JP2011508778A - シトクロムp450のインヒビター - Google Patents
シトクロムp450のインヒビター Download PDFInfo
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- JP2011508778A JP2011508778A JP2010541484A JP2010541484A JP2011508778A JP 2011508778 A JP2011508778 A JP 2011508778A JP 2010541484 A JP2010541484 A JP 2010541484A JP 2010541484 A JP2010541484 A JP 2010541484A JP 2011508778 A JP2011508778 A JP 2011508778A
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- 0 **N(*)C(*)CC(*)N(*)C(I**)=O Chemical compound **N(*)C(*)CC(*)N(*)C(I**)=O 0.000 description 3
- NMILGIZTAZXMTM-UHFFFAOYSA-N CCCN1CCOCC1 Chemical compound CCCN1CCOCC1 NMILGIZTAZXMTM-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
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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
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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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
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
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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
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
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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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
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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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
Abstract
Description
本願は、一般に、同時に投与される薬物の薬物速度論を改変(例えば、改善)する化合物および薬学的組成物、ならびにこれらの化合物を薬物と同時に投与することにより、この薬物の薬物速度論を改変(例えば、改善)する方法に関する。
シトクロムP450酵素による酸化代謝は、薬物代謝の主要な機構の1つである。シトクロムP450酵素により迅速に代謝される薬物の、治療上有効な血漿中レベルを維持することは、困難であり得る。従って、シトクロムP450酵素分解を受けやすい薬物の血漿中レベルは、シトクロムP450インヒビターの同時投与(これによって、その薬物の薬物速度論を改善する)によって維持または増強され得る。
本願の1つの局面は、同時に投与される薬物の薬物速度論を、例えば、シトクロムP450モノオキシゲナーゼを阻害することによって改変(例えば、改善)する、化合物および薬学的組成物に関する。
X1は、-C(O)−O−、−S(O)−、および−S(O2)−、−C(O)NR6−からなる群より選択され;
X2は、-O−、-NR6−C(O)−NR6−、−OC(O)NR6−、−NR6−、および−NR6C(O)O−からなる群より選択され;
Lは、共有結合、アルキレン、および-CHR7−からなる群より選択され;
R1は、アリール、ヘテロアリール、アリールアルキル、およびヘテロアリールアルキルからなる群より選択され;
各R2は独立して、H、アルキル、アリールアルキル、ヘテロシクリルアルキル、およびシクロアルキルアルキルからなる群より選択されここで少なくとも1つのR2は、アルキル、アリールアルキル、ヘテロシクリルアルキルまたはシクロアルキルアルキルであり;
R3は、ヘテロシクリル、アリール、ヘテロアリール、アリールアルキル、およびヘテロアリールアルキルからなる群より選択され;
R4およびR5は各々独立して、H、アルキル、シクロアルキル、ヘテロシクリル、シクロアルキルアルキル、アリールアルキル、およびヘテロアリールアルキルからなる群より選択され;
各R6は独立して、H、アルキル、およびシクロアルキルからなる群より選択され;そして
R7は、H、アルキル、置換アルキル、およびヘテロシクリルアルキルであり;
ここでR1、R2、R3、R4、R5およびR7の各アリール、ヘテロアリール、ヘテロシクリル、ヘテロシクリルアルキル、アリールアルキル、およびヘテロアリールアルキルは、置換されていないかまたは置換されている。
a)式Iの化合物、あるいはその薬学的に受容可能な塩、溶媒和物、および/またはエステルを含有する第一の薬学的組成物;ならびに
b)シトクロムP450モノオキシゲナーゼにより代謝される少なくとも1種のさらなる活性薬剤を含有する第二の薬学的組成物、
を含有する、組み合わせ薬学的薬剤を提供する。
ここで本発明の特定の請求項が詳細に参照され、それらの例は、付随する構造および式に図示されている。本発明は、列挙される特許請求の範囲に関連して説明されるが、本発明をこれらの請求項に限定することは意図されないことが、理解される。逆に、本発明は、特許請求の範囲により規定される本発明の範囲内に含まれ得る、全ての代替物、改変物、および均等物を網羅することが意図される。
他のことが記載されない限り、以下の用語および語句は、本明細書中で使用される場合、以下の意味を有することが意図される:
商品名が本明細書中で使用される場合、出願人は、その商品名の製品、およびその商品名の製品の活性薬学的成分を独立して含むことを意図する。
「Ac」とは、アセチル(−C(O)CH3)を意味する。
本発明の文脈において、保護基は、プロドラッグ部分および化学的保護基を包含する。
エステル形成基としては:(1)ホスホネートエステル形成基(例えば、ホスホンアミデートエステル、ホスホロチオエートエステル、ホスホネートエステル、およびホスホン−ビス−アミデート);(2)カルボキシルエステル形成基、ならびに(3)硫黄エステル形成基(例えば、スルホン酸エステル、硫酸エステル、およびスルフィン酸エステル)が挙げられる。
本明細書中に記載される化合物のインビボ代謝産物もまた、本発明の範囲内に入る。このような産物は、投与される化合物の、特に酵素プロセスに起因する、酸化、還元、加水分解、アミド化、エステル化などから生じ得る。従って、本発明は、本発明の化合物を哺乳動物に、この化合物の代謝産物を生じるために充分な時間にわたって接触させる工程を包含するプロセスによって、生成された化合物を包含する。このような生成物は、代表的に、放射線標識(例えば、C14またはH3)された本発明の化合物を調製すること、この化合物を検出可能な用量(例えば、約0.5mg/kgより多量)で、動物(例えば、ラット、マウス、モルモット、サル)またはヒトに非経口投与すること、代謝が起こるために充分な時間(代表的に、約30秒〜30時間)を与えること、およびその変換生成物を、尿、血液または他の生物学的サンプルから単離することによって、同定される。これらの生成物は、容易に単離される。なぜなら、これらの生成物は、標識されているからである(他の化合物は、代謝産物中に残っているエピトープに結合し得る抗体の使用によって、単離される)。代謝産物の構造は、従来の様式で(例えば、MSまたはNMR分析によって)決定される。一般に、代謝産物の分析は、当業者に周知である従来の薬物代謝研究と同じ様式で行われる。変換生成物は、他の方法ではインビボに見出されない限り、単独では抗感染活性を有さない場合でさえも、本発明の化合物の治療的用量についての診断アッセイにおいて有用である。
式Iの化合物の別の実施形態において、R1は、置換または非置換のアリールである。
Z1.T1A.T2A.Y1A.Y2A, Z1.T1A.T2A.Y1A.Y2B, Z1.T1A.T2A.Y1A.Y2C, Z1.T1A.T2A.Y1A.Y2D, Z1.T1A.T2A.Y1B.Y2A, Z1.T1A.T2A.Y1B.Y2B, Z1.T1A.T2A.Y1B.Y2C, Z1.T1A.T2A.Y1B.Y2D, Z1.T1A.T2A.Y1C.Y2A, Z1.T1A.T2A.Y1C.Y2B, Z1.T1A.T2A.Y1C.Y2C, Z1.T1A.T2A.Y1C.Y2D, Z1.T1A.T2A.Y1D.Y2A, Z1.T1A.T2A.Y1D.Y2B, Z1.T1A.T2A.Y1D.Y2C, Z1.T1A.T2A.Y1D.Y2D, Z1.T1A.T2A.Y1E.Y2A, Z1.T1A.T2A.Y1E.Y2B, Z1.T1A.T2A.Y1E.Y2C, Z1.T1A.T2A.Y1E.Y2D, Z1.T1A.T2B.Y1A.Y2A, Z1.T1A.T2B.Y1A.Y2B, Z1.T1A.T2B.Y1A.Y2C, Z1.T1A.T2B.Y1A.Y2D, Z1.T1A.T2B.Y1B.Y2A, Z1.T1A.T2B.Y1B.Y2B, Z1.T1A.T2B.Y1B.Y2C, Z1.T1A.T2B.Y1B.Y2D, Z1.T1A.T2B.Y1C.Y2A, Z1.T1A.T2B.Y1C.Y2B, Z1.T1A.T2B.Y1C.Y2C, Z1.T1A.T2B.Y1C.Y2D, Z1.T1A.T2B.Y1D.Y2A, Z1.T1A.T2B.Y1D.Y2B, Z1.T1A.T2B.Y1D.Y2C, Z1.T1A.T2B.Y1D.Y2D, Z1.T1A.T2B.Y1E.Y2A, Z1.T1A.T2B.Y1E.Y2B, Z1.T1A.T2B.Y1E.Y2C, Z1.T1A.T2B.Y1E.Y2D, Z1.T1A.T2C.Y1A.Y2A, Z1.T1A.T2C.Y1A.Y2B, Z1.T1A.T2C.Y1A.Y2C, Z1.T1A.T2C.Y1A.Y2D, Z1.T1A.T2C.Y1B.Y2A, Z1.T1A.T2C.Y1B.Y2B, Z1.T1A.T2C.Y1B.Y2C, Z1.T1A.T2C.Y1B.Y2D, Z1.T1A.T2C.Y1C.Y2A, Z1.T1A.T2C.Y1C.Y2B, 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Z7.T1C.T2B.Y1A.Y2A, Z7.T1C.T2B.Y1A.Y2B, Z7.T1C.T2B.Y1A.Y2C, Z7.T1C.T2B.Y1A.Y2D, Z7.T1C.T2B.Y1B.Y2A, Z7.T1C.T2B.Y1B.Y2B, Z7.T1C.T2B.Y1B.Y2C, Z7.T1C.T2B.Y1B.Y2D, Z7.T1C.T2B.Y1C.Y2A, Z7.T1C.T2B.Y1C.Y2B, Z7.T1C.T2B.Y1C.Y2C, Z7.T1C.T2B.Y1C.Y2D, Z7.T1C.T2B.Y1D.Y2A, Z7.T1C.T2B.Y1D.Y2B, Z7.T1C.T2B.Y1D.Y2C, Z7.T1C.T2B.Y1D.Y2D, Z7.T1C.T2B.Y1E.Y2A, Z7.T1C.T2B.Y1E.Y2B, Z7.T1C.T2B.Y1E.Y2C, Z7.T1C.T2B.Y1E.Y2D, Z7.T1C.T2C.Y1A.Y2A, Z7.T1C.T2C.Y1A.Y2B, Z7.T1C.T2C.Y1A.Y2C, Z7.T1C.T2C.Y1A.Y2D, Z7.T1C.T2C.Y1B.Y2A, Z7.T1C.T2C.Y1B.Y2B, Z7.T1C.T2C.Y1B.Y2C, Z7.T1C.T2C.Y1B.Y2D, Z7.T1C.T2C.Y1C.Y2A, Z7.T1C.T2C.Y1C.Y2B, Z7.T1C.T2C.Y1C.Y2C, Z7.T1C.T2C.Y1C.Y2D, Z7.T1C.T2C.Y1D.Y2A, Z7.T1C.T2C.Y1D.Y2B, Z7.T1C.T2C.Y1D.Y2C, Z7.T1C.T2C.Y1D.Y2D, Z7.T1C.T2C.Y1E.Y2A, Z7.T1C.T2C.Y1E.Y2B, Z7.T1C.T2C.Y1E.Y2C, Z7.T1C.T2C.Y1E.Y2D, Z7.T1D.T2A.Y1A.Y2A, Z7.T1D.T2A.Y1A.Y2B, Z7.T1D.T2A.Y1A.Y2C, Z7.T1D.T2A.Y1A.Y2D, Z7.T1D.T2A.Y1B.Y2A, Z7.T1D.T2A.Y1B.Y2B, Z7.T1D.T2A