JP5683396B2 - ベンジリデンアミノグアニジンおよびヒドロキシグアニジンのメラノコルチン受容体リガンドとしての使用 - Google Patents
ベンジリデンアミノグアニジンおよびヒドロキシグアニジンのメラノコルチン受容体リガンドとしての使用 Download PDFInfo
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- JP5683396B2 JP5683396B2 JP2011148414A JP2011148414A JP5683396B2 JP 5683396 B2 JP5683396 B2 JP 5683396B2 JP 2011148414 A JP2011148414 A JP 2011148414A JP 2011148414 A JP2011148414 A JP 2011148414A JP 5683396 B2 JP5683396 B2 JP 5683396B2
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- Prior art keywords
- nitrobenzylideneamino
- hydroxyguanidine tosylate
- treatment
- hydroxyguanidine
- compound
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- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
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- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
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Description
R1、R2、R3、R4、およびR5は、同じであっても異なっていてもよく、水素、ハロゲン、炭素原子を1〜5個有するアルキル、例えば、炭素原子を1〜5個有するアルコキシまたはヒドロキシのような電子供与基、シアノ、ニトロ、トリフルオロアルキル、またはアミドから選択される電子受容基、アルキルアミノ、ベンゾイルオキシ、ニトロキシ、フェニル、またはスルホから選択される。
[調製方法]
一般式(I)で表される化合物は、以下に述べるような一般的方法で調製してもよい。
(方法1)
以下に示す実施例において挙げる化合物は、意図した用途において特に有用なものであるが、これらの実施例はあくまで説明目的に示すものであり、本発明の請求の範囲を何ら限定するものではない。実施例中の化合物にはa:bのような番号コードを付与しているが、aはその化合物の調製について記載している実施例の番号を表し、bはその化合物が該実施例中で調製された順番を表している。したがって、1:2というコードが付与された化合物の例は、方法1(実施例1参照)によって2番目に調製された化合物を意味する。
IR、NMR、MS、および元素分析により、化合物の構造を確認した。融点(mp)を記載している場合、未補正値を示している。
2−クロロ−3,4−ジメトキシベンズアルデヒド(1.0g、5mmol)、重炭酸アミノグアニジン(0.68g、5mmol)、および酢酸(1ml)をメタノール15ml中に溶解させた溶液を、10分間加熱還流した。得られた反応液を0℃まで冷却し、残留物をろ過により除去した。真空状態でろ液を蒸発させ、得られた生成物をエタノールから晶出(crystallised)させた。目的の化合物1:1の収量は1.1g(70%)であり、その融点は198〜200℃であった。
化合物1:2〜1:164を、上述の方法1を用い、基本的には化合物1:1の調製と同様の手法によって調製した。これら化合物を、データと共に以下に示す。
1 N−(2−クロロ−3,4−ジメトキシベンジリデンアミノ)グアニジンアセテート、mp:198〜200℃
2 N−(3−ブロモベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:177〜178.5℃
3 N−(3−ブロモ−4−メトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:209〜210.5℃
4 N−(5−クロロ−2−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:180〜181℃
5 N−(2,4−ジヒドロキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:194〜195℃
6 N−(2,3−ジヒドロキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:108〜109℃
7 N−(2,4,5−トリメトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:98.5〜99.5℃
8 N−(3−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:204.5〜206℃
9 N−(4,5−メチレンジオキシ−2−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:108〜111℃
10 N−(3,4,5−トリメトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:139〜141℃
11 N−(4−クロロ−3−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:184〜187℃
12 N−(4−メトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:175〜177℃
13 N−(2−ブロモベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:148.5〜150℃
14 N−(2,3,4−トリメトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:179〜181℃
15 N−(2−ヒドロキシ−4,6−ジメトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:133〜135℃
16 N−(2,5−ジメトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:137〜139℃
17 N−(2,3−ジメトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:91〜93℃
18 N−(2,5−ジフルオロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:186〜187.5℃
