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 556
- 125000004432 carbon atoms Chemical group C* 0.000 claims 480
- -1 carboxymethyl -O Chemical class 0.000 claims 139
- 150000001875 compounds Chemical class 0.000 claims 110
- 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
- 239000011780 sodium chloride Substances 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
- 239000000203 mixture Substances 0.000 claims 43
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 40
- 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
- 241000143392 Oar Species 0.000 claims 25
- 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 atoms 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
- 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
- 125000004429 atoms Chemical group 0.000 claims 20
- 229910052760 oxygen Inorganic materials 0.000 claims 20
- YIKSCQDJHCMVMK-UHFFFAOYSA-N oxalic acid diamide 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
- 230000000051 modifying Effects 0.000 claims 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- BDAGIHXWWSANSR-UHFFFAOYSA-M methanoate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 6
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 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
- 125000003302 alkenyloxy group Chemical group 0.000 claims 5
- 125000005080 alkoxycarbonylalkenyl 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
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-M fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims 5
- PTRJHYDRYXRGEL-UHFFFAOYSA-N 2,3,5,6-tetrahydropyran Chemical group [CH]1CCOCC1 PTRJHYDRYXRGEL-UHFFFAOYSA-N 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
- 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
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 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
- PWOGVNFZFBRJMJ-RSAXXLAASA-N N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-5-methoxy-N-methyl-1H-indazole-3-carboxamide;formic acid Chemical compound OC=O.C1N(CC2)CCC2[C@H]1N(C)C(=O)C1=NNC2=CC=C(OC)C=C21 PWOGVNFZFBRJMJ-RSAXXLAASA-N 0.000 claims 3
- FKJXEPCGRGZLEH-RSAXXLAASA-N N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-6-methoxy-N-methyl-1H-indazole-3-carboxamide;formic acid Chemical compound OC=O.C1N(CC2)CCC2[C@H]1N(C)C(=O)C1=NNC2=CC(OC)=CC=C21 FKJXEPCGRGZLEH-RSAXXLAASA-N 0.000 claims 3
- WDKFYPHQEJOHTR-FYZYNONXSA-N N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-N-methyl-6-(oxan-4-yl)-1H-indazole-3-carboxamide;formic acid Chemical compound OC=O.CN([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NNC1=CC=2C1CCOCC1 WDKFYPHQEJOHTR-FYZYNONXSA-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
- 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 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
- ZXAZWXJOKVUXST-UHFFFAOYSA-N 3'-methyl-N-(3'-methylspiro[1,3-dithiolane-2,4'-6,7-dihydro-5H-1-benzofuran]-2'-carbonyl)-N-(2-morpholin-4-ylethyl)spiro[1,3-dithiolane-2,4'-6,7-dihydro-5H-1-benzofuran]-2'-carboxamide Chemical compound C1=2C(C)=C(C(=O)N(CCN3CCOCC3)C(=O)C3=C(C=4C5(SCCS5)CCCC=4O3)C)OC=2CCCC21SCCS2 ZXAZWXJOKVUXST-UHFFFAOYSA-N 0.000 claims 2
- 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
- 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
- IKLCRHCCDTVDLC-FERBBOLQSA-N N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-6-(2-oxo-3-propylimidazolidin-1-yl)-1H-indazole-3-carboxamide;formic acid Chemical compound OC=O.O=C1N(CCC)CCN1C1=CC=C(C(=NN2)C(=O)N[C@@H]3C4CCN(CC4)C3)C2=C1 IKLCRHCCDTVDLC-FERBBOLQSA-N 0.000 claims 2
