HRP20110780T2 - Aminoarilsulfonamidni spojevi i njihova upotreba kao ligandi 5-ht6 - Google Patents
Aminoarilsulfonamidni spojevi i njihova upotreba kao ligandi 5-ht6 Download PDFInfo
- Publication number
- HRP20110780T2 HRP20110780T2 HRP20110780TT HRP20110780T HRP20110780T2 HR P20110780 T2 HRP20110780 T2 HR P20110780T2 HR P20110780T T HRP20110780T T HR P20110780TT HR P20110780 T HRP20110780 T HR P20110780T HR P20110780 T2 HRP20110780 T2 HR P20110780T2
- Authority
- HR
- Croatia
- Prior art keywords
- sulfonyl
- diamine
- dimethylethane
- methylindole
- phenyl
- Prior art date
Links
- 239000003446 ligand Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 13
- 208000019901 Anxiety disease Diseases 0.000 claims abstract 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 7
- 108091005435 5-HT6 receptors Proteins 0.000 claims abstract 4
- 208000030814 Eating disease Diseases 0.000 claims abstract 4
- 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract 4
- 208000008589 Obesity Diseases 0.000 claims abstract 4
- 230000036506 anxiety Effects 0.000 claims abstract 4
- 208000035475 disorder Diseases 0.000 claims abstract 4
- 235000014632 disordered eating Nutrition 0.000 claims abstract 4
- 230000002496 gastric effect Effects 0.000 claims abstract 4
- 238000000034 method Methods 0.000 claims abstract 4
- 235000020824 obesity Nutrition 0.000 claims abstract 4
- 201000010099 disease Diseases 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 208000010877 cognitive disease Diseases 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims 5
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 208000023105 Huntington disease Diseases 0.000 claims 3
- 208000019430 Motor disease Diseases 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 208000018737 Parkinson disease Diseases 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 210000003169 central nervous system Anatomy 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 201000000980 schizophrenia Diseases 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- -1 N'-[5-(3-Chloro-5-methoxyindole-1-sulfonyl)-2-methoxyphenyl]-N,N-dimethylethene-1,2-diamine Chemical compound 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- XJGFIJSCZNRMOW-UHFFFAOYSA-N n',n'-dimethyl-n-[3-(3-methyl-5-propan-2-yloxyindol-1-yl)sulfonylphenyl]ethane-1,2-diamine Chemical compound C1=C(C)C2=CC(OC(C)C)=CC=C2N1S(=O)(=O)C1=CC=CC(NCCN(C)C)=C1 XJGFIJSCZNRMOW-UHFFFAOYSA-N 0.000 claims 1
- ZHOBEMVFEQYDGM-UHFFFAOYSA-N n',n'-dimethyl-n-[3-(5-propan-2-yloxyindol-1-yl)sulfonylphenyl]ethane-1,2-diamine Chemical compound C1=CC2=CC(OC(C)C)=CC=C2N1S(=O)(=O)C1=CC=CC(NCCN(C)C)=C1 ZHOBEMVFEQYDGM-UHFFFAOYSA-N 0.000 claims 1
- DBZMHOLYIAWQFD-UHFFFAOYSA-N n-(5-indol-1-ylsulfonyl-2-methoxyphenyl)-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(NCCN(C)C)C(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C=C1 DBZMHOLYIAWQFD-UHFFFAOYSA-N 0.000 claims 1
