JP2005504039A5 - - Google Patents
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- Publication number
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 45
- 239000003814 drug Substances 0.000 claims 20
- 229940124597 therapeutic agent Drugs 0.000 claims 14
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 229940079593 drug Drugs 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- -1 methylenedioxy Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 208000022531 anorexia Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 206010061428 decreased appetite Diseases 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
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 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
- 208000028867 ischemia Diseases 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 238000000034 method Methods 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
- 208000017520 skin disease Diseases 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
- PTNJNTACFJEMIC-UHFFFAOYSA-N 2-[[1-(2-butoxyphenyl)-5-(propylamino)pyrrol-2-yl]methylideneamino]guanidine Chemical compound CCCCOC1=CC=CC=C1N1C(C=NNC(N)=N)=CC=C1NCCC PTNJNTACFJEMIC-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
- GCYSAAKDBFDTPO-UHFFFAOYSA-N 2-[[1-(4-aminophenyl)-5-hydroxypyrrol-2-yl]methylideneamino]guanidine Chemical compound NC(=N)NN=CC1=CC=C(O)N1C1=CC=C(N)C=C1 GCYSAAKDBFDTPO-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
- 206010006895 Cachexia Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 201000001880 Sexual dysfunction Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 210000000748 cardiovascular system Anatomy 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 238000003745 diagnosis Methods 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 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
- 230000003054 hormonal effect Effects 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 210000004324 lymphatic system Anatomy 0.000 claims 1
- 230000007257 malfunction Effects 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 210000000578 peripheral nerve Anatomy 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 230000002285 radioactive effect Effects 0.000 claims 1
- 230000010410 reperfusion Effects 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 effect 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
- 230000008733 trauma Effects 0.000 claims 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009143997A Division 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005504039A JP2005504039A (ja) | 2005-02-10 |
| JP2005504039A5 true JP2005504039A5 (enExample) | 2006-01-12 |
| JP4450620B2 JP4450620B2 (ja) | 2010-04-14 |
Family
ID=9919909
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003518518A Expired - Fee Related JP4450620B2 (ja) | 2001-08-06 | 2002-08-06 | 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 |
| 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 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US7186748B2 (enExample) |
| EP (1) | EP1414440B1 (enExample) |
| JP (2) | JP4450620B2 (enExample) |
| KR (1) | KR20040019302A (enExample) |
| AU (1) | AU2002313542B2 (enExample) |
| BR (1) | BR0210445A (enExample) |
| CA (1) | CA2448356C (enExample) |
| CY (1) | CY1106424T1 (enExample) |
| DE (1) | DE60217503T2 (enExample) |
| DK (1) | DK1414440T3 (enExample) |
| ES (1) | ES2280555T3 (enExample) |
| GB (1) | GB0119172D0 (enExample) |
| IL (1) | IL160181A0 (enExample) |
| MX (1) | MXPA04001037A (enExample) |
| NO (1) | NO20040465L (enExample) |
| NZ (1) | NZ529666A (enExample) |
| PT (1) | PT1414440E (enExample) |
| SI (1) | SI1414440T1 (enExample) |
| WO (1) | WO2003013509A1 (enExample) |
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| WO2009074157A1 (en) * | 2007-12-13 | 2009-06-18 | Action Pharma A/S | Fully-modified phenyl pyrrole aminoguanidines |
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| ES2624828T3 (es) | 2008-07-16 | 2017-07-17 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros |
| JP2012500219A (ja) | 2008-08-15 | 2012-01-05 | エヌサーティー・ファーマシューティカルズ，エルエルシー | 治療薬剤としての、ｓ−ニトロソグルタチオンレダクターゼの新規ピロール阻害剤 |
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| EP2362731B1 (en) | 2008-10-31 | 2016-04-06 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| WO2010056717A1 (en) | 2008-11-17 | 2010-05-20 | Merck Sharp & Dohme Corp. | Substituted bicyclic amines for the treatment of diabetes |
| WO2011011508A1 (en) | 2009-07-23 | 2011-01-27 | Schering Corporation | Benzo-fused oxazepine compounds as stearoyl-coenzyme a delta-9 desaturase inhibitors |
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| JP5990101B2 (ja) | 2009-09-16 | 2016-09-07 | オートニアム マネジメント アクチエンゲゼルシャフトＡｕｔｏｎｅｕｍ Ｍａｎａｇｅｍｅｎｔ ＡＧ | 自動車パネル用成型製品 |
| JP2013520502A (ja) | 2010-02-25 | 2013-06-06 | メルク・シャープ・エンド・ドーム・コーポレイション | 有用な抗糖尿病薬である新規な環状ベンズイミダゾール誘導体 |
