JP2008516922A5 - - Google Patents
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- Publication number
- JP2008516922A5 JP2008516922A5 JP2007536122A JP2007536122A JP2008516922A5 JP 2008516922 A5 JP2008516922 A5 JP 2008516922A5 JP 2007536122 A JP2007536122 A JP 2007536122A JP 2007536122 A JP2007536122 A JP 2007536122A JP 2008516922 A5 JP2008516922 A5 JP 2008516922A5
- Authority
- JP
- Japan
- Prior art keywords
- carbonyl
- pyrrolidinyl
- phenyl
- methylethyl
- methyl
- 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.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 3
- 208000012902 Nervous system disease Diseases 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 239000012038 nucleophile Substances 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- NNPOKMDCSQIRDT-HXUWFJFHSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3r)-1-(2-methylquinolin-6-yl)pyrrolidin-3-yl]methanone Chemical compound O=C([C@@H]1CCN(C1)C1=CC2=CC=C(N=C2C=C1)C)N(CC1)CCCN1C1CCC1 NNPOKMDCSQIRDT-HXUWFJFHSA-N 0.000 claims 1
- AJZPSGNVDLHTBZ-GOSISDBHSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3r)-1-[2-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=C(F)C(N3C[C@@H](CC3)C(=O)N3CCN(CCC3)C3CCC3)=CC=2)=N1 AJZPSGNVDLHTBZ-GOSISDBHSA-N 0.000 claims 1
- CTOUODCMSJYUKJ-LJQANCHMSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3r)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)N2C[C@@H](CC2)C(=O)N2CCN(CCC2)C2CCC2)=N1 CTOUODCMSJYUKJ-LJQANCHMSA-N 0.000 claims 1
- YAORFRUOVGBQJQ-OAHLLOKOSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3r)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1=NC(C(F)(F)F)=CC=C1N1C[C@H](C(=O)N2CCN(CCC2)C2CCC2)CC1 YAORFRUOVGBQJQ-OAHLLOKOSA-N 0.000 claims 1
- NNPOKMDCSQIRDT-FQEVSTJZSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3s)-1-(2-methylquinolin-6-yl)pyrrolidin-3-yl]methanone Chemical compound O=C([C@H]1CCN(C1)C1=CC2=CC=C(N=C2C=C1)C)N(CC1)CCCN1C1CCC1 NNPOKMDCSQIRDT-FQEVSTJZSA-N 0.000 claims 1
- AJZPSGNVDLHTBZ-SFHVURJKSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3s)-1-[2-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=C(F)C(N3C[C@H](CC3)C(=O)N3CCN(CCC3)C3CCC3)=CC=2)=N1 AJZPSGNVDLHTBZ-SFHVURJKSA-N 0.000 claims 1
- CTOUODCMSJYUKJ-IBGZPJMESA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CCC2)C2CCC2)=N1 CTOUODCMSJYUKJ-IBGZPJMESA-N 0.000 claims 1
- YAORFRUOVGBQJQ-HNNXBMFYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1=NC(C(F)(F)F)=CC=C1N1C[C@@H](C(=O)N2CCN(CCC2)C2CCC2)CC1 YAORFRUOVGBQJQ-HNNXBMFYSA-N 0.000 claims 1
- YMOOGJCTAVFCJG-GOSISDBHSA-N (4-cyclobutylpiperazin-1-yl)-[(3r)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)N2C[C@@H](CC2)C(=O)N2CCN(CC2)C2CCC2)=N1 YMOOGJCTAVFCJG-GOSISDBHSA-N 0.000 claims 1
- WDARRXDQPULKMV-INIZCTEOSA-N (4-cyclobutylpiperazin-1-yl)-[(3s)-1-[3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C(=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC2)C2CCC2)F)=N1 WDARRXDQPULKMV-INIZCTEOSA-N 0.000 claims 1