.Y1B.Y2C, Z7.T1D.T2A.Y1B.Y2D, Z7.T1D.T2A.Y1C.Y2A, Z7.T1D.T2A.Y1C.Y2B, Z7.T1D.T2A.Y1C.Y2C, Z7.T1D.T2A.Y1C.Y2D, Z7.T1D.T2A.Y1D.Y2A, Z7.T1D.T2A.Y1D.Y2B, Z7.T1D.T2A.Y1D.Y2C, Z7.T1D.T2A.Y1D.Y2D, Z7.T1D.T2A.Y1E.Y2A, Z7.T1D.T2A.Y1E.Y2B, Z7.T1D.T2A.Y1E.Y2C, Z7.T1D.T2A.Y1E.Y2D, Z7.T1D.T2B.Y1A.Y2A, Z7.T1D.T2B.Y1A.Y2B, Z7.T1D.T2B.Y1A.Y2C, Z7.T1D.T2B.Y1A.Y2D, Z7.T1D.T2B.Y1B.Y2A, Z7.T1D.T2B.Y1B.Y2B, Z7.T1D.T2B.Y1B.Y2C, Z7.T1D.T2B.Y1B.Y2D, Z7.T1D.T2B.Y1C.Y2A, Z7.T1D.T2B.Y1C.Y2B, Z7.T1D.T2B.Y1C.Y2C, Z7.T1D.T2B.Y1C.Y2D, Z7.T1D.T2B.Y1D.Y2A, Z7.T1D.T2B.Y1D.Y2B, Z7.T1D.T2B.Y1D.Y2C, Z7.T1D.T2B.Y1D.Y2D, Z7.T1D.T2B.Y1E.Y2A, Z7.T1D.T2B.Y1E.Y2B, Z7.T1D.T2B.Y1E.Y2C, Z7.T1D.T2B.Y1E.Y2D, Z7.T1D.T2C.Y1A.Y2A, Z7.T1D.T2C.Y1A.Y2B, Z7.T1D.T2C.Y1A.Y2C, Z7.T1D.T2C.Y1A.Y2D, Z7.T1D.T2C.Y1B.Y2A, Z7.T1D.T2C.Y1B.Y2B, Z7.T1D.T2C.Y1B.Y2C, Z7.T1D.T2C.Y1B.Y2D, Z7.T1D.T2C.Y1C.Y2A, Z7.T1D.T2C.Y1C.Y2B, Z7.T1D.T2C.Y1C.Y2C, Z7.T1D.T2C.Y1C.Y2D, Z7.T1D.T2C.Y1D.Y2A, Z7.T1D.T2C.Y1D.Y2B, Z7.T1D.T2C.Y1D.Y2C, Z7.T1D.T2C.Y1D.Y2D, Z7.T1D.T2C.Y1E.Y2A, Z7.T1D.T2C.Y1E.Y2B, Z7.T1D.T2C.Y1E.Y2C, Z7.T1D.T2C.Y1E.Y2D, Z7.T1E.T2A.Y1A.Y2A, Z7.T1E.T2A.Y1A.Y2B, Z7.T1E.T2A.Y1A.Y2C, Z7.T1E.T2A.Y1A.Y2D, Z7.T1E.T2A.Y1B.Y2A, Z7.T1E.T2A.Y1B.Y2B, Z7.T1E.T2A.Y1B.Y2C, Z7.T1E.T2A.Y1B.Y2D, Z7.T1E.T2A.Y1C.Y2A, Z7.T1E.T2A.Y1C.Y2B, Z7.T1E.T2A.Y1C.Y2C, Z7.T1E.T2A.Y1C.Y2D, Z7.T1E.T2A.Y1D.Y2A, Z7.T1E.T2A.Y1D.Y2B, Z7.T1E.T2A.Y1D.Y2C, Z7.T1E.T2A.Y1D.Y2D, Z7.T1E.T2A.Y1E.Y2A, Z7.T1E.T2A.Y1E.Y2B, Z7.T1E.T2A.Y1E.Y2C, Z7.T1E.T2A.Y1E.Y2D, Z7.T1E.T2B.Y1A.Y2A, Z7.T1E.T2B.Y1A.Y2B, Z7.T1E.T2B.Y1A.Y2C, Z7.T1E.T2B.Y1A.Y2D, Z7.T1E.T2B.Y1B.Y2A, Z7.T1E.T2B.Y1B.Y2B, Z7.T1E.T2B.Y1B.Y2C, Z7.T1E.T2B.Y1B.Y2D, Z7.T1E.T2B.Y1C.Y2A, Z7.T1E.T2B.Y1C.Y2B, Z7.T1E.T2B.Y1C.Y2C, Z7.T1E.T2B.Y1C.Y2D, Z7.T1E.T2B.Y1D.Y2A, Z7.T1E.T2B.Y1D.Y2B, Z7.T1E.T2B.Y1D.Y2C, Z7.T1E.T2B.Y1D.Y2D, Z7.T1E.T2B.Y1E.Y2A, Z7.T1E.T2B.Y1E.Y2B, Z7.T1E.T2B.Y1E.Y2C, Z7.T1E.T2B.Y1E.Y2D, Z7.T1E.T2C.Y1A.Y2A, Z7.T1E.T2C.Y1A.Y2B, Z7.T1E.T2C.Y1A.Y2C, Z7.T1E.T2C.Y1A.Y2D, Z7.T1E.T2C.Y1B.Y2A, Z7.T1E.T2C.Y1B.Y2B, Z7.T1E.T2C.Y1B.Y2C, Z7.T1E.T2C.Y1B.Y2D, Z7.T1E.T2C.Y1C.Y2A, Z7.T1E.T2C.Y1C.Y2B, Z7.T1E.T2C.Y1C.Y2C, Z7.T1E.T2C.Y1C.Y2D, Z7.T1E.T2C.Y1D.Y2A, Z7.T1E.T2C.Y1D.Y2B, Z7.T1E.T2C.Y1D.Y2C, Z7.T1E.T2C.Y1D.Y2D,
Z7.T1E.T2C.Y1E.Y2A, Z7.T1E.T2C.Y1E.Y2B, Z7.T1E.T2C.Y1E.Y2C, Z7.T1E.T2C.Y1E.Y2D, Z7.T1F.T2A.Y1A.Y2A, Z7.T1F.T2A.Y1A.Y2B, Z7.T1F.T2A.Y1A.Y2C, Z7.T1F.T2A.Y1A.Y2D, Z7.T1F.T2A.Y1B.Y2A, Z7.T1F.T2A.Y1B.Y2B, Z7.T1F.T2A.Y1B.Y2C, Z7.T1F.T2A.Y1B.Y2D, Z7.T1F.T2A.Y1C.Y2A, Z7.T1F.T2A.Y1C.Y2B, Z7.T1F.T2A.Y1C.Y2C, Z7.T1F.T2A.Y1C.Y2D, Z7.T1F.T2A.Y1D.Y2A, Z7.T1F.T2A.Y1D.Y2B, Z7.T1F.T2A.Y1D.Y2C, Z7.T1F.T2A.Y1D.Y2D, Z7.T1F.T2A.Y1E.Y2A, Z7.T1F.T2A.Y1E.Y2B, Z7.T1F.T2A.Y1E.Y2C, Z7.T1F.T2A.Y1E.Y2D, Z7.T1F.T2B.Y1A.Y2A, Z7.T1F.T2B.Y1A.Y2B, Z7.T1F.T2B.Y1A.Y2C, Z7.T1F.T2B.Y1A.Y2D, Z7.T1F.T2B.Y1B.Y2A, Z7.T1F.T2B.Y1B.Y2B, Z7.T1F.T2B.Y1B.Y2C, Z7.T1F.T2B.Y1B.Y2D, Z7.T1F.T2B.Y1C.Y2A, Z7.T1F.T2B.Y1C.Y2B, Z7.T1F.T2B.Y1C.Y2C, Z7.T1F.T2B.Y1C.Y2D, Z7.T1F.T2B.Y1D.Y2A, Z7.T1F.T2B.Y1D.Y2B, Z7.T1F.T2B.Y1D.Y2C, Z7.T1F.T2B.Y1D.Y2D, Z7.T1F.T2B.Y1E.Y2A, Z7.T1F.T2B.Y1E.Y2B, Z7.T1F.T2B.Y1E.Y2C, Z7.T1F.T2B.Y1E.Y2D, Z7.T1F.T2C.Y1A.Y2A, Z7.T1F.T2C.Y1A.Y2B, Z7.T1F.T2C.Y1A.Y2C, Z7.T1F.T2C.Y1A.Y2D, Z7.T1F.T2C.Y1B.Y2A, Z7.T1F.T2C.Y1B.Y2B, Z7.T1F.T2C.Y1B.Y2C, Z7.T1F.T2C.Y1B.Y2D, Z7.T1F.T2C.Y1C.Y2A, Z7.T1F.T2C.Y1C.Y2B, Z7.T1F.T2C.Y1C.Y2C, Z7.T1F.T2C.Y1C.Y2D, Z7.T1F.T2C.Y1D.Y2A, Z7.T1F.T2C.Y1D.Y2B, Z7.T1F.T2C.Y1D.Y2C, Z7.T1F.T2C.Y1D.Y2D, Z7.T1F.T2C.Y1E.Y2A, Z7.T1F.T2C.Y1E.Y2B, Z7.T1F.T2C.Y1E.Y2C, Z7.T1F.T2C.Y1E.Y2D, Z7.T1G.T2A.Y1A.Y2A, Z7.T1G.T2A.Y1A.Y2B, Z7.T1G.T2A.Y1A.Y2C, Z7.T1G.T2A.Y1A.Y2D, Z7.T1G.T2A.Y1B.Y2A, Z7.T1G.T2A.Y1B.Y2B, Z7.T1G.T2A.Y1B.Y2C, Z7.T1G.T2A.Y1B.Y2D, Z7.T1G.T2A.Y1C.Y2A, Z7.T1G.T2A.Y1C.Y2B, Z7.T1G.T2A.Y1C.Y2C, Z7.T1G.T2A.Y1C.Y2D, Z7.T1G.T2A.Y1D.Y2A, Z7.T1G.T2A.Y1D.Y2B, Z7.T1G.T2A.Y1D.Y2C, Z7.T1G.T2A.Y1D.Y2D, Z7.T1G.T2A.Y1E.Y2A, Z7.T1G.T2A.Y1E.Y2B, Z7.T1G.T2A.Y1E.Y2C, Z7.T1G.T2A.Y1E.Y2D, Z7.T1G.T2B.Y1A.Y2A, Z7.T1G.T2B.Y1A.Y2B, Z7.T1G.T2B.Y1A.Y2C, Z7.T1G.T2B.Y1A.Y2D, Z7.T1G.T2B.Y1B.Y2A, Z7.T1G.T2B.Y1B.Y2B, Z7.T1G.T2B.Y1B.Y2C, Z7.T1G.T2B.Y1B.Y2D, Z7.T1G.T2B.Y1C.Y2A, Z7.T1G.T2B.Y1C.Y2B, Z7.T1G.T2B.Y1C.Y2C, Z7.T1G.T2B.Y1C.Y2D, Z7.T1G.T2B.Y1D.Y2A, Z7.T1G.T2B.Y1D.Y2B, Z7.T1G.T2B.Y1D.Y2C, Z7.T1G.T2B.Y1D.Y2D, Z7.T1G.T2B.Y1E.Y2A, Z7.T1G.T2B.Y1E.Y2B, Z7.T1G.T2B.Y1E.Y2C, Z7.T1G.T2B.Y1E.Y2D, Z7.T1G.T2C.Y1A.Y2A, Z7.T1G.T2C.Y1A.Y2B, Z7.T1G.T2C.Y1A.Y2C, Z7.T1G.T2C.Y1A.Y2D, Z7.T1G.T2C.Y1B.Y2A, Z7.T1G.T2C.Y1B.Y2B, Z7.T1G.T2C.Y1B.Y2C, Z7.T1G.T2C.Y1B.Y2D, Z7.T1G.T2C.Y1C.Y2A, Z7.T1G.T2C.Y1C.Y2B, Z7.T1G.T2C.Y1C.Y2C, Z7.T1G.T2C.Y1C.Y2D, Z7.T1G.T2C.Y1D.Y2A, Z7.T1G.T2C.Y1D.Y2B, Z7.T1G.T2C.Y1D.Y2C, Z7.T1G.T2C.Y1D.Y2D, Z7.T1G.T2C.Y1E.Y2A, Z7.T1G.T2C.Y1E.Y2B, Z7.T1G.T2C.Y1E.Y2C, Z7.T1G.T2C.Y1E.Y2D,
なお別の実施形態において、選択された式Iの化合物は、以下で、一般式V(下記)の化合物として表の形式(表12)で命名される:
1a.2a.3a.4a.5a, 1a.2a.3a.4a.5b, 1a.2a.3a.4a.5d, 1a.2a.3a.4a.5f, 1a.2a.3a.4a.5h, 1a.2a.3a.4a.5i, 1a.2a.3a.4a.5n, 1a.2a.3a.4b.5a, 1a.2a.3a.4b.5b, 1a.2a.3a.4b.5d, 1a.2a.3a.4b.5f, 1a.2a.3a.4b.5h, 1a.2a.3a.4b.5i, 1a.2a.3a.4b.5n, 1a.2a.3a.4d.5a, 1a.2a.3a.4d.5b, 1a.2a.3a.4d.5d, 1a.2a.3a.4d.5f, 1a.2a.3a.4d.5h, 1a.2a.3a.4d.5i, 1a.2a.3a.4d.5n, 1a.2a.3a.4f.5a, 1a.2a.3a.4f.5b, 1a.2a.3a.4f.5d, 1a.2a.3a.4f.5f, 1a.2a.3a.4f.5h, 1a.2a.3a.4f.5i, 1a.2a.3a.4f.5n, 1a.2a.3a.4i.5a, 1a.2a.3a.4i.5b, 1a.2a.3a.4i.5d, 1a.2a.3a.4i.5f, 1a.2a.3a.4i.5h, 1a.2a.3a.4i.5i, 1a.2a.3a.4i.5n, 1a.2a.3a.4n.5a, 1a.2a.3a.4n.5b, 1a.2a.3a.4n.5d, 1a.2a.3a.4n.5f, 1a.2a.3a.4n.5h, 1a.2a.3a.4n.5i, 1a.2a.3a.4n.5n, 1a.2a.3a.4p.5a, 1a.2a.3a.4p.5b, 1a.2a.3a.4p.5d, 1a.2a.3a.4p.5f, 1a.2a.3a.4p.5h, 1a.2a.3a.4p.5i, 1a.2a.3a.4p.5n, 1a.2a.3c.4a.5a, 1a.2a.3c.4a.5b, 1a.2a.3c.4a.5d, 1a.2a.3c.4a.5f, 1a.2a.3c.4a.5h, 1a.2a.3c.4a.5i, 1a.2a.3c.4a.5n, 1a.2a.3c.4b.5a, 1a.2a.3c.4b.5b, 1a.2a.3c.4b.5d, 1a.2a.3c.4b.5f, 1a.2a.3c.4b.5h, 1a.2a.3c.4b.5i, 1a.2a.3c.4b.5n, 1a.2a.3c.4d.5a, 1a.2a.3c.4d.5b, 1a.2a.3c.4d.5d, 1a.2a.3c.4d.5f, 1a.2a.3c.4d.5h, 1a.2a.3c.4d.5i, 1a.2a.3c.4d.5n, 1a.2a.3c.4f.5a, 1a.2a.3c.4f.5b, 1a.2a.3c.4f.5d, 1a.2a.3c.4f.5f, 