JP5401502B2 - 細胞壊死インヒビター - Google Patents
細胞壊死インヒビター Download PDFInfo
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- JP5401502B2 JP5401502B2 JP2011116383A JP2011116383A JP5401502B2 JP 5401502 B2 JP5401502 B2 JP 5401502B2 JP 2011116383 A JP2011116383 A JP 2011116383A JP 2011116383 A JP2011116383 A JP 2011116383A JP 5401502 B2 JP5401502 B2 JP 5401502B2
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- lower alkyl
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- 208000007089 vaccinia Diseases 0.000 description 1
- 229940093257 valacyclovir Drugs 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
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- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
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- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 231100000889 vertigo Toxicity 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000033041 viral attachment to host cell Effects 0.000 description 1
- 230000007486 viral budding Effects 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 229960005080 warfarin Drugs 0.000 description 1
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
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- 238000001086 yeast two-hybrid system Methods 0.000 description 1
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- 239000011787 zinc oxide Substances 0.000 description 1
- 229960002769 zofenopril Drugs 0.000 description 1
- IAIDUHCBNLFXEF-MNEFBYGVSA-N zofenopril Chemical compound C([C@@H](C)C(=O)N1[C@@H](C[C@@H](C1)SC=1C=CC=CC=1)C(O)=O)SC(=O)C1=CC=CC=C1 IAIDUHCBNLFXEF-MNEFBYGVSA-N 0.000 description 1
- 229960003516 zomepirac sodium Drugs 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 description 1
- 108091058550 ω-conotoxin Proteins 0.000 description 1
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Description
本発明は、国立衛生研究所助成金番号GM−64703の基で政府の支援によりなされた。政府は、本発明に関し特定の権利を有し得る。
本出願は、2003年8月29日に出願された米国仮出願番号第60/498,882号の出願日の優先権を米国特許法第119条(e)のもとで主張し、これは、本明細書で参考として援用される。
本発明は、細胞死に関連する疾患を予防および処置するための組成物ならびに方法に関する。特に、本発明は、細胞死と関連する神経系疾患を処置するための治療化合物および方法に関する。
急性および慢性の神経系疾患は、多くの異なる要因に起因し得る。しかしながら、これらの疾患の多くは中枢神経系の特定の領域における細胞死に特徴づけられる。
本発明は、細胞壊死と関連する障害を処置するのに有用な化合物および薬学的調製物を提供する。
例えば、本発明は以下の項目を提供する。
(項目1)
下式の化合物:
その立体異性体形態、その薬学的に受容可能な酸付加塩、または塩基付加塩であって;ここで
Xは、Oを表し;
Yは、Sを表し;
Gは、OまたはNR 7 を表し;
R 1 、R 2 、およびR 3 は、独立してH、OH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、COOH、CO 2 R 8 、NO 2 、NHC(O)R 8 、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリールを表し;
R 4 は、独立してH、OH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、COOH、CO 2 R 8 、NO 2 、NHC(O)R 8 、メチル、メトキシ、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリール、アミン、ピペラジンを表し;
R 5 、R 6 、およびR 7 は、独立してHまたは低級アルキルを表し;R 8 は、低級アルキル、置換低級アルキル、アリール、置換アリール、アリールアルキル、アルケニル、アルキニル、ヘテロアリール、または置換ヘテロアリールを表し;
R 9 、R 10 、R 9 ’、R 10 ’は独立して、H、F、Cl、Br、I、低級アルキル、置換低級アルキル、あるいはC n および/あるいはC n ’を含む3〜6員シクロアルキルまたは置換シクロアルキルを表し;
nおよびn’は、0〜5の整数である、化合物。
(項目2)
項目1に記載の化合物と薬学的に受容可能なキャリアとを含む薬学的調製物。
(項目3)
前記薬学的に受容可能なキャリアが、希釈剤、固体賦形剤および溶媒をカプセル化する物質から選択される、項目2に記載の薬学的調製物。
(項目4)
項目2に記載の薬学的調製物であって、前記薬学的に受容可能なキャリアが、糖、デンプン、セルロース、粉末化トラガカント、麦芽、ゼラチン、タルク、賦形剤、オイル、グリコール、ポリオール、エステル、寒天、緩衝剤、アルギン酸、発熱物質を含まない水、等張生理食塩水、リンゲル溶液、エチルアルコール、pH緩衝溶液、ポリエステル、ポリアンヒドリドおよびポリカーボネートから選択される、調製物。
(項目5)
壊死細胞疾患を有する被験体に下式の化合物:
その立体異性体形態、その薬学的に受容可能な酸付加塩、または塩基付加塩であって;ここで
Xは、Oを表し;
Yは、Sを表し;
Gは、OまたはNR 7 を表し;
R 1 、R 2 、およびR 3 は、独立してH、OH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、COOH、CO 2 R 8 、NO 2 、NHC(O)R 8 、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリールを表し;
R 4 は、独立してH、OH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、COOH、CO 2 R 8 、NO 2 、NHC(O)R 8 、メチル、メトキシ、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリール、アミン、ピペラジンを表し;
R 5 、R 6 、およびR 7 は、独立してHまたは低級アルキルを表し;R 8 は、低級アルキル置換低級アルキル、アリール、置換アリール、アリールアルキル、アルケニル、アルキニル、ヘテロアリール、または置換ヘテロアリールを表し;
R 9 、R 10 、R 9 ’、R 10 ’は独立して、H、F、Cl、Br、I、低級アルキル、置換低級アルキル、あるいはC n および/あるいはC n ’を含む3〜6員シクロアルキルまたは置換シクロアルキルを表し;
nおよびn’は、0〜5の整数である、化合物
を投与する工程を包含する、壊死細胞疾患を処置する方法であって、ここで該化合物を、壊死細胞疾患を処置するために有効な量投与する、方法。
(項目6)
