HRP20110041T1 - Derivati karbazola kao funkcionalni ligandi 5-ht6 - Google Patents
Derivati karbazola kao funkcionalni ligandi 5-ht6 Download PDFInfo
- Publication number
- HRP20110041T1 HRP20110041T1 HR20110041T HRP20110041T HRP20110041T1 HR P20110041 T1 HRP20110041 T1 HR P20110041T1 HR 20110041 T HR20110041 T HR 20110041T HR P20110041 T HRP20110041 T HR P20110041T HR P20110041 T1 HRP20110041 T1 HR P20110041T1
- Authority
- HR
- Croatia
- Prior art keywords
- carbazol
- dimethylamine
- tetrahydro
- compound
- formula
- Prior art date
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- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title abstract 3
- 239000003446 ligand Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 21
- 150000003839 salts Chemical class 0.000 claims abstract 9
- 108091005435 5-HT6 receptors Proteins 0.000 claims abstract 4
- 238000000034 method Methods 0.000 claims abstract 4
- 239000003814 drug Substances 0.000 claims abstract 3
- 229940079593 drug Drugs 0.000 claims abstract 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 22
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 8
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- VXHXQVRVORPRKU-UHFFFAOYSA-N 6-bromo-9-(2,3-dichlorophenyl)sulfonyl-n,n-dimethyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1C(N(C)C)CCC2=C1C1=CC(Br)=CC=C1N2S(=O)(=O)C1=CC=CC(Cl)=C1Cl VXHXQVRVORPRKU-UHFFFAOYSA-N 0.000 claims 1
- XHFATGOAAZZKLX-UHFFFAOYSA-N 6-bromo-9-(2-bromophenyl)sulfonyl-n,n-dimethyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1C(N(C)C)CCC2=C1C1=CC(Br)=CC=C1N2S(=O)(=O)C1=CC=CC=C1Br XHFATGOAAZZKLX-UHFFFAOYSA-N 0.000 claims 1
- FHTVXPHFFOANMZ-UHFFFAOYSA-N 6-bromo-9-(4-bromophenyl)sulfonyl-n,n-dimethyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1C(N(C)C)CCC2=C1C1=CC(Br)=CC=C1N2S(=O)(=O)C1=CC=C(Br)C=C1 FHTVXPHFFOANMZ-UHFFFAOYSA-N 0.000 claims 1
- OCKCNFOQIXKHHQ-UHFFFAOYSA-N 6-bromo-9-(4-fluorophenyl)sulfonyl-n,n-dimethyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1C(N(C)C)CCC2=C1C1=CC(Br)=CC=C1N2S(=O)(=O)C1=CC=C(F)C=C1 OCKCNFOQIXKHHQ-UHFFFAOYSA-N 0.000 claims 1
- TVWJLEDPDYVIAF-UHFFFAOYSA-N 6-bromo-9-(4-methoxyphenyl)sulfonyl-n,n-dimethyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(Br)C=C2C2=C1CCC(N(C)C)C2 TVWJLEDPDYVIAF-UHFFFAOYSA-N 0.000 claims 1
- FJDBTILNQCEBQX-UHFFFAOYSA-N 6-bromo-n,n-dimethyl-9-(4-propan-2-ylphenyl)sulfonyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC=C(Br)C=C2C2=C1CCC(N(C)C)C2 FJDBTILNQCEBQX-UHFFFAOYSA-N 0.000 claims 1
- OHLIBZZIOZMXIN-UHFFFAOYSA-N 6-bromo-n,n-dimethyl-9-[3-(trifluoromethyl)phenyl]sulfonyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1C(N(C)C)CCC2=C1C1=CC(Br)=CC=C1N2S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 OHLIBZZIOZMXIN-UHFFFAOYSA-N 0.000 claims 1
- CHNGIMXRHADLSO-UHFFFAOYSA-N 6-chloro-9-(4-fluorophenyl)sulfonyl-n,n-dimethyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1C(N(C)C)CCC2=C1C1=CC(Cl)=CC=C1N2S(=O)(=O)C1=CC=C(F)C=C1 CHNGIMXRHADLSO-UHFFFAOYSA-N 0.000 claims 1
- XJSQPVGIUSJIDS-UHFFFAOYSA-N 6-chloro-n,n-dimethyl-9-(4-methylphenyl)sulfonyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1C(N(C)C)CCC2=C1C1=CC(Cl)=CC=C1N2S(=O)(=O)C1=CC=C(C)C=C1 XJSQPVGIUSJIDS-UHFFFAOYSA-N 0.000 claims 1
- BBSVXLFIZJQQOV-UHFFFAOYSA-N 6-chloro-n,n-dimethyl-9-[3-(trifluoromethyl)phenyl]sulfonyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1C(N(C)C)CCC2=C1C1=CC(Cl)=CC=C1N2S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 BBSVXLFIZJQQOV-UHFFFAOYSA-N 0.000 claims 1