19 N−(5−ブロモ−2−ヒドロキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:217〜218℃
20 N−(4−ジメチルアミノベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:185.5〜187℃
21 N−(4−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:191〜193℃
22 N−(2−ヒドロキシ−3−メトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:173〜175℃
23 N−(3−クロロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:184〜186℃
24 N−(2−ヒドロキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:172〜174℃
25 N−(2,3,4−トリベンジルオキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:147〜149℃
26 N−(ベンジリデンアミノ)グアニジンアセテート、mp:196〜198℃
27 N−(3,4,5−トリメトキシベンジリデンアミノ)グアニジンアセテート、mp:223〜225℃
28 N−(4−クロロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:192〜194℃
29 N−(3,4−メチレンジオキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:204〜206℃
30 N−(4−ブロモベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:199〜200℃
31 N−(4−ジエチルアミノベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:100〜102℃
32 N−(2−ヒドロキシ−5−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:217〜219℃
33 N−(4−ヒドロキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:83〜85℃
34 N−(2,4,6−トリメトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:80〜82℃
35 N−(2,3,4−トリヒドロキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:100〜102℃
36 N−(3−ヒドロキシ−4−メトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:88〜89℃
37 N−(2−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:204〜206℃
38 N−(2−ブロモ−3,4,5−トリメトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:172〜175℃
39 N−(2,4−ジニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:208〜211℃
40 N−(2−クロロ−6−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:92〜94℃
41 N−(3,5−ジメトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:92〜95℃
42 N−(5−ヒドロキシ−2−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:182〜183℃
43 N−(3,6−ジメトキシ−2−ニトロキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:101〜102℃
44 N−(3,4−ジメトキシ−2−クロロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:95〜97℃
45 N−(3,4−ジメトキシ−2−クロロベンジリデンアミノ)グアニジンアセテート、mp:198〜200℃
46 N−(ベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:169〜171℃
47 N−(3,4−ジメトキシ−2−クロロベンジリデンアミノ)−N’−ヒドロキシグアニジン1.5塩酸塩、mp:214〜216℃
48 N−(2,3−ジメトキシ−5−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.3水和物、mp:174〜176℃
49 N−(2,3−ジメトキシ−5−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.3水和物、mp:174〜176℃
50 N−(2,3−ジメトキシ−5,6−ジニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.15水和物、mp:178〜179℃
51 N−(2,6−ジメトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:69〜71℃
52 N−(2,3−ジメトキシ−6−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:81〜83℃
53 N−(5−ブロモ−2,4−ジメトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:102〜105℃
54 N−(2−フルオロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.1水和物、mp:169〜171℃
55 N−(2−メトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:79〜82℃
56 N−(2,4,6−トリメトキシベンジリデンアミノ)グアニジンアセテート、mp:66〜68℃
57 N−(2,3−メチレンジオキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:163〜164.5℃
58 N−(4−ブロモ−3−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:201〜202.5℃
