十分混合して、次いでPE4mlで抽出した。上部の層3mlを低熱下で乾燥させ、C14−脂肪酸のレベルを計数した。肝細胞中の脂肪酸酸化は、C14−オレイン酸の可溶性酸生成物への転化を、改変を加えて記載どおり決定した(Jiang G,Li Z,Liu F,Ellsworth K,Dallas−Yang Q,Wu M,Ronan J,Essau C,Murphy C,Szalkowski D,Bergeron R,Doebber T and Zhang B.Prevention of obesity in mice by antisense oligonucleotide inhibitors of stearoyl−CoA desaturase−1.J.Clin.Invest.115:1030−1038(2003);Mannaerts GP,Debeer LJ,Thomas J,ans DeSchepper PJ.Mitochondrial and proxisomal fatty acid oxidation in liver homogenates and isolated hepatocytes from control and clofibrate−treated rats.J.Biol.Chem.254:4585−4595(1979))。肝細胞を一晩播種し、PBSで2回洗浄し、次いで0.25%ウシ血清アルブミンを加えた2mlの199培地において、DMSO5μl中の化合物とともに、60分間にわたって予め温置した。C14−オレイン酸0.25μCi(NEN)を各ウェルに加えた。プレートはガス供給され、密閉された。1時間の温置後、培地1mLを取り除き、10%BSA100μlと混合し、次いで60%HClO4100μlと混合した。遠心分離後、溶液1mLで可溶性酸生成物のレベルを計数した。
C57BL/6Nマウスに式I600μg/時間を継続的に注入した(注入プロトコルに関しては、Wang et al.,2006,Nature 441:358を参照。)。標準的な方法を使用することにより測定されたビヒクル対照と比較すると、3日間の注入により、血漿グルコースが63.9%低下する。脂肪酸の阻害は、マロニルCoAの蓄積をもたらし、次に、マロニルCoAの蓄積は脂肪酸酸化を阻害して、グルコースの代謝を高める。
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EP2698157A1 (en) | 2014-02-19 |
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AU2007300627B2 (en) | 2012-02-16 |
AU2007300627A1 (en) | 2008-04-03 |
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US20100022630A1 (en) | 2010-01-28 |
US8173629B2 (en) | 2012-05-08 |
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CA2664113C (en) | 2013-05-28 |
CA2770486A1 (en) | 2008-04-03 |
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