- LZILBCGLADWRRO-UHFFFAOYSA-N 6-fluoro-9-(4-fluorophenyl)sulfonyl-n,n-dimethyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1C(N(C)C)CCC2=C1C1=CC(F)=CC=C1N2S(=O)(=O)C1=CC=C(F)C=C1 LZILBCGLADWRRO-UHFFFAOYSA-N 0.000 claims 1
- QHQSBPRWLHRWAQ-UHFFFAOYSA-N 6-fluoro-n,n-dimethyl-9-(4-methylphenyl)sulfonyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1C(N(C)C)CCC2=C1C1=CC(F)=CC=C1N2S(=O)(=O)C1=CC=C(C)C=C1 QHQSBPRWLHRWAQ-UHFFFAOYSA-N 0.000 claims 1
- ZLSXIXYITXPSOC-UHFFFAOYSA-N 6-fluoro-n,n-dimethyl-9-(4-propan-2-ylphenyl)sulfonyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC=C(F)C=C2C2=C1CCC(N(C)C)C2 ZLSXIXYITXPSOC-UHFFFAOYSA-N 0.000 claims 1
- VKSRBIPXHKGXHU-UHFFFAOYSA-N 6-methoxy-9-(4-methoxyphenyl)sulfonyl-n,n-dimethyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(OC)C=C2C2=C1CCC(N(C)C)C2 VKSRBIPXHKGXHU-UHFFFAOYSA-N 0.000 claims 1
- ALWRRUFJVQDOPL-UHFFFAOYSA-N 6-methoxy-n,n-dimethyl-9-(4-methylphenyl)sulfonyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1=2CCC(N(C)C)CC=2C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=C(C)C=C1 ALWRRUFJVQDOPL-UHFFFAOYSA-N 0.000 claims 1
- ADGNYVSGEVQHLZ-UHFFFAOYSA-N 6-methoxy-n,n-dimethyl-9-[3-(trifluoromethyl)phenyl]sulfonyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1=2CCC(N(C)C)CC=2C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 ADGNYVSGEVQHLZ-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- SRCUGVUYMUSXIR-UHFFFAOYSA-N 9-(3-chlorophenyl)sulfonyl-n,n-dimethyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1C(N(C)C)CCC2=C1C1=CC=CC=C1N2S(=O)(=O)C1=CC=CC(Cl)=C1 SRCUGVUYMUSXIR-UHFFFAOYSA-N 0.000 claims 1
- BYIPSJSCVXORRR-UHFFFAOYSA-N 9-(4-bromophenyl)sulfonyl-6-chloro-n,n-dimethyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1C(N(C)C)CCC2=C1C1=CC(Cl)=CC=C1N2S(=O)(=O)C1=CC=C(Br)C=C1 BYIPSJSCVXORRR-UHFFFAOYSA-N 0.000 claims 1
- SZOUKQKLAZNOSX-UHFFFAOYSA-N 9-(4-bromophenyl)sulfonyl-6-fluoro-n,n-dimethyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1C(N(C)C)CCC2=C1C1=CC(F)=CC=C1N2S(=O)(=O)C1=CC=C(Br)C=C1 SZOUKQKLAZNOSX-UHFFFAOYSA-N 0.000 claims 1
- JDJZZFHUUVRNHZ-UHFFFAOYSA-N 9-(4-bromophenyl)sulfonyl-6-methoxy-n,n-dimethyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1=2CCC(N(C)C)CC=2C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=C(Br)C=C1 JDJZZFHUUVRNHZ-UHFFFAOYSA-N 0.000 claims 1
- INOVOZTXOHBWOI-UHFFFAOYSA-N 9-(4-fluorophenyl)sulfonyl-6-methoxy-n,n-dimethyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1=2CCC(N(C)C)CC=2C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=C(F)C=C1 INOVOZTXOHBWOI-UHFFFAOYSA-N 0.000 claims 1
- UZKROYHPNXXRML-UHFFFAOYSA-N 9-(4-methoxyphenyl)sulfonyl-n,n-dimethyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C2=C1CCC(N(C)C)C2 UZKROYHPNXXRML-UHFFFAOYSA-N 0.000 claims 1
- BPDIPISJQZBBJL-UHFFFAOYSA-N 9-(benzenesulfonyl)-6-bromo-n,n-dimethyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1C(N(C)C)CCC2=C1C1=CC(Br)=CC=C1N2S(=O)(=O)C1=CC=CC=C1 BPDIPISJQZBBJL-UHFFFAOYSA-N 0.000 claims 1
- UQXLBDBXJGUYAE-UHFFFAOYSA-N 9-(benzenesulfonyl)-6-chloro-n,n-dimethyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1C(N(C)C)CCC2=C1C1=CC(Cl)=CC=C1N2S(=O)(=O)C1=CC=CC=C1 UQXLBDBXJGUYAE-UHFFFAOYSA-N 0.000 claims 1