- PTCTWELVZLSBMS-PBCDJRLTSA-N N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-6-(3-methoxypyrrolidin-1-yl)-1H-indazole-3-carboxamide;formic acid Chemical compound OC=O.C1C(OC)CCN1C1=CC=C(C(=NN2)C(=O)N[C@@H]3C4CCN(CC4)C3)C2=C1 PTCTWELVZLSBMS-PBCDJRLTSA-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
- SALPMAXLHRQAPQ-QUENFVSXSA-N N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-6-[1-(cyclopropanecarbonyl)-3,4,4a,5,7,7a-hexahydro-2H-pyrrolo[3,4-b]pyridin-6-yl]-1,2-benzothiazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NSC1=CC=2N(CC12)CC1CCCN2C(=O)C1CC1 SALPMAXLHRQAPQ-QUENFVSXSA-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
- 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
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- XIYQUORHPQHVQN-AWEZNQCLSA-N N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-6-cyano-1H-indazole-3-carboxamide Chemical compound N#CC1=CC=C2C(C(N[C@@H]3C4CCN(CC4)C3)=O)=NNC2=C1 XIYQUORHPQHVQN-AWEZNQCLSA-N 0.000 claims 1
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- OZIYFRRXGPXXDW-INIZCTEOSA-N N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-6-piperazin-1-yl-1,2-benzothiazole-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NSC1=CC=2N1CCNCC1 OZIYFRRXGPXXDW-INIZCTEOSA-N 0.000 claims 1
- OPNCHKXTZMMPLE-ZBFHGGJFSA-N N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-7-[(3R)-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-ZBFHGGJFSA-N 0.000 claims 1
- 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
- XDPQUPREVRZXNO-NSHDSACASA-N N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-7-fluoro-6-methoxy-1,2-benzothiazole-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NSC2=C(F)C(OC)=CC=C21 XDPQUPREVRZXNO-NSHDSACASA-N 0.000 claims 1
- HRVKBVFUVVMHSK-FYZYNONXSA-N N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-N-methyl-5-(oxan-4-yl)-1H-indazole-3-carboxamide;formic acid Chemical compound OC=O.CN([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=C2)=NNC1=CC=C2C1CCOCC1 HRVKBVFUVVMHSK-FYZYNONXSA-N 0.000 claims 1
- JGPVBCRPPKXMBU-NTISSMGPSA-N N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-N-methyl-6-(1,3-thiazol-2-yl)-1H-indazole-3-carboxamide;formic acid Chemical compound OC=O.CN([C@@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NNC1=CC=2C1=NC=CS1 JGPVBCRPPKXMBU-NTISSMGPSA-N 0.000 claims 1
- 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
- ALOKYYKPOGJKGF-XFULWGLBSA-N N-[(3S)-1-azabicyclo[2.2.2]octan-3-yl]-1-(difluoromethyl)-6-(propylcarbamoylamino)indazole-3-carboxamide;formic acid Chemical compound OC=O.C1N(CC2)CCC2[C@@H]1NC(=O)C1=NN(C(F)F)C2=CC(NC(=O)NCCC)=CC=C21 ALOKYYKPOGJKGF-XFULWGLBSA-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
- KNCFDMJNBZZYJV-UTONKHPSSA-N N-[(3S)-1-azabicyclo[2.2.2]octan-3-yl]-5-hydroxy-1,2-benzothiazole-3-carboxamide;formic acid Chemical compound OC=O.C1N(CC2)CCC2[C@@H]1NC(=O)C1=NSC2=CC=C(O)C=C21 KNCFDMJNBZZYJV-UTONKHPSSA-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
- DOFXBGFMCIIQDS-BZSJEYESSA-N N-[(3S)-1-azabicyclo[2.2.2]octan-3-yl]-6-(3-ethoxypyrrolidin-1-yl)-7-fluoro-1,2-benzothiazole-3-carboxamide Chemical compound C1C(OCC)CCN1C1=CC=C(C(=NS2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1F DOFXBGFMCIIQDS-BZSJEYESSA-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
