JP2015509510A5 - - Google Patents
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- Publication number
- JP2015509510A5 JP2015509510A5 JP2014560224A JP2014560224A JP2015509510A5 JP 2015509510 A5 JP2015509510 A5 JP 2015509510A5 JP 2014560224 A JP2014560224 A JP 2014560224A JP 2014560224 A JP2014560224 A JP 2014560224A JP 2015509510 A5 JP2015509510 A5 JP 2015509510A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- hydroxypyrrolidin
- methyl
- oxo
- acetamide
- 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
- -1 cyano, hydroxyl Chemical group 0.000 claims description 136
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 80
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 73
- 150000001875 compounds Chemical class 0.000 claims description 55
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 38
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 34
- 239000008194 pharmaceutical composition Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 23
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 102000048260 kappa Opioid Receptors Human genes 0.000 claims description 14
- 108020001588 κ-opioid receptors Proteins 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 8
- 210000003169 central nervous system Anatomy 0.000 claims description 8
- 102000003840 Opioid Receptors Human genes 0.000 claims description 6
- 108090000137 Opioid Receptors Proteins 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 5
- 239000000556 agonist Substances 0.000 claims description 5
- 235000010233 benzoic acid Nutrition 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 230000007160 gastrointestinal dysfunction Effects 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 4
- 208000003243 intestinal obstruction Diseases 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- SGVZPNMDWMVUNW-GHTZIAJQSA-N 2-(2,2-dimethyl-3-oxo-4h-1,4-benzothiazin-6-yl)-n-[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl]-n-methylacetamide Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2NC(=O)C(C)(C)SC2=CC=1)C=1C=C(OC(F)(F)F)C=CC=1)N1CC[C@H](O)C1 SGVZPNMDWMVUNW-GHTZIAJQSA-N 0.000 claims description 2
- BLZPUFHLMOHBHZ-GOSISDBHSA-N 2-(2-oxo-3h-1,3-benzothiazol-5-yl)-n-[(1s)-1-phenyl-2-pyrrolidin-1-ylethyl]acetamide Chemical compound C([C@@H](NC(CC=1C=C2NC(=O)SC2=CC=1)=O)C=1C=CC=CC=1)N1CCCC1 BLZPUFHLMOHBHZ-GOSISDBHSA-N 0.000 claims description 2
- LYTSGCDUWUHESO-FXAWDEMLSA-N 2-(3,3-difluoro-2-oxo-1h-indol-6-yl)-n-[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-phenylethyl]-n-methylacetamide Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2C(C(C(=O)N2)(F)F)=CC=1)C=1C=CC=CC=1)N1CC[C@H](O)C1 LYTSGCDUWUHESO-FXAWDEMLSA-N 0.000 claims description 2
- OIPIMWKUTPLWFW-AREMUKBSSA-N 2-(3-benzyl-2-oxo-1,3-benzoxazol-5-yl)-n-[(1s)-1-(3-hydroxyphenyl)-2-pyrrolidin-1-ylethyl]-n-methylacetamide Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2N(CC=3C=CC=CC=3)C(=O)OC2=CC=1)C=1C=C(O)C=CC=1)N1CCCC1 OIPIMWKUTPLWFW-AREMUKBSSA-N 0.000 claims description 2
