JP2005506308A5 - - Google Patents
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- JP2005506308A5 JP2005506308A5 JP2002587412A JP2002587412A JP2005506308A5 JP 2005506308 A5 JP2005506308 A5 JP 2005506308A5 JP 2002587412 A JP2002587412 A JP 2002587412A JP 2002587412 A JP2002587412 A JP 2002587412A JP 2005506308 A5 JP2005506308 A5 JP 2005506308A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- thio
- hydroxy
- pyridinecarbonitrile
- phenylbutyl
- 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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- 150000001875 compounds Chemical class 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 208000027866 inflammatory disease Diseases 0.000 claims description 9
- 102000008299 Nitric Oxide Synthase Human genes 0.000 claims description 4
- 108010021487 Nitric Oxide Synthase Proteins 0.000 claims description 4
- 102000011779 Nitric Oxide Synthase Type II Human genes 0.000 claims description 3
- 108010076864 Nitric Oxide Synthase Type II Proteins 0.000 claims description 3
- 229940111134 coxibs Drugs 0.000 claims description 3
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 9
- -1 2,5-dichloro-4-pyridinyl Chemical group 0.000 claims 9
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 230000009286 beneficial effect Effects 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 230000005764 inhibitory process Effects 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- WBTLPHUUSKWCTK-DZGCQCFKSA-N 3-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-5-(trifluoromethyl)pyridine-2-carbonitrile Chemical compound S([C@H](C[C@@H](CO)N)C=1C=CC=CC=1)C1=CC(C(F)(F)F)=CN=C1C#N WBTLPHUUSKWCTK-DZGCQCFKSA-N 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- DZKGJHSKWJZMKA-JKSUJKDBSA-N (2s,4r)-2-amino-4-[3-(hydroxymethyl)-6-methylpyridin-2-yl]sulfanyl-4-phenylbutan-1-ol Chemical compound CC1=CC=C(CO)C(S[C@H](C[C@H](N)CO)C=2C=CC=CC=2)=N1 DZKGJHSKWJZMKA-JKSUJKDBSA-N 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- KTCXAQJLADLIEB-HZPDHXFCSA-N 2-[(1r,3r)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-6-methylpyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C(S[C@H](C[C@@H](N)CO)C=2C=CC=CC=2)=N1 KTCXAQJLADLIEB-HZPDHXFCSA-N 0.000 claims 1
- PPVNUAINRGSVDA-QPUJVOFHSA-N 2-[(1r,3s)-3-amino-1-(4-chloro-1,3-thiazol-5-yl)-4-hydroxybutoxy]-4-chloro-5-fluorobenzonitrile Chemical compound O([C@H](C[C@@H](CO)N)C1=C(N=CS1)Cl)C1=CC(Cl)=C(F)C=C1C#N PPVNUAINRGSVDA-QPUJVOFHSA-N 0.000 claims 1
- HVLBEQDHPJZZRP-UONOGXRCSA-N 2-[(1r,3s)-3-amino-1-(4-fluorophenyl)-4-hydroxybutoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound O([C@H](C[C@@H](CO)N)C=1C=CC(F)=CC=1)C1=NC(C(F)(F)F)=CC=C1C#N HVLBEQDHPJZZRP-UONOGXRCSA-N 0.000 claims 1