59 N−(5−ブロモ−2−ヒドロキシ−3−メトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:131.5〜134℃
60 N−(3−メトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:151〜153.5℃
61 N−(2,3−ジニトロ−6−クロロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:170〜172.5℃
62 N−(3,6−ジクロロ−2−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:183〜184.5℃
63 N−(2,6−ジニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:91〜93℃
64 N−(2−クロロ−3,4−ジメトキシ−6−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:104〜106.5℃
65 N−(2,4−ジニトロベンジリデンアミノ)グアニジンアセテート、mp:224〜226℃
66 N−(2−クロロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:156〜158℃
67 N−(4−フルオロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.25水和物、mp:182〜184℃
68 N−(3−フルオロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.2水和物、mp:170〜171.5℃
69 N−(4−シアノベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.2水和物、mp:203〜204℃
70 N−(3,5−ジメトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.5水和物、mp:131〜133℃
71 N−(4−フルオロ−3−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:190〜192.5℃
72 N−(2−クロロ−5−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.2水和物、mp:189〜191℃
73 N−(4−クロロ−2−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.25水和物、mp:179〜181.5℃
74 N−(3,4−ジクロロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:200〜202.5℃
75 N−(2,4−ジクロロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.5水和物、mp:158〜161℃
76 N−(4−メトキシ−3−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジン、mp:219〜221℃
77 N−(2,3−ジクロロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:197〜199.5℃
78 N−(2−フルオロ−5−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.4水和物、mp:172〜175℃
79 N−(2−メトキシ−5−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.7水和物、mp:115〜117℃
80 N−(4−ヒドロキシ−3,5−ジメトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.4水和物、mp:114〜115℃
81 N−(2−ブロモ−5−クロロ3−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:195〜196.5℃
82 N−(3−ブロモ−2,6−ジニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.5水和物1.8プロパノール、mp:91〜93℃
83 N−(3,5−ジニトロ−2−メトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.2水和物、mp:185〜187℃
84 N−(5−ブロモ−2−ヒドロキシ−3−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.1水和物、mp:186〜189℃
85 N−(3−ニトロベンジリデンアミノ)グアニジンアセテート、mp:147〜148.5℃
86 N−(2−ヒドロキシ−4,6−ジメトキシベンジリデンアミノ)グアニジンアセテート、mp:115〜118℃
87 N−(4−ニトロベンジリデンアミノ)グアニジンアセテート、mp:184〜186℃
88 N−(3−メトキシ−2,6−ジニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:123.5〜125℃
89 N−(3−ブロモ−4−フルオロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:204.5〜206.5℃
90 N−(2,3−ジフルオロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:186.5〜187℃
91 N−(4−クロロ−3−フルオロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.5水和物、mp:166.5〜167.5℃
92 N−(4−ブロモ−3−フルオロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.6水和物、mp:183〜185.5℃
93 N−(3−ブロモ−4−フルオロベンジリデンアミノ)グアニジンアセテート、mp:172〜173.5℃
94 N−(2,3−ジフルオロベンジリデンアミノ)グアニジンアセテート、mp:149〜151.5℃
95 N−(4−クロロ−3−フルオロベンジリデンアミノ)グアニジンアセテート、mp:165〜171℃
96 N−(3−メトキシ−2,6−ジニトロベンジリデンアミノ)グアニジン塩酸塩、mp:217〜218℃
97 N−(3−ブロモ−2,6−ジニトロベンジリデンアミノ)グアニジン塩酸塩、mp:166.5〜168℃
98 N−(2,3−ジメトキシ−5,6−ジニトロベンジリデンアミノ)グアニジンアセテート、mp:165〜171℃
99 N−(5−ブロモ−2,4−ジメトキシベンジリデンアミノ)グアニジンアセテート0.5水和物、mp:221〜224℃