- TYJYBRVLMVDOMJ-UHFFFAOYSA-N 9-(benzenesulfonyl)-6-fluoro-n,n-dimethyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1C(N(C)C)CCC2=C1C1=CC(F)=CC=C1N2S(=O)(=O)C1=CC=CC=C1 TYJYBRVLMVDOMJ-UHFFFAOYSA-N 0.000 claims 1
- WJGHDFLJHZUCKM-UHFFFAOYSA-N 9-(benzenesulfonyl)-6-methoxy-n,n-dimethyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1=2CCC(N(C)C)CC=2C2=CC(OC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 WJGHDFLJHZUCKM-UHFFFAOYSA-N 0.000 claims 1
- DXPHMVPLORWBKA-UHFFFAOYSA-N 9-(benzenesulfonyl)-n,n-dimethyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1C(N(C)C)CCC2=C1C1=CC=CC=C1N2S(=O)(=O)C1=CC=CC=C1 DXPHMVPLORWBKA-UHFFFAOYSA-N 0.000 claims 1
- VFIXEEIIZUMLIG-UHFFFAOYSA-N 9-(benzenesulfonyl)-n,n-dimethyl-6-methylsulfanyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1=2CCC(N(C)C)CC=2C2=CC(SC)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 VFIXEEIIZUMLIG-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 206010019196 Head injury Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- LYGXTKJBXJMAQL-UHFFFAOYSA-N n,n-dimethyl-9-(4-methylphenyl)sulfonyl-6-methylsulfanyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1=2CCC(N(C)C)CC=2C2=CC(SC)=CC=C2N1S(=O)(=O)C1=CC=C(C)C=C1 LYGXTKJBXJMAQL-UHFFFAOYSA-N 0.000 claims 1
- IAMTYBROQNVCMZ-UHFFFAOYSA-N n,n-dimethyl-9-(4-propan-2-ylphenyl)sulfonyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N1C2=CC=CC=C2C2=C1CCC(N(C)C)C2 IAMTYBROQNVCMZ-UHFFFAOYSA-N 0.000 claims 1
- XNHXAWXVLOOHSD-UHFFFAOYSA-N n,n-dimethyl-9-[3-(trifluoromethyl)phenyl]sulfonyl-1,2,3,4-tetrahydrocarbazol-3-amine Chemical compound C1C(N(C)C)CCC2=C1C1=CC=CC=C1N2S(=O)(=O)C1=CC=CC(C(F)(F)F)=C1 XNHXAWXVLOOHSD-UHFFFAOYSA-N 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- -1 pyrrolopyridinyl Chemical group 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 108020003175 receptors Proteins 0.000 abstract 1
- 102000005962 receptors Human genes 0.000 abstract 1
Classifications
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- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- 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
- A61P25/20—Hypnotics; Sedatives
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- 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
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
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- 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
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
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- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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Abstract
Spoj formule (I), ili njegova farmaceutski prihvatljiva sol, naznačen time što: isprekidana linija "----" predstavlja izbornu dvostruku vezu; Ar predstavlja bilo koju skupinu koju se bira između fenila, naftila, monocikličkog ili bicikličkog heteroarila, od kojih svaki može biti daljnje supstituiran s jednim ili više neovisnih supstituenata, definiranih kao R1; Ar-, primjerice, može biti, R1 predstavlja jednu ili više supstitucija na benzenskom prstenu i uključuje vodik, halogen, cijano, (C1-C3)alkil, halogen(C1-C3)alkil, (C1-C3)alkoksi, halogen(C1-C3)alkoksi, ciklo(C3-C6)alkil ili ciklo(C3-C6)alkoksi; R predstavlja bilo vodik ili (C1-C3)alkil; "n" predstavlja cijeli broj, bilo 1 ili 2; i uključuje njegove moguće stereoizomere. Patent sadrži još 13 patentnih zahtjeva.
