ZA200208969B - Azabicyclic carbamates and their use as alpha-7 nicotinic acetylcholine receptor agonists. - Google Patents
Azabicyclic carbamates and their use as alpha-7 nicotinic acetylcholine receptor agonists. Download PDFInfo
- Publication number
- ZA200208969B ZA200208969B ZA200208969A ZA200208969A ZA200208969B ZA 200208969 B ZA200208969 B ZA 200208969B ZA 200208969 A ZA200208969 A ZA 200208969A ZA 200208969 A ZA200208969 A ZA 200208969A ZA 200208969 B ZA200208969 B ZA 200208969B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- formula
- free base
- acid addition
- addition salt
- Prior art date
Links
- 150000004657 carbamic acid derivatives Chemical class 0.000 title description 2
- 239000000018 receptor agonist Substances 0.000 title description 2
- 229940044601 receptor agonist Drugs 0.000 title description 2
- 102000047725 alpha7 Nicotinic Acetylcholine Receptor Human genes 0.000 title 1
- 108700006085 alpha7 Nicotinic Acetylcholine Receptor Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 150000003839 salts Chemical group 0.000 claims description 19
- 230000003287 optical effect Effects 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 239000012458 free base Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 9
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 8
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 208000028017 Psychotic disease Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- FZCCWBIUMZOAMX-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-ylcarbamic acid Chemical compound C1CC2C(NC(=O)O)CN1CC2 FZCCWBIUMZOAMX-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- HQYLURGLNKLOQJ-UHFFFAOYSA-N 1-(2-fluorophenyl)ethyl n-(1-azabicyclo[2.2.2]octan-3-yl)carbamate Chemical compound C1N(CC2)CCC2C1NC(=O)OC(C)C1=CC=CC=C1F HQYLURGLNKLOQJ-UHFFFAOYSA-N 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 description 10
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229940093499 ethyl acetate Drugs 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 238000002825 functional assay Methods 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000000574 ganglionic effect Effects 0.000 description 3
- 210000003205 muscle Anatomy 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
- -1 (1-Aza-bicyclo[2.2.2]oct-3-yl)-carbamic acid benzyl ester 3-Aminoquinuclidine dihydrochloride Chemical compound 0.000 description 2
- IXLVUUFUDRJUSL-RPBOFIJWSA-N 5-[[4-(3-acetamidophenyl)phenyl]methyl]-n-[(1s,2r)-2-phenylcyclopropyl]-1,3-oxazole-4-carboxamide Chemical compound CC(=O)NC1=CC=CC(C=2C=CC(CC3=C(N=CO3)C(=O)N[C@@H]3[C@H](C3)C=3C=CC=CC=3)=CC=2)=C1 IXLVUUFUDRJUSL-RPBOFIJWSA-N 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 210000002919 epithelial cell Anatomy 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 201000000980 schizophrenia Diseases 0.000 description 2
- 230000009151 sensory gating Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- KPOHRPVCSODGKS-UHFFFAOYSA-N (3,4,5-trimethoxyphenyl)methyl n-(1-azabicyclo[2.2.2]octan-3-yl)carbamate Chemical compound COC1=C(OC)C(OC)=CC(COC(=O)NC2C3CCN(CC3)C2)=C1 KPOHRPVCSODGKS-UHFFFAOYSA-N 0.000 description 1
