JP2005504039A5 - - Google Patents
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- JP2005504039A5 JP2005504039A5 JP2003518518A JP2003518518A JP2005504039A5 JP 2005504039 A5 JP2005504039 A5 JP 2005504039A5 JP 2003518518 A JP2003518518 A JP 2003518518A JP 2003518518 A JP2003518518 A JP 2003518518A JP 2005504039 A5 JP2005504039 A5 JP 2005504039A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrol
- guanidine
- compound according
- propylideneamino
- 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
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- 150000001875 compounds Chemical class 0.000 claims 45
- 239000003814 drug Substances 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000004385 trihaloalkyl group Chemical group 0.000 claims 6
- 125000004432 carbon atoms Chemical group C* 0.000 claims 5
- 229940079593 drugs Drugs 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- -1 methylenedioxy Chemical group 0.000 claims 4
- 206010061428 Decreased appetite Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000011780 sodium chloride Substances 0.000 claims 3
- 206010061255 Ischaemia Diseases 0.000 claims 2
- 206010025650 Malignant melanoma Diseases 0.000 claims 2
- 210000003491 Skin Anatomy 0.000 claims 2
- 208000006641 Skin Disease Diseases 0.000 claims 2
- 206010040829 Skin discolouration Diseases 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 230000008929 regeneration Effects 0.000 claims 2
- 238000011069 regeneration method Methods 0.000 claims 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- JPCUXDJNKAPCAK-UHFFFAOYSA-N 1-[3-[1-[3-(butylamino)-4-methylphenyl]-4-methylpyrrol-2-yl]propylidene]guanidine Chemical compound C1=C(C)C(NCCCC)=CC(N2C(=CC(C)=C2)CCC=NC(N)=N)=C1 JPCUXDJNKAPCAK-UHFFFAOYSA-N 0.000 claims 1
- SZBYBKFFPPRNGM-UHFFFAOYSA-N 2-[(1-phenylpyrrol-2-yl)methylideneamino]guanidine Chemical compound NC(=N)NN=CC1=CC=CN1C1=CC=CC=C1 SZBYBKFFPPRNGM-UHFFFAOYSA-N 0.000 claims 1
- MXSSGIKKSQQVML-UHFFFAOYSA-N 2-[(1-phenylpyrrol-3-yl)methylideneamino]guanidine Chemical compound C1=C(C=NNC(=N)N)C=CN1C1=CC=CC=C1 MXSSGIKKSQQVML-UHFFFAOYSA-N 0.000 claims 1
- FTLVJMKQHHAPPQ-UHFFFAOYSA-N 2-[(4-butoxy-1-phenylpyrrol-3-yl)methylideneamino]guanidine Chemical compound C1=C(C=NNC(N)=N)C(OCCCC)=CN1C1=CC=CC=C1 FTLVJMKQHHAPPQ-UHFFFAOYSA-N 0.000 claims 1
- BVPJBFYWDFGEQD-UHFFFAOYSA-N 2-[(5-tert-butyl-1-phenylpyrrol-2-yl)methylideneamino]guanidine Chemical compound CC(C)(C)C1=CC=C(C=NNC(N)=N)N1C1=CC=CC=C1 BVPJBFYWDFGEQD-UHFFFAOYSA-N 0.000 claims 1
- PNFQDVYJQBKEKG-UHFFFAOYSA-N 2-[2-[1-(4-pyrrol-1-ylphenyl)pyrrol-2-yl]ethylideneamino]guanidine Chemical compound NC(=N)NN=CCC1=CC=CN1C1=CC=C(N2C=CC=C2)C=C1 PNFQDVYJQBKEKG-UHFFFAOYSA-N 0.000 claims 1
