JP2007508346A5 - - Google Patents
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- Publication number
- JP2007508346A5 JP2007508346A5 JP2006534702A JP2006534702A JP2007508346A5 JP 2007508346 A5 JP2007508346 A5 JP 2007508346A5 JP 2006534702 A JP2006534702 A JP 2006534702A JP 2006534702 A JP2006534702 A JP 2006534702A JP 2007508346 A5 JP2007508346 A5 JP 2007508346A5
- Authority
- JP
- Japan
- Prior art keywords
- carbonyl
- phenyl
- hexahydro
- diazepine
- cyclobutyl
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- RQROQSWIGRQREC-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[3-(pyridin-3-ylmethoxy)phenyl]methanone Chemical compound C=1C=CC(OCC=2C=NC=CC=2)=CC=1C(=O)N(CC1)CCCN1C1CCC1 RQROQSWIGRQREC-UHFFFAOYSA-N 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 2
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims 2
- -1 cyano, amino Chemical group 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- FPUXOMMOENZXMT-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-(3-pyridin-3-ylphenyl)methanone Chemical compound C=1C=CC(C=2C=NC=CC=2)=CC=1C(=O)N(CC1)CCCN1C1CCC1 FPUXOMMOENZXMT-UHFFFAOYSA-N 0.000 claims 1
- BZKRNBPZMNJJBI-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-(4-morpholin-4-ylphenyl)methanone Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)N(CC1)CCCN1C1CCC1 BZKRNBPZMNJJBI-UHFFFAOYSA-N 0.000 claims 1
- PMPZBNJJRKWLMD-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-(4-phenoxyphenyl)methanone Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1C(=O)N(CC1)CCCN1C1CCC1 PMPZBNJJRKWLMD-UHFFFAOYSA-N 0.000 claims 1
- OIDUQBYXYJCLHO-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-(4-phenylmethoxyphenyl)methanone Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1C(=O)N(CC1)CCCN1C1CCC1 OIDUQBYXYJCLHO-UHFFFAOYSA-N 0.000 claims 1
- XEPGNUBRHNTZRF-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)N(CC1)CCCN1C1CCC1 XEPGNUBRHNTZRF-UHFFFAOYSA-N 0.000 claims 1
- QSRSHKSOCDQOGY-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-(4-pyridin-2-ylphenyl)methanone Chemical compound C=1C=C(C=2N=CC=CC=2)C=CC=1C(=O)N(CC1)CCCN1C1CCC1 QSRSHKSOCDQOGY-UHFFFAOYSA-N 0.000 claims 1
- XONLXWIIRCBHLZ-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-(4-pyridin-3-ylphenyl)methanone Chemical compound C=1C=C(C=2C=NC=CC=2)C=CC=1C(=O)N(CC1)CCCN1C1CCC1 XONLXWIIRCBHLZ-UHFFFAOYSA-N 0.000 claims 1
- KYFGCNDPBDNKDD-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-(4-pyrrol-1-ylphenyl)methanone Chemical compound C=1C=C(N2C=CC=C2)C=CC=1C(=O)N(CC1)CCCN1C1CCC1 KYFGCNDPBDNKDD-UHFFFAOYSA-N 0.000 claims 1
- HVHBLZNPHSYUGL-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[3-(5-methyltetrazol-1-yl)phenyl]methanone Chemical compound CC1=NN=NN1C1=CC=CC(C(=O)N2CCN(CCC2)C2CCC2)=C1 HVHBLZNPHSYUGL-UHFFFAOYSA-N 0.000 claims 1
- BBECLODOGVMYJR-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[3-(phenoxymethyl)phenyl]methanone Chemical compound C=1C=CC(COC=2C=CC=CC=2)=CC=1C(=O)N(CC1)CCCN1C1CCC1 BBECLODOGVMYJR-UHFFFAOYSA-N 0.000 claims 1