前記壊死細胞疾患が外傷、虚血、発作、心筋梗塞、感染、および敗血症からなる群より選択される、項目5に記載の方法。
(項目7)
前記壊死細胞疾患が、パーキンソン病、アルツハイマー病、筋萎縮性側索硬化症、ハンチントン病、およびHIV関連痴呆から選択される神経変性疾患である、項目5に記載の方法。
(項目8)
前記化合物が経口経路、非経口経路、局所経路、眼経路、経皮経路および鼻経路から選択される経路で投与される、項目5に記載の方法。
(項目9)
前記化合物が、皮下注射、筋肉内注射、静脈内注射または硬膜外注射により投与される、項目5に記載の方法。
(項目10)
前記化合物が、薬学的に受容可能なキャリアとの組合わせで投与される、項目5に記載の方法。
(項目11)
前記化合物が、別の化合物との組合わせで投与される、項目5に記載の方法。
(項目12)
前記化合物が、アポトーシスインヒビター、PARPインヒビター、Srcインヒビター、発作を処置する物質、心臓血管系障害を処置する物質および抗菌剤からなる一覧より選択される、項目11に記載の方法。
(項目13)
下式の化合物:
その立体異性体形態、その薬学的に受容可能な酸付加塩、または塩基付加塩であって;ここで
Xは、Oを表し;
Yは、NR 8 を表し;
Gは、OまたはNR 7 を表し;
R 1 、R 2 、およびR 3 は、独立してH、OH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、COOH、CO 2 R 8 、NO 2 、NHC(O)R 8 、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリールを表し;
R 4 は、独立してH、OH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、COOH、CO 2 R 8 、NO 2 、NHC(O)R 8 、メチル、メトキシ、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリール、アミン、ピペラジンを表し;
R 5 、R 6 、およびR 7 は、独立してHまたは低級アルキルを表し;
R 8 は、低級アルキル、置換低級アルキル、アリール、置換アリール、アリールアルキル、アルケニル、アルキニル、ヘテロアリール、または置換ヘテロアリールを表し;
R 9 、R 10 、R 9 ’、R 10 ’は独立して、H、F、Cl、Br、I、低級アルキル、置換低級アルキル、あるいはC n および/あるいはC n ’を含む3〜6員シクロアルキルまたは置換シクロアルキルを表し;ならびに
nおよびn’は、0〜5の整数である、化合物。
(項目14)
項目13に記載の化合物と薬学的に受容可能なキャリアとを含む薬学的調製物。
(項目15)
前記薬学的に受容可能なキャリアが、希釈剤、固体賦形剤および溶媒をカプセル化する物質から選択される、項目14に記載の薬学的調製物。
(項目16)
項目14に記載の薬学的調製物であって、前記薬学的に受容可能なキャリアが、糖、デンプン、セルロース、粉末化トラガカント、麦芽、ゼラチン、タルク、賦形剤、オイル、グリコール、ポリオール、エステル、寒天、緩衝剤、アルギン酸、発熱物質を含まない水、等張食塩水、リンゲル溶液、エチルアルコール、pH緩衝溶液、ポリエステル、ポリアンヒドリドおよびポリカーボネートから選択される、調製物。
(項目17)
壊死細胞疾患を有する被験体に下式の化合物:
その立体異性体形態、その薬学的に受容可能な酸付加塩、または塩基付加塩であって;ここで
Xは、Oを表し;
Yは、NR 8 を表し;
Gは、OまたはNR 7 を表し;
R 1 、R 2 、およびR 3 は、独立してH、OH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、COOH、CO 2 R 8 、NO 2 、NHC(O)R 8 、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリールを表し;
R 4 は、独立してH、OH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、COOH、CO 2 R 8 、NO 2 、NHC(O)R 8 、メチル、メトキシ、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリール、アミン、ピペラジンを表し;
R 5 、R 6 、およびR 7 は、独立してHまたは低級アルキルを表し;
R 8 は、低級アルキル、置換低級アルキル、アリール、置換アリール、アリールアルキル、アルケニル、アルキニル、ヘテロアリール、または置換ヘテロアリールを表し;
R 9 、R 10 、R 9 ’、R 10 ’は独立して、H、F、Cl、Br、I、低級アルキル、置換低級アルキル、あるいはC n および/あるいはC n ’を含む3〜6員シクロアルキルまたは置換シクロアルキルを表し;ならびに
nおよびn’は、0〜5の整数である、化合物
を投与する工程を包含する、壊死細胞疾患を処置する方法であって、ここで該化合物を、壊死細胞疾患を処置するために有効な量投与する、方法。
(項目18)
前記壊死細胞疾患が外傷、虚血、発作、心筋梗塞、感染、および敗血症からなる群より選択される、項目17に記載の方法。
(項目19)
前記壊死細胞疾患が、パーキンソン病、アルツハイマー病、筋萎縮性側索硬化症、ハンチントン病、およびHIV関連痴呆から選択される神経変性疾患である、項目17に記載の方法。
(項目20)
前記化合物が経口、非経口、局所、眼、経皮および鼻から選択される経路で投与される、項目17に記載の方法。
(項目21)
前記化合物が、皮下、筋肉内、静脈内または硬膜外注射により投与される、項目17に記載の方法。
(項目22)
前記化合物が、薬学的に受容可能なキャリアとの組合わせで投与される、項目17に記載の方法。
(項目23)
前記化合物が、別の化合物との組合わせで投与される、項目17に記載の方法。
(項目24)
前記化合物が、アポトーシスインヒビター、PARPインヒビター、Srcインヒビター、発作を処置する物質、心臓血管系障害を処置する物質および抗菌剤からなる一覧より選択される、項目23に記載の方法。
(項目25)
下式の化合物:
その立体異性体形態、その薬学的に受容可能な酸付加塩、または塩基付加塩であって;ここで
Xは、Oを表し;
Yは、NHを表し;
R 1 、R 2 、およびR 3 は、独立してH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、CO 2 R 8 、NO 2 、NHC(O)R 8 、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリールを表し;
R 4 は、独立してH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、CO 2 R 8 、NO 2 、NHC(O)R 8 、メチル、メトキシ、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリール、アミン、ピペラジンを表し;
R 5 、R 6 、およびR 7 は、独立してHまたは低級アルキルを表すが、R 1 、R 2 、R 3 、R 4 、R 5 、およびR 7 がHの場合、R 6 は、メチル、エチル、プロピル、イソプロピルおよびt−ブチルではあり得ないことを除き;
R 8 は、H、低級アルキル、置換低級アルキル、アリール、置換アリール、アリールアルキル、アルケニル、アルキニル、ヘテロアリール、または置換ヘテロアリールを表し;
R 9 、R 10 、R 9 ’、R 10 ’は独立して、H、F、Cl、Br、I、低級アルキル、置換低級アルキル、あるいはC n および/あるいはC n ’を含む3〜6員シクロアルキルまたは置換シクロアルキルを表し;ならびに
nおよびn’は、0〜5の整数である、化合物。
(項目26)
R 4 が、ハロゲン、好ましくはClまたはFを表す、項目25に記載の化合物。
(項目27)
R 4 が、メチルまたはメトキシを表す、項目25に記載の化合物。
(項目28)
R 6 が、メチル基を表す、項目25に記載の化合物。
(項目29)
R 4 が、Clを表す、項目25に記載の化合物。
(項目30)
R 4 が、メチルを表す、項目25に記載の化合物。
(項目31)
R 4 が、メトキシを表す、項目25に記載の化合物。
(項目32)
項目25〜31のいずれか1項に記載の化合物と薬学的に受容可能なキャリアとを含む薬学的調製物。
(項目33)
前記薬学的に受容可能なキャリアが、希釈剤、固体賦形剤および溶媒をカプセル化する物質から選択される、項目32に記載の薬学的調製物。
(項目34)
項目32に記載の薬学的調製物であって、前記薬学的に受容可能なキャリアが、糖、デンプン、セルロース、粉末化トラガカント、麦芽、ゼラチン、タルク、賦形剤、オイル、グリコール、ポリオール、エステル、寒天、緩衝剤、アルギン酸、発熱物質を含まない水、等張食塩水、リンゲル溶液、エチルアルコール、pH緩衝溶液、ポリエステル、ポリアンヒドリドおよびポリカーボネートから選択される、調製物。
(項目35)
