JP4500454B2 - １，４−ジアザビシクロ［３．２．２］ノナン−４−カルボキシレートおよびカルボキサミド誘導体、治療におけるその製造ならびに使用 - Google Patents
１，４−ジアザビシクロ［３．２．２］ノナン−４−カルボキシレートおよびカルボキサミド誘導体、治療におけるその製造ならびに使用 Download PDFInfo
- Publication number
- JP4500454B2 JP4500454B2 JP2000608013A JP2000608013A JP4500454B2 JP 4500454 B2 JP4500454 B2 JP 4500454B2 JP 2000608013 A JP2000608013 A JP 2000608013A JP 2000608013 A JP2000608013 A JP 2000608013A JP 4500454 B2 JP4500454 B2 JP 4500454B2
- Authority
- JP
- Japan
- Prior art keywords
- nonane
- diazabicyclo
- group
- formula
- alkyl
- 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.)
- Expired - Fee Related
Links
- 238000002360 preparation method Methods 0.000 title description 2
- RUFBGPCDOFYGTF-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonane-4-carboxylic acid Chemical compound OC(=O)N1CCN2CCC1CC2 RUFBGPCDOFYGTF-UHFFFAOYSA-N 0.000 title 1
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 title 1
- 238000002560 therapeutic procedure Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- -1 cyano , hydroxyl Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- XJKNACDCUAFDHD-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonane Chemical compound C1CC2CCN1CCN2 XJKNACDCUAFDHD-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 description 3
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- QIQRJSMNJFPILM-UHFFFAOYSA-N (4-phenylphenyl) 1,4-diazabicyclo[3.2.2]nonane-4-carboxylate;hydrobromide Chemical compound Br.C1CN(CC2)CCC2N1C(=O)OC(C=C1)=CC=C1C1=CC=CC=C1 QIQRJSMNJFPILM-UHFFFAOYSA-N 0.000 description 2
- 101710195183 Alpha-bungarotoxin Proteins 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 201000010374 Down Syndrome Diseases 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 206010044688 Trisomy 21 Diseases 0.000 description 2
- 201000004810 Vascular dementia Diseases 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 239000012154 double-distilled water Substances 0.000 description 2
- 230000004064 dysfunction Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 230000007074 memory dysfunction Effects 0.000 description 2
- XLTANAWLDBYGFU-UHFFFAOYSA-N methyllycaconitine hydrochloride Natural products C1CC(OC)C2(C3C4OC)C5CC(C(C6)OC)C(OC)C5C6(O)C4(O)C2N(CC)CC31COC(=O)C1=CC=CC=C1N1C(=O)CC(C)C1=O XLTANAWLDBYGFU-UHFFFAOYSA-N 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000009870 specific binding Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LYTCVQQGCSNFJU-LKGYBJPKSA-N α-bungarotoxin Chemical compound C(/[C@H]1O[C@H]2C[C@H]3O[C@@H](CC(=C)C=O)C[C@H](O)[C@]3(C)O[C@@H]2C[C@@H]1O[C@@H]1C2)=C/C[C@]1(C)O[C@H]1[C@@]2(C)O[C@]2(C)CC[C@@H]3O[C@@H]4C[C@]5(C)O[C@@H]6C(C)=CC(=O)O[C@H]6C[C@H]5O[C@H]4C[C@@H](C)[C@H]3O[C@H]2C1 LYTCVQQGCSNFJU-LKGYBJPKSA-N 0.000 description 2
- IKMNJYGTSSQNSE-UHFFFAOYSA-N (4-bromophenyl) carbonochloridate Chemical compound ClC(=O)OC1=CC=C(Br)C=C1 IKMNJYGTSSQNSE-UHFFFAOYSA-N 0.000 description 1
- ISWLCQXWMQGGOZ-UHFFFAOYSA-N (4-phenylphenyl) carbonochloridate Chemical compound C1=CC(OC(=O)Cl)=CC=C1C1=CC=CC=C1 ISWLCQXWMQGGOZ-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- 208000012661 Dyskinesia Diseases 0.000 description 1