1a.2a.3c.4f.5h, 1a.2a.3c.4f.5i, 1a.2a.3c.4f.5n, 1a.2a.3c.4i.5a, 1a.2a.3c.4i.5b, 1a.2a.3c.4i.5d, 1a.2a.3c.4i.5f, 1a.2a.3c.4i.5h, 1a.2a.3c.4i.5i, 1a.2a.3c.4i.5n, 1a.2a.3c.4n.5a, 1a.2a.3c.4n.5b, 1a.2a.3c.4n.5d, 1a.2a.3c.4n.5f, 1a.2a.3c.4n.5h, 1a.2a.3c.4n.5i, 1a.2a.3c.4n.5n, 1a.2a.3c.4p.5a, 1a.2a.3c.4p.5b, 1a.2a.3c.4p.5d, 1a.2a.3c.4p.5f, 1a.2a.3c.4p.5h, 1a.2a.3c.4p.5i, 1a.2a.3c.4p.5n, 1a.2a.3e.4a.5a, 1a.2a.3e.4a.5b, 1a.2a.3e.4a.5d, 1a.2a.3e.4a.5f, 1a.2a.3e.4a.5h, 1a.2a.3e.4a.5i, 1a.2a.3e.4a.5n, 1a.2a.3e.4b.5a, 1a.2a.3e.4b.5b, 1a.2a.3e.4b.5d, 1a.2a.3e.4b.5f, 1a.2a.3e.4b.5h, 1a.2a.3e.4b.5i, 1a.2a.3e.4b.5n, 1a.2a.3e.4d.5a, 1a.2a.3e.4d.5b, 1a.2a.3e.4d.5d, 1a.2a.3e.4d.5f, 1a.2a.3e.4d.5h, 1a.2a.3e.4d.5i, 1a.2a.3e.4d.5n, 1a.2a.3e.4f.5a, 1a.2a.3e.4f.5b, 1a.2a.3e.4f.5d, 1a.2a.3e.4f.5f, 1a.2a.3e.4f.5h, 1a.2a.3e.4f.5i, 1a.2a.3e.4f.5n, 1a.2a.3e.4i.5a, 1a.2a.3e.4i.5b, 1a.2a.3e.4i.5d, 1a.2a.3e.4i.5f, 1a.2a.3e.4i.5h, 1a.2a.3e.4i.5i, 1a.2a.3e.4i.5n, 1a.2a.3e.4n.5a, 1a.2a.3e.4n.5b, 1a.2a.3e.4n.5d, 1a.2a.3e.4n.5f, 1a.2a.3e.4n.5h, 1a.2a.3e.4n.5i, 1a.2a.3e.4n.5n, 1a.2a.3e.4p.5a, 1a.2a.3e.4p.5b, 1a.2a.3e.4p.5d, 1a.2a.3e.4p.5f, 1a.2a.3e.4p.5h, 1a.2a.3e.4p.5i, 1a.2a.3e.4p.5n, 1a.2a.3g.4a.5a, 1a.2a.3g.4a.5b, 1a.2a.3g.4a.5d, 1a.2a.3g.4a.5f, 1a.2a.3g.4a.5h, 1a.2a.3g.4a.5i, 1a.2a.3g.4a.5n, 1a.2a.3g.4b.5a, 1a.2a.3g.4b.5b, 1a.2a.3g.4b.5d, 1a.2a.3g.4b.5f, 1a.2a.3g.4b.5h, 1a.2a.3g.4b.5i, 1a.2a.3g.4b.5n, 1a.2a.3g.4d.5a, 1a.2a.3g.4d.5b, 1a.2a.3g.4d.5d, 1a.2a.3g.4d.5f, 1a.2a.3g.4d.5h, 1a.2a.3g.4d.5i, 1a.2a.3g.4d.5n, 1a.2a.3g.4f.5a, 1a.2a.3g.4f.5b, 1a.2a.3g.4f.5d, 1a.2a.3g.4f.5f, 1a.2a.3g.4f.5h, 1a.2a.3g.4f.5i, 1a.2a.3g.4f.5n, 1a.2a.3g.4i.5a, 1a.2a.3g.4i.5b, 1a.2a.3g.4i.5d, 1a.2a.3g.4i.5f, 1a.2a.3g.4i.5h, 1a.2a.3g.4i.5i, 1a.2a.3g.4i.5n, 1a.2a.3g.4n.5a, 1a.2a.3g.4n.5b, 1a.2a.3g.4n.5d, 1a.2a.3g.4n.5f, 1a.2a.3g.4n.5h, 1a.2a.3g.4n.5i, 1a.2a.3g.4n.5n, 1a.2a.3g.4p.5a, 1a.2a.3g.4p.5b, 1a.2a.3g.4p.5d, 1a.2a.3g.4p.5f, 1a.2a.3g.4p.5h, 1a.2a.3g.4p.5i, 1a.2a.3g.4p.5n, 1a.2b.3a.4a.5a, 1a.2b.3a.4a.5b, 1a.2b.3a.4a.5d, 1a.2b.3a.4a.5f, 1a.2b.3a.4a.5h, 1a.2b.3a.4a.5i, 1a.2b.3a.4a.5n, 1a.2b.3a.4b.5a, 1a.2b.3a.4b.5b, 1a.2b.3a.4b.5d, 1a.2b.3a.4b.5f, 1a.2b.3a.4b.5h, 1a.2b.3a.4b.5i, 1a.2b.3a.4b.5n, 1a.2b.3a.4d.5a, 1a.2b.3a.4d.5b, 1a.2b.3a.4d.5d, 1a.2b.3a.4d.5f, 1a.2b.3a.4d.5h, 1a.2b.3a.4d.5i, 1a.2b.3a.4d.5n, 1a.2b.3a.4f.5a, 1a.2b.3a.4f.5b, 1a.2b.3a.4f.5d, 1a.2b.3a.4f.5f, 1a.2b.3a.4f.5h, 1a.2b.3a.4f.5i, 1a.2b.3a.4f.5n, 1a.2b.3a.4i.5a, 1a.2b.3a.4i.5b, 1a.2b.3a.4i.5d, 1a.2b.3a.4i.5f, 1a.2b.3a.4i.5h, 1a.2b.3a.4i.5i, 1a.2b.3a.4i.5n, 1a.2b.3a.4n.5a, 1a.2b.3a.4n.5b, 1a.2b.3a.4n.5d, 1a.2b.3a.4n.5f, 1a.2b.3a.4n.5h, 1a.2b.3a.4n.5i, 1a.2b.3a.4n.5n, 1a.2b.3a.4p.5a, 1a.2b.3a.4p.5b, 1a.2b.3a.4p.5d, 1a.2b.3a.4p.5f, 1a.2b.3a.4p.5h, 1a.2b.3a.4p.5i, 1a.2b.3a.4p.5n, 1a.2b.3c.4a.5a, 1a.2b.3c.4a.5b, 1a.2b.3c.4a.5d, 1a.2b.3c.4a.5f, 1a.2b.3c.4a.5h, 1a.2b.3c.4a.5i, 1a.2b.3c.4a.5n, 1a.2b.3c.4b.5a, 1a.2b.3c.4b.5b, 1a.2b.3c.4b.5d, 1a.2b.3c.4b.5f, 1a.2b.3c.4b.5h, 1a.2b.3c.4b.5i, 1a.2b.3c.4b.5n, 1a.2b.3c.4d.5a, 1a.2b.3c.4d.5b, 1a.2b.3c.4d.5d, 1a.2b.3c.4d.5f, 1a.2b.3c.4d.5h, 1a.2b.3c.4d.5i, 1a.2b.3c.4d.5n, 1a.2b.3c.4f.5a, 1a.2b.3c.4f.5b, 1a.2b.3c.4f.5d, 1a.2b.3c.4f.5f, 1a.2b.3c.4f.5h, 1a.2b.3c.4f.5i, 1a.2b.3c.4f.5n, 1a.2b.3c.4i.5a, 1a.2b.3c.4i.5b, 1a.2b.3c.4i.5d, 1a.2b.3c.4i.5f, 1a.2b.3c.4i.5h, 1a.2b.3c.4i.5i, 1a.2b.3c.4i.5n, 1a.2b.3c.4n.5a, 1a.2b.3c.4n.5b, 1a.2b.3c.4n.5d, 1a.2b.3c.4n.5f, 1a.2b.3c.4n.5h, 1a.2b.3c.4n.5i, 1a.2b.3c.4n.5n, 1a.2b.3c.4p.5a, 1a.2b.3c.4p.5b, 1a.2b.3c.4p.5d, 1a.2b.3c.4p.5f, 1a.2b.3c.4p.5h, 1a.2b.3c.4p.5i, 1a.2b.3c.4p.5n, 1a.2b.3e.4a.5a, 1a.2b.3e.4a.5b, 1a.2b.3e.4a.5d, 1a.2b.3e.4a.5f, 1a.2b.3e.4a.5h, 1a.2b.3e.4a.5i, 1a.2b.3e.4a.5n, 1a.2b.3e.4b.5a, 1a.2b.3e.4b.5b, 1a.2b.3e.4b.5d, 1a.2b.3e.4b.5f, 1a.2b.3e.4b.5h, 1a.2b.3e.4b.5i, 1a.2b.3e.4b.5n, 1a.2b.3e.4d.5a, 1a.2b.3e.4d.5b, 1a.2b.3e.4d.5d, 1a.2b.3e.4d.5f, 1a.2b.3e.4d.5h, 1a.2b.3e.4d.5i, 1a.2b.3e.4d.5n, 1a.2b.3e.4f.5a, 1a.2b.3e.4f.5b, 1a.2b.3e.4f.5d, 1a.2b.3e.4f.5f, 1a.2b.3e.4f.5h,
1a.2b.3e.4f.5i, 1a.2b.3e.4f.5n, 1a.2b.3e.4i.5a, 1a.2b.3e.4i.5b, 1a.2b.3e.4i.5d, 1a.2b.3e.4i.5f, 1a.2b.3e.4i.5h, 1a.2b.3e.4i.5i, 1a.2b.3e.4i.5n, 1a.2b.3e.4n.5a, 1a.2b.3e.4n.5b, 1a.2b.3e.4n.5d, 1a.2b.3e.4n.5f, 1a.2b.3e.4n.5h, 1a.2b.3e.4n.5i, 1a.2b.3e.4n.5n, 1a.2b.3e.4p.5a, 1a.2b.3e.4p.5b, 1a.2b.3e.4p.5d, 1a.2b.3e.4p.5f, 1a.2b.3e.4p.5h, 1a.2b.3e.4p.5i, 1a.2b.3e.4p.5n, 1a.2b.3g.4a.5a, 1a.2b.3g.4a.5b, 1a.2b.3g.4a.5d, 1a.2b.3g.4a.5f, 1a.2b.3g.4a.5h, 1a.2b.3g.4a.5i, 1a.2b.3g.4a.5n, 1a.2b.3g.4b.5a, 1a.2b.3g.4b.5b, 1a.2b.3g.4b.5d, 1a.2b.3g.4b.5f, 1a.2b.3g.4b.5h, 1a.2b.3g.4b.5i, 1a.2b.3g.4b.5n, 1a.2b.3g.4d.5a, 1a.2b.3g.4d.5b, 1a.2b.3g.4d.5d, 1a.2b.3g.4d.5f, 1a.2b.3g.4d.5h, 1a.2b.3g.4d.5i, 1a.2b.3g.4d.5n, 1a.2b.3g.4f.5a, 1a.2b.3g.4f.5b, 1a.2b.3g.4f.5d, 1a.2b.3g.4f.5f, 1a.2b.3g.4f.5h, 1a.2b.3g.4f.5i, 1a.2b.3g.4f.5n, 1a.2b.3g.4i.5a, 1a.2b.3g.4i.5b, 1a.2b.3g.4i.5d, 1a.2b.3g.4i.5f, 1a.2b.3g.4i.5h, 1a.2b.3g.4i.5i, 1a.2b.3g.4i.5n, 1a.2b.3g.4n.5a, 1a.2b.3g.4n.5b, 1a.2b.3g.4n.5d, 1a.2b.3g.4n.5f, 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1d.2y.3c.4d.5i, 1d.2y.3c.4d.5n, 1d.2y.3c.4f.5a, 1d.2y.3c.4f.5b, 1d.2y.3c.4f.5d, 1d.2y.3c.4f.5f, 1d.2y.3c.4f.5h, 1d.2y.3c.4f.5i, 1d.2y.3c.4f.5n, 1d.2y.3c.4i.5a, 1d.2y.3c.4i.5b, 1d.2y.3c.4i.5d, 1d.2y.3c.4i.5f, 1d.2y.3c.4i.5h, 1d.2y.3c.4i.5i, 1d.2y.3c.4i.5n, 1d.2y.3c.4n.5a, 1d.2y.3c.4n.5b, 1d.2y.3c.4n.5d, 1d.2y.3c.4n.5f, 1d.2y.3c.4n.5h, 1d.2y.3c.4n.5i, 1d.2y.3c.4n.5n, 1d.2y.3c.4p.5a, 1d.2y.3c.4p.5b, 1d.2y.3c.4p.5d, 1d.2y.3c.4p.5f, 1d.2y.3c.4p.5h, 1d.2y.3c.4p.5i, 1d.2y.3c.4p.5n, 1d.2y.3e.4a.5a, 1d.2y.3e.4a.5b, 1d.2y.3e.4a.5d, 1d.2y.3e.4a.5f, 1d.2y.3e.4a.5h, 1d.2y.3e.4a.5i, 1d.2y.3e.4a.5n, 1d.2y.3e.4b.5a, 1d.2y.3e.4b.5b, 1d.2y.3e.4b.5d, 1d.2y.3e.4b.5f, 1d.2y.3e.4b.5h, 1d.2y.3e.4b.5i, 1d.2y.3e.4b.5n, 1d.2y.3e.4d.5a, 1d.2y.3e.4d.5b, 1d.2y.3e.4d.5d, 1d.2y.3e.4d.5f, 1d.2y.3e.4d.5h, 1d.2y.3e.4d.5i, 1d.2y.3e.4d.5n, 1d.2y.3e.4f.5a, 1d.2y.3e.4f.5b, 1d.2y.3e.4f.5d, 1d.2y.3e.4f.5f, 1d.2y.3e.4f.5h, 1d.2y.3e.4f.5i, 1d.2y.3e.4f.5n, 1d.2y.3e.4i.5a, 