- KZOCZQMORLYGFZ-TVQRCGJNSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-(1,2-thiazol-5-yl)butoxy]-4-chloro-5-fluorobenzonitrile Chemical compound O([C@H](C[C@@H](CO)N)C=1SN=CC=1)C1=CC(Cl)=C(F)C=C1C#N KZOCZQMORLYGFZ-TVQRCGJNSA-N 0.000 claims 1
- ONGOESXEPJCYAM-TVQRCGJNSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-(1,3-thiazol-2-yl)butoxy]-4-chloro-5-fluorobenzonitrile Chemical compound O([C@H](C[C@@H](CO)N)C=1SC=CN=1)C1=CC(Cl)=C(F)C=C1C#N ONGOESXEPJCYAM-TVQRCGJNSA-N 0.000 claims 1
- OMQWQAVAKZMTHQ-CMPLNLGQSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-(1,3-thiazol-2-yl)butoxy]-5-fluoro-6-methylpyridine-3-carbonitrile Chemical compound C1=C(F)C(C)=NC(O[C@H](C[C@H](N)CO)C=2SC=CN=2)=C1C#N OMQWQAVAKZMTHQ-CMPLNLGQSA-N 0.000 claims 1
- FSZJTFHOFVLERS-WCQYABFASA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-(1,3-thiazol-5-yl)butoxy]-5-fluorobenzonitrile Chemical compound O([C@H](C[C@@H](CO)N)C=1SC=NC=1)C1=CC=C(F)C=C1C#N FSZJTFHOFVLERS-WCQYABFASA-N 0.000 claims 1
- APRAUXWKWRYFDN-DOTOQJQBSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-5-bromobenzonitrile Chemical compound S([C@H](C[C@@H](CO)N)C=1C=CC=CC=1)C1=CC=C(Br)C=C1C#N APRAUXWKWRYFDN-DOTOQJQBSA-N 0.000 claims 1
- LYJATWWFPYIMQB-LSDHHAIUSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-5-chloropyridine-3-carbonitrile Chemical compound S([C@H](C[C@@H](CO)N)C=1C=CC=CC=1)C1=NC=C(Cl)C=C1C#N LYJATWWFPYIMQB-LSDHHAIUSA-N 0.000 claims 1
- ZNOLEGFDZRTGIO-DZGCQCFKSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-5-fluoro-6-methoxypyridine-3-carbonitrile Chemical compound C1=C(F)C(OC)=NC(S[C@H](C[C@H](N)CO)C=2C=CC=CC=2)=C1C#N ZNOLEGFDZRTGIO-DZGCQCFKSA-N 0.000 claims 1
- OSCAJWAGCDFVCC-WMLDXEAASA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-5-nitrobenzonitrile Chemical compound S([C@H](C[C@@H](CO)N)C=1C=CC=CC=1)C1=CC=C([N+]([O-])=O)C=C1C#N OSCAJWAGCDFVCC-WMLDXEAASA-N 0.000 claims 1
- QBQSHSWNVAQDES-DZGCQCFKSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-6-(difluoromethyl)pyridine-3-carbonitrile Chemical compound S([C@H](C[C@@H](CO)N)C=1C=CC=CC=1)C1=NC(C(F)F)=CC=C1C#N QBQSHSWNVAQDES-DZGCQCFKSA-N 0.000 claims 1
- KRJUVNKYSHMASM-GOEBONIOSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-6-(fluoromethyl)pyridine-3-carbonitrile Chemical compound S([C@H](C[C@@H](CO)N)C=1C=CC=CC=1)C1=NC(CF)=CC=C1C#N KRJUVNKYSHMASM-GOEBONIOSA-N 0.000 claims 1
- HTLOLXYEAIIKAX-GOEBONIOSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-6-(hydroxymethyl)pyridine-3-carbonitrile Chemical compound S([C@H](C[C@@H](CO)N)C=1C=CC=CC=1)C1=NC(CO)=CC=C1C#N HTLOLXYEAIIKAX-GOEBONIOSA-N 0.000 claims 1