- IWLCODJSJOQLGS-UHFFFAOYSA-N n-[2-chloro-3-(5-methoxy-2-methylindol-1-yl)sulfonylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound CC1=CC2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=CC(NCCN(C)C)=C1Cl IWLCODJSJOQLGS-UHFFFAOYSA-N 0.000 claims 1
- MKDANQWEMADTMI-UHFFFAOYSA-N n-[2-ethyl-5-(5-fluoro-3-methylindol-1-yl)sulfonylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(NCCN(C)C)C(CC)=CC=C1S(=O)(=O)N1C2=CC=C(F)C=C2C(C)=C1 MKDANQWEMADTMI-UHFFFAOYSA-N 0.000 claims 1
- DYEGUFGNAVFXPX-UHFFFAOYSA-N n-[2-ethyl-5-(5-fluoroindol-1-yl)sulfonylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(NCCN(C)C)C(CC)=CC=C1S(=O)(=O)N1C2=CC=C(F)C=C2C=C1 DYEGUFGNAVFXPX-UHFFFAOYSA-N 0.000 claims 1
- VXOBZSRXSIEVKP-UHFFFAOYSA-N n-[2-ethyl-5-(5-methoxy-3-methylindol-1-yl)sulfonylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(NCCN(C)C)C(CC)=CC=C1S(=O)(=O)N1C2=CC=C(OC)C=C2C(C)=C1 VXOBZSRXSIEVKP-UHFFFAOYSA-N 0.000 claims 1
- RWNQBCHJAXOJKH-UHFFFAOYSA-N n-[2-ethyl-5-(5-methoxyindol-1-yl)sulfonylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(NCCN(C)C)C(CC)=CC=C1S(=O)(=O)N1C2=CC=C(OC)C=C2C=C1 RWNQBCHJAXOJKH-UHFFFAOYSA-N 0.000 claims 1
- IHGSQFJBSUAEDK-UHFFFAOYSA-N n-[2-methoxy-5-(3-methylindol-1-yl)sulfonylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(NCCN(C)C)C(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C)=C1 IHGSQFJBSUAEDK-UHFFFAOYSA-N 0.000 claims 1
- QSJIQLGAPGBNPU-UHFFFAOYSA-N n-[2-methoxy-5-(3-methylindol-1-yl)sulfonylphenyl]-n',n'-dimethylpropane-1,3-diamine Chemical compound C1=C(NCCCN(C)C)C(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(C)=C1 QSJIQLGAPGBNPU-UHFFFAOYSA-N 0.000 claims 1
- UENITHPPRRMZGV-UHFFFAOYSA-N n-[2-methoxy-5-(5-methoxy-3-methylindol-1-yl)sulfonylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(C)C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=C(OC)C(NCCN(C)C)=C1 UENITHPPRRMZGV-UHFFFAOYSA-N 0.000 claims 1
- CKVAWMINTOXJDF-UHFFFAOYSA-N n-[2-methoxy-5-(5-methoxy-3-methylindol-1-yl)sulfonylphenyl]-n',n'-dimethylpropane-1,3-diamine Chemical compound C1=C(C)C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=C(OC)C(NCCCN(C)C)=C1 CKVAWMINTOXJDF-UHFFFAOYSA-N 0.000 claims 1
- KARMRDJFDRSPLH-UHFFFAOYSA-N n-[3-(4-chloro-3-methylindol-1-yl)sulfonylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCNC1=CC=CC(S(=O)(=O)N2C3=CC=CC(Cl)=C3C(C)=C2)=C1 KARMRDJFDRSPLH-UHFFFAOYSA-N 0.000 claims 1
- RZVHOQHAYKZVRF-UHFFFAOYSA-N n-[3-(4-chloroindol-1-yl)sulfonylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCNC1=CC=CC(S(=O)(=O)N2C3=CC=CC(Cl)=C3C=C2)=C1 RZVHOQHAYKZVRF-UHFFFAOYSA-N 0.000 claims 1
- BVBPKPAZWFKSFO-UHFFFAOYSA-N n-[3-(5-bromoindol-1-yl)sulfonylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCNC1=CC=CC(S(=O)(=O)N2C3=CC=C(Br)C=C3C=C2)=C1 BVBPKPAZWFKSFO-UHFFFAOYSA-N 0.000 claims 1
- XGVXJAJVGJGLAF-UHFFFAOYSA-N n-[3-(5-chloro-3-methylindol-1-yl)sulfonyl-2-ethylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound CCC1=C(NCCN(C)C)C=CC=C1S(=O)(=O)N1C2=CC=C(Cl)C=C2C(C)=C1 XGVXJAJVGJGLAF-UHFFFAOYSA-N 0.000 claims 1
