ZA200300571B - Azabicyclic derivatives and their therapeutic use. - Google Patents
Azabicyclic derivatives and their therapeutic use. Download PDFInfo
- Publication number
- ZA200300571B ZA200300571B ZA200300571A ZA200300571A ZA200300571B ZA 200300571 B ZA200300571 B ZA 200300571B ZA 200300571 A ZA200300571 A ZA 200300571A ZA 200300571 A ZA200300571 A ZA 200300571A ZA 200300571 B ZA200300571 B ZA 200300571B
- Authority
- ZA
- South Africa
- Prior art keywords
- azabicyclo
- pyridyl
- ethenyl
- heptane
- substituted
- Prior art date
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- 230000001225 therapeutic effect Effects 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 158
- 238000000034 method Methods 0.000 claims description 58
- -1 5-isopropoxy-3-pyridyl Chemical group 0.000 claims description 47
- 239000008194 pharmaceutical composition Substances 0.000 claims description 41
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 19
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 10
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 230000003957 neurotransmitter release Effects 0.000 claims description 8
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 8
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 230000004075 alteration Effects 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- JVCBVWTTXCNJBJ-UHFFFAOYSA-N 1-azabicyclo[2.2.1]heptane Chemical compound C1CC2CCN1C2 JVCBVWTTXCNJBJ-UHFFFAOYSA-N 0.000 claims description 2
- WJIFNLKHNNNSAS-ARJAWSKDSA-N 3-[(z)-2-(5-propan-2-yloxypyridin-3-yl)ethenyl]-7-azabicyclo[2.2.1]heptane Chemical compound CC(C)OC1=CN=CC(\C=C/C2C3CCC(N3)C2)=C1 WJIFNLKHNNNSAS-ARJAWSKDSA-N 0.000 claims description 2
- GXAUAVKKDBHPEO-SREVYHEPSA-N 6-[(z)-2-pyridin-3-ylethenyl]-8-azabicyclo[3.2.1]octane Chemical compound C1C(N2)CCCC2C1\C=C/C1=CC=CN=C1 GXAUAVKKDBHPEO-SREVYHEPSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 6
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 4
- QAIADCZNYGEIKB-UTCJRWHESA-N 5-[(z)-2-(8-azabicyclo[3.2.1]octan-4-yl)ethenyl]-3-methyl-1,2-oxazole Chemical compound O1N=C(C)C=C1\C=C/C1C(N2)CCC2CC1 QAIADCZNYGEIKB-UTCJRWHESA-N 0.000 claims 3
- IHYPOQBYJQBRBA-SREVYHEPSA-N 5-[(z)-2-pyridin-3-ylethenyl]-9-azabicyclo[4.2.1]nonane Chemical compound C1CC2NC1CCCC2\C=C/C1=CC=CN=C1 IHYPOQBYJQBRBA-SREVYHEPSA-N 0.000 claims 3
- XGELKRWIXOPPHA-UHFFFAOYSA-N 3-(2-pyrimidin-5-ylethynyl)-7-azabicyclo[2.2.1]heptane Chemical compound C1CC2NC1CC2C#CC1=CN=CN=C1 XGELKRWIXOPPHA-UHFFFAOYSA-N 0.000 claims 2
- UYCBCYQAUKKZJT-ARJAWSKDSA-N 3-[(z)-2-(5-ethoxypyridin-3-yl)ethenyl]-7-azabicyclo[2.2.1]heptane Chemical compound CCOC1=CN=CC(\C=C/C2C3CCC(N3)C2)=C1 UYCBCYQAUKKZJT-ARJAWSKDSA-N 0.000 claims 2
- YIRGNWHLTPRRHB-IHWYPQMZSA-N 3-[(z)-2-(5-methoxypyridin-3-yl)ethenyl]-7-azabicyclo[2.2.1]heptane Chemical compound COC1=CN=CC(\C=C/C2C3CCC(N3)C2)=C1 YIRGNWHLTPRRHB-IHWYPQMZSA-N 0.000 claims 2
- QGMBFCJTCHZLKR-SREVYHEPSA-N 3-[(z)-2-(5-phenoxypyridin-3-yl)ethenyl]-7-azabicyclo[2.2.1]heptane Chemical compound C1CC2NC1CC2\C=C/C(C=1)=CN=CC=1OC1=CC=CC=C1 QGMBFCJTCHZLKR-SREVYHEPSA-N 0.000 claims 2
- AYWYTGSJAVRCSX-SREVYHEPSA-N 3-[(z)-2-(5-phenylpyridin-3-yl)ethenyl]-7-azabicyclo[2.2.1]heptane Chemical compound C1CC2NC1CC2\C=C/C(C=1)=CN=CC=1C1=CC=CC=C1 AYWYTGSJAVRCSX-SREVYHEPSA-N 0.000 claims 2