- XVXHJRVYVIKTMT-DOTOQJQBSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-6-ethylpyridine-3-carbonitrile Chemical compound CCC1=CC=C(C#N)C(S[C@H](C[C@H](N)CO)C=2C=CC=CC=2)=N1 XVXHJRVYVIKTMT-DOTOQJQBSA-N 0.000 claims 1
- KTCXAQJLADLIEB-JKSUJKDBSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-6-methylpyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C(S[C@H](C[C@H](N)CO)C=2C=CC=CC=2)=N1 KTCXAQJLADLIEB-JKSUJKDBSA-N 0.000 claims 1
- PUNPLJLIPQTZSK-FUHWJXTLSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-6-propan-2-ylpyridine-3-carbonitrile Chemical compound CC(C)C1=CC=C(C#N)C(S[C@H](C[C@H](N)CO)C=2C=CC=CC=2)=N1 PUNPLJLIPQTZSK-FUHWJXTLSA-N 0.000 claims 1
- WKIRSNXUUTYXGA-LSDHHAIUSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanylpyridine-3-carbonitrile Chemical compound S([C@H](C[C@@H](CO)N)C=1C=CC=CC=1)C1=NC=CC=C1C#N WKIRSNXUUTYXGA-LSDHHAIUSA-N 0.000 claims 1
- KGSAAGUVWAJGNT-SWLSCSKDSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-pyridin-3-ylbutoxy]-4-chloro-5-fluorobenzonitrile Chemical compound O([C@H](C[C@@H](CO)N)C=1C=NC=CC=1)C1=CC(Cl)=C(F)C=C1C#N KGSAAGUVWAJGNT-SWLSCSKDSA-N 0.000 claims 1
- BPXRCKUHATVTKL-GOEBONIOSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-pyridin-3-ylbutyl]sulfanyl-4-(trifluoromethyl)benzonitrile Chemical compound S([C@H](C[C@@H](CO)N)C=1C=NC=CC=1)C1=CC(C(F)(F)F)=CC=C1C#N BPXRCKUHATVTKL-GOEBONIOSA-N 0.000 claims 1
- BTUSSIMNGXKCMT-GOEBONIOSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-pyridin-3-ylbutyl]sulfanyl-4-bromobenzonitrile Chemical compound S([C@H](C[C@@H](CO)N)C=1C=NC=CC=1)C1=CC(Br)=CC=C1C#N BTUSSIMNGXKCMT-GOEBONIOSA-N 0.000 claims 1
- DIDQJYMKGKOYOT-SWLSCSKDSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-pyridin-3-ylbutyl]sulfanyl-4-chloro-5-fluorobenzonitrile Chemical compound S([C@H](C[C@@H](CO)N)C=1C=NC=CC=1)C1=CC(Cl)=C(F)C=C1C#N DIDQJYMKGKOYOT-SWLSCSKDSA-N 0.000 claims 1
- OZSJOTYNPDBWDC-DZGCQCFKSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-pyrimidin-5-ylbutyl]sulfanyl-4-chlorobenzonitrile Chemical compound S([C@H](C[C@@H](CO)N)C=1C=NC=NC=1)C1=CC(Cl)=CC=C1C#N OZSJOTYNPDBWDC-DZGCQCFKSA-N 0.000 claims 1
- IXWGKHPCJGYPIR-IINYFYTJSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-thiophen-2-ylbutoxy]-4-chloro-5-fluorobenzonitrile Chemical compound O([C@H](C[C@@H](CO)N)C=1SC=CC=1)C1=CC(Cl)=C(F)C=C1C#N IXWGKHPCJGYPIR-IINYFYTJSA-N 0.000 claims 1
- DBVCBFAVCHONCZ-SMDDNHRTSA-N 2-[(1r,3s)-3-amino-4-hydroxy-1-thiophen-3-ylbutoxy]-4-chloro-5-fluorobenzonitrile Chemical compound O([C@H](C[C@@H](CO)N)C1=CSC=C1)C1=CC(Cl)=C(F)C=C1C#N DBVCBFAVCHONCZ-SMDDNHRTSA-N 0.000 claims 1