- KMCNVCDVXJTDHA-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[4-(1,3-oxazol-2-yl)phenyl]methanone Chemical compound C=1C=C(C=2OC=CN=2)C=CC=1C(=O)N(CC1)CCCN1C1CCC1 KMCNVCDVXJTDHA-UHFFFAOYSA-N 0.000 claims 1
- RTEMEIPKWIOGFT-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[4-(2-ethyltetrazol-5-yl)phenyl]methanone Chemical compound CCN1N=NC(C=2C=CC(=CC=2)C(=O)N2CCN(CCC2)C2CCC2)=N1 RTEMEIPKWIOGFT-UHFFFAOYSA-N 0.000 claims 1
- DTIFVKKOUHVXLE-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]methanone Chemical compound CC1=NOC(C)=C1C1=CC=C(C(=O)N2CCN(CCC2)C2CCC2)C=C1 DTIFVKKOUHVXLE-UHFFFAOYSA-N 0.000 claims 1
- FKTPQBLJSAOFMY-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[4-(3,5-dimethylpyrazol-1-yl)phenyl]methanone Chemical compound N1=C(C)C=C(C)N1C1=CC=C(C(=O)N2CCN(CCC2)C2CCC2)C=C1 FKTPQBLJSAOFMY-UHFFFAOYSA-N 0.000 claims 1
- LSLPVCYRWMWYRY-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[4-(3-fluorophenyl)phenyl]methanone Chemical compound FC1=CC=CC(C=2C=CC(=CC=2)C(=O)N2CCN(CCC2)C2CCC2)=C1 LSLPVCYRWMWYRY-UHFFFAOYSA-N 0.000 claims 1
- IEYAGYVHFOQZKG-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]methanone Chemical compound CC1=NOC(C=2C=CC(=CC=2)C(=O)N2CCN(CCC2)C2CCC2)=N1 IEYAGYVHFOQZKG-UHFFFAOYSA-N 0.000 claims 1
- XQVRCTWGJJTZET-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[4-(phenoxymethyl)phenyl]methanone Chemical compound C=1C=C(COC=2C=CC=CC=2)C=CC=1C(=O)N(CC1)CCCN1C1CCC1 XQVRCTWGJJTZET-UHFFFAOYSA-N 0.000 claims 1
- CIHFNQDXJHSSTN-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[4-[(3,5-dimethylpyrazol-1-yl)methyl]phenyl]methanone Chemical compound N1=C(C)C=C(C)N1CC1=CC=C(C(=O)N2CCN(CCC2)C2CCC2)C=C1 CIHFNQDXJHSSTN-UHFFFAOYSA-N 0.000 claims 1
- SVJITYVOQSNAFT-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[4-[(4,6-dimethylpyrimidin-2-yl)-methylamino]phenyl]methanone Chemical compound N=1C(C)=CC(C)=NC=1N(C)C(C=C1)=CC=C1C(=O)N(CC1)CCCN1C1CCC1 SVJITYVOQSNAFT-UHFFFAOYSA-N 0.000 claims 1
- KCPHUDZBVQVVLT-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[4-[2-(trifluoromethyl)pyrimidin-5-yl]phenyl]methanone Chemical compound C1=NC(C(F)(F)F)=NC=C1C1=CC=C(C(=O)N2CCN(CCC2)C2CCC2)C=C1 KCPHUDZBVQVVLT-UHFFFAOYSA-N 0.000 claims 1
- MTDHAGZLBHZFAP-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[4-[4-(1,3-oxazol-2-yl)phenyl]phenyl]methanone Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2OC=CN=2)C=CC=1C(=O)N(CC1)CCCN1C1CCC1 MTDHAGZLBHZFAP-UHFFFAOYSA-N 0.000 claims 1
- ZNQKXCWEJJCXGD-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[4-[4-(2-methyl-1,3-oxazol-4-yl)phenyl]phenyl]methanone Chemical compound O1C(C)=NC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(=O)N2CCN(CCC2)C2CCC2)=C1 ZNQKXCWEJJCXGD-UHFFFAOYSA-N 0.000 claims 1
- LKCRYMKCNMMDHB-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[4-[4-(2-methyl-1,3-oxazol-5-yl)phenyl]phenyl]methanone Chemical compound O1C(C)=NC=C1C1=CC=C(C=2C=CC(=CC=2)C(=O)N2CCN(CCC2)C2CCC2)C=C1 LKCRYMKCNMMDHB-UHFFFAOYSA-N 0.000 claims 1
