JP2009509964A5 - - Google Patents
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- JP2009509964A5 JP2009509964A5 JP2008532459A JP2008532459A JP2009509964A5 JP 2009509964 A5 JP2009509964 A5 JP 2009509964A5 JP 2008532459 A JP2008532459 A JP 2008532459A JP 2008532459 A JP2008532459 A JP 2008532459A JP 2009509964 A5 JP2009509964 A5 JP 2009509964A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- carbon atoms
- azabicyclo
- oct
- carboxamide
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 551
- 125000004432 carbon atom Chemical group C* 0.000 claims 478
- -1 carboxymethyl -O Chemical class 0.000 claims 176
- 150000001875 compounds Chemical class 0.000 claims 108
- 229910052799 carbon Inorganic materials 0.000 claims 97
- 125000000753 cycloalkyl group Chemical group 0.000 claims 82
- 125000003342 alkenyl group Chemical group 0.000 claims 80
- 125000000304 alkynyl group Chemical group 0.000 claims 80
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 66
- 125000003545 alkoxy group Chemical group 0.000 claims 62
- 150000003839 salts Chemical class 0.000 claims 57
- 125000004663 dialkyl amino group Chemical group 0.000 claims 56
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 48
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 46
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 45
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 45
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 40
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 38
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 33
- 239000012453 solvate Substances 0.000 claims 33
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 32
- 125000003118 aryl group Chemical group 0.000 claims 26
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 26
- 229910052794 bromium Inorganic materials 0.000 claims 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 25
- 229910052801 chlorine Inorganic materials 0.000 claims 25
- 229910052731 fluorine Inorganic materials 0.000 claims 25
- 229910052739 hydrogen Inorganic materials 0.000 claims 25
- 229910052740 iodine Inorganic materials 0.000 claims 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 25
- 229910052757 nitrogen Inorganic materials 0.000 claims 24
- 239000002585 base Substances 0.000 claims 22
- 229920001577 copolymer Chemical group 0.000 claims 22
- 239000000203 mixture Substances 0.000 claims 22
- 150000001349 alkyl fluorides Chemical class 0.000 claims 21
- 125000000623 heterocyclic group Chemical group 0.000 claims 21
- TYUVKZGQQUXSOU-UHFFFAOYSA-N [C].OF Chemical compound [C].OF TYUVKZGQQUXSOU-UHFFFAOYSA-N 0.000 claims 20
- 229910052760 oxygen Inorganic materials 0.000 claims 20
- 125000006413 ring segment Chemical group 0.000 claims 20
- 229920006395 saturated elastomer Polymers 0.000 claims 20
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims 19
- 125000004414 alkyl thio group Chemical group 0.000 claims 18
- 150000001204 N-oxides Chemical class 0.000 claims 17
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 16
- 229910052717 sulfur Inorganic materials 0.000 claims 15
- 150000001350 alkyl halides Chemical class 0.000 claims 14
- 125000004043 oxo group Chemical group O=* 0.000 claims 13
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 12
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 10
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 125000004423 acyloxy group Chemical group 0.000 claims 8
