JP4450620B2 - メラノコルチンレセプターリガンドとしてのn−フェニルピロールグアニジン誘導体 - Google Patents
メラノコルチンレセプターリガンドとしてのn−フェニルピロールグアニジン誘導体 Download PDFInfo
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- JP4450620B2 JP4450620B2 JP2003518518A JP2003518518A JP4450620B2 JP 4450620 B2 JP4450620 B2 JP 4450620B2 JP 2003518518 A JP2003518518 A JP 2003518518A JP 2003518518 A JP2003518518 A JP 2003518518A JP 4450620 B2 JP4450620 B2 JP 4450620B2
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Description
(製造方法)
さらに、前記の定義のような式(I)の化合物の製造方法を提供する。この方法は、式(II)の化合物(式中、X、R1、R2、R3、R4およびR5は、前記の定義の通り)を、それ自体は当該技術分野において周知である手順を用い、アミノグアニジン(III)またはその塩もしくは保護形態(protected form)と反応させ、必要または希望に応じて脱保護して式(I)の化合物を得るものである。
(実施例)
(実施例1)
5g(24.3mmol)の1-(4-chlorophenyl)-pyrrol-2-carboxaldehydeと4.96g(36.5mmol)の重炭酸アミノグアニジンとを、500mlのアセトニトリル中に懸濁させた。120mlの酢酸を加え、その反応混合物を2時間還流させた。その溶液を冷却し、溶媒をエバポレートした。その結果得られた粗生成物をエーテルに溶解し、フリーザに4時間置いた後、結晶化させた。わずかに黄色のその固体を、アセトニトリル/エタノール(5:1)から再結晶し、白色の結晶である純粋生成物(1)を得た。収量は3g(45%)であった。
(化合物1〜50)
番号 化合物名
1 N-[[1-(4-クロロフェニル)-1H-ピロール-2-イル]メチレンアミノ]グアニジン
N-[1-[(4-Chlorophenyl)-1H-Pyrrol-2-yl]methyleneamino]guanidine
2 N-[1-(5-propylamino-1-(2-butoxy-phenyl)-1H-pyrrol-2-yl)-methyleneamino]-guanidine
3 N-[3-[1-(2-Isobutyryl-phenyl)-5-nitro-1H-pyrrol-2-yl]-propylideneamino]-guanidine
4 N-[1-[1-(3-Cyanophenyl)-5-trifluoromethyl-1H-pyrrol-2-yl]-methyleneamino]-guanidine
5 N-[3-[1-(3-Fluorophenyl)-5-methyl-1H-pyrrol-3-yl]-propylideneamino]-guanidine
6 N-[1-(4-Aminophenyl)-5-hydroxy-1H-pyrrol-2-ylmethylideneamino]-guanidine
7 N-[3-[1-(4-Chlorophenyl)-5-phenethyl-1H-pyrrol-3-yl]-propylideneamino]-guanidine
8 N-[3-[1-(4-Propylaminophenyl)-5-trichloromethyl-1H-pyrrol-3-yl]-propylideneamino]-guanidine
9 N-(5-tert-Butyl-1-phenyl-1H-pyrrol-2-ylmethylideneamino)-guanidine
10 N-[3-(5-Methoxy-1-phenyl-1H-pyrrol-3-yl)-propylideneamino]-guanidine
11 N-[4-Pentyl-1-(2-trichloromethylphenyl)-1H-pyrrol-3-ylmethylideneamino]-guanidine
12 N-(4-Cyano-1-o-tolyl-1H-pyrrol-3-ylmethylideneamino)-guanidine
13 N-[3-[4-Hydroxy-1-(3-trichloromethylphenyl)-1H-pyrrol-2-yl]-propylideneamino]-guanidine
14 N-[3-[1-(3-tert-Butylphenyl)-5-isobutyryl-1H-pyrrol-2-yl]-propylideneamino]-guanidine
15 N-(1-Biphenyl-4-yl-4-chloro-1H-pyrrol-2-ylmethylideneamino)-guanidine
16 N-[3-[1-(4-Bromophenyl)-4-tert-butyl-1H-pyrrol-3-yl]-propylideneamino]-guanidine
17 N-(4-Butoxy-1-phenyl-1H-pyrrol-3-ylmethylideneamino)-guanidine
18 N-[3-(4-Methoxy-1-phenyl-1H-pyrrol-2-yl)-propylideneamino]-guanidine