- HRHLENJBCHBHFF-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[4-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]phenyl]methanone Chemical compound C1=CC(F)=CC=C1C1=CSC(C=2C=CC(=CC=2)C(=O)N2CCN(CCC2)C2CCC2)=N1 HRHLENJBCHBHFF-UHFFFAOYSA-N 0.000 claims 1
- KZGNUNFTGXFPOG-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[4-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methanone Chemical compound O1C(C)=NC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(=O)N2CCN(CCC2)C2CCC2)=N1 KZGNUNFTGXFPOG-UHFFFAOYSA-N 0.000 claims 1
- WDASDDVHGZERNC-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[4-[6-(trifluoromethyl)pyridazin-3-yl]phenyl]methanone Chemical compound N1=NC(C(F)(F)F)=CC=C1C1=CC=C(C(=O)N2CCN(CCC2)C2CCC2)C=C1 WDASDDVHGZERNC-UHFFFAOYSA-N 0.000 claims 1
- MHGFZISBDBMAMB-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[4-[6-(trifluoromethyl)pyridin-3-yl]phenyl]methanone Chemical compound C1=NC(C(F)(F)F)=CC=C1C1=CC=C(C(=O)N2CCN(CCC2)C2CCC2)C=C1 MHGFZISBDBMAMB-UHFFFAOYSA-N 0.000 claims 1
- GPSIIZJAYULCJO-UHFFFAOYSA-N (4-morpholin-4-ylphenyl)-(4-propan-2-yl-1,4-diazepan-1-yl)methanone;hydrochloride Chemical compound Cl.C1CN(C(C)C)CCCN1C(=O)C1=CC=C(N2CCOCC2)C=C1 GPSIIZJAYULCJO-UHFFFAOYSA-N 0.000 claims 1
- CKJASYAXFPFUNO-UHFFFAOYSA-N (4-propan-2-yl-1,4-diazepan-1-yl)-[4-[2-(trifluoromethyl)pyrimidin-5-yl]phenyl]methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C1=CC=C(C=2C=NC(=NC=2)C(F)(F)F)C=C1 CKJASYAXFPFUNO-UHFFFAOYSA-N 0.000 claims 1
- VIKMVZVDXSBATE-UHFFFAOYSA-N (4-propan-2-yl-1,4-diazepan-1-yl)-[4-[6-(trifluoromethyl)pyridazin-3-yl]phenyl]methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C1=CC=C(C=2N=NC(=CC=2)C(F)(F)F)C=C1 VIKMVZVDXSBATE-UHFFFAOYSA-N 0.000 claims 1
- DLDYLSBACBWVBC-UHFFFAOYSA-N (4-propan-2-yl-1,4-diazepan-1-yl)-[4-[6-(trifluoromethyl)pyridin-3-yl]phenyl]methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C1=CC=C(C=2C=NC(=CC=2)C(F)(F)F)C=C1 DLDYLSBACBWVBC-UHFFFAOYSA-N 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 1
- ZJNDRXHOJJOCCI-UHFFFAOYSA-N 1-[3-(4-cyclobutyl-1,4-diazepane-1-carbonyl)phenyl]pyrrolidin-2-one Chemical compound C=1C=CC(N2C(CCC2)=O)=CC=1C(=O)N(CC1)CCCN1C1CCC1 ZJNDRXHOJJOCCI-UHFFFAOYSA-N 0.000 claims 1
- CGFJIRFOAXJNOG-UHFFFAOYSA-N 1-[4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)phenyl]-3-(trifluoromethyl)pyrazole-4-carbonitrile Chemical compound C1=C(C#N)C(C(F)(F)F)=NN1C1=CC=C(C(=O)N2CCN(CCC2)C2CCC2)C=C1 CGFJIRFOAXJNOG-UHFFFAOYSA-N 0.000 claims 1
- HBWVPHIWXGMMDG-UHFFFAOYSA-N 1-[4-[4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)phenyl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=C(C(=O)N2CCN(CCC2)C2CCC2)C=C1 HBWVPHIWXGMMDG-UHFFFAOYSA-N 0.000 claims 1
- BTIOTMDCPDYUAF-UHFFFAOYSA-N 1-[[4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)phenyl]methyl]-5-(trifluoromethyl)pyridin-2-one Chemical compound C1=C(C(F)(F)F)C=CC(=O)N1CC1=CC=C(C(=O)N2CCN(CCC2)C2CCC2)C=C1 BTIOTMDCPDYUAF-UHFFFAOYSA-N 0.000 claims 1
