JP2011246471A - 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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- JP2011246471A JP2011246471A JP2011148414A JP2011148414A JP2011246471A JP 2011246471 A JP2011246471 A JP 2011246471A JP 2011148414 A JP2011148414 A JP 2011148414A JP 2011148414 A JP2011148414 A JP 2011148414A JP 2011246471 A JP2011246471 A JP 2011246471A
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- JP
- Japan
- Prior art keywords
- hydroxyguanidine tosylate
- nitrobenzylideneamino
- hydroxyguanidine
- tosylate
- guanidine
- 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
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- 102000004378 Melanocortin Receptors Human genes 0.000 title claims abstract description 13
- 108090000950 Melanocortin Receptors Proteins 0.000 title claims abstract description 13
- 239000003446 ligand Substances 0.000 title claims abstract description 9
- WNPXUCYRKHVMAD-UHFFFAOYSA-N 2-(benzylideneamino)guanidine Chemical compound NC(N)=NN=CC1=CC=CC=C1 WNPXUCYRKHVMAD-UHFFFAOYSA-N 0.000 title description 5
- WFBHRSAKANVBKH-UHFFFAOYSA-N N-hydroxyguanidine Chemical compound NC(=N)NO WFBHRSAKANVBKH-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 125
- 150000003839 salts Chemical class 0.000 claims abstract description 40
- 108010008364 Melanocortins Proteins 0.000 claims abstract description 26
- 239000002865 melanocortin Substances 0.000 claims abstract description 23
- -1 benzoyloxy, nitroxy, phenyl Chemical group 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims abstract description 4
- 150000001408 amides Chemical class 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 42
- 229940002612 prodrug Drugs 0.000 claims description 37
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- 230000008929 regeneration Effects 0.000 claims description 5
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- LSIMJMVTAJOCTC-UHFFFAOYSA-N 2-[(2,3-dimethoxy-5-nitrophenyl)methylideneamino]-1-hydroxyguanidine;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.COC1=CC([N+]([O-])=O)=CC(C=NN=C(N)NO)=C1OC LSIMJMVTAJOCTC-UHFFFAOYSA-N 0.000 claims description 4
- AFKIRIRPWKWGFW-UHFFFAOYSA-N 2-[(3,5-dimethoxyphenyl)methylideneamino]-1-hydroxyguanidine 4-methylbenzenesulfonic acid Chemical compound Cc1ccc(cc1)S(O)(=O)=O.COc1cc(OC)cc(C=NNC(=N)NO)c1 AFKIRIRPWKWGFW-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
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- DZNUWVWQUYFNRL-UHFFFAOYSA-N [n'-[(2-chloro-3,4-dimethoxyphenyl)methylideneamino]carbamimidoyl]azanium;acetate Chemical compound CC(O)=O.COC1=CC=C(C=NN=C(N)N)C(Cl)=C1OC DZNUWVWQUYFNRL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
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- GUTVHWJNYVXLGX-UHFFFAOYSA-N 1-hydroxy-2-[(2,3,4-trihydroxyphenyl)methylideneamino]guanidine 4-methylbenzenesulfonic acid Chemical compound Cc1ccc(cc1)S(O)(=O)=O.ONC(=N)NN=Cc1ccc(O)c(O)c1O GUTVHWJNYVXLGX-UHFFFAOYSA-N 0.000 claims description 2
- DIQNFHFNEDFOKS-UHFFFAOYSA-N 1-hydroxy-2-[(2,3,4-trimethoxyphenyl)methylideneamino]guanidine;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.COC1=CC=C(C=NN=C(N)NO)C(OC)=C1OC DIQNFHFNEDFOKS-UHFFFAOYSA-N 0.000 claims description 2