1d.2y.3e.4i.5b, 1d.2y.3e.4i.5d, 1d.2y.3e.4i.5f, 1d.2y.3e.4i.5h, 1d.2y.3e.4i.5i, 1d.2y.3e.4i.5n, 1d.2y.3e.4n.5a, 1d.2y.3e.4n.5b, 1d.2y.3e.4n.5d, 1d.2y.3e.4n.5f, 1d.2y.3e.4n.5h, 1d.2y.3e.4n.5i, 1d.2y.3e.4n.5n, 1d.2y.3e.4p.5a, 1d.2y.3e.4p.5b, 1d.2y.3e.4p.5d, 1d.2y.3e.4p.5f, 1d.2y.3e.4p.5h, 1d.2y.3e.4p.5i, 1d.2y.3e.4p.5n, 1d.2y.3g.4a.5a, 1d.2y.3g.4a.5b, 1d.2y.3g.4a.5d, 1d.2y.3g.4a.5f, 1d.2y.3g.4a.5h, 1d.2y.3g.4a.5i, 1d.2y.3g.4a.5n, 1d.2y.3g.4b.5a, 1d.2y.3g.4b.5b, 1d.2y.3g.4b.5d, 1d.2y.3g.4b.5f, 1d.2y.3g.4b.5h, 1d.2y.3g.4b.5i, 1d.2y.3g.4b.5n, 1d.2y.3g.4d.5a, 1d.2y.3g.4d.5b, 1d.2y.3g.4d.5d, 1d.2y.3g.4d.5f, 1d.2y.3g.4d.5h, 1d.2y.3g.4d.5i, 1d.2y.3g.4d.5n, 1d.2y.3g.4f.5a, 1d.2y.3g.4f.5b, 1d.2y.3g.4f.5d, 1d.2y.3g.4f.5f, 1d.2y.3g.4f.5h, 1d.2y.3g.4f.5i, 1d.2y.3g.4f.5n, 1d.2y.3g.4i.5a, 1d.2y.3g.4i.5b, 1d.2y.3g.4i.5d, 1d.2y.3g.4i.5f, 1d.2y.3g.4i.5h, 1d.2y.3g.4i.5i, 1d.2y.3g.4i.5n, 1d.2y.3g.4n.5a, 1d.2y.3g.4n.5b, 1d.2y.3g.4n.5d, 1d.2y.3g.4n.5f, 1d.2y.3g.4n.5h, 1d.2y.3g.4n.5i, 1d.2y.3g.4n.5n, 1d.2y.3g.4p.5a, 1d.2y.3g.4p.5b, 1d.2y.3g.4p.5d, 1d.2y.3g.4p.5f, 1d.2y.3g.4p.5h, 1d.2y.3g.4p.5i, 1d.2y.3g.4p.5n, 1d.2z.3a.4a.5a, 1d.2z.3a.4a.5b, 1d.2z.3a.4a.5d, 1d.2z.3a.4a.5f, 1d.2z.3a.4a.5h, 1d.2z.3a.4a.5i, 1d.2z.3a.4a.5n, 1d.2z.3a.4b.5a, 1d.2z.3a.4b.5b, 1d.2z.3a.4b.5d, 1d.2z.3a.4b.5f, 1d.2z.3a.4b.5h, 1d.2z.3a.4b.5i, 1d.2z.3a.4b.5n, 1d.2z.3a.4d.5a, 1d.2z.3a.4d.5b, 1d.2z.3a.4d.5d, 1d.2z.3a.4d.5f, 1d.2z.3a.4d.5h, 1d.2z.3a.4d.5i, 1d.2z.3a.4d.5n, 1d.2z.3a.4f.5a, 1d.2z.3a.4f.5b, 1d.2z.3a.4f.5d, 1d.2z.3a.4f.5f, 1d.2z.3a.4f.5h, 1d.2z.3a.4f.5i, 1d.2z.3a.4f.5n, 1d.2z.3a.4i.5a, 1d.2z.3a.4i.5b, 1d.2z.3a.4i.5d, 1d.2z.3a.4i.5f, 1d.2z.3a.4i.5h, 1d.2z.3a.4i.5i, 1d.2z.3a.4i.5n, 1d.2z.3a.4n.5a, 1d.2z.3a.4n.5b, 1d.2z.3a.4n.5d, 1d.2z.3a.4n.5f, 1d.2z.3a.4n.5h, 1d.2z.3a.4n.5i, 1d.2z.3a.4n.5n, 1d.2z.3a.4p.5a, 1d.2z.3a.4p.5b, 1d.2z.3a.4p.5d, 1d.2z.3a.4p.5f, 1d.2z.3a.4p.5h, 1d.2z.3a.4p.5i, 1d.2z.3a.4p.5n, 1d.2z.3c.4a.5a, 1d.2z.3c.4a.5b, 1d.2z.3c.4a.5d, 1d.2z.3c.4a.5f, 1d.2z.3c.4a.5h, 1d.2z.3c.4a.5i, 1d.2z.3c.4a.5n, 1d.2z.3c.4b.5a, 1d.2z.3c.4b.5b, 1d.2z.3c.4b.5d, 1d.2z.3c.4b.5f, 1d.2z.3c.4b.5h, 1d.2z.3c.4b.5i, 1d.2z.3c.4b.5n, 1d.2z.3c.4d.5a, 1d.2z.3c.4d.5b, 1d.2z.3c.4d.5d, 1d.2z.3c.4d.5f, 1d.2z.3c.4d.5h,
1d.2z.3c.4d.5i, 1d.2z.3c.4d.5n, 1d.2z.3c.4f.5a, 1d.2z.3c.4f.5b, 1d.2z.3c.4f.5d, 1d.2z.3c.4f.5f, 1d.2z.3c.4f.5h, 1d.2z.3c.4f.5i, 1d.2z.3c.4f.5n, 1d.2z.3c.4i.5a, 1d.2z.3c.4i.5b, 1d.2z.3c.4i.5d, 1d.2z.3c.4i.5f, 1d.2z.3c.4i.5h, 1d.2z.3c.4i.5i, 1d.2z.3c.4i.5n, 1d.2z.3c.4n.5a, 1d.2z.3c.4n.5b, 1d.2z.3c.4n.5d, 1d.2z.3c.4n.5f, 1d.2z.3c.4n.5h, 1d.2z.3c.4n.5i, 1d.2z.3c.4n.5n, 1d.2z.3c.4p.5a, 1d.2z.3c.4p.5b, 1d.2z.3c.4p.5d, 1d.2z.3c.4p.5f, 1d.2z.3c.4p.5h, 1d.2z.3c.4p.5i, 1d.2z.3c.4p.5n, 1d.2z.3e.4a.5a, 1d.2z.3e.4a.5b, 1d.2z.3e.4a.5d, 1d.2z.3e.4a.5f, 1d.2z.3e.4a.5h, 1d.2z.3e.4a.5i, 1d.2z.3e.4a.5n, 1d.2z.3e.4b.5a, 1d.2z.3e.4b.5b, 1d.2z.3e.4b.5d, 1d.2z.3e.4b.5f, 1d.2z.3e.4b.5h, 1d.2z.3e.4b.5i, 1d.2z.3e.4b.5n, 1d.2z.3e.4d.5a, 1d.2z.3e.4d.5b, 1d.2z.3e.4d.5d, 1d.2z.3e.4d.5f, 1d.2z.3e.4d.5h, 1d.2z.3e.4d.5i, 1d.2z.3e.4d.5n, 1d.2z.3e.4f.5a, 1d.2z.3e.4f.5b, 1d.2z.3e.4f.5d, 1d.2z.3e.4f.5f, 1d.2z.3e.4f.5h, 1d.2z.3e.4f.5i, 1d.2z.3e.4f.5n, 1d.2z.3e.4i.5a, 1d.2z.3e.4i.5b, 1d.2z.3e.4i.5d, 1d.2z.3e.4i.5f, 1d.2z.3e.4i.5h, 1d.2z.3e.4i.5i, 1d.2z.3e.4i.5n, 1d.2z.3e.4n.5a, 1d.2z.3e.4n.5b, 1d.2z.3e.4n.5d, 1d.2z.3e.4n.5f, 1d.2z.3e.4n.5h, 1d.2z.3e.4n.5i, 1d.2z.3e.4n.5n, 1d.2z.3e.4p.5a, 1d.2z.3e.4p.5b, 1d.2z.3e.4p.5d, 1d.2z.3e.4p.5f, 1d.2z.3e.4p.5h, 1d.2z.3e.4p.5i, 1d.2z.3e.4p.5n, 1d.2z.3g.4a.5a, 1d.2z.3g.4a.5b, 1d.2z.3g.4a.5d, 1d.2z.3g.4a.5f, 1d.2z.3g.4a.5h, 1d.2z.3g.4a.5i, 1d.2z.3g.4a.5n, 1d.2z.3g.4b.5a, 1d.2z.3g.4b.5b, 1d.2z.3g.4b.5d, 1d.2z.3g.4b.5f, 1d.2z.3g.4b.5h, 1d.2z.3g.4b.5i, 1d.2z.3g.4b.5n, 1d.2z.3g.4d.5a, 1d.2z.3g.4d.5b, 1d.2z.3g.4d.5d, 1d.2z.3g.4d.5f, 1d.2z.3g.4d.5h, 1d.2z.3g.4d.5i, 1d.2z.3g.4d.5n, 1d.2z.3g.4f.5a, 1d.2z.3g.4f.5b, 1d.2z.3g.4f.5d, 1d.2z.3g.4f.5f, 1d.2z.3g.4f.5h, 1d.2z.3g.4f.5i, 1d.2z.3g.4f.5n, 1d.2z.3g.4i.5a, 1d.2z.3g.4i.5b, 1d.2z.3g.4i.5d, 1d.2z.3g.4i.5f, 1d.2z.3g.4i.5h, 1d.2z.3g.4i.5i, 1d.2z.3g.4i.5n, 1d.2z.3g.4n.5a, 1d.2z.3g.4n.5b, 1d.2z.3g.4n.5d, 1d.2z.3g.4n.5f, 1d.2z.3g.4n.5h, 1d.2z.3g.4n.5i, 1d.2z.3g.4n.5n, 1d.2z.3g.4p.5a, 1d.2z.3g.4p.5b, 1d.2z.3g.4p.5d, 1d.2z.3g.4p.5f, 1d.2z.3g.4p.5h, 1d.2z.3g.4p.5i, 1d.2z.3g.4p.5n
なおさらに別の実施形態において、本発明の化合物は、約2000nM未満、約1500nM未満、約1000nM未満、約900nM未満、約800nM未満、約700nM未満、約650nM未満、約600nM未満、約550nM未満、約500nM未満、約400nM未満、約350nM未満、約300nM未満、約250nM未満、約200nM未満、約100nM、または約50nM未満のIC50により表されるような化合物の阻害活性に等しいかまたはより高いレベルでの、P450に対する阻害活性を有する。
本発明の化合物は、従来のキャリアおよび賦形剤と一緒に処方され、これらのキャリアおよび賦形剤は、通常の実施に一致するように選択される。錠剤は、賦形剤、グライダント、充填剤、結合剤などを含有する。水性処方物は、滅菌形態で調製され、そして経口投与以外による送達が意図される場合には一般に、等張性である。全ての処方物は、Handbook of Pharmaceutical Excipients(1986)(その全体が本明細書中に参考として援用される)に記載されるもののような賦形剤を必要に応じて含有する。賦形剤としては、アスコルビン酸および他の酸化防止剤、キレート剤(例えば、EDTA)、炭水化物(例えば、デキストリン、ヒドロキシアルキルセルロース、ヒドロキシアルキルメチルセルロース)、ステアリン酸などが挙げられる。処方物のpHは、約3〜約11の範囲であるが、通常は、約7〜10である。
a)本発明の化合物、あるいはその薬学的に受容可能な塩、溶媒和物、またはエステルを含有する、第一の薬学的組成物;ならびに
b)HIVプロテアーゼ阻害化合物、HIVの逆トランスクリプターゼの非ヌクレオシドインヒビター、HIVの逆トランスクリプターゼのヌクレオシドインヒビター、HIVの逆トランスクリプターゼのヌクレオチドインヒビター、HIVインテグラーゼインヒビター、gp41インヒビター、CXCR4インヒビター、gp120インヒビター、CCR5インヒビター、インターフェロン、リバビリンアナログ、NS3プロテアーゼインヒビター、α−グルコシダーゼ1インヒビター、肝臓保護物質(hepatoprotectant)、HCVの非ヌクレオシドインヒビター、およびHCVを処置するための他の薬物、ならびにこれらの組み合わせからなる群より選択される少なくとも1種のさらなる治療剤を含有する、第二の薬学的組成物、
を含有する、組み合わせ薬学的薬剤を提供する。
本発明の1種以上の化合物(本明細書中で、活性成分と称される)は、処置されるべき状態のために適切な任意の経路により投与される。適切な経路としては、経口、直腸、経鼻、局所(頬および舌下が挙げられる)、膣および非経口(皮下、筋肉内、静脈内、皮内、鞘内および硬膜外)などが挙げられる。好ましい経路は、例えば、レシピエントの状態とともに変動し得ることが理解される。本発明の化合物の利点は、これらの化合物が経口で生体利用可能であり、経口投与され得ることである。
1つの実施形態において、本発明の化合物は、例えば、シトクロムP450モノオキシゲナーゼを阻害するために、単独で使用され得る。別の実施形態において、本発明の化合物は、他の活性な治療成分または薬剤と組み合わせて使用される。好ましくは、他の活性な治療成分または薬剤は、シトクロムP450酵素(例えば、モノオキシゲナーゼ酵素であり、例えば、1A2、2B6、2C8、2C19、2C9、2D6、2E1、3A4、5、7など)により代謝されるか、またはこの酵素による酸化代謝を受けやすい。
化合物1(10mmol)を10mLの無水DMFに溶解した。得られた溶液に重炭酸カリウム(20mmol)を一度に添加した。ヨウ化メチル(12mmol)を滴下し、その後、この反応混合物を12時間攪拌した。次いで、この反応混合物を酢酸エチルで希釈し、そして飽和塩化ナトリウム水溶液で2回洗浄した。得られた有機抽出物を無水硫酸ナトリウムで乾燥させ、減圧下で濃縮し、そして高真空下で乾燥させて、化合物2(2.9g)を得た。
