ZA200903939B - Azabicyclic compounds, a process for their preparation and pharmaceutical compositions containing them - Google Patents
Azabicyclic compounds, a process for their preparation and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- ZA200903939B ZA200903939B ZA200903939A ZA200903939A ZA200903939B ZA 200903939 B ZA200903939 B ZA 200903939B ZA 200903939 A ZA200903939 A ZA 200903939A ZA 200903939 A ZA200903939 A ZA 200903939A ZA 200903939 B ZA200903939 B ZA 200903939B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- compounds
- compound
- azabicyclo
- hex
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 85
- 238000000034 method Methods 0.000 title claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 12
- 230000008569 process Effects 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 230000015572 biosynthetic process Effects 0.000 claims description 20
- 238000003786 synthesis reaction Methods 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 230000002490 cerebral effect Effects 0.000 claims description 11
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 11
- 208000019116 sleep disease Diseases 0.000 claims description 11
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
- 206010000117 Abnormal behaviour Diseases 0.000 claims description 6
- 230000032683 aging Effects 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000543 intermediate Substances 0.000 claims description 6
- JXFDVXXBQZIJPU-OEEJBDNKSA-N 4-[3-[(1s,5r)-3-azabicyclo[3.1.0]hexan-3-yl]propoxy]benzamide;hydrochloride Chemical compound Cl.C1=CC(C(=O)N)=CC=C1OCCCN1C[C@H]2C[C@H]2C1 JXFDVXXBQZIJPU-OEEJBDNKSA-N 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 208000010877 cognitive disease Diseases 0.000 claims description 5
- 208000013403 hyperactivity Diseases 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- 208000011580 syndromic disease Diseases 0.000 claims description 5
- 206010012289 Dementia Diseases 0.000 claims description 4
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 4
- 208000019022 Mood disease Diseases 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- -1 ethylene, propylene Chemical group 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- PVQQLLNXTGAILK-OEEJBDNKSA-N 4-[3-[(1s,5r)-3-azabicyclo[3.1.0]hexan-3-yl]propoxy]benzamide;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C1=CC(C(=O)N)=CC=C1OCCCN1C[C@H]2C[C@H]2C1 PVQQLLNXTGAILK-OEEJBDNKSA-N 0.000 claims description 3
- 206010002942 Apathy Diseases 0.000 claims description 3
- 208000020401 Depressive disease Diseases 0.000 claims description 3
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 230000001149 cognitive effect Effects 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 208000014674 injury Diseases 0.000 claims description 3
- 230000033764 rhythmic process Effects 0.000 claims description 3
- 230000008733 trauma Effects 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 2
- 208000032140 Sleepiness Diseases 0.000 claims description 2
- 206010041349 Somnolence Diseases 0.000 claims description 2
- 201000004810 Vascular dementia Diseases 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 206010020765 hypersomnia Diseases 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 201000003631 narcolepsy Diseases 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 201000002859 sleep apnea Diseases 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 230000002739 subcortical effect Effects 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 208000009829 Lewy Body Disease Diseases 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- QXSAKPUBHTZHKW-UHFFFAOYSA-N 4-hydroxybenzamide Chemical compound NC(=O)C1=CC=C(O)C=C1 QXSAKPUBHTZHKW-UHFFFAOYSA-N 0.000 description 32