- INAGMDJKDCMGBN-UHFFFAOYSA-N 2-[2-[4-tert-butyl-1-[4-methoxy-2-(propylamino)phenyl]pyrrol-3-yl]ethylideneamino]guanidine Chemical compound CCCNC1=CC(OC)=CC=C1N1C=C(C(C)(C)C)C(CC=NNC(N)=N)=C1 INAGMDJKDCMGBN-UHFFFAOYSA-N 0.000 claims 1
- VEAZGZRETIXYKD-UHFFFAOYSA-N 2-[3-(1-phenylpyrrol-2-yl)propylideneamino]guanidine Chemical compound NC(=N)NN=CCCC1=CC=CN1C1=CC=CC=C1 VEAZGZRETIXYKD-UHFFFAOYSA-N 0.000 claims 1
- ZPSSSNXLXNAUJN-UHFFFAOYSA-N 2-[3-(4-methoxy-1-phenylpyrrol-2-yl)propylideneamino]guanidine Chemical compound C1=C(OC)C=C(CCC=NNC(N)=N)N1C1=CC=CC=C1 ZPSSSNXLXNAUJN-UHFFFAOYSA-N 0.000 claims 1
- OATSWRMBGTVFEB-UHFFFAOYSA-N 2-[3-(4-methyl-1-phenylpyrrol-3-yl)propylideneamino]guanidine Chemical compound C1=C(CCC=NNC(N)=N)C(C)=CN1C1=CC=CC=C1 OATSWRMBGTVFEB-UHFFFAOYSA-N 0.000 claims 1
- WSUCPDFYFNIGET-UHFFFAOYSA-N 2-[3-(5-methoxy-1-phenylpyrrol-3-yl)propylideneamino]guanidine Chemical compound COC1=CC(CCC=NNC(N)=N)=CN1C1=CC=CC=C1 WSUCPDFYFNIGET-UHFFFAOYSA-N 0.000 claims 1
- VRLSOCNICDJRMA-UHFFFAOYSA-N 2-[3-[1-(2-bromo-3-chlorophenyl)pyrrol-3-yl]propylideneamino]guanidine Chemical compound C1=C(CCC=NNC(=N)N)C=CN1C1=CC=CC(Cl)=C1Br VRLSOCNICDJRMA-UHFFFAOYSA-N 0.000 claims 1
- MHSDJUAWOGTJAH-UHFFFAOYSA-N 2-[3-[1-(2-hydroxyphenyl)pyrrol-2-yl]propylideneamino]guanidine Chemical compound NC(=N)NN=CCCC1=CC=CN1C1=CC=CC=C1O MHSDJUAWOGTJAH-UHFFFAOYSA-N 0.000 claims 1
- JOSCROVGIFIWEN-UHFFFAOYSA-N 2-[3-[1-(2-nitro-4-phenylphenyl)pyrrol-2-yl]propylideneamino]guanidine Chemical compound NC(=N)NN=CCCC1=CC=CN1C1=CC=C(C=2C=CC=CC=2)C=C1[N+]([O-])=O JOSCROVGIFIWEN-UHFFFAOYSA-N 0.000 claims 1
- VQQGUAUMDBAFJR-UHFFFAOYSA-N 2-[3-[1-(2-nitrophenyl)pyrrol-2-yl]propylideneamino]guanidine Chemical compound NC(=N)NN=CCCC1=CC=CN1C1=CC=CC=C1[N+]([O-])=O VQQGUAUMDBAFJR-UHFFFAOYSA-N 0.000 claims 1
- JHIYVRCHJLREML-UHFFFAOYSA-N 2-[3-[1-(2-tert-butylphenyl)-4-chloro-5-methylpyrrol-2-yl]propylideneamino]guanidine Chemical compound CC1=C(Cl)C=C(CCC=NNC(N)=N)N1C1=CC=CC=C1C(C)(C)C JHIYVRCHJLREML-UHFFFAOYSA-N 0.000 claims 1
- NTPYMXGRGQYCJI-UHFFFAOYSA-N 2-[3-[1-(3-fluorophenyl)-5-methylpyrrol-3-yl]propylideneamino]guanidine Chemical compound CC1=CC(CCC=NNC(N)=N)=CN1C1=CC=CC(F)=C1 NTPYMXGRGQYCJI-UHFFFAOYSA-N 0.000 claims 1
- DDUZLIMNWCMSDO-UHFFFAOYSA-N 2-[3-[1-(3-methylphenyl)-5-propoxypyrrol-2-yl]propylideneamino]guanidine Chemical compound CCCOC1=CC=C(CCC=NNC(N)=N)N1C1=CC=CC(C)=C1 DDUZLIMNWCMSDO-UHFFFAOYSA-N 0.000 claims 1
- SKVSXQOINGZNIB-UHFFFAOYSA-N 2-[3-[1-(3-tert-butylphenyl)-5-(2-methylpropanoyl)pyrrol-2-yl]propylideneamino]guanidine Chemical compound CC(C)C(=O)C1=CC=C(CCC=NNC(N)=N)N1C1=CC=CC(C(C)(C)C)=C1 SKVSXQOINGZNIB-UHFFFAOYSA-N 0.000 claims 1