- YMOOGJCTAVFCJG-SFHVURJKSA-N (4-cyclobutylpiperazin-1-yl)-[(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC2)C2CCC2)=N1 YMOOGJCTAVFCJG-SFHVURJKSA-N 0.000 claims 1
- OLXZIKGIGJIHLH-INIZCTEOSA-N (4-cyclobutylpiperazin-1-yl)-[(3s)-1-[6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2N=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC2)C2CCC2)=N1 OLXZIKGIGJIHLH-INIZCTEOSA-N 0.000 claims 1
- JTACQVQJYZNHKP-AWEZNQCLSA-N (4-cyclobutylpiperazin-1-yl)-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1=NC(C(F)(F)F)=CC=C1N1C[C@@H](C(=O)N2CCN(CC2)C2CCC2)CC1 JTACQVQJYZNHKP-AWEZNQCLSA-N 0.000 claims 1
- PKXKZAADEFDOIS-KRWDZBQOSA-N (4-ethylpiperazin-1-yl)-[(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound C1CN(CC)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 PKXKZAADEFDOIS-KRWDZBQOSA-N 0.000 claims 1
- GWARTCUETWOJMY-HNNXBMFYSA-N (4-pentan-3-ylpiperazin-1-yl)-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1CN(C(CC)CC)CCN1C(=O)[C@@H]1CN(C=2C=NC(=CC=2)C(F)(F)F)CC1 GWARTCUETWOJMY-HNNXBMFYSA-N 0.000 claims 1
- RMJUTJDMAVAABO-HNNXBMFYSA-N (4-propan-2-yl-1,4-diazepan-1-yl)-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)[C@@H]1CN(C=2C=NC(=CC=2)C(F)(F)F)CC1 RMJUTJDMAVAABO-HNNXBMFYSA-N 0.000 claims 1
- HRZIINBMVJNVJE-IBGZPJMESA-N (4-propan-2-ylpiperazin-1-yl)-[(3s)-1-(4-pyrrol-1-ylphenyl)pyrrolidin-3-yl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)N2C=CC=C2)CC1 HRZIINBMVJNVJE-IBGZPJMESA-N 0.000 claims 1
- VJZWGYSVNQTUQK-ZDUSSCGKSA-N (4-propan-2-ylpiperazin-1-yl)-[(3s)-1-[2-(trifluoromethyl)pyrimidin-5-yl]pyrrolidin-3-yl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=NC(=NC=2)C(F)(F)F)CC1 VJZWGYSVNQTUQK-ZDUSSCGKSA-N 0.000 claims 1
- YOJAJLNNCCLRHB-AWEZNQCLSA-N (4-propan-2-ylpiperazin-1-yl)-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=NC(=CC=2)C(F)(F)F)CC1 YOJAJLNNCCLRHB-AWEZNQCLSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- VYPBIEFMFRZIFJ-LJQANCHMSA-N 1-[4-[(3r)-3-(4-cyclobutyl-1,4-diazepane-1-carbonyl)pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1C[C@H](C(=O)N2CCN(CCC2)C2CCC2)CC1 VYPBIEFMFRZIFJ-LJQANCHMSA-N 0.000 claims 1
- VYPBIEFMFRZIFJ-IBGZPJMESA-N 1-[4-[(3s)-3-(4-cyclobutyl-1,4-diazepane-1-carbonyl)pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1C[C@@H](C(=O)N2CCN(CCC2)C2CCC2)CC1 VYPBIEFMFRZIFJ-IBGZPJMESA-N 0.000 claims 1
- URKJTOVLGKEWAE-IBGZPJMESA-N 1-[4-[(3s)-3-(4-pentan-3-ylpiperazine-1-carbonyl)pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1CN(C(CC)CC)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C(C)=O)CC1 URKJTOVLGKEWAE-IBGZPJMESA-N 0.000 claims 1
- UPMCRBZHCZHCPO-IBGZPJMESA-N 1-[4-[(3s)-3-(4-propan-2-yl-1,4-diazepane-1-carbonyl)pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1CN(C(C)C)CCCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C(C)=O)CC1 UPMCRBZHCZHCPO-IBGZPJMESA-N 0.000 claims 1
- AFTLCCALAJJJBT-SFHVURJKSA-N 1-[4-[(3s)-3-(4-propan-2-ylpiperazine-1-carbonyl)pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C(C)=O)CC1 AFTLCCALAJJJBT-SFHVURJKSA-N 0.000 claims 1