Claims (14)
1. Spoj formule (I),
[image]
ili njegova farmaceutski prihvatljiva sol, naznačen time što: isprekidana linija "----" predstavlja izbornu dvostruku vezu; Ar predstavlja bilo koju skupinu koju se bira između fenila, naftila, monocikličkog ili bicikličkog heteroarila, od kojih svaki može biti daljnje supstituiran s jednim ili više neovisnih supstituenata, definiranih kao R1; Ar-, primjerice, može biti,
[image]
R1 predstavlja jednu ili više supstitucija na benzenskom prstenu i uključuje vodik, halogen, cijano, (C1-C3)alkil, halogen(C1-C3)alkil, (C1-C3)alkoksi, halogen(C1-C3)alkoksi, ciklo(C3-C6)alkil ili ciklo(C3-C6)alkoksi; R predstavlja bilo vodik ili (C1-C3)alkil; "n" predstavlja cijeli broj, bilo 1 ili 2; i uključuje njegove moguće stereoizomere.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što vrijednost "n" je 1, prikazan niže
[image]
ili njegova farmaceutski prihvatljiva sol.
3. Spoj u skladu s patentnim zahtjevom 1, naznačen time što vrijednost "n" je 1, a dvostruka veza je prisutna kao što slijedi
[image]
ili njegova farmaceutski prihvatljiva sol.
4. Spoj u skladu s patentnim zahtjevom 1, naznačen time što vrijednost za "n" je 2, kao što slijedi
[image]
ili njegova farmaceutski prihvatljiva sol.
5. Spoj u skladu s patentnim zahtjevom 1, naznačen time što vrijednost za "n" je 2, a dvostruka veza je također prisutna kao što slijedi
[image]
ili njegova farmaceutski prihvatljiva sol.
6. Spoj u skladu s patentnim zahtjevom 1, naznačen time što Ar je fenil, naftil, indolil, indazolil, pirolopiridinil, benzofuranil, benzotienil ili benzimidazolil.
7. Spoj u skladu s patentnim zahtjevom 1, naznačen time što R1 je vodik, halogen, perhalogenalkil, perhalogenalkoksi, cijano, (C1-C3) alkil, halogen(C1-C3)alkil, (C1-C3)alkoksi, halogen(C1-C3)alkoksi, alkoksi(C1-C3)alkoksi, hidroksi(C1-C3)alkoksi, ciklo (C3-C6)alkil ili ciklo(C3-C6)alkoksi.