- 241000437302 Gildella Species 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 208000005314 Multi-Infarct Dementia Diseases 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 206010033664 Panic attack Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 208000027089 Parkinsonian disease Diseases 0.000 description 1
- 206010034010 Parkinsonism Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 208000000323 Tourette Syndrome Diseases 0.000 description 1
- 208000016620 Tourette disease Diseases 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 231100000867 compulsive behavior Toxicity 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 230000001146 hypoxic effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 240000004308 marijuana Species 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- IIDQANNOAINZDK-UHFFFAOYSA-N n-phenyl-1,4-diazabicyclo[3.2.2]nonane-4-carboxamide;hydrobromide Chemical compound Br.C1CN(CC2)CCC2N1C(=O)NC1=CC=CC=C1 IIDQANNOAINZDK-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- RXLOZRCLQMJJLC-UHFFFAOYSA-N ssr-180,711 Chemical compound C1=CC(Br)=CC=C1OC(=O)N1C(CC2)CCN2CC1 RXLOZRCLQMJJLC-UHFFFAOYSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000002636 symptomatic treatment Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Child & Adolescent Psychology (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Oncology (AREA)
- Heart & Thoracic Surgery (AREA)
- Communicable Diseases (AREA)
- Diabetes (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR99/03934 | 1999-03-30 | ||
| FR9903934A FR2791678B1 (fr) | 1999-03-30 | 1999-03-30 | Derives de 1,4-diazabicyclo [3.2.2] nonane-4-carboxylates et -carboxamides, leur preparation et leur application en therapeutique |
| PCT/FR2000/000697 WO2000058311A1 (fr) | 1999-03-30 | 2000-03-21 | Derives de 1,4-diazabicyclo[3.2.2]nonane-4-carboxylates et carboxamides, leur preparation et leur application en therapeutique |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002540208A JP2002540208A (ja) | 2002-11-26 |
| JP2002540208A5 JP2002540208A5 (https=) | 2006-09-14 |
| JP4500454B2 true JP4500454B2 (ja) | 2010-07-14 |
Family
ID=9543787
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000608013A Expired - Fee Related JP4500454B2 (ja) | 1999-03-30 | 2000-03-21 | １，４−ジアザビシクロ［３．２．２］ノナン−４−カルボキシレートおよびカルボキサミド誘導体、治療におけるその製造ならびに使用 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6987106B1 (https=) |
| EP (1) | EP1165559B1 (https=) |
| JP (1) | JP4500454B2 (https=) |
| AR (1) | AR023188A1 (https=) |
| AT (1) | ATE232865T1 (https=) |
| AU (1) | AU3301800A (https=) |
| CO (1) | CO5180557A1 (https=) |
| DE (1) | DE60001451T2 (https=) |
| DK (1) | DK1165559T3 (https=) |
| ES (1) | ES2192520T3 (https=) |
| FR (1) | FR2791678B1 (https=) |
| PE (1) | PE20001600A1 (https=) |
| TW (1) | TWI221843B (https=) |
| UY (1) | UY26082A1 (https=) |
| WO (1) | WO2000058311A1 (https=) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003534344A (ja) | 2000-05-25 | 2003-11-18 | ターガセプト，インコーポレイテッド | ニコチン性コリン受容体リガンドとしてのヘテロアリールジアザビシクロアルカン |