- ACUMPGYAITXCPN-AHKZPQOWSA-N 2-[3-[(3-cyanophenyl)methyl]-2-oxo-1,3-benzoxazol-5-yl]-n-[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-phenylethyl]-n-methylacetamide Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2N(CC=3C=C(C=CC=3)C#N)C(=O)OC2=CC=1)C=1C=CC=CC=1)N1CC[C@H](O)C1 ACUMPGYAITXCPN-AHKZPQOWSA-N 0.000 claims description 2
- QAWDILRRYNWRLE-AZUAARDMSA-N 2-[5-[2-[[(1s)-1-cyclohexyl-2-[(3s)-3-hydroxypyrrolidin-1-yl]ethyl]-methylamino]-2-oxoethyl]-2-oxo-1,3-benzoxazol-3-yl]acetic acid Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2N(CC(O)=O)C(=O)OC2=CC=1)C1CCCCC1)N1CC[C@H](O)C1 QAWDILRRYNWRLE-AZUAARDMSA-N 0.000 claims description 2
- LOMPUFLEYCRGRB-PZJWPPBQSA-N 3-[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-[methyl-[2-(2-oxo-1,3-dihydroindol-6-yl)acetyl]amino]ethyl]benzoic acid Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2NC(=O)CC2=CC=1)C=1C=C(C=CC=1)C(O)=O)N1CC[C@H](O)C1 LOMPUFLEYCRGRB-PZJWPPBQSA-N 0.000 claims description 2
- BOJYGVJQAMBGOA-AZUAARDMSA-N 3-[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-[methyl-[2-(3-oxo-4h-1,4-benzothiazin-6-yl)acetyl]amino]ethyl]benzamide Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2NC(=O)CSC2=CC=1)C=1C=C(C=CC=1)C(N)=O)N1CC[C@H](O)C1 BOJYGVJQAMBGOA-AZUAARDMSA-N 0.000 claims description 2
- QVOROBUQQZCPSM-AZUAARDMSA-N 3-[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-[methyl-[2-(3-oxo-4h-1,4-benzothiazin-6-yl)acetyl]amino]ethyl]benzoic acid Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2NC(=O)CSC2=CC=1)C=1C=C(C=CC=1)C(O)=O)N1CC[C@H](O)C1 QVOROBUQQZCPSM-AZUAARDMSA-N 0.000 claims description 2
- KLJYDDBOUQSYMT-XUZZJYLKSA-N CCN(CC)C(=O)COc1cccc(c1)[C@@H](CN1CC[C@H](O)C1)N(C)C(=O)Cc1ccc2sc(=O)[nH]c2c1 Chemical compound CCN(CC)C(=O)COc1cccc(c1)[C@@H](CN1CC[C@H](O)C1)N(C)C(=O)Cc1ccc2sc(=O)[nH]c2c1 KLJYDDBOUQSYMT-XUZZJYLKSA-N 0.000 claims description 2
- UCTICLYUGDQTDK-JTHBVZDNSA-N CN(C)C(=O)c1cccc(c1)[C@@H](CN1CC[C@H](O)C1)N(C)C(=O)Cc1ccc2CC(=O)Nc2c1 Chemical compound CN(C)C(=O)c1cccc(c1)[C@@H](CN1CC[C@H](O)C1)N(C)C(=O)Cc1ccc2CC(=O)Nc2c1 UCTICLYUGDQTDK-JTHBVZDNSA-N 0.000 claims description 2
- BYJFNCGTFBQSSE-MGBGTMOVSA-N CN([C@H](CN1CCCC1)c1cccc(OCc2ccccc2)c1)C(=O)Cc1ccc2oc(=O)n(Cc3ccccc3)c2c1 Chemical compound CN([C@H](CN1CCCC1)c1cccc(OCc2ccccc2)c1)C(=O)Cc1ccc2oc(=O)n(Cc3ccccc3)c2c1 BYJFNCGTFBQSSE-MGBGTMOVSA-N 0.000 claims description 2
- FLBURDBXWCXKHW-YLJYHZDGSA-N CN([C@H](CN1CC[C@@H](O)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2oc(=O)[nH]c2c1 Chemical compound CN([C@H](CN1CC[C@@H](O)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2oc(=O)[nH]c2c1 FLBURDBXWCXKHW-YLJYHZDGSA-N 0.000 claims description 2