8. Spoj u skladu s patentnim zahtjevom 1, naznačen time što ga se bira iz sljedeće skupine:
(9-Benzensulfonil-2,3,4,9-tetrahidro-1H-karbazol-3-il)dimetilamin;
9-[(4-Brombenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
9-[(4-Fluorbenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
9-[(4-Metilbenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[9-(3-Klorbenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[9-(4-Izopropilbenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[9-(3-Trifluormetilbenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[9-(4-Metoksibenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Brom-9-(benzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Brom-9-(4-brombenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Brom-9-(4-flourobenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Brom-9-(4-isopropilbenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Brom-9-(3-trifluotometilbenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Brom-9-(2-brombenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Brom-9-(4-metoksibenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Klor-9-benzensulfonil-2,3,4,9-tetrahidro-1H-karbazol-3-il] dimetilamin;
[6-Klor-9-(3-triflurometilbenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Klor-9-(4-metilbenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Klor-9-(4-brombenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Klor-9-(4-fluorbenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Fluor-9-benzensulfonil-2,3,4,9-tetrahidro-1H-karbazol-3-il] dimetilamin;
[6-Fluor-9-(4-metilbenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Fluor-9-(4-isopropilbenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Fluor-9-(4-brombenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Fluor-9-(4-fluorbenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Metoksi-9-benzensulfonil-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Metoksi-9-(4-metilbenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Metoksi-9-(4-metoksibenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Metoksi-9-(4-brombenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Metoksi-9-(4-fluorbenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Metoksi-9-(3-trifluormetilbenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Metiltio-9-benzensulfonil-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Metiltio-9-(4-metilbenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Metiltio-9-(4-brombenzensulfonil-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Metiltio-9-(4-Fluorbenzensulfonil-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Klor-9-(2-brombenzensulfonil-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6,8-Difluor-9-(4-metilbenzensulfonil-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6,8-Difluor-9-(benzensulfonil-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Brom-9-(2,3-diklorbenzensulfonil)-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Metiltio-9-(2,3-diklorbenzensulfonil-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Metiltio-9-(4-metoksibenzensulfonil-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
[6-Metiltio-9-(3-klorbenzensulfonil-2,3,4,9-tetrahidro-1H-karbazol-3-il]dimetilamin;
njihovih stereoizomera; i njihovih soli.
9. Postupak dobivanja spoja formule (I)
[image]
ili njegove farmaceutski prihvatljive soli, gdje: isprekidana linija "----" predstavlja izbornu dvostruku vezu; Ar predstavlja bilo koju skupinu koju se bira između fenila, naftila, monocikličkog ili bicikličkog heteroarila, od kojih svaki može biti daljnje supstituiran s jednim ili više neovisni supstituenata, definiranih kao R1; Ar-, primjerice, može biti,
[image]
R1 predstavlja jednu ili više supstitucija na benzenskom prstenu i uključuje vodik, halogen, cijano, (C1-C3) alkil, halogen(C1-C3)alkil, (C1-C3)alkoksi, halogen(C1-C3)alkoksi, ciklo(C3-C6)alkil ili ciklo(C3-C6)alkoksi; R predstavlja bilo vodik ili (C1-C3)alkil; "n" predstavlja cijeli broj, bilo I ili 2; i uključuje njegove moguće stereoizomere; naznačen time što navedeni postupak se sastoji u miješanju spoja formule (a), gdje svi supstitutenti poput n, R1, R i Ar su definirani kao za spoj formule (I), gore, sa sulfonskim derivatom formule (b):
[image]
gdje Ar je definiran kao za spoj formule (I), gore; a Lg predstavlja X kao atom halogena (primjerice fluor, klor ili jod); u prisutnosti pogodne baze i inertnog otapala, na temperaturi okoliša, kako bi se dobilo spoj formule (I).
10. Postupak u skladu s patentnim zahtjevom 9, naznačen time što se izborno sastoji u:
1. prevođenju spoja formule (I) u drugi spoj formule (I)
2. uklanjanju bilo koje zaštitne skupine; ili
3. dobivanju njegove farmaceutski prihvatljive soli, solvata ili predlijeka.
11. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 8, naznačen time što je namijenjen upotrebi u liječenju poremećaja središnjeg živčanog sustava povezanog s ili pod utjecajem receptora 5-HT6 kodpacijenta kojem je to potrebno, primjerice anksioznog poremećaja, kognitivnog poremećaja ili neurodegenerativnog poremećaja, Alzheimerove bolesti ili Parkinsonova bolesti, poremećaja nedostatka pažnje ili opsesivno-kompulzivnog poremećaja, inzulta ili ozljede glave, poremećaja hranjenja ili pretilosti.
12. Farmaceutski pripravak, naznačen time što sadrži farmaceutski prihvatljivu podlogu i djelotvornu količinu spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 8.
13. Spoj formule (I), u skladu s bilo kojim od patentnih zahtjeva 1 do 8, naznačen time što je namijenjen upotrebi kao medikament.
14. Upotreba spoja formule (I), u skladu s bilo kojim od patentnih zahtjeva 1 do 8, naznačena time što je navedeni spoj namijenjen proizvodnji medikamenta za liječenje poremećaja središnjeg živčanog sustava povezan s ili pod utjecajem receptora 5-HT6.