- RPMJBFFBFZYOLJ-UHFFFAOYSA-N 2-[3-[1-(4-bromophenyl)-4-tert-butylpyrrol-3-yl]propylideneamino]guanidine Chemical compound C1=C(CCC=NNC(N)=N)C(C(C)(C)C)=CN1C1=CC=C(Br)C=C1 RPMJBFFBFZYOLJ-UHFFFAOYSA-N 0.000 claims 1
- XKEKCURPQOKKLI-UHFFFAOYSA-N 2-[3-[1-(4-chlorophenyl)-5-(2-phenylethyl)pyrrol-3-yl]propylideneamino]guanidine Chemical compound C=1C=C(Cl)C=CC=1N1C=C(CCC=NNC(=N)N)C=C1CCC1=CC=CC=C1 XKEKCURPQOKKLI-UHFFFAOYSA-N 0.000 claims 1
- QZNMIMTUJKJWFT-UHFFFAOYSA-N 2-[3-[1-[2-(2-methylpropanoyl)phenyl]-5-nitropyrrol-2-yl]propylideneamino]guanidine Chemical compound CC(C)C(=O)C1=CC=CC=C1N1C([N+]([O-])=O)=CC=C1CCC=NNC(N)=N QZNMIMTUJKJWFT-UHFFFAOYSA-N 0.000 claims 1
- RIGFKRQEUSRNCB-UHFFFAOYSA-N 2-[3-[1-[4-(propylamino)phenyl]-5-(trichloromethyl)pyrrol-3-yl]propylideneamino]guanidine Chemical compound C1=CC(NCCC)=CC=C1N1C(C(Cl)(Cl)Cl)=CC(CCC=NNC(N)=N)=C1 RIGFKRQEUSRNCB-UHFFFAOYSA-N 0.000 claims 1
- WSOPGEABKBOEBI-UHFFFAOYSA-N 2-[3-[1-[4-(trifluoromethyl)phenyl]pyrrol-2-yl]propylideneamino]guanidine Chemical compound NC(=N)NN=CCCC1=CC=CN1C1=CC=C(C(F)(F)F)C=C1 WSOPGEABKBOEBI-UHFFFAOYSA-N 0.000 claims 1
- FTFNFTFOQNOQKR-UHFFFAOYSA-N 2-[3-[4-hydroxy-1-[3-(trichloromethyl)phenyl]pyrrol-2-yl]propylideneamino]guanidine Chemical compound NC(=N)NN=CCCC1=CC(O)=CN1C1=CC=CC(C(Cl)(Cl)Cl)=C1 FTFNFTFOQNOQKR-UHFFFAOYSA-N 0.000 claims 1
- OJZDXDOJCOVPSX-UHFFFAOYSA-N 2-[3-[5-bromo-1-(4-bromophenyl)pyrrol-3-yl]propylideneamino]guanidine Chemical compound C1=C(CCC=NNC(=N)N)C=C(Br)N1C1=CC=C(Br)C=C1 OJZDXDOJCOVPSX-UHFFFAOYSA-N 0.000 claims 1
- BVMLYGPSBCWQEY-UHFFFAOYSA-N 2-[3-[5-tert-butyl-1-[2-tert-butyl-3,4-bis(trichloromethyl)phenyl]-4-(trichloromethyl)pyrrol-2-yl]propylideneamino]guanidine Chemical compound CC(C)(C)C1=C(C(Cl)(Cl)Cl)C=C(CCC=NNC(N)=N)N1C1=CC=C(C(Cl)(Cl)Cl)C(C(Cl)(Cl)Cl)=C1C(C)(C)C BVMLYGPSBCWQEY-UHFFFAOYSA-N 0.000 claims 1
- OGVIEMFMGREMAK-UHFFFAOYSA-N 2-[[1-(3,5-dichlorophenyl)pyrrol-2-yl]methylideneamino]guanidine Chemical compound NC(=N)NN=CC1=CC=CN1C1=CC(Cl)=CC(Cl)=C1 OGVIEMFMGREMAK-UHFFFAOYSA-N 0.000 claims 1
- GIJOIJFUUPGMHS-UHFFFAOYSA-N 2-[[1-(3-cyanophenyl)-5-(trifluoromethyl)pyrrol-2-yl]methylideneamino]guanidine Chemical compound NC(=N)NN=CC1=CC=C(C(F)(F)F)N1C1=CC=CC(C#N)=C1 GIJOIJFUUPGMHS-UHFFFAOYSA-N 0.000 claims 1
- NDXXQYJMEOTRML-UHFFFAOYSA-N 2-[[1-(3-cyanophenyl)pyrrol-2-yl]methylideneamino]guanidine Chemical compound NC(=N)NN=CC1=CC=CN1C1=CC=CC(C#N)=C1 NDXXQYJMEOTRML-UHFFFAOYSA-N 0.000 claims 1