- IUMOLFCZLFZLHN-UHFFFAOYSA-N n-[3-(5-ethoxy-3-methylindol-1-yl)sulfonylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(C)C2=CC(OCC)=CC=C2N1S(=O)(=O)C1=CC=CC(NCCN(C)C)=C1 IUMOLFCZLFZLHN-UHFFFAOYSA-N 0.000 claims 1
- UWRFMKZNGJKXKU-UHFFFAOYSA-N n-[3-(5-ethyl-3-methylindol-1-yl)sulfonyl-4-methylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(C)C2=CC(CC)=CC=C2N1S(=O)(=O)C1=CC(NCCN(C)C)=CC=C1C UWRFMKZNGJKXKU-UHFFFAOYSA-N 0.000 claims 1
- SQJPIJJETHEZKE-UHFFFAOYSA-N n-[3-(5-fluoro-3-methylindol-1-yl)sulfonyl-5-methoxyphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound COC1=CC(NCCN(C)C)=CC(S(=O)(=O)N2C3=CC=C(F)C=C3C(C)=C2)=C1 SQJPIJJETHEZKE-UHFFFAOYSA-N 0.000 claims 1
- CGKZHTYQEJBORX-UHFFFAOYSA-N n-[3-(5-fluoro-3-methylindol-1-yl)sulfonyl-5-methylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCNC1=CC(C)=CC(S(=O)(=O)N2C3=CC=C(F)C=C3C(C)=C2)=C1 CGKZHTYQEJBORX-UHFFFAOYSA-N 0.000 claims 1
- ICZASJMSMDHWSL-UHFFFAOYSA-N n-[3-(5-methoxy-3-methylindol-1-yl)sulfonylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(C)C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=CC(NCCN(C)C)=C1 ICZASJMSMDHWSL-UHFFFAOYSA-N 0.000 claims 1
- PCLYKBMVORJSCA-UHFFFAOYSA-N n-[3-(5-methoxy-3-methylindol-1-yl)sulfonylphenyl]-n',n'-dimethylpropane-1,3-diamine Chemical compound C1=C(C)C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=CC(NCCCN(C)C)=C1 PCLYKBMVORJSCA-UHFFFAOYSA-N 0.000 claims 1
- YBRXXZMVJDEFFU-UHFFFAOYSA-N n-[3-(6-chloroindol-1-yl)sulfonylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCNC1=CC=CC(S(=O)(=O)N2C3=CC(Cl)=CC=C3C=C2)=C1 YBRXXZMVJDEFFU-UHFFFAOYSA-N 0.000 claims 1
- NKAMCCAGDLTBSH-UHFFFAOYSA-N n-[3-chloro-5-(5-ethyl-3-methylindol-1-yl)sulfonylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(C)C2=CC(CC)=CC=C2N1S(=O)(=O)C1=CC(Cl)=CC(NCCN(C)C)=C1 NKAMCCAGDLTBSH-UHFFFAOYSA-N 0.000 claims 1
- IMUJJJTYKYGEOA-UHFFFAOYSA-N n-[4-bromo-3-(5-methoxyindol-1-yl)sulfonylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=CC2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC(NCCN(C)C)=CC=C1Br IMUJJJTYKYGEOA-UHFFFAOYSA-N 0.000 claims 1
- NLYIVVGCGPTAMV-UHFFFAOYSA-N n-[4-methoxy-3-(5-methylindol-1-yl)sulfonylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound COC1=CC=C(NCCN(C)C)C=C1S(=O)(=O)N1C2=CC=C(C)C=C2C=C1 NLYIVVGCGPTAMV-UHFFFAOYSA-N 0.000 claims 1
- HMRVFFUGJKMMSM-UHFFFAOYSA-N n-[5-(3-chloroindol-1-yl)sulfonyl-2-methoxyphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(NCCN(C)C)C(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C(Cl)=C1 HMRVFFUGJKMMSM-UHFFFAOYSA-N 0.000 claims 1
- FGGAENZEJSKTOA-UHFFFAOYSA-N n-[5-(5-bromo-3-methylindol-1-yl)sulfonyl-2-chlorophenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(Cl)C(NCCN(C)C)=CC(S(=O)(=O)N2C3=CC=C(Br)C=C3C(C)=C2)=C1 FGGAENZEJSKTOA-UHFFFAOYSA-N 0.000 claims 1
- AECYCTCDGXUYCS-UHFFFAOYSA-N n-[5-(5-bromo-3-methylindol-1-yl)sulfonyl-2-ethylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(NCCN(C)C)C(CC)=CC=C1S(=O)(=O)N1C2=CC=C(Br)C=C2C(C)=C1 AECYCTCDGXUYCS-UHFFFAOYSA-N 0.000 claims 1