壊死細胞疾患を有する被験体に下式の化合物:
その立体異性体形態、その薬学的に受容可能な酸付加塩、または塩基付加塩であって;ここで
Xは、Oを表し;
Yは、NHを表し;
R 1 、R 2 、およびR 3 は、独立してH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、CO 2 R 8 、NO 2 、NHC(O)R 8 、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリールを表し;
R 4 は、独立してH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、CO 2 R 8 、NO 2 、NHC(O)R 8 、メチル、メトキシ、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリール、アミン、ピペラジンを表し;
R 5 、R 6 、およびR 7 は、独立してHまたは低級アルキルを表すが、R 1 、R 2 、R 3 、R 4 、R 5 、およびR 7 がHの場合、R 6 は、メチル、エチル、プロピル、イソプロピルおよびt−ブチルではあり得ないことを除き;
R 8 は、H、低級アルキル、置換低級アルキル、アリール、置換アリール、アリールアルキル、アルケニル、アルキニル、ヘテロアリール、または置換ヘテロアリールを表し;
R 9 、R 10 、R 9 ’、R 10 ’は独立して、H、F、Cl、Br、I、低級アルキル、置換低級アルキル、あるいはC n および/あるいはC n ’を含む3〜6員シクロアルキルまたは置換シクロアルキルを表し;
nおよびn’は、0〜5の整数である、化合物
を投与する工程を包含する、壊死細胞疾患を処置する方法であって、ここで該化合物を、壊死細胞疾患を処置するために有効な量投与する、方法。
(項目36)
R 4 が、ハロゲン、好ましくはClまたはFを表す、項目35に記載の化合物。
(項目37)
R 4 が、メチルまたはメトキシを表す、項目35に記載の化合物。
(項目38)
R 6 が、メチル基を表す、項目35に記載の化合物。
(項目39)
R 4 が、Clを表す、項目38に記載の化合物。
(項目40)
R 4 が、メチルを表す、項目39に記載の化合物。
(項目41)
R 4 が、メトキシを表す、項目39に記載の化合物。
(項目42)
前記壊死細胞疾患が外傷、虚血、発作、心筋梗塞、感染、および敗血症からなる群より選択される、項目35〜41のいずれか1項に記載の方法。
(項目43)
前記壊死細胞疾患が、パーキンソン病、アルツハイマー病、筋萎縮性側索硬化症、ハンチントン病、およびHIV関連痴呆から選択される神経変性疾患である、項目35〜41のいずれか1項に記載の方法。
(項目44)
前記化合物が経口、非経口、局所、眼、経皮および鼻から選択される経路で投与される、項目35〜41のいずれか1項に記載の方法。
(項目45)
前記化合物が、皮下、筋肉内、静脈内または硬膜外注射により投与される、項目35〜41のいずれか1項に記載の方法。
(項目46)
前記化合物が、薬学的に受容可能なキャリアとの組合わせで投与される、項目35〜41のいずれか1項に記載の方法。
(項目47)
前記化合物が、別の化合物との組合わせで投与される、項目35〜41のいずれか1項に記載の方法。
(項目48)
前記化合物が、アポトーシスインヒビター、PARPインヒビター、Srcインヒビター、発作を処置する物質、心臓血管系障害を処置する物質および抗菌剤からなる一覧より選択される、項目47に記載の方法。
(項目49)
下式の化合物:
その立体異性体形態、その薬学的に受容可能な酸付加塩、または塩基付加塩であって;ここで
Xは、Sを表し;
Yは、Sを表し;
Gは、OまたはNR 7 を表し;
R 1 、R 2 、およびR 3 は、独立してH、OH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、COOH、CO 2 R 8 、NO 2 、NHC(O)R 8 、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリールを表し;
R 4 は、独立してH、OH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、COOH、CO 2 R 8 、NO 2 、NHC(O)R 8 、メチル、メトキシ、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリール、アミン、ピペラジンを表し;
R 5 、R 6 、およびR 7 は、独立してHまたは低級アルキルを表し;
R 8 は、低級アルキル、置換低級アルキル、アリール、置換アリール、アリールアルキル、アルケニル、アルキニル、ヘテロアリール、または置換ヘテロアリールを表し;
R 9 、R 10 、R 9 ’、R 10 ’は独立して、H、F、Cl、Br、I、低級アルキル、置換低級アルキル、あるいはC n および/あるいはC n ’を含む3〜6員シクロアルキルまたは置換シクロアルキルを表し;
nおよびn’は、0〜5の整数である、化合物。
(項目50)
項目49に記載の化合物と薬学的に受容可能なキャリアとを含む薬学的調製物。
(項目51)
前記薬学的に受容可能なキャリアが、希釈剤、固体賦形剤および溶媒をカプセル化する物質から選択される、項目50に記載の薬学的調製物。
(項目52)
項目50に記載の薬学的調製物であって、前記薬学的に受容可能なキャリアが、糖、デンプン、セルロース、粉末化トラガカント、麦芽、ゼラチン、タルク、賦形剤、オイル、グリコール、ポリオール、エステル、寒天、緩衝剤、アルギン酸、発熱物質を含まない水、等張食塩水、リンゲル溶液、エチルアルコール、pH緩衝溶液、ポリエステル、ポリアンヒドリドおよびポリカーボネートから選択される、調製物。
(項目53)
壊死細胞疾患を有する被験体に下式の化合物:
その立体異性体形態、その薬学的に受容可能な酸付加塩、または塩基付加塩であって;ここで
Xは、Sを表し;
Yは、Sを表し;
Gは、OまたはNR 7 を表し;
R 1 、R 2 、およびR 3 は、独立してH、OH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、COOH、CO 2 R 8 、NO 2 、NHC(O)R 8 、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリールを表し;
R 4 は、独立してH、OH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、COOH、CO 2 R 8 、NO 2 、NHC(O)R 8 、メチル、メトキシ、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリール、アミン、ピペラジンを表し;
R 5 、R 6 、およびR 7 は、独立してHまたは低級アルキルを表し;
R 8 は、低級アルキル、置換低級アルキル、アリール、置換アリール、アリールアルキル、アルケニル、アルキニル、ヘテロアリール、または置換ヘテロアリールを表し;
R 9 、R 10 、R 9 ’、R 10 ’は独立して、H、F、Cl、Br、I、低級アルキル、置換低級アルキル、あるいはC n および/あるいはC n ’を含む3〜6員シクロアルキルまたは置換シクロアルキルを表し;
nおよびn’は、0〜5の整数である、化合物
を投与する工程を包含する、壊死細胞疾患を処置する方法であって、ここで該化合物を、壊死細胞疾患を処置するために有効な量投与する、方法。
(項目54)
前記壊死細胞疾患が外傷、虚血、発作、心筋梗塞、感染、および敗血症からなる群より選択される、項目57に記載の方法。
(項目55)
前記壊死細胞疾患が、パーキンソン病、アルツハイマー病、筋萎縮性側索硬化症、ハンチントン病、およびHIV関連痴呆から選択される神経変性疾患である、項目57に記載の方法。
(項目56)
前記化合物が経口、非経口、局所、眼、経皮および鼻から選択される経路で投与される、項目57に記載の方法。
(項目57)
前記化合物が、皮下、筋肉内、静脈内または硬膜外注射により投与される、項目57に記載の方法。
(項目58)
前記化合物が、薬学的に受容可能なキャリアとの組合わせで投与される、項目57に記載の方法。
(項目59)
前記化合物が、別の化合物との組合わせで投与される、項目57に記載の方法。
(項目60)
前記化合物が、アポトーシスインヒビター、PARPインヒビター、Srcインヒビター、発作を処置する物質、心臓血管系障害を処置する物質および抗菌剤からなる一覧より選択される、項目57に記載の方法。
(項目61)
下式の化合物:
その立体異性体形態、その薬学的に受容可能な酸付加塩、または塩基付加塩であって;ここで
Xは、Sを表し;
Yは、NR 8 を表し;
Gは、OまたはNR 7 を表し;
R 1 、R 2 、およびR 3 は、独立してH、OH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、COOH、CO 2 R 8 、NO 2 、NHC(O)R 8 、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリールを表し;