- OKQHGVBTWNZZHM-UHFFFAOYSA-N 3-[4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)phenyl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2C=CC(=CC=2)C(=O)N2CCN(CCC2)C2CCC2)=C1 OKQHGVBTWNZZHM-UHFFFAOYSA-N 0.000 claims 1
- OXTCUCZPGBBGME-UHFFFAOYSA-N 4-[4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)phenoxy]benzonitrile Chemical compound C=1C=C(OC=2C=CC(=CC=2)C#N)C=CC=1C(=O)N(CC1)CCCN1C1CCC1 OXTCUCZPGBBGME-UHFFFAOYSA-N 0.000 claims 1
- YRKIKNDFQBHOES-UHFFFAOYSA-N 4-[4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)phenyl]benzonitrile Chemical compound C=1C=C(C=2C=CC(=CC=2)C#N)C=CC=1C(=O)N(CC1)CCCN1C1CCC1 YRKIKNDFQBHOES-UHFFFAOYSA-N 0.000 claims 1
- GFJXBFFYRKUOCH-UHFFFAOYSA-N 4-[4-(4-propan-2-yl-1,4-diazepane-1-carbonyl)phenyl]benzonitrile Chemical compound C1CN(C(C)C)CCCN1C(=O)C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 GFJXBFFYRKUOCH-UHFFFAOYSA-N 0.000 claims 1
- MYJRNFFIIHYURY-UHFFFAOYSA-N 5-[4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)phenyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1C1=CC=C(C(=O)N2CCN(CCC2)C2CCC2)C=C1 MYJRNFFIIHYURY-UHFFFAOYSA-N 0.000 claims 1
- YGZIQPLNDAWBOR-UHFFFAOYSA-N 5-[4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)phenyl]pyridine-2-carbonitrile Chemical compound C=1C=C(C=2C=NC(=CC=2)C#N)C=CC=1C(=O)N(CC1)CCCN1C1CCC1 YGZIQPLNDAWBOR-UHFFFAOYSA-N 0.000 claims 1
- QESQSMDDMVDZAF-UHFFFAOYSA-N 5-[4-(4-propan-2-yl-1,4-diazepane-1-carbonyl)phenyl]pyridine-2-carbonitrile Chemical compound C1CN(C(C)C)CCCN1C(=O)C1=CC=C(C=2C=NC(=CC=2)C#N)C=C1 QESQSMDDMVDZAF-UHFFFAOYSA-N 0.000 claims 1
- IOGSJLWEGUOLDI-UHFFFAOYSA-N 6-[4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)phenyl]pyridine-3-carbonitrile Chemical compound C=1C=C(C=2N=CC(=CC=2)C#N)C=CC=1C(=O)N(CC1)CCCN1C1CCC1 IOGSJLWEGUOLDI-UHFFFAOYSA-N 0.000 claims 1
- NSWLSONUCPBZHX-UHFFFAOYSA-N 6-[4-(4-propan-2-yl-1,4-diazepane-1-carbonyl)phenyl]pyridine-3-carbonitrile Chemical compound C1CN(C(C)C)CCCN1C(=O)C1=CC=C(C=2N=CC(=CC=2)C#N)C=C1 NSWLSONUCPBZHX-UHFFFAOYSA-N 0.000 claims 1
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- XQXQNYYRANCNTF-UHFFFAOYSA-N [4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C1=CC=C(C2=C(ON=C2C)C)C=C1 XQXQNYYRANCNTF-UHFFFAOYSA-N 0.000 claims 1
- YXKPSTCSWRENIQ-UHFFFAOYSA-N [4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C1=CC=C(C=2ON=C(C)N=2)C=C1 YXKPSTCSWRENIQ-UHFFFAOYSA-N 0.000 claims 1
- DWLJHBKCOSJSBJ-UHFFFAOYSA-N [4-(4-cyclobutyl-1,4-diazepane-1-carbonyl)phenyl]-phenylmethanone Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1C(=O)N(CC1)CCCN1C1CCC1 DWLJHBKCOSJSBJ-UHFFFAOYSA-N 0.000 claims 1
- MWVKAAYXRMMBQL-UHFFFAOYSA-N [4-(oxan-4-yloxy)phenyl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C(C=C1)=CC=C1OC1CCOCC1 MWVKAAYXRMMBQL-UHFFFAOYSA-N 0.000 claims 1
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims 1
- 125000003435 aroyl group Chemical group 0.000 claims 1
- 125000005141 aryl amino 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