100 N−(2,3−ジメトキシ−5−ニトロベンジリデンアミノ)グアニジンアセテート、mp:191〜194℃
101 N−(3,4−ジフルオロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:199〜201℃
102 N−(4−フェニルベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:171〜173℃
103 N−(3−クロロ−2,6−ジニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:85〜88℃
104 N−(4−フェニルベンジリデンアミノ)グアニジンアセテート、mp:191〜194℃
105 N−(3,4−ジフルオロベンジリデンアミノ)グアニジンアセテート、mp:176〜178℃
106 N−(4−ブロモ−2−フルオロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.3水和物、mp:176〜179℃
107 N−(2−フルオロ−5−ニトロベンジリデンアミノ)グアニジンアセテート、mp:192〜195℃
108 N−(4−ブロモ−2−フルオロベンジリデンアミノ)グアニジンアセテート、mp:187〜188℃
109 N−(2−ブロモ−5−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:148〜150℃
110 N−(2,4−ジニトロベンジリデンアミノ)−N’−ヒドロキシグアニジン塩酸塩、mp:191〜193℃
111 N−(2,6−ジフルオロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:176〜179℃
112 N−(3−クロロ−4−フルオロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:198.5〜201℃
113 N−(3,5−ジクロロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:208〜210.5℃
114 N−(2−ブロモ−4−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:170〜173℃
115 N−(3,5−ジニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート0.5水和物、mp:202〜207℃
116 N−(2,3−ジニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:214〜216℃
117 N−(3,5−ジクロロベンジリデンアミノ)グアニジンアセテート、mp:131〜134℃
118 N−(3,5−ジニトロベンジリデンアミノ)グアニジンアセテート二水和物、mp:251〜254℃(分解)
119 N−(2,6−ジフルオロベンジリデンアミノ)グアニジンアセテート、mp:138.5〜141℃
120 N−(3−クロロ−4−フルオロベンジリデンアミノ)グアニジンアセテート、mp:141〜144℃
121 N−(2−ブロモ−4−ニトロベンジリデンアミノ(nitroobenzylideneamino))グアニジンアセテート、mp:145〜147℃
122 N−(2−ブロモ−5−ニトロベンジリデンアミノ(nitroobenzylideneamino))グアニジンアセテート、mp:205〜208℃(分解)
123 N−(2−ヨードベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:136〜139℃
124 N−(2−ヨードベンジリデンアミノ)グアニジンアセテート、mp:1714〜173℃
125 N−(2,3−ジメトキシ−5−ニトロベンジリデンアミノ)グアニジン塩酸塩、mp:237〜238℃
126 N−(2−ヒドロキシ−4−メトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:174〜176℃
127 N−(2−ヒドロキシ−4−メトキシベンジリデンアミノ)グアニジンアセテート、mp:161〜164℃
128 N−(4−ブロモ−3−ニトロベンジリデンアミノ)グアニジンアセテート、mp:152〜153℃
129 N−(6−クロロ−2,3−ジニトロベンジリデンアミノ)グアニジン塩酸塩、mp:153〜154.5℃
130 N−(3−ブロモ−4−メトキシベンジリデンアミノ)グアニジン塩酸塩、mp:261〜262.5℃
131 N−(3−ヨードベンジリデンアミノ)グアニジン塩酸塩、mp:203〜204℃
132 N−(3−ヨードベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:193.5〜195℃
133 N−(2−スルホベンジリデンアミノ)グアニジン塩酸塩、mp:>260℃
134 N−(2−スルホベンジリデンアミノ)−N’−ヒドロキシグアニジン、mp:243.5〜244℃
135 N−(3,4−ジクロロベンジリデンアミノ)グアニジンアセテート、mp:138〜140℃
136 N−(2−クロロ−5−ニトロベンジリデンアミノ)グアニジンアセテート、mp:222〜224℃(分解)
137 N−(4−クロロ−3−ニトロベンジリデンアミノ)グアニジンアセテート、mp:136〜139℃(分解)
138 N−(4−フルオロ−3−ニトロベンジリデンアミノ)グアニジンアセテート、mp:222〜224℃(分解)
139 N−(4−メトキシ−3−ニトロベンジリデンアミノ)グアニジンアセテート、mp:144〜147℃
140 N−(2−クロロ−3,4,5−トリメトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:176〜178℃
141 N−(3,5−ジフルオロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:210.5〜213℃
142 N−(5−ブロモ−2,3,4−トリメトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:195〜197℃
143 N−(3−クロロ−4−メトキシベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:204〜207℃
144 N−(2,3−ジメトキシ−5−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジン塩酸塩、mp:196〜197.5℃
145 N−(3,5−ジフルオロ−2−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:176〜178℃
146 N−(3,5−ジクロロ−2−ニトロベンジリデンアミノ)−N’−ヒドロキシグアニジントシレート、mp:205〜207℃