R 4 は、独立してH、OH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、COOH、CO 2 R 8 、NO 2 、NHC(O)R 8 、メチル、メトキシ、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリール、アミン、ピペラジンを表し;
R 5 、R 6 、およびR 7 は、独立してHまたは低級アルキルを表し;R 8 は、低級アルキル、置換低級アルキル、アリール、置換アリール、アリールアルキル、アルケニル、アルキニル、ヘテロアリール、または置換ヘテロアリールを表し;
R 9 、R 10 、R 9 ’、R 10 ’は独立して、H、F、Cl、Br、I、低級アルキル、置換低級アルキル、あるいはC n および/あるいはC n ’を含む3〜6員シクロアルキルまたは置換シクロアルキルを表し;ならびに
nおよびn’は、0〜5の整数である、化合物。
(項目62)
項目61に記載の化合物と薬学的に受容可能なキャリアを含む薬学的調製物。
(項目63)
前記薬学的に受容可能なキャリアが、希釈剤、固体賦形剤および溶媒をカプセル化する物質から選択される、項目62に記載の薬学的調製物。
(項目64)
項目62に記載の薬学的調製物であって、前記薬学的に受容可能なキャリアが、糖、デンプン、セルロース、粉末化トラガカント、麦芽、ゼラチン、タルク、賦形剤、オイル、グリコール、ポリオール、エステル、寒天、緩衝剤、アルギン酸、発熱物質を含まない水、等張食塩水、リンゲル溶液、エチルアルコール、pH緩衝溶液、ポリエステル、ポリアンヒドリドおよびポリカーボネートから選択される、調製物。
(項目65)
壊死細胞疾患を有する被験体に下式の化合物:
その立体異性体形態、その薬学的に受容可能な酸付加塩、または塩基付加塩であって;ここで
Xは、Sを表し;
Yは、NR 8 を表し;
Gは、OまたはNR 7 を表し;
R 1 、R 2 、およびR 3 は、独立してH、OH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、COOH、CO 2 R 8 、NO 2 、NHC(O)R 8 、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリールを表し;
R 4 は、独立してH、OH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、COOH、CO 2 R 8 、NO 2 、NHC(O)R 8 、メチル、メトキシ、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリール、アミン、ピペラジンを表し;
R 5 、R 6 、およびR 7 は、独立してHまたは低級アルキルを表し;R 8 は、低級アルキル、置換低級アルキル、アリール、置換アリール、アリールアルキル、アルケニル、アルキニル、ヘテロアリール、または置換ヘテロアリールを表し;
R 9 、R 10 、R 9 ’、R 10 ’は独立して、H、F、Cl、Br、I、低級アルキル、置換低級アルキル、あるいはC n および/あるいはC n ’を含む3〜6員シクロアルキルまたは置換シクロアルキルを表し、
nおよびn’は、0〜5の整数である、化合物
を投与する工程を包含する、壊死細胞疾患を処置する方法であって、ここで該化合物を、壊死細胞疾患を処置するために有効な量投与する、方法。
(項目66)
前記壊死細胞疾患が外傷、虚血、発作、心筋梗塞、感染、および敗血症からなる群より選択される、項目65に記載の方法。
(項目67)
前記壊死細胞疾患が、パーキンソン病、アルツハイマー病、筋萎縮性側索硬化症、ハンチントン病、およびHIV関連痴呆から選択される神経変性疾患である、項目65に記載の方法。
(項目68)
前記化合物が経口、非経口、局所、眼、経皮および鼻から選択される経路で投与される、項目65に記載の方法。
(項目69)
前記化合物が、皮下、筋肉内、静脈内または硬膜外注射により投与される、項目65に記載の方法。
(項目70)
前記化合物が、薬学的に受容可能なキャリアとの組合わせで投与される、項目65に記載の方法。
(項目71)
前記化合物が、別の化合物との組合わせで投与される、項目65に記載の方法。
(項目72)
前記化合物が、アポトーシスインヒビター、PARPインヒビター、Srcインヒビター、発作を処置する物質、心臓血管系障害を処置する物質および抗菌剤からなる一覧より選択される、項目65に記載の方法。
(項目73)
下式の化合物:
その立体異性体形態、その薬学的に受容可能な酸付加塩、または塩基付加塩であって;ここで
Xは、Sを表し;
Yは、NHを表し;
Gは、OまたはNR 7 を表し;
R 1 、R 2 、およびR 3 は、独立してH、OH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、COOH、CO 2 R 8 、NO 2 、NHC(O)R 8 、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリールを表し;
R 4 は、独立してH、OH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、CO 2 R 8 、NO 2 、NHC(O)R 8 、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリール、アミン、ピペラジン、メチルとメトキシとを除く低級アルキルならびに置換低級アルキルを表し;
R 5 、R 6 、およびR 7 は、独立してHまたは低級アルキルを表すが、R 1 、R 2 、R 3 、R 4 、R 5 、およびR 7 がHの場合、R 6 は、メチルではあり得ないことを除き;R 8 は、H、低級アルキル、置換低級アルキル、アリール、置換アリール、アリールアルキル、アルケニル、アルキニル、ヘテロアリール、または置換ヘテロアリールを表し;
R 9 、R 10 、R 9 ’、R 10 ’は独立して、H、F、Cl、Br、I、低級アルキル、置換低級アルキル、あるいはC n および/あるいはC n ’を含む3〜6員シクロアルキルまたは置換シクロアルキルを表し;ならびに
nおよびn’は、0〜5の整数である、化合物。
(項目74)
R 4 が、ハロゲン、好ましくはClまたはFを表す、項目73に記載の化合物。
(項目75)
R 4 が、Clを表し、そしてR 6 がメチルを表す、項目74に記載の化合物。
(項目76)
項目73〜75のいずれか1項に記載の化合物と薬学的に受容可能なキャリアを含む薬学的調製物。
(項目77)
前記薬学的に受容可能なキャリアが、希釈剤、固体賦形剤および溶媒をカプセル化する物質から選択される、項目76に記載の薬学的調製物。
(項目78)
項目76に記載の薬学的調製物であって、前記薬学的に受容可能なキャリアが、糖、デンプン、セルロース、粉末化トラガカント、麦芽、ゼラチン、タルク、賦形剤、オイル、グリコール、ポリオール、エステル、寒天、緩衝剤、アルギン酸、発熱物質を含まない水、等張食塩水、リンゲル溶液、エチルアルコール、pH緩衝溶液、ポリエステル、ポリアンヒドリドおよびポリカーボネートから選択される、調製物。
(項目79)
壊死細胞疾患を有する被験体に下式の化合物:
その立体異性体形態、その薬学的に受容可能な酸付加塩、または塩基付加塩であって;ここで
Xは、Sを表し;
Yは、NHを表し;
Gは、OまたはNR 7 を表し;
R 1 、R 2 、およびR 3 は、独立してH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、CO 2 R 8 、NO 2 、NHC(O)R 8 、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリールを表し;
R 4 は、独立してH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、CO 2 R 8 、NO 2 、NHC(O)R 8 、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリール、アミン、ピペラジン、メチルおよびメトキシを除く低級アルキルならびに置換低級アルキルを表し;
R 5 、R 6 、およびR 7 は、独立してHまたは低級アルキルを表すが、GがNR 7 である場合であって、R 1 、R 2 、R 3 、R 4 、R 5 、およびR 7 がHの場合、R 6 は、メチルではあり得ないことを除き;
R 8 は、H、低級アルキル、置換低級アルキル、アリール、置換アリール、アリールアルキル、アルケニル、アルキニル、ヘテロアリール、または置換ヘテロアリールを表し;
R 9 、R 10 、R 9 ’、R 10 ’は独立して、H、F、Cl、Br、I、低級アルキル、置換低級アルキル、あるいはC n および/あるいはC n ’を含む3〜6員シクロアルキルまたは置換シクロアルキルを表し、
nおよびn’は、0〜5の整数である、化合物
