JP2017523219A5 - - Google Patents
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- JP2017523219A5 JP2017523219A5 JP2017506712A JP2017506712A JP2017523219A5 JP 2017523219 A5 JP2017523219 A5 JP 2017523219A5 JP 2017506712 A JP2017506712 A JP 2017506712A JP 2017506712 A JP2017506712 A JP 2017506712A JP 2017523219 A5 JP2017523219 A5 JP 2017523219A5
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- JP
- Japan
- Prior art keywords
- methyl
- salt form
- compound
- free
- pyrazolo
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 61
- 150000003839 salts Chemical group 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- -1 (6aR, 9aS) -5-methyl-4-oxo-3- (phenylamino) -4,5,7,8,9,9a-hexahydrocyclopenta [4,5] imidazo [1, 2-a] pyrazolo [4,3-e] pyrimidin-2 (6aH) -yl Chemical group 0.000 claims description 14
- 102000003729 Neprilysin Human genes 0.000 claims description 11
- 108090000028 Neprilysin Proteins 0.000 claims description 11
- 208000035475 disorder Diseases 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 8
- 239000003112 inhibitor Substances 0.000 claims description 8
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 5
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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- MZMYHAYKVAFIAB-UHFFFAOYSA-N FC1=CC=C(C=C1)NC=1N(N=C2C=1C(N(C=1N2CC(N=1)(C)C)C)=O)CC1=CC=C(C=C1)C1=NC(=CC=C1)O Chemical compound FC1=CC=C(C=C1)NC=1N(N=C2C=1C(N(C=1N2CC(N=1)(C)C)C)=O)CC1=CC=C(C=C1)C1=NC(=CC=C1)O MZMYHAYKVAFIAB-UHFFFAOYSA-N 0.000 claims description 2
- PPNCNFZHIYIITJ-UHFFFAOYSA-N FC1=CC=C(C=C1)NC=1N(N=C2C=1C(N(C=1N2CC(N=1)(C)C)C)=O)CC1=CC=NC=C1 Chemical compound FC1=CC=C(C=C1)NC=1N(N=C2C=1C(N(C=1N2CC(N=1)(C)C)C)=O)CC1=CC=NC=C1 PPNCNFZHIYIITJ-UHFFFAOYSA-N 0.000 claims description 2
- WBQTUTZNKDRZPA-UHFFFAOYSA-N FC1=CC=C(C=C1)NC=1N(N=C2C=1C(N(C=1N2CC(N=1)(C)C)C)=O)CC=1C=NC(=CC=1)C Chemical compound FC1=CC=C(C=C1)NC=1N(N=C2C=1C(N(C=1N2CC(N=1)(C)C)C)=O)CC=1C=NC(=CC=1)C WBQTUTZNKDRZPA-UHFFFAOYSA-N 0.000 claims description 2
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- PGRDPZRUITUCAP-UHFFFAOYSA-N FC1=CC=C(C=C1)NC=1N(N=C2C=1C(N(C=1N2CC(N=1)(C)C)C)=O)CC=1C=NC=CC=1 Chemical compound FC1=CC=C(C=C1)NC=1N(N=C2C=1C(N(C=1N2CC(N=1)(C)C)C)=O)CC=1C=NC=CC=1 PGRDPZRUITUCAP-UHFFFAOYSA-N 0.000 claims description 2
- QQZNSXIPVMNIHJ-UHFFFAOYSA-N OC1=CC=CC(=N1)C1=CC=C(CN2N=C3C(C(N(C=4N3CC(N=4)(C)C)C)=O)=C2C)C=C1 Chemical compound OC1=CC=CC(=N1)C1=CC=C(CN2N=C3C(C(N(C=4N3CC(N=4)(C)C)C)=O)=C2C)C=C1 QQZNSXIPVMNIHJ-UHFFFAOYSA-N 0.000 claims description 2
- VNBVOHZUUWQBIN-PKTZIBPZSA-N OC1=CC=CC(=N1)C1=CC=C(CN2N=C3C(C(N(C=4N3[C@@H]3[C@H](N=4)CCC3)C)=O)=C2NC2=CC=CC=C2)C=C1 Chemical compound OC1=CC=CC(=N1)C1=CC=C(CN2N=C3C(C(N(C=4N3[C@@H]3[C@H](N=4)CCC3)C)=O)=C2NC2=CC=CC=C2)C=C1 VNBVOHZUUWQBIN-PKTZIBPZSA-N 0.000 claims description 2
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- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 claims 2
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- 2015-08-07 EP EP15829416.5A patent/EP3177627B1/en active Active
- 2015-08-07 JP JP2017506712A patent/JP6591530B2/ja active Active
- 2015-08-07 WO PCT/US2015/044164 patent/WO2016022893A1/en not_active Ceased
- 2015-08-07 DK DK15829416.5T patent/DK3177627T3/da active
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2019
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