- 229910052757 nitrogen Inorganic materials 0.000 description 24
- 229910052799 carbon Inorganic materials 0.000 description 22
- 238000004452 microanalysis Methods 0.000 description 22
- 238000002474 experimental method Methods 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229960001340 histamine Drugs 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 230000000742 histaminergic effect Effects 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- NIDSRGCVYOEDFW-UHFFFAOYSA-N 1-bromo-4-chlorobutane Chemical compound ClCCCCBr NIDSRGCVYOEDFW-UHFFFAOYSA-N 0.000 description 3
- JZABQRRPWSWCRU-BETUJISGSA-N 4-[3-[(1s,5r)-3-azabicyclo[3.1.0]hexan-3-yl]propoxy]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OCCCN1C[C@H]2C[C@H]2C1 JZABQRRPWSWCRU-BETUJISGSA-N 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001263 acyl chlorides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- NSZUGQROUUTGGI-UHFFFAOYSA-N n-(4-hydroxyphenyl)-2-methoxyacetamide Chemical compound COCC(=O)NC1=CC=C(O)C=C1 NSZUGQROUUTGGI-UHFFFAOYSA-N 0.000 description 3
- 230000003414 procognitive effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 2
- UJCPSWBVHQROQF-UHFFFAOYSA-N 4-hydroxy-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=C(O)C=C1 UJCPSWBVHQROQF-UHFFFAOYSA-N 0.000 description 2
- VKDNYQKDAXLFIL-UHFFFAOYSA-N 4-hydroxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(O)C=C1 VKDNYQKDAXLFIL-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 102000000543 Histamine Receptors Human genes 0.000 description 2
- 108010002059 Histamine Receptors Proteins 0.000 description 2
- WLRVSRJKZYZCJY-UHFFFAOYSA-N N,N-Diethyl-4-hydroxybenzamide Chemical compound CCN(CC)C(=O)C1=CC=C(O)C=C1 WLRVSRJKZYZCJY-UHFFFAOYSA-N 0.000 description 2
- 238000011785 NMRI mouse Methods 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 230000020595 eating behavior Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 230000000926 neurological effect Effects 0.000 description 2
- 230000007171 neuropathology Effects 0.000 description 2
- 239000002858 neurotransmitter agent Substances 0.000 description 2
- 238000011017 operating method Methods 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 230000007170 pathology Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- HGWUUOXXAIISDB-SYDPRGILSA-N (1s,5r)-3-azabicyclo[3.1.0]hexane Chemical compound C1NC[C@H]2C[C@H]21 HGWUUOXXAIISDB-SYDPRGILSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- HGWUUOXXAIISDB-UHFFFAOYSA-N 3-azabicyclo[3.1.0]hexane Chemical group C1NCC2CC21 HGWUUOXXAIISDB-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- CKPWJBXTVZXVHS-UHFFFAOYSA-N 4-(3-chloropropoxy)benzamide Chemical compound NC(=O)C1=CC=C(OCCCCl)C=C1 CKPWJBXTVZXVHS-UHFFFAOYSA-N 0.000 description 1
- ONOVYJIBVIEWFM-TXEJJXNPSA-N 4-[2-[(1s,5r)-3-azabicyclo[3.1.0]hexan-3-yl]ethoxy]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OCCN1C[C@H]2C[C@H]2C1 ONOVYJIBVIEWFM-TXEJJXNPSA-N 0.000 description 1
- BKWBAOSCQKURDS-GASCZTMLSA-N 4-[3-[(1s,5r)-3-azabicyclo[3.1.0]hexan-3-yl]propoxy]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1OCCCN1C[C@H]2C[C@H]2C1 BKWBAOSCQKURDS-GASCZTMLSA-N 0.000 description 1
- PRFGCNXPSVTNCR-OEEJBDNKSA-N 4-[3-[(1s,5r)-3-azabicyclo[3.1.0]hexan-3-yl]propoxy]benzamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(C(=O)N)=CC=C1OCCCN1C[C@H]2C[C@H]2C1 PRFGCNXPSVTNCR-OEEJBDNKSA-N 0.000 description 1
- LVMDLABIFRKRLF-HDICACEKSA-N 4-[4-[(1r,5s)-3-azabicyclo[3.1.0]hexan-3-yl]butoxy]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1OCCCCN1C[C@H]2C[C@H]2C1 LVMDLABIFRKRLF-HDICACEKSA-N 0.000 description 1