を投与する工程を包含する、壊死細胞疾患を処置する方法であって、ここで該化合物を、壊死細胞疾患を処置するために有効な量投与する、方法。
(項目80)
R 4 が、ハロゲン、好ましくはClまたはFを表す、項目79に記載の方法。
(項目81)
R 4 が、ClそしてR 6 がメチルを表す、項目80に記載の方法。
(項目82)
前記壊死細胞疾患が外傷、虚血、発作、心筋梗塞、感染、および敗血症からなる群より選択される、項目79〜81のいずれか1項に記載の方法。
(項目83)
前記壊死細胞疾患が、パーキンソン病、アルツハイマー病、筋萎縮性側索硬化症、ハンチントン病、およびHIV関連痴呆から選択される神経変性疾患である、項目79〜81のいずれか1項に記載の方法。
(項目84)
前記化合物が経口、非経口、局所、眼、経皮および鼻から選択される経路で投与される、項目79〜81のいずれか1項に記載の方法。
(項目85)
前記化合物が、皮下、筋肉内、静脈内または硬膜外注射により投与される、項目79〜81のいずれか1項に記載の方法。
(項目86)
前記化合物が、薬学的に受容可能なキャリアとの組合わせで投与される、項目79〜81のいずれか1項に記載の方法。
(項目87)
前記化合物が、別の化合物との組合わせで投与される、項目79〜81のいずれか1項に記載の方法。
(項目88)
前記化合物が、アポトーシスインヒビター、PARPインヒビター、Srcインヒビター、発作を処置する物質、心臓血管系障害を処置する物質および抗菌剤からなる一覧より選択される、項目87に記載の方法。
(項目89)
下式の化合物:
その立体異性体形態、その薬学的に受容可能な酸付加塩、または塩基付加塩であって;ここで
Xは、SまたはOを表し;
Yは、NHまたはNR 8 を表し;
Gは、OまたはNR 7 を表し;
R 1 、R 2 、およびR 3 は、独立してH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、CO 2 R 8 、NO 2 、NHC(O)R 8 、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリールを表し;
R 4 は、独立してH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、CO 2 R 8 、NO 2 、NHC(O)R 8 、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリール、アミン、ピペラジン、メチルおよびメトキシを除く低級アルキルならびに置換低級アルキルを表し;
R 5 、R 6 、およびR 7 は、独立してHまたは低級アルキルを表し;R 8 は、H、低級アルキル、置換低級アルキル、アリール、置換アリール、アリールアルキル、アルケニル、アルキニル、ヘテロアリール、または置換ヘテロアリールを表し;
R 9 、R 10 、R 9 ’、R 10 ’は独立して、H、F、Cl、Br、I、低級アルキル、置換低級アルキル、あるいはC n および/あるいはC n ’を含む3〜6員シクロアルキルまたは置換シクロアルキルを表し、
nおよびn’は、0〜5の整数である、化合物。
(項目90)
R 4 が、ハロゲン、好ましくはClまたはFを表す、項目89に記載の化合物。
(項目91)
R 4 が、ClそしてR 6 がメチルを表す、項目89に記載の化合物。
(項目92)
項目89〜91のいずれか1項に記載の化合物と薬学的に受容可能なキャリアとを含む薬学的調製物。
(項目93)
前記薬学的に受容可能なキャリアが、希釈剤、固体賦形剤および溶媒をカプセル化する物質から選択される、項目92に記載の薬学的調製物。
(項目94)
項目92に記載の薬学的調製物であって、前記薬学的に受容可能なキャリアが、糖、デンプン、セルロース、粉末化トラガカント、麦芽、ゼラチン、タルク、賦形剤、オイル、グリコール、ポリオール、エステル、寒天、緩衝剤、アルギン酸、発熱物質を含まない水、等張食塩水、リンゲル溶液、エチルアルコール、pH緩衝溶液、ポリエステル、ポリアンヒドリドおよびポリカーボネートから選択される、調製物。
(項目95)
壊死細胞疾患を有する被験体に下式の化合物:
その立体異性体形態、その薬学的に受容可能な酸付加塩、または塩基付加塩であって;ここで
Xは、SまたはOを表し;
Yは、NHまたはNR 8 を表し;
Gは、OまたはNR 7 を表し;
R 1 、R 2 、およびR 3 は、独立してH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、CO 2 R 8 、NO 2 、NHC(O)R 8 、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリールを表し;
R 4 は、独立してH、OR 8 、F、Cl、Br、I、N(R 8 ) 2 、CO 2 R 8 、NO 2 、NHC(O)R 8 、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリール、アミン、ピペラジン、メチルおよびメトキシを除く低級アルキルならびに置換低級アルキルを表し;
R 5 、R 6 、およびR 7 は、独立してHまたは低級アルキルを表し;R 8 は、H、低級アルキル、置換低級アルキル、アリール、置換アリール、アリールアルキル、アルケニル、アルキニル、ヘテロアリール、または置換ヘテロアリールを表し;
R 9 、R 10 、R 9 ’、R 10 ’は独立して、H、F、Cl、Br、I、低級アルキル、置換低級アルキル、あるいはC n および/あるいはC n ’を含む3〜6員シクロアルキルまたは置換シクロアルキルを表し、
nおよびn’は、0〜5の整数である、化合物
を投与する工程を包含する、壊死細胞疾患を処置する方法であって、ここで該化合物を、壊死細胞疾患を処置するために有効な量投与する、方法。
(項目96)
R 4 が、ハロゲン、好ましくはClまたはFを表す、項目95に記載の方法。
(項目97)
R 4 が、ClそしてR 6 がメチルを表す、項目95に記載の方法。
(項目98)
前記壊死細胞疾患が外傷、虚血、発作、心筋梗塞、感染、および敗血症からなる群より選択される、項目95〜97のいずれか1項に記載の方法。
本発明は細胞死を防止し、そして細胞死疾患(例えば、外傷、虚血、神経系疾患および特に神経変性疾患)で悩まされる被験体を処置する治療物質として有用な化合物を提供する。本発明の化合物はまた、これらの疾患の病理−生理学を理解するために有用である。
Xは、OまたはSを表し;
Yは、S、NHまたはNR8を表し;
Gは、OまたはNR7を表し;
R1、R2、およびR3は、独立してH、OH、OR8、F、Cl、Br、I、N(R8)2、COOH、CO2R8、NO2、NHC(O)R8、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリールを表し;
R4は、独立してH、OH、OR8、F、Cl、Br、I、N(R8)2、COOH、CO2R8、NO2、NHC(O)R8、メチル、メトキシ、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリール、アミン、ピペラジンを表すが、好ましくはCl,Fまたはメトキシを表し;
R5、R6、およびR7は、独立してHまたは低級アルキルを表し;
R8は、低級アルキル、置換低級アルキル、アリール、置換アリール、アリールアルキル、アルケニル、アルキニル、ヘテロアリール、または置換ヘテロアリールを表し;
R9、R10、R9’、R10’は独立して、H、F、Cl、Br、I、低級アルキル、置換低級アルキル、あるいはCnおよび/あるいはCn’を含む3〜6員シクロアルキルまたは置換シクロアルキルを表し;
nおよびn’は、0〜5の整数であって;
以下の代替的実施形態上の制限:
i)Xは、Oを表し、Yは、NHを表し、そしてGはNR7を表す場合、R1、R2、R3、R4、R5、およびR7がHの場合、R6は、メチル、エチル、プロピル、イソプロピルおよびt−ブチルではあり得ない;
ii)Xは、Sを表し、Yは、NHを表し、そしてGはNR7を表す場合、R1、R2、R3、R4、R5、およびR7がHの場合、R6は、メチルではあり得ない;
iii)Xは、Sを表し、Yは、NHを表し、そしてGはNR7を表す場合、R4は、メチルまたはメトキシではあり得ない、制限を有する式の低分子量分子である。
Xは、OまたはSを表し;
Yは、S、NHまたはNR8を表し;
Gは、OまたはNR7を表し;
R1、R2、およびR3は、独立してH、OH、OR8、F、Cl、Br、I、N(R8)2、COOH、CO2R8、NO2、NHC(O)R8、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリールを表し;
R4は、独立してH、OH、OR8、F、Cl、Br、I、N(R8)2、COOH、CO2R8、NO2、NHC(O)R8、メチル、メトキシ、低級アルキル、置換低級アルキル、アリール、置換アリール、ヘテロアリール、または置換ヘテロアリール、アミン、ピペラジンを表すが、好ましくはCLまたはFを表し;
R5、R6、およびR7は、独立してHまたは低級アルキルを表し;