THF中1Mの水素化アルミニウムリチウム(10mmol)を窒素ガス下で攪拌し、そして氷浴中で冷却した。化合物2(10mmol)を10mLの無水THFに溶解し、そしてこの冷LiAlH4溶液に60分間かけて滴下した。添加が完了したら、この反応混合物を同じ温度でさらに60分〜90分間攪拌した。メタノール(3mL)をゆっくりと添加して、この反応をクエンチした。次いで、重炭酸ナトリウム(3g)、続いて酒石酸カリウムナトリウムの飽和水溶液、次いで酢酸エチルを添加した。この混合物を30分間攪拌した。その有機抽出物を収集および抽出し、そしてその水相をさらなる酢酸エチルで再度抽出した。次いで、合わせた有機抽出物を重炭酸ナトリウム水溶液で2回洗浄し、続いて塩化ナトリウム飽和水溶液で洗浄した。次いで、その有機相を無水硫酸ナトリウムで乾燥させ、次いで、減圧下で濃縮した。得られた油状物を高真空下で乾燥させて、固体の化合物3(2.6g)を得た。
化合物3(3.9mmol)を無水DMSO(13mL)に溶解した。この溶液を窒素ガス下5℃〜10℃で攪拌した。次いで、トリエチルアミン(13.7mmol)を添加し、続いて三酸化硫黄ピリジン錯体(14.8mmol)を添加した。この反応混合物を60分〜90分間攪拌した。氷を添加し、そしてこの反応混合物を10分間攪拌した。重炭酸ナトリウム飽和水溶液を添加し、そしてこの混合物を酢酸エチルで抽出した。次いで、その有機相を重炭酸ナトリウム飽和水溶液で洗浄し、続いて水で洗浄し、最後に、塩化ナトリウム飽和水溶液で洗浄した。その有機相を無水硫酸ナトリウムで乾燥させ、次いで、減圧下で濃縮した。
化合物3を無水ジクロロメタン(5mL)に溶解し、そして氷浴中窒素下で攪拌した。次いで、ピリジン(3mmol)を添加した。次いで、この反応混合物に無水ジクロロメタン(1mL)中のメタンスルホニルクロリド(1.2mmol)を滴下した。この反応混合物を1時間攪拌し、次いで、氷浴から除いた。この反応混合物を室温で2時間〜3時間攪拌し、ジクロロメタンで希釈し、そして5%クエン酸水溶液で2回洗浄し、続いて水で2回洗浄した。その有機相を無水硫酸ナトリウムで乾燥させ、次いで、減圧下で濃縮し、そして高真空下で乾燥させて、固体の化合物5(312mg)を得た。
化合物5(0.91mmol)を無水DMF(5mL)に溶解し、イソブチルアミン(45.4mmol)を添加し、そしてこの混合物を室温で12時間攪拌した。過剰のイソブチルアミンを減圧下で除去した。得られた物質を酢酸エチルで希釈し、そして重炭酸ナトリウム飽和水溶液で2回洗浄し、続いて塩化ナトリウム飽和水溶液で洗浄し、その有機相を無水硫酸ナトリウムで乾燥させ、濾過し、次いで減圧下で濃縮した。得られた粗製物質を高真空下で乾燥させて、固体の化合物6a(293mg)を得た。
化合物5(0.5mmol)を無水DMF(5mL)に溶解し、4−クロロベンジルアミン(2.5mmol)を添加し、そしてこの反応混合物を16時間攪拌した。次いで、この混合物を酢酸エチルで希釈し、そして飽和塩化ナトリウム水溶液で2回洗浄した。その有機層を水と混合し、そして5%クエン酸水溶液を添加して、7〜8のpHを得た。その有機層を収集し、そして塩化ナトリウム飽和水溶液で洗浄し、無水硫酸ナトリウムで乾燥させ、次いで、減圧下で濃縮した。その粗製生成物をフラッシュシリカゲルカラムクロマトグラフィー(DCM中0%〜10%のMeOH)で精製して、化合物6b(約100mg)を得た。
化合物5(1mmol)を無水DMF(10mL)に溶解し、次いで、2−クロロベンジルアミン(5mmol)を添加し、そしてこの混合物を室温で20時間攪拌した。この反応混合物を40℃でさらに48時間攪拌し、酢酸エチルで希釈し、塩化ナトリウム飽和水溶液で2回洗浄し、次いで、塩化ナトリウム飽和水溶液で洗浄した。その有機層を無水硫酸ナトリウムで乾燥させ、次いで、減圧下で濃縮した。その粗製生成物をフラッシュシリカゲルカラムクロマトグラフィー(DCM中0%〜10%のMeOH)で精製して、化合物6c(約210mg)を得た。
化合物8(Molekulaから市販により得た)(17mmol)のDCM(40mL)中の溶液に、化合物7(19mmol;Sigma−Aldrichから購入した)を添加し、続いてトリエチルアミン(26mmol)を添加した。得られた反応混合物を12時間攪拌し、そして減圧下で濃縮した。この反応混合物をEtOAcで希釈し、そして飽和水性Na2CO3、水、およびブラインで順番に洗浄した。その溶媒を減圧下で除去した。フラッシュカラムクロマトグラフィー(シリカゲル,溶出液:ヘキサン/EtOAc=1/1)による残渣の精製により、化合物9(4.7g)を得た。
化合物11は、Aldrichから市販されており、受け取った状態で使用した。
化合物11(2.05g,11.3mmol)のCH2Cl2(40mL)中の懸濁物に、iPr2NEt(5.87mL,33.9mmol)を添加し、続いてCDI(カルボニルジイミダゾール;1.86g,11.3mmol)を添加した。得られた混合物を室温で6時間攪拌し、次いで、化合物10(2.33g,11.3mmol)を添加した。得られた混合物をさらに10時間攪拌し、その後、エバポレートにより乾固させた。この混合物をCH2Cl2に再溶解し、そしてその固体を濾過により除去した。その濾液をエバポレートにより乾固させ、そしてCombiFlash(20%〜80%のEtOAc/ヘキサンで溶出)により精製して、3.2gの化合物12を淡黄色油状物として得た。m/z 298.0(M+H)+。
化合物12(33g,112mmol)のエタノール(366mL)中の溶液に、0℃で、水酸化ナトリウム(4.7g,117mmol)の水(62mL)中の溶液を添加した。この混合物を25℃で1時間攪拌し、そして溶媒を減圧下で除去した。この混合物をエタノール(3×400mL)と一緒にエバポレートし、そして高真空下60℃で2時間乾燥させて、固体を得た。上記固体のDMF(180mL)中の溶液に、臭化ベンジル(16.2mL,136mmol)を添加した。この混合物を暗所で16時間攪拌し、そして水(300mL)でクエンチした。この混合物をEtOAc(4×300mL)で抽出した。合わせた有機相を水およびブラインで5回洗浄し、そしてNa2SO4で乾燥させた。濃縮により化合物13(48g)を得、これをさらに精製せずに次の工程において使用した。
化合物13(33g,74mmol)のDMSO(225mL)およびEt3N(36mL)中の混合物を30分間攪拌した。この混合物を0℃〜10℃まで冷却し、SO3−ピリジン(45g)を添加し、そして攪拌を60分間続けた。氷(300g)を添加し、そしてこの混合物を30分間攪拌した。EtOAc(300mL)を添加し、そしてpHが9〜10になるまで飽和Na2CO3を添加した。その有機相を水相から分離し、そしてその水相をEtOAc(2×300mL)で抽出した。合わせた有機相を飽和Na2CO3で2回洗浄し、水で3回洗浄し、次いでブラインで洗浄した。この混合物をNa2SO4で乾燥させ、そして濃縮して化合物14(32g)を得、これを、さらに精製せずに次の工程において直接使用した。
化合物14(32g)のCH3CN(325mL)中の溶液に、反応容器の周囲に水浴を置いてモルホリン(12.9mL,148mmol)を添加し、続いてHOAc(8.9mL,148mmol)およびNaBH(OAc)3(47g,222mmol)を添加した。この混合物を12時間攪拌した。CH3CNを減圧下で除去し、そしてこの混合物をEtOAc(300mL)で希釈した。pHが9〜10になるまで飽和Na2CO3を添加した。その有機相を水相から分離し、そしてその水相をEtOAc(2×300mL)で抽出した。合わせた有機相を飽和Na2CO3で2回洗浄し、続いて水で洗浄し、最後にブラインで洗浄した。この混合物をNa2SO4で乾燥させた。得られた残渣を濃縮し、そしてシリカゲルカラムクロマトグラフィー(EtOAc〜DCM/iPrOH=10/1)により精製して、化合物15(30g)を得た。
化合物15(26.5g,56mmol)のエタノール(160mL)中の溶液に、0℃で、水酸化ナトリウム(2.5g,62mmol)の水(30mL)中の溶液を添加した。この混合物を25℃で1時間攪拌し、そして溶媒を減圧下で除去した。この混合物を水(200mL)で希釈し、次いで、100mLのCH2Cl2で6回洗浄した。その水相を12NのHCl(5.2mL)で酸性化し、そして減圧下で乾燥させて、カルボン酸(22g)を得た。
化合物4、6a、6b、6cまたは7を無水DMF(5mL)に溶解した。化合物9(1.5〜5モル当量)を添加し、そしてこの混合物を3時間〜48時間攪拌した。次いで、この反応混合物を酢酸エチルで希釈し、そして重炭酸ナトリウム飽和水溶液で2回洗浄し、続いて飽和塩化ナトリウム水溶液で洗浄した。次いで、その有機相を無水硫酸ナトリウムで乾燥させ、そして減圧下で濃縮した。得られた濃縮物をフラッシュシリカゲルカラムクロマトグラフィー(ジクロロメタン中10%〜30%のEtOAc)により精製して、所望の生成物(すなわち、それぞれ化合物17、17a、17bまたは17c)を得た。
化合物17、17a、17bまたは17cをジオキサン中4NのHCl(5mL〜10mL)に溶解し、そして60分間〜90分間攪拌した。この反応混合物を減圧下で濃縮した。THFを添加し、そしてこの混合物を再度、減圧下で濃縮した。化合物12(1モル当量)を無水DMFに溶解し、そして濃縮した物質に添加した。1−ヒドロキシベンゾトリアゾール水和物(1.5モル当量)、およびN−(3−ジメチルアミノプロピル)−N’−エチルカルボジイミド塩酸塩(「EDC」;1.5モル当量)を添加し、そしてこの混合物を30分間〜60分間攪拌した。次いで、トリエチルアミン(「TEA」;1.5モル当量)を添加し、そしてこの混合物を2時間〜3時間攪拌した。さらなるEDC(1.5モル当量)およびTEA(1.5モル当量)を添加し、そしてこの混合物を12時間〜16時間攪拌し、次いで、酢酸エチルで希釈し、そして重炭酸ナトリウム飽和水溶液で2回洗浄し、続いて塩化ナトリウム飽和水溶液で洗浄した。その有機相を無水硫酸ナトリウムで乾燥させ、次いで、減圧下で濃縮した。次いで、この濃縮物を分取C18HPLCにより精製して、所望の化合物(すなわち、それぞれ化合物18、19、20または21)を得た。
1H NMR(CD3OD):δ8.99(s,1H),7.90(d,1H),7.23(m,10H),5.38(s,2H),4.52(m,2H),4.42(m,2H),4.18(bs,1H),4.05(bs,1H),3.58(s,4H),3.22(m,2H),2.97(s,3H),2.76(m,2H),2.32(m,6H),1.73(m,4H),1.38(d,J=6.9Hz,6H);質量分析(m/e):(M+H)+762.3、(M−H)−760.3。
1H NMR(CD3OD):δ8.99(s,1H),7.91(d,1H),7.20(m,6H),5.33(bs,2H),4.58(m,2H),4.21(m,1H),4.08(m,1H),4.05(bs,1H),3.61(s,4H),3.31(m,4H),2.99(s,3H),2.80(m,2H),2.40(m,6H),1.80(m,5H),1.38(d,J=6.9Hz,6H),0.79(m,6H);質量分析(m/e):(M+H)+ 728.3、(M−H)− 726.3。
1H NMR(CD3OD):δ8.99(s,1H),7.89(d,1H),7.19(m,10H),5.37(s,2H),4.51(m,4H),4.18(bs,1H),4.03(bs,1H),3.63(m,4H),3.32(m,4H),2.97(m,3H),2.76(m,2H),2.42(m,6H),1.78(m,4H),1.37(m,6H);質量分析(m/e):(M+H)+ 796.2、(M−H)− 794.2。
1H NMR(CD3OD):δ8.96(s,1H),7.89(d,1H),7.19(m,9H),5.37(s,2H),4.52(m,4H),4.17(m,2H),3.57(m,4H),3.31(m,4H),2.96(s,3H),2.77(m,2H),2.31(m,6H),1.82(m,4H),1.36(m,6H)
質量分析(m/e):(M+H)+ 796.2、(M−H)− 794.2。
化合物6(593mg,1.85mmol)のジクロロメタン(12.0mL)中の溶液に、周囲温度で、トリエチルアミン(280μL,2.04mmol)および4−ニトロベンゼンスルホニルクロリド(430mg,1.94mmol,Aldrichから入手)を順番に添加した。3時間攪拌した後に、この反応混合物を水に注ぎ、そしてジクロロメタンで抽出した。その有機層をブラインで洗浄し、Na2SO4で乾燥させ、そして濃縮して、淡橙色固体を得た。この固体を、ヘキサンを用いて酢酸エチルから沈殿させて、化合物23(694mg,74%)を白色固体として得た。
化合物23(350mg,0.70mmol)のメタノール(15.0mL)および酢酸エチル(1.0mL)中の溶液に、炭素担持Pd(10重量%,300mg)を添加した。この反応混合物を周囲温度で水素雰囲気下(バルーンによる)で2時間攪拌した。次いで、この反応混合物をセライトのパッドで濾過し、そして濃縮して、オフホワイトの泡状物(化合物24)を得、これをさらに精製せずに次の工程において使用した。