- LIGOHHDFARYHPK-MSOLQXFVSA-N 2-[(1r,3s)-3-amino-4-hydroxy-4-methyl-1-phenylpentoxy]-4-chloro-5-fluorobenzonitrile Chemical compound O([C@H](C[C@H](N)C(C)(O)C)C=1C=CC=CC=1)C1=CC(Cl)=C(F)C=C1C#N LIGOHHDFARYHPK-MSOLQXFVSA-N 0.000 claims 1
- OKJQIFLIDFGZND-DLBZAZTESA-N 2-[(1r,3s)-3-amino-4-methoxy-1-phenylbutyl]sulfanyl-6-methylpyridine-3-carbonitrile Chemical compound S([C@H](C[C@H](N)COC)C=1C=CC=CC=1)C1=NC(C)=CC=C1C#N OKJQIFLIDFGZND-DLBZAZTESA-N 0.000 claims 1
- QEECXHATPPFYDI-KBPBESRZSA-N 2-[(2s,4s)-2-amino-1-hydroxy-6-methylheptan-4-yl]sulfanyl-6-methylpyridine-3-carbonitrile Chemical compound OC[C@@H](N)C[C@H](CC(C)C)SC1=NC(C)=CC=C1C#N QEECXHATPPFYDI-KBPBESRZSA-N 0.000 claims 1
- VIRCLXWIMXVKFE-QWRGUYRKSA-N 2-[(2s,4s)-2-amino-1-hydroxyheptan-4-yl]oxy-4-chloro-5-fluorobenzonitrile Chemical compound OC[C@@H](N)C[C@H](CCC)OC1=CC(Cl)=C(F)C=C1C#N VIRCLXWIMXVKFE-QWRGUYRKSA-N 0.000 claims 1
- LAYAIOYRSUSLIE-KBPBESRZSA-N 2-[(2s,4s)-2-amino-1-hydroxyoctan-4-yl]sulfanyl-6-methylpyridine-3-carbonitrile Chemical compound CCCC[C@@H](C[C@H](N)CO)SC1=NC(C)=CC=C1C#N LAYAIOYRSUSLIE-KBPBESRZSA-N 0.000 claims 1
- BENYGFIAYNBWCV-AMGKYWFPSA-N 2-[(3s)-3-amino-4-hydroxy-1-(1,2-oxazol-3-yl)butyl]sulfanyl-6-methylpyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C(SC(C[C@H](N)CO)C2=NOC=C2)=N1 BENYGFIAYNBWCV-AMGKYWFPSA-N 0.000 claims 1
- GOWFSIXJKZTEJX-FTNKSUMCSA-N 2-[(3s)-3-amino-4-hydroxy-1-(1,2-oxazol-5-yl)butoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound C=1C=NOC=1C(C[C@@H](CO)N)OC1=NC(C(F)(F)F)=CC=C1C#N GOWFSIXJKZTEJX-FTNKSUMCSA-N 0.000 claims 1
- SZUZRFDXIBISHP-AMGKYWFPSA-N 2-[(3s)-3-amino-4-hydroxy-1-(1,2-oxazol-5-yl)butyl]sulfanyl-6-methylpyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C(SC(C[C@H](N)CO)C=2ON=CC=2)=N1 SZUZRFDXIBISHP-AMGKYWFPSA-N 0.000 claims 1
- IZLCKIUETRPDGU-DZGCQCFKSA-N 3-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-5-chloropyridine-2-carbonitrile Chemical compound S([C@H](C[C@@H](CO)N)C=1C=CC=CC=1)C1=CC(Cl)=CN=C1C#N IZLCKIUETRPDGU-DZGCQCFKSA-N 0.000 claims 1
- ULUZUBLOCBUSRC-DZGCQCFKSA-N 3-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-5-methyl-6-oxo-1h-pyridine-2-carbonitrile Chemical compound N1C(=O)C(C)=CC(S[C@H](C[C@H](N)CO)C=2C=CC=CC=2)=C1C#N ULUZUBLOCBUSRC-DZGCQCFKSA-N 0.000 claims 1
- MPYBNYAUPXSCSU-GOEBONIOSA-N 3-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-5-methylpyridine-2-carbonitrile Chemical compound CC1=CN=C(C#N)C(S[C@H](C[C@H](N)CO)C=2C=CC=CC=2)=C1 MPYBNYAUPXSCSU-GOEBONIOSA-N 0.000 claims 1
- JAMDDXJMTFGUTN-IJNKOPBPSA-N 4-[(1R,3S)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-6-(trideuteriomethoxy)pyridine-3-carbonitrile Chemical compound N[C@@H](C[C@H](C1=CC=CC=C1)SC1=C(C=NC(=C1)OC([2H])([2H])[2H])C#N)CO JAMDDXJMTFGUTN-IJNKOPBPSA-N 0.000 claims 1