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- CHHZAHYDMOFGKL-UHFFFAOYSA-N n,n-dimethyl-5-[4-(4-propan-2-yl-1,4-diazepane-1-carbonyl)phenyl]pyridine-2-carboxamide Chemical compound C1CN(C(C)C)CCCN1C(=O)C1=CC=C(C=2C=NC(=CC=2)C(=O)N(C)C)C=C1 CHHZAHYDMOFGKL-UHFFFAOYSA-N 0.000 claims 1
- DDEUUIOCEWONSZ-UHFFFAOYSA-N n-[3-(4-cyclobutyl-1,4-diazepane-1-carbonyl)phenyl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC(C=1)=CC=CC=1C(=O)N(CC1)CCCN1C1CCC1 DDEUUIOCEWONSZ-UHFFFAOYSA-N 0.000 claims 1
- MWDIUSYVDQJXIC-UHFFFAOYSA-N n-[3-(4-cyclobutyl-1,4-diazepane-1-carbonyl)phenyl]pyridine-4-carboxamide Chemical compound C=1C=NC=CC=1C(=O)NC(C=1)=CC=CC=1C(=O)N(CC1)CCCN1C1CCC1 MWDIUSYVDQJXIC-UHFFFAOYSA-N 0.000 claims 1
- MMYWYXOIXGDCPX-UHFFFAOYSA-N n-methyl-5-[4-(4-propan-2-yl-1,4-diazepane-1-carbonyl)phenyl]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1C1=CC=C(C(=O)N2CCN(CCC2)C(C)C)C=C1 MMYWYXOIXGDCPX-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0324159.3 | 2003-10-15 | ||
| GBGB0324159.3A GB0324159D0 (en) | 2003-10-15 | 2003-10-15 | Novel compounds |
| PCT/EP2004/011619 WO2005040144A1 (en) | 2003-10-15 | 2004-10-14 | Novel compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007508346A JP2007508346A (ja) | 2007-04-05 |
| JP2007508346A5 true JP2007508346A5 (Direct) | 2007-11-22 |
| JP4824567B2 JP4824567B2 (ja) | 2011-11-30 |
Family
ID=29559346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006534702A Expired - Fee Related JP4824567B2 (ja) | 2003-10-15 | 2004-10-14 | 新規化合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US7846922B2 (Direct) |
| EP (1) | EP1675838A1 (Direct) |
| JP (1) | JP4824567B2 (Direct) |
| GB (1) | GB0324159D0 (Direct) |
| WO (1) | WO2005040144A1 (Direct) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE449766T1 (de) | 2002-10-23 | 2009-12-15 | Janssen Pharmaceutica Nv | Piperazinyl- und diazapanylbenzamide und- benzothioamide |
| GB0324159D0 (en) | 2003-10-15 | 2003-11-19 | Glaxo Group Ltd | Novel compounds |
| CN1972914A (zh) | 2004-03-31 | 2007-05-30 | 詹森药业有限公司 | 作为组胺h3受体配合体的非咪唑杂环化合物 |
| WO2007044085A2 (en) * | 2005-05-19 | 2007-04-19 | Xenon Pharmaceuticals Inc. | Heteroaryl compounds and their uses as therapeutic agents |
| PT1948607E (pt) | 2005-09-16 | 2010-06-02 | Janssen Pharmaceutica Nv | Ciclopropilaminas como moduladores do receptor h3 de histamina |
| WO2007043400A1 (ja) * | 2005-10-07 | 2007-04-19 | Kissei Pharmaceutical Co., Ltd. | 含窒素芳香族複素環化合物およびそれを含有する医薬組成物 |
| NZ573028A (en) * | 2006-05-30 | 2011-11-25 | Janssen Pharmaceutica Nv | Substituted pyridyl amide compounds as modulators of the histamine h3 receptor |
| CN101511775A (zh) | 2006-06-29 | 2009-08-19 | 詹森药业有限公司 | 丁基和丁炔基苄基胺化合物 |
| WO2008002816A1 (en) * | 2006-06-29 | 2008-01-03 | Janssen Pharmaceutica N.V. | Substituted benzamide modulators of the histamine h3 receptor |
| CA2656089A1 (en) | 2006-06-29 | 2008-01-03 | Janssen Pharmaceutica N.V. | Substituted benzyl amine compounds |
| GB0617575D0 (en) * | 2006-09-06 | 2006-10-18 | Syngenta Ltd | Herbicidal compounds and compositions |
| PL2121636T3 (pl) * | 2006-12-14 | 2017-09-29 | Janssen Pharmaceutica N.V. | Sposób wytwarzania piperazynylowych i diazepanylowych pochodnych benzamidu |