上記反応工程からの固体の化合物24を、0℃で、1,4−ジオキサン中のHCl(12.0mLの4.0M溶液)で処理した。この反応物を周囲温度まで温め、そして2時間攪拌し、その後、沈殿が形成した。この反応混合物を減圧下で濃縮して、化合物25(300mg,2工程について95%)を、自由に流動するオフホワイトの粉末として得た。
化合物25(80mg,0.18mmol)および1−(4−ニトロ−フェニル)−3−ヘキサヒドロ−フロ[2,3−b]フラン−3−イルカーボネート(化合物26,63mg,0.21mmol)(Bioorg.Med.Chem.Lett.,(2005),3496に記載される手順に従って調製した)の乾燥アセトニトリル(3.0mL)中のスラリーに、N,N−ジイソプロピルエチルアミン(95.0μL,0.53mmol)を周囲温度で滴下した。この反応混合物を一晩攪拌し、ブラインに注ぎ、そして酢酸エチルで抽出した。その有機層をブラインで洗浄し、Na2SO4で乾燥させ、濃縮し、そしてジクロロメタン中5%のメタノールを使用するフラッシュカラムクロマトグラフィーにより精製して、固体を得た。1H NMR分析は、所望の生成物と一緒に、4−ニトロフェノールの存在を示した。単離した固体を酢酸エチルに溶解し、そして1.0N水性NaOHで3回、水、ブラインで洗浄し、Na2SO4で乾燥させ、そして濃縮して、化合物27(53mg,56%)をオフホワイトの泡状物として得た。
1H NMR(300MHz,CDCl3):δ0.86(d,J=6.3Hz,3H),0.87(d,J=6.3Hz,3H),1.65-1.98(m,4H),2.74-2.90(m,4H),2.94-3.16(m,6H),3.70-4.18(m,5H),4.80(br d,J=9.0Hz,1H),5.04-5.15(m,1H),5.71(d,J=5.4Hz,1H),6.67(d,J=8.4Hz,2H),7.10-7.35(m,5H),7.53(d,J=8.7Hz,2H)。LC/MS:532(M+1)。
化合物25(90mg,0.20mmol)および炭酸2,5−ジオキソ−ピロリジン−1−イルエステルテトラヒドロ−フラン−3−イルエステル(46mg,0.20mmol)(US 5585397、WO 94/05639、およびWO96/33184に記載される手順に従って調製した)の乾燥アセトニトリル(3.0mL)中の懸濁物に、トリエチルアミン(90.0μL,0.64mmol)を周囲温度で滴下した。この反応物を1時間攪拌し、次いで、酢酸エチルで希釈した。次いで、この反応混合物を水、ブラインで洗浄し、Na2SO4で乾燥させ、そして濃縮して、固体を得た。ジクロロメタン中5%のメタノールを使用するフラッシュカラムクロマトグラフィーによる精製により、化合物28(41mg,42%)を無色泡状物として得た。
1H NMR(300MHz,CDCl3):δ0.85(d,J=6.3Hz,6H),1.54-2.20(m,5H),2.70-2.86(m,4H),2.96-3.18(m,2H),3.62-3.96(m,5H),4.14(br s,2H),4.72(br d,J=8.1Hz,1H),5.18(br s,1H),6.64(d,J=8.4Hz,2H),7.10-7.35(m,5H),7.52(d,J=8.4Hz,2H)。LC/MS:490(M+1)。
アミン6a(1mmol)を1−ヒドロキシベンゾトリアゾール水和物(1.2モル当量)と混合し、そして無水DMF(5mL)中の化合物12(1モル当量)、およびN−(3−ジメチルアミノプロピル)−N’−エチルカルボジイミド(1.2モル当量)を添加した。得られた混合物を12時間〜16時間攪拌した。
化合物29(0.68mmol)をジオキサン中4NのHCl(5mL〜10mL)に溶解し、そして45分間攪拌した。次いで、この混合物を減圧下で濃縮して、油状物を得た。得られた油状物をDCMに再溶解し、そして減圧下で濃縮した。得られた物質を無水DMF(5mL)に溶解し、化合物8(1.1モル当量)およびTEA(3モル当量)を添加し、そしてこの混合物を室温で16時間攪拌した。
1H NMR(CD3OD):δ8.98(s,1H),7.84(s,1H),7.20(m,6H),5.24(m,2H),4.70(m,1H),4.52(m,2H),3.63(m,6H),3.31(m,4H),2.98(s,3H),2.76(m,3H),2.43(m,5H),1.76(m,5H),1.39(m,6H),0.84(m,6H)
質量分析(m/e):(M+H)+ 728.2、(M−H+HOAc)− 785.8。
化合物(101)をジオキサン中4NのHCl(10ml)に溶解し、そして60分間攪拌した。この反応溶液を減圧下で濃縮した。その残渣をTHFで希釈し、そして減圧下で濃縮した。化合物102(1モル当量)の無水DMF中の溶液をこの濃縮した反応混合物に添加した。順番に、1−ヒドロキシベンゾトリアゾール水和物(1.5モル当量)およびN−(3−ジメチルアミノプロピル)−N’−エチルカルボジイミド塩酸塩(1.2モル当量)を、この反応混合物に添加した。30分後、ジイソプロピルエチルアミン(2モル当量)を添加し、そしてこの反応物を16時間攪拌した。この反応混合物を酢酸エチルで希釈し、そして重炭酸ナトリウム飽和水溶液で2回洗浄し、続いて塩化ナトリウム飽和水溶液で洗浄した。その有機相を無水硫酸ナトリウムで乾燥させ、次いで、減圧下で濃縮した。その残渣を分取C18HPLCで精製して、所望の化合物103を得た。
1H NMR(CD3OD):δ9.01(s,1H),7.89(s,1H),7.20(m,11H),6.17(d,J=8.4Hz,1H),5.38(s,2H),4.47(m,4H),3.98(m,2H),3.26(m,4H),2.96(s,3H),2.74(m,2H),1.90−1.60(m,3H),1.36(d,J=6.9Hz,6H),0.83(bs,6H)。
質量分析(m/e):(M+H)+ 691.2、(M−H)− 689.2。
化合物(101)(133mg,0.337mmol)をジオキサン中4NのHCl(5mL)に溶解し、そして60分間攪拌した。この反応溶液を減圧下で濃縮した。その残渣をEtOAcに溶解し、そして重炭酸ナトリウム飽和水溶液で2回洗浄し、続いて塩化ナトリウム飽和水溶液で洗浄した。その有機相を無水硫酸ナトリウムで乾燥させ、次いで、減圧下で濃縮した。その残渣を無水DMF(5mL)に溶解した。順番に、化合物104(116mg,0.404mol)、1−ヒドロキシベンゾトリアゾール水和物(62mg,0.404mol)およびN−(3−ジメチルアミノプロピル)−N’−エチルカルボジイミド(60μL,0.404mol)を添加し、そしてこの混合物を15分間攪拌した。トリエチルアミン(94μL,0.674mol)を添加し、そしてこの反応物を16時間攪拌した。
1H NMR(CD3OD):δ8.98(m,1H),8.90(s,1H),7.86(m,1H),7.81(s,1H),7.21(m,10H),5.37(s,2H),4.71(m,2H),4.46(m,2H),4.21(bs,1H),4.04(bs,1H),3.62(m,4H),3.22(m,2H),2.93(s,3H),2.76(m,2H),2.32(m,6H),1.78(m,4H)
質量分析(m/e):(M+H)+ 720.3、(M−H)− 718.2。
(材料および一般方法)
プールされた(n≧15のドナーの)ヒト肝臓ミクロソーム画分をBD−Gentest(Woburn,MA)から得、ここは、ヒドロキシ−テルフェナジン、4’−ヒドロキシジクロフェナクおよびNADPH再生系もまた供給した。リトナビルを、市販のNorvir(登録商標)経口溶液(Abbott Laboratories,Abbott Park,IL)から調製した。他の試薬は、Sigma−Aldrich(St.Louis,MO)製であり、テルフェナジン、フェキソフェナジン、BRL 15572、ジクロフェナクおよびメフェナム酸を含んだ。
CYP3Aサブファミリー(特に、CYP3A4)のヒト肝臓シトクロムP450のインヒビターとしてンこの化合物の力価を、テルフェナジンオキシダーゼ(Ling,K.−H.J.ら,Drug Metab.Dispos.23,631−636,(1995)およびJurima−Rometら,Drug Metab.Dispos.22,849−857,(1994)に記載される、充分に特徴付けられたCYP3A選択的活性)を使用して評価した。ミクロソームタンパク質およびテルフェナジン基質の最終濃度は、それぞれ0.25mg/mLおよび3μMであった。代謝反応を、0.1μM BRL 15572を内部標準として含有する7倍体積のクエンチ溶液での処理により終結させた。さらに8倍体積の水を添加し、その後、遠心分離し、そしてその上清のアリコートを分析のために取り出した。
ヒト肝臓CYP2C9のインヒビターとしてンこの化合物の力価を、ジクロフェナク4’−ヒドロキシラーゼ(Leeman,T.ら,Life Sci.52,29−34,(1992)に記載されるように、この酵素に対して特異的な活性)を使用して評価した。ミクロソームタンパク質およびジクロフェナク基質の最終濃度は、それぞれ0.08mg/mLおよび4μMであった。代謝反応を、1μMのメフェナム酸を内部標準として含有する3倍体積のクエンチ溶液での処理により終結させた。遠心分離後、さらに4倍体積の水を添加した。次いで、その上清のアリコートをLC−MS分析に供した。
(HIV−1プロテアーゼ酵素アッセイ(Ki))
このアッセイは、最初にM.V.TothおよびG.R.Marshall,Int.J.Peptide Protein Res.36,544(1990)(全ての目的でその全体が本明細書中に参考として援用される)に記載されたように、規定された反応緩衝液中での、HIV−1プロテアーゼによる合成ヘキサペプチド基質の切断の蛍光測定検出に基づく。
上記Kiアッセイについてと同様に、IC50アッセイは、最初にM.V.TothおよびG.R.Marshall,Int.J.Peptide Protein Res.36,544(1990)に記載されたように、規定された反応緩衝液中での、HIV−1プロテアーゼによる合成ヘキサペプチド基質の切断の蛍光測定検出に基づく。
このアッセイは、試験されるインヒビターの存在下または非存在下での、ウイルス感染した細胞の生存能力の比色定量検出による、HIV−1関連細胞変性効果の定量に基づく。HIV−1で誘導された細胞死を、代謝物質である2,3−ビス(2−メトキシ−4−ニトロ−5−スルホフェニル)−2H−テトラゾリウム−5−カルボキサニリド(XTT)(これは、Weislow OS,Kiser R,Fine DL,Bader J,Shoemaker RHおよびBoyd MR,J.Natl.Cancer Inst.81,577(1989)(全ての目的でその全体が本明細書中に参考として援用される)により記載されるように、インタクトな細胞によってのみ、固有の吸収特性を有する生成物に変換される)を使用して決定した。
このアッセイは、感染を生理学的濃度の40%ヒト血清(AB型男性、Cambrex 14−498E)またはヒト血清タンパク質(ヒトα−酸糖タンパク質,Sigma G−9885;ヒト血清アルブミン,Sigma A1653,96%〜99%)の存在下または非存在下で行ったこと以外は、上記抗HIV−1細胞培養アッセイとほとんど同一である。HIV−1により誘導された細胞死を、96ウェルプレートに分配する感染細胞を、培養培地中ではなく、80%ヒト血清中(2倍濃度)または2mg/mLのヒトα−酸糖タンパク質+70mg/mLのHSA中(2倍濃度)でインキュベートしたことを除いては上記のように決定した。
このアッセイは、Weislow OS,Kiser R,Fine DL,Bader J,Shoemaker RHおよびBoyd MR,J. Natl.Cancer Inst.81,577(1989)により記載されるような、代謝基質である2,3−ビス(2−メトキシ−4−ニトロ−5−スルホフェニル)−2H−テトラゾリウム−5−カルボキサニリド(XTT)を使用する、試験される化合物の細胞傷害性効果の評価に基づく。このアッセイは、細胞を感染「させなかった」こと以外は、先に記載したアッセイ(抗HIV−1細胞培養アッセイ)とほとんど同じである。化合物により誘導された細胞死(または増殖の低下)を、先に記載したように決定した。
Claims (27)
- 式I
X1は、-C(O)−O−、−S(O)−、および−S(O2)−、−C(O)NR6−からなる群より選択され;
X2は、-O−、-NR6−C(O)−NR6−、−OC(O)NR6−、−NR6−、および−NR6C(O)O−からなる群より選択され;
Lは、共有結合、アルキレン、および-CHR7−からなる群より選択され;
R1は、アリール、ヘテロアリール、アリールアルキル、およびヘテロアリールアルキルからなる群より選択され;
各R2は独立して、H、アルキル、アリールアルキル、ヘテロシクリルアルキル、およびシクロアルキルアルキルからなる群より選択され、ここで少なくとも1つのR2は、アルキル、アリールアルキル、ヘテロシクリルアルキルまたはシクロアルキルアルキルであり;
R3は、ヘテロシクリル、アリール、ヘテロアリール、アリールアルキル、およびヘテロアリールアルキルからなる群より選択され;
R4およびR5は各々独立して、H、アルキル、シクロアルキル、ヘテロシクリル、シクロアルキルアルキル、アリールアルキル、およびヘテロシクリルアルキルからなる群より選択され;
各R6は独立して、H、アルキル、およびシクロアルキルからなる群より選択され;そして