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| IN1504CH2005 | 2005-10-19 | ||
| PCT/IN2006/000195 WO2007046111A1 (en) | 2005-10-19 | 2006-06-09 | Carbazole derivatives as functional 5-ht6 ligands |
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| US (1) | US8143303B2 (hr) |
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| JP (1) | JP2009512681A (hr) |
| KR (1) | KR101125820B1 (hr) |
| CN (1) | CN101291670B (hr) |
| AT (1) | ATE485040T1 (hr) |
| AU (1) | AU2006305502B2 (hr) |
| BR (1) | BRPI0619308A2 (hr) |
| CA (1) | CA2626646C (hr) |
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| DK (1) | DK1948166T3 (hr) |
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| CN106045972B (zh) * | 2016-06-03 | 2018-11-16 | 中山大学 | 咔唑-利凡斯的明二联体及其药物组合物和应用 |
| CN106749184B (zh) * | 2016-11-15 | 2020-07-17 | 中山大学 | 8-氨基喹啉-羟基咔唑杂联体，其制备方法及其药物组合物 |
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| EP1434578A1 (en) * | 2001-10-09 | 2004-07-07 | PHARMACIA & UPJOHN COMPANY | Arylsulphonyl-substituted tetrahydro- and hexahydro-carbazoles as 5-ht-6 receptor ligands |
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- 2006-06-09 EA EA200801114A patent/EA014694B1/ru not_active IP Right Cessation
- 2006-06-09 JP JP2008536206A patent/JP2009512681A/ja active Pending
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- 2006-06-09 AT AT06766266T patent/ATE485040T1/de active
- 2006-06-09 AU AU2006305502A patent/AU2006305502B2/en not_active Ceased
- 2006-06-09 KR KR1020087010404A patent/KR101125820B1/ko active IP Right Grant
- 2006-06-09 WO PCT/IN2006/000195 patent/WO2007046111A1/en active Application Filing
- 2006-06-09 PT PT06766266T patent/PT1948166E/pt unknown
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- 2006-06-09 CN CN2006800390082A patent/CN101291670B/zh not_active Expired - Fee Related
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- 2006-06-09 EP EP06766266A patent/EP1948166B1/en active Active
- 2006-06-09 BR BRPI0619308-0A patent/BRPI0619308A2/pt not_active Application Discontinuation
- 2006-06-09 DK DK06766266.8T patent/DK1948166T3/da active
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Also Published As
| Publication number | Publication date |
|---|---|
| US20100189646A1 (en) | 2010-07-29 |
| RS51627B (en) | 2011-08-31 |
| EP1948166B1 (en) | 2010-10-20 |
| JP2009512681A (ja) | 2009-03-26 |
| CN101291670B (zh) | 2012-07-04 |
| NZ567865A (en) | 2010-07-30 |
| CA2626646C (en) | 2011-03-01 |
| AU2006305502A1 (en) | 2007-04-26 |
| CN101291670A (zh) | 2008-10-22 |
| BRPI0619308A2 (pt) | 2013-03-05 |
| HK1120424A1 (en) | 2009-04-03 |
| KR20080064848A (ko) | 2008-07-09 |
| ATE485040T1 (de) | 2010-11-15 |
| EA200801114A1 (ru) | 2009-02-27 |
| NO341252B1 (no) | 2017-09-25 |
| PT1948166E (pt) | 2011-01-19 |
| SI1948166T1 (sl) | 2011-02-28 |
| ZA200803118B (en) | 2011-11-30 |
| EA014694B1 (ru) | 2010-12-30 |
| KR101125820B1 (ko) | 2012-03-28 |
| ES2354455T3 (es) | 2011-03-15 |
| US8143303B2 (en) | 2012-03-27 |
| DK1948166T3 (da) | 2011-01-31 |
| CA2626646A1 (en) | 2007-04-26 |
| CY1111560T1 (el) | 2015-10-07 |
| NO20081739L (no) | 2008-07-09 |
| EP1948166A1 (en) | 2008-07-30 |
| PL1948166T3 (pl) | 2011-04-29 |
| AU2006305502B2 (en) | 2009-11-26 |
| WO2007046111A1 (en) | 2007-04-26 |
| DE602006017722D1 (de) | 2010-12-02 |
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