19 N-[3-[1-(2-Nitrophenyl)-1H-pyrrol-2-yl]-propylideneamino]-guanidine
20 N-[3-[1-(2-Hydroxyphenyl)-1H-pyrrol-2-yl]-propylideneamino]-guanidine
21 N-[1-(3-Methoxyphenyl)-1H-pyrrol-2-ylmethylideneamino]-guanidine
22 N-[1-(3-Butylaminophenyl)-1H-pyrrol-3-ylmethylideneamino]-guanidine
23 N-[1-(4-tert-Butylphenyl)-1H-pyrrol-3-ylmethylideneamino]-guanidine
24 N-[3-[1-(4-トリフルオロメチルフェニル)-1H-ピロール-2-イル]-プロピリデンアミノ]-グアニジン
N-[3-[1-(4-Trifluoromethylphenyl)-1H-pyrrol-2-yl]-propylideneamino]-guanidine
25 N-(1-Phenyl-1H-pyrrol-3-ylmethylideneamino)-guanidine
26 N-[3-(1-フェニル-1H-ピロール-2-イル)-プロピリデンアミノ]-グアニジン
N-[3-(1-Phenyl-1H-pyrrol-2-yl)-propylideneamino]-guanidine
29 N-[3-(4-Methyl-1-phenyl-1H-pyrrol-3-yl)-propylideneamino]-guanidine
30 N-[1-(3-Nitro-4-propylaminophenyl)-1H-pyrrol-3-ylmethylideneamino]-guanidine
31 N-[3-[1-(3-Butylamino-4-methylphenyl)-4-methyl-1H-pyrrol-2-yl]-propylidene]-guanidine
32 N-[3-[5-Bromo-1-(4-bromophenyl)-1H-pyrrol-3-yl]-propylideneamino]-guanidine
33 N-[(5-Chloro-1-(4-isobutyrylphenyl)-4-pentyl-1H-pyrrol-2-yl)methyleneamino]-guanidine
34 N-[3-(5-Propoxy-1-m-tolyl-1H-pyrrol-2-yl)-propylideneamino]-guanidine
35 N-[4-Methyl-5-propylamino-1-(3-trichloromethylphenyl)-1H-pyrrol-3-ylmethylideneamino]-guanidine
36 N-[3-[1-(3-Nitrobiphenyl-4-yl)-1H-pyrrol-2-yl]-propylideneamino]-guanidine
37 N-[2-[4-tert-Butyl-1-(4-methoxy-2-propylaminophenyl)-1H-pyrrol-3-yl]-ethylideneamino]-guanidine
38 N-[3-[1-(2-Bromo-3-chlorophenyl)-1H-pyrrol-3-yl]-propylideneamino]-guanidine
39 N-[4-Bromo-1-(2-butoxy-3-propoxyphenyl)-1H-pyrrol-2-ylmethylideneamino]-guanidine
40 N-[5-Hydroxy-1-(2-hydroxyphenyl)-1H-pyrrol-3-ylmethylideneamino]-guanidine
41 N-[3-[1-(2-tert-Butylphenyl)-4-chloro-5-methyl-1H-pyrrol-2-yl]-propylideneamino]-guanidine
42 N-[5-Isobutyryl-1-(2,3,4-trimethoxyphenyl)-1H-pyrrol-2-ylmethylideneamino]-guanidine
43 N-[3-[5-tert-Butyl-1-(2-tert-butyl-3,4-bis-trichloromethylphenyl)-4-trichloromethyl-1H-pyrrol-2-yl]-propylideneamino]-guanidine
44 N-[2-[1-(4-Pyrrol-1-ylphenyl)-1H-pyrrol-2-yl]-ethylideneamino]-guanidine
45 N-[1-(4-Morpholin-4-yl-phenyl)-1H-pyrrol-2-ylmethylideneamino]-guanidine
46 N-[1-(4-Pyrrolidin-1-yl-phenyl)-1H-pyrrol-3-ylmethylidenamino]-guanidine
47 N-((1-フェニル-1H-ピロール-2-イル)メチレンアミノ)グアニジン
N-((1-Phenyl-1H-pyrrol-2-yl)methyleneamino)guanidine
48 N-[(1-(4-トリフルオロメチルフェニル)-1H-ピロール-2-イル)メチレンアミノ]グアニジン
N-[(1-(4-Trifluoromethylphenyl)-1H-pyrrol-2-yl)methyleneamino]guanidine
49 N-[(1-(3-cyanophenyl)-1H-pyrrol-2-yl)methyleneamino]guanidine