- QOBVEDBJAJTAAH-GASCZTMLSA-N 4-[4-[(1r,5s)-3-azabicyclo[3.1.0]hexan-3-yl]butoxy]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1OCCCCN1C[C@H]2C[C@H]2C1 QOBVEDBJAJTAAH-GASCZTMLSA-N 0.000 description 1
- MMBVLEDCZLSTOA-OKILXGFUSA-N 4-[4-[(1s,5r)-3-azabicyclo[3.1.0]hexan-3-yl]butoxy]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OCCCCN1C[C@H]2C[C@H]2C1 MMBVLEDCZLSTOA-OKILXGFUSA-N 0.000 description 1
- CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 238000001061 Dunnett's test Methods 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- 238000005251 capillar electrophoresis Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000002903 catalepsic effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000027288 circadian rhythm Effects 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 229960002303 citric acid monohydrate Drugs 0.000 description 1
- 230000003920 cognitive function Effects 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002267 hypothalamic effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 210000004558 lewy body Anatomy 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000006386 memory function Effects 0.000 description 1
- VARIAKUPTWVWRN-OKILXGFUSA-N methyl 4-[3-[(1r,5s)-3-azabicyclo[3.1.0]hexan-3-yl]propoxy]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OCCCN1C[C@H]2C[C@H]2C1 VARIAKUPTWVWRN-OKILXGFUSA-N 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- STOAGEBURGENGQ-UHFFFAOYSA-N n-(4-hydroxyphenyl)-n-methylacetamide Chemical compound CC(=O)N(C)C1=CC=C(O)C=C1 STOAGEBURGENGQ-UHFFFAOYSA-N 0.000 description 1
- PSVGJRIRDQPVJA-BETUJISGSA-N n-[4-[2-[(1r,5s)-3-azabicyclo[3.1.0]hexan-3-yl]ethoxy]phenyl]-2-methoxyacetamide Chemical compound C1=CC(NC(=O)COC)=CC=C1OCCN1C[C@H]2C[C@H]2C1 PSVGJRIRDQPVJA-BETUJISGSA-N 0.000 description 1
- FIJTWHXWKLHFID-BETUJISGSA-N n-[4-[2-[(1s,5r)-3-azabicyclo[3.1.0]hexan-3-yl]ethoxy]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1OCCN1C[C@H]2C[C@H]2C1 FIJTWHXWKLHFID-BETUJISGSA-N 0.000 description 1
- BCORWBCZBWFMIT-KBGJBQQCSA-N n-[4-[3-[(1r,5s)-3-azabicyclo[3.1.0]hexan-3-yl]propoxy]phenyl]-n-methylacetamide;hydrochloride Chemical compound Cl.C1=CC(N(C(C)=O)C)=CC=C1OCCCN1C[C@H]2C[C@H]2C1 BCORWBCZBWFMIT-KBGJBQQCSA-N 0.000 description 1
- ZAIUTSUQJNNIHA-OKILXGFUSA-N n-[4-[3-[(1s,5r)-3-azabicyclo[3.1.0]hexan-3-yl]propoxy]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1OCCCN1C[C@H]2C[C@H]2C1 ZAIUTSUQJNNIHA-OKILXGFUSA-N 0.000 description 1
- YELGTMCTEPYQRT-FAESNJTISA-N n-[4-[4-[(1r,5s)-3-azabicyclo[3.1.0]hexan-3-yl]butoxy]phenyl]-n-methylacetamide;hydrochloride Chemical compound Cl.C1=CC(N(C(C)=O)C)=CC=C1OCCCCN1C[C@H]2C[C@H]2C1 YELGTMCTEPYQRT-FAESNJTISA-N 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 230000001962 neuropharmacologic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 238000011458 pharmacological treatment Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000036186 satiety Effects 0.000 description 1
- 235000019627 satiety Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000003956 synaptic plasticity Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000028016 temperature homeostasis Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- 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
-
- 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
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Epidemiology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0803297A FR2932479A1 (fr) | 2008-06-13 | 2008-06-13 | Nouveaux derives azabicycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200903939B true ZA200903939B (en) | 2010-04-28 |
Family