- STZHBULOYDCZET-KLXURFKVSA-N (3r)-1-azabicyclo[2.2.2]octan-3-amine;dihydrochloride Chemical compound Cl.Cl.C1CC2[C@@H](N)CN1CC2 STZHBULOYDCZET-KLXURFKVSA-N 0.000 description 1
- STZHBULOYDCZET-XCUBXKJBSA-N (3s)-1-azabicyclo[2.2.2]octan-3-amine;dihydrochloride Chemical compound Cl.Cl.C1CC2[C@H](N)CN1CC2 STZHBULOYDCZET-XCUBXKJBSA-N 0.000 description 1
- CIDZDYAPPNMBIY-UHFFFAOYSA-N (4-butylphenyl)methanol Chemical compound CCCCC1=CC=C(CO)C=C1 CIDZDYAPPNMBIY-UHFFFAOYSA-N 0.000 description 1
- WCZNPSJKYCMGRO-UHFFFAOYSA-N 1,3-benzodioxol-5-ylmethyl n-(1-azabicyclo[2.2.2]octan-3-yl)carbamate Chemical compound C1=C2OCOC2=CC(COC(NC2C3CCN(CC3)C2)=O)=C1 WCZNPSJKYCMGRO-UHFFFAOYSA-N 0.000 description 1
- WORJRXHJTUTINR-UHFFFAOYSA-N 1,4-dioxane;hydron;chloride Chemical compound Cl.C1COCCO1 WORJRXHJTUTINR-UHFFFAOYSA-N 0.000 description 1
- REUAXQZIRFXQML-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-amine Chemical compound C1CC2C(N)CN1CC2 REUAXQZIRFXQML-UHFFFAOYSA-N 0.000 description 1
- STZHBULOYDCZET-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-amine;hydron;dichloride Chemical compound Cl.Cl.C1CC2C(N)CN1CC2 STZHBULOYDCZET-UHFFFAOYSA-N 0.000 description 1
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- RNUUYOMGXOSIDK-UHFFFAOYSA-N 1-phenylethyl imidazole-1-carboxylate Chemical compound C=1C=CC=CC=1C(C)OC(=O)N1C=CN=C1 RNUUYOMGXOSIDK-UHFFFAOYSA-N 0.000 description 1
- JHEJZTPMJZMAKF-UHFFFAOYSA-N 1-phenylethyl n-(1-azabicyclo[2.2.2]octan-3-yl)carbamate Chemical compound C1N(CC2)CCC2C1NC(=O)OC(C)C1=CC=CC=C1 JHEJZTPMJZMAKF-UHFFFAOYSA-N 0.000 description 1
- OKRROXQXGNEUSS-UHFFFAOYSA-N 1h-imidazol-1-ium-1-carboxylate Chemical compound OC(=O)N1C=CN=C1 OKRROXQXGNEUSS-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000011765 DBA/2 mouse Methods 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010026749 Mania Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- JNGWCDIGPQJSFI-CQSZACIVSA-N benzyl n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]carbamate Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)OCC1=CC=CC=C1 JNGWCDIGPQJSFI-CQSZACIVSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000009460 calcium influx Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000001817 pituitary effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0010955.3A GB0010955D0 (en) | 2000-05-05 | 2000-05-05 | Organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200208969B true ZA200208969B (en) | 2003-10-07 |
Family
ID=9891092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200208969A ZA200208969B (en) | 2000-05-05 | 2002-11-05 | Azabicyclic carbamates and their use as alpha-7 nicotinic acetylcholine receptor agonists. |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US6780861B2 (ko) |
| EP (1) | EP1282620B1 (ko) |
| JP (1) | JP4898062B2 (ko) |
| KR (1) | KR20020093974A (ko) |
| CN (1) | CN1167703C (ko) |
| AR (1) | AR028073A1 (ko) |
| AT (1) | ATE263167T1 (ko) |
| AU (2) | AU2001262257B2 (ko) |
| BR (1) | BR0110521A (ko) |
| CA (1) | CA2407972C (ko) |
| CZ (1) | CZ20023622A3 (ko) |
| DE (1) | DE60102581T2 (ko) |
| DK (1) | DK1282620T3 (ko) |