- XKCYXAAFDWLLLF-UHFFFAOYSA-N 1-hydroxy-2-[(2,4,6-trimethoxyphenyl)methylideneamino]guanidine;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.COC1=CC(OC)=C(C=NN=C(N)NO)C(OC)=C1 XKCYXAAFDWLLLF-UHFFFAOYSA-N 0.000 claims description 2
- RDUDGZXGDVGELN-UHFFFAOYSA-N 1-hydroxy-2-[(2-hydroxy-4,6-dimethoxyphenyl)methylideneamino]guanidine 4-methylbenzenesulfonic acid Chemical compound Cc1ccc(cc1)S(O)(=O)=O.COc1cc(O)c(C=NNC(=N)NO)c(OC)c1 RDUDGZXGDVGELN-UHFFFAOYSA-N 0.000 claims description 2
- DTFIKDFEHWKRPZ-UHFFFAOYSA-N 1-hydroxy-2-[(2-hydroxy-4-methoxyphenyl)methylideneamino]guanidine 4-methylbenzenesulfonic acid Chemical compound Cc1ccc(cc1)S(O)(=O)=O.COc1ccc(C=NNC(=N)NO)c(O)c1 DTFIKDFEHWKRPZ-UHFFFAOYSA-N 0.000 claims description 2
- FACDHGYCPLGGNO-UHFFFAOYSA-N 1-hydroxy-2-[(2-hydroxyphenyl)methylideneamino]guanidine 4-methylbenzenesulfonic acid Chemical compound Cc1ccc(cc1)S(O)(=O)=O.ONC(=N)NN=Cc1ccccc1O FACDHGYCPLGGNO-UHFFFAOYSA-N 0.000 claims description 2
- CEFIKQBKNTULRT-UHFFFAOYSA-N 1-hydroxy-2-[(2-methoxy-3,5-dinitrophenyl)methylideneamino]guanidine 4-methylbenzenesulfonic acid Chemical compound Cc1ccc(cc1)S(O)(=O)=O.COc1c(C=NNC(=N)NO)cc(cc1[N+]([O-])=O)[N+]([O-])=O CEFIKQBKNTULRT-UHFFFAOYSA-N 0.000 claims description 2
- OSTKRKSQQPGKFX-UHFFFAOYSA-N 1-hydroxy-2-[(2-methoxy-5-nitrophenyl)methylideneamino]guanidine 4-methylbenzenesulfonic acid Chemical compound Cc1ccc(cc1)S(O)(=O)=O.COc1ccc(cc1C=NNC(=N)NO)[N+]([O-])=O OSTKRKSQQPGKFX-UHFFFAOYSA-N 0.000 claims description 2
- QNNJJKUOBDWCNW-UHFFFAOYSA-N 1-hydroxy-2-[(2-methoxyphenyl)methylideneamino]guanidine;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.COC1=CC=CC=C1C=NN=C(N)NO QNNJJKUOBDWCNW-UHFFFAOYSA-N 0.000 claims description 2
- UHRQBZULAGKDHK-UHFFFAOYSA-N 1-hydroxy-2-[(2-nitrophenyl)methylideneamino]guanidine 4-methylbenzenesulfonic acid Chemical compound Cc1ccc(cc1)S(O)(=O)=O.ONC(=N)NN=Cc1ccccc1[N+]([O-])=O UHRQBZULAGKDHK-UHFFFAOYSA-N 0.000 claims description 2
- BXLZZGISWXMRLG-UHFFFAOYSA-N 1-hydroxy-2-[(3,4,5-trimethoxyphenyl)methylideneamino]guanidine;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.COC1=CC(C=NN=C(N)NO)=CC(OC)=C1OC BXLZZGISWXMRLG-UHFFFAOYSA-N 0.000 claims description 2
- YNXZNJZUTSAYBH-UHFFFAOYSA-N 1-hydroxy-2-[(3-hydroxy-4-methoxyphenyl)methylideneamino]guanidine;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.COC1=CC=C(C=NN=C(N)NO)C=C1O YNXZNJZUTSAYBH-UHFFFAOYSA-N 0.000 claims description 2
- RVJTYBOEFRSUAC-UHFFFAOYSA-N 1-hydroxy-2-[(3-iodophenyl)methylideneamino]guanidine;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.ONC(N)=NN=CC1=CC=CC(I)=C1 RVJTYBOEFRSUAC-UHFFFAOYSA-N 0.000 claims description 2
- QZOJTKKXLIRTOG-UHFFFAOYSA-N 1-hydroxy-2-[(3-methoxy-2,6-dinitrophenyl)methylideneamino]guanidine 4-methylbenzenesulfonic acid Chemical compound Cc1ccc(cc1)S(O)(=O)=O.COc1ccc(c(C=NNC(=N)NO)c1[N+]([O-])=O)[N+]([O-])=O QZOJTKKXLIRTOG-UHFFFAOYSA-N 0.000 claims description 2
- KHAPRIJYRVYVCR-UHFFFAOYSA-N 1-hydroxy-2-[(3-methoxyphenyl)methylideneamino]guanidine;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.COC1=CC=CC(C=NN=C(N)NO)=C1 KHAPRIJYRVYVCR-UHFFFAOYSA-N 0.000 claims description 2
- LKWMRKGNMFLYFZ-UHFFFAOYSA-N 1-hydroxy-2-[(3-nitrophenyl)methylideneamino]guanidine;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.ONC(N)=NN=CC1=CC=CC([N+]([O-])=O)=C1 LKWMRKGNMFLYFZ-UHFFFAOYSA-N 0.000 claims description 2