ID=40227963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200903939A ZA200903939B (en) | 2008-06-13 | 2009-06-05 | Azabicyclic compounds, a process for their preparation and pharmaceutical compositions containing them |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US7906547B2 (es) |
| EP (1) | EP2133333A1 (es) |
| JP (1) | JP2009298790A (es) |
| KR (1) | KR20090129958A (es) |
| CN (1) | CN101602706A (es) |
| AP (1) | AP2009004891A0 (es) |
| AR (1) | AR072101A1 (es) |
| AU (1) | AU2009202341A1 (es) |
| BR (1) | BRPI0902395A2 (es) |
| CA (1) | CA2668527A1 (es) |
| CL (1) | CL2009001377A1 (es) |
| CO (1) | CO6190096A1 (es) |
| CR (1) | CR10844A (es) |
| EA (1) | EA200900692A1 (es) |
| EC (1) | ECSP099396A (es) |
| FR (1) | FR2932479A1 (es) |
| GT (1) | GT200900150A (es) |
| MA (1) | MA31141B1 (es) |
| MX (1) | MX2009005891A (es) |
| MY (1) | MY144748A (es) |
| NI (1) | NI200900114A (es) |
| NZ (1) | NZ577438A (es) |
| PE (1) | PE20091961A1 (es) |
| SG (1) | SG158015A1 (es) |
| SV (1) | SV2009003292A (es) |
| TW (1) | TW201000101A (es) |
| UY (1) | UY31857A1 (es) |
| WO (1) | WO2009150331A1 (es) |
| ZA (1) | ZA200903939B (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10892398B2 (en) * | 2019-03-28 | 2021-01-12 | Johannes Pollanen | Qubit hardware for electrons on helium |
| EP4251148A1 (en) | 2020-11-27 | 2023-10-04 | Richter Gedeon Nyrt. | Histamine h3 receptor antagonists/inverse agonists for the treatment of autism spectrum disorder |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6515013B2 (en) * | 2000-07-13 | 2003-02-04 | Abbott Laboratories | 1,3-disubstituted and 1,3,3-trisubstituted pyrrolidines as histamine-3 receptor ligands and their therapeutic applications |
| US7232835B2 (en) * | 2002-12-10 | 2007-06-19 | Ranbaxy Laboratories Limited | 3,6-Disubstituted azabicyclo derivatives as muscarinic receptor antagonists |
| FR2866647B1 (fr) * | 2004-02-20 | 2006-10-27 | Servier Lab | Nouveaux derives azabicycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| EP1707203A1 (en) * | 2005-04-01 | 2006-10-04 | Bioprojet | Treatment of parkinson's disease obstructive sleep apnea, dementia with lewy bodies, vascular dementia with non-imidazole alkylamines histamine H3- receptor ligands |
| AU2006231917B2 (en) * | 2005-04-08 | 2011-07-28 | Pfizer Products Inc. | Bicyclic [3.1.0] heteroaryl amides as type I glycine transport inhibitors |
| EP1842846A1 (en) * | 2006-04-07 | 2007-10-10 | Santhera Pharmaceuticals (Schweiz) AG | Phenylpiperidine derivatives as melanocortin-4 receptor modulators |
| WO2008010238A2 (en) * | 2006-07-21 | 2008-01-24 | Lupin Limited | Antidiabetic azabicyclo [3. 1. 0] hexan compounds |
-
2008
- 2008-06-13 FR FR0803297A patent/FR2932479A1/fr not_active Withdrawn
-
2009
- 2009-05-29 UY UY031857A patent/UY31857A1/es not_active Application Discontinuation
- 2009-05-29 SG SG200903642-7A patent/SG158015A1/en unknown
- 2009-06-01 PE PE2009000758A patent/PE20091961A1/es not_active Application Discontinuation
- 2009-06-03 GT GT200900150A patent/GT200900150A/es unknown
- 2009-06-03 MY MYPI20092264A patent/MY144748A/en unknown
- 2009-06-04 MX MX2009005891A patent/MX2009005891A/es not_active Application Discontinuation
- 2009-06-04 NZ NZ577438A patent/NZ577438A/en not_active IP Right Cessation
- 2009-06-05 ZA ZA200903939A patent/ZA200903939B/en unknown
- 2009-06-08 CL CL2009001377A patent/CL2009001377A1/es unknown
- 2009-06-08 CR CR10844A patent/CR10844A/es not_active Application Discontinuation
- 2009-06-08 AP AP2009004891A patent/AP2009004891A0/xx unknown
- 2009-06-09 EC EC2009009396A patent/ECSP099396A/es unknown
- 2009-06-09 NI NI200900114A patent/NI200900114A/es unknown