- JAMDDXJMTFGUTN-HUUCEWRRSA-N 4-[(1r,3r)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-6-methoxypyridine-3-carbonitrile Chemical compound C1=NC(OC)=CC(S[C@H](C[C@@H](N)CO)C=2C=CC=CC=2)=C1C#N JAMDDXJMTFGUTN-HUUCEWRRSA-N 0.000 claims 1
- CBYGFELGZZDIKF-BLLLJJGKSA-N 4-[(1r,3s)-3-amino-1-(2-fluorophenyl)-4-hydroxybutyl]sulfanyl-6-methoxypyridine-3-carbonitrile Chemical compound C1=NC(OC)=CC(S[C@H](C[C@H](N)CO)C=2C(=CC=CC=2)F)=C1C#N CBYGFELGZZDIKF-BLLLJJGKSA-N 0.000 claims 1
- RSHLPIYSILGCGI-GXFFZTMASA-N 4-[(1r,3s)-3-amino-1-(3-fluorothiophen-2-yl)-4-hydroxybutyl]sulfanyl-6-methoxypyridine-3-carbonitrile Chemical compound C1=NC(OC)=CC(S[C@H](C[C@H](N)CO)C2=C(C=CS2)F)=C1C#N RSHLPIYSILGCGI-GXFFZTMASA-N 0.000 claims 1
- YIUVSWGOUCEGFX-WMLDXEAASA-N 4-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-3-chlorobenzonitrile Chemical compound S([C@H](C[C@@H](CO)N)C=1C=CC=CC=1)C1=CC=C(C#N)C=C1Cl YIUVSWGOUCEGFX-WMLDXEAASA-N 0.000 claims 1
- XYJRJQLTFBRMNW-UONOGXRCSA-N 4-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-6-(difluoromethoxy)pyridine-3-carbonitrile Chemical compound S([C@H](C[C@@H](CO)N)C=1C=CC=CC=1)C1=CC(OC(F)F)=NC=C1C#N XYJRJQLTFBRMNW-UONOGXRCSA-N 0.000 claims 1
- ZFHVHQZHXMHYJT-JKSUJKDBSA-N 4-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-6-(dimethylamino)pyridine-3-carbonitrile Chemical compound C1=NC(N(C)C)=CC(S[C@H](C[C@H](N)CO)C=2C=CC=CC=2)=C1C#N ZFHVHQZHXMHYJT-JKSUJKDBSA-N 0.000 claims 1
- RWETWJXREZFDBU-LSDHHAIUSA-N 4-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-6-(methylamino)pyridine-3-carbonitrile Chemical compound C1=NC(NC)=CC(S[C@H](C[C@H](N)CO)C=2C=CC=CC=2)=C1C#N RWETWJXREZFDBU-LSDHHAIUSA-N 0.000 claims 1
- ZPCCYJVDOXZAPN-JKSUJKDBSA-N 4-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-6-ethoxypyridine-3-carbonitrile Chemical compound C1=NC(OCC)=CC(S[C@H](C[C@H](N)CO)C=2C=CC=CC=2)=C1C#N ZPCCYJVDOXZAPN-JKSUJKDBSA-N 0.000 claims 1
- JAMDDXJMTFGUTN-LSDHHAIUSA-N 4-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-6-methoxypyridine-3-carbonitrile Chemical compound C1=NC(OC)=CC(S[C@H](C[C@H](N)CO)C=2C=CC=CC=2)=C1C#N JAMDDXJMTFGUTN-LSDHHAIUSA-N 0.000 claims 1
- YFIIEFKPXKMQSQ-DOTOQJQBSA-N 4-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-6-methylpyridine-3-carbonitrile Chemical compound C1=NC(C)=CC(S[C@H](C[C@H](N)CO)C=2C=CC=CC=2)=C1C#N YFIIEFKPXKMQSQ-DOTOQJQBSA-N 0.000 claims 1
- JAMDDXJMTFGUTN-CABCVRRESA-N 4-[(1s,3r)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-6-methoxypyridine-3-carbonitrile Chemical compound C1=NC(OC)=CC(S[C@@H](C[C@@H](N)CO)C=2C=CC=CC=2)=C1C#N JAMDDXJMTFGUTN-CABCVRRESA-N 0.000 claims 1