- 125000003282 alkyl amino group Chemical group 0.000 claims 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 239000012458 free base Substances 0.000 claims 8
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 5
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 5
- LLSRLLPHUVVLQJ-UHFFFAOYSA-N 1-cycloheptyldiazepane Chemical group C1CCCCCC1N1NCCCCC1 LLSRLLPHUVVLQJ-UHFFFAOYSA-N 0.000 claims 5
- YNUPAYMXLKKJQU-UHFFFAOYSA-N 2-amino-2-hydroxy-2-nitroacetonitrile Chemical compound N#CC(O)(N)[N+]([O-])=O YNUPAYMXLKKJQU-UHFFFAOYSA-N 0.000 claims 5
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 5
- 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 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims 5
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 125000005110 aryl thio group Chemical group 0.000 claims 5
- 125000004104 aryloxy group Chemical group 0.000 claims 5
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 5
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims 5
- 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 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 4
- GGTBELZDHKHESR-UHFFFAOYSA-N 2-cycloheptyloxazepane Chemical group C1CCCCCC1N1OCCCCC1 GGTBELZDHKHESR-UHFFFAOYSA-N 0.000 claims 4
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 4
- CHHKUKIZVHLZHF-WMZOPIPTSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1[C@@H](N(C)C)CCN1C1=CC=C(C(=NS2)C(=O)N[C@@H]3C4CCN(CC4)C3)C2=C1 CHHKUKIZVHLZHF-WMZOPIPTSA-N 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- 150000003857 carboxamides Chemical class 0.000 claims 3
- LJEXBQWZLZFSSN-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1-ethyl-6-methoxyindazole-3-carboxamide Chemical compound C12=CC=C(OC)C=C2N(CC)N=C1C(=O)N[C@@H]1C(CC2)CCN2C1 LJEXBQWZLZFSSN-HNNXBMFYSA-N 0.000 claims 3
- KPKFCXSWRVNEBQ-GOSISDBHSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-1-(cyclopropylmethyl)-6-(1,3-oxazol-2-yl)indazole-3-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=C(C=C11)C=2OC=CN=2)=NN1CC1CC1 KPKFCXSWRVNEBQ-GOSISDBHSA-N 0.000 claims 3
- VQDFGMVDXFKJGX-CYBMUJFWSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-1-(difluoromethyl)-6-methoxyindazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NN(C(F)F)C2=CC(OC)=CC=C21 VQDFGMVDXFKJGX-CYBMUJFWSA-N 0.000 claims 3
- SMJVOFILIBVERT-GOSISDBHSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-1-cyclopropyl-6-(propylcarbamoylamino)indazole-3-carboxamide Chemical compound C12=CC(NC(=O)NCCC)=CC=C2C(C(=O)N[C@H]2C3CCN(CC3)C2)=NN1C1CC1 SMJVOFILIBVERT-GOSISDBHSA-N 0.000 claims 3
- LJEXBQWZLZFSSN-OAHLLOKOSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-1-ethyl-6-methoxyindazole-3-carboxamide Chemical compound C12=CC=C(OC)C=C2N(CC)N=C1C(=O)N[C@H]1C(CC2)CCN2C1 LJEXBQWZLZFSSN-OAHLLOKOSA-N 0.000 claims 3
- AOPGWWFRFLXWRH-GOSISDBHSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-1-ethyl-n-methyl-6-(1,3-oxazol-2-yl)indazole-3-carboxamide Chemical compound C1=C2N(CC)N=C(C(=O)N(C)[C@H]3C4CCN(CC4)C3)C2=CC=C1C1=NC=CO1 AOPGWWFRFLXWRH-GOSISDBHSA-N 0.000 claims 3
- XHLPSFUPKCQDKE-QGZVFWFLSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-1-propyl-6-(1,3-thiazol-2-yl)indazole-3-carboxamide Chemical compound C1=C2N(CCC)N=C(C(=O)N[C@H]3C4CCN(CC4)C3)C2=CC=C1C1=NC=CS1 XHLPSFUPKCQDKE-QGZVFWFLSA-N 0.000 claims 3