| US8785634B2 (en) | 2010-04-26 | 2014-07-22 | Merck Sharp & Dohme Corp | Spiropiperidine prolylcarboxypeptidase inhibitors |
| US9365539B2 (en) | 2010-05-11 | 2016-06-14 | Merck Sharp & Dohme Corp. | Prolylcarboxypeptidase inhibitors |
| WO2011156246A1 (en) | 2010-06-11 | 2011-12-15 | Merck Sharp & Dohme Corp. | Novel prolylcarboxypeptidase inhibitors |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| SG192941A1 (en) | 2011-02-25 | 2013-09-30 | Merck Sharp & Dohme | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agents |
| EP2502788B1 (en) | 2011-03-23 | 2014-03-12 | Autoneum Management AG | Production process for a moulded multilayer lining |
| EP2503040A1 (en) | 2011-03-23 | 2012-09-26 | Autoneum Management AG | Moulded multilayer lining |
| EP2602248A1 (en) | 2011-12-05 | 2013-06-12 | University Of Leicester | Novel pyrrole compounds |
| WO2014022528A1 (en) | 2012-08-02 | 2014-02-06 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| US8434136B1 (en) | 2012-11-29 | 2013-04-30 | Jeffry David Aronson | Full spectrum cyber identification determination process |
| US9319414B2 (en) | 2012-11-29 | 2016-04-19 | Jeffry David Aronson | Scalable full spectrum cyber determination process |
| JP2016516004A (ja) | 2013-02-22 | 2016-06-02 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | 抗糖尿病二環式化合物 |
| EP2970119B1 (en) | 2013-03-14 | 2021-11-03 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
| US9486494B2 (en) | 2013-03-15 | 2016-11-08 | Synergy Pharmaceuticals, Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| CA2905438A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| CA2909938A1 (en) * | 2013-04-22 | 2014-10-30 | Abbvie Inc. | Thiazoles and uses thereof |
| JP6606491B2 (ja) | 2013-06-05 | 2019-11-13 | シナジー ファーマシューティカルズ インコーポレイテッド | グアニル酸シクラーゼｃの超高純度アゴニスト、その作成および使用方法 |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| WO2018106518A1 (en) | 2016-12-06 | 2018-06-14 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
| WO2018118670A1 (en) | 2016-12-20 | 2018-06-28 | Merck Sharp & Dohme Corp. | Antidiabetic spirochroman compounds |
| CA3134635A1 (en) | 2019-04-03 | 2020-10-08 | Aligos Therapeutics, Inc. | Pyrrole compounds |
| EP4119140B1 (en) | 2019-05-10 | 2025-06-25 | SynAct Pharma ApS | Phenyl pyrrole aminoguanidine derivatives in combination with methotrexate for use in the treatment of arthritic disease |
| WO2022268825A1 (en) | 2021-06-21 | 2022-12-29 | Synact Pharma Aps | Phenyl pyrrole aminoguanidine salts and formulations |
| CN113651673A (zh) * | 2021-07-01 | 2021-11-16 | 烟台泰和新材料股份有限公司 | 一种芳烃侧链甲基氯代物的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9604348D0 (sv) | 1996-11-26 | 1996-11-26 | Wapharm Ab | Användning av hydroxyguanidiner |
| US6127381A (en) * | 1998-04-28 | 2000-10-03 | Basu; Amaresh | Isoquinoline compound melanocortin receptor ligands and methods of using same |
| WO2001025192A1 (en) * | 1999-10-06 | 2001-04-12 | Melacure Therapeutics Ab | Guanidine derivatives and their use in the production of a medicament for blocking xanthine oxidase/dehydrogenase |
| GB0002059D0 (en) | 2000-01-28 | 2000-03-22 | Melacure Therapeutics Ab | Novel aromatic amines |
| GB0019357D0 (en) | 2000-08-07 | 2000-09-27 | Melacure Therapeutics Ab | Novel phenyl guanidines |
| GB0019359D0 (en) * | 2000-08-07 | 2000-09-27 | Melacure Therapeutics Ab | Novel guanidines |
| GB0108631D0 (en) * | 2001-04-05 | 2001-05-30 | Melacure Therapeutics Ab | Novel benzylideneamino guanidines and their uses as ligands to the melanocortin receptors |
| US6951881B2 (en) * | 2002-05-10 | 2005-10-04 | Wyeth | (1-substituted-indol-3-yl) alkylidenehydrazinecarboximidamide derivatives as 5-hydroxytryptamine-6 ligands |
-
2001
- 2001-08-06 GB GBGB0119172.5A patent/GB0119172D0/en not_active Ceased
-
2002
- 2002-08-06 NZ NZ529666A patent/NZ529666A/en not_active IP Right Cessation
- 2002-08-06 JP JP2003518518A patent/JP4450620B2/ja not_active Expired - Fee Related
- 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 BR BR0210445-8A patent/BR0210445A/pt not_active IP Right Cessation
- 2002-08-06 PT PT02753136T patent/PT1414440E/pt unknown
- 2002-08-06 WO PCT/GB2002/003620 patent/WO2003013509A1/en not_active Ceased
- 2002-08-06 US US10/484,444 patent/US7186748B2/en not_active Expired - Fee Related
- 2002-08-06 ES ES02753136T patent/ES2280555T3/es not_active Expired - Lifetime
- 2002-08-06 KR KR10-2003-7016099A patent/KR20040019302A/ko not_active Withdrawn
- 2002-08-06 DK DK02753136T patent/DK1414440T3/da active
- 2002-08-06 SI SI200230506T patent/SI1414440T1/sl unknown
- 2002-08-06 IL IL16018102A patent/IL160181A0/xx unknown
- 2002-08-06 MX MXPA04001037A patent/MXPA04001037A/es unknown
- 2002-08-06 CA CA2448356A patent/CA2448356C/en not_active Expired - Fee Related
- 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
-
2009
- 2009-06-17 JP JP2009143997A patent/JP2009242414A/ja not_active Withdrawn
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