- DZQWWBMJCWSLFO-IHWYPQMZSA-N 3-[(z)-2-[5-(methoxymethyl)pyridin-3-yl]ethenyl]-7-azabicyclo[2.2.1]heptane Chemical compound COCC1=CN=CC(\C=C/C2C3CCC(N3)C2)=C1 DZQWWBMJCWSLFO-IHWYPQMZSA-N 0.000 claims 2
- PAPCFCLKJSCYAS-UHFFFAOYSA-N 5-(2-pyridin-3-ylethynyl)-9-azabicyclo[4.2.1]nonane Chemical compound C1CC2NC1CCCC2C#CC1=CC=CN=C1 PAPCFCLKJSCYAS-UHFFFAOYSA-N 0.000 claims 2
- UGWDSCQJACWEGJ-RQOWECAXSA-N 5-[(z)-2-(7-azabicyclo[2.2.1]heptan-3-yl)ethenyl]-3-methyl-1,2-oxazole Chemical compound O1N=C(C)C=C1\C=C/C1C(N2)CCC2C1 UGWDSCQJACWEGJ-RQOWECAXSA-N 0.000 claims 2
- BEWMYJUCUHUMEC-UPHRSURJSA-N 5-[(z)-2-(7-azabicyclo[2.2.1]heptan-3-yl)ethenyl]pyridin-3-ol Chemical compound OC1=CN=CC(\C=C/C2C3CCC(N3)C2)=C1 BEWMYJUCUHUMEC-UPHRSURJSA-N 0.000 claims 2
- DYFCBVWMJVPHRD-DJWKRKHSSA-N 5-[(z)-2-(8-azabicyclo[3.2.1]octan-4-yl)ethenyl]-1,2-oxazole Chemical compound C1CC2NC1CCC2\C=C/C1=CC=NO1 DYFCBVWMJVPHRD-DJWKRKHSSA-N 0.000 claims 2
- RGALJRLRGGVCCT-UHFFFAOYSA-N 3-(2-pyridin-3-ylethynyl)-7-azabicyclo[2.2.1]heptane Chemical compound C1CC2NC1CC2C#CC1=CC=CN=C1 RGALJRLRGGVCCT-UHFFFAOYSA-N 0.000 claims 1
- RPUAWEOPTFFTMD-SREVYHEPSA-N 3-[(z)-2-(5-phenylmethoxypyridin-3-yl)ethenyl]-7-azabicyclo[2.2.1]heptane Chemical compound C=1N=CC(\C=C/C2C3CCC(N3)C2)=CC=1OCC1=CC=CC=C1 RPUAWEOPTFFTMD-SREVYHEPSA-N 0.000 claims 1
- PKIWCJAXKVNQAN-ARJAWSKDSA-N 3-[(z)-2-[5-(2-methylpropoxy)pyridin-3-yl]ethenyl]-7-azabicyclo[2.2.1]heptane Chemical compound CC(C)COC1=CN=CC(\C=C/C2C3CCC(N3)C2)=C1 PKIWCJAXKVNQAN-ARJAWSKDSA-N 0.000 claims 1
- OEBWNEFQCSSENT-ARJAWSKDSA-N 3-[(z)-2-pyridin-3-ylethenyl]-7-azabicyclo[2.2.1]heptane Chemical compound C1CC2NC1CC2\C=C/C1=CC=CN=C1 OEBWNEFQCSSENT-ARJAWSKDSA-N 0.000 claims 1
- PXUIJPGLSALSGO-UPHRSURJSA-N 3-[(z)-2-pyrimidin-5-ylethenyl]-7-azabicyclo[2.2.1]heptane Chemical compound C1CC2NC1CC2\C=C/C1=CN=CN=C1 PXUIJPGLSALSGO-UPHRSURJSA-N 0.000 claims 1
- OYQIQVYLFHXUBJ-UHFFFAOYSA-N 3-[2-(5-phenoxypyridin-3-yl)ethynyl]-7-azabicyclo[2.2.1]heptane Chemical compound C1CC2NC1CC2C#CC(C=1)=CN=CC=1OC1=CC=CC=C1 OYQIQVYLFHXUBJ-UHFFFAOYSA-N 0.000 claims 1
- VEXMMCHMNXQLNG-WAYWQWQTSA-N 4-[(z)-2-(9-azabicyclo[4.2.1]nonan-5-yl)ethenyl]-3-methyl-1,2-oxazole Chemical compound CC1=NOC=C1\C=C/C1C(N2)CCC2CCC1 VEXMMCHMNXQLNG-WAYWQWQTSA-N 0.000 claims 1
- PBBDTGMHCXCJCZ-ARJAWSKDSA-N 4-[(z)-2-pyridin-3-ylethenyl]-8-azabicyclo[3.2.1]octane Chemical compound C1CC2NC1CCC2\C=C/C1=CC=CN=C1 PBBDTGMHCXCJCZ-ARJAWSKDSA-N 0.000 claims 1
- OGGMLAWMMPHDST-IWQZZHSRSA-N 5-[(z)-2-(7-azabicyclo[2.2.1]heptan-3-yl)ethenyl]-1,2-oxazole Chemical compound C1CC2NC1CC2\C=C/C1=CC=NO1 OGGMLAWMMPHDST-IWQZZHSRSA-N 0.000 claims 1
- XPNFDYBKKBHNPA-PLNGDYQASA-N 5-[(z)-2-(8-azabicyclo[3.2.1]octan-6-yl)ethenyl]-1,2-oxazole Chemical compound C1C(N2)CCCC2C1\C=C/C1=CC=NO1 XPNFDYBKKBHNPA-PLNGDYQASA-N 0.000 claims 1
- USXXTLQRQSTVAJ-WAYWQWQTSA-N 5-[(z)-2-(8-azabicyclo[3.2.1]octan-6-yl)ethenyl]-3-methyl-1,2-oxazole Chemical compound O1N=C(C)C=C1\C=C/C1C(N2)CCCC2C1 USXXTLQRQSTVAJ-WAYWQWQTSA-N 0.000 claims 1
- QGQCNDROBUEJRM-XQRVVYSFSA-N 5-[(z)-2-(9-azabicyclo[4.2.1]nonan-5-yl)ethenyl]-1,2-oxazole Chemical compound C1CC2NC1CCCC2\C=C/C1=CC=NO1 QGQCNDROBUEJRM-XQRVVYSFSA-N 0.000 claims 1
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 25
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
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- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 16
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
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- 230000015572 biosynthetic process Effects 0.000 description 9
- LHVKZKUEZYZCFS-UHFFFAOYSA-N ethyl 3-formyl-7-azabicyclo[2.2.1]heptane-7-carboxylate Chemical compound C1CC2C(C=O)CC1N2C(=O)OCC LHVKZKUEZYZCFS-UHFFFAOYSA-N 0.000 description 9
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- 229960003638 dopamine Drugs 0.000 description 8
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- YJGSEDFXRUPVCM-UHFFFAOYSA-N ethyl 6-ethynyl-8-azabicyclo[3.2.1]octane-8-carboxylate Chemical compound C1CCC2C(C#C)CC1N2C(=O)OCC YJGSEDFXRUPVCM-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
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- DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
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- 230000003993 interaction Effects 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
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- 229940049920 malate Drugs 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
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 238000007726 management method Methods 0.000 description 1
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- PYHKKEVKMOCXGT-UHFFFAOYSA-N methyl 9-(4-methylphenyl)sulfonyl-9-azabicyclo[4.2.1]non-4-ene-5-carboxylate Chemical compound COC(=O)C1=CCCC2CCC1N2S(=O)(=O)C1=CC=C(C)C=C1 PYHKKEVKMOCXGT-UHFFFAOYSA-N 0.000 description 1
- XYDYWTJEGDZLTH-UHFFFAOYSA-N methylenetriphenylphosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C)C1=CC=CC=C1 XYDYWTJEGDZLTH-UHFFFAOYSA-N 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 208000027061 mild cognitive impairment Diseases 0.000 description 1
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- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000020688 positive regulation of dopamine secretion Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- RHWSKVCZXBAWLZ-OCAPTIKFSA-N pseudopelletierine Chemical compound C1CC[C@@H]2CC(=O)C[C@H]1N2C RHWSKVCZXBAWLZ-OCAPTIKFSA-N 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000007157 ring contraction reaction Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000016978 synaptic transmission, cholinergic Effects 0.000 description 1
- 210000003568 synaptosome Anatomy 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 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
- 230000009466 transformation Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- NGEDYVJWBRCEEM-UHFFFAOYSA-N trimethyl(pyridin-2-ylmethyl)silane Chemical compound C[Si](C)(C)CC1=CC=CC=N1 NGEDYVJWBRCEEM-UHFFFAOYSA-N 0.000 description 1
- ZWTHFBGMGQDKRP-UHFFFAOYSA-N trimethyl(pyridin-3-ylmethyl)silane Chemical class C[Si](C)(C)CC1=CC=CN=C1 ZWTHFBGMGQDKRP-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
-
- 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
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- 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
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- 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
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Virology (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/633,156 US6624167B1 (en) | 2000-08-04 | 2000-08-04 | Pharmaceutical compositions and methods for use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200300571B true ZA200300571B (en) | 2004-04-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200300571A ZA200300571B (en) | 2000-08-04 | 2003-01-21 | Azabicyclic derivatives and their therapeutic use. |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US6624167B1 (no) |
| EP (1) | EP1305316A2 (no) |
| JP (1) | JP2004536019A (no) |
| CN (1) | CN1447811A (no) |
| AU (1) | AU2001276911A1 (no) |
| BR (1) | BR0113033A (no) |
| CA (1) | CA2417967A1 (no) |
| HU (1) | HUP0401225A3 (no) |
| IL (1) | IL153897A0 (no) |
| NO (1) | NO20030547L (no) |
| NZ (1) | NZ523728A (no) |
| PL (1) | PL363048A1 (no) |
| WO (1) | WO2002012245A2 (no) |
| ZA (1) | ZA200300571B (no) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2005524712A (ja) * | 2002-05-07 | 2005-08-18 | ニューロサーチ、アクティーゼルスカブ | 新規アザシクロエチニル誘導体 |
| AU2002313690A1 (en) * | 2002-07-19 | 2004-02-09 | Targacept, Inc. | Five-membered heteroaromatic olefinic azacyclic compounds, pharmaceutical compositions containing them and their use as inhibitors of ncotinic cholinergic receptors |
| US7098331B2 (en) | 2003-03-05 | 2006-08-29 | Targacept, Inc. | Arylvinylazacycloalkane compounds and methods of preparation and use thereof |
| US7235688B1 (en) | 2004-11-04 | 2007-06-26 | University Of Notre Dame Du Lac | Process for preparing histone deacetylase inhibitors and intermediates thereof |
| US20070021612A1 (en) * | 2004-11-04 | 2007-01-25 | University Of Notre Dame Du Lac | Processes and compounds for preparing histone deacetylase inhibitors and intermediates thereof |
| PE20061162A1 (es) * | 2004-12-06 | 2006-10-14 | Smithkline Beecham Corp | Compuestos derivados olefinicos de 8-azoniabiciclo[3.2.1]octanos |
| US20090239901A1 (en) * | 2008-03-19 | 2009-09-24 | Merouane Bencherif | Method and compositions for treatment of cerebral malaria |
| 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 |
| EP2509982A1 (en) | 2009-12-07 | 2012-10-17 | Targacept, Inc. | 3,6-diazabicyclo[3.1.1]heptanes as neuronal nicotinic acetylcholine receptor ligands |
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| US5817679A (en) | 1993-04-01 | 1998-10-06 | University Of Virginia | 7-Azabicyclo 2.2.1!-heptane and -heptene derivatives as cholinergic receptor ligands |
| US6060473A (en) | 1993-04-01 | 2000-05-09 | Ucb S.A. - Dtb | 7-azabicyclo[2.2.1]-heptane and -heptene derivatives as cholinergic receptor ligands |
| US5852041A (en) | 1993-04-07 | 1998-12-22 | Sibia Neurosciences, Inc. | Substituted pyridines useful as modulators of acethylcholine receptors |
| JP3637973B2 (ja) | 1993-06-17 | 2005-04-13 | エーザイ株式会社 | アザビシクロヘプタン誘導体 |
| US5510355A (en) | 1994-09-06 | 1996-04-23 | Bencherif; Merouane | Depolarizing skeletal muscle relaxants |
| US5583140A (en) | 1995-05-17 | 1996-12-10 | Bencherif; Merouane | Pharmaceutical compositions for the treatment of central nervous system disorders |
| EP0842172A1 (en) | 1995-06-29 | 1998-05-20 | Novo Nordisk A/S | Novel substituted azacyclic or azabicyclic compounds |
| EP0853621A1 (en) | 1995-09-22 | 1998-07-22 | Novo Nordisk A/S | Novel substituted azacyclic or azabicyclic compounds |
| IL123583A (en) | 1995-10-13 | 2003-07-31 | Neurosearch As | 3-substituted -8-azabicyclo [3,2,1] oct-2-ene derivatives, their preparation and pharmaceutical compositions containing them |
| AU736798B2 (en) | 1997-05-30 | 2001-08-02 | Neurosearch A/S | 9-Azabicyclo(3.3.1)non-2-ene and nonane derivatives as cholinergic ligands at nicotinic ACh receptors |
| US5952339A (en) | 1998-04-02 | 1999-09-14 | Bencherif; Merouane | Pharmaceutical compositions and methods of using nicotinic antagonists for treating a condition or disorder characterized by alteration in normal neurotransmitter release |
| JP4676062B2 (ja) | 1999-01-29 | 2011-04-27 | アボット・ラボラトリーズ | ニコチン性アセチルコリン受容体リガンドとしてのジアザ２環式誘導体 |
| FR2791678B1 (fr) | 1999-03-30 | 2001-05-04 | Synthelabo | Derives de 1,4-diazabicyclo [3.2.2] nonane-4-carboxylates et -carboxamides, leur preparation et leur application en therapeutique |
| JP2003513054A (ja) | 1999-11-01 | 2003-04-08 | ターガセプト，インコーポレイテッド | アリールオレフィンアザ環式化合物及びアリールアセチレンアザ環式化合物、それらを含有する薬剤組成物、及び、ニコチンコリン作動性受容体の阻害薬としてのそれらの使用 |
| GB0000257D0 (en) | 2000-01-07 | 2000-03-01 | Univ Bristol | 9-Azabicyclo[4.2.1]non-2-ene derivatives as ligands for nicotinic acetylcholine receptors |
-
2000
- 2000-08-04 US US09/633,156 patent/US6624167B1/en not_active Expired - Fee Related
-
2001
- 2001-07-13 WO PCT/US2001/022170 patent/WO2002012245A2/en active IP Right Grant
- 2001-07-13 CN CN01813738A patent/CN1447811A/zh active Pending
- 2001-07-13 NZ NZ523728A patent/NZ523728A/en unknown
- 2001-07-13 EP EP01954684A patent/EP1305316A2/en not_active Ceased
- 2001-07-13 HU HU0401225A patent/HUP0401225A3/hu unknown
- 2001-07-13 PL PL01363048A patent/PL363048A1/xx not_active Application Discontinuation
- 2001-07-13 JP JP2002518220A patent/JP2004536019A/ja not_active Withdrawn
- 2001-07-13 CA CA002417967A patent/CA2417967A1/en not_active Abandoned
- 2001-07-13 IL IL15389701A patent/IL153897A0/xx unknown
- 2001-07-13 BR BR0113033-1A patent/BR0113033A/pt not_active IP Right Cessation
- 2001-07-13 AU AU2001276911A patent/AU2001276911A1/en not_active Abandoned
-
2003
- 2003-01-21 ZA ZA200300571A patent/ZA200300571B/en unknown
- 2003-02-04 NO NO20030547A patent/NO20030547L/no unknown
- 2003-09-23 US US10/668,692 patent/US7022706B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| PL363048A1 (en) | 2004-11-15 |
| WO2002012245B1 (en) | 2003-03-20 |
| WO2002012245A3 (en) | 2002-06-13 |
| NO20030547D0 (no) | 2003-02-04 |
| AU2001276911A1 (en) | 2002-02-18 |
| CA2417967A1 (en) | 2002-02-14 |
| US20040152723A1 (en) | 2004-08-05 |
| HUP0401225A3 (en) | 2005-07-28 |
| IL153897A0 (en) | 2003-07-31 |
| JP2004536019A (ja) | 2004-12-02 |
| HUP0401225A2 (hu) | 2004-12-28 |
| NO20030547L (no) | 2003-02-04 |
| BR0113033A (pt) | 2003-07-15 |
| EP1305316A2 (en) | 2003-05-02 |
| WO2002012245A2 (en) | 2002-02-14 |
| NZ523728A (en) | 2004-09-24 |
| US7022706B2 (en) | 2006-04-04 |
| US6624167B1 (en) | 2003-09-23 |
| CN1447811A (zh) | 2003-10-08 |
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