- NBLLSKMFNOYWGA-CQSZACIVSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5-(difluoromethoxy)-n-methyl-1h-indazole-3-carboxamide Chemical compound C1=C(OC(F)F)C=C2C(C(=O)N([C@H]3C4CCN(CC4)C3)C)=NNC2=C1 NBLLSKMFNOYWGA-CQSZACIVSA-N 0.000 claims 3
- CDIIRPQKBBSHHC-OAHLLOKOSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5-methoxy-n-methyl-1h-indazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1N(C)C(=O)C1=NNC2=CC=C(OC)C=C21 CDIIRPQKBBSHHC-OAHLLOKOSA-N 0.000 claims 3
- RDSODELYJDFMBF-LJQANCHMSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-n-methyl-5-(oxan-4-yl)-1h-indazole-3-carboxamide Chemical compound CN([C@H]1C2CCN(CC2)C1)C(=O)C(C1=C2)=NNC1=CC=C2C1CCOCC1 RDSODELYJDFMBF-LJQANCHMSA-N 0.000 claims 3
- VHMKMIXTXOLLSO-MRXNPFEDSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-n-methyl-6-(1,3-oxazol-2-yl)-1h-indazole-3-carboxamide Chemical compound CN([C@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NNC1=CC=2C1=NC=CO1 VHMKMIXTXOLLSO-MRXNPFEDSA-N 0.000 claims 3
- YMWLIMACGUHANC-MRXNPFEDSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-n-methyl-6-(1,3-thiazol-2-yl)-1h-indazole-3-carboxamide Chemical compound CN([C@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NNC1=CC=2C1=NC=CS1 YMWLIMACGUHANC-MRXNPFEDSA-N 0.000 claims 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- 125000006308 propyl amino group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- OEJKUAYPQOVDOO-NNBQYGFHSA-N 6-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-2-yl)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1CN2CCCC2CN1C1=CC=C2C(C(N[C@@H]3C4CCN(CC4)C3)=O)=NSC2=C1 OEJKUAYPQOVDOO-NNBQYGFHSA-N 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 2
- 125000005047 dihydroimidazolyl group Chemical group N1(CNC=C1)* 0.000 claims 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- YVMOPDSEFSCIBW-SFHVURJKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(oxan-4-yloxy)-1h-indazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=C2)=NNC1=CC=C2OC1CCOCC1 YVMOPDSEFSCIBW-SFHVURJKSA-N 0.000 claims 2
- PBHKPYHGXWPPBB-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-(1,4-diazepan-1-yl)-1,2-benzothiazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NSC1=CC=2N1CCCNCC1 PBHKPYHGXWPPBB-KRWDZBQOSA-N 0.000 claims 2
- OPCOSSJANZPAQC-OYKVQYDMSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-(1-azabicyclo[2.2.2]octan-3-yloxy)-1,2-benzothiazole-3-carboxamide Chemical compound C1N(CC2)CCC2C1OC1=CC=C2C(C(N[C@@H]3C4CCN(CC4)C3)=O)=NSC2=C1 OPCOSSJANZPAQC-OYKVQYDMSA-N 0.000 claims 2
- GPWNPAULGBLLEA-TVPLGVNVSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-(5-methyl-2,5-diazabicyclo[2.2.2]octan-2-yl)-1,2-benzothiazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NSC2=CC(N3CC4CCC3CN4C)=CC=C21 GPWNPAULGBLLEA-TVPLGVNVSA-N 0.000 claims 2
- YIPLPZONCABMSW-QRTARXTBSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NSC2=CC(N3C[C@]4(NC[C@]3([H])C4)[H])=CC=C21 YIPLPZONCABMSW-QRTARXTBSA-N 0.000 claims 2
- MQHHLXJJSOOTSK-ZBFHGGJFSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=CC=C(C(=NS2)C(=O)N[C@@H]3C4CCN(CC4)C3)C2=C1 MQHHLXJJSOOTSK-ZBFHGGJFSA-N 0.000 claims 2
- JRLOWLLNQWPBTN-IBYPIGCZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-[3-(methoxymethyl)pyrrolidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1C(COC)CCN1C1=CC=C(C(=NS2)C(=O)N[C@@H]3C4CCN(CC4)C3)C2=C1 JRLOWLLNQWPBTN-IBYPIGCZSA-N 0.000 claims 2