50 N-[(1-(3,5-ジクロロフェニル)-1H-ピロール-2-イル)メチレンアミノ]グアニジン
N-[(1-(3,5-dichlorophenyl)-1H-pyrrol-2-yl)methyleneamino]guanidine
(試験1.MC1-レセプターへの親和性)
この結合アッセイは、I125-NDP-αMSHをリガンドとして用い、本質的にLunec et al., Melanoma Res. 1992; 2; 5-12の記述通りに行った。
この結合アッセイは、I125-NDP-αMSHをリガンドとして用い、本質的にSzardenings et al., J. Biol. Chem. 1997; 272; 27943-27948 および Schioeth et al., FEBS Lett. 1997; 410; 223-228の記述通りに行った。
このcAMPの刺激は、本質的にSchioeth et al., Br J Pharmacol 1998; 124; 75-82の記述通りに行った。ただし、α-MSHと相対的な応答を観察した。
化合物群を、ラットの食物摂取および体重に対するそれらの効果について試験した。
ラットは、上述の通りにカニューレを挿入した。それらは、予備的飢餓なしに用い、そして、化合物群は、午後5時に、全体積5mlで投与した。使用した化合物2:4の用量は、1、4および10nmolであった。食物摂取は、投与の3、15および24時間後に測定し、そして、体重は24時間時に記録した。比較のために、周知のMC4レセプターアゴニストであるメラノタンII(Melanotan II (MTII))を用量1nmolで使用した。
{対照}
雌のBALB/cマウス達(体重20〜22g)を、剃毛した腹部を30μlの0.5%2,4−ジニトロフルオロベンゼン(DNFB)で処理して感作した(sensitized)。4日後、それらの足に10μlの0.3%DNFBでチャレンジした(challenged)。チャレンジしなかったマウスの足を対照として供した。最終のチャレンジから24時間後、足重量の相違を、炎症(足のむくみ)の指標として測定した。
マウス達を対照として処理したが、さらにα-MSH(0.5mg/kg)またはプレドニゾロン(20mg/kg)を、感作(第0日)の2時間前に腹膜腔内へ(i.p.)注入し、そして、それに等しい用量を、感作後に連続して4日間、繰り返し投与した。足のむくみの阻害は、上述と同様に測定した。
マウス達を対照として処理したが、さらに種々の用量(0.05、0.15または0.25、0.375、0.5および0.75mg/kg)の各化合物を、感作(第0日)の2時間前に腹膜腔内へ(i.p.)注入し、そして、それに等しい用量を、感作後に連続して4日間、繰り返し投与した。足のむくみの阻害は、上述と同様に測定した。
カプセル毎
活性成分、塩として 5mg
ラクトース 250mg
デンプン 120mg
ステアリン酸マグネシウム 5mg
全量 380mg
(好適な錠剤である製剤の実施例)
錠剤毎
活性成分、塩として 5mg
ポテトスターチ 90mg
コロイドシリカ 10mg
タルク 20mg
ステアリン酸マグネシウム 2mg
ゼラチン5%水溶液 25mg
全量 152mg
Claims (33)
- 置換基R1、R2、R3、R4およびR5のうち少なくとも2つが水素である請求項1に記載の化合物。
- ハロゲンがフルオロ、クロロまたはブロモから選択される請求項1または2に記載の化合物。
- n=0である請求項1〜3のいずれかに記載の化合物。
- R5が水素である請求項1〜4のいずれかに記載の化合物。
- R3が水素である請求項1〜5のいずれかに記載の化合物。
- R4が水素である請求項1〜6のいずれかに記載の化合物。
- R1およびR2がフェニル環の3位、4位または5位に位置する請求項1〜7のいずれかに記載の化合物。
- R2が水素である請求項1〜8のいずれかに記載の化合物。
- R1がフェニル環の4位にある請求項1〜9のいずれかに記載の化合物。
- ハロゲンが、クロロまたはブロモから選択される請求項1〜10のいずれかに記載の化合物。
- ハロゲンが、クロロである請求項11に記載の化合物。
- 下記名前のうちいずれか一つを有する請求項1に記載の化合物または薬理学的に許容可能なその塩。
番号 化合物名
1 N-[[1-(4-クロロフェニル)-1H-ピロール-2-イル]メチレンアミノ]グアニジン
(N-[[1-(4-Chlorophenyl)-1H-Pyrrol-2-yl]methyleneamino]guanidine)
24 N-[3-[1-(4-トリフルオロメチルフェニル)-1H-ピロール-2-イル]-プロピリデンアミノ]-グアニジン
(N-[3-[1-(4-Trifluoromethylphenyl)-1H-pyrrol-2-yl]-propylideneamino]-guanidine)
26 N-[3-(1-フェニル-1H-ピロール-2-イル)-プロピリデンアミノ]-グアニジン
(N-[3-(1-Phenyl-1H-pyrrol-2-yl)-propylideneamino]-guanidine)
47 N-((1-フェニル-1H-ピロール-2-イル)メチレンアミノ)グアニジン
(N-((1-Phenyl-1H-pyrrol-2-yl)methyleneamino)guanidine)
48 N-[(1-(4-トリフルオロメチルフェニル)-1H-ピロール-2-イル)メチレンアミノ]グアニジン