- 2009-06-10 SV SV2009003292A patent/SV2009003292A/es unknown
- 2009-06-10 AU AU2009202341A patent/AU2009202341A1/en not_active Abandoned
- 2009-06-11 EA EA200900692A patent/EA200900692A1/ru unknown
- 2009-06-11 WO PCT/FR2009/000696 patent/WO2009150331A1/fr not_active Ceased
- 2009-06-11 EP EP09290432A patent/EP2133333A1/fr not_active Withdrawn
- 2009-06-11 AR ARP090102108A patent/AR072101A1/es unknown
- 2009-06-12 MA MA31986A patent/MA31141B1/fr unknown
- 2009-06-12 CA CA002668527A patent/CA2668527A1/fr not_active Abandoned
- 2009-06-12 KR KR1020090052291A patent/KR20090129958A/ko not_active Ceased
- 2009-06-12 CO CO09061577A patent/CO6190096A1/es not_active Application Discontinuation
- 2009-06-12 JP JP2009140660A patent/JP2009298790A/ja not_active Withdrawn
- 2009-06-12 US US12/456,165 patent/US7906547B2/en not_active Expired - Fee Related
- 2009-06-12 TW TW098119836A patent/TW201000101A/zh unknown
- 2009-06-15 BR BRPI0902395-0A patent/BRPI0902395A2/pt not_active Application Discontinuation
- 2009-06-15 CN CNA2009101459752A patent/CN101602706A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0902395A2 (pt) | 2010-04-20 |
| CR10844A (es) | 2009-07-23 |
| SG158015A1 (en) | 2010-01-29 |
| US7906547B2 (en) | 2011-03-15 |
| WO2009150331A1 (fr) | 2009-12-17 |
| MA31141B1 (fr) | 2010-02-01 |
| MY144748A (en) | 2011-10-31 |
| CO6190096A1 (es) | 2010-08-19 |
| NI200900114A (es) | 2010-02-03 |
| FR2932479A1 (fr) | 2009-12-18 |
| NZ577438A (en) | 2010-09-30 |
| EP2133333A1 (fr) | 2009-12-16 |
| SV2009003292A (es) | 2010-02-01 |
| EA200900692A1 (ru) | 2009-12-30 |
| AR072101A1 (es) | 2010-08-04 |
| CA2668527A1 (fr) | 2009-12-13 |
| UY31857A1 (es) | 2009-08-31 |
| CL2009001377A1 (es) | 2010-05-28 |
| TW201000101A (en) | 2010-01-01 |
| CN101602706A (zh) | 2009-12-16 |
| US20090312389A1 (en) | 2009-12-17 |
| JP2009298790A (ja) | 2009-12-24 |
| AP2009004891A0 (en) | 2009-06-30 |
| GT200900150A (es) | 2011-08-25 |
| MX2009005891A (es) | 2010-02-17 |
| KR20090129958A (ko) | 2009-12-17 |
| ECSP099396A (es) | 2010-01-29 |
| PE20091961A1 (es) | 2010-01-23 |
| AU2009202341A1 (en) | 2010-01-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7576120B2 (en) | Azabicyclic compounds, a process for their preparation and pharmaceutical compositions containing them | |
| HUE030696T2 (en) | Process for the preparation of dabigatran etexilate and its intermediates | |
| NZ542951A (en) | Azabicyclo derivatives as muscarinic receptor antagonists | |
| ZA200903939B (en) | Azabicyclic compounds, a process for their preparation and pharmaceutical compositions containing them | |
| AU2010329762B2 (en) | Azabicyclo[3.1.0]hex-2-yl derivatives, method for preparing same, and pharmaceutical compositions containing same | |
| ZA201008651B (en) | Azabicyclo[3.2.0]hept-3-yl compounds,a process for their preparation and pharmaceutical compositions containing them | |
| HK1175460A (en) | Azabicyclo[3.1.0]hex-2-yl derivatives, method for preparing same, and pharmaceutical compositions containing same | |
| HK1139679A (zh) | 新的氮杂双环化合物、它们的制备方法以及含有它们的药用组合物 | |
| MXPA06009346A (es) | Derivados azabiciclicos novedosos, metodo de preparacion de los mismos y composiciones farmaceuticas que contienen los mismos | |
| FR2953513A1 (fr) | Nouveaux derives azabicyclo[3.2.0]hept-6-yl, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
| HK1123789B (en) | Azabicyclic derivatives, preparation method thereof and pharmaceutical compositions containing same | |
| MXPA99002916A (es) | Novedosos derivados de la fenoxietilamina, su procedimiento de preparacion, su aplicacion como medicamentos y las composiciones farmaceuticas que los contienen |