- OFFFQICGZLVGEA-JRZJBTRGSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-[3-(methylamino)pyrrolidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1C(NC)CCN1C1=CC=C(C(=NS2)C(=O)N[C@@H]3C4CCN(CC4)C3)C2=C1 OFFFQICGZLVGEA-JRZJBTRGSA-N 0.000 claims 2
- KWZVHFOFVCRKOY-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-methoxy-1,2-benzothiazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NSC2=CC(OC)=CC=C21 KWZVHFOFVCRKOY-ZDUSSCGKSA-N 0.000 claims 2
- PIDKUZOOEPTSPI-RDJZCZTQSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-7-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1[C@@H](N(C)C)CCN1C1=CC=CC2=C1SN=C2C(=O)N[C@@H]1C(CC2)CCN2C1 PIDKUZOOEPTSPI-RDJZCZTQSA-N 0.000 claims 2
- SNBVUKVTZTVDTO-WUJWULDRSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-7-fluoro-6-(3-methoxypyrrolidin-1-yl)-1,2-benzothiazole-3-carboxamide Chemical compound C1C(OC)CCN1C1=CC=C(C(=NS2)C(=O)N[C@@H]3C4CCN(CC4)C3)C2=C1F SNBVUKVTZTVDTO-WUJWULDRSA-N 0.000 claims 2
- ZGGYIVUEFFUZRX-GFCCVEGCSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-1h-pyrazolo[3,4-c]pyridine-3-carboxamide Chemical compound N1=CC=C2C(C(N[C@H]3C4CCN(CC4)C3)=O)=NNC2=C1 ZGGYIVUEFFUZRX-GFCCVEGCSA-N 0.000 claims 2
- FEDPYWYAMNIXBE-UTONKHPSSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-1h-pyrazolo[3,4-c]pyridine-3-carboxamide;formic acid Chemical compound OC=O.N1=CC=C2C(C(N[C@H]3C4CCN(CC4)C3)=O)=NNC2=C1 FEDPYWYAMNIXBE-UTONKHPSSA-N 0.000 claims 2
- PPNSPIJCCHPEIW-NVXWUHKLSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5-[(3r)-3-methoxypyrrolidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1[C@H](OC)CCN1C1=CC=C(SN=C2C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 PPNSPIJCCHPEIW-NVXWUHKLSA-N 0.000 claims 2
- MRWSLRJLSYNXEP-QGZVFWFLSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(1,3-oxazol-2-yl)-1-propylindazole-3-carboxamide Chemical compound C1=C2N(CCC)N=C(C(=O)N[C@H]3C4CCN(CC4)C3)C2=CC=C1C1=NC=CO1 MRWSLRJLSYNXEP-QGZVFWFLSA-N 0.000 claims 2
- OPCOSSJANZPAQC-MRTLOADZSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(1-azabicyclo[2.2.2]octan-3-yloxy)-1,2-benzothiazole-3-carboxamide Chemical compound C1N(CC2)CCC2C1OC1=CC=C2C(C(N[C@H]3C4CCN(CC4)C3)=O)=NSC2=C1 OPCOSSJANZPAQC-MRTLOADZSA-N 0.000 claims 2
- UFVCXVYNCMTGHK-MRXNPFEDSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(1-methyl-4,5-dihydroimidazol-2-yl)-1h-indazole-3-carboxamide Chemical compound CN1CCN=C1C1=CC=C(C(=NN2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 UFVCXVYNCMTGHK-MRXNPFEDSA-N 0.000 claims 2
- GRUNLFXWKKKXLJ-GOSISDBHSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(2-oxo-3-propylimidazolidin-1-yl)-1h-indazole-3-carboxamide Chemical compound O=C1N(CCC)CCN1C1=CC=C(C(=NN2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 GRUNLFXWKKKXLJ-GOSISDBHSA-N 0.000 claims 2
- JCBHEXJAZCRMNJ-MRXNPFEDSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(3-methylpyrazol-1-yl)-1,2-benzothiazole-3-carboxamide Chemical compound N1=C(C)C=CN1C1=CC=C(C(=NS2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 JCBHEXJAZCRMNJ-MRXNPFEDSA-N 0.000 claims 2
- AIEYPFNAZAQGDT-GOSISDBHSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(4-methyl-1,4-diazepan-1-yl)-1,2-benzothiazole-3-carboxamide Chemical compound C1CN(C)CCCN1C1=CC=C(C(=NS2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 AIEYPFNAZAQGDT-GOSISDBHSA-N 0.000 claims 2