- NKXOJYFKZRKJBC-XFULWGLBSA-N N-[(3S)-1-azabicyclo[2.2.2]octan-3-yl]-6-(cyclopropanecarbonylamino)-1-(difluoromethyl)indazole-3-carboxamide;formic acid Chemical compound OC=O.C1=C2N(C(F)F)N=C(C(=O)N[C@H]3C4CCN(CC4)C3)C2=CC=C1NC(=O)C1CC1 NKXOJYFKZRKJBC-XFULWGLBSA-N 0.000 claims 1
- HSMDNIAYMXUHEP-PKLMIRHRSA-N N-[(3S)-1-azabicyclo[2.2.2]octan-3-yl]-6-(cyclopropanecarbonylamino)-1-methylindazole-3-carboxamide;formic acid Chemical compound OC=O.C1=C2N(C)N=C(C(=O)N[C@H]3C4CCN(CC4)C3)C2=CC=C1NC(=O)C1CC1 HSMDNIAYMXUHEP-PKLMIRHRSA-N 0.000 claims 1
- MFFVSJWOAHYXCB-GMUIIQOCSA-N N-[(3S)-1-azabicyclo[2.2.2]octan-3-yl]-6-(oxan-4-yloxy)-1H-indazole-3-carboxamide;formic acid Chemical compound OC=O.N([C@H]1C2CCN(CC2)C1)C(=O)C(C1=CC=2)=NNC1=CC=2OC1CCOCC1 MFFVSJWOAHYXCB-GMUIIQOCSA-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
- MQHHLXJJSOOTSK-GDBMZVCRSA-N N-[(3S)-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-GDBMZVCRSA-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
- OCGYRDFTRXESBT-MELYUZJYSA-N N-[(3S)-1-azabicyclo[2.2.2]octan-3-yl]-6-[(4S)-4-hydroxy-2-oxopyrrolidin-1-yl]-1H-indazole-3-carboxamide;formic acid Chemical compound OC=O.O=C1C[C@H](O)CN1C1=CC=C(C(=NN2)C(=O)N[C@H]3C4CCN(CC4)C3)C2=C1 OCGYRDFTRXESBT-MELYUZJYSA-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
- SXCKICSPULREIH-RFVHGSKJSA-N N-[(3S)-1-azabicyclo[2.2.2]octan-3-yl]-7-hydroxy-2H-indazole-3-carboxamide;formic acid Chemical compound OC=O.C1N(CC2)CCC2[C@@H]1NC(=O)C1=C2C=CC=C(O)C2=NN1 SXCKICSPULREIH-RFVHGSKJSA-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
- LXPRAWRASHQVLH-IEBWSBKVSA-N N12C[C@H](C(CC1)CC2)N1N=CC2=CC=C(C=C12)C(=O)N1C[C@@H](CC1)OC Chemical compound N12C[C@H](C(CC1)CC2)N1N=CC2=CC=C(C=C12)C(=O)N1C[C@@H](CC1)OC LXPRAWRASHQVLH-IEBWSBKVSA-N 0.000 claims 1
- KHCUAWLJBYKDQN-KUARMEPBSA-N OC=O.CO[C@H]1CCN(C1)c1cccc2c(nsc12)C(=O)N[C@@H]1CN2CCC1CC2 Chemical compound OC=O.CO[C@H]1CCN(C1)c1cccc2c(nsc12)C(=O)N[C@@H]1CN2CCC1CC2 KHCUAWLJBYKDQN-KUARMEPBSA-N 0.000 claims 1
- AGSLUKFSIAMOBZ-UQKRIMTDSA-N OC=O.COc1ccc2c(nsc2c1)C(=O)N(C)[C@H]1CN2CCC1CC2 Chemical compound OC=O.COc1ccc2c(nsc2c1)C(=O)N(C)[C@H]1CN2CCC1CC2 AGSLUKFSIAMOBZ-UQKRIMTDSA-N 0.000 claims 1
- ZKAGJPZAULEUGB-UNTBIKODSA-N OC=O.O=C(N[C@@H]1CN2CCC1CC2)c1nsc2cc(OCc3ccoc3)ccc12 Chemical compound OC=O.O=C(N[C@@H]1CN2CCC1CC2)c1nsc2cc(OCc3ccoc3)ccc12 ZKAGJPZAULEUGB-UNTBIKODSA-N 0.000 claims 1
- LJGUNICKAAWGDD-RFVHGSKJSA-N OC=O.O=C(N[C@@H]1CN2CCC1CC2)c1nsc2ncccc12 Chemical compound OC=O.O=C(N[C@@H]1CN2CCC1CC2)c1nsc2ncccc12 LJGUNICKAAWGDD-RFVHGSKJSA-N 0.000 claims 1
- 229940076279 Serotonin Drugs 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N Trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- 239000000480 calcium channel blocker Substances 0.000 claims 1
- 230000002149 cannabinoid Effects 0.000 claims 1
- 229930003827 cannabinoid Natural products 0.000 claims 1
- 239000003557 cannabinoid Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 239000000544 cholinesterase inhibitor Substances 0.000 claims 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims 1
- 229960003638 dopamine Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drugs Drugs 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 230000003551 muscarinic Effects 0.000 claims 1
- INYJGWAMAOSZQJ-UHFFFAOYSA-N oxamide;hydrochloride Chemical compound Cl.NC(=O)C(N)=O INYJGWAMAOSZQJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 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