| US6624167B1 (en) | 2000-08-04 | 2003-09-23 | Targacept, Inc. | Pharmaceutical compositions and methods for use |
| DE60216830T2 (de) * | 2001-02-06 | 2007-06-14 | Pfizer Products Inc., Groton | Pharmazeutische Zusammensetzungen zur Behandlung von Störungen des ZNS oder anderen Erkrankungen |
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| SE0202465D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New compounds |
| SE0202430D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New Compounds |
| MXPA05003317A (es) | 2002-09-25 | 2005-07-05 | Memory Pharm Corp | Indazoles, benzotiazoles y benzoisotiazoles asi como preparacion y usos de los mismos. |
| MXPA05006861A (es) | 2003-02-27 | 2005-12-12 | Neurosearch As | Derivados arildiazabiciclicos novedosos. |
| DE602004010299T2 (de) | 2003-12-22 | 2008-09-18 | Memory Pharmaceuticals Corp. | Indole, 1h-indazole, 1,2-benzisoxazole und 1,2-benzisothiazole und deren herstellung und anwendungen |
| CN100445285C (zh) * | 2003-12-22 | 2008-12-24 | 阿斯利康(瑞典)有限公司 | 烟碱性乙酰胆碱受体配体 |
| TW200529860A (en) * | 2003-12-22 | 2005-09-16 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
| EP1713810B1 (en) * | 2004-02-04 | 2010-12-29 | NeuroSearch A/S | Diazabicyclic aryl derivatives as nicotinic acetylcholine receptor ligands |
| NZ550534A (en) | 2004-03-25 | 2009-07-31 | Memory Pharm Corp | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, and preparation and uses thereof |
| WO2006001894A1 (en) | 2004-04-22 | 2006-01-05 | Memory Pharmaceutical Corporation | Indoles, 1h-indazoles, 1,2-benzisoxazoles, 1,2-benzoisothiazoles, and preparation and uses thereof |
| JP2007538011A (ja) * | 2004-05-07 | 2007-12-27 | メモリー・ファーマシューティカルズ・コーポレイション | １ｈ−インダゾール、ベンゾチアゾール、１，２−ベンゾイソキサゾール、１，２−ベンゾイソチアゾール、およびクロモン、ならびにそれらの調製および使用 |
| EP1802616B1 (en) * | 2004-10-15 | 2011-01-12 | NeuroSearch A/S | Novel azabicyclic aryl derivatives and their medical use |
| RU2418797C2 (ru) | 2004-12-22 | 2011-05-20 | Мемори Фармасьютиклз Корпорейшн | Лиганды никотинового рецептора альфа-7, их получение и применение |
| US8106066B2 (en) | 2005-09-23 | 2012-01-31 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof |
| AU2007216531A1 (en) * | 2006-02-14 | 2007-08-23 | Neurosearch A/S | Novel diazabicycloalkane derivatives and their medical use |
| JP2007217370A (ja) * | 2006-02-17 | 2007-08-30 | Nard Inst Ltd | ポジトロン断層撮影法および該方法に用いるポジトロン放出化合物 |
| WO2007135120A1 (en) | 2006-05-23 | 2007-11-29 | Neurosearch A/S | Novel 1,4-diaza-bicyclo[3.2.2]nonane derivatives and their medical use |
| US20100234349A1 (en) | 2006-09-04 | 2010-09-16 | Olsen Gunnar M | Pharmaceutical combinations of a nicotine receptor modulator and a cognitive enhancer |
| WO2008119710A1 (en) * | 2007-03-30 | 2008-10-09 | Neurosearch A/S | Two-phase test method for characterizing the effect of a chemical compound on a test animal and maze for carrying out the method |
| SA08290475B1 (ar) | 2007-08-02 | 2013-06-22 | Targacept Inc | (2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه |
| FR2931823B1 (fr) | 2008-06-02 | 2012-08-17 | Sanofi Aventis | Sel de fumarate du 1,4-diazabicyclo°3.2.2!nonane-carboxylate de 4-bromophenyle, ses formes cristallines, leur preparation et leur utilisation en therapeutique |
| FR2931677B1 (fr) * | 2008-06-02 | 2010-08-20 | Sanofi Aventis | Association d'un agoniste partiel des recepteurs nicotiniques et d'un inhibiteur d'acetylcholinesterase, composition la contenant et son utilisation dans le traitement des troubles cognitifs |
| KR20180011888A (ko) | 2008-11-19 | 2018-02-02 | 포럼 파마슈티칼즈 인크. | (ｒ)-７-클로로-ｎ-(퀴누클리딘-３-일)벤조［ｂ］티오펜-２-카르복사미드 및 그 약학적으로 허용가능한 염을 이용한 인지 장애의 치료 |
| TW201031664A (en) | 2009-01-26 | 2010-09-01 | Targacept Inc | Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide |
| PE20120324A1 (es) * | 2009-05-11 | 2012-04-17 | Envivo Pharmaceuticals Inc | Combinacion que comprende (r)-7-cloro-n-(quinuclidin-3-il)benzo[b]tiofeno-2-carboxamida y donezepilo como moduladora de trastornos cognitivos |
| AR081402A1 (es) | 2010-05-17 | 2012-08-29 | Envivo Pharmaceuticals Inc | Una forma cristalina de clorhidrato de (r)-7-cloro-n-(quinuclidin-3-il) benzo(b)tiofeno-2-carboxamida monohidrato |
| AU2012231275A1 (en) | 2011-03-18 | 2013-10-17 | Genzyme Corporation | Glucosylceramide synthase inhibitors |
| CA2872005A1 (en) | 2012-05-08 | 2013-11-14 | Forum Pharmaceuticals, Inc. | Methods of maintaining, treating or improving cognitive function |
| MA37975B2 (fr) | 2012-09-11 | 2021-03-31 | Genzyme Corp | Inhibiteurs de synthase de glucosylcéramide |
| CN107188900B (zh) * | 2017-05-27 | 2019-09-06 | 北京师范大学 | α7烟碱型乙酰胆碱受体的配体化合物及其应用 |
| CN114040762A (zh) | 2019-02-04 | 2022-02-11 | 建新公司 | 使用葡糖神经酰胺合酶(gcs)的抑制剂治疗纤毛疾病 |
| TW202142236A (zh) | 2020-02-03 | 2021-11-16 | 美商健臻公司 | 用於治療與溶體儲積症相關的神經症狀之方法 |
| KR20230043024A (ko) | 2020-07-24 | 2023-03-30 | 젠자임 코포레이션 | 벤글루스타트를 포함하는 제약 조성물 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0235878A3 (en) * | 1986-01-16 | 1989-06-14 | Beecham Group Plc | Novel compounds |
| JP2668670B2 (ja) * | 1995-03-24 | 1997-10-27 | 日本たばこ産業株式会社 | ジアザビシクロ［３．３．１］ノナン誘導体、その中間体及びその医薬用途 |
| PT994875E (pt) * | 1997-06-30 | 2004-06-30 | Targacept Inc | Derivados de 3-piridil-1-aza-biciclo-alcano para a prevencao e tratamento de desordens do snc |
-
1999
- 1999-03-30 FR FR9903934A patent/FR2791678B1/fr not_active Expired - Fee Related
-
2000
- 2000-03-21 DE DE60001451T patent/DE60001451T2/de not_active Expired - Lifetime
- 2000-03-21 EP EP00911011A patent/EP1165559B1/fr not_active Expired - Lifetime
- 2000-03-21 JP JP2000608013A patent/JP4500454B2/ja not_active Expired - Fee Related
- 2000-03-21 WO PCT/FR2000/000697 patent/WO2000058311A1/fr not_active Ceased
- 2000-03-21 AU AU33018/00A patent/AU3301800A/en not_active Abandoned
- 2000-03-21 DK DK00911011T patent/DK1165559T3/da active
- 2000-03-21 US US09/937,045 patent/US6987106B1/en not_active Expired - Lifetime
- 2000-03-21 ES ES00911011T patent/ES2192520T3/es not_active Expired - Lifetime
- 2000-03-21 AT AT00911011T patent/ATE232865T1/de active
- 2000-03-28 UY UY26082A patent/UY26082A1/es not_active IP Right Cessation
- 2000-03-28 CO CO00022162A patent/CO5180557A1/es active IP Right Grant
- 2000-03-28 AR ARP000101379A patent/AR023188A1/es active IP Right Grant