- WEEAIRCTYSPLGL-SIKLNZKXSA-N CN([C@H](CN1CC[C@H](F)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2CC(=O)Nc2c1 Chemical compound CN([C@H](CN1CC[C@H](F)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2CC(=O)Nc2c1 WEEAIRCTYSPLGL-SIKLNZKXSA-N 0.000 claims description 2
- YLWCSTGKLCPTPI-PZJWPPBQSA-N CN([C@H](CN1CC[C@H](F)C1)c1cccc(c1)C(O)=O)C(=O)Cc1ccc2CC(=O)Nc2c1 Chemical compound CN([C@H](CN1CC[C@H](F)C1)c1cccc(c1)C(O)=O)C(=O)Cc1ccc2CC(=O)Nc2c1 YLWCSTGKLCPTPI-PZJWPPBQSA-N 0.000 claims description 2
- HIKJOZMEOICVPB-SIKLNZKXSA-N CN([C@H](CN1CC[C@H](O)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2CC(=O)Nc2c1 Chemical compound CN([C@H](CN1CC[C@H](O)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2CC(=O)Nc2c1 HIKJOZMEOICVPB-SIKLNZKXSA-N 0.000 claims description 2
- QDPYEFQBGAUFDH-SIKLNZKXSA-N CN([C@H](CN1CC[C@H](O)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2NC(=O)Cc2c1 Chemical compound CN([C@H](CN1CC[C@H](O)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2NC(=O)Cc2c1 QDPYEFQBGAUFDH-SIKLNZKXSA-N 0.000 claims description 2
- GDNKHKZTQMVGCK-AZUAARDMSA-N CN([C@H](CN1CC[C@H](O)C1)c1cccc(c1)C(O)=O)C(=O)Cc1ccc2OCC(=O)Nc2c1 Chemical compound CN([C@H](CN1CC[C@H](O)C1)c1cccc(c1)C(O)=O)C(=O)Cc1ccc2OCC(=O)Nc2c1 GDNKHKZTQMVGCK-AZUAARDMSA-N 0.000 claims description 2
- IFOUKQQRZCJINU-AZUAARDMSA-N CN([C@H](CN1CC[C@H](O)C1)c1ccccc1)C(=O)Cc1ccc2oc(=O)n(CC(O)=O)c2c1 Chemical compound CN([C@H](CN1CC[C@H](O)C1)c1ccccc1)C(=O)Cc1ccc2oc(=O)n(CC(O)=O)c2c1 IFOUKQQRZCJINU-AZUAARDMSA-N 0.000 claims description 2
- HPLCKHUKWVLQLI-AZGAKELHSA-N CN([C@H](CN1CC[C@H](O)C1)c1ccccc1)C(=O)Cc1ccc2oc(=O)n(Cc3cccc(c3)-c3nn[nH]n3)c2c1 Chemical compound CN([C@H](CN1CC[C@H](O)C1)c1ccccc1)C(=O)Cc1ccc2oc(=O)n(Cc3cccc(c3)-c3nn[nH]n3)c2c1 HPLCKHUKWVLQLI-AZGAKELHSA-N 0.000 claims description 2
- MJDXDYJOADNCJR-UHFFFAOYSA-N Cl.CN(C(CN1CCCC1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2CC(=O)Nc2c1 Chemical compound Cl.CN(C(CN1CCCC1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2CC(=O)Nc2c1 MJDXDYJOADNCJR-UHFFFAOYSA-N 0.000 claims description 2
- NGUMEXYEHGUXDT-FSRHSHDFSA-N Cl.OC(=O)COc1cccc(c1)[C@@H](CN1CCCC1)NC(=O)Cc1ccc2oc(=O)[nH]c2c1 Chemical compound Cl.OC(=O)COc1cccc(c1)[C@@H](CN1CCCC1)NC(=O)Cc1ccc2oc(=O)[nH]c2c1 NGUMEXYEHGUXDT-FSRHSHDFSA-N 0.000 claims description 2
- CWTCHUFBPAOJFU-GMUIIQOCSA-N Cl.OC(=O)Cn1c2cc(CC(=O)N[C@H](CN3CCCC3)c3ccccc3)ccc2oc1=O Chemical compound Cl.OC(=O)Cn1c2cc(CC(=O)N[C@H](CN3CCCC3)c3ccccc3)ccc2oc1=O CWTCHUFBPAOJFU-GMUIIQOCSA-N 0.000 claims description 2
- IKEWDDJBOFQKQK-UHFFFAOYSA-N OC(=O)COc1cccc(c1)C(CN1CCCC1)NC(=O)Cc1ccc2CC(=O)Nc2c1 Chemical compound OC(=O)COc1cccc(c1)C(CN1CCCC1)NC(=O)Cc1ccc2CC(=O)Nc2c1 IKEWDDJBOFQKQK-UHFFFAOYSA-N 0.000 claims description 2