| ES (1) | ES2218418T3 (ko) |
| GB (1) | GB0010955D0 (ko) |
| HK (1) | HK1054223B (ko) |
| HU (1) | HUP0301866A2 (ko) |
| IL (1) | IL152417A0 (ko) |
| MX (1) | MXPA02010892A (ko) |
| NO (1) | NO20025280D0 (ko) |
| NZ (1) | NZ522226A (ko) |
| PE (1) | PE20020221A1 (ko) |
| PL (1) | PL357435A1 (ko) |
| PT (1) | PT1282620E (ko) |
| RU (1) | RU2002131886A (ko) |
| SK (1) | SK15612002A3 (ko) |
| TR (1) | TR200401007T4 (ko) |
| WO (1) | WO2001085727A1 (ko) |
| ZA (1) | ZA200208969B (ko) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6262265A (ja) * | 1985-09-13 | 1987-03-18 | Hitachi Ltd | 復水器自動検査補修システム |
| US6953855B2 (en) | 1998-12-11 | 2005-10-11 | Targacept, Inc. | 3-substituted-2(arylalkyl)-1-azabicycloalkanes and methods of use thereof |
| PE20021019A1 (es) * | 2001-04-19 | 2002-11-13 | Upjohn Co | Grupos azabiciclicos sustituidos |
| US6740663B2 (en) * | 2001-11-02 | 2004-05-25 | G.D. Searle, Llc | Mono- and di-fluorinated benzothiepine compounds as inhibitors of apical sodium co-dependent bile acid transport (ASBT) and taurocholate uptake |
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| CA2476417A1 (en) * | 2002-02-15 | 2003-08-28 | Pharmacia & Upjohn Company | Azabicyclo-substituted benzoylamides and thioamides for treatment of cns-related disorders |
| MXPA04008152A (es) * | 2002-02-19 | 2005-09-08 | Upjohn Co | Compuestos azabiciclicos para el tratamiento de enfermedades. |
| DE10234424A1 (de) | 2002-07-29 | 2004-02-12 | Bayer Ag | Benzothiophen-, Benzofuran- und Indolharnstoffe |
| GB0220581D0 (en) | 2002-09-04 | 2002-10-09 | Novartis Ag | Organic Compound |
| RU2391341C2 (ru) * | 2002-09-25 | 2010-06-10 | Мемори Фармасьютиклз Корпорейшн | Индазолы, бензотиазолы, бензоизотиазолы, их получение и применение |
| EP1949901B1 (en) | 2002-12-06 | 2014-02-12 | The Feinstein Institute for Medical Research | A method for determining a cholinergic agonist selective for an alpha 7 nicotinic receptor |
| US7238715B2 (en) | 2002-12-06 | 2007-07-03 | The Feinstein Institute For Medical Research | Treatment of pancreatitis using alpha 7 receptor-binding cholinergic agonists |
| JP2006521345A (ja) * | 2003-03-28 | 2006-09-21 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | ニコチン性アセチルコリン受容体の正のアロステリック調節剤 |
| DK1697378T3 (da) | 2003-12-22 | 2008-03-17 | Memory Pharm Corp | Indoler, 1H-indazoler, 1,2-benzisoxazoler og 1,2-benzisothiazoler og fremstilling og anvendelser deraf |
| US20050170360A1 (en) * | 2004-01-30 | 2005-08-04 | Papke Roger L. | Variant neuronal nicotinic alpha-7 receptor and methods of use |
| EP1713809B1 (en) * | 2004-02-04 | 2009-07-29 | Neurosearch A/S | Dimeric azacyclic compounds and their use |
| CN103724343A (zh) * | 2004-03-25 | 2014-04-16 | 记忆药物公司 | 吲唑、苯并噻唑、苯并异噻唑、苯并异噁唑及其制备和用途 |
| EP1742944B1 (en) * | 2004-04-22 | 2010-11-10 | Memory Pharmaceuticals Corporation | Indoles, 1h-indazoles, 1,2-benzisoxazoles, 1,2-benzoisothiazoles, and preparation and uses thereof |
| US7632831B2 (en) * | 2004-05-07 | 2009-12-15 | Memory Pharmaceuticals Corporation | 1H-indazoles, benzothiazoles, 1,2-benzoisoxazoles, 1,2-benzoisothiazoles, and chromones and preparation and uses thereof |
