JP2014528903A5 - - Google Patents
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- JP2014528903A5 JP2014528903A5 JP2014513549A JP2014513549A JP2014528903A5 JP 2014528903 A5 JP2014528903 A5 JP 2014528903A5 JP 2014513549 A JP2014513549 A JP 2014513549A JP 2014513549 A JP2014513549 A JP 2014513549A JP 2014528903 A5 JP2014528903 A5 JP 2014528903A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkylene
- coor
- compound
- phenyl
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 39
- -1 —O-benzyl Chemical group 0.000 claims description 29
- 239000002934 diuretic Substances 0.000 claims description 7
- 239000005541 ACE inhibitor Substances 0.000 claims description 5
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 5
- 229940125364 angiotensin receptor blocker Drugs 0.000 claims description 5
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 5
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 5
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 5
- 239000000400 angiotensin II type 1 receptor blocker Substances 0.000 claims description 4
- 230000001882 diuretic effect Effects 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 3
- 239000002464 receptor antagonist Substances 0.000 claims description 3
- 229940044551 receptor antagonist Drugs 0.000 claims description 3
- 230000001142 anti-diarrhea Effects 0.000 claims description 2
- 239000003195 sodium channel blocking agent Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 71
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 19
- 125000005843 halogen group Chemical group 0.000 claims 17
- 125000002947 alkylene group Chemical group 0.000 claims 16
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 229930192474 thiophene Natural products 0.000 claims 6
- 238000005859 coupling reaction Methods 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- OMJKVIFSWSQTGQ-UHFFFAOYSA-N 6,7-bis(aziridin-1-yl)quinazoline-5,8-dione Chemical compound C1CN1C=1C(=O)C2=NC=NC=C2C(=O)C=1N1CC1 OMJKVIFSWSQTGQ-UHFFFAOYSA-N 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 4
- 150000003536 tetrazoles Chemical class 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 229940125904 compound 1 Drugs 0.000 claims 3
- 230000008878 coupling Effects 0.000 claims 3
- 238000010168 coupling process Methods 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 239000002792 enkephalinase inhibitor Substances 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 108020001621 Natriuretic Peptide Proteins 0.000 claims 2
- 102000004571 Natriuretic peptide Human genes 0.000 claims 2
- 239000000674 adrenergic antagonist Substances 0.000 claims 2
- 239000003146 anticoagulant agent Substances 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 229940126214 compound 3 Drugs 0.000 claims 2
- 229940125898 compound 5 Drugs 0.000 claims 2
- 230000009977 dual effect Effects 0.000 claims 2
- 239000003119 guanylate cyclase activator Substances 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000000692 natriuretic peptide Substances 0.000 claims 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- MYKISKNCSHSDLC-UHFFFAOYSA-N 1,2,3,4-tetrahydrothieno[3,2-d]pyrimidine Chemical compound N1CNCC2=C1C=CS2 MYKISKNCSHSDLC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical compound C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 claims 1
- QZDDFQLIQRYMBV-UHFFFAOYSA-N 2-[3-nitro-2-(2-nitrophenyl)-4-oxochromen-8-yl]acetic acid Chemical compound OC(=O)CC1=CC=CC(C(C=2[N+]([O-])=O)=O)=C1OC=2C1=CC=CC=C1[N+]([O-])=O QZDDFQLIQRYMBV-UHFFFAOYSA-N 0.000 claims 1
