JP2000512995A - イミダゾキノリンアミン調製方法 - Google Patents
イミダゾキノリンアミン調製方法Info
- Publication number
- JP2000512995A JP2000512995A JP10502898A JP50289898A JP2000512995A JP 2000512995 A JP2000512995 A JP 2000512995A JP 10502898 A JP10502898 A JP 10502898A JP 50289898 A JP50289898 A JP 50289898A JP 2000512995 A JP2000512995 A JP 2000512995A
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- carbon atoms
- imidazo
- amine
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1. (i) テトラゾロ[1,5-a]キノリン-5-オールを提供するステップと (ii) ステップ(i)からの化合物をニトロ化して、4-ニトロテトラ ゾロ[1,5-a]キノリン-5-オールを提供するステップとを含む化学物質を調製す る方法。 2. (iii) ステップ(ii)からの化合物をスルホニル化して、4-ニトロテ トラゾロ[1,5-a]キノリン-5-スルホネートを提供するステップをさらに含む請 求項1に記載の方法。 3. (iv) ステップ(iii)からの化合物をアミンと反応させ、(5-置換 )-4-ニトロテトラゾロ[1,5-a]キノリン-5-アミンを提供するステップをさら に含む請求項2に記載の方法。 4. (v) ステップ(iv)からの化合物を還元して、(5-置換)テトラゾ ロ[1,5-a]キノリン-4,5-ジアミンを提供するステップをさらに含む請求項3に記 載の方法。 5. (vi) ステップ(v)からの化合物をカルボン酸またはその相当物と反 応させて、(5-置換)(6-置換)6H-イミダゾ[4,5-c]テトラゾロ[1,5-a]キノ リンを提供するステップをさらに含む請求項4に記載の方法。 6. (vii) ステップ(vi)からの化合物をトリフェニルホスフィンと反応 させて、(1-置換)(2-置換)N-トリフェニルホス フィニル-1H-イミダゾ[4,5-c]キノリン-4-アミンを提供するステップをさらに 含む請求項5に記載の方法。 7. (viii) ステップ(vii)からの化合物を加水分解して、(1-置換 )(2-置換)1H-イミダゾ[4,5-c]キノリン-4-アミンを提供するステップと、 (xi) (1-置換)(2-置換)1H-イミダゾ[4,5-c]キノリン-4-アミン または薬理学的に認容できるその付加塩を分離するステップをさらに含む請求項 6に記載の方法。 8. (i) (4-置換)アミノ-2-クロロ-3-ニトロキノリンを提供するス テップと、 (ii) ステップ(i)からの化合物をアジ化ナトリウムと反応させて、 (5-置換)-4-ニトロテトラゾロ[1,5-a]キノリン-5-アミンを提供するステッ プを含む化学物質を調製する方法。 9. (iii) ステップ(ii)からの化合物を還元して、(5-置換)テトラゾ ロ[1,5-a]キノリン-4,5-ジアミンを提供するステップをさらに含む請求項8に記 載の方法。 10. (iv) ステップ(iii)からの化合物をカルボン酸またはその相当物と 反応させて、(5-置換)(6-置換)6H-イミダゾ[4,5-c]テトラゾロ[1,5-a]キ ノリンを提供するステップをさらに含む請求項9に記載の方法。 11.(v) ステップ(iv)からの化合物をトリフェニルホスフィンと反応さ せて、(1-置換)(2-置換)N-トリフェニルホス フィニル-1H-イミダゾ[4,5-c]キノリン-4-アミンを提供するステップをさらに 含む請求項10に記載の方法。 12. (vi) ステップ(v)からの化合物を加水分解して、(1-置換)(2- 置換)1H-イミダゾ[4,5-c]キノリン-4-アミンを提供するステップと、 (vii) (1-置換)(2-置換)1H-イミダゾ[4,5-c]キノリン-4-アミ ンまたは薬理学的に認容できるその付加塩を分離するステップをさらに含む請求 項11に記載の方法。 13. (i) (1-置換)(2-置換)4-クロロ-1H-イミダゾ[4,5-c]キノリ ンを提供するステップと、 (ii) ステップ(i)からの化合物とヒドラジンを反応させて、(1- 置換)(2-置換)4-ヒドラジノ-1H-イミダゾ[4,5-c]キノリンを提供するステ ップを含む化学物質を調製する方法。 14. (iii) ステップ(ii)からの化合物を亜硝酸ナトリウムと反応させて 、(5-置換)(6-置換)6H-イミダゾ[4,5-c]テトラゾロ[1,5-a]キノリンを提 供するステップをさらに含む請求項13に記載の方法。 15. (iv) ステップ(iii)からの化合物をトリフェニルホスフィンと反応 させて、(1-置換)(2-置換)N-トリフェニルホスフィニル-1H-イミダゾ[4, 5-c]キノリン-4-アミンを提供するステップをさらに含む請求項14に記載の方法 。 