| PE20060437A1 (es) | 2004-06-18 | 2006-06-08 | Novartis Ag | COMPUESTOS AZA-BICICLONONANOS COMO LIGANDOS COLINERGICOS DE nAChR |
| GB0415746D0 (en) | 2004-07-14 | 2004-08-18 | Novartis Ag | Organic compounds |
| GB0424564D0 (en) | 2004-11-05 | 2004-12-08 | Novartis Ag | Organic compounds |
| CA2591817A1 (en) | 2004-12-22 | 2006-06-29 | Memory Pharmaceuticals Corporation | Nicotinic alpha-7 receptor ligands and preparation and uses thereof |
| US8106066B2 (en) | 2005-09-23 | 2012-01-31 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof |
| GB0521508D0 (en) | 2005-10-21 | 2005-11-30 | Novartis Ag | Organic compounds |
| US8316104B2 (en) | 2005-11-15 | 2012-11-20 | California Institute Of Technology | Method and apparatus for collaborative system |
| GB0525673D0 (en) | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
| GB0525672D0 (en) | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
| 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 |
| PE20110711A1 (es) | 2008-11-19 | 2011-10-11 | Envivo Pharmaceuticals Inc | Tratamiento de trastornos cognitivos con (r)-7-cloro-n-(quinuclidin-3-il)benzo[b]tiofeno-2-carboxamida y sales farmaceuticamente aceptables de la misma |
| 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 |
| RU2011150248A (ru) * | 2009-05-11 | 2013-06-20 | Энвиво Фармасьютикалз, Инк. | Лечение когнитивных расстройств с определенными рецепторами альфа-7 никотиновой кислоты в комбинации с ингибиторами ацетилхолинэстеразы |
| EP2456438A2 (en) * | 2009-07-23 | 2012-05-30 | Novartis AG | Use of azabicycloalkyl derivatives or pyrrolidine-2-one derivatives |
| TWI558398B (zh) | 2009-09-22 | 2016-11-21 | 諾華公司 | 菸鹼乙醯膽鹼受體α７活化劑之用途 |
| JP5633405B2 (ja) * | 2010-02-18 | 2014-12-03 | Jsr株式会社 | 新規化合物、感放射線性組成物及び硬化膜 |
| CN102823159A (zh) * | 2010-03-26 | 2012-12-12 | 康宁股份有限公司 | 低非线性长距离光传输系统 |
| CA2989633A1 (en) | 2010-05-17 | 2011-11-24 | Forum Pharmaceuticals Inc. | A crystalline form of (r)-7-chloro-n-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride monohydrate |
| RU2013108223A (ru) | 2010-07-26 | 2014-09-10 | Энвиво Фармасьютикалз, Инк. | Лечение когнитивных нарушений определенными агонистами рецептора никотиновой кислоты альфа-7 в сочетании с ингибиторами ацетилхолинэстеразы |
| MX2013008704A (es) * | 2011-01-27 | 2013-08-21 | Novartis Ag | Uso de activadores del receptor de acetil-colina nicotinico alfa-7. |
| EA201391348A8 (ru) * | 2011-03-18 | 2014-11-28 | Новартис Аг | КОМБИНАЦИИ АКТИВАТОРОВ АЛЬФА-7 НИКОТИНОВОГО АЦЕТИЛХОЛИНОВОГО РЕЦЕПТОРА И АНТАГОНИСТОВ mGluR5, ПРЕДНАЗНАЧЕННЫЕ ДЛЯ ПРИМЕНЕНИЯ ПРИ ВЫЗВАННОЙ ДОПАМИНОМ ДИСКИНЕЗИИ, СВЯЗАННОЙ С БОЛЕЗНЬЮ ПАРКИНСОНА |
| EP2685986B1 (en) * | 2011-03-18 | 2019-11-27 | Genzyme Corporation | Glucosylceramide synthase inhibitor |
| EP2702041A1 (en) | 2011-04-29 | 2014-03-05 | Chiesi Farmaceutici S.p.A. | Alkaloid ester and carbamate derivatives and medicinal compositions thereof |
| CA3083244C (en) * | 2011-10-20 | 2023-01-03 | Novartis Ag | Biomarkers predictive of responsiveness to alpha 7 nicotinic acetylcholine receptor activator treatment |
| 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 |