- GPWNPAULGBLLEA-FAFZWHIHSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(5-methyl-2,5-diazabicyclo[2.2.2]octan-2-yl)-1,2-benzothiazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NSC2=CC(N3CC4CCC3CN4C)=CC=C21 GPWNPAULGBLLEA-FAFZWHIHSA-N 0.000 claims 2
- ZYXWSPGDIGRWLF-MRXNPFEDSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(5-methylpyrazol-1-yl)-1,2-benzothiazole-3-carboxamide Chemical compound CC1=CC=NN1C1=CC=C(C(=NS2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 ZYXWSPGDIGRWLF-MRXNPFEDSA-N 0.000 claims 2
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- OPNCHKXTZMMPLE-HOCLYGCPSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-7-[(3s)-3-methoxypyrrolidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1[C@@H](OC)CCN1C1=CC=CC2=C1SN=C2C(=O)N[C@@H]1C(CC2)CCN2C1 OPNCHKXTZMMPLE-HOCLYGCPSA-N 0.000 claims 1
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- YLWNWPRABKNCGA-CQSZACIVSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-1-(difluoromethyl)-6-(1,3-thiazol-2-yl)indazole-3-carboxamide Chemical compound C1=C2N(C(F)F)N=C(C(=O)N[C@H]3C4CCN(CC4)C3)C2=CC=C1C1=NC=CS1 YLWNWPRABKNCGA-CQSZACIVSA-N 0.000 claims 1
- OMIAFJAGVHVDCS-QGZVFWFLSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-1-cyclopropyl-6-(1,3-thiazol-2-yl)indazole-3-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=C(C=C11)C=2SC=CN=2)=NN1C1CC1 OMIAFJAGVHVDCS-QGZVFWFLSA-N 0.000 claims 1
- DLARADLKNHHUJE-MRXNPFEDSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-1-ethyl-6-(1,3-oxazol-2-yl)indazole-3-carboxamide Chemical compound C1=C2N(CC)N=C(C(=O)N[C@H]3C4CCN(CC4)C3)C2=CC=C1C1=NC=CO1 DLARADLKNHHUJE-MRXNPFEDSA-N 0.000 claims 1
- KRLDSELWMMWNML-PKLMIRHRSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-1-ethyl-6-(1,3-oxazol-2-yl)indazole-3-carboxamide;hydrochloride Chemical compound Cl.C1=C2N(CC)N=C(C(=O)N[C@H]3C4CCN(CC4)C3)C2=CC=C1C1=NC=CO1 KRLDSELWMMWNML-PKLMIRHRSA-N 0.000 claims 1
- IKXVBFQRYVFHDF-QGZVFWFLSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-1-propan-2-yl-6-(1,3-thiazol-2-yl)indazole-3-carboxamide Chemical compound C1=C2N(C(C)C)N=C(C(=O)N[C@H]3C4CCN(CC4)C3)C2=CC=C1C1=NC=CS1 IKXVBFQRYVFHDF-QGZVFWFLSA-N 0.000 claims 1
- HVKLEJMKAONLIB-GOSISDBHSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5-(4-methyl-1,4-diazepan-1-yl)-1,2-benzothiazole-3-carboxamide Chemical compound C1CN(C)CCCN1C1=CC=C(SN=C2C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 HVKLEJMKAONLIB-GOSISDBHSA-N 0.000 claims 1
- HCHKVJNYNKHIGB-GOSISDBHSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(1,3-thiazol-2-yl)-1-thiophen-3-ylindazole-3-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=C(C=C11)C=2SC=CN=2)=NN1C=1C=CSC=1 HCHKVJNYNKHIGB-GOSISDBHSA-N 0.000 claims 1
- PBHKPYHGXWPPBB-QGZVFWFLSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(1,4-diazepan-1-yl)-1,2-benzothiazole-3-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NSC1=CC=2N1CCCNCC1 PBHKPYHGXWPPBB-QGZVFWFLSA-N 0.000 claims 1
- SERHSHYNJAZWGI-LRHAYUFXSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(2-methylpiperazin-1-yl)-1,2-benzothiazole-3-carboxamide Chemical compound CC1CNCCN1C1=CC=C(C(=NS2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 SERHSHYNJAZWGI-LRHAYUFXSA-N 0.000 claims 1
- GJYQRQQHVVMNQQ-UNTBIKODSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(2-oxo-3-propylimidazolidin-1-yl)-1,2-benzothiazole-3-carboxamide;hydrochloride Chemical compound Cl.O=C1N(CCC)CCN1C1=CC=C(C(=NS2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 GJYQRQQHVVMNQQ-UNTBIKODSA-N 0.000 claims 1