| MX2009010491A (es) | 2007-04-11 | 2009-11-09 | Kissei Pharmaceutical | Derivado heterociclico de 5 miembros y su uso para propositos medicos. |
| US8853392B2 (en) | 2007-06-03 | 2014-10-07 | Vanderbilt University | Benzamide mGluR5 positive allosteric modulators and methods of making and using same |
| SG185285A1 (en) * | 2007-06-03 | 2012-11-29 | Univ Vanderbilt | Benzamide mglur5 positive allosteric modulators and methods of making and using same |
| HUE027022T2 (en) | 2007-08-13 | 2016-08-29 | Monsanto Technology Llc | Preparations and procedures for controlling nematodes |
| ES2748599T3 (es) | 2007-08-27 | 2020-03-17 | Dart Neuroscience Cayman Ltd | Compuestos terapéuticos de isoxazol |
| AU2008294708B2 (en) * | 2007-09-06 | 2012-03-15 | Glaxo Group Limited | Piperazine derivative having affinity for the histamine H3 receptor |
| WO2009067406A1 (en) * | 2007-11-20 | 2009-05-28 | Janssen Pharmaceutica N.V. | Substituted pyridyl amide compounds as modulators of the histamine h3 receptor |
| WO2009067401A1 (en) * | 2007-11-20 | 2009-05-28 | Janssen Pharmaceutica N.V. | Cycloalkyloxy-and hetξrocycloalky- loxypyridine compounds as modulators of the histamine h3 receptor |
| WO2009102893A2 (en) | 2008-02-14 | 2009-08-20 | Amira Pharmaceuticals, Inc. | CYCLIC DIARYL ETHER COMPOUNDS AS ANTAGONISTS OF PROSTAGLANDIN D2 receptors |
| US8426449B2 (en) | 2008-04-02 | 2013-04-23 | Panmira Pharmaceuticals, Llc | Aminoalkylphenyl antagonists of prostaglandin D2 receptors |
| CN112079769A (zh) | 2008-04-23 | 2020-12-15 | 里格尔药品股份有限公司 | 用于治疗代谢障碍的甲酰胺化合物 |
| US8236792B2 (en) | 2008-05-23 | 2012-08-07 | Janssen Pharmaceutica Nv | Substituted pyrrolidine amides as modulators of the histamine H3 receptor |
| EP2326642A2 (en) * | 2008-08-15 | 2011-06-01 | Glaxo Group Limited | Salt of, and processes for the preparation of, 1-isopropyl-4-{[4-(tetrahydro-2h-pyran- 4-yloxy)phenyl]carbonyl}hexahydro-1h-1,4-diazepine |
| US20110189280A1 (en) * | 2008-08-29 | 2011-08-04 | Allan James Clarke | Dosage form comprising 1-isopropyl-4-hexahydro-1h-1,4-diazepine or a salt thereof |
| WO2010057118A2 (en) | 2008-11-17 | 2010-05-20 | Amira Pharmaceuticals, Inc. | Heterocyclic antagonists of prostaglandin d2 receptors |
| WO2010093425A1 (en) | 2009-02-11 | 2010-08-19 | Sepracor Inc. | Histamine h3 inverse agonists and antagonists and methods of use thereof |
| JP5722883B2 (ja) * | 2009-05-25 | 2015-05-27 | 中南大学Ｃｅｎｔｒａｌ Ｓｏｕｔｈ Ｕｎｉｖｅｒｓｉｔｙ | １−（置換ベンジル）−５−トリフルオロメチル−２−（１ｈ）ピリドン化合物及びその塩、並びにその製造方法及びその用途 |
| 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 |
| JO3407B1 (ar) | 2012-05-31 | 2019-10-20 | Eisai R&D Man Co Ltd | مركبات رباعي هيدرو بيرازولو بيريميدين |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU6179998A (en) | 1997-02-24 | 1998-09-09 | Zymogenetics Inc. | Calcitonin mimetics |
| US6268367B1 (en) | 1998-02-23 | 2001-07-31 | Zymogenetics, Inc. | Piperazine derivatives for treating bone deficit conditions |