| BR112015013771B1 (pt) | 2012-12-11 | 2022-10-04 | Novartis Ag | Composição que compreende um ativador do receptor alfa 7, nicotínico de acetilcolina (nachr) como biomarcador preditivo de resposta ao tratamento de ativador do dito receptor |
| CN105263495B (zh) | 2013-01-15 | 2019-05-14 | 诺华有限公司 | α7烟碱型乙酰胆碱受体激动剂的应用 |
| US20150313884A1 (en) | 2013-01-15 | 2015-11-05 | Novartis Ag | Use of alpha 7 nicotinic acetylcholine receptor agonists |
| BR112015016992A8 (pt) | 2013-01-15 | 2018-01-23 | Novartis Ag | uso de agonistas do receptor alfa 7 nicotínico de acetilcolina |
| CN105263492B (zh) * | 2013-01-15 | 2018-04-10 | 诺华有限公司 | α7烟碱型乙酰胆碱受体激动剂在治疗发作性睡病中的应用 |
| US9724340B2 (en) | 2015-07-31 | 2017-08-08 | Attenua, Inc. | Antitussive compositions and methods |
| CA3186766A1 (en) | 2020-07-24 | 2022-01-27 | Danielle Combessis | Pharmaceutical compositions comprising venglustat |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL99537A (en) | 1990-09-27 | 1995-11-27 | Merck & Co Inc | Fibrinogen receptor antagonists and pharmaceutical preparations containing them |
| AU7545894A (en) * | 1993-09-02 | 1995-03-22 | Yamanouchi Pharmaceutical Co., Ltd. | Carbamate derivative and medicine containing the same |
| ZA957746B (en) | 1994-09-14 | 1996-07-25 | Lundbeck & Co As H | Carbamoyloxy amine compounds |
| GB9525261D0 (en) | 1995-12-11 | 1996-02-07 | Bayer Ag | Carbamic acid derivatives |
| GB9526560D0 (en) * | 1995-12-27 | 1996-02-28 | Bayer Ag | Use of 2-Amino-Heterocycles |
| SE9600683D0 (sv) | 1996-02-23 | 1996-02-23 | Astra Ab | Azabicyclic esters of carbamic acids useful in therapy |
| WO1997046557A1 (en) * | 1996-06-05 | 1997-12-11 | Wolfgang Lindner | Cinchonan based chiral selectors for separation of stereoisomers |
| US6624173B1 (en) * | 1997-06-30 | 2003-09-23 | Targacept, Inc. | Pharmaceutical compositions for treating and/or preventing CNS disorders |
| US6525065B1 (en) * | 1997-06-30 | 2003-02-25 | Targacept, Inc. | Pharmaceutical compositions and methods for effecting dopamine release |
| US5988429A (en) * | 1997-10-14 | 1999-11-23 | Pharmadesign, Inc. | Blister pack pill dispenser |
| ATE312100T1 (de) * | 1999-09-28 | 2005-12-15 | Eisai Co Ltd | Chinuclidin-verbindungen und medikamente die diese als aktive wirkstoffe enthalten |
| WO2002016358A2 (en) * | 2000-08-18 | 2002-02-28 | Pharmacia & Upjohn Company | Quinuclidine-substituted aryl moieties for treatment of disease (nicotinic acetylcholine receptor ligands) |
| GB0109871D0 (en) * | 2001-04-20 | 2001-06-13 | Glaxo Group Ltd | Metering method for particulate material |
-
2000
- 2000-05-05 GB GBGB0010955.3A patent/GB0010955D0/en not_active Ceased
-
2001
- 2001-05-03 US US10/258,920 patent/US6780861B2/en not_active Expired - Fee Related
- 2001-05-03 SK SK1561-2002A patent/SK15612002A3/sk unknown
- 2001-05-03 KR KR1020027014760A patent/KR20020093974A/ko not_active Application Discontinuation
- 2001-05-03 AR ARP010102089A patent/AR028073A1/es not_active Application Discontinuation
- 2001-05-03 CA CA002407972A patent/CA2407972C/en not_active Expired - Fee Related
- 2001-05-03 MX MXPA02010892A patent/MXPA02010892A/es unknown