- WGFXFRVKAYTEOV-MRXNPFEDSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(3-ethyl-2-oxoimidazolidin-1-yl)-1,2-benzothiazole-3-carboxamide Chemical compound O=C1N(CC)CCN1C1=CC=C(C(=NS2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 WGFXFRVKAYTEOV-MRXNPFEDSA-N 0.000 claims 1
- MQHHLXJJSOOTSK-BZSJEYESSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(3-hydroxypyrrolidin-1-yl)-1,2-benzothiazole-3-carboxamide Chemical compound C1C(O)CCN1C1=CC=C(C(=NS2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 MQHHLXJJSOOTSK-BZSJEYESSA-N 0.000 claims 1
- QANNTZCRFNSNGO-OMOCHNIRSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(3-methoxypyrrolidin-1-yl)-1,2-benzothiazole-3-carboxamide Chemical compound C1C(OC)CCN1C1=CC=C(C(=NS2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 QANNTZCRFNSNGO-OMOCHNIRSA-N 0.000 claims 1
- BIBPBHIZDKQIOZ-PVQCJRHBSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(3-methyl-2-oxopyrrolidin-1-yl)-1,2-benzothiazole-3-carboxamide Chemical compound O=C1C(C)CCN1C1=CC=C(C(=NS2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 BIBPBHIZDKQIOZ-PVQCJRHBSA-N 0.000 claims 1
- XXXHTSQDIORPMB-GOSISDBHSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(4-methylpiperazine-1-carbonyl)-1h-indazole-3-carboxamide Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C(=NN2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 XXXHTSQDIORPMB-GOSISDBHSA-N 0.000 claims 1
- IVYWDRAWLTUMFE-FAFZWHIHSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-(8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl)-1,2-benzothiazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NSC2=CC(N3CC4CCC(C3)N4C)=CC=C21 IVYWDRAWLTUMFE-FAFZWHIHSA-N 0.000 claims 1
- YIPLPZONCABMSW-JLJPHGGASA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NSC2=CC(N3C[C@]4(NC[C@]3([H])C4)[H])=CC=C21 YIPLPZONCABMSW-JLJPHGGASA-N 0.000 claims 1
- YASULIPENFCLRY-CMKODMSKSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-[(1s,4s)-2-(cyclopropanecarbonyl)-2,5-diazabicyclo[2.2.1]heptan-5-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C([C@]1(N(C=2C=C3SN=C(C3=CC=2)C(=O)N[C@H]2C3CCN(CC3)C2)C[C@@]2(C1)[H])[H])N2C(=O)C1CC1 YASULIPENFCLRY-CMKODMSKSA-N 0.000 claims 1
- FJXJLRUWWLSMTO-IRFCIJBXSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-[(1s,4s)-5-(cyclopropylmethyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C([C@]1(N(C=2C=C3SN=C(C3=CC=2)C(=O)N[C@H]2C3CCN(CC3)C2)C[C@@]2(C1)[H])[H])N2CC1CC1 FJXJLRUWWLSMTO-IRFCIJBXSA-N 0.000 claims 1
- DOUKNGQHWNTBGW-CMKODMSKSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-[(1s,4s)-5-cyclopropyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C([C@]1(N(C=2C=C3SN=C(C3=CC=2)C(=O)N[C@H]2C3CCN(CC3)C2)C[C@@]2(C1)[H])[H])N2C1CC1 DOUKNGQHWNTBGW-CMKODMSKSA-N 0.000 claims 1
- DQWZCYLIBXHEIN-XYJFISCASA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-[(1s,4s)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NSC2=CC(N3C[C@]4(N(C[C@]3([H])C4)C)[H])=CC=C21 DQWZCYLIBXHEIN-XYJFISCASA-N 0.000 claims 1
- VJGNOXVGSIIBKG-DOTOQJQBSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-[(3s)-3-methoxypyrrolidin-1-yl]-1,2-benzoxazole-3-carboxamide Chemical compound C1[C@@H](OC)CCN1C1=CC=C(C(=NO2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 VJGNOXVGSIIBKG-DOTOQJQBSA-N 0.000 claims 1