16. (v) ステップ(iv)からの化合物を加水分解して、(1-置換)(2 -置換)1H-イミダゾ[4,5-c]キノリン-4-アミンを提供するステップと、 (vi) (1-置換)(2-置換)1H-イミダゾ[4,5-c]キノリン-4-アミ ンまたは薬理学的に認容できるその付加塩を分離するステップをさらに含む請求 項15に記載の方法。 17. (i) (5-置換)(6-置換)6H-イミダゾ[4,5-c]テトラゾロ[1,5-a] キノリンを提供するステップと、 (ii) ステップ(i)からの化合物をトリフェニルホスフィンと反応さ せて、(1-置換)(2-置換)N-トリフェニルホスフィニル-1H-イミダゾ[4,5- c]キノリン-4-アミンを提供するステップを含む化学物質を調製する方法。 18. (iii) ステップ(ii)からの化合物を加水分解して、(1-置換)(2 -置換)1H-イミダゾ[4,5-c]キノリン-4-アミンを提供するステップと、 (vi) (1-置換)(2-置換)1H-イミダゾ[4,5-c]キノリン-4-アミ ンまたは薬理学的に認容できるその付加塩を分離するステップをさらに含む請求 項17に記載の方法。 19. (1-置換)(2-置換)1H-イミダゾ[4,5-c]キノリン-4-アミンが、1- (2-メチルプロピル)-1H-イミダゾ[4,5-c]キノリン-4-アミンである請求項7 に記載の方法。 20. (1-置換)(2-置換)1H-イミダゾ[4,5-c]キノリン-4-アミンが、1- (2-メチルプロピル)-1H-イミダゾ[4,5-c]キノリン-4-アミンである請求項12 に記載の方法。 21. (1-置換)(2-置換)1H-イミダゾ[4,5-c]キノリン-4-アミンが、1- (2-メチルプロピル)-1H-イミダゾ[4,5-c]キノリン-4-アミンである請求項16 に記載の方法。 22. (1-置換)(2-置換)1H-イミダゾ[4,5-c]キノリン-4-アミンが、1- (2-メチルプロピル)-1H-イミダゾ[4,5-c]キノリン-4-アミンである請求項18 に記載の方法。 23.化合物4-ニトロテトラゾロ[1,5-a]キノリン-5-オール。 24.式III、 (式中、R'は、アルキル、ハロアルキルおよびアリールからなる群より選択さ れる。)を有する化合物。 25.R'が、トリフルオロメチルである請求項24に記載の化合物。 26.式IV、 (式中、R1は、1〜約6個の炭素原子を有するアルキルと、アルキル部分が1 〜約6個の炭素原子を含有するヒドロキシアルキルと、アルキル部分が1〜約3 個の炭素原子を含有するアリールアルキルとからなる群より選択される。)を有 する化合物。 27.R1が、2-メチルプロピル、2-ヒドロキシ-2-メチルプロピル、ベンジ ルおよびフェニルエチルからなる群より選択される請求項26に記載の化合物。 28.R1が、2-メチルプロピルである請求項27に記載の化合物。 29.式V、(式中、R1は、1〜約6個の炭素原子を有するアルキルと、アルキル部分が1 〜約6個の炭素原子を含有するヒドロキシアルキルと、アルキル部分が1〜約3 個の炭素原子を含有するアリールアルキルとからなる群より選択される。)を有 する化合物。 30.R1が、2-メチルプロピル、2-ヒドロキシ-2-メチルプロピル、ベンジ ルおよびフェニルエチルからなる群より選択される請求項29に記載の化合物。 31.R1が、2-メチルプロピルである請求項30に記載の化合物。 32.式VI、 (式中、R1は、水素と、1〜約6個の炭素原子を有するアルキルと、アルキル 部分が1〜約6個の炭素原子を含有するヒドロキシアルキルと、アルキル部分が 1〜約3個の炭素原子を含有するアリールアルキルとからなる群より選択され、 R2は、水素と、1〜約4個の炭素原子を有するアルキルと、アルコキシ部分が 1〜約4個の炭素原子を含有し、アルキル部分が1〜約4個の炭素原子を含有す るアルコキシアルキルと、アルキル部分が1〜約4個の炭素原子を 含有するヒドロキシルアルキルと、アルキル部分が1〜約4個の炭素原子を含有 するハロアルキルと、アリールオキシメチルとからなる群より選択される。)を 有する化合物。 33.R1が、水素、2-メチルプロピル、2-ヒドロキシ-2-メチルプロピル、 ベンジルおよびフェニルエチルからなる群より選択される請求項32に記載の化合 物。 34.R2が、水素、メチル、エトキシメチル、およびベンジルからなる群より 選択される請求項32に記載の化合物。 35.R1が2-メチルプロピルであり、R2が水素である請求項32に記載の化合 物。 36.R1が水素であり、R2が水素である請求項32に記載の化合物。 37.式VII、 (式中、R1は、水素と、1〜約6個の炭素原子を有するアルキルと、アルキル 部分が1〜約6個の炭素原子を含有するヒドロキシア ルキルと、アルキル部分が1〜約3個の炭素原子を含有するアリールアルキルと からなる群より選択され、R2は、水素と、1〜約4個の炭素原子を有するアル キルと、アルコキシ部分が1〜約4個の炭素原子を含有し、アルキル部分が1〜 約4個の炭素原子を含有するアルコキシアルキルと、アルキル部分が1〜約4個 の炭素原子を含有するヒドロキシルアルキルと、アルキル部分が1〜約4個の炭 素原子を含有するハロアルキルと、アリールオキシメチルとからなる群より選択 される。)を有する化合物。 38.R1が、水素、2-メチルプロピル、2-ヒドロキシ-2-メチルプロピル、 ベンジルおよびフェニルエチルからなる群より選択され、R2が、水素、メチル 、エトキシメチル、およびベンジルからなる群より選択される請求項37に記載 の化合物。 