- LIJKMAJUPBLKRC-IEBWSBKVSA-N 2-[4-[[(1r,2r)-1-carboxy-1-hydroxy-3-[2-(trifluoromethyl)phenyl]propan-2-yl]amino]-4-oxobutyl]benzoic acid Chemical compound C([C@H]([C@@H](O)C(O)=O)NC(=O)CCCC=1C(=CC=CC=1)C(O)=O)C1=CC=CC=C1C(F)(F)F LIJKMAJUPBLKRC-IEBWSBKVSA-N 0.000 claims 1
- MOIHTQJUOMEIMX-IEBWSBKVSA-N 2-[4-[[(1r,2r)-1-carboxy-3-(2-chlorophenyl)-1-hydroxypropan-2-yl]amino]-4-oxobutyl]-4-fluorobenzoic acid Chemical compound C([C@H]([C@@H](O)C(O)=O)NC(=O)CCCC=1C(=CC=C(F)C=1)C(O)=O)C1=CC=CC=C1Cl MOIHTQJUOMEIMX-IEBWSBKVSA-N 0.000 claims 1
- LVYHNSMAIXDTGG-IEBWSBKVSA-N 2-[4-[[(1r,2r)-1-carboxy-3-(2-chlorophenyl)-1-hydroxypropan-2-yl]amino]-4-oxobutyl]benzoic acid Chemical compound C([C@H]([C@@H](O)C(O)=O)NC(=O)CCCC=1C(=CC=CC=1)C(O)=O)C1=CC=CC=C1Cl LVYHNSMAIXDTGG-IEBWSBKVSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 108010005094 Advanced Glycation End Products Proteins 0.000 claims 1
- 229940123338 Aldosterone synthase inhibitor Drugs 0.000 claims 1
- 102400000345 Angiotensin-2 Human genes 0.000 claims 1
- 101800000733 Angiotensin-2 Proteins 0.000 claims 1
- 102100030988 Angiotensin-converting enzyme Human genes 0.000 claims 1
- 102100035765 Angiotensin-converting enzyme 2 Human genes 0.000 claims 1
- 108090000975 Angiotensin-converting enzyme 2 Proteins 0.000 claims 1
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims 1
- 229940122155 Bradykinin receptor antagonist Drugs 0.000 claims 1
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims 1
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 claims 1
- 229940097420 Diuretic Drugs 0.000 claims 1
- 229940122783 Endothelin converting-enzyme inhibitor Drugs 0.000 claims 1
- 229940118365 Endothelin receptor antagonist Drugs 0.000 claims 1
- 229940127406 Estrogen Receptor Agonists Drugs 0.000 claims 1
- 229940102550 Estrogen receptor antagonist Drugs 0.000 claims 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 claims 1
- 229940099433 NMDA receptor antagonist Drugs 0.000 claims 1
- 229940121954 Opioid receptor agonist Drugs 0.000 claims 1
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 claims 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims 1
- 229940127473 Prostaglandin Receptor Agonists Drugs 0.000 claims 1
- 102000007637 Soluble Guanylyl Cyclase Human genes 0.000 claims 1
- 108010007205 Soluble Guanylyl Cyclase Proteins 0.000 claims 1
- 229940123445 Tricyclic antidepressant Drugs 0.000 claims 1
- GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 claims 1
- 108010004977 Vasopressins Proteins 0.000 claims 1
- 102000002852 Vasopressins Human genes 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
- 229940121359 adenosine receptor antagonist Drugs 0.000 claims 1
- 239000000048 adrenergic agonist Substances 0.000 claims 1
- 239000000951 adrenergic alpha-1 receptor antagonist Substances 0.000 claims 1
- 239000000332 adrenergic beta-1 receptor antagonist Substances 0.000 claims 1
- 229940126157 adrenergic receptor agonist Drugs 0.000 claims 1
- 239000002170 aldosterone antagonist Substances 0.000 claims 1
- 229940083712 aldosterone antagonist Drugs 0.000 claims 1
- 102000004305 alpha Adrenergic Receptors Human genes 0.000 claims 1
- 108090000861 alpha Adrenergic Receptors Proteins 0.000 claims 1
- 239000003098 androgen Substances 0.000 claims 1
- 229950006323 angiotensin ii Drugs 0.000 claims 1
- 229940127219 anticoagulant drug Drugs 0.000 claims 1
- 239000003472 antidiabetic agent Substances 0.000 claims 1
- 229940125708 antidiabetic agent Drugs 0.000 claims 1
- 239000003793 antidiarrheal agent Substances 0.000 claims 1