- UOFHTGRABVMRGU-UHFFFAOYSA-N 2-[[1-(3-methoxyphenyl)pyrrol-2-yl]methylideneamino]guanidine Chemical compound COC1=CC=CC(N2C(=CC=C2)C=NNC(N)=N)=C1 UOFHTGRABVMRGU-UHFFFAOYSA-N 0.000 claims 1
- RYUKQNHMWPLSIM-UHFFFAOYSA-N 2-[[1-(4-chlorophenyl)pyrrol-2-yl]methylideneamino]guanidine Chemical compound NC(=N)NN=CC1=CC=CN1C1=CC=C(Cl)C=C1 RYUKQNHMWPLSIM-UHFFFAOYSA-N 0.000 claims 1
- FZOMZPQZBLDAPV-UHFFFAOYSA-N 2-[[1-(4-morpholin-4-ylphenyl)pyrrol-2-yl]methylideneamino]guanidine Chemical compound NC(=N)NN=CC1=CC=CN1C1=CC=C(N2CCOCC2)C=C1 FZOMZPQZBLDAPV-UHFFFAOYSA-N 0.000 claims 1
- NQBNBXXUCXBDST-UHFFFAOYSA-N 2-[[1-(4-pyrrolidin-1-ylphenyl)pyrrol-3-yl]methylideneamino]guanidine Chemical compound C1=C(C=NNC(=N)N)C=CN1C1=CC=C(N2CCCC2)C=C1 NQBNBXXUCXBDST-UHFFFAOYSA-N 0.000 claims 1
- LBKDGJAQSTYJRB-UHFFFAOYSA-N 2-[[1-(4-tert-butylphenyl)pyrrol-3-yl]methylideneamino]guanidine Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C=C(C=NNC(N)=N)C=C1 LBKDGJAQSTYJRB-UHFFFAOYSA-N 0.000 claims 1
- UUNCOFPVAGMZTB-UHFFFAOYSA-N 2-[[1-[3-(butylamino)phenyl]pyrrol-3-yl]methylideneamino]guanidine Chemical compound CCCCNC1=CC=CC(N2C=C(C=NNC(N)=N)C=C2)=C1 UUNCOFPVAGMZTB-UHFFFAOYSA-N 0.000 claims 1
- RIJVPRBEHOHFAZ-UHFFFAOYSA-N 2-[[1-[3-nitro-4-(propylamino)phenyl]pyrrol-3-yl]methylideneamino]guanidine Chemical compound C1=C([N+]([O-])=O)C(NCCC)=CC=C1N1C=C(C=NNC(N)=N)C=C1 RIJVPRBEHOHFAZ-UHFFFAOYSA-N 0.000 claims 1
- PPWVNMANELAPNI-UHFFFAOYSA-N 2-[[1-[4-(trifluoromethyl)phenyl]pyrrol-2-yl]methylideneamino]guanidine Chemical compound NC(=N)NN=CC1=CC=CN1C1=CC=C(C(F)(F)F)C=C1 PPWVNMANELAPNI-UHFFFAOYSA-N 0.000 claims 1
- MZTZASGDJFVFDC-UHFFFAOYSA-N 2-[[4-bromo-1-(2-butoxy-3-propoxyphenyl)pyrrol-2-yl]methylideneamino]guanidine Chemical compound CCCCOC1=C(OCCC)C=CC=C1N1C(C=NNC(N)=N)=CC(Br)=C1 MZTZASGDJFVFDC-UHFFFAOYSA-N 0.000 claims 1
- QZMGNACMDLSVQT-UHFFFAOYSA-N 2-[[4-chloro-1-(4-phenylphenyl)pyrrol-2-yl]methylideneamino]guanidine Chemical compound NC(=N)NN=CC1=CC(Cl)=CN1C1=CC=C(C=2C=CC=CC=2)C=C1 QZMGNACMDLSVQT-UHFFFAOYSA-N 0.000 claims 1
- VRLSMXYJKOFIQU-UHFFFAOYSA-N 2-[[4-cyano-1-(2-methylphenyl)pyrrol-3-yl]methylideneamino]guanidine Chemical compound CC1=CC=CC=C1N1C=C(C#N)C(C=NNC(N)=N)=C1 VRLSMXYJKOFIQU-UHFFFAOYSA-N 0.000 claims 1
- KPVUGXNNMRLPMI-UHFFFAOYSA-N 2-[[4-methyl-5-(propylamino)-1-[3-(trichloromethyl)phenyl]pyrrol-3-yl]methylideneamino]guanidine Chemical compound CCCNC1=C(C)C(C=NNC(N)=N)=CN1C1=CC=CC(C(Cl)(Cl)Cl)=C1 KPVUGXNNMRLPMI-UHFFFAOYSA-N 0.000 claims 1
- VSQMMKCSRIPRFT-UHFFFAOYSA-N 2-[[4-pentyl-1-[2-(trichloromethyl)phenyl]pyrrol-3-yl]methylideneamino]guanidine Chemical compound C1=C(C=NNC(N)=N)C(CCCCC)=CN1C1=CC=CC=C1C(Cl)(Cl)Cl VSQMMKCSRIPRFT-UHFFFAOYSA-N 0.000 claims 1