- YXWMARMWTYMMDR-UHFFFAOYSA-N 1-hydroxy-2-[(4-hydroxy-3,5-dimethoxyphenyl)methylideneamino]guanidine 4-methylbenzenesulfonic acid Chemical compound Cc1ccc(cc1)S(O)(=O)=O.COc1cc(C=NNC(=N)NO)cc(OC)c1O YXWMARMWTYMMDR-UHFFFAOYSA-N 0.000 claims description 2
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- TVSYDDBVTYUVCN-UHFFFAOYSA-N 1-hydroxy-2-[(4-methoxy-3-nitrophenyl)methylideneamino]guanidine Chemical compound COC1=CC=C(C=NNC(=N)NO)C=C1[N+]([O-])=O TVSYDDBVTYUVCN-UHFFFAOYSA-N 0.000 claims description 2
- DIVQBGCCELLABT-UHFFFAOYSA-N 1-hydroxy-2-[(4-methoxyphenyl)methylideneamino]guanidine;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.COC1=CC=C(C=NN=C(N)NO)C=C1 DIVQBGCCELLABT-UHFFFAOYSA-N 0.000 claims description 2
- LREYYIXAOMFMRV-UHFFFAOYSA-N 1-hydroxy-2-[(4-phenylphenyl)methylideneamino]guanidine 4-methylbenzenesulfonic acid Chemical compound Cc1ccc(cc1)S(O)(=O)=O.ONC(=N)NN=Cc1ccc(cc1)-c1ccccc1 LREYYIXAOMFMRV-UHFFFAOYSA-N 0.000 claims description 2
- LLTMOSKLLDBMPZ-UHFFFAOYSA-N 1-hydroxy-2-[(5-hydroxy-2-nitrophenyl)methylideneamino]guanidine 4-methylbenzenesulfonic acid Chemical compound Cc1ccc(cc1)S(O)(=O)=O.ONC(=N)NN=Cc1cc(O)ccc1[N+]([O-])=O LLTMOSKLLDBMPZ-UHFFFAOYSA-N 0.000 claims description 2
- OOSGGINZFUNZEL-UHFFFAOYSA-N 1-hydroxy-2-[[2,3,4-tris(phenylmethoxy)phenyl]methylideneamino]guanidine;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.C=1C=CC=CC=1COC1=C(OCC=2C=CC=CC=2)C(C=NN=C(NO)N)=CC=C1OCC1=CC=CC=C1 OOSGGINZFUNZEL-UHFFFAOYSA-N 0.000 claims description 2
- PJZAZUXDFXNADM-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethylideneamino)-1-hydroxyguanidine;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.ONC(N)=NN=CC1=CC=C2OCOC2=C1 PJZAZUXDFXNADM-UHFFFAOYSA-N 0.000 claims description 2
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Abstract
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 (45)
- XがHである請求項1に記載の使用。
- XがOHである請求項1に記載の使用。
- R1、R2、R3、R4、およびR5の1以上が、炭素原子を1〜5個有するアルキルである請求項1〜3のいずれか1項に記載の使用。
- R1、R2、R3、R4、およびR5の1以上がアルコキシである請求項1〜4のいずれか1項に記載の使用。
- 上記アルコキシがメトキシである請求項5に記載の使用。
- R1、R2、R3、R4、およびR5の1以上が、ハロゲン原子である請求項1〜6のいずれか1項に記載の使用。
- 上記ハロゲンがフルオロまたはクロロである請求項7に記載の使用。
- 以下の1〜164から選択される化合物または薬理学的に許容可能なその塩の、メラノコルチン受容体リガンドとしての使用および/またはメラノコルチン系に関連する障害の治療における使用。
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
26 N−(ベンジリデンアミノ)グアニジンアセテート
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
131 N−(3−ヨードベンジリデンアミノ)グアニジン塩酸塩
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
133 N−(2−スルホベンジリデンアミノ)グアニジン塩酸塩
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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 - 標識、好ましくは放射性標識、または毒物(toxic agent)がさらに存在する請求項1〜9のいずれか1項に記載の使用。
- メラノコルチン受容体リガンドとして、および/またはメラノコルチン系に関連する障害の治療に使用される請求項1〜9のいずれか1項に記載の化合物を生体内で形成するプロドラッグの使用。
- 医薬品組成物中において1以上の佐剤(adjuvant)、担体、または賦形剤と併用する、請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの使用。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの、炎症の治療薬の製造における使用。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの、精神障害の治療薬の製造における使用。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの、内分泌系またはホルモン系における機能不全の治療薬の製造における使用。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの、性機能および/または性機能不全の治療薬の製造における使用。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの、血液および/またはリンパ系における薬物性またはそれ以外の障害の治療薬の製造における使用。