- 229940125714 antidiarrheal agent Drugs 0.000 claims 1
- 239000000030 antiglaucoma agent Substances 0.000 claims 1
- 239000003965 antinociceptive agent Substances 0.000 claims 1
- 229960004676 antithrombotic agent Drugs 0.000 claims 1
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 claims 1
- 125000005002 aryl methyl group Chemical group 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 claims 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000003152 bradykinin antagonist Substances 0.000 claims 1
- 239000000480 calcium channel blocker Substances 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- 230000000593 degrading effect Effects 0.000 claims 1
- LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 claims 1
- 229960005156 digoxin Drugs 0.000 claims 1
- LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 claims 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000000386 donor Substances 0.000 claims 1
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000002857 endothelin converting enzyme inhibitor Substances 0.000 claims 1
- 239000002308 endothelin receptor antagonist Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000000262 estrogen Substances 0.000 claims 1
- 229940011871 estrogen Drugs 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000000407 monoamine reuptake Effects 0.000 claims 1
- 229940035363 muscle relaxants Drugs 0.000 claims 1
- 239000003158 myorelaxant agent Substances 0.000 claims 1
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000003402 opiate agonist Substances 0.000 claims 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 150000003180 prostaglandins Chemical class 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 claims 1
- 239000002461 renin inhibitor Substances 0.000 claims 1
- 229940086526 renin-inhibitors Drugs 0.000 claims 1
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims 1
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 150000003577 thiophenes Chemical class 0.000 claims 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 claims 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical group CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 claims 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 229960005486 vaccine Drugs 0.000 claims 1
- 229960003726 vasopressin Drugs 0.000 claims 1
- 239000002083 C09CA01 - Losartan Substances 0.000 description 4
- GHOSNRCGJFBJIB-UHFFFAOYSA-N Candesartan cilexetil Chemical compound C=12N(CC=3C=CC(=CC=3)C=3C(=CC=CC=3)C3=NNN=N3)C(OCC)=NC2=CC=CC=1C(=O)OC(C)OC(=O)OC1CCCCC1 GHOSNRCGJFBJIB-UHFFFAOYSA-N 0.000 description 4
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
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- RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 description 4
- 239000002051 C09CA08 - Olmesartan medoxomil Substances 0.000 description 3
- UQGKUQLKSCSZGY-UHFFFAOYSA-N Olmesartan medoxomil Chemical compound C=1C=C(C=2C(=CC=CC=2)C2=NNN=N2)C=CC=1CN1C(CCC)=NC(C(C)(C)O)=C1C(=O)OCC=1OC(=O)OC=1C UQGKUQLKSCSZGY-UHFFFAOYSA-N 0.000 description 3
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- 108010061435 Enalapril Proteins 0.000 description 2
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 2
- SBDNJUWAMKYJOX-UHFFFAOYSA-N Meclofenamic Acid Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C(O)=O)=C1Cl SBDNJUWAMKYJOX-UHFFFAOYSA-N 0.000 description 2
- ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 description 2
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 2
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 2