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71955205P | 2005-09-23 | 2005-09-23 | |
| PCT/US2006/037142 WO2007038367A1 (en) | 2005-09-23 | 2006-09-22 | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof |
Publications (2)
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|---|---|
| JP2009509964A JP2009509964A (ja) | 2009-03-12 |
| JP2009509964A5 true JP2009509964A5 (ru) | 2010-01-07 |
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|---|---|
| EP (1) | EP1940833A1 (ru) |
| JP (1) | JP2009509964A (ru) |
| KR (1) | KR20080048550A (ru) |
| CN (1) | CN101312968A (ru) |
| AU (1) | AU2006295397A1 (ru) |
| BR (1) | BRPI0617534A2 (ru) |
| CA (1) | CA2622677A1 (ru) |
| IL (1) | IL190358A0 (ru) |
| RU (1) | RU2450003C2 (ru) |
| SG (1) | SG165417A1 (ru) |
| WO (1) | WO2007038367A1 (ru) |
| ZA (1) | ZA200802342B (ru) |
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| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| KR101280333B1 (ko) | 2006-03-28 | 2013-07-02 | 하이 포인트 파마슈티칼스, 엘엘씨 | 히스타민 ｈ３ 수용체 활성을 갖는 벤조티아졸 |
| 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 |
| CN101910131B (zh) * | 2007-11-16 | 2014-04-23 | 里格尔药品股份有限公司 | 甲酰胺、磺酰胺和胺化合物及其使用方法 |
| EP2254884B1 (en) * | 2008-02-15 | 2013-05-01 | F. Hoffmann-La Roche AG | 3-alkyl-piperazine derivatives and uses thereof |
| WO2010043515A1 (en) * | 2008-10-13 | 2010-04-22 | F. Hoffmann-La Roche Ag | Diazonium-free method to make an indazole intermediate in the synthesis of bicyclic 5-(trifluormethoxy)-1h-3-indazolecarboxylic acid amides |
| TR201807944T4 (tr) | 2008-11-19 | 2018-06-21 | Forum Pharmaceuticals Inc | (R)-7-kloro-N-(kinüklidin-3-il)benzo[b]tiyofen-2-karboksamit ve bunun farmasötik olarak kabul edilebilir tuzları ile şizofreninin negatif belirtilerinin tedavisi. |
| 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 |
| JO3250B1 (ar) | 2009-09-22 | 2018-09-16 | Novartis Ag | إستعمال منشطات مستقبل نيكوتينيك أسيتيل كولين ألفا 7 |
| 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 |
| EP2563796B1 (en) * | 2010-04-30 | 2015-03-18 | Bristol-Myers Squibb Company | Aza-bicyclic amine n-oxide compounds as alpha-7 nicotinic acetylcholine receptor ligand pro-drugs |
| ES2746850T3 (es) | 2010-05-17 | 2020-03-09 | Forum Pharmaceuticals Inc | Formulaciones farmacéuticas que comprenden formas cristalinas de clorhidrato de (R)-7-cloro-N-(quinuclidin-3-il)benzo(b)tiofeno-2-carboxamida monohidratado |
| 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 |
| CN103260619A (zh) | 2010-07-26 | 2013-08-21 | 英维沃医药有限公司 | 利用某些α-7烟酸受体激动剂与乙酰胆碱酯酶抑制剂的组合治疗认知障碍 |
| AR086791A1 (es) * | 2011-07-01 | 2014-01-22 | Lundbeck & Co As H | Moduladores alostericos positivos del receptor de acetilcolina nicotinico |
| MX358512B (es) | 2012-05-08 | 2018-08-24 | Forum Pharmaceuticals Inc | Uso de (r)-7cloro-n-(quinuclidin-3-il) benzo[b] tiofeno-2-carboxamida o una sal farmacéuticamente aceptable de la misma para preparar una composición farmacéutica en el tratamiento de una disfunción cognitiva. |
| 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 |
| WO2014061676A1 (ja) * | 2012-10-16 | 2014-04-24 | 武田薬品工業株式会社 | 複素環化合物 |
| JP2016526538A (ja) | 2013-06-20 | 2016-09-05 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 殺ダニ剤及び殺虫剤としてのアリールスルフィド誘導体及びアリールスルホキシド誘導体 |
| EP3030555B1 (en) * | 2013-08-08 | 2019-01-30 | Boehringer Ingelheim International GmbH | Novel pyrazine amide compounds |
| JP6586104B2 (ja) | 2014-03-20 | 2019-10-02 | サミュメッド リミテッド ライアビリティ カンパニー | ５−置換インダゾール−３−カルボキサミドならびにその調製および使用の方法 |