39.R1が、2-メチルプロピルであり、R2が水素である請求項38に記載の化 合物。 40.式XI、 (式中、R1は、水素と、1〜約6個の炭素原子を有するアルキルと、アルキル 部分が1〜約6個の炭素原子を含有するヒドロキシアルキルと、アルキル部分が 1〜約3個の炭素原子を含有するアリールアルキルとからなる群より選択され、 R2は、水素と、1〜約4個の炭素原子を有するアルキルと、アルコキシ部分が 1〜約4個の炭素原子を含有し、アルキル部分が1〜約4個の炭素原子を含有す るアルコキシアルキルと、アルキル部分が1〜約4個の炭素原子を含有するヒド ロキシルアルキルと、アルキル部分が1〜約4個の炭素原子を含有するハロアル キルと、アリールオキシメチルとからなる群より選択される。)を有する化合物 。 41.R1が、水素、2-メチルプロピル、2-ヒドロキシ-2-メチルプロピル、 ベンジルおよびフェニルエチルからなる群より選択され、R2が、水素、メチル 、エトキシメチル、およびベンジルからなる群より選択される請求項40に記載の 化合物。 42.R1が2-メチルプロピルであり、R2が水素である請求項41に記載の化合 物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/673,712 US5741908A (en) | 1996-06-21 | 1996-06-21 | Process for reparing imidazoquinolinamines |
US08/673,712 | 1996-06-21 | ||
PCT/US1996/016972 WO1997048704A1 (en) | 1996-06-21 | 1996-10-22 | Process for preparing imidazoquinolinamines |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2000512995A true JP2000512995A (ja) | 2000-10-03 |
JP2000512995A5 JP2000512995A5 (ja) | 2004-10-28 |
JP4139915B2 JP4139915B2 (ja) | 2008-08-27 |
Family
ID=24703817
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP50289898A Expired - Fee Related JP4139915B2 (ja) | 1996-06-21 | 1996-10-22 | イミダゾキノリンアミン調製方法 |
Country Status (15)
Country | Link |
---|---|
US (9) | US5741908A (ja) |
EP (1) | EP0912565B1 (ja) |
JP (1) | JP4139915B2 (ja) |
KR (3) | KR20040029477A (ja) |
AT (1) | ATE264326T1 (ja) |
AU (1) | AU721036B2 (ja) |
CA (1) | CA2257846C (ja) |
DE (1) | DE69632207T2 (ja) |
DK (1) | DK0912565T3 (ja) |
ES (1) | ES2215203T3 (ja) |
IL (5) | IL127348A (ja) |
NO (4) | NO316564B1 (ja) |
NZ (1) | NZ333169A (ja) |
PT (1) | PT912565E (ja) |
WO (1) | WO1997048704A1 (ja) |
Cited By (1)
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JP2007506788A (ja) * | 2003-09-26 | 2007-03-22 | ライジェル ファーマシューティカルズ, インコーポレイテッド | Hcv感染阻害剤とその使用法 |
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- 1996-10-22 EP EP96946380A patent/EP0912565B1/en not_active Expired - Lifetime
- 1996-10-22 KR KR10-2004-7003625A patent/KR20040029476A/ko not_active Application Discontinuation
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- 1996-10-22 PT PT96946380T patent/PT912565E/pt unknown
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2007506788A (ja) * | 2003-09-26 | 2007-03-22 | ライジェル ファーマシューティカルズ, インコーポレイテッド | Hcv感染阻害剤とその使用法 |
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