- MITFXPHMIHQXPI-UHFFFAOYSA-N Oraflex Chemical compound N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 2
- 108700028065 Sar(1)-Me-Tyr(4)- angiotensin II Proteins 0.000 description 2
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Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112013014952A2 (pt) | 2010-12-15 | 2017-05-30 | Theravance Inc | inibidores de neprilisina |
| HRP20151115T1 (en) | 2010-12-15 | 2015-11-20 | Theravance Biopharma R&D Ip, Llc | Neprilysin inhibitors |
| WO2012154249A1 (en) | 2011-02-17 | 2012-11-15 | Theravance, Inc. | Substituted aminobutyric derivatives as neprilysin inhibitors |
| EP2675795B1 (en) | 2011-02-17 | 2016-04-20 | Theravance Biopharma R&D IP, LLC | Substituted aminobutyric derivatives as neprilysin inhibitors |
| JP5959074B2 (ja) | 2011-05-31 | 2016-08-02 | セラヴァンス バイオファーマ アール＆ディー アイピー， エルエルシー | ネプリライシン阻害剤 |
| EP2714660B1 (en) | 2011-05-31 | 2018-09-26 | Theravance Biopharma R&D IP, LLC | Neprilysin inhibitors |
| TWI560172B (en) | 2011-11-02 | 2016-12-01 | Theravance Biopharma R&D Ip Llc | Neprilysin inhibitors |
| US9210438B2 (en) | 2012-01-20 | 2015-12-08 | Sony Corporation | Logical intra mode naming in HEVC video coding |
| CN104350052B (zh) | 2012-05-31 | 2017-05-31 | 施万生物制药研发Ip有限责任公司 | 一氧化氮供体脑啡肽酶抑制剂 |
| RS55967B1 (sr) | 2012-06-08 | 2017-09-29 | Theravance Biopharma R&D Ip Llc | Inhibitori neprilizina |
| CA2873328A1 (en) | 2012-06-08 | 2013-12-12 | Theravance Biopharma R&D Ip, Llc | Neprilysin inhibitors |
| SMT201700134T1 (it) | 2012-08-08 | 2017-05-08 | Theravance Biopharma R&D Ip Llc | Inibitori della neprilisina |
| TW201444798A (zh) | 2013-02-28 | 2014-12-01 | 必治妥美雅史谷比公司 | 作爲強效ｒｏｃｋ１及ｒｏｃｋ２抑制劑之苯基吡唑衍生物 |
| JP6423372B2 (ja) | 2013-02-28 | 2018-11-14 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 強力なｒｏｃｋ１およびｒｏｃｋ２阻害剤としてのフェニルピラゾール誘導体 |
| WO2014138053A1 (en) | 2013-03-05 | 2014-09-12 | Theravance Biopharma R&D Ip, Llc | Neprilysin inhibitors |
| SG11201606057PA (en) | 2014-01-30 | 2016-08-30 | Theravance Biopharma R&D Ip Llc | 5-biphenyl-4-heteroarylcarbonylamino-pentanoic acid derivatives as neprilysin inhibitors |
| CN105992763A (zh) | 2014-01-30 | 2016-10-05 | 施万生物制药研发Ip有限责任公司 | 脑啡肽酶抑制剂 |
| RU2726623C2 (ru) | 2015-02-11 | 2020-07-15 | ТЕРЕВАНС БАЙОФАРМА Ар энд Ди АйПи, ЭлЭлСи | (2s,4r)-5-(5'-хлор-2'-фторбифенил-4-ил)-4-(этоксиоксалиламино)-2-гидроксиметил-2-метилпентановая кислота |
| RU2715241C2 (ru) | 2015-02-19 | 2020-02-26 | ТЕРЕВАНС БАЙОФАРМА Ар энд Ди АйПи, ЭлЭлСи | (2r,4r)-5-(5′-хлор-2′-фторбифенил-4-ил)-2-гидрокси-4-[(5-метилоксазол-2-карбонил)амино]пентановая кислота |
| US10100021B2 (en) | 2016-03-08 | 2018-10-16 | Theravance Biopharma R&D Ip, Llc | Crystalline(2S,4R)-5-(5′-chloro-2′-fluoro-[1,1′-biphenyl]-4-yl)-2-(ethoxymethyl)-4-(3-hydroxyisoxazole-5-carboxamido)-2-methylpentanoic acid and uses thereof |
| WO2020110008A1 (en) | 2018-11-27 | 2020-06-04 | Novartis Ag | Cyclic pentamer compounds as proprotein convertase subtilisin/kexin type 9 (pcsk9) inhibitors for the treatment of metabolic disorder |
| UY38485A (es) | 2018-11-27 | 2020-06-30 | Novartis Ag | Compuestos tetrámeros cíclicos como inhibidores de proproteína convertasa subtilisina/kexina tipo 9 (pcsk9), método de tratamiento, uso y su preparación |
| CN113166204B (zh) | 2018-11-27 | 2025-01-28 | 诺华股份有限公司 | 作为治疗代谢障碍的蛋白质原转换酶枯草杆菌蛋白酶/kexin 9型（PCSK9）抑制剂的环状肽 |
| TW202333563A (zh) | 2021-11-12 | 2023-09-01 | 瑞士商諾華公司 | 用於治療疾病或障礙之二胺基環戊基吡啶衍生物 |
| EP4516778A1 (en) * | 2022-04-25 | 2025-03-05 | Nippon Shinyaku Co., Ltd. | Compound serving as ddr1 kinase inhibitor, and medicine |