- ANXGWDOCXBFJSF-UHFFFAOYSA-N n-[5-(5-bromo-3-methylindol-1-yl)sulfonyl-2-methoxyphenyl]-n',n'-dimethylpropane-1,3-diamine Chemical compound C1=C(NCCCN(C)C)C(OC)=CC=C1S(=O)(=O)N1C2=CC=C(Br)C=C2C(C)=C1 ANXGWDOCXBFJSF-UHFFFAOYSA-N 0.000 claims 1
- HVCWGJMXLHXENN-UHFFFAOYSA-N n-[5-(5-bromoindol-1-yl)sulfonyl-2-ethylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(NCCN(C)C)C(CC)=CC=C1S(=O)(=O)N1C2=CC=C(Br)C=C2C=C1 HVCWGJMXLHXENN-UHFFFAOYSA-N 0.000 claims 1
- JYZCFQKJHHWQCD-UHFFFAOYSA-N n-[5-(5-chloro-3-methylindol-1-yl)sulfonyl-2-methoxyphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(NCCN(C)C)C(OC)=CC=C1S(=O)(=O)N1C2=CC=C(Cl)C=C2C(C)=C1 JYZCFQKJHHWQCD-UHFFFAOYSA-N 0.000 claims 1
- RHLISUBNPIRTTQ-UHFFFAOYSA-N n-[5-(5-chloro-3-methylindol-1-yl)sulfonyl-2-methoxyphenyl]-n',n'-dimethylpropane-1,3-diamine Chemical compound C1=C(NCCCN(C)C)C(OC)=CC=C1S(=O)(=O)N1C2=CC=C(Cl)C=C2C(C)=C1 RHLISUBNPIRTTQ-UHFFFAOYSA-N 0.000 claims 1
- JEYUECZGYPXHKI-UHFFFAOYSA-N n-[5-(5-chloroindol-1-yl)sulfonyl-2-ethylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(NCCN(C)C)C(CC)=CC=C1S(=O)(=O)N1C2=CC=C(Cl)C=C2C=C1 JEYUECZGYPXHKI-UHFFFAOYSA-N 0.000 claims 1
- SWLQWYSGJFLMNA-UHFFFAOYSA-N n-[5-(5-fluoro-3-methylindol-1-yl)sulfonyl-2-methoxyphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(NCCN(C)C)C(OC)=CC=C1S(=O)(=O)N1C2=CC=C(F)C=C2C(C)=C1 SWLQWYSGJFLMNA-UHFFFAOYSA-N 0.000 claims 1
- HLZQYPQCSYLXJM-UHFFFAOYSA-N n-[5-(5-fluoro-3-methylindol-1-yl)sulfonyl-2-methoxyphenyl]-n',n'-dimethylpropane-1,3-diamine Chemical compound C1=C(NCCCN(C)C)C(OC)=CC=C1S(=O)(=O)N1C2=CC=C(F)C=C2C(C)=C1 HLZQYPQCSYLXJM-UHFFFAOYSA-N 0.000 claims 1
- IVHHCRJKTOSJOZ-UHFFFAOYSA-N n-[5-(5-methoxy-3-methylindol-1-yl)sulfonyl-2-methylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(C)C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=C(C)C(NCCN(C)C)=C1 IVHHCRJKTOSJOZ-UHFFFAOYSA-N 0.000 claims 1
- WGPCIRVNMZCVDT-UHFFFAOYSA-N n-[5-(5-methoxy-3-methylindol-1-yl)sulfonyl-2-methylphenyl]-n',n'-dimethylpropane-1,3-diamine Chemical compound C1=C(C)C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=C(C)C(NCCCN(C)C)=C1 WGPCIRVNMZCVDT-UHFFFAOYSA-N 0.000 claims 1
- BEMPNBYYTFNDCC-UHFFFAOYSA-N n-[5-(5-methoxyindol-1-yl)sulfonyl-2-methylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=CC2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=C(C)C(NCCN(C)C)=C1 BEMPNBYYTFNDCC-UHFFFAOYSA-N 0.000 claims 1
- IBZMPWMIZHITGY-UHFFFAOYSA-N n-[5-(5-methoxyindol-1-yl)sulfonyl-2-methylphenyl]-n',n'-dimethylpropane-1,3-diamine Chemical compound C1=CC2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=C(C)C(NCCCN(C)C)=C1 IBZMPWMIZHITGY-UHFFFAOYSA-N 0.000 claims 1
- LNONTHJOZDFIMJ-UHFFFAOYSA-N n-[5-(6-chloroindol-1-yl)sulfonyl-2-methylphenyl]-n',n'-dimethylethane-1,2-diamine Chemical compound C1=C(C)C(NCCN(C)C)=CC(S(=O)(=O)N2C3=CC(Cl)=CC=C3C=C2)=C1 LNONTHJOZDFIMJ-UHFFFAOYSA-N 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract 2
- 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
- 201000011529 cardiovascular cancer Diseases 0.000 abstract 1
- 208000015114 central nervous system disease Diseases 0.000 abstract 1