R8は、低級アルキル、置換低級アルキル、アリール、置換アリール、アリールアルキル、アルケニル、アルキニル、ヘテロアリール、または置換ヘテロアリールを表し;
R9、R10、R9’、R10’は独立して、H、F、Cl、Br、I、低級アルキル、置換低級アルキル、あるいはCnおよび/あるいはCn’を含む3〜6員シクロアルキルまたは置換シクロアルキルを表し;
nおよびn’は、0〜5の整数である、式の低分子量分子である。
本発明の化合物の薬学的に受容可能な塩としては、例えば非毒性の有機酸または無機酸由来の化合物の、従来の非毒性の塩または第四級アンモニウム塩が、挙げられる。例えば、そのような従来の非毒性の塩としては、塩酸、臭化水素酸、硫酸、スルファミン酸、リン酸、硝酸などのような無機酸から誘導される塩;酢酸、プロピオン酸、コハク酸、グリコール酸、ステアリン酸、乳酸、リンゴ酸、酒石酸、クエン酸、アスコルビン酸、パルミチン酸、マレイン酸、ヒドロキシマレイン酸、フェニル酢酸、グルタミン酸、安息香酸、サリチル酸、スルファニル酸、2−アセトキシ安息香酸、フマル酸、トルエンスルホン酸、メタンスルホン酸、エタンジスルフォン酸、シュウ酸、イセチオン酸(isothionic)などの有機酸から調製される塩が挙げられる。
そして/または本発明の薬学的組成物は、当業者に公知の従来の方法により薬学的に受容可能な投薬形態に処方される。
Modern Immunology、Wiley & Sons、Inc.,New
York;Roitt、I.(1991)Essential Immunology、7th Ed.、Blackwell Scientific Publications、Oxfordを参照のこと)。pFc’領域およびFc領域は、例えば補体カスケードのエフェクターであるが抗原結合とは関連しない。pFc’領域が酵素的に切断される、またはpFc’領域無しで産生される抗体(F(ab’)2フラグメントと指定される)は、インタクトの抗体の抗原結合部位の両方を維持する。同様にFc領域が酵素的に切断されるか、またはFc領域無しで産生される抗体(Fabフラグメントとして指定される)は、インタクトな抗体分子の1つの結合部位を保持する。さらに進んで、Fabフラグメントは、共有結合で結合した抗体L鎖とFdと示される抗体H鎖の一部分からなる。そのFdフラグメントは、抗体特異性(単一のFdフラグメントは抗体の特異性を変化させずに10までの異なるL鎖と関連し得る)の主要な決定基であり、Fdフラグメントはエピトープ結合能力を孤立して保持する。
ヒト被験体に感染してヒトの障害を引き起こすウイルスに加えて、本発明はまた、他の非ヒト脊椎動物を処置するのに有用である。非ヒト脊椎動物はまた、本明細書中に開示されるアジリジノ化合物と抗菌物質(anti−microbial)との組み合わせで予防または処置され得る感染を発達させ得る。例えば、ヒトの感染性疾患の処置に加えて、本発明の方法は、非ヒト動物の感染を処置または予防するのに有用である。
diarrhea virus)、マウスのロタウイルス、シミアンロタウイルス(simian rotavirus)、ウシまたはヒツジのロタウイルス、トリのロタウイルス)が挙げられる);Picornaviridae科(エンテロウイルス属(ポリオウイルス、コクサッキーウイルスAおよびB、エコー(ECHO)ウイルス、A型肝炎ウイルス、サルエンテロウイルス、マウス濃脊髄炎(ME)ウイルス、ポリオウイルスムリス(muris)、ウシエンテロウイルス、ブタエンテロウイルスが挙げられる)、カルジオウイルス属(脳心筋炎ウイルス(EMC)、メンゴウイルス)、ライノウイルス属(少なくとも113のサブタイプを包含するヒトのライノウイルス;他のライノウイルス)、アフトウイルス(Apthovirus)属(口蹄疫(FMDV));Calciviridae科(ブタ小水疱性発疹ウイルス、サンミグエルアザラシウイルス、ネコピコルナウイルスおよびノーウォークウイルスが挙げられる);Togaviridae科(アルファウイルス属(東部ウマ脳炎ウイルス、セムリキ森林ウイルス、シンドビスウイルス、チクングニヤウイルス、オニョンニョンウイルス(O’Nyong−Nyong virus)、ロス川ウイルス、ベネズエラウマ脳脊髄炎ウイルス、西部ウマ脳脊髄炎ウイルス)が挙げられる)、フラビウイルス属(蚊borne黄熱ウイルス、デング熱ウイルス、日本脳炎ウイルス、セントルイス脳炎ウイルス、マリーバレー脳炎ウイルス、西ナイルウイルス、クンジンウイルス、中央ヨーロッパダニウイルス(Central European tick borne virus)、極東ダニウイルス(Far Eastern tick borne virus)、キャサヌール森林ウイルス、跳躍病ウイルス(Louping III virus)、ポーワッサンウイルス、オムスク出血性熱ウイルスが挙げられる);ルビウイルス属(風疹ウイルス)、ペスチウイルス属(粘膜病ウイルス、豚コレラウイルス、ボーダー病ウイルス);Bunyaviridae科(ブンヤウイルス属(ブンヤムウェラウイルス(ブニヤンベラウイルス)およびその関連ウイルス、カリフォルニア脳炎群ウイルス)、フレボウイルス属(サシチョウバエ熱シシリー型ウイルス(Sandfly fever Sicilian virus)、リフトバレー熱ウイルス)、ナイロウイルス属(クリミア−コンゴ出血性熱ウイルス、ナイロビヒツジ病ウイルス)、ならびにウウクウイルス属(ウウクニエミーウイルスおよび関連ウイルス)が挙げられる);Orthomyxoviridae科(インフルエンザウイルス属(インフルエンザA型、ヒトの多くのサブタイプ);ブタインフルエンザウイルスおよびトリインフルエンザウイルスおよびウマインフルエンザウイルス;インフルエンザB型(ヒトの多くのサブタイプ)およびインフルエンザC型(恐らく別個の属);Paramyxoviridae科(パラミクソウイルス属(パラインフルエンザウイルス1型、センダイウイルス、血球吸着性ウイルス(Hemadsorption virus)、パラインフルエンザウイルス2型〜5型、ニューカッスル病ウイルス、流行性耳下腺炎ウイルスが挙げられる)、麻疹ウイルス属(麻疹ウイルス、亜急性硬化性汎脳ウイルス、ジステンパーウイルス、牛疫ウイルス)、肺炎ウイルス属(RSウイルス(RSV)、ウシRSウイルスおよびマウス肺炎ウイルス)が挙げられる);Rhabdoviridae科(ベシクロウイルス属(VSV)、チャンティプラウイルス、フランダースハートパークウイルス、リッサウイルス属(狂犬病ウイルス)、魚類ラブドウイルスおよびラブドウイルスとほぼ認められる2種のラブドウイルス(マルブルクウイルスおよびエボラウイルス)が挙げられる);Arenaviridae科(リンパ球性脈絡髄膜炎ウイルス(LCM)、タカリベウイルス群(Tacaribe virus complex)、およびラッサウイルスが挙げられる);Coronoaviridae科(感染性気管支炎ウイルス(IBV)、マウス肝炎ウイルス、ヒト腸内コロナウイルスおよびネコ感染性腹膜炎(ネココロナウイルス)が挙げられる)。
brunetti、Emeria adenoeides、Leucocytozoon、Plasmodium、Hemoproteus meleagridis、Toxoplasma gondiiおよびSarcocystisにより感染され得る。
berghei、Plasmodium yoelii、Giardia muris、Hexamita muris;Toxoplasma gondii;Trypanosoma duttoni(血漿);Klossiella muris;Sarcocystisが挙げられる。ラット中の代表的な寄生生物としては、Giardia muris、Hexamita muris;Toxoplasma gondii;Trypanosoma lewisi(血漿);Trichinella spiralis;およびSarcocystisが挙げられる。ウサギ中の代表的な寄生生物としては、Eimeria;Toxoplasma gondii;Nosema cuniculi;Eimeria stiedaeおよびSarcocystisが挙げられる。ハムスター中の代表的な寄生生物としては、Trichomonas;Toxoplasma gondii;Trichinella spiralis;およびSarcocystisが挙げられる。モルモット中の代表的な寄生生物としては、Balantidium caviae;Toxoplasma gondii;Klossiella caviae;およびSarcocystisが挙げられる。
真菌は、真核生物体であり、そのうちの僅かのものが脊椎哺乳動物において感染の原因になる。真菌は真核生物体であるので、それらは原核細菌とはサイズ、構造組織、ライフサイクルおよび増殖機構において著しく異なる。真菌は、一般的に形態学的特徴、生殖の様式および培養特性を基礎にして分類されている。真菌は、被験体において異なるタイプの疾患、例えば真菌抗原の吸入後の呼吸器系アレルギー、例えば毒性きのこが産生するアマトキシン(amatatoxin)およびファロトキシンならびにアスペルギルス種が産生するアフラトキシン(aflotoxin)などの毒性物質の摂取による真菌中毒の原因になるが、全ての真菌が感染性疾患の原因になるわけではない。