- IKKGXDNOHGKYEX-LZAGWAHOSA-N [O-]C(=O)C(F)(F)F.CN([C@H](CN1CC[C@H](O)C1)c1ccccc1)C(=O)Cc1ccc2[NH2+]S(=O)(=O)Cc2c1 Chemical compound [O-]C(=O)C(F)(F)F.CN([C@H](CN1CC[C@H](O)C1)c1ccccc1)C(=O)Cc1ccc2[NH2+]S(=O)(=O)Cc2c1 IKKGXDNOHGKYEX-LZAGWAHOSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- BMBANPOHPFKVTA-UHFFFAOYSA-N benzamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NC(=O)C1=CC=CC=C1 BMBANPOHPFKVTA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 claims description 2
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- OPCUHICXVGFAAO-PZJWPPBQSA-N n-[(1s)-1-(3-ethynylphenyl)-2-[(3s)-3-hydroxypyrrolidin-1-yl]ethyl]-n-methyl-2-(2-oxo-3h-1,3-benzothiazol-5-yl)acetamide Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2NC(=O)SC2=CC=1)C=1C=C(C=CC=1)C#C)N1CC[C@H](O)C1 OPCUHICXVGFAAO-PZJWPPBQSA-N 0.000 claims description 2
- AVYAYWUTODIOFY-AZGAKELHSA-N n-[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-phenylethyl]-n-methyl-2-[2-oxo-3-[[4-(2h-tetrazol-5-yl)phenyl]methyl]-1,3-benzoxazol-5-yl]acetamide Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2N(CC=3C=CC(=CC=3)C3=NNN=N3)C(=O)OC2=CC=1)C=1C=CC=CC=1)N1CC[C@H](O)C1 AVYAYWUTODIOFY-AZGAKELHSA-N 0.000 claims description 2
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims description 2
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- SMXZZNJEHDKCKX-PZJWPPBQSA-N 3-[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-[methyl-[2-(2-oxo-1,3-dihydroindol-6-yl)acetyl]amino]ethyl]benzamide Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2NC(=O)CC2=CC=1)C=1C=C(C=CC=1)C(N)=O)N1CC[C@H](O)C1 SMXZZNJEHDKCKX-PZJWPPBQSA-N 0.000 claims 1
- 230000021615 conjugation Effects 0.000 claims 1
- XAVBRHQYBNDKED-PZJWPPBQSA-N n-[(1s)-2-[(3s)-3-hydroxypyrrolidin-1-yl]-1-phenylethyl]-n-methyl-2-(2-oxo-1,3-dihydroindol-6-yl)acetamide Chemical compound C([C@@H](N(C)C(=O)CC=1C=C2NC(=O)CC2=CC=1)C=1C=CC=CC=1)N1CC[C@H](O)C1 XAVBRHQYBNDKED-PZJWPPBQSA-N 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001107 pteroylglutamyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 description 18
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
- 0 CCC(CCN(C[C@](*)C(C)N(*)C(C(*)(*)*)=O)C1)[C@@]1O Chemical compound CCC(CCN(C[C@](*)C(C)N(*)C(C(*)(*)*)=O)C1)[C@@]1O 0.000 description 1
- JKTYNWTVBPFVDU-PGRDOPGGSA-N CN([C@H](CN1CC[C@H](O)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2ncc(=O)[nH]c2c1 Chemical compound CN([C@H](CN1CC[C@H](O)C1)c1cccc(OCC(O)=O)c1)C(=O)Cc1ccc2ncc(=O)[nH]c2c1 JKTYNWTVBPFVDU-PGRDOPGGSA-N 0.000 description 1
- YAVDEXADPNAAAM-PKOBYXMFSA-N CN([C@H](CN1CC[C@H](O)C1)c1cccc(c1)C(O)=O)C(=O)Cc1ccc2oc(=O)[nH]c2c1 Chemical compound CN([C@H](CN1CC[C@H](O)C1)c1cccc(c1)C(O)=O)C(=O)Cc1ccc2oc(=O)[nH]c2c1 YAVDEXADPNAAAM-PKOBYXMFSA-N 0.000 description 1
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261606632P | 2012-03-05 | 2012-03-05 | |
| US61/606,632 | 2012-03-05 | ||