- 208000014951 hematologic disease Diseases 0.000 abstract 1
- 208000023504 respiratory system disease Diseases 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
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Abstract
Spoj formule (I) naznačen time što R1 predstavlja vodik, hidroksil, halogen, (C1-C3)alkil, halogen(C1-C3)alkil, (C1-C3)alkoksi, halogen(C1-C3)alkoksi, ciklo(C3-C6)alkil ili ciklo(C3-C6)alkoksi; R2 predstavlja vodik, halogen, (C1-C3)alkil, halogen(C1-C3)alkil, (C1-C3)alkoksi ili halogen(C1-C3)alkoksi, ciklo(C3-C6)alkil ili ciklo(C3-C6)alkoksi; R predstavlja vodik ili (C1-C3)alkil ili (C3-C6)cikloalkil; "n" predstavlja 0 do 4; "p" predstavlja 0 do 6; "q" predstavlja 0 do 4. Patent sadrži još 12 patentnih zahtjeva.
Claims (13)
1. Spoj formule (I)
[image]
naznačen time što R1 predstavlja vodik, hidroksil, halogen, (C1-C3)alkil, halogen(C1-C3)alkil, (C1-C3)alkoksi, halogen(C1-C3)alkoksi, ciklo(C3-C6)alkil ili ciklo(C3-C6)alkoksi;
R2 predstavlja vodik, halogen, (C1-C3)alkil, halogen(C1-C3)alkil, (C1-C3)alkoksi ili halogen(C1-C3)alkoksi, ciklo(C3-C6)alkil ili ciklo(C3-C6)alkoksi;
R predstavlja vodik ili (C1-C3)alkil ili (C3-C6)cikloalkil;
"n" predstavlja 0 do 4;
"p" predstavlja 0 do 6;
"q" predstavlja 0 do 4.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što R1 je po mogućnosti vodik, hidroksil, halogen, (C1-C3)alkil, halogen(C1-C3)alkil, (C1-C3)alkoksi ili halogen(C1-C3)alkoksi.
3. Spoj u skladu s patentnim zahtjevom 1, naznačen time što R2 je po mogućnosti vodik, halogen, (C1-C3)alkil, halogen(C1-C3)alkil, (C1-C3)alkoksi, halogen(C1-C3)alkoksi, ciklo(C3-C6)alkil ili ciklo(C3-C6)alkoksi.
4. Spoj u skladu s patentnim zahtjevom 1, naznačen time što R je po mogućnosti vodik ili (C1-C3)alkil.
5. Spoj u skladu s patentnim zahtjevom 1, naznačen time što ga se bira se iz skupine koju čine:
N'-[2-Metoksi-5-(5-metoksi-3-metilindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[5-(3-Klor-5-metoksiindolo-1-sulfonil)-2-metoksifenil]-N,N-dimetileten-1,2-diamin;
N'-[5-(3-Klor-indol-1-sulfonil)-2-metoksifenil]-N,N-dimetiletan-1,2-diamin;
N'-[5-(Indol-1-sulfonil)-2-metoksifenil]-N,N-dimetiletan-1,2-diamin;
N'-[2-Metoksi-5-(3-metilindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[5-(5-Metoksi-3-metilindol-1-sulfonil)-2-metilfenil]-N,N-dimetilpropan-1,3-diamin;
N'-[5-(5-Metoksiindol-1-sulfonil)-2-metilfenil]-N,N-dimetiletan-1,2-diamin;
N'-[5-(5-Metoksi-3-metilindol-1-sulfonil)-2-metilfenil]-N,N-dimetiletan-1,2-diamin;
N'-[5-(5-Metoksiindol-1-sulfonil)-2-metilfenil]-N,N-dimetilpropan-1,3-diamin;
N'-[3-(4-Klor-3-metilindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[3-(5-Klor-3-metilindol-1-sulfonil)-2-etilfenil]-N,N-dimetiletan-1,2-diamin;
N'-[2-Etil-5-(5-fluor-3-metilindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[2-Etil-5-(5-fluorindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[2-Etil-5-(5-klorindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[2-Etil-5-(5-metoksi-3-metilindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[3-(5-Izopropoksi-3-metilindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[5-(5-Brom-3-metilindol-1-sulfonil)-2-klorfenil]-N,N-dimetiletan-1,2-diamin;