albicans(気道叢の正常な部分である生物体)、Cryptococcus neoformans(ときどき気道の正常な叢)および種々のAspergillus種が挙げられる。全身性真菌感染は、内部器官の侵襲性感染である。上記生物体は、通常、肺、消化管または静脈内ラインを通して身体に入る。これらのタイプの感染は、主要な病原性真菌または日和見性真菌により起こる。
Tindall、Great Britain 1983、を参照のこと)に広範に記載され、それらの全体の内容は、本明細書により参考として援用される。前述のリストの各々は、例示的であり、限定するよう意図されていない。
(細胞性壊死のインヒビターを同定するために使用されるスクリーニングアッセイ)
細胞は、最初の攻撃を受けた後、細胞死のアポトーシスの機構、壊死の機構のいずれか、またはアポトーシスの機構および壊死の機構の両方が、活性化され得る。本実施例は、壊死性経路に焦点を絞る。腫瘍壊死因子α(TNF−α)、Fasリガンド、またはβアミロイドタンパク質への曝露を含むいくつかの化学的攻撃を、細胞死を誘導するのに使用した。ヒト神経芽腫(SH−SY5Y)およびヒトJurkat T細胞を含む、種々の細胞タイプをまた、使用した。アポトーシス機構を遮断するために、一般的なカスパーゼインヒビター、N−ベンジルオキシカルボニル−バリン−アラニン−アスパラギン酸−(OMe)フルオロメチルケトン(zVAD、Polverino、A.J.;Patterson、S.D.J.Buiol.Chem.1997、272、7013−7021)を使用した。この化合物は、全てのカスパーゼを阻害し、結果としてアポトーシス経路を分断する。その結果の細胞死は、壊死様機構で起こる(Holler、N.ら、Nature Immunol.2000、1、489−495;Kawahara、A.ら、J.Cell Biol.1998、143、1353−1360)。細胞を壊死性死から救出する試みにおいて、実験化合物をこの細胞に適用した。従って、このプロトコルを使用して細胞生存率を回復することが分かった化合物は、壊死性経路のインヒビターである。
RAW264.7細胞を、抗生物質−抗真菌剤混合物および10%FBSを有するRPMI1640中で維持した。実験1日前に、細胞を96ウェルプレートに5000細胞/ウェルの密度で播いた。細胞を所定の用量のLPSおよび100μM zVAD−fmk(marked「Z」、Q−Biogene)、0.25μg/mlシクロヘキサミド(「C」、それはTNFα、Sigmaにより誘導されるアポトーシス性壊死を増強する)および30μMの化合物893−01で処理した。細胞生存率を、24時間後にCellTiter−Glo ATPアッセイ(Promega)を使用して決定した。生存率を、処理されたウェルの中で生存しているRAW264.7マクロファージの未処理コントロールに対する%で表し、未処理コントロールは図1(LPS、アポトーシスインヒビターzVAD(図1で「Z」と符合したもの)および/またはシクロヘキサミド、アポネクローシス(aponecrosis)増強剤(図1で「C」と符合したもの)処理された細胞)に示されるように100%生存率として設定する。
(2−クロロ−4−メタンスルホニル−6−トリメチルシラニルエチニルフェニルアミンの調製)
(7−クロロ−4−メタンスルホニル−1H−インドールの調製)
(1H−インドール−3−イルメチルージメチルアミンの一般的調製手順で、7−フルオロ−1H−インドール−3−イルメチル)ジメチル−アミンについて例示する)
(2−(1H−インドール−3−イルメチル)−2−ホルミルアミノマロン酸ジエチルエステルの調製のための一般的手順。2−(7−フルオロ−1H−インドール−3−イルメチル)−2−ホルミルアミノマロン酸ジエチルエステルの調製)
(2−(7−クロロ−1−メチル−1H−インドール−3−イルメチル)−2−ホルミルアミノマロン酸ジエチルエステルの調製)
(実施例7)
(トリプトファンの調製の一般的手順、DL−7−フルオロ−トリプトファンについて例示する)
(トリプトファンエステルからの5−(1H−インドール−3−イルメチル)−3−メチル−2−チオキソ−イミダゾリジン−4−オンの調製の一般的手順で、893−01について例示する)
(トリプトファンからの5−(1H−インドール−3−イルメチル)−3−メチル−2−チオキソ−イミダゾリジン−4−オンの調製の一般的手順で、893−01について例示する)
50%ピリジン水溶液(10mL)中のL−トリプトファン(0.408mg、0.002mol.)溶液に、メチルイソチオシアネート(0.175mg、0.0024mol.)を添加し、ついでNaOH(0.5N)を加えてpH(8〜9)にした。その反応混合物を室温で1時間攪拌し、その後石油エーテルで抽出した。水層を濃塩酸で酸性にした。その酸性溶液(pH1.0)を、室温で2日間維持した。その酸性溶液を酢酸エチルで抽出、乾燥および濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーで溶出液として30%酢酸エチル−ヘキサンを使用して精製し、893−01(42mg、8%)を得た:mp144〜148℃。
(5−(1H−インドール−3−イルメチル)−3−(2−モルホリン−4−イル−エチル)−2−チオキソーイミダゾリジン−4−オン(893−17)の調製)
(5−(1H−インドール−3−イルメチル)−2−チオキソ−イミダゾリジン−4−オン(893−18)の調製)
(3−エチル−5−(1H−インドール−3−イルメチル)−イミダゾリジン−2,4−ジオン(893−04)の調製)
(5−(1H−インドール−3−イルメチル)−イミダゾリジン−2,4−ジオン(893−19)の調製
(3−メチル−(5−(1H−インドール−3−イルメチル)−イミダゾリジン−2,4−ジオン(893−20)の調製)
(5−(5−クロロ−ベンゾ[b]チオフェン−3−イルメチル)−3−メチル−イミダゾリジン−2,4−ジオン(893−14)の調製)
(1〜4の調製について使用される手順で、6−クロロインドール−3−カルボキサルデヒド(1)の調製の例示である)
ピペリジン(2ml)中のインドール−3−カルボキシアルデヒド(146mg、1mmol)と1−メチルイミダゾール−2,5(1,3H)−ジオン(Eur.J.Org.Chem.2002、1763〜1769の中で使用される方法に従って合成される)(250mg、2.5mmol)との混合物を、110℃、4時間アルゴン雰囲気下で加熱した。その後、その反応混合物を冷蔵庫(約5℃)にエーテル(2mL)を加えて冷却した。沈殿をろ過し、エーテルで洗浄して、5(171mg、71%)を黄色の個体として得た。
無水MeOH/THF(1:1、40mL)の混合溶媒中の5−(1H−インドール−3−イルメチレン)−3−メチルイミダゾリジン−2,4−ジオン(5)(120mg、0.5mmol)の溶液に、CoCl2(130mg、1.0mmol)およびNaBH4(380mg、10mmol)を、少しづつ添加した。その混合物を、室温で一晩攪拌し、そして酢酸エチルで(100mL)希釈した。その混合物を順に、飽和NaHCO3(30mL)1N HCl(30mL)、飽和NaCl(30mL)で洗浄し、次いで無水MgSO4で乾燥し、ろ過後濃縮した。粗生成物をシリカゲルカラムクロマトグラフィーで50%酢酸エチル/nヘキサンを溶出剤として使用して生成して、893−22を白色固体(80mg、66%)として得た。
(インドールの調製)
(7位に酸素付加したインドールの調製)
((R)−7’−クロロトリプトファン、1および(S)−N−アセチル−7’−クロロトリプトファン、2の調製)
方法A:(S)−N−アセチル−7’−クロルトリプトファンを、3N HCl中で6時間還流しアセチル基を除去した。上記反応混合物の濃縮により、x mgの(S)−7’−クロロトリプトファン(x%)を得た。方法B:(R)−7’−クロロトリプトファンに関する記載と同じ手順を使用して、L−アミノアシラーゼで調製した。
塩化チオニル(0.09mL、1.2mmol)を、0℃で3mLの無水メタノールに溶解し、そしてこの溶液を粗(R)−7’−クロロトリプトファン(200mg、0.5mmol)を含むフラスコに添加した。−5℃で4時間攪拌した後、その反応混合物を室温まで加温し、濃縮前一晩攪拌した。その白色固体を回収し、酢酸エチルで洗浄し、真空で乾燥した。上記生成物をさらに精製することなく直接使用した。
(R)−7’−クロロトリプトファンメチルエステル塩酸塩に、4mLの2.0Mのメチルアミンのメタノール溶液を添加した。その混合物を、室温にてアルゴン雰囲気下で3日間攪拌した。上記反応混合物を濃縮して白色固体の粗生成物を得て、さらに精製することなく直接使用した。
粗(R)−7’−クロロトリプトファンメチルアミド塩酸塩(約0.5mmol)、ピリジン(0.24mL、3.0mmol)、およびジクロロメタン(6mL)の混合物に、アルゴン下でトリホスゲン(178mg、0.6mmol)を、0℃でゆっくり添加した。その反応混合物を0℃で、1時間攪拌し、その後冷却浴を取り除いた。攪拌をアルゴン下、室温で一晩続け、その後120mLの酢酸エチルで希釈した。有機溶液を1N HCl(2×40mL)およびブライン(40mL)で洗浄し、無水MgSO4で乾燥し、ろ過後濃縮した。残渣をシリカゲルクロマトグラフィーで、ヘキサン/酢酸エチル(50:50)を使用して精製し、青白い黄色の固体として27mgの純粋な生成物を得た(全体として収率は20%)。