- PUKCWLYBBDPLFO-SFHVURJKSA-N 1-[4-[(3s)-3-(4-propan-2-ylpiperazine-1-carbonyl)pyrrolidin-1-yl]phenyl]pyrrolidin-2-one Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)N2C(CCC2)=O)CC1 PUKCWLYBBDPLFO-SFHVURJKSA-N 0.000 claims 1
- QVWXADQLHGQINK-LPHOPBHVSA-N 1-[4-[(3s)-3-[(3s)-3-methyl-4-propan-2-ylpiperazine-1-carbonyl]pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C(C)=O)CC1 QVWXADQLHGQINK-LPHOPBHVSA-N 0.000 claims 1
- NRDUEPBCTYCHEB-FQEVSTJZSA-N 1-[4-[(3s)-3-[4-(cyclopropylmethyl)-1,4-diazepane-1-carbonyl]pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1C[C@@H](C(=O)N2CCN(CC3CC3)CCC2)CC1 NRDUEPBCTYCHEB-FQEVSTJZSA-N 0.000 claims 1
- KJDLVOPRILNRCJ-IBGZPJMESA-N 1-[4-[(3s)-3-[4-(cyclopropylmethyl)piperazine-1-carbonyl]pyrrolidin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1C[C@@H](C(=O)N2CCN(CC3CC3)CC2)CC1 KJDLVOPRILNRCJ-IBGZPJMESA-N 0.000 claims 1
- DXWBJTZKDPMYNH-KRWDZBQOSA-N 3-[(3s)-3-(4-propan-2-ylpiperazine-1-carbonyl)pyrrolidin-1-yl]benzonitrile Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=C(C=CC=2)C#N)CC1 DXWBJTZKDPMYNH-KRWDZBQOSA-N 0.000 claims 1
- ADUVQOLQHWNHBQ-SFHVURJKSA-N 4-[(3s)-3-(4-propan-2-yl-1,4-diazepane-1-carbonyl)pyrrolidin-1-yl]benzonitrile Chemical compound C1CN(C(C)C)CCCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C#N)CC1 ADUVQOLQHWNHBQ-SFHVURJKSA-N 0.000 claims 1
- UCHKYAUOAIHHNW-KRWDZBQOSA-N 4-[(3s)-3-(4-propan-2-ylpiperazine-1-carbonyl)pyrrolidin-1-yl]benzonitrile Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C#N)CC1 UCHKYAUOAIHHNW-KRWDZBQOSA-N 0.000 claims 1
- IVFJQUPDJYGNPR-WMZOPIPTSA-N 4-[(3s)-3-[(3s)-3-methyl-4-propan-2-ylpiperazine-1-carbonyl]pyrrolidin-1-yl]benzonitrile Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C#N)CC1 IVFJQUPDJYGNPR-WMZOPIPTSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- QBJWLJXVGOFHFX-GOSISDBHSA-N [(3r)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@H]1CN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 QBJWLJXVGOFHFX-GOSISDBHSA-N 0.000 claims 1
- QIPODOWWZRVEKL-SFHVURJKSA-N [(3s)-1-(4-imidazol-1-ylphenyl)pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)N2C=NC=C2)CC1 QIPODOWWZRVEKL-SFHVURJKSA-N 0.000 claims 1
- ZYBCHPBYMVPNQH-KRWDZBQOSA-N [(3s)-1-[2-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C(=CC(=CC=2)C=2ON=C(C)N=2)F)CC1 ZYBCHPBYMVPNQH-KRWDZBQOSA-N 0.000 claims 1
- JLXVJQQSMXXOCY-SFHVURJKSA-N [(3s)-1-[3-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=C(C=CC=2)C=2ON=C(C)N=2)CC1 JLXVJQQSMXXOCY-SFHVURJKSA-N 0.000 claims 1
- UYBOKBHVPBWUFH-KRWDZBQOSA-N [(3s)-1-[3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)[C@@H]1CN(C=2C=C(F)C(C=3ON=C(C)N=3)=CC=2)CC1 UYBOKBHVPBWUFH-KRWDZBQOSA-N 0.000 claims 1
- CBCAEUGHISGMJQ-INIZCTEOSA-N [(3s)-1-[3-fluoro-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=C(F)C(C=3ON=C(C)N=3)=CC=2)CC1 CBCAEUGHISGMJQ-INIZCTEOSA-N 0.000 claims 1
- VBSGTTPSUKPZJQ-SFHVURJKSA-N [(3s)-1-[4-(1,2-oxazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2ON=CC=2)CC1 VBSGTTPSUKPZJQ-SFHVURJKSA-N 0.000 claims 1