| WO2002008221A2 (en) | 2000-07-20 | 2002-01-31 | Neurogen Corporation | Capsaicin receptor ligands |
| ATE354568T1 (de) * | 2000-08-08 | 2007-03-15 | Ortho Mcneil Pharm Inc | Nicht-imidazol aryloxypiperidine als h3 rezeptor liganden |
| DE60234453D1 (de) | 2001-07-02 | 2009-12-31 | High Point Pharmaceuticals Llc | Substituierte piperazin- und diazepanderivate zur verwendung als histamin h3 rezeptormodulatoren |
| DE10144226A1 (de) * | 2001-09-07 | 2003-03-27 | Henkel Kgaa | Neue verbrückte p-Phenylendiamine |
| IL160915A0 (en) * | 2001-09-19 | 2004-08-31 | Aventis Pharma Sa | Indolizines inhibiting kinase proteins |
| IL162859A0 (en) * | 2002-02-05 | 2005-11-20 | Novo Nordisk As | Novel aryl-and heteroarylpiperazines |
| GB0224084D0 (en) * | 2002-10-16 | 2002-11-27 | Glaxo Group Ltd | Novel compounds |
| AU2003274053A1 (en) | 2002-10-22 | 2004-05-13 | Glaxo Group Limited | Aryloxyalkylamine derivates as h3 receptor ligands |
| ATE449766T1 (de) | 2002-10-23 | 2009-12-15 | Janssen Pharmaceutica Nv | Piperazinyl- und diazapanylbenzamide und- benzothioamide |
| US7449464B2 (en) * | 2003-03-12 | 2008-11-11 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
| KR101146806B1 (ko) | 2003-03-12 | 2012-05-22 | 메이브릿지 리미티드 | 프탈라지논 유도체 |
| EP1615909B1 (en) | 2003-04-23 | 2008-07-23 | Glaxo Group Limited | Piperazine derivatives and their use for the treatment of neurological and psychiatric diseases |
| GB0324159D0 (en) | 2003-10-15 | 2003-11-19 | Glaxo Group Ltd | Novel compounds |
| HRP20080227T3 (hr) | 2004-10-15 | 2008-06-30 | Glaxo Group Limited | Pirolidinski derivati kao ligandi histaminskih receptora |
| JP5185822B2 (ja) | 2005-10-31 | 2013-04-17 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | シクロプロピル−アミド誘導体の製造方法 |
| WO2007053427A2 (en) | 2005-10-31 | 2007-05-10 | Janssen Pharmaceutica N.V. | Novel processes for the preparation of piperazinyl and diazapanyl benzamide derivatives |
| PL2121636T3 (pl) | 2006-12-14 | 2017-09-29 | Janssen Pharmaceutica N.V. | Sposób wytwarzania piperazynylowych i diazepanylowych pochodnych benzamidu |
| NZ584100A (en) | 2007-08-22 | 2011-07-29 | Astrazeneca Ab | Cyclopropyl amide derivatives |
| AU2008294708B2 (en) | 2007-09-06 | 2012-03-15 | Glaxo Group Limited | Piperazine derivative having affinity for the histamine H3 receptor |
| WO2009067401A1 (en) | 2007-11-20 | 2009-05-28 | Janssen Pharmaceutica N.V. | Cycloalkyloxy-and hetξrocycloalky- loxypyridine compounds as modulators of the histamine h3 receptor |
-
2003
- 2003-10-15 GB GBGB0324159.3A patent/GB0324159D0/en not_active Ceased
-
2004
- 2004-10-14 EP EP04765973A patent/EP1675838A1/en not_active Withdrawn
- 2004-10-14 JP JP2006534702A patent/JP4824567B2/ja not_active Expired - Fee Related
- 2004-10-14 US US10/576,492 patent/US7846922B2/en not_active Expired - Fee Related
- 2004-10-14 WO PCT/EP2004/011619 patent/WO2005040144A1/en not_active Ceased
-
2010
- 2010-10-26 US US12/912,026 patent/US8492375B2/en not_active Expired - Fee Related
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