トリホスゲン(45mg、0.15mmol)を、アルゴン下、0℃で、(S)−7’−クロロトリプトファンメチルアミド塩酸塩(0.28mmol)、ピリジン(0.12mL、1.5mmol)およびジクロロメタン(4mL)の混合物に添加した。上記混合物を0℃で2時間攪拌し、次いで酢酸エチル(100mL)で希釈し、1N HCl(2×30mL)およびブライン(30mL)で洗浄した。有機層を、MgSO4で乾燥し、ろ過後濃縮した。残渣をシリカゲルクロマトグラフィーで、ジクロロメタン/酢酸エチル(85:15)を使用して精製し、青白い黄色の固体として20mgの純粋な生成物(26%)を得た。
(5−ベンゾ[b]チオフェン−3−イルメチル−3−メチル−2−チオキソ−イミダゾリジン−4−オン、893−21の調製)
4mLのピリジン/水(1:1)中の2−アミノ−3−ベンゾ[b]チオフェン−3−イル−プロピオン酸(221mg、1.0mmol)溶液に、メチルチオイソシアネート(80.4mg、1.1mmol)溶液を添加した。得られた混合物を、60℃で18時間攪拌した。その反応混合物を室温まで冷却し、1N HCL(50mL)で希釈し、酢酸エチル(2×40mL)で抽出した。その抽出物を合わせて、ブラインで洗浄し、無水硫酸マグネシウムで乾燥し、ろ過後濃縮し、黄色の固体を得た。その固体を酢酸エチル/ヘキサン/ジクロロメタンの混合物に溶解し、沈殿が生じるまで濃縮した。その混合物をろ過し、青白い黄色の固体として893−21を得た。
(ヒダントインの調製)
(ヒダントインインドール)
以下のヒダントインインドールを実施例16に記載の方法を用いて調製した。
(4−(7−クロロ−1H−インドール−3−イルメチル)−1−メチル−イミダゾリジン−2−オンおよび5−(7−クロロ−1H−インドール−3−イルメチル)−3−メチル−オキサゾリジン−2,4−ジオンの合成)
(4−(7−クロロ−1H−インドール−3−イルメチル)−1−メチル−イミダゾリジン−2−オンおよび5−(7−クロロ−1H−インドール−3−イルメチル)−3−メチル−オキサゾリジン−2,4−ジオンの合成を、ベンジルアミンの代わりにメチルアミンを使用することを除いて、Lewis、R.らの手順(J.Med.Chem.、1995,923)に従って達成した。
(4−(7クロロ−1H−インドール−3−イルメチル)−オキサゾリジン−2−オンの合成)
(5−ベンゾ[b]チオフェン−3−イルメチル−3−メチル−イミダゾリジン−2,4−ジオンの合成)
(一連のヒダントイン化合物およびチオヒダントイン化合物の細胞毒性)
FADD−/−Jurkat細胞(Juo Pら、Cell Growth Differ.1999、10(12):797〜804)を、5*105個の細胞/mLの密度で、各ウェル100μLで、96ウェル白プレート(Costar)に播いた。細胞を2連で異なる濃度の893−10または893−54で処理した。30時間後に、蛍光ATPベース細胞生存率アッセイ(CellTiter−Glo、Promega)を使用して、細胞の生存率を決定した。DMSOで処理したウェルの生存細胞に対する上記化合物で処理したウェルの生存細胞の比率として、毒性値を計算した(図11)。
(5−(7−クロロ−1H−インドール−3−イルメチル)−1,3−ジメチル−イミダゾリジン−2,4ジオンの合成)
5−(7−クロロ−1H−インドール−3−イルメチル)−3−メチルイミダゾリジン−2,4ジオンの合成)
Claims (13)
- 下式の化合物:
Yは、NR8を表し;
Gは、NR7を表し;
R1、R2、およびR3は、独立してH、OH、OR8、F、Cl、Br、I、N(R8)2、COOH、CO2R8、NO2、NHC(O)R8、低級アルキル、置換低級アルキル、またはアリールを表し;
R4は、独立してOH、OR8、F、Cl、Br、I、N(R8)2、COOH、CO2R8、NO2、NHC(O)R8、メチル、メトキシ、低級アルキル、置換低級アルキル、アリール、またはアミンを表し;
R5およびR7は、独立してHまたは低級アルキルを表し;
R6は、低級アルキルを表し;
各R8は、独立してH、低級アルキル、置換低級アルキル、アリール、置換アリール、アリールアルキル、アルケニル、またはアルキニルを表し;
置換されている基は、ハロゲン、アルキル、アラルキル、アルケニル、アルキニル、シクロアルキル、ヒドロキシ、アミノ、ニトロ、スルフヒドリル、イミノ、アミド、ホスホネート、ホスフィネート、カルボニル、カルボキシ、シリル、エーテル、アルキルチオ、スルホニル、ケトン、アルデヒド、エステル、ヘテロシクリル、芳香族部分、ヘテロ芳香族部分、−CF 3 、および−CNから選択される1つ以上の置換基を含む、化合物。 - YがNHを表す、請求項1に記載の化合物。
- R4がCl、Br、F、またはIを表す、請求項2に記載の化合物。
- R6がメチルを表す、請求項6に記載の化合物。
- YおよびGの各々がNHを表す、請求項1に記載の化合物。
- 請求項1〜8のいずれか一項に記載の化合物の立体異性体形態。
- 請求項1〜9のいずれか一項に記載の化合物の薬学的に受容可能な酸付加塩または塩基付加塩。
- 薬学的調製物であって、
(i)請求項1〜8のいずれか一項に記載の化合物、その立体異性体形態、あるいは該化合物またはその立体異性体形態の薬学的に受容可能な酸付加塩または塩基付加塩;および
(ii)薬学的に受容可能なキャリア
を含む、薬学的調製物。 - 請求項11に記載の薬学的調製物であって、前記薬学的に受容可能なキャリアが希釈剤、固体賦形剤および溶媒をカプセル化する物質から選択される、薬学的調製物。
- 請求項11に記載の薬学的調製物であって、前記薬学的に受容可能なキャリアが糖、デンプン、セルロース、粉末化トラガカント、麦芽、ゼラチン、タルク、賦形剤、オイル、グリコール、ポリオール、エステル、寒天、緩衝剤、アルギン酸、発熱物質を含まない水、等張食塩水、リンゲル溶液、エチルアルコール、pH緩衝溶液、ポリエステル、ポリアンヒドリド、およびポリカーボネートからなる群より選択される、薬学的調製物。
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2004
- 2004-08-30 JP JP2006524953A patent/JP2007504171A/ja active Pending
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- 2004-08-30 CA CA2536622A patent/CA2536622C/en not_active Expired - Fee Related
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- 2004-08-30 EP EP16000020.4A patent/EP3081214A3/en not_active Withdrawn
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CA2536622C (en) | 2014-02-11 |
EP1663184A2 (en) | 2006-06-07 |
PL2384753T3 (pl) | 2016-09-30 |
DK2384753T3 (en) | 2016-04-11 |
EP3081214A2 (en) | 2016-10-19 |
US20110144169A1 (en) | 2011-06-16 |
HUE027546T2 (en) | 2016-10-28 |
US20050119260A1 (en) | 2005-06-02 |
US8143300B2 (en) | 2012-03-27 |
AU2004315596B2 (en) | 2011-11-24 |
ES2567135T3 (es) | 2016-04-20 |
US20120149702A1 (en) | 2012-06-14 |
AU2004315596A1 (en) | 2005-08-25 |
EP2384753B1 (en) | 2016-01-06 |
EP2384753A1 (en) | 2011-11-09 |
JP2011157404A (ja) | 2011-08-18 |
US7491743B2 (en) | 2009-02-17 |
WO2005077344A3 (en) | 2006-03-16 |
JP2007504171A (ja) | 2007-03-01 |
WO2005077344A2 (en) | 2005-08-25 |
CA2536622A1 (en) | 2005-08-25 |
SI2384753T1 (sl) | 2016-06-30 |
US8741942B2 (en) | 2014-06-03 |
EP3081214A3 (en) | 2016-11-16 |
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