- AFFLFHWMOOWDQB-ROPPNANJSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-[3-(cyclopropylmethoxy)pyrrolidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NSC1=CC=2N(C1)CCC1OCC1CC1 AFFLFHWMOOWDQB-ROPPNANJSA-N 0.000 claims 1
- OFFFQICGZLVGEA-FBMWCMRBSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-[3-(methylamino)pyrrolidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1C(NC)CCN1C1=CC=C(C(=NS2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 OFFFQICGZLVGEA-FBMWCMRBSA-N 0.000 claims 1
- KRVDZCIJALCFCD-UHUGOGIASA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-[3-[methyl(2,2,2-trifluoroethyl)amino]pyrrolidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1C(N(CC(F)(F)F)C)CCN1C1=CC=C(C(=NS2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 KRVDZCIJALCFCD-UHUGOGIASA-N 0.000 claims 1
- GOZVSIAXGOLHQP-LJQANCHMSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-[4-(dimethylamino)piperidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1CC(N(C)C)CCN1C1=CC=C(C(=NS2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 GOZVSIAXGOLHQP-LJQANCHMSA-N 0.000 claims 1
- HSNPCRQDMDXYQW-BTQNPOSSSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-methoxy-1,2-benzothiazole-3-carboxamide;hydrochloride Chemical compound Cl.C1N(CC2)CCC2[C@@H]1NC(=O)C1=NSC2=CC(OC)=CC=C21 HSNPCRQDMDXYQW-BTQNPOSSSA-N 0.000 claims 1
- ZCZQEVPJJXRPAQ-MRXNPFEDSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-6-pyrrol-1-yl-1,2-benzothiazole-3-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NSC1=CC=2N1C=CC=C1 ZCZQEVPJJXRPAQ-MRXNPFEDSA-N 0.000 claims 1
- OPNCHKXTZMMPLE-BZSJEYESSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-7-(3-methoxypyrrolidin-1-yl)-1,2-benzothiazole-3-carboxamide Chemical compound C1C(OC)CCN1C1=CC=CC2=C1SN=C2C(=O)N[C@H]1C(CC2)CCN2C1 OPNCHKXTZMMPLE-BZSJEYESSA-N 0.000 claims 1
- GLTJKJAUUMPZNP-DZGCQCFKSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-7-[(3s)-3-hydroxypyrrolidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1[C@@H](O)CCN1C1=CC=CC2=C1SN=C2C(=O)N[C@H]1C(CC2)CCN2C1 GLTJKJAUUMPZNP-DZGCQCFKSA-N 0.000 claims 1
- OPNCHKXTZMMPLE-GOEBONIOSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-7-[(3s)-3-methoxypyrrolidin-1-yl]-1,2-benzothiazole-3-carboxamide Chemical compound C1[C@@H](OC)CCN1C1=CC=CC2=C1SN=C2C(=O)N[C@H]1C(CC2)CCN2C1 OPNCHKXTZMMPLE-GOEBONIOSA-N 0.000 claims 1
- SNBVUKVTZTVDTO-AWKYBWMHSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-7-fluoro-6-(3-methoxypyrrolidin-1-yl)-1,2-benzothiazole-3-carboxamide Chemical compound C1C(OC)CCN1C1=CC=C(C(=NS2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1F SNBVUKVTZTVDTO-AWKYBWMHSA-N 0.000 claims 1
- GGWTWAGLQPRLGQ-UTONKHPSSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-7-methoxy-1,2-benzothiazole-3-carboxamide;hydrochloride Chemical compound Cl.C1N(CC2)CCC2[C@@H]1NC(=O)C1=NSC2=C1C=CC=C2OC GGWTWAGLQPRLGQ-UTONKHPSSA-N 0.000 claims 1
- WQLZMRXMTRRRQR-LJQANCHMSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-n-methyl-6-(oxan-4-yl)-1h-indazole-3-carboxamide Chemical compound CN([C@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NNC1=CC=2C1CCOCC1 WQLZMRXMTRRRQR-LJQANCHMSA-N 0.000 claims 1
- INYJGWAMAOSZQJ-UHFFFAOYSA-N oxamide;hydrochloride Chemical compound Cl.NC(=O)C(N)=O INYJGWAMAOSZQJ-UHFFFAOYSA-N 0.000 claims 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 229940076279 serotonin Drugs 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