R7は、H、アルキル、置換アルキル、およびヘテロシクリルアルキルからなる群より選択され;
ここでR1、R2、R3、R4、R5、R6およびR7の各アリール、ヘテロアリール、シクロアルキル、ヘテロシクリル、シクロアルキルアルキル、ヘテロシクリルアルキル、アリールアルキル、およびヘテロアリールアルキルは、置換されていないかまたは置換されている、
化合物。 - 少なくとも1つのR2が置換アリールアルキルまたは非置換アリールアルキルである、請求項1に記載の化合物。
- X1が-C(O)−O−または-S(O2)−である、請求項1または2に記載の化合物。
- -L−X2−が-CHR7−NR6−C(O)−NR6−または-O−である、請求項1〜3のいずれか1項に記載の化合物。
- 式IIのR1が、非置換チアゾリルメチルまたは置換チアゾリルメチルである、請求項5に記載の化合物。
- R3が、置換ヘテロシクリルまたは非置換ヘテロシクリル、あるいは置換ヘテロアリールアルキルまたは非置換ヘテロアリールアルキルである、請求項5に記載の化合物。
- R7が非置換ヘテロシクリルアルキルまたは置換ヘテロシクリルアルキルである、請求項5に記載の化合物。
- 式IIIのR1が置換アリールまたは非置換アリールである、請求項5に記載の化合物。
- 請求項1〜10のいずれか1項に記載の化合物、あるいはその薬学的に受容可能な塩、溶媒和物、および/またはエステル、ならびに薬学的に受容可能なキャリアまたは賦形剤を含有する、薬学的組成物。
- 少なくとも1種のさらなる治療剤をさらに含有する、請求項11に記載の薬学的組成物。
- 前記少なくとも1種のさらなる治療剤が、HIVプロテアーゼ阻害化合物、HIVの逆トランスクリプターゼの非ヌクレオシドインヒビター、HIVの逆トランスクリプターゼのヌクレオシドインヒビター、HIVの逆トランスクリプターゼのヌクレオチドインヒビター、HIVインテグラーゼインヒビター、gp41インヒビター、CXCR4インヒビター、gp120インヒビター、CCR5インヒビター、カプシド重合インヒビター、インターフェロン、リバビリンアナログ、NS3プロテアーゼインヒビター、α−グルコシダーゼ1インヒビター、肝臓保護物質、HCVの非ヌクレオシドインヒビター、HCVを処置するための他の薬物、ならびにこれらの組み合わせからなる群より選択される、請求項12に記載の薬学的組成物。
- (1)前記HIVプロテアーゼインヒビターが、アンプレナビル、アタザナビル、ホスアンプレナビル、インジナビル、ロピナビル、リトナビル、ネルフィナビル、サキナビル、チプラナビル、ブレカナビル、ダルナビル、TMC−126、TMC−114、モゼナビル(DMP−450)、JE−2147(AG1776)、L−756423、RO0334649、KNI−272、DPC−681、DPC−684、GW640385X、DG17、PPL−100、DG35、およびAG 1859からなる群より選択され;
(2)前記HIVの逆トランスクリプターゼの非ヌクレオシドインヒビターが、カプラビリン、エミビリン、デラビルジン、エファビレンツ、ネビラピン、(+)カラノリドA、エトラビリン、GW5634、DPC−083、DPC−961、DPC−963、MIV−150、およびTMC−120、TMC−278(リルピビリン)、エファビレンツ、BILR 355 BS、VRX 840773、UK−453061、およびRDEA806からなる群より選択され;
(3)前記HIVの逆トランスクリプターゼのヌクレオシドインヒビターが、ジドブジン、エムトリシタビン、ジダノシン、スタブジン、ザルシタビン、ラミブジン、アバカビル、アムドキソビル、エルブシタビン、アロブジン、MIV−210、ラシビル(±−FTC)、D−d4FC、エムトリシタビン、ホスファジド、ホジブジンチドキシル、アプリシチビン(AVX754)、アムドキソビル、KP−1461、およびフォサルブジンチドキシル(旧名称HDP 99.0003)からなる群より選択され;
(4)前記HIVの逆トランスクリプターゼのヌクレオチドインヒビターが、テノホビルおよびアデホビルからなる群より選択され;
(5)前記HIVインテグラーゼインヒビターが、クルクミン、クルクミンの誘導体、チコリ酸、チコリ酸の誘導体、3,5−ジカフェオイルキナ酸、3,5−ジカフェオイルキナ酸の誘導体、オーリントリカルボン酸、オーリントリカルボン酸の誘導体、コーヒー酸フェネチルエステル、コーヒー酸フェネチルエステルの誘導体、チロホスチン、チロホスチンの誘導体、ケルセチン、ケルセチンの誘導体、S−1360、ジンテビル(AR−177)、L−870812、およびL−870810、エルビテグラビル、MK−0518(ラルテグラビル)、BMS−538158、GSK364735C、BMS−707035、MK−2048、およびBA 011からなる群より選択され;
(6)前記gp41インヒビターが、エンフュービルタイド、シフビルチド、FB006M、およびTRI−1144からなる群より選択され;
(7)前記CXCR4インヒビターがAMD−070であり;
(8)前記侵入阻害剤がSP01Aであり;
(9)前記gp120インヒビターがBMS−488043またはBlockAide/CRであり;
(10)前記G6PDおよびNADHオキシダーゼインヒビターがイムニチンであり;
(11)前記CCR5インヒビターが、アプラビロック、ビクリビロック、マラビロック、PRO−140、INCB15050、PF−232798(Pfizer)、およびCCR5mAb004からなる群より選択され;
(12)前記HIVを処置するための他の薬物が、BAS−100、SPI−452、REP 9、SP−01A、TNX−355、DES6、ODN−93、ODN−112、VGV−1、PA−457(ベビリマト)、アンプリゲン、HRG214、サイトリン、VGX−410、KD−247、AMZ 0026、CYT 99007A−221 HIV、DEBIO−025、BAY 50−4798、MDX010(イピリムマブ)、PBS 119、ALG 889、およびPA−1050040(PA−040)からなる群より選択され;
(13)前記インターフェロンが、PEG化rIFN−α2b、PEG化rIFN−α2a、rIFN−α2b、rIFN−α2a、コンセンサスIFNα(インフェルゲン)、フエロン、レアフェロン、インターマックスα、r−IFN−β、インフェルゲン+アクティミューン、IFN−ωとDUROS、アルブフェロン、ロクテロン、アルブフェロン、レビフ、経口インターフェロンα、IFNα−2b XL、AVI−005、PEG−インフェルゲン、およびPEG化IFN−βからなる群より選択され;
(14)前記リバビリンアナログが、レベトール、コペガス、およびビラミジン(タリバビリン)からなる群より選択され;
(15)前記NS5bポリメラーゼインヒビターが、NM−283、バロピシタビン、R1626、PSI−6130(R1656)、HCV−796、BILB 1941、XTL−2125、MK−0608、NM−107、R7128(R4048)、VCH−759、PF−868554、およびGSK625433からなる群より選択され;
(16)前記NS3プロテアーゼインヒビターが、SCH−503034(SCH−7)、VX−950(テラプレビル)、BILN−2065、BMS−605339、およびITMN−191からなる群より選択され;
(17)前記α−グルコシダーゼ1インヒビターが、MX−3253(セルゴシビル)およびUT−231Bからなる群より選択され;
(18)前記肝臓保護物質が、IDN−6556、ME 3738、LB−84451、およびMitoQからなる群より選択され;
(19)前記HCVの非ヌクレオシドインヒビターが、ベンゾイミダゾール誘導体、ベンゾ−1,2,4−チアジアジン誘導体、フェニルアラニン誘導体、A−831、およびA−689からなる群より選択され;そして
(20)前記HCVを処置するための他の薬物が、ザダキシン、ニタゾキサニド(アリネア)、BIVN−401(ビロスタット)、PYN−17(アルチレックス)、KPE02003002、アクチロン(CPG−10101)、KRN−7000、シバシル、GI−5005、ANA−975、XTL−6865、ANA 971、NOV−205、タルバシン、EHC−18、NIM811、DEBIO−025、VGX−410C、EMZ−702、AVI 4065、バビツキシマブ、オグルファニド、およびVX−497(メリメポジブ)からなる群より選択される、
請求項13に記載の薬学的組成物。 - シトクロムP450モノオキシゲナーゼにより代謝される薬物の薬物速度論を改善するか、または血漿中レベルを上昇させる方法であって、該薬物で処置されている患者に、薬物速度論を改善するかまたは血漿中レベルを上昇させる有効量の、請求項1〜10のいずれか1項に記載の化合物、あるいはその薬学的に受容可能な塩、溶媒和物、および/またはエステルを投与する工程を包含する、方法。
- 前記投与する工程が、前記薬物と、請求項1〜10のいずれか1項に記載の化合物、あるいは請求項1〜10のいずれか1項に記載の化合物の薬学的に受容可能な塩、溶媒和物、および/またはエステルとを含有する治療有効量の組み合わせを投与する工程を包含する、請求項15に記載の方法。
- 前記シトクロムP450により代謝される薬物が、HIVプロテアーゼ阻害化合物、HIVの逆トランスクリプターゼの非ヌクレオシドインヒビター、HIVの逆トランスクリプターゼのヌクレオシドインヒビター、HIVの逆トランスクリプターゼのヌクレオチドインヒビター、HIVインテグラーゼインヒビター、gp41インヒビター、CXCR4インヒビター、gp120インヒビター、CCR5インヒビター、カプシド重合インヒビター、HIVを処置するための他の薬物、インターフェロン、リバビリンアナログ、NS3プロテアーゼインヒビター、α−グルコシダーゼ1インヒビター、肝臓保護物質、HCVの非ヌクレオシドインヒビター、NS5aインヒビター、NS5bポリメラーゼインヒビター、HCVを処置するための他の薬物、またはこれらの混合物である、請求項16に記載の方法。
- 前記薬物が、6−(3−クロロ−2−フルオロベンジル)−1−((2S)−1−ヒドロキシ−3−メチルブタン−2−イル)−7−メトキシ−4−オキソ−1,4−ジヒドロキノリン−3−カルボン酸またはアタザナビルである、請求項17に記載の方法。
- 前記薬物と、請求項1〜10のいずれか1項に記載の化合物または塩とが、単一の組成物として前記患者に投与される、請求項15に記載の方法。
- 投与される請求項1〜10のいずれか1項に記載の化合物の量が、シトクロムP450モノオキシゲナーゼを阻害するために有効である、請求項15に記載の方法。
- HIV感染を処置する方法であって、該方法は、その必要がある患者に、治療有効量の請求項1〜10のいずれか1項に記載の化合物、あるいはその薬学的に受容可能な塩、溶媒和物、および/またはエステルを、治療有効量の1種以上のさらなる治療剤と組み合わせて投与する工程を包含し、該さらなる治療剤は、HIVプロテアーゼ阻害化合物、HIVの逆トランスクリプターゼの非ヌクレオシドインヒビター、HIVの逆トランスクリプターゼのヌクレオシドインヒビター、HIVの逆トランスクリプターゼのヌクレオチドインヒビター、HIVインテグラーゼインヒビター、gp41インヒビター、CXCR4インヒビター、gp120インヒビター、G6PDおよびNADHオキシダーゼインヒビター、CCR5インヒビター、HIVを処置するための他の薬物、およびこれらの混合物からなる群より選択される、方法。
- (1)前記HIVプロテアーゼインヒビターが、アンプレナビル、アタザナビル、ホスアンプレナビル、インジナビル、ロピナビル、リトナビル、ネルフィナビル、サキナビル、チプラナビル、ブレカナビル、ダルナビル、TMC−126、TMC−114、モゼナビル(DMP−450)、JE−2147(AG1776)、L−756423、RO0334649、KNI−272、DPC−681、DPC−684、GW640385X、DG17、PPL−100、DG35、およびAG 1859からなる群より選択され;
(2)前記HIVの逆トランスクリプターゼの非ヌクレオシドインヒビターが、カプラビリン、エミビリン、デラビルジン、エファビレンツ、ネビラピン、(+)カラノリドA、エトラビリン、GW5634、DPC−083、DPC−961、DPC−963、MIV−150、およびTMC−120、TMC−278(リルピビリン)、エファビレンツ、BILR 355 BS、VRX 840773、UK−453061、およびRDEA806からなる群より選択され;
(3)前記HIVの逆トランスクリプターゼのヌクレオシドインヒビターが、ジドブジン、エムトリシタビン、ジダノシン、スタブジン、ザルシタビン、ラミブジン、アバカビル、アムドキソビル、エルブシタビン、アロブジン、MIV−210、ラシビル(±−FTC)、D−d4FC、エムトリシタビン、ホスファジド、ホジブジンチドキシル、アプリシチビン(AVX754)、アムドキソビル、KP−1461、およびフォサルブジンチドキシル(旧名称HDP 99.0003)からなる群より選択され;
(4)前記HIVの逆トランスクリプターゼのヌクレオチドインヒビターが、テノホビル、およびアデホビルからなる群より選択され;