Family Cites Families (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4189604A (en) | 1975-07-22 | 1980-02-19 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Bestatin |
| US4206232A (en) | 1976-05-10 | 1980-06-03 | E. R. Squibb & Sons, Inc. | Relieving hypertension with carboxyalkylacylamino acids |
| IL58849A (en) | 1978-12-11 | 1983-03-31 | Merck & Co Inc | Carboxyalkyl dipeptides and derivatives thereof,their preparation and pharmaceutical compositions containing them |
| JPS55355A (en) * | 1979-03-09 | 1980-01-05 | Nippon Kayaku Co Ltd | Preparation of (2s,3r) or (2s,3s)-3-amino-2-hyroxypropionic acid derivative |
| FR2480747A1 (fr) | 1980-04-17 | 1981-10-23 | Roques Bernard | Derives d'acides amines et leur application therapeutique |
| US4906615A (en) | 1980-12-18 | 1990-03-06 | Schering Corporation | Substituted dipeptides as inhibitors of enkephalinases |
| US4722810A (en) | 1984-08-16 | 1988-02-02 | E. R. Squibb & Sons, Inc. | Enkephalinase inhibitors |
| US4939261A (en) | 1984-06-08 | 1990-07-03 | Ciba-Geigy Corporation | N-substituted butyramide derivatives useful for treatment of conditions responsive to inhibition of enkephalinase |
| EP0225292A3 (en) | 1985-12-06 | 1988-11-30 | Ciba-Geigy Ag | Certain n-substituted butyramide derivatives |
| US4929641B1 (en) | 1988-05-11 | 1994-08-30 | Schering Corp | Mercapto-acylamino acid antihypertensives |
| KR880007441A (ko) | 1986-12-11 | 1988-08-27 | 알렌 제이.스피겔 | 스피로-치환된 글루타르아미드 이뇨제 |
| FR2623498B1 (fr) | 1987-11-24 | 1990-04-06 | Bioprojet Soc Civ | Nouveaux composes enantiomeres derives d'amino-acides, leur procede de preparation et leurs applications therapeutiques |
| GB8820844D0 (en) | 1988-09-05 | 1988-10-05 | Pfizer Ltd | Therapeutic agents |
| US5599951A (en) | 1989-09-15 | 1997-02-04 | Societe Civile Bioprojet | Amino acid derivatives, the process for their preparation and their applications to therapy |
| US5155100A (en) | 1991-05-01 | 1992-10-13 | Ciba-Geigy Corporation | Phosphono/biaryl substituted dipeptide derivatives |
| US5294632A (en) | 1991-05-01 | 1994-03-15 | Ciba-Geigy Corporation | Phosphono/biaryl substituted dipetide derivatives |
| US5217996A (en) | 1992-01-22 | 1993-06-08 | Ciba-Geigy Corporation | Biaryl substituted 4-amino-butyric acid amides |
| US5508272A (en) | 1993-06-15 | 1996-04-16 | Bristol-Myers Squibb Company | Compounds containing a fused bicycle ring and processes therefor |
| DE19510566A1 (de) | 1995-03-23 | 1996-09-26 | Kali Chemie Pharma Gmbh | Benzazepin-, Benzoxazepin- und Benzothiazepin-N-essigsäurederivate sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| EP0821670A1 (en) | 1995-04-21 | 1998-02-04 | Novartis AG | N-aroylamino acid amides as endothelin inhibitors |
| FI974437A0 (fi) | 1995-06-06 | 1997-12-05 | Pfizer | Substituoituja N-(indoli-2-karbonyyli)amideja ja johdannaisia glykogeenifosforylaasi-inhibiittoreina |
| CA2179935C (en) * | 1995-06-30 | 2010-09-07 | Ryohei Kato | Novel dipeptide compound or pharmaceutically acceptable salt thereof and medical use thereof |
| JP3408379B2 (ja) * | 1995-06-30 | 2003-05-19 | 株式会社ジャパンエナジー | 新規なジペプチド化合物又はその薬理的に許容される塩及びその医薬用途 |
| WO1999050249A2 (en) | 1998-04-01 | 1999-10-07 | Du Pont Pharmaceuticals Company | Pyrimidines and triazines as integrin antagonists |
| US6660756B2 (en) | 2001-03-28 | 2003-12-09 | Pfizer Inc. | N-phenpropylcyclopentyl-substituted glutaramide derivatives as inhibitors of neutral endopeptidase |
| GB0119305D0 (en) | 2001-04-12 | 2001-10-03 | Aventis Pharma Gmbh | Mercaptoacetylamide derivatives,a process for their preparation and their use |