(N-[(1-(4-Trifluoromethylphenyl)-1H-pyrrol-2-yl)methyleneamino]guanidine)
50 N-[(1-(3,5-ジクロロフェニル)-1H-ピロール-2-イル)メチレンアミノ]グアニジン
(N-[(1-(3,5-dichlorophenyl)-1H-pyrrol-2-yl)methyleneamino]guanidine) - 請求項1〜13のいずれか1項に記載の化合物と、1以上の佐剤(adjuvants)、担体または賦形剤とを含む医薬品組成物。
- 治療に用いる請求項1〜13のいずれか1項に記載の化合物。
- 請求項1〜13のいずれか1項に記載の化合物を含む、炎症の治療薬。
- 請求項1〜13のいずれか1項に記載の化合物を含む、精神障害(disorders)の治療薬。
- 請求項1〜13のいずれか1項に記載の化合物を含む、内分泌系またはホルモン系における機能不全の治療薬。
- 請求項1〜13のいずれか1項に記載の化合物を含む、性機能および/または性機能不全の治療薬。
- 請求項1〜13のいずれか1項に記載の化合物を含む、アレルギー性疾患(disorders)の治療薬。
- 請求項1〜13のいずれか1項に記載の化合物を含む、心血管系における障害の治療薬。
- 請求項1〜13のいずれか1項に記載の化合物を含む、痛みの治療薬。
- 請求項1〜13のいずれか1項に記載の化合物を含む、皮膚の日焼けまたは皮膚の淡色化を誘発する薬。
- 請求項1〜13のいずれか1項に記載の化合物を含む、II型糖尿病の治療薬。
- 請求項1〜13のいずれか1項に記載の化合物を含む、肥満の治療薬。
- 請求項1〜13のいずれか1項に記載の化合物を含む、食欲不振の治療薬。
- 前記食欲不振が、癌、カヘキシー、高齢(geriatric conditions)、HIV、外傷、および心理状態に起因する食欲不振である請求項27に記載の治療薬。
- 請求項1〜13のいずれか1項に記載の化合物を含む、皮膚障害の治療薬。
- 前記皮膚障害が、黒色腫である請求項29に記載の治療薬。
- 請求項1〜13のいずれか1項に記載の化合物を含む、悪性腫瘍の治療および/または診断のための薬。
- 前記悪性腫瘍が、黒色腫である請求項31に記載の薬。
- 請求項1〜13のいずれか1項に記載の化合物を含む、虚血および/または虚血/再灌流の治療薬。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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GBGB0119172.5A GB0119172D0 (en) | 2001-08-06 | 2001-08-06 | Phenyl pyrrole derivatives |
PCT/GB2002/003620 WO2003013509A1 (en) | 2001-08-06 | 2002-08-06 | N-phenylpyrrole guanidine derivatives as melanocortin reception ligands |
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JP2005504039A JP2005504039A (ja) | 2005-02-10 |
JP2005504039A5 JP2005504039A5 (ja) | 2006-01-12 |
JP4450620B2 true JP4450620B2 (ja) | 2010-04-14 |
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JP2009143997A Withdrawn JP2009242414A (ja) | 2001-08-06 | 2009-06-17 | メラノコルチンレセプターリガンドとしてのn−フェニルピロールグアニジン誘導体 |
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EP (1) | EP1414440B1 (ja) |
JP (2) | JP4450620B2 (ja) |
KR (1) | KR20040019302A (ja) |
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GB (1) | GB0119172D0 (ja) |
IL (1) | IL160181A0 (ja) |
MX (1) | MXPA04001037A (ja) |
NO (1) | NO20040465L (ja) |
NZ (1) | NZ529666A (ja) |
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-
2001
- 2001-08-06 GB GBGB0119172.5A patent/GB0119172D0/en not_active Ceased
-
2002
- 2002-08-06 IL IL16018102A patent/IL160181A0/xx unknown
- 2002-08-06 SI SI200230506T patent/SI1414440T1/sl unknown
- 2002-08-06 JP JP2003518518A patent/JP4450620B2/ja not_active Expired - Fee Related
- 2002-08-06 NZ NZ529666A patent/NZ529666A/en not_active IP Right Cessation