- BKPMNQNQXRJZKV-SFHVURJKSA-N [(3s)-1-[4-(1,3-oxazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2OC=NC=2)CC1 BKPMNQNQXRJZKV-SFHVURJKSA-N 0.000 claims 1
- VGBIKTCJQQKEFX-IBGZPJMESA-N [(3s)-1-[4-(2-methyl-1,3-oxazol-4-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2N=C(C)OC=2)CC1 VGBIKTCJQQKEFX-IBGZPJMESA-N 0.000 claims 1
- UBRPQLXMDZVHCP-IBGZPJMESA-N [(3s)-1-[4-(2-methyl-1,3-oxazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2OC(C)=NC=2)CC1 UBRPQLXMDZVHCP-IBGZPJMESA-N 0.000 claims 1
- PCEWCRUEPDUGSU-IBGZPJMESA-N [(3s)-1-[4-(2-methylimidazol-1-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)N2C(=NC=C2)C)CC1 PCEWCRUEPDUGSU-IBGZPJMESA-N 0.000 claims 1
- YYNFVEZVQLHDGC-IBGZPJMESA-N [(3s)-1-[4-(3-ethyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound CCC1=NOC(C=2C=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CCC2)C(C)C)=N1 YYNFVEZVQLHDGC-IBGZPJMESA-N 0.000 claims 1
- PATUCRXRMASYJU-IBGZPJMESA-N [(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-pentan-3-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(CC)CC)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 PATUCRXRMASYJU-IBGZPJMESA-N 0.000 claims 1
- WHCWUQZKDPMIGH-IBGZPJMESA-N [(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 WHCWUQZKDPMIGH-IBGZPJMESA-N 0.000 claims 1
- QBJWLJXVGOFHFX-SFHVURJKSA-N [(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 QBJWLJXVGOFHFX-SFHVURJKSA-N 0.000 claims 1
- CQFSDSNLSQURSR-LPHOPBHVSA-N [(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]-[(3s)-3-methyl-4-propan-2-ylpiperazin-1-yl]methanone Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 CQFSDSNLSQURSR-LPHOPBHVSA-N 0.000 claims 1
- PXVPPTFSYIKJBE-IBGZPJMESA-N [(3s)-1-[4-(4-methylimidazol-1-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)N2C=C(C)N=C2)CC1 PXVPPTFSYIKJBE-IBGZPJMESA-N 0.000 claims 1
- NIXPOQHPJVUNEI-SFHVURJKSA-N [(3s)-1-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2N=C(C)ON=2)CC1 NIXPOQHPJVUNEI-SFHVURJKSA-N 0.000 claims 1
- AWSWXQJSGZQQOU-IBGZPJMESA-N [(3s)-1-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2OC(C)=NN=2)CC1 AWSWXQJSGZQQOU-IBGZPJMESA-N 0.000 claims 1
- RHMDXLFQFOBXOH-SFHVURJKSA-N [(3s)-1-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2OC(C)=NN=2)CC1 RHMDXLFQFOBXOH-SFHVURJKSA-N 0.000 claims 1
- IGSLFRDFOPKRTK-QFIPXVFZSA-N [(3s)-1-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=CC(=CC=2)C=2OC(=NN=2)C=2C=CC=CC=2)CC1 IGSLFRDFOPKRTK-QFIPXVFZSA-N 0.000 claims 1
- OJDIWUZFITXDRO-INIZCTEOSA-N [(3s)-1-[6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridin-3-yl]pyrrolidin-3-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=NC(=CC=2)C=2ON=C(C)N=2)CC1 OJDIWUZFITXDRO-INIZCTEOSA-N 0.000 claims 1
- MSKUPINGSAZGTP-GJZGRUSLSA-N [(3s)-3-methyl-4-propan-2-ylpiperazin-1-yl]-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1[C@H](C)N(C(C)C)CCN1C(=O)[C@@H]1CN(C=2C=NC(=CC=2)C(F)(F)F)CC1 MSKUPINGSAZGTP-GJZGRUSLSA-N 0.000 claims 1