(5)前記HIVインテグラーゼインヒビターが、クルクミン、クルクミンの誘導体、チコリ酸、チコリ酸の誘導体、3,5−ジカフェオイルキナ酸、3,5−ジカフェオイルキナ酸の誘導体、オーリントリカルボン酸、オーリントリカルボン酸の誘導体、コーヒー酸フェネチルエステル、コーヒー酸フェネチルエステルの誘導体、チロホスチン、チロホスチンの誘導体、ケルセチン、ケルセチンの誘導体、S−1360、ジンテビル(AR−177)、L−870812、およびL−870810、エルビテグラビル、MK−0518(ラルテグラビル)、BMS−538158、GSK364735C、BMS−707035、MK−2048、およびBA 011からなる群より選択され;
(6)前記gp41インヒビターが、エンフュービルタイド、シフビルチド、FB006M、およびTRI−1144からなる群より選択され;
(7)前記CXCR4インヒビターがAMD−070であり;
(8)前記侵入阻害剤がSP01Aであり;
(9)前記gp120インヒビターが、BMS−488043またはBlockAide/CRであり;
(10)前記G6PDおよびNADHオキシダーゼインヒビターがイムニチンであり;
(11)前記CCR5インヒビターが、アプラビロック、ビクリビロック、マラビロック、PRO−140、INCB15050、PF−232798(Pfizer)、およびCCR5mAb004からなる群より選択され;
(12)前記HIVを処置するための他の薬物が、BAS−100、SPI−452、REP 9、SP−01A、TNX−355、DES6、ODN−93、ODN−112、VGV−1、PA−457(ベビリマト)、アンプリゲン、HRG214、サイトリン、VGX−410、KD−247、AMZ 0026、CYT 99007A−221 HIV、DEBIO−025、BAY 50−4798、MDX010(イピリムマブ)、PBS 119、ALG 889、およびPA−1050040(PA−040)からなる群より選択される、
請求項21に記載の方法。 - HCV感染を処置する方法であって、該方法は、その必要がある患者に、治療有効量の請求項1〜10のいずれか1項に記載の化合物、あるいはその薬学的に受容可能な塩、溶媒和物、および/またはエステルを、治療有効量の1種以上のさらなる治療剤と組み合わせて投与する工程を包含し、該さらなる治療剤は、インターフェロン、リバビリンアナログ、NS3プロテアーゼインヒビター、α−グルコシダーゼ1インヒビター、肝臓保護物質、HCVの非ヌクレオシドインヒビター、およびHCVを処置するための他の薬物、またはこれらの混合物からなる群より選択される、方法。
- (1)前記インターフェロンが、PEG化rIFN−α2b、PEG化rIFN−α2a、rIFN−α2b、rIFN−α2a、コンセンサスIFNα(インフェルゲン)、フエロン、レアフェロン、インターマックスα、r−IFN−β、インフェルゲン+アクティミューン、IFN−ωとDUROS、アルブフェロン、ロクテロン、アルブフェロン、レビフ、経口インターフェロンα、IFNα−2b XL、AVI−005、PEG−インフェルゲン、およびPEG化IFN−βからなる群より選択され;
(2)前記リバビリンアナログが、レベトール、コペガス、およびビラミジン(タリバビリン)からなる群より選択され;
(3)前記NS5bポリメラーゼインヒビターが、NM−283、バロピシタビン、R1626、PSI−6130(R1656)、HCV−796、BILB 1941、XTL−2125、MK−0608、NM−107、R7128(R4048)、VCH−759、PF−868554、およびGSK625433からなる群より選択され;
(4)前記NS3プロテアーゼインヒビターが、SCH−503034(SCH−7)、VX−950(テラプレビル)、BILN−2065、BMS−605339、およびITMN−191からなる群より選択され;
(5)前記α−グルコシダーゼ1インヒビターが、MX−3253(セルゴシビル)およびUT−231Bからなる群より選択され;
(6)前記肝臓保護物質が、IDN−6556、ME 3738、LB−84451、およびMitoQからなる群より選択され;
(7)前記HCVの非ヌクレオシドインヒビターが、ベンゾイミダゾール誘導体、ベンゾ−1,2,4−チアジアジン誘導体、フェニルアラニン誘導体、A−831、およびA−689からなる群より選択され;そして
(8)前記HCVを処置するための他の薬物が、ザダキシン、ニタゾキサニド(アリネア)、BIVN−401(ビロスタット)、PYN−17(アルチレックス)、KPE02003002、アクチロン(CPG−10101)、KRN−7000、シバシル、GI−5005、ANA−975、XTL−6865、ANA 971、NOV−205、タルバシン、EHC−18、NIM811、DEBIO−025、VGX−410C、EMZ−702、AVI 4065、バビツキシマブ、オグルファニド、およびVX−497(メリメポジブ)からなる群より選択される、
請求項23に記載の方法。 - 患者において、シトクロムP450モノオキシゲナーゼにより代謝される薬物の薬物速度論を改善するため、シトクロムP450モノオキシゲナーゼにより代謝される薬物の血漿中レベルを増加させるため、シトクロムP450モノオキシゲナーゼを阻害するため、HIV感染を処置するため、またはHCV感染を処置するための医薬の製造のための、請求項1〜10のいずれか1項に記載の化合物の使用。
- 前記医薬が、請求項1〜10のいずれか1項に記載の化合物と1種以上のさらなる治療剤との組み合わせであり、該さらなる治療剤が、HIVプロテアーゼ阻害化合物、HIVの逆トランスクリプターゼの非ヌクレオシドインヒビター、HIVの逆トランスクリプターゼのヌクレオシドインヒビター、HIVの逆トランスクリプターゼのヌクレオチドインヒビター、HIVインテグラーゼインヒビター、gp41インヒビター、CXCR4インヒビター、gp120インヒビター、G6PDおよびNADHオキシダーゼインヒビター、CCR5インヒビター、HIVを処置するための他の薬物、インターフェロン、リバビリンアナログ、NS5bポリメラーゼインヒビター、NS3プロテアーゼインヒビター、α−グルコシダーゼ1インヒビター、肝臓保護物質、HCVの非ヌクレオシドインヒビター、およびHCVを処置するための他の薬物、ならびにこれらの混合物からなる群より選択される、請求項25に記載の使用。
- (1)前記HIVプロテアーゼインヒビターが、アンプレナビル、アタザナビル、ホスアンプレナビル、インジナビル、ロピナビル、リトナビル、ネルフィナビル、サキナビル、チプラナビル、ブレカナビル、ダルナビル、TMC−126、TMC−114、モゼナビル(DMP−450)、JE−2147(AG1776)、L−756423、RO0334649、KNI−272、DPC−681、DPC−684、GW640385X、DG17、PPL−100、DG35、およびAG 1859からなる群より選択され;
(2)前記HIVの逆トランスクリプターゼの非ヌクレオシドインヒビターが、カプラビリン、エミビリン、デラビルジン、エファビレンツ、ネビラピン、(+)カラノリドA、エトラビリン、GW5634、DPC−083、DPC−961、DPC−963、MIV−150、およびTMC−120、TMC−278(リルピビリン)、エファビレンツ、BILR 355 BS、VRX 840773、UK−453061、およびRDEA806からなる群より選択され;
(3)前記HIVの逆トランスクリプターゼのヌクレオシドインヒビターが、ジドブジン、エムトリシタビン、ジダノシン、スタブジン、ザルシタビン、ラミブジン、アバカビル、アムドキソビル、エルブシタビン、アロブジン、MIV−210、ラシビル(±−FTC)、D−d4FC、エムトリシタビン、ホスファジド、ホジブジンチドキシル、アプリシチビン(AVX754)、アムドキソビル、KP−1461、およびフォサルブジンチドキシル(旧名称HDP 99.0003)からなる群より選択され;
(4)前記HIVの逆トランスクリプターゼのヌクレオチドインヒビターが、テノホビル、およびアデホビルからなる群より選択され;
(5)前記HIVインテグラーゼインヒビターが、クルクミン、クルクミンの誘導体、チコリ酸、チコリ酸の誘導体、3,5−ジカフェオイルキナ酸、3,5−ジカフェオイルキナ酸の誘導体、オーリントリカルボン酸、オーリントリカルボン酸の誘導体、コーヒー酸フェネチルエステル、コーヒー酸フェネチルエステルの誘導体、チロホスチン、チロホスチンの誘導体、ケルセチン、ケルセチンの誘導体、S−1360、ジンテビル(AR−177)、L−870812、およびL−870810、エルビテグラバー(elvitegravor)、MK−0518(ラルテグラビル)、BMS−538158、GSK364735C、BMS−707035、MK−2048、およびBA 011からなる群より選択され;
(6)前記gp41インヒビターが、エンフュービルタイド、シフビルチド、FB006M、およびTRI−1144からなる群より選択され;
(7)前記CXCR4インヒビターがAMD−070であり;
(8)前記侵入阻害剤がSP01Aであり;
(9)前記gp120インヒビターが、BMS−488043またはBlockAide/CRであり;
(10)前記G6PDおよびNADHオキシダーゼインヒビターがイムニチンであり;
(11)前記CCR5インヒビターが、アプラビロック、ビクリビロック、マラビロック、PRO−140、INCB15050、PF−232798(Pfizer)、およびCCR5mAb004からなる群より選択され;
(12)前記HIVを処置するための他の薬物が、BAS−100、SPI−452、REP 9、SP−01A、TNX−355、DES6、ODN−93、ODN−112、VGV−1、PA−457(ベビリマト)、アンプリゲン、HRG214、サイトリン、VGX−410、KD−247、AMZ 0026、CYT 99007A−221 HIV、DEBIO−025、BAY 50−4798、MDX010(イピリムマブ)、PBS 119、ALG 889、およびPA−1050040(PA−040)からなる群より選択され;
(13)前記インターフェロンが、PEG化rIFN−α2b、PEG化rIFN−α2a、rIFN−α2b、rIFN−α2a、コンセンサスIFNα(インフェルゲン)、フエロン、レアフェロン、インターマックスα、r−IFN−β、インフェルゲン+アクティミューン、IFN−ωとDUROS、アルブフェロン、ロクテロン、アルブフェロン、レビフ、経口インターフェロンα、IFNα−2b XL、AVI−005、PEG−インフェルゲン、およびPEG化IFN−βからなる群より選択され;
(14)前記リバビリンアナログが、レベトール、コペガス、およびビラミジン(タリバビリン)からなる群より選択され;
(15)前記NS5bポリメラーゼインヒビターが、NM−283、バロピシタビン、R1626、PSI−6130(R1656)、HCV−796、BILB 1941、XTL−2125、MK−0608、NM−107、R7128(R4048)、VCH−759、PF−868554、およびGSK625433からなる群より選択され;
(16)前記NS3プロテアーゼインヒビターが、SCH−503034(SCH−7)、VX−950(テラプレビル)、BILN−2065、BMS−605339、およびITMN−191からなる群より選択され;
(17)前記α−グルコシダーゼ1インヒビターが、MX−3253(セルゴシビル)およびUT−231Bからなる群より選択され;
(18)前記肝臓保護物質が、IDN−6556、ME 3738、LB−84451、およびMitoQからなる群より選択され;
(19)前記HCVの非ヌクレオシドインヒビターが、ベンゾイミダゾール誘導体、ベンゾ−1,2,4−チアジアジン誘導体、フェニルアラニン誘導体、A−831、およびA−689からなる群より選択され;そして
(20)前記HCVを処置するための他の薬物が、ザダキシン、ニタゾキサニド(アリネア)、BIVN−401(ビロスタット)、PYN−17(アルチレックス)、KPE02003002、アクチロン(CPG−10101)、KRN−7000、シバシル、GI−5005、ANA−975、XTL−6865、ANA 971、NOV−205、タルバシン、EHC−18、NIM811、DEBIO−025、VGX−410C、EMZ−702、AVI 4065、バビツキシマブ、オグルファニド、およびVX−497(メリメポジブ)からなる群より選択される、
請求項26に記載の使用。
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US20090175820A1 (en) | 2009-07-09 |
AU2008346823A1 (en) | 2009-07-16 |
CA2710679A1 (en) | 2009-07-16 |
PT2231628E (pt) | 2015-12-29 |
HK1148520A1 (zh) | 2011-09-09 |
AU2008346823B2 (en) | 2015-03-12 |
WO2009088719A1 (en) | 2009-07-16 |
JP5629585B2 (ja) | 2014-11-19 |
US8759379B2 (en) | 2014-06-24 |
EP2231628B1 (en) | 2015-10-28 |
ES2555209T3 (es) | 2015-12-29 |
EP2231628A1 (en) | 2010-09-29 |
JP2014169338A (ja) | 2014-09-18 |
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