- JAMDDXJMTFGUTN-GJZGRUSLSA-N 4-[(1s,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanyl-6-methoxypyridine-3-carbonitrile Chemical compound C1=NC(OC)=CC(S[C@@H](C[C@H](N)CO)C=2C=CC=CC=2)=C1C#N JAMDDXJMTFGUTN-GJZGRUSLSA-N 0.000 claims 1
- NYMDUXWDGONPMT-XHDPSFHLSA-N 4-chloro-2-[(1r,3s)-3-(ethylamino)-4-hydroxy-1-(1,3-thiazol-2-yl)butoxy]-5-fluorobenzonitrile Chemical compound O([C@H](C[C@@H](CO)NCC)C=1SC=CN=1)C1=CC(Cl)=C(F)C=C1C#N NYMDUXWDGONPMT-XHDPSFHLSA-N 0.000 claims 1
- XMWKGTYELFIHHT-DOTOQJQBSA-N 6-acetyl-2-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanylpyridine-3-carbonitrile Chemical compound CC(=O)C1=CC=C(C#N)C(S[C@H](C[C@H](N)CO)C=2C=CC=CC=2)=N1 XMWKGTYELFIHHT-DOTOQJQBSA-N 0.000 claims 1
- IDPXSXZYYMTFOQ-UONOGXRCSA-N 6-amino-4-[(1r,3s)-3-amino-4-hydroxy-1-phenylbutyl]sulfanylpyridine-3-carbonitrile Chemical compound S([C@H](C[C@@H](CO)N)C=1C=CC=CC=1)C1=CC(N)=NC=C1C#N IDPXSXZYYMTFOQ-UONOGXRCSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 description 6
- 230000004054 inflammatory process Effects 0.000 description 6
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- 102000001708 Protein Isoforms Human genes 0.000 description 3
- 108010029485 Protein Isoforms Proteins 0.000 description 3
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 2
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 2
- 0 CCCC(*)CC(*)(C(*)(O*)S)N* Chemical compound CCCC(*)CC(*)(C(*)(O*)S)N* 0.000 description 1
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| SE0103271A SE0103271D0 (sv) | 2001-09-28 | 2001-09-28 | Novel compounds |
| PCT/SE2002/000876 WO2002090332A2 (en) | 2001-05-08 | 2002-05-06 | Novel aeylheteroalkylaminε derivatives |
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| GB0004152D0 (en) | 2000-02-23 | 2000-04-12 | Astrazeneca Uk Ltd | Novel compounds |
| SE0102640D0 (sv) | 2001-07-31 | 2001-07-31 | Astrazeneca Ab | Novel compounds |
| SE0203304D0 (sv) * | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Coumpounds |
| CA2554696C (en) | 2004-02-13 | 2009-06-30 | Warner-Lambert Company Llc | Androgen receptor modulators |
| EP1737813A1 (en) | 2004-04-13 | 2007-01-03 | Warner-Lambert Company LLC | Androgen modulators |
| WO2005102990A1 (en) | 2004-04-22 | 2005-11-03 | Warner-Lambert Company Llc | Androgen modulators |
| CA2570047C (en) | 2004-07-08 | 2010-09-28 | Warner-Lambert Company Llc | 4-cycloalkoxy benzonitriles as androgen modulators |
| TW200724139A (en) | 2005-05-05 | 2007-07-01 | Warner Lambert Co | Androgen modulators |
| EP2161998B1 (en) * | 2007-06-04 | 2015-09-02 | Intra-Cellular Therapies, Inc. | Pyridine derivatives as NET/SERT modulators |
| CN104069112A (zh) | 2007-10-19 | 2014-10-01 | 贝林格尔.英格海姆国际有限公司 | 取代的哌啶子基-二氢噻吩并嘧啶 |