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| AU2008322426C1 (en) * | 2007-11-16 | 2014-10-23 | Rigel Pharmaceuticals, Inc. | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
| CN101952278A (zh) * | 2008-02-15 | 2011-01-19 | 弗·哈夫曼-拉罗切有限公司 | 3-烷基-哌嗪衍生物及其用途 |
| SI2346833T1 (sl) * | 2008-10-13 | 2013-06-28 | F. Hoffmann-La Roche Ag | Postopek brez diazonija za pripravo indazolnega intermediata v sintezi bicikliäśnih amidov 5-(trifluorometoksi)-1h-3-indazolkarboksilne kisline |
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| TWI558398B (zh) | 2009-09-22 | 2016-11-21 | 諾華公司 | 菸鹼乙醯膽鹼受體α７活化劑之用途 |
| US20110172428A1 (en) | 2010-01-12 | 2011-07-14 | Shan-Ming Kuang | Methods for the preparation of indazole-3-carboxylic acid and n-(s)-1-azabicyclo[2.2.2]oct-3-yl-1h-indazole-3-carboxamide hydrochloride salt |
| WO2011137313A1 (en) * | 2010-04-30 | 2011-11-03 | Bristol-Myers Squibb Company | Aza-bicyclic amine n-oxide compounds as alpha-7 nicotinic acetylcholine receptor ligand pro-drugs |
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| US8242276B2 (en) | 2010-06-30 | 2012-08-14 | Hoffmann-La Roche Inc. | Methods for the preparation of N-(S)-1-azabicyclo[2.2.2]oct-3-yl-1H-indazole-3-carboxamide hydrochloride salt |
| BR112013001939A2 (pt) | 2010-07-26 | 2017-07-11 | Envivo Pharmaceuticals Inc | tratamento de distúrbios cognitivos com determinados agonistas receptores de ácido alfa-7-nicotínico em combinação com inibidres de acetilcolinesterase |
| AR086791A1 (es) * | 2011-07-01 | 2014-01-22 | Lundbeck & Co As H | Moduladores alostericos positivos del receptor de acetilcolina nicotinico |
| AU2013259871A1 (en) | 2012-05-08 | 2014-11-20 | Forum Pharmaceuticals Inc. | Methods of maintaining, treating or improving cognitive function |
| JOP20130213B1 (ar) | 2012-07-17 | 2021-08-17 | Takeda Pharmaceuticals Co | معارضات لمستقبلht3-5 |
| MA37975B2 (fr) * | 2012-09-11 | 2021-03-31 | Genzyme Corp | Inhibiteurs de synthase de glucosylcéramide |
| EP2927229B1 (en) | 2012-10-16 | 2018-09-05 | Takeda Pharmaceutical Company Limited | Benzene-fused 5-membered nitrogen-containing heteroaromatic compounds useful for prophylaxis or treatment of neurodegenerative diseases or epilepsy |
| EP3010889B1 (de) | 2013-06-20 | 2018-10-03 | Bayer CropScience Aktiengesellschaft | Arylsulfid- und arylsulfoxid-derivate als akarizide und insektizide |
| JP6449880B2 (ja) * | 2013-08-08 | 2019-01-09 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規ピラジンアミド化合物 |
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2006
- 2006-09-22 BR BRPI0617534-1A patent/BRPI0617534A2/pt not_active IP Right Cessation
- 2006-09-22 CA CA002622677A patent/CA2622677A1/en not_active Abandoned
- 2006-09-22 SG SG201006955-7A patent/SG165417A1/en unknown
- 2006-09-22 CN CNA2006800439794A patent/CN101312968A/zh active Pending
- 2006-09-22 KR KR1020087009574A patent/KR20080048550A/ko not_active Ceased
- 2006-09-22 JP JP2008532459A patent/JP2009509964A/ja active Pending
- 2006-09-22 RU RU2008115268/04A patent/RU2450003C2/ru not_active IP Right Cessation
- 2006-09-22 WO PCT/US2006/037142 patent/WO2007038367A1/en active Application Filing
- 2006-09-22 EP EP06815264A patent/EP1940833A1/en not_active Withdrawn
- 2006-09-22 AU AU2006295397A patent/AU2006295397A1/en not_active Abandoned
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2008
- 2008-03-12 ZA ZA200802342A patent/ZA200802342B/xx unknown
- 2008-03-20 IL IL190358A patent/IL190358A0/en unknown