| JP2004256435A (ja) * | 2003-02-26 | 2004-09-16 | Sankyo Co Ltd | ３−置換アミノ−２−ヒドロキシ−４−フェニル酪酸類 |
| EP1636224B1 (en) | 2003-05-21 | 2010-07-14 | Prosidion Limited | Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phoshorylase |
| EP1493739A1 (fr) | 2003-07-03 | 2005-01-05 | Warner-Lambert Company LLC | Dérivés thiophényliques d'aminoacides, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent |
| WO2006027680A1 (en) | 2004-09-10 | 2006-03-16 | Pfizer Limited | 3-(1-carbamoylcyclohexyl) propionic acid derivatives as inhibitors of neutral endopeptidase enzyme |
| AR057882A1 (es) | 2005-11-09 | 2007-12-26 | Novartis Ag | Compuestos de accion doble de bloqueadores del receptor de angiotensina e inhibidores de endopeptidasa neutra |
| WO2007106708A2 (en) | 2006-03-10 | 2007-09-20 | Novartis Ag | Combinations of the angiotensin ii antagonist valsartan and the nep inhibitor daglutril |
| CA2674291C (en) | 2007-01-12 | 2015-11-24 | Novartis Ag | New process |
| TWI448284B (zh) * | 2007-04-24 | 2014-08-11 | Theravance Inc | 雙效抗高血壓劑 |
| CN101896470B (zh) | 2007-12-11 | 2013-04-10 | 施万制药 | 双重作用的苯并咪唑衍生物和其作为抗高血压药剂的用途 |
| AR070176A1 (es) | 2008-01-17 | 2010-03-17 | Novartis Ag | Procesos de sintesis de inhibidores de nep, compuestos intermediarios y uso de los mismos en la sintesis |
| EP2334651A2 (en) * | 2008-07-24 | 2011-06-22 | Theravance, Inc. | Dual-acting antihypertensive agents |
| KR101096427B1 (ko) * | 2008-10-20 | 2011-12-20 | 주식회사 이큐스앤자루 | 신규한 4-아릴-4-옥소부탄산 아미드 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 약학적 조성물 |
| US8236798B2 (en) | 2009-05-07 | 2012-08-07 | Abbott Gmbh & Co. Kg | Carboxamide compounds and their use as calpain inhibitors |
| ES2523734T3 (es) | 2009-05-28 | 2014-12-01 | Novartis Ag | Derivados aminopropiónicos sustituidos como inhibidores de neprilisina |
| EP3048100A1 (en) | 2009-05-28 | 2016-07-27 | Novartis AG | Substituted aminobutyric derivatives as neprilysin inhibitors |
| US7956054B2 (en) | 2009-07-07 | 2011-06-07 | Theravance, Inc. | Dual-acting pyrazole antihypertensive agents |
| ES2441419T3 (es) | 2009-07-22 | 2014-02-04 | Theravance, Inc. | Agentes antihipertensivos de doble acción basados en oxazol |
| JO2967B1 (en) | 2009-11-20 | 2016-03-15 | نوفارتس ايه جي | Acetic acid derivatives of carbamoyl methyl amino are substituted as new NEP inhibitors |
| ES2550485T3 (es) | 2010-01-22 | 2015-11-10 | Novartis Ag | Intermedios de inhibidores de la endopeptidasa neutra y método de preparación de los mismos |
| TWI532725B (zh) | 2010-01-26 | 2016-05-11 | 賽諾菲阿凡提斯公司 | 經氧取代之３－雜芳醯基胺基－丙酸衍生物及其作為藥物之用途 |
| US8993631B2 (en) | 2010-11-16 | 2015-03-31 | Novartis Ag | Method of treating contrast-induced nephropathy |
| US8673974B2 (en) | 2010-11-16 | 2014-03-18 | Novartis Ag | Substituted amino bisphenyl pentanoic acid derivatives as NEP inhibitors |
| EP2714660B1 (en) * | 2011-05-31 | 2018-09-26 | Theravance Biopharma R&D IP, LLC | Neprilysin inhibitors |
-
2012
- 2012-05-18 CN CN201280026853.1A patent/CN103748070B/zh not_active Expired - Fee Related
- 2012-05-18 EP EP12724046.3A patent/EP2714648B1/en active Active
- 2012-05-18 US US13/475,017 patent/US8686184B2/en active Active
- 2012-05-18 JP JP2014513549A patent/JP5885832B2/ja not_active Expired - Fee Related
- 2012-05-18 WO PCT/US2012/038517 patent/WO2012166389A1/en not_active Ceased
- 2012-05-18 ES ES12724046.3T patent/ES2642883T3/es active Active
- 2012-05-18 CA CA2835281A patent/CA2835281A1/en not_active Abandoned
-
2015
- 2015-12-24 JP JP2015251113A patent/JP2016047846A/ja not_active Withdrawn
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