- 2002-08-06 WO PCT/GB2002/003620 patent/WO2003013509A1/en active IP Right Grant
- 2002-08-06 US US10/484,444 patent/US7186748B2/en not_active Expired - Fee Related
- 2002-08-06 MX MXPA04001037A patent/MXPA04001037A/es unknown
- 2002-08-06 DK DK02753136T patent/DK1414440T3/da active
- 2002-08-06 BR BR0210445-8A patent/BR0210445A/pt not_active IP Right Cessation
- 2002-08-06 KR KR10-2003-7016099A patent/KR20040019302A/ko not_active Application Discontinuation
- 2002-08-06 AU AU2002313542A patent/AU2002313542B2/en not_active Ceased
- 2002-08-06 EP EP02753136A patent/EP1414440B1/en not_active Expired - Lifetime
- 2002-08-06 ES ES02753136T patent/ES2280555T3/es not_active Expired - Lifetime
- 2002-08-06 CA CA2448356A patent/CA2448356C/en not_active Expired - Fee Related
- 2002-08-06 PT PT02753136T patent/PT1414440E/pt unknown
- 2002-08-06 DE DE60217503T patent/DE60217503T2/de not_active Expired - Lifetime
-
2004
- 2004-02-02 NO NO20040465A patent/NO20040465L/no not_active Application Discontinuation
-
2006
- 2006-03-15 US US11/374,956 patent/US7442807B2/en not_active Expired - Fee Related
-
2007
- 2007-03-30 CY CY20071100446T patent/CY1106424T1/el unknown
-
2008
- 2008-09-17 US US12/232,399 patent/US20090018183A1/en not_active Abandoned
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2009
- 2009-06-17 JP JP2009143997A patent/JP2009242414A/ja not_active Withdrawn
Also Published As
Publication number | Publication date |
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ES2280555T3 (es) | 2007-09-16 |
JP2009242414A (ja) | 2009-10-22 |
SI1414440T1 (sl) | 2007-06-30 |
KR20040019302A (ko) | 2004-03-05 |
BR0210445A (pt) | 2004-08-17 |
US7186748B2 (en) | 2007-03-06 |
CA2448356A1 (en) | 2003-02-20 |
CY1106424T1 (el) | 2011-10-12 |
IL160181A0 (en) | 2004-07-25 |
WO2003013509A1 (en) | 2003-02-20 |
EP1414440B1 (en) | 2007-01-10 |
AU2002313542B2 (en) | 2007-03-22 |
NZ529666A (en) | 2006-04-28 |
US20040254093A1 (en) | 2004-12-16 |
US7442807B2 (en) | 2008-10-28 |
CA2448356C (en) | 2010-04-20 |
NO20040465L (no) | 2004-02-02 |
US20090018183A1 (en) | 2009-01-15 |
US20060148798A1 (en) | 2006-07-06 |
PT1414440E (pt) | 2007-04-30 |
MXPA04001037A (es) | 2004-06-03 |
GB0119172D0 (en) | 2001-09-26 |
DK1414440T3 (da) | 2007-05-21 |
JP2005504039A (ja) | 2005-02-10 |
EP1414440A1 (en) | 2004-05-06 |
DE60217503T2 (de) | 2007-08-09 |
DE60217503D1 (de) | 2007-02-22 |
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