N'-[3-(5-Etoksi-3-metilindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[5-(5-Brom-3-metilindol-1-sulfonil)-2-etilfenil]-N,N-dimetiletan-1,2-diamin;
N'-[5-(6-Klorindol-1-sulfonil)-2-metilfenil]-N,N-dimetiletan-1,2-diamin;
N'-[3-(5-Bromindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[3-(5-Izopropoksiindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[3-(6-Klorindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[5-(5-Bromindol-1-sulfonil)-2-etilfenil]-N,N-dimetiletan-1,2-diamin;
N'-[3-(4-Klorindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[2-Etil-5-(5-metoksiindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[3-(5-Metoksi-3-metilindol-1-sulfonil)fenil]-N,N-dimetilpropan-1,3-diamin;
N'-[2-Metoksi-5-(5-klor-3-metilindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[3-(5-Metoksi-3-metilindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[2-Metoksi-5-(5-klor-3-metilindol-1-sulfonil)fenil]-N,N-dimetilpropan-1,3-diamin;
N'-[2-Metoksi-5-(3-metilindol-1-sulfonil)fenil]-N,N-dimetilpropan-1,3-diamin;
N'-[2-Metoksi-5-(5-brom-3-metilindol-1-sulfonil)fenil]-N,N-dimetilpropan-1,3-diamin;
N'-[2-Metoksi-5-(5-fluor-3-metilindol-1-sulfonil)fenil]-N,N-dimetilpropan-1,3-diamin;
N'-[2-Metoksi-5-(5-fluor-3-metilindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[2-Metoksi-5-(5-metoksi-3-metilindol-1-sulfonil)fenil]-N,N-dimetilpropan-1,3-diamin;
N'-[3-(5-Fluor-3-metilindol-1-sulfonil)-5-metoksifenil]-N,N-dimetiletan-1,2-diamin;
N'-[3-Klor-5-(5-etil-3-metilindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[3-(5-Fluor-3-metilindol-1-sulfonil)-5-metilfenil]-N,N-dimetiletan-1,2-diamin;
N'-[4-Metoksi-3-(5-metilindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[4-Brom-3-(5-metoksiindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
N'-[3-(5-Etil-3-metilindol-1-sulfonil)-4-metilfenil]-N,N-dimetiletan-1,2-diamin;
N'-[2-Klor-3-(5-metoksi-2-metilindol-1-sulfonil)fenil]-N,N-dimetiletan-1,2-diamin;
njihovi stereoizomeri i njihove farmaceutski prihvatljive soli.
6. 5. Postupak dobivanja spoja formule (I)
[image]
gdje R1 predstavlja vodik, hidroksil, halogen, (C1-C3)alkil, halogen(C1-C3)alkil, (C1-C3)alkoksi, halogen(C1-C3)alkoksi, ciklo(C3-C6)alkil ili ciklo(C3-C6)alkoksi;
R2 predstavlja vodik, halogen, (C1-C3)alkil, halogen(C1-C3)alkil, (C1-C3)alkoksi ili halogen(C1-C3)alkoksi, ciklo(C3-C6)alkil ili ciklo(C3-C6)alkoksi;
R predstavlja vodik ili (C1-C3)alkil ili (C3-C6)cikloalkil;
"n" predstavlja 0 do 4;
"p" predstavlja 0 do 6;
"q" predstavlja 0 do 4; naznačen time što se sastoji u reakciji spoja formule (a)
[image]
gdje su svi supstituenti kao stoje opisano gore;
s aminskim derivatima, uz upotrebu pogodne baze, u prisutnosti inertnog otapala, na temperaturi okoliša.
7. 6. Postupak u skladu s patentnim zahtjevom 6, naznačen time što se navedenu bazu bira između kalijevog karbonata i natrijevog hidroksida.