- WXJZHIAYBSYOPB-UHFFFAOYSA-N 2-[[5-(2-methylpropanoyl)-1-(2,3,4-trimethoxyphenyl)pyrrol-2-yl]methylideneamino]guanidine Chemical compound COC1=C(OC)C(OC)=CC=C1N1C(C(=O)C(C)C)=CC=C1C=NNC(N)=N WXJZHIAYBSYOPB-UHFFFAOYSA-N 0.000 claims 1
- QCAMYVMCLAUCEN-UHFFFAOYSA-N 2-[[5-chloro-1-[4-(2-methylpropanoyl)phenyl]-4-pentylpyrrol-2-yl]methylideneamino]guanidine Chemical compound ClC1=C(CCCCC)C=C(C=NNC(N)=N)N1C1=CC=C(C(=O)C(C)C)C=C1 QCAMYVMCLAUCEN-UHFFFAOYSA-N 0.000 claims 1
- KOSPSPGTPGQSLG-UHFFFAOYSA-N 2-[[5-hydroxy-1-(2-hydroxyphenyl)pyrrol-3-yl]methylideneamino]guanidine Chemical compound C1=C(C=NNC(=N)N)C=C(O)N1C1=CC=CC=C1O KOSPSPGTPGQSLG-UHFFFAOYSA-N 0.000 claims 1
- 210000004369 Blood Anatomy 0.000 claims 1
- PTNJNTACFJEMIC-UHFFFAOYSA-N CCCCOC1=CC=CC=C1N1C(C=NNC(N)=N)=CC=C1NCCC Chemical compound CCCCOC1=CC=CC=C1N1C(C=NNC(N)=N)=CC=C1NCCC PTNJNTACFJEMIC-UHFFFAOYSA-N 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 210000003169 Central Nervous System Anatomy 0.000 claims 1
- 206010012601 Diabetes mellitus Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010022114 Injury Diseases 0.000 claims 1
- 210000004324 Lymphatic System Anatomy 0.000 claims 1
- 206010027476 Metastasis Diseases 0.000 claims 1
- GCYSAAKDBFDTPO-UHFFFAOYSA-N NC(=N)NN=CC1=CC=C(O)N1C1=CC=C(N)C=C1 Chemical compound NC(=N)NN=CC1=CC=C(O)N1C1=CC=C(N)C=C1 GCYSAAKDBFDTPO-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 210000000578 Peripheral Nerves Anatomy 0.000 claims 1
- 206010037175 Psychiatric disease Diseases 0.000 claims 1
- 241000580858 Simian-Human immunodeficiency virus Species 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 230000000240 adjuvant Effects 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 230000000172 allergic Effects 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000000748 cardiovascular system Anatomy 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 238000003745 diagnosis Methods 0.000 claims 1
- 210000000750 endocrine system Anatomy 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 1
- 230000003054 hormonal Effects 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 1
- 229940113083 morpholine Drugs 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000002285 radioactive Effects 0.000 claims 1
- 201000001880 sexual dysfunction Diseases 0.000 claims 1
- 231100000872 sexual dysfunction Toxicity 0.000 claims 1
- 230000036299 sexual function Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 230000001225 therapeutic Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 231100000167 toxic agent Toxicity 0.000 claims 1
- 239000003440 toxic substance Substances 0.000 claims 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 1