147 N−(3,5−ジフルオロ−2−ニトロベンジリデンアミノ)グアニジンアセテート、mp:231〜233℃
148 N−(3,5−ジクロロ−2−ニトロベンジリデンアミノ)グアニジンアセテート、mp:88〜91℃
149 N−(2−ヒドロキシ−3−メトキシ−5−ニトロベンジリデンアミノ)グアニジン塩酸塩、mp:243〜246℃
150 N−(2−ヒドロキシ−4−メトキシ−5−ニトロベンジリデンアミノ)グアニジンヘミアセテート、mp:227〜230℃
151 N−(3−クロロ−4−メトキシ−5−ニトロベンジリデンアミノ)グアニジンアセテート、mp:255〜258℃(分解)
152 N−(3,5−ジクロロ4−メトキシベンジリデンアミノ)グアニジンアセテート、mp:185〜190℃
153 N−(3−ブロモ−4−メトキシ−5−メチルベンジリデンアミノ)グアニジンアセテート、mp:163〜166℃
154 N−(2,3,4−トリメトキシベンジリデンアミノ)グアニジン塩酸塩、mp:181〜183℃
155 N−(4−クロロ−2−メトキシ−5−ニトロベンジリデンアミノ)グアニジンアセテート、mp:196〜199℃
156 N−(3,6−ジクロロ−2−ニトロベンジリデンアミノ)グアニジンアセテート、mp:219.5〜221℃
157 N−(2−ヒドロキシ−4−メチル−5−ニトロベンジリデンアミノ)グアニジン塩酸塩、mp:229〜230℃
158 N−(2−ブロモ−5−クロロ−3−ニトロベンジリデンアミノ)グアニジンアセテート、mp:136.5〜137℃
159 N−(3−ヒドロキシ−4−メチル−2−ニトロベンジリデンアミノ)グアニジンアセテート、mp:240〜241℃
160 N−(5−ブロモ−4−メチル−2−ニトロベンジリデンアミノ)グアニジン塩酸塩、mp:246.5〜248℃
161 N−(5−ブロモ−2−ヒドロキシ−3−ニトロベンジリデンアミノ)グアニジン塩酸塩、mp:>250℃
162 N−(5−ブロモ−2−メトキシ−3−ニトロベンジリデンアミノ)グアニジン塩酸塩、mp:258〜259℃
163 N−(2,4−ジメトキシ−5−ニトロベンジリデンアミノ)グアニジンアセテート、mp:207〜210℃
164 N−(4−ブロモ−2−フルオロ−5−ニトロベンジリデンアミノ)グアニジンアセテート、mp:175〜198℃(分解)
本実施例は、式(I)で表される化合物および治療上活性なそれらの酸付加塩の、精神障害の治療における力価を示すものである。
I125−NDP−αMSHをリガンドとして用い、基本的にはLunecらのMelanoma Res 1992; 2; 5-12に記載されている通りに結合アッセイを行った。
I125−NDP−αMSHをリガンドとして用い、基本的にはSzardeningsらのJ Biol Chem 1997; 272; 27943-27948およびSchioethらのFEBS Lett 1997; 410; 223-228に記載されている通りに結合アッセイを行った。
基本的にはSchioethらのBr J Pharmacol 1998; 124; 75-82に記載されている通りにcAMPの刺激を行った。
以下に挙げる剤型は、本発明に係る薬理学的に活性なあらゆる化合物に適用できる剤型を例示するものである。
Claims (8)
- 前記関節炎が、慢性関節リウマチ、乾癬性関節炎、または反応性関節炎である請求項1に記載の組成物。
- R1、R2、R3、R4、およびR5の1以上がメチルである請求項1または2に記載の組成物。
- 上記ハロゲンがフルオロまたはクロロである請求項1に記載の組成物。
- 一般式(I)で表わされる前記化合物が、以下から選択される化合物である請求項1〜4のいずれかに記載の組成物。
N−(2−クロロ−3,4−ジメトキシベンジリデンアミノ)グアニジンアセテート、
N−(5−ブロモ−2,4−ジメトキシベンジリデンアミノ)グアニジンアセテート0.5水和物、
N−(3−クロロ−4−メトキシ−5−ニトロベンジリデンアミノ)グアニジン、
N−(3,5−ジクロロ−4−メトキシベンジリデンアミノ)グアニジンアセテート、
N−(3−ブロモ−4−メトキシ−5−メチルベンジリデンアミノ)グアニジンアセテート、
N−(4−クロロ−2−メトキシ−5−ニトロベンジリデンアミノ)グアニジンアセテート、および
N−(5−ブロモ−2−メトキシ−3−ニトロベンジリデンアミノ)グアニジン塩酸塩。 - 一般式(I)で表わされる前記化合物が、N−(2−クロロ−3,4−ジメトキシベンジリデンアミノ)グアニジンアセテートである請求項1に記載の組成物。
- 慢性関節リウマチの治療のための請求項6に記載の組成物。
- 1以上の佐剤(adjuvant)、担体、および/または賦形剤をさらに含む請求項1〜7のいずれかに記載の組成物。
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WO2002011715A3 (en) | 2003-01-16 |
JP5654190B2 (ja) | 2015-01-14 |
GB0019357D0 (en) | 2000-09-27 |
KR20030022371A (ko) | 2003-03-15 |
IL154272A (en) | 2010-12-30 |
MXPA03001072A (es) | 2004-03-10 |
US9227927B2 (en) | 2016-01-05 |
US20120178820A1 (en) | 2012-07-12 |
AU2001276522A1 (en) | 2002-02-18 |
US20040024060A1 (en) | 2004-02-05 |
BR0113053A (pt) | 2003-07-08 |
US8410174B2 (en) | 2013-04-02 |
US8148429B2 (en) | 2012-04-03 |
US20070231267A1 (en) | 2007-10-04 |
CA2417098A1 (en) | 2002-02-14 |
US20070088085A1 (en) | 2007-04-19 |
WO2002011715A2 (en) | 2002-02-14 |
KR100929363B1 (ko) | 2009-12-02 |
EP1313461A2 (en) | 2003-05-28 |
IL154272A0 (en) | 2003-09-17 |
JP2004505912A (ja) | 2004-02-26 |
ZA200300829B (en) | 2004-02-25 |
US8309609B2 (en) | 2012-11-13 |
JP2011246471A (ja) | 2011-12-08 |
US20130295009A1 (en) | 2013-11-07 |
US20110015437A1 (en) | 2011-01-20 |
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