- 2001-05-03 RU RU2002131886/04A patent/RU2002131886A/ru not_active Application Discontinuation
- 2001-05-03 AU AU2001262257A patent/AU2001262257B2/en not_active Ceased
- 2001-05-03 HU HU0301866A patent/HUP0301866A2/hu unknown
- 2001-05-03 AT AT01936319T patent/ATE263167T1/de active
- 2001-05-03 AU AU6225701A patent/AU6225701A/xx active Pending
- 2001-05-03 JP JP2001582328A patent/JP4898062B2/ja not_active Expired - Fee Related
- 2001-05-03 IL IL15241701A patent/IL152417A0/xx unknown
- 2001-05-03 EP EP01936319A patent/EP1282620B1/en not_active Expired - Lifetime
- 2001-05-03 TR TR2004/01007T patent/TR200401007T4/xx unknown
- 2001-05-03 PE PE2001000399A patent/PE20020221A1/es not_active Application Discontinuation
- 2001-05-03 DK DK01936319T patent/DK1282620T3/da active
- 2001-05-03 WO PCT/EP2001/005008 patent/WO2001085727A1/en not_active Application Discontinuation
- 2001-05-03 PL PL01357435A patent/PL357435A1/xx not_active Application Discontinuation
- 2001-05-03 CZ CZ20023622A patent/CZ20023622A3/cs unknown
- 2001-05-03 PT PT01936319T patent/PT1282620E/pt unknown
- 2001-05-03 DE DE60102581T patent/DE60102581T2/de not_active Expired - Lifetime
- 2001-05-03 ES ES01936319T patent/ES2218418T3/es not_active Expired - Lifetime
- 2001-05-03 NZ NZ522226A patent/NZ522226A/en unknown
- 2001-05-03 BR BR0110521-3A patent/BR0110521A/pt not_active Application Discontinuation
- 2001-05-03 CN CNB01808821XA patent/CN1167703C/zh not_active Expired - Fee Related
-
2002
- 2002-11-04 NO NO20025280A patent/NO20025280D0/no not_active Application Discontinuation
- 2002-11-05 ZA ZA200208969A patent/ZA200208969B/en unknown
-
2003
- 2003-07-07 HK HK03104830.3A patent/HK1054223B/zh not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2407972C (en) | Azabicyclic carbamates and their use as alpha-7 nicotinic acetylcholine receptor agonists | |
| AU2001262257A1 (en) | Azabicyclic carbamates and their use as alpha-7 nicotinic acetylcholine receptor agonists | |
| JP5124714B2 (ja) | アザビシクロアルキルエーテルおよびそのα７−ＮＡＣＨＲアゴニストとしての使用 | |
| US7737280B2 (en) | Processes for preparing palonosetron salts | |
| US7271168B2 (en) | Piperazine derivatives having SST1 antagonistic activity | |
| RU2162470C2 (ru) | 2,7-замещенные производные октагидропирроло[1,2-а]пиразина, способ лечения, фармацевтическая композиция, промежуточные соединения | |
| JPH02138266A (ja) | ６‐フェニル‐３‐（ピペラジニルアルキル）‐２，４（１ｈ，３ｈ）‐ピリミジンジオン誘導体 | |
| JPH10504820A (ja) | Ｎ−置換されたフェノチアジン類の使用 | |
| EP1440075B1 (fr) | Nouveaux derives amides heteroaromatiques de 3beta-amino azabicyclooctane, leur procede de preparation et leurs applications en therapeutique | |
| IE883136L (en) | Ó(2)-adreno receptor antagonists | |
| US7683075B2 (en) | Isoquinoline-3-carboxylic acid amides and pharmaceutical uses thereof | |
| NZ233002A (en) | 3-(aminoalkyl)benzothiopyran derivatives and pharmaceutical compositions | |
| US6391870B2 (en) | Pyrrolo [2,1-b][1,3]benzothiazepines with atypical antipsychotic activity | |
| CZ280931B6 (cs) | Opticky aktivní karboxamidové deriváty, farmaceutický prostředek s analgetickým účinkem a prostředek s agonistickým účinkem vzhledem ke k-receptorům |