- QPDUYTMJXPZQDA-FQEVSTJZSA-N [4-(cyclopropylmethyl)-1,4-diazepan-1-yl]-[(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC3CC3)CCC2)=N1 QPDUYTMJXPZQDA-FQEVSTJZSA-N 0.000 claims 1
- HTSWAPRVWBKBGO-SFHVURJKSA-N [4-(cyclopropylmethyl)-1,4-diazepan-1-yl]-[(3s)-1-[6-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound O1C(C)=NC(C=2N=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC3CC3)CCC2)=N1 HTSWAPRVWBKBGO-SFHVURJKSA-N 0.000 claims 1
- LXKMZMNNAKJQFD-IBGZPJMESA-N [4-(cyclopropylmethyl)piperazin-1-yl]-[(3s)-1-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]pyrrolidin-3-yl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC3CC3)CC2)=N1 LXKMZMNNAKJQFD-IBGZPJMESA-N 0.000 claims 1
- QEZZAHLGBVDWNB-KRWDZBQOSA-N [4-(cyclopropylmethyl)piperazin-1-yl]-[(3s)-1-[6-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound O1C(C)=NC(C=2N=CC(=CC=2)N2C[C@H](CC2)C(=O)N2CCN(CC3CC3)CC2)=N1 QEZZAHLGBVDWNB-KRWDZBQOSA-N 0.000 claims 1
- GKAQOFAZTNGKLA-HNNXBMFYSA-N [4-(cyclopropylmethyl)piperazin-1-yl]-[(3s)-1-[6-(trifluoromethyl)pyridin-3-yl]pyrrolidin-3-yl]methanone Chemical compound C1=NC(C(F)(F)F)=CC=C1N1C[C@@H](C(=O)N2CCN(CC3CC3)CC2)CC1 GKAQOFAZTNGKLA-HNNXBMFYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000003435 aroyl group Chemical group 0.000 claims 1
- 125000005533 aryl carboxamido group Chemical group 0.000 claims 1
- 125000005421 aryl sulfonamido group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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| GB0508441A GB0508441D0 (en) | 2004-10-15 | 2005-04-26 | Novel compounds |
| PCT/EP2005/011371 WO2006040192A1 (en) | 2004-10-15 | 2005-10-13 | Pyrrolidine derivatives as histamine receptors ligands |
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| JP2008516922A JP2008516922A (ja) | 2008-05-22 |
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| GB0324159D0 (en) | 2003-10-15 | 2003-11-19 | Glaxo Group Ltd | Novel compounds |
| KR20090024811A (ko) | 2006-06-23 | 2009-03-09 | 아보트 러보러터리즈 | 히스타민 ｈ3 수용체 조절제로서의 사이클로프로필 아민 유도체 |
| US9108948B2 (en) | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
| TW200902007A (en) * | 2007-05-25 | 2009-01-16 | Astrazeneca Ab | Spirocyclopropyl piperidine derivatives |
| TWI432422B (zh) | 2007-08-22 | 2014-04-01 | Astrazeneca Ab | 環丙基醯胺衍生物 |
| ATE554081T1 (de) | 2007-09-06 | 2012-05-15 | Glaxo Group Ltd | Piperazinderivate mit affinität zum histamin-h3- rezeptor |
| WO2009103652A1 (en) | 2008-02-22 | 2009-08-27 | F. Hoffmann-La Roche Ag | Modulators for amyloid beta |
| CA2721303C (en) | 2008-05-08 | 2016-06-28 | Evotec Ag | Azetidines and cyclobutanes as histamine h3 receptor antagonists |
| US8236792B2 (en) | 2008-05-23 | 2012-08-07 | Janssen Pharmaceutica Nv | Substituted pyrrolidine amides as modulators of the histamine H3 receptor |
| CN102171206B (zh) * | 2008-08-06 | 2014-06-25 | 辉瑞股份有限公司 | 作为mc4激动剂的二氮杂环庚烷和二氮杂环辛烷 |
| KR101324414B1 (ko) | 2008-10-09 | 2013-11-01 | 에프. 호프만-라 로슈 아게 | 아밀로이드 베타의 조절자 |