Claims (46)
- 一般式（I）で表される化合物とその互変異性体、または薬理学的に活性なその塩。
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、炭素原子を１〜５個有するアルコキシ、ヒドロキシ、アルキルスルホニルオキシ、シアノ、ニトロ、トリハロアルキル、スルホ、および以下に示す構造のいずれかから選択され、
Ｒ6、Ｒ7、Ｒ8およびＲ9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、炭素原子を１〜５個有するアルコキシ、ヒドロキシ、炭素原子を０、１または２個有するアミン（第１級、第２級または第３級）、シアノ、ニトロ、トリハロアルキル、アミド、またはスルホから選択され、ここで示すｚは、フェニルまたはピロール環に対する残基の結合箇所を表す。 - 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。
- アルキルがメチル、エチル、ｎ-ブチル、ｎ-ペンチルまたはｔ-ブチルから選択される請求項１または２に記載の化合物。
- アルコキシがメトキシ、エトキシ、プロピルオキシ、ブトキシまたはｔ-ブトキシから選択される請求項１〜３のいずれかに記載の化合物。
- Ｒ6、Ｒ7およびＲ8が水素である請求項１〜４のいずれかに記載の化合物。
- 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１〜５のいずれかに記載の化合物。
- ｎ＝０である請求項１〜６のいずれかに記載の化合物。
- Ｒ5が水素である請求項１〜７のいずれかに記載の化合物。
- Ｒ3が水素である請求項１〜８のいずれかに記載の化合物。
- Ｒ4が水素である請求項１〜９のいずれかに記載の化合物。
- -Ｘ-ＣＨ＝Ｎ-ＮＨ-Ｃ(＝ＮＨ)-ＮＨ2部分がピロール環の２位にある請求項１〜１０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１〜１１のいずれかに記載の化合物。
- Ｒ2が水素である請求項１〜１２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１〜１３のいずれかに記載の化合物。
- Ｒ1がアルキル、アルコキシ、ハロゲン、水素、アミノまたはトリハロアルキルから選択される請求項１〜１４のいずれかに記載の化合物。
- Ｒ1がハロゲン、水素、トリハロアルキルまたはモルホリンから選択される請求項１５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１６に記載の化合物。
- ハロゲンが、クロロである請求項１６に記載の化合物。
- トリハロアルキルがトリフルオロメチルまたはトリクロロメチルから選択される請求項１６に記載の化合物。
- トリハロアルキルが、トリフルオロメチルである請求項１６に記載の化合物。
- 下記式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-Chlorophenyl)-1H-Pyrrol-2-yl]methyleneamino]guanidine
２ N-[1-(5-propylamino-1-(2-butoxyphenyl)-1H-pyrrol-2-yl)-methyleneamino]-guanidine
３ N-[3-[1-(2-Isobutyrylphenyl)-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-Trifluoromethylphenyl)-1H-pyrrol-2-yl]-propylideneamino]-guanidine
２５ N-(1-Phenyl-1H-pyrrol-3-ylmethylideneamino)-guanidine
２６ 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-trichloromethyl-phenyl)-1H-pyrrol-3-ylmethylideneamino]-guanidine
３６ N-[3-[1-(3-Nitro-biphenyl-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-ylphenyl)-1H-pyrrol-2-ylmethylideneamino]-guanidine
４６ N-[1-(4-Pyrrolidin-1-ylphenyl)-1H-pyrrol-3-ylmethylidenamino]-guanidine
４７ N-((1-Phenyl-1H-pyrrol-2-yl)methyleneamino)guanidine
４８ 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-dichlorophenyl)-1H-pyrrol-2-yl)methyleneamino]guanidine - 標識、放射性標識、または毒物（toxic agent）をさらに含む請求項１〜２１のいずれか１項に記載の化合物。
- 請求項１〜２２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１〜２２のいずれか１項に記載の化合物。
- 式（III）で表されるグアニジンまたはその塩もしくは保護形態（protected form）を、式（II）で表される化合物と反応させ、さらに必要または希望に応じて脱保護することを含む、請求項１に記載の化合物の製造方法。