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの、アレルギー性疾患(disorder)の治療薬の製造における使用。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの、心血管系における障害の治療薬の製造における使用。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの、痛みの治療薬の製造における使用。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの、皮膚の日焼けまたは皮膚の淡色化を誘発する薬の製造における使用。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの、II型糖尿病の治療薬の製造における使用。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの、肥満の治療薬の製造における使用。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの、例えば、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のような食欲不振の治療薬の製造における使用。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの、末梢神経の再生を誘発する薬の製造における使用。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの、中枢神経の再生を誘発する薬の製造における使用。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの使用または投与を含む、炎症の治療方法。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの使用または投与を含む、精神障害の治療方法。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの使用または投与を含む、内分泌系またはホルモン系における機能不全の治療方法。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの使用または投与を含む、性機能および/または性機能不全の治療方法。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの使用または投与を含む、血液および/またはリンパ系における薬物性障害の治療方法。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの使用または投与を含む、心血管系における障害の治療方法。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの使用または投与を含む、痛みの治療方法。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの使用または投与を含む、皮膚の日焼けまたは皮膚の淡色化を誘発する方法。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの使用または投与を含む、II型糖尿病の治療方法。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの使用または投与を含む、肥満の治療方法。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの使用または投与を含む、例えば、癌、カヘキシー、高齢、HIV、外傷、および心理状態に起因する食欲不振のような食欲不振の治療方法。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの使用または投与を含む、末梢神経の再生の誘発方法。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの使用または投与を含む、中枢神経の再生の誘発方法。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの、黒色腫を含む皮膚障害の治療薬の製造における使用。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの、黒色腫および転移のような悪性疾患の治療および/または診断のための薬の製造における使用。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの使用または投与を含む、黒色腫を含む皮膚障害の治療方法。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの使用または投与を含む、黒色腫および転移のような悪性疾患の治療および/または診断方法。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの、虚血および/または虚血/再灌流の治療薬の製造における使用。
- 請求項1〜10のいずれか1項に記載の化合物または請求項11に記載のプロドラッグの使用または投与を含む、虚血および/または虚血/再灌流の治療方法。
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IL154272A (en) | 2010-12-30 |
WO2002011715A3 (en) | 2003-01-16 |
US9227927B2 (en) | 2016-01-05 |
EP1313461A2 (en) | 2003-05-28 |
WO2002011715A2 (en) | 2002-02-14 |
CA2417098A1 (en) | 2002-02-14 |
GB0019357D0 (en) | 2000-09-27 |
KR20030022371A (ko) | 2003-03-15 |
US8148429B2 (en) | 2012-04-03 |
JP5654190B2 (ja) | 2015-01-14 |
US20110015437A1 (en) | 2011-01-20 |
US8410174B2 (en) | 2013-04-02 |
US20070088085A1 (en) | 2007-04-19 |
JP5683396B2 (ja) | 2015-03-11 |
JP2004505912A (ja) | 2004-02-26 |
US20130295009A1 (en) | 2013-11-07 |
US20120178820A1 (en) | 2012-07-12 |
MXPA03001072A (es) | 2004-03-10 |
AU2001276522A1 (en) | 2002-02-18 |
US8309609B2 (en) | 2012-11-13 |
US20070231267A1 (en) | 2007-10-04 |
IL154272A0 (en) | 2003-09-17 |
KR100929363B1 (ko) | 2009-12-02 |
BR0113053A (pt) | 2003-07-08 |
US20040024060A1 (en) | 2004-02-05 |
ZA200300829B (en) | 2004-02-25 |
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