8. 7. Postupak u skladu s patentnim zahtjevom 6 i/ili 7, naznačen time što se navedeno inertno otapalo bira između diklormetana, dimetilformamida, dimetil-sulfoksida i w-ksilena.
9. 8. Farmaceutski pripravak, naznačen time što sadrži spoj formule (I) u skladu s patentnim zahtjevom 1 do 5 i farmaceutski prihvatljivu podlogu, razrjeđivač, pomoćnu tvar ili solvat.
10. 9. 10. Farmaceutski pripravak u skladu s patentnim zahtjevom 9, naznačen time stoje u obliku tablete, kapsule, praška, sirupa, otopine, injekcije ili suspenzije i primijenjuje se kao jednu dozu ili više jedinica doze.
11. 10. 11. Farmaceutski pripravak u skladu s patentnim zahtjevom 9 i/ili 10, naznačen time stoje namijenjen upotrebi u liječenju bolesti ili poremećaja središnjeg živčanog sustava povezanih s ili pod utjecajem receptora 5-HT6 i bira ih se iz skupine koju čine motorički poremećaj, anksiozni poremećaj, kognitivni poremećaj, neurodegenerativni poremećaj, Alzheimerova bolest, Huntingtonova koreja, gastrointestinalni, kognitivni poremećaj povezan sa shizofrenijom, blagi kognitivni poremećaj, poremećaji hranjenja, anksioznost, depresija, pretilost i/ili Parkinsonova bolest.
12. 11. Spoj formule (I), u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što ga se upotrebljava u proizvodnji medikamenta za liječenje ili sprječavanje bolesti ili poremećaja središnjeg živčanog sustava povezanih s ili pod utjecajem receptora 5-HT6 i bira ih se iz skupine koju čine motorički poremećaj, anksiozni poremećaj, kognitivni poremećaj, neurodegenerativni poremećaj, Alzheimerova bolest, Huntingtonova koreja, gastrointestinalni, kognitivni poremećaj povezan sa shizofrenijom, poremećaji hranjenja, anksioznost, depresija, pretilost i/ili Parkinsonova bolest.
13. 12. Sredstvo za sprječavanje ili liječenje bolesti ili poremećaja središnjeg živčanog sustava povezanih s ili pod utjecajem receptora 5-HT6 i biraju se iz skupine koju čine motorički poremećaj, anksiozni poremećaj, kognitivni poremećaj, neurodegenerativni poremećaj, Alzheimerova bolest, Huntingtonova koreja, gastrointestinalni, kognitivni poremećaj povezan sa shizofrenijom, poremećaji hranjenja, anksioznost, depresija, pretilost i/ili Parkinsonova bolest; naznačeno time što kao aktivni sastojak sadrži spoj formule (I) u skladu s bilo kojim od prethodnih patentnih zahtjeva.
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CA2862363C (en) * | 2012-02-02 | 2021-06-08 | Joan M. Fallon | Enzyme compositions and use thereof for wound healing |
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IL205231A0 (en) | 2010-12-30 |
EP2200980A1 (en) | 2010-06-30 |
US20100216861A1 (en) | 2010-08-26 |
CN101835748A (zh) | 2010-09-15 |
AU2008315309B2 (en) | 2011-06-09 |
ZA201002165B (en) | 2011-05-25 |
SI2200980T1 (sl) | 2011-12-30 |
MX2010003765A (es) | 2010-04-30 |
CA2703157C (en) | 2013-02-05 |
JP2011500792A (ja) | 2011-01-06 |
CA2703157A1 (en) | 2009-04-30 |
CY1112181T1 (el) | 2015-12-09 |
US7964627B2 (en) | 2011-06-21 |
JP5236001B2 (ja) | 2013-07-17 |
WO2009053997A1 (en) | 2009-04-30 |
ATE518833T1 (de) | 2011-08-15 |
KR20100069707A (ko) | 2010-06-24 |
KR101268654B1 (ko) | 2013-05-29 |
CN101835748B (zh) | 2012-11-14 |
ES2370680T9 (es) | 2012-02-15 |
HRP20110780T1 (hr) | 2011-11-30 |
IL205231A (en) | 2014-03-31 |
EP2200980B1 (en) | 2011-08-03 |
AU2008315309A1 (en) | 2009-04-30 |
ES2370680T3 (es) | 2011-12-21 |
EA017154B1 (ru) | 2012-10-30 |
DK2200980T3 (da) | 2011-11-21 |
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