| PCT/CN2013/000230 WO2013131408A1 (en) | 2012-03-05 | 2013-03-05 | Substituted heterocyclic acetamides as kappa opioid receptor (kor) agonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015509510A JP2015509510A (ja) | 2015-03-30 |
| JP2015509510A5 true JP2015509510A5 (https=) | 2016-02-25 |
| JP6138169B2 JP6138169B2 (ja) | 2017-05-31 |
Family
ID=49115926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014560224A Expired - Fee Related JP6138169B2 (ja) | 2012-03-05 | 2013-03-05 | κオピオイド受容体（ＫＯＲ）アゴニストとしての置換複素環式アセトアミド |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US9487510B2 (https=) |
| EP (1) | EP2822928B1 (https=) |
| JP (1) | JP6138169B2 (https=) |
| KR (1) | KR101773331B1 (https=) |
| CN (1) | CN104271552B (https=) |
| AU (1) | AU2013230425B2 (https=) |
| CA (1) | CA2866299C (https=) |
| DK (1) | DK2822928T3 (https=) |
| MX (1) | MX355142B (https=) |
| NZ (1) | NZ629630A (https=) |
| WO (1) | WO2013131408A1 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102318476B1 (ko) | 2010-07-22 | 2021-11-01 | 카-페 시스템 게엠베하 | 음료수 제조를 위한 1인용 캡슐 |
| US9487510B2 (en) * | 2012-03-05 | 2016-11-08 | Dr. Reddy's Laboratories Ltd. | Substituted heterocyclic acetamides as kappa opioid receptor (KOR) agonists |
| CN103664727A (zh) * | 2013-12-19 | 2014-03-26 | 无锡万全医药技术有限公司 | 一种一锅法制备1-[(3s)-3-羟基吡咯烷-1-基]-(2s)-2-甲氨基-2-苯基乙烷的工艺 |
| CN103772257A (zh) * | 2013-12-31 | 2014-05-07 | 无锡万全医药技术有限公司 | 一种制备2-((3s)-3-羟基吡咯烷-1-基)-(1s)-1-苯乙基氨基甲酸酯的方法 |
| EA201691489A1 (ru) * | 2014-01-24 | 2016-12-30 | Кадила Хелзкэр Лимитед | Новые гетероциклические соединения в качестве агонистов каппа-опиодиов |
| MA42130A (fr) | 2015-05-21 | 2018-03-28 | Therapix Biosciences Ltd | Combinaisons d'opioïdes et de n-acyléthanolamines |
| CN105061288B (zh) * | 2015-08-07 | 2017-09-15 | 武汉华素康生物科技有限公司 | 化合物及其制备方法和应用 |
| AU2017277003B2 (en) * | 2016-06-07 | 2021-01-07 | Jiangsu Hengrui Medicine Co., Ltd. | Phenyl propanamide derivative, and manufacturing method and pharmaceutical application thereof |
| JP2020524718A (ja) * | 2017-06-22 | 2020-08-20 | キュラデブ・ファーマ・リミテッドＣｕｒａｄｅｖ Ｐｈａｒｍａ Ｌｉｍｉｔｅｄ | ヒトｓｔｉｎｇの複素環式小分子調節因子 |
| US11045805B2 (en) * | 2017-11-01 | 2021-06-29 | Bio-Rad Laboratories, Inc. | Microfluidic system and method for arranging objects |
| JP2021505547A (ja) * | 2017-12-06 | 2021-02-18 | 江蘇恒瑞医薬股▲ふん▼有限公司 | 疼痛を治療するための薬物の製造におけるｍｏｒアゴニストと組み合わせたｋｏｒアゴニストの使用 |
| CA3084201A1 (en) * | 2017-12-06 | 2019-06-13 | Jiangsu Hengrul Medicine Co., Ltd. | Salt of phenylpropionamide derivative and preparation method therefor |
| CN109879934B (zh) * | 2017-12-06 | 2020-12-08 | 江苏恒瑞医药股份有限公司 | 一种苯基丙酰胺类衍生物的盐及其制备方法 |
| CN113624898B (zh) * | 2021-08-23 | 2023-08-25 | 成都诺和晟泰生物科技有限公司 | 一种手性镇痛类多肽药物的纯化方法 |
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| DE4034785A1 (de) * | 1990-11-02 | 1992-05-07 | Merck Patent Gmbh | 1-(2-arylethyl)-pyrrolidine |
| US5232978A (en) * | 1988-12-23 | 1993-08-03 | Merck Patent Gesellschaft Mit Beschrankter Haftung | 1-(2-arylethyl)-pyrrolidines |