| DK2379525T3 (en) | 2008-12-19 | 2015-10-19 | Boehringer Ingelheim Int | Cyclic pyrimidin-4-carboxamides, as CCR2 receptor antagonists for the treatment of inflammation, asthma and COPD |
| WO2011073155A1 (en) | 2009-12-17 | 2011-06-23 | Boehringer Ingelheim International Gmbh | Novel antagonists for ccr2 and uses thereof |
| WO2011073154A1 (en) | 2009-12-17 | 2011-06-23 | Boehringer Ingelheim International Gmbh | New ccr2 receptor antagonists and uses thereof |
| CN102822172A (zh) | 2010-01-29 | 2012-12-12 | 贝林格尔.英格海姆国际有限公司 | 取代的二氮杂萘及其作为syk 激酶抑制剂的用途 |
| EP2569295B1 (en) | 2010-05-12 | 2014-11-19 | Boehringer Ingelheim International GmbH | New ccr2 receptor antagonists, method for producing the same, and use thereof as medicaments |
| US8877745B2 (en) | 2010-05-12 | 2014-11-04 | Boehringer Ingelheim International Gmbh | CCR2 receptor antagonists, method for producing the same, and use thereof as medicaments |
| US8841313B2 (en) | 2010-05-17 | 2014-09-23 | Boehringer Ingelheim International Gmbh | CCR2 antagonists and uses thereof |
| US9018212B2 (en) | 2010-05-25 | 2015-04-28 | Boehringer Ingelheim International Gmbh | Pyridazine carboxamides as CCR2 receptor antagonists |
| EP2576538B1 (en) | 2010-06-01 | 2015-10-28 | Boehringer Ingelheim International GmbH | New CCR2 antagonists |
| JP5959537B2 (ja) | 2011-01-28 | 2016-08-02 | 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 | 置換ピリジニル−ピリミジン及び医薬としてのその使用 |
| WO2012171863A1 (en) | 2011-06-16 | 2012-12-20 | Boehringer Ingelheim International Gmbh | New selective ccr2 antagonists |
| JP5786258B2 (ja) | 2011-07-15 | 2015-09-30 | 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 | 新規かつ選択的なｃｃｒ２拮抗薬 |
| CA2843022C (en) | 2011-07-26 | 2019-09-24 | Boehringer Ingelheim International Gmbh | Substituted quinolines and their use as medicaments |
| US20130059866A1 (en) | 2011-08-24 | 2013-03-07 | Boehringer Ingelheim International Gmbh | Novel piperidino-dihydrothienopyrimidine sulfoxides and their use for treating copd and asthma |
| US9096579B2 (en) | 2012-04-20 | 2015-08-04 | Boehringer Ingelheim International Gmbh | Amino-indolyl-substituted imidazolyl-pyrimidines and their use as medicaments |
| CA2942997C (en) | 2014-03-19 | 2022-09-13 | Boehringer Ingelheim International Gmbh | Heteroaryl syk inhibitors |
| CN109096276B (zh) * | 2018-08-01 | 2021-05-28 | 上海博志研新药物技术有限公司 | 盐酸莫西沙星及其中间体的制备方法 |
| CN112898285B (zh) * | 2020-01-14 | 2022-05-24 | 河南师范大学 | 含三氟甲基双噁唑类化合物及其合成方法和在抗癌药物中的应用 |
| CN115677572B (zh) * | 2021-07-29 | 2024-05-28 | 武汉思瓴生物科技有限公司 | 氟代酰胺类衍生物、药物组合物及其应用 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2688638A (en) * | 1951-07-17 | 1954-09-07 | Givaudan Corp | Nu-(beta-phenoxyethyl) haloethylamines |
| US4314081A (en) * | 1974-01-10 | 1982-02-02 | Eli Lilly And Company | Arloxyphenylpropylamines |
| FR2432500A1 (fr) * | 1978-02-24 | 1980-02-29 | Roussel Uclaf | Nouveaux derives de la benzene propanamine et leurs sels, procede de preparation et application a titre de medicaments |
| DE3138550A1 (de) * | 1981-09-28 | 1983-04-07 | Boehringer Ingelheim KG, 6507 Ingelheim | Substituierte 2-phenyl-2-(pyridyloxy)-ethylamine und isostere verbindungen, verfahren zu ihrer herstellung und verwendung |
| US4902710A (en) * | 1988-12-14 | 1990-02-20 | Eli Lilly And Company | Serotonin and norepinephrine uptake inhibitors |
| SE9703693D0 (sv) * | 1997-10-10 | 1997-10-10 | Astra Pharma Prod | Novel combination |
| SE9803773D0 (sv) * | 1998-11-05 | 1998-11-05 | Astra Pharma Prod | Compounds |
| GB0004149D0 (en) * | 2000-02-23 | 2000-04-12 | Astrazeneca Uk Ltd | Novel compounds |
| GB0004151D0 (en) * | 2000-02-23 | 2000-04-12 | Astrazeneca Uk Ltd | Novel use |
| GB0004152D0 (en) * | 2000-02-23 | 2000-04-12 | Astrazeneca Uk Ltd | Novel compounds |
| GB0004153D0 (en) * | 2000-02-23 | 2000-04-12 | Astrazeneca Uk Ltd | Novel use |
| US7084122B2 (en) * | 2001-11-21 | 2006-08-01 | Erik Larsen | Use of glycosides of mono- and diacyglycerol as anti-inflammatory agents |
| SE0203304D0 (sv) * | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Coumpounds |
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2002
- 2002-04-30 AR ARP020101589A patent/AR035700A1/es not_active Application Discontinuation
- 2002-05-06 AU AU2002306039A patent/AU2002306039B2/en not_active Expired - Fee Related
- 2002-05-06 TW TW091109347A patent/TWI278450B/zh not_active IP Right Cessation
- 2002-05-06 IL IL15838802A patent/IL158388A0/xx unknown
- 2002-05-06 KR KR10-2003-7014492A patent/KR20030096361A/ko not_active Ceased
- 2002-05-06 JP JP2002587412A patent/JP2005506308A/ja active Pending
- 2002-05-06 MX MXPA03010142A patent/MXPA03010142A/es not_active Application Discontinuation
- 2002-05-06 NZ NZ529107A patent/NZ529107A/en unknown
- 2002-05-06 EP EP02733658A patent/EP1572655A2/en not_active Withdrawn
- 2002-05-06 CN CNB028096185A patent/CN100340548C/zh not_active Expired - Fee Related
- 2002-05-06 WO PCT/SE2002/000876 patent/WO2002090332A2/en not_active Ceased
- 2002-05-06 US US10/476,958 patent/US20040242871A1/en not_active Abandoned
- 2002-05-06 CA CA002446120A patent/CA2446120A1/en not_active Abandoned
- 2002-05-06 BR BR0209518-1A patent/BR0209518A/pt not_active IP Right Cessation
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2003
- 2003-11-07 NO NO20034970A patent/NO20034970D0/no not_active Application Discontinuation
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