| CN102209537A (zh) | 2008-11-10 | 2011-10-05 | 弗·哈夫曼-拉罗切有限公司 | 杂环γ分泌酶调节剂 |
| US20100130477A1 (en) * | 2008-11-25 | 2010-05-27 | Astrazeneca Ab | Spirocyclobutyl Piperidine Derivatives |
| CA2751239C (en) | 2009-02-02 | 2016-11-01 | Adam James Davenport | Azetidines as histamine h3 receptor antagonists |
| TW201039825A (en) | 2009-02-20 | 2010-11-16 | Astrazeneca Ab | Cyclopropyl amide derivatives 983 |
| US9186353B2 (en) | 2009-04-27 | 2015-11-17 | Abbvie Inc. | Treatment of osteoarthritis pain |
| WO2011016559A1 (ja) * | 2009-08-07 | 2011-02-10 | 武田薬品工業株式会社 | 複素環化合物およびその用途 |
| US8486967B2 (en) | 2010-02-17 | 2013-07-16 | Hoffmann-La Roche Inc. | Heteroaryl substituted piperidines |
| SG183274A1 (en) | 2010-02-18 | 2012-09-27 | Astrazeneca Ab | Processes for making cyclopropyl amide derivatives and intermediates associated therewith |
| WO2012037258A1 (en) | 2010-09-16 | 2012-03-22 | Abbott Laboratories | Processes for preparing 1,2-substituted cyclopropyl derivatives |
| WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
| EP2647377A1 (en) | 2012-04-06 | 2013-10-09 | Sanofi | Use of an h3 receptor antagonist for the treatment of alzheimer's disease |
| CN116615417B (zh) * | 2022-03-31 | 2024-05-14 | 广州必贝特医药股份有限公司 | 1,4-二杂环基取代芳环或芳杂环类化合物及其应用 |
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| CZ45699A3 (cs) * | 1996-08-14 | 1999-05-12 | Zeneca Limited | Substituované deriváty pyrimidinu, způsob jejich přípravy a farmaceutický prostředek, který je obsahuje |
| DE10034338C2 (de) * | 2000-07-14 | 2002-06-20 | Forschungszentrum Juelich Gmbh | Mehrpoliges kaskadierendes Quardrupel-Bandpaßfilter auf der Basis dielektrischer Dual-Mode-Resonatoren |
| JPWO2003062234A1 (ja) * | 2002-01-23 | 2005-05-19 | 山之内製薬株式会社 | キノキサリン化合物 |
| WO2004037257A1 (en) * | 2002-10-23 | 2004-05-06 | Janssen Pharmaceutica, N.V. | Phenylpiperidines and phenylpyrrolidines as histamine h3 receptor modulators |
| ES2311152T3 (es) * | 2003-04-23 | 2009-02-01 | Glaxo Group Limited | Derivados de piperazina y su uso para el tratamiento de enfermedades neurologicas y psiquiatricas. |
-
2005
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- 2005-10-13 US US11/576,968 patent/US20080045506A1/en not_active Abandoned
- 2005-10-13 SI SI200530241T patent/SI1802307T1/sl unknown
- 2005-10-13 PT PT05802453T patent/PT1802307E/pt unknown
- 2005-10-13 ES ES05802453T patent/ES2303280T3/es active Active
- 2005-10-13 JP JP2007536122A patent/JP2008516922A/ja not_active Withdrawn
- 2005-10-13 WO PCT/EP2005/011371 patent/WO2006040192A1/en active IP Right Grant
- 2005-10-13 AR ARP050104299A patent/AR051391A1/es unknown
- 2005-10-13 PL PL05802453T patent/PL1802307T3/pl unknown
- 2005-10-13 DE DE602005005080T patent/DE602005005080T2/de active Active
- 2005-10-13 DK DK05802453T patent/DK1802307T3/da active
- 2005-10-13 EP EP05802453A patent/EP1802307B1/en active Active
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2008
- 2008-05-23 HR HR20080227T patent/HRP20080227T3/xx unknown