| US5681830A (en) | 1992-02-03 | 1997-10-28 | Delta Pharmaceuticals, Inc. | Opioid compounds |
| AU686203B2 (en) | 1993-07-23 | 1998-02-05 | Toray Industries, Inc. | Morphinan derivative and medicinal use |
| DE4407047A1 (de) * | 1994-03-03 | 1995-09-07 | Merck Patent Gmbh | Acetamide |
| IL117440A0 (en) * | 1995-03-31 | 1996-07-23 | Pfizer | Pyrrolidinyl hydroxamic acid compounds and their production process |
| DE19523502A1 (de) * | 1995-06-28 | 1997-01-02 | Merck Patent Gmbh | Kappa-Opiatagonisten für entzündliche Darmerkrankungen |
| US6303611B1 (en) * | 1996-03-08 | 2001-10-16 | Adolor Corporation | Kappa agonist compounds and pharmaceutical formulations thereof |
| US6133307A (en) * | 1997-04-30 | 2000-10-17 | Warner-Lambert Company | Certain benzofuranyl-N-[pyrrolidin-1-YL]-N-methyl-acetamide derivatives useful as opioid agonists |
| CA2480560C (en) | 2002-03-29 | 2011-02-15 | Santen Pharmaceutical Co., Ltd. | .kappa.-opioid receptor agonist comprising 2-phenylbenzothiazoline derivative |
| CL2007002097A1 (es) * | 2006-07-20 | 2008-01-18 | Smithkline Beecham Corp | Compuestos derivados de pirrolidina o morfolina antagonistas de urotensina ii; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar insuficiencia cardiaca congestiva, insuficiencia cardiaca isquemica, angina, isquemia del miocardio, vejiga hiperactiva, asma y/o copd, entre otras. |
| CA2683461A1 (en) * | 2007-04-16 | 2008-10-23 | Gruenenthal Gmbh | Novel vanilloid receptor ligands and the use thereof for the production of pharmaceuticals |
| WO2012012410A2 (en) * | 2010-07-19 | 2012-01-26 | Dr. Reddy's Laboratories Ltd. | Kappa opioid receptor agonists |
| US9487510B2 (en) * | 2012-03-05 | 2016-11-08 | Dr. Reddy's Laboratories Ltd. | Substituted heterocyclic acetamides as kappa opioid receptor (KOR) agonists |
-
2013
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- 2013-03-05 DK DK13757759.9T patent/DK2822928T3/en active
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- 2013-03-05 JP JP2014560224A patent/JP6138169B2/ja not_active Expired - Fee Related
- 2013-03-05 WO PCT/CN2013/000230 patent/WO2013131408A1/en not_active Ceased
- 2013-03-05 EP EP13757759.9A patent/EP2822928B1/en not_active Not-in-force
- 2013-03-05 CA CA2866299A patent/CA2866299C/en not_active Expired - Fee Related
- 2013-03-05 NZ NZ629630A patent/NZ629630A/en not_active IP Right Cessation
- 2013-03-05 KR KR1020147025946A patent/KR101773331B1/ko not_active Expired - Fee Related
- 2013-03-05 AU AU2013230425A patent/AU2013230425B2/en not_active Ceased
- 2013-03-05 CN CN201380023425.8A patent/CN104271552B/zh not_active Expired - Fee Related
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2016
- 2016-09-19 US US15/269,267 patent/US10131655B2/en not_active Expired - Fee Related
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