| KR101532211B1 (ko) * | 2014-04-30 | 2015-06-30 | 세종대학교산학협력단 | Ampk 억제기능에 기반한 뇌졸중 치료용 약학적 조성물 및 방법 |
| JP7055017B2 (ja) | 2014-09-29 | 2022-04-15 | 武田薬品工業株式会社 | 結晶形の１－（１－メチル－１ｈ－ピラゾール－４－イル）－ｎ－（（１ｒ，５ｓ，７ｓ）－９－メチル－３－オキサ－９－アザビシクロ［３．３．１］ノナン－７－イル）－１ｈ－インドール－３－カルボキサミド |
| AU2016274694A1 (en) * | 2015-06-10 | 2018-01-18 | Axovant Sciences Gmbh | Aminobenzisoxazole compounds as agonists of A7-nicotinic acetylcholine receptors |
| WO2017027600A1 (en) | 2015-08-12 | 2017-02-16 | Forum Pharmaceuticals, Inc. | GEMINAL SUBSTITUTED AMINOBENZISOXAZOLE COMPOUNDS AS AGONISTS OF α7-NICOTINIC ACETYLCHOLINE RECEPTORS |
| CN116270646A (zh) * | 2015-10-16 | 2023-06-23 | 艾伯维公司 | 制备咪唑并[1,2-a]吡咯并[2,3-e]吡嗪类化合物及其固态形式的方法 |
| JP7164542B2 (ja) | 2017-04-06 | 2022-11-01 | インベンティバ | 新規な化合物であるｙａｐ／ｔａｚ－ｔｅａｄ相互作用阻害剤、および悪性中皮腫の治療でのその使用 |
| EP3632908A1 (en) | 2018-10-02 | 2020-04-08 | Inventiva | Inhibitors of the yap/taz-tead interaction and their use in the treatment of cancer |
| AU2021311131A1 (en) | 2020-07-24 | 2023-03-23 | Genzyme Corporation | Pharmaceutical compositions comprising venglustat |
| US11618751B1 (en) | 2022-03-25 | 2023-04-04 | Ventus Therapeutics U.S., Inc. | Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 derivatives |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2067979C1 (ru) * | 1992-02-04 | 1996-10-20 | Эйсай Ко. Лтд. | Производное аминобензойной кислоты или его фармацевтически приемлемая соль |
| AR036040A1 (es) * | 2001-06-12 | 2004-08-04 | Upjohn Co | Compuestos de heteroarilo multiciclicos sustituidos con quinuclidinas y composiciones farmaceuticas que los contienen |
| AR036041A1 (es) * | 2001-06-12 | 2004-08-04 | Upjohn Co | Compuestos aromaticos heterociclicos sustituidos con quinuclidina y composiciones farmaceuticas que los contienen |
| DE10162375A1 (de) * | 2001-12-19 | 2003-07-10 | Bayer Ag | Bicyclische N-Aryl-amide |
| RU2323217C2 (ru) * | 2002-08-14 | 2008-04-27 | Ньюросерч А/С | Новые хинуклидиновые производные и их применение |
| RU2391341C2 (ru) * | 2002-09-25 | 2010-06-10 | Мемори Фармасьютиклз Корпорейшн | Индазолы, бензотиазолы, бензоизотиазолы, их получение и применение |
| MXPA05007689A (es) * | 2003-01-22 | 2005-09-30 | Pharmacia & Upjohn Co Llc | Tratamiento de enfermedades con agonistas completos del receptor alfa-7 de nach. |
| PT1697378E (pt) * | 2003-12-22 | 2008-02-28 | Memory Pharm Corp | Indoles, 1h-indazoles, 1,2-benzisoxazoles e 1,2-benzisotiazoles, sua preparação e utilizações |
-
2006
- 2006-09-22 JP JP2008532459A patent/JP2009509964A/ja active Pending
- 2006-09-22 SG SG201006955-7A patent/SG165417A1/en unknown
- 2006-09-22 WO PCT/US2006/037142 patent/WO2007038367A1/en active Application Filing
- 2006-09-22 AU AU2006295397A patent/AU2006295397A1/en not_active Abandoned
- 2006-09-22 BR BRPI0617534-1A patent/BRPI0617534A2/pt not_active IP Right Cessation
- 2006-09-22 KR KR1020087009574A patent/KR20080048550A/ko not_active Application Discontinuation
- 2006-09-22 CN CNA2006800439794A patent/CN101312968A/zh active Pending
- 2006-09-22 CA CA002622677A patent/CA2622677A1/en not_active Abandoned
- 2006-09-22 RU RU2008115268/04A patent/RU2450003C2/ru not_active IP Right Cessation
- 2006-09-22 EP EP06815264A patent/EP1940833A1/en not_active Withdrawn
-
2008
- 2008-03-12 ZA ZA200802342A patent/ZA200802342B/xx unknown
- 2008-03-20 IL IL190358A patent/IL190358A0/en unknown
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