- 請求項１〜２２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１〜２２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１〜２２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１〜２２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１〜２２のいずれか１項に記載の化合物を含む、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。
- 請求項１〜２２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１〜２２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１〜２２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１〜２２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１〜２２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１〜２２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１〜２２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、または心理状態に起因する食欲不振である、請求項３７に記載の治療薬。
- 請求項１〜２２のいずれか１項に記載の化合物を含む、末梢神経の再生を誘発する薬。
- 請求項１〜２２のいずれか１項に記載の化合物を含む、中枢神経の再生を誘発する薬。
- 請求項１〜２２のいずれか１項に記載の化合物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１〜２２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４２に記載の治療薬。
- 請求項１〜２２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および／または転移である、請求項４４に記載の薬。
- 請求項１〜２２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。
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| PCT/GB2002/003620 WO2003013509A1 (en) | 2001-08-06 | 2002-08-06 | N-phenylpyrrole guanidine derivatives as melanocortin reception ligands |
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-
2001
- 2001-08-06 GB GBGB0119172.5A patent/GB0119172D0/en not_active Ceased
-
2002
- 2002-08-06 PT PT02753136T patent/PT1414440E/pt unknown
- 2002-08-06 AU AU2002313542A patent/AU2002313542B2/en not_active Ceased
- 2002-08-06 DE DE60217503T patent/DE60217503T2/de not_active Expired - Lifetime
- 2002-08-06 EP EP02753136A patent/EP1414440B1/en not_active Expired - Lifetime
- 2002-08-06 DK DK02753136T patent/DK1414440T3/da active
- 2002-08-06 IL IL16018102A patent/IL160181A0/xx unknown
- 2002-08-06 NZ NZ529666A patent/NZ529666A/en not_active IP Right Cessation
- 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 WO PCT/GB2002/003620 patent/WO2003013509A1/en active IP Right Grant
- 2002-08-06 CA CA2448356A patent/CA2448356C/en not_active Expired - Fee Related
- 2002-08-06 ES ES02753136T patent/ES2280555T3/es not_active Expired - Lifetime
- 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 JP JP2003518518A patent/JP4450620B2/ja not_active Expired - Fee Related
- 2002-08-06 SI SI200230506T patent/SI1414440T1/sl unknown
-
2004
- 2004-02-02 NO NO20040465A patent/NO20040465L/no not_active Application Discontinuation
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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
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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
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