- 2000-03-28 TW TW089105707A patent/TWI221843B/zh not_active IP Right Cessation
- 2000-03-30 PE PE2000000274A patent/PE20001600A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002540208A (ja) | 2002-11-26 |
| EP1165559A1 (fr) | 2002-01-02 |
| DE60001451D1 (de) | 2003-03-27 |
| FR2791678B1 (fr) | 2001-05-04 |
| DK1165559T3 (da) | 2003-06-10 |
| ES2192520T3 (es) | 2003-10-16 |
| WO2000058311A1 (fr) | 2000-10-05 |
| US6987106B1 (en) | 2006-01-17 |
| DE60001451T2 (de) | 2004-01-15 |
| EP1165559B1 (fr) | 2003-02-19 |
| PE20001600A1 (es) | 2001-04-01 |
| ATE232865T1 (de) | 2003-03-15 |
| UY26082A1 (es) | 2000-10-31 |
| AU3301800A (en) | 2000-10-16 |
| FR2791678A1 (fr) | 2000-10-06 |
| TWI221843B (en) | 2004-10-11 |
| AR023188A1 (es) | 2002-09-04 |
| CO5180557A1 (es) | 2002-07-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4500454B2 (ja) | １，４−ジアザビシクロ［３．２．２］ノナン−４−カルボキシレートおよびカルボキサミド誘導体、治療におけるその製造ならびに使用 | |
| EP1135389B1 (fr) | Derives de 1,4-diazabicyclo 3.2.2]nonane, leur preparation et leur application en therapeutique | |
| US6635645B1 (en) | 2,5,-diazabicyclo[2.2.1]heptane derivatives, their preparation and therapeutic uses | |
| US6538003B1 (en) | Pyridopyranoazepine derivatives, their preparation and their therapeutic application | |
| JP4393195B2 (ja) | ４−（１，３，４−チアジアゾール−２−イル）−１，４−ジアザビシクロ−［３．２．２］ノナン誘導体、それらの製造およびそれらの治療的使用 | |
| US7001902B2 (en) | 4-(2 phenylthiazol-5-yl)-1, 4-diazabicyclo-[3.2.2]nonane derivatives, preparation and therapeutic use thereof | |
| RS20060314A (sr) | Derivati n-heterociklilmetilbenzamida, postupak za njihovo dobijanje i njihova upotreba kao leka | |
| US20090054416A1 (en) | 1,4-Diazabicyclo[3.2.2]nonanecarboxamide Derivatives, Preparation and Therapeutic Use Thereof | |
| US6835730B2 (en) | 4-heteroparyl-1,4-diazabicyclo[3.2.2]nonane, preparation and therapeutic use thereof | |
| US20050004128A1 (en) | 4-(Oxazolopyridin-2-yl)-1,4-diazabicyclo-[3.2.2]nonane derivatives, preparation and therapeutic use thereof | |
| FR2761072A1 (fr) | Derives de 2,3-dihydrofuro[3,2-b]pyridine, leur preparation et leur application en therapeutique | |
| EP2029594A1 (en) | Novel 1,4-diaza-bicyclo[3.2.2]nonane derivatives and their medical use | |
| CA2317515A1 (en) | Oxazole derivatives as serotonin-1a receptor agonists | |
| Bertha et al. | Probes for Narcotic Receptor-Mediated Phenomena. 20. Alteration of Opioid Receptor Subtype Selectivity of the 5-(3-Hydroxyphenyl) morphans by Application of the Message-Address Concept: Preparation of. delta.-Opioid Receptor Ligands |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20060725 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20060725 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20091208 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20100406 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20100419 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130423 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130423 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140423 Year of fee payment: 4 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |