AU2003248592B2 - Biaryl diazabicycloalkane amides as nicotinic acetylcholine agonists - Google Patents
Biaryl diazabicycloalkane amides as nicotinic acetylcholine agonists Download PDFInfo
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- AU2003248592B2 AU2003248592B2 AU2003248592A AU2003248592A AU2003248592B2 AU 2003248592 B2 AU2003248592 B2 AU 2003248592B2 AU 2003248592 A AU2003248592 A AU 2003248592A AU 2003248592 A AU2003248592 A AU 2003248592A AU 2003248592 B2 AU2003248592 B2 AU 2003248592B2
- Authority
- AU
- Australia
- Prior art keywords
- methanone
- diazabicyclo
- furan
- thiophen
- oxygen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000001408 amides Chemical class 0.000 title description 14
- 125000005841 biaryl group Chemical group 0.000 title 1
- 239000000064 cholinergic agonist Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 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 abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 182
- -1 1 ,4-diazabicyclo[3 .2,2]non-4-yl Chemical group 0.000 claims description 107
- 229910052760 oxygen Inorganic materials 0.000 claims description 65
- 239000002904 solvent Substances 0.000 claims description 64
- 239000001301 oxygen Substances 0.000 claims description 63
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 62
- 229910052717 sulfur Inorganic materials 0.000 claims description 46
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 44
- 239000011593 sulfur Substances 0.000 claims description 44
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 150000002367 halogens Chemical class 0.000 claims description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 35
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 34
- 239000003054 catalyst Substances 0.000 claims description 33
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 30
- 125000005842 heteroatom Chemical group 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 125000002524 organometallic group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims description 17
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 17
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 230000006735 deficit Effects 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
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- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
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- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 230000003935 attention Effects 0.000 claims description 4
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- 239000000460 chlorine Substances 0.000 claims description 4
- 230000001713 cholinergic effect Effects 0.000 claims description 4
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- 239000003085 diluting agent Substances 0.000 claims description 4
- 230000006984 memory degeneration Effects 0.000 claims description 4
- 208000023060 memory loss Diseases 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 4
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- SODJXZKVCLJFEE-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-phenylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(S1)=CC=C1C1=CC=CC=C1 SODJXZKVCLJFEE-UHFFFAOYSA-N 0.000 claims description 2
- FTMRKAUMDVXFDC-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-2-ylthiophen-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CSC=1C1=CC=CS1 FTMRKAUMDVXFDC-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
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- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 33
- YFNUMKDCWUSIRV-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-phenylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(SC=1)=CC=1C1=CC=CC=C1 YFNUMKDCWUSIRV-UHFFFAOYSA-N 0.000 claims 1
- QOXDDTRJHUWFSC-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-pyridin-3-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(OC=1)=CC=1C1=CC=CN=C1 QOXDDTRJHUWFSC-UHFFFAOYSA-N 0.000 claims 1
- JLQSEOZBGVGQAI-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(4-thiophen-3-ylthiophen-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(SC=1)=CC=1C=1C=CSC=1 JLQSEOZBGVGQAI-UHFFFAOYSA-N 0.000 claims 1
- MBWNIKDPLGYNBF-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-3-ylfuran-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=COC=1C1=CC=CN=C1 MBWNIKDPLGYNBF-UHFFFAOYSA-N 0.000 claims 1
- MBEIHBWZBVTMFZ-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-pyridin-4-ylfuran-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=COC=1C1=CC=NC=C1 MBEIHBWZBVTMFZ-UHFFFAOYSA-N 0.000 claims 1
- CFSYVLPMJBCKBT-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-2-ylfuran-2-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(O1)=CC=C1C1=CC=CS1 CFSYVLPMJBCKBT-UHFFFAOYSA-N 0.000 claims 1
- YYSWQOGFUOIEAW-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-(5-thiophen-3-ylthiophen-3-yl)methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=CSC=1C=1C=CSC=1 YYSWQOGFUOIEAW-UHFFFAOYSA-N 0.000 claims 1
- CEHAHHKXNFJLFU-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[4-(furan-2-yl)thiophen-2-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(SC=1)=CC=1C1=CC=CO1 CEHAHHKXNFJLFU-UHFFFAOYSA-N 0.000 claims 1
- CQFWWHVPHZLRIX-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(furan-3-yl)furan-3-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(C=1)=COC=1C=1C=COC=1 CQFWWHVPHZLRIX-UHFFFAOYSA-N 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 1
- 101150064138 MAP1 gene Proteins 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000003446 ligand Substances 0.000 abstract description 33
- 108010009685 Cholinergic Receptors Proteins 0.000 abstract 1
- 102000034337 acetylcholine receptors Human genes 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 110
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 68
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 52
- 239000002585 base Substances 0.000 description 49
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 33
- 235000019439 ethyl acetate Nutrition 0.000 description 25
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
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- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 4
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- RROBIDXNTUAHFW-UHFFFAOYSA-N benzotriazol-1-yloxy-tris(dimethylamino)phosphanium Chemical compound C1=CC=C2N(O[P+](N(C)C)(N(C)C)N(C)C)N=NC2=C1 RROBIDXNTUAHFW-UHFFFAOYSA-N 0.000 description 3
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- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- 238000007347 radical substitution reaction Methods 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000005586 smoking cessation Effects 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
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- 238000010561 standard procedure Methods 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 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
- 238000000844 transformation Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- 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
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
-
- A—HUMAN NECESSITIES
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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
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- A—HUMAN NECESSITIES
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- 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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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
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- 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)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| SE0202430-5 | 2002-08-14 | ||
| SE0202430A SE0202430D0 (sv) | 2002-08-14 | 2002-08-14 | New Compounds |
| PCT/SE2003/001277 WO2004016617A1 (en) | 2002-08-14 | 2003-08-13 | Biaryl diazabicycloalkane amides as nicotinic acetylcholine agonists |
Publications (2)
| Publication Number | Publication Date |
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| AU2003248592A1 AU2003248592A1 (en) | 2004-03-03 |
| AU2003248592B2 true AU2003248592B2 (en) | 2008-04-03 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| AU2003248592A Expired - Fee Related AU2003248592B2 (en) | 2002-08-14 | 2003-08-13 | Biaryl diazabicycloalkane amides as nicotinic acetylcholine agonists |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US20050239774A1 (enExample) |
| EP (1) | EP1539765B1 (enExample) |
| JP (1) | JP2006507241A (enExample) |
| KR (1) | KR20060002727A (enExample) |
| CN (1) | CN100343256C (enExample) |
| AT (1) | ATE417049T1 (enExample) |
| AU (1) | AU2003248592B2 (enExample) |
| BR (1) | BR0313234A (enExample) |
| CA (1) | CA2493920A1 (enExample) |
| DE (1) | DE60325234D1 (enExample) |
| ES (1) | ES2316848T3 (enExample) |
| IL (1) | IL166416A0 (enExample) |
| MX (1) | MXPA05001583A (enExample) |
| NO (1) | NO20051259L (enExample) |
| NZ (1) | NZ537882A (enExample) |
| SE (1) | SE0202430D0 (enExample) |
| WO (1) | WO2004016617A1 (enExample) |
| ZA (1) | ZA200501226B (enExample) |
Families Citing this family (48)
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| SE521512C2 (sv) | 2001-06-25 | 2003-11-11 | Niconovum Ab | Anordning för administrering av en substans till främre delen av en individs munhåla |
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| SE0202465D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New compounds |
| AU2003276919B2 (en) | 2002-09-25 | 2013-05-16 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, and benzoisothiazoles, and preparation and uses thereof |
| CA2511185C (en) | 2002-12-20 | 2012-09-18 | Niconovum Ab | A physically and chemically stable nicotine-containing particulate material |
| MXPA05006861A (es) * | 2003-02-27 | 2005-12-12 | Neurosearch As | Derivados arildiazabiciclicos novedosos. |
| WO2005063767A2 (en) | 2003-12-22 | 2005-07-14 | Memory Pharmaceuticals Corporation | Indoles, 1h-indazoles, 1,2-benzisoxazoles, and 1,2-benzisothiazoles, and preparation and uses thereof |
| JP2007515480A (ja) * | 2003-12-22 | 2007-06-14 | アストラゼネカ・アクチエボラーグ | ニコチン性アセチルコリンレセプターリガンド |
| TW200529860A (en) * | 2003-12-22 | 2005-09-16 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
| JP2007520527A (ja) * | 2004-02-04 | 2007-07-26 | ノイロサーチ アクティーゼルスカブ | 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環式アリール誘導体 |
| US20050234095A1 (en) | 2004-03-25 | 2005-10-20 | Wenge Xie | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, and preparation and uses thereof |
| JP2007534692A (ja) | 2004-04-22 | 2007-11-29 | メモリー・ファーマシューティカルズ・コーポレイション | インドール、１ｈ−インダゾール、１，２−ベンズイソキサゾール、１，２−ベンゾイソチアゾール、ならびにその調製および使用 |
| 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 |
| CN100588657C (zh) * | 2004-10-15 | 2010-02-10 | 神经研究公司 | 新的氮杂双环芳基衍生物及其医药用途 |
| RU2418797C2 (ru) | 2004-12-22 | 2011-05-20 | Мемори Фармасьютиклз Корпорейшн | Лиганды никотинового рецептора альфа-7, их получение и применение |
| US7855208B2 (en) | 2006-02-14 | 2010-12-21 | Neurosearch A/S | 3, 9-diazabicyclo(3.3.1)non-3-yl-aryl methanone derivatives as nicotinic acetylcholine receptor agonists |
| JP5694645B2 (ja) | 2006-03-16 | 2015-04-01 | ニコノヴァム エービーＮｉｃｏｎｏｖｕｍ Ａｂ | 改善された嗅ぎたばこ組成物 |
| EP2049538A1 (en) | 2006-05-30 | 2009-04-22 | NeuroSearch A/S | Novel 1,4-diaza-bicyclo[3.2.2]nonyl pyrimidinyl derivatives and their medical use |
| TWI454262B (zh) * | 2006-11-02 | 2014-10-01 | Targacept Inc | 菸鹼乙醯膽鹼受體亞型選擇性之二氮雜雙環烷類醯胺 |
| 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 |
| US20100298306A1 (en) * | 2007-10-22 | 2010-11-25 | Memory Pharmaceuticals Corporation | (1,4-Diaza-bicyclo[3.2.2]non-6-en-4-yl)-heterocyclyl-methanone Ligands for Nicotinic Acetylcholine Receptors, Useful for the Treatment of Disease |
| GB0724251D0 (en) | 2007-12-12 | 2008-02-06 | Univ Edinburgh | Therapeutic compounds and their use |
| GB0804685D0 (en) | 2008-03-13 | 2008-04-16 | Univ Edinburgh | Therapeutic compounds and their use |
| TWI488854B (zh) | 2008-06-20 | 2015-06-21 | Astrazeneca Ab | 二苯并噻氮呯衍生物及其用途 |
| 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 |
| WO2010146338A1 (en) | 2009-06-15 | 2010-12-23 | The University Of Edinburgh | Amido-isothiazole compounds and their use as inhibitors of 11beta-hsd1 for the treatment of metabolic syndrome and related disorders |
| AU2010297068B2 (en) | 2009-09-16 | 2015-10-01 | The University Of Edinburgh | (4-phenyl-piperidin-1-yl)-[5-1H-pyrazol-4yl)-thiophen-3-yl]-methanone compounds and their use |
| CA2826623A1 (en) * | 2010-02-03 | 2011-08-11 | Meh Associates, Inc | Multiple substituted fluoromethanes as selective and bioactive isosteres |
| KR101714820B1 (ko) | 2010-04-29 | 2017-03-09 | 더 유니버시티 오브 에든버러 | 11(베타)-ｈｓｄ1의 억제제로서 3,3-이치환된-(8-아자-비시클로[3.2.1]옥트-8-일)-[5-(1h-피라졸-4-일)-티오펜-3-일]-메탄온 |
| JP5749797B2 (ja) | 2010-05-17 | 2015-07-15 | フォルム ファーマシューティカルズ、インコーポレイテッド | （ｒ）−７−クロロ−ｎ−（キヌクリジン−３−イル）ベンゾ［ｂ］チオフェン−２−カルボキサミド塩酸塩一水和物の結晶形 |
| ES2603032T3 (es) * | 2010-07-15 | 2017-02-23 | Bayer Intellectual Property Gmbh | Compuestos de 3-piridil-heteroarilcarboxamida como pesticidas |
| GB201111704D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Novel compounds |
| GB201111705D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Compounds and their use |
| JO3115B1 (ar) | 2011-08-22 | 2017-09-20 | Takeda Pharmaceuticals Co | مركبات بيريدازينون واستخدامها كمثبطات daao |
| CA2872005A1 (en) | 2012-05-08 | 2013-11-14 | Forum Pharmaceuticals, Inc. | Methods of maintaining, treating or improving cognitive function |
| GB201209587D0 (en) | 2012-05-30 | 2012-07-11 | Takeda Pharmaceutical | Therapeutic compounds |
| MA37975B2 (fr) * | 2012-09-11 | 2021-03-31 | Genzyme Corp | Inhibiteurs de synthase de glucosylcéramide |
| JP6478923B2 (ja) | 2013-02-07 | 2019-03-06 | ヘプタレス セラピューティクス リミテッドＨｅｐｔａｒｅｓ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ | ムスカリンｍ４受容体アゴニストとしてのピペリジン−１−イル及びアゼピン−１−イルカルボキシレート |
| EA029430B1 (ru) | 2013-06-21 | 2018-03-30 | Такеда Фармасьютикл Компани Лимитед | Производные 1-сульфонилпиперидина в качестве модуляторов рецепторов прокинетицина |
| GB201314286D0 (en) | 2013-08-08 | 2013-09-25 | Takeda Pharmaceutical | Therapeutic Compounds |
| GB201318222D0 (en) | 2013-10-15 | 2013-11-27 | Takeda Pharmaceutical | Novel compounds |
| GB201320905D0 (en) | 2013-11-27 | 2014-01-08 | Takeda Pharmaceutical | Therapeutic compounds |
| TW201613864A (en) | 2014-02-20 | 2016-04-16 | Takeda Pharmaceutical | Novel compounds |
| GB201616839D0 (en) | 2016-10-04 | 2016-11-16 | Takeda Pharmaceutical Company Limited | Therapeutic compounds |
| GB201619514D0 (en) | 2016-11-18 | 2017-01-04 | Takeda Pharmaceuticals Co | Novel compounds |
| US12083115B2 (en) | 2020-02-03 | 2024-09-10 | Genzyme Corporation | Methods for treating neurological symptoms associated with lysosomal storage diseases |
| JP2021138648A (ja) | 2020-03-04 | 2021-09-16 | 武田薬品工業株式会社 | 経口固形製剤 |
| BR112023000798A2 (pt) | 2020-07-24 | 2023-02-07 | Genzyme Corp | Composições farmacêuticas compreendendo venglustat |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3281423A (en) * | 1964-02-03 | 1966-10-25 | Merck & Co Inc | 1, 3-ethanopiperazines and process |
| US4895943A (en) * | 1988-10-25 | 1990-01-23 | Pfizer Inc. | Preparation of 1,4-diazabicyclo(3.2.2)nonane |
| US5679673A (en) * | 1992-09-24 | 1997-10-21 | The United States Of America, Represented By The Department Of Health And Human Services | Aralkyl bridged diazabicycloalkane derivatives for CNS disorders |
| 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 |
| FR2809731B1 (fr) * | 2000-05-31 | 2002-07-19 | Sanofi Synthelabo | Derives de 1,4-diazabicyclo-[3.2.2] nonane-pheylisoxazole, leur preparation et leur application en therapeutique |
| FR2809732B1 (fr) * | 2000-05-31 | 2002-07-19 | Sanofi Synthelabo | DERIVES DE 4(-2-PHENYLTHIAZOL-5-yl)-1,4-DIAZABICYCLO-[3.2.2] NONANE, LEUR PREPARATION ET LEUR APPLICATION ENTHERAPEUTIQUE |
| SE0202465D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New compounds |
| MXPA05006861A (es) * | 2003-02-27 | 2005-12-12 | Neurosearch As | Derivados arildiazabiciclicos novedosos. |
| TW200529860A (en) * | 2003-12-22 | 2005-09-16 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
| JP2007515480A (ja) * | 2003-12-22 | 2007-06-14 | アストラゼネカ・アクチエボラーグ | ニコチン性アセチルコリンレセプターリガンド |
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2002
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2003
- 2003-08-13 BR BR0313234-0A patent/BR0313234A/pt not_active IP Right Cessation
- 2003-08-13 DE DE60325234T patent/DE60325234D1/de not_active Expired - Fee Related
- 2003-08-13 CA CA002493920A patent/CA2493920A1/en not_active Abandoned
- 2003-08-13 US US10/524,484 patent/US20050239774A1/en not_active Abandoned
- 2003-08-13 CN CNB038194791A patent/CN100343256C/zh not_active Expired - Fee Related
- 2003-08-13 KR KR1020057002265A patent/KR20060002727A/ko not_active Ceased
- 2003-08-13 ES ES03788214T patent/ES2316848T3/es not_active Expired - Lifetime
- 2003-08-13 WO PCT/SE2003/001277 patent/WO2004016617A1/en not_active Ceased
- 2003-08-13 AU AU2003248592A patent/AU2003248592B2/en not_active Expired - Fee Related
- 2003-08-13 NZ NZ537882A patent/NZ537882A/en unknown
- 2003-08-13 AT AT03788214T patent/ATE417049T1/de not_active IP Right Cessation
- 2003-08-13 JP JP2004529002A patent/JP2006507241A/ja active Pending
- 2003-08-13 MX MXPA05001583A patent/MXPA05001583A/es unknown
- 2003-08-13 EP EP03788214A patent/EP1539765B1/en not_active Expired - Lifetime
-
2005
- 2005-01-20 IL IL16641605A patent/IL166416A0/xx unknown
- 2005-02-10 ZA ZA200501226A patent/ZA200501226B/en unknown
- 2005-03-11 NO NO20051259A patent/NO20051259L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NZ537882A (en) | 2008-02-29 |
| EP1539765B1 (en) | 2008-12-10 |
| WO2004016617A1 (en) | 2004-02-26 |
| ZA200501226B (en) | 2006-07-26 |
| CN100343256C (zh) | 2007-10-17 |
| MXPA05001583A (es) | 2005-04-25 |
| ES2316848T3 (es) | 2009-04-16 |
| US20050239774A1 (en) | 2005-10-27 |
| CA2493920A1 (en) | 2004-02-26 |
| CN1678615A (zh) | 2005-10-05 |
| KR20060002727A (ko) | 2006-01-09 |
| EP1539765A1 (en) | 2005-06-15 |
| ATE417049T1 (de) | 2008-12-15 |
| JP2006507241A (ja) | 2006-03-02 |
| BR0313234A (pt) | 2005-06-14 |
| AU2003248592A1 (en) | 2004-03-03 |
| SE0202430D0 (sv) | 2002-08-14 |
| HK1077571A1 (en) | 2006-02-17 |
| NO20051259L (no) | 2005-05-12 |
| DE60325234D1 (de) | 2009-01-22 |
| IL166416A0 (en) | 2006-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK25 | Application lapsed reg. 22.2i(2) - failure to pay acceptance fee |