JP2013545811A5 - - Google Patents
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- Publication number
- JP2013545811A5 JP2013545811A5 JP2013544731A JP2013544731A JP2013545811A5 JP 2013545811 A5 JP2013545811 A5 JP 2013545811A5 JP 2013544731 A JP2013544731 A JP 2013544731A JP 2013544731 A JP2013544731 A JP 2013544731A JP 2013545811 A5 JP2013545811 A5 JP 2013545811A5
- Authority
- JP
- Japan
- Prior art keywords
- alkylene
- alkyl
- halo
- och
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 132
- -1 methyl furanyl Chemical group 0.000 claims description 78
- 150000001875 compounds Chemical class 0.000 claims description 69
- 125000005843 halogen group Chemical group 0.000 claims description 61
- 125000002947 alkylene group Chemical group 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000004076 pyridyl group Chemical group 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 10
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 10
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 8
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 8
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical group C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 8
- 239000012964 benzotriazole Chemical group 0.000 claims description 8
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 8
- 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 description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 8
- 150000003536 tetrazoles Chemical group 0.000 claims description 8
- 150000003852 triazoles Chemical group 0.000 claims description 8
- 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 description 8
- 239000005541 ACE inhibitor Substances 0.000 claims description 7
- 239000002934 diuretic Substances 0.000 claims description 7
- PRQUBDQDCAULSW-UHFFFAOYSA-N 2-(2h-triazol-4-yl)pyridine Chemical compound N1N=NC(C=2N=CC=CC=2)=C1 PRQUBDQDCAULSW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 6
- 229940125364 angiotensin receptor blocker Drugs 0.000 claims description 6
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 6
- 239000002792 enkephalinase inhibitor Substances 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 6
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 206010019280 Heart failures Diseases 0.000 claims description 5
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 230000001882 diuretic effect Effects 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- 208000017169 kidney disease Diseases 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 108020001621 Natriuretic Peptide Proteins 0.000 claims description 4
- 102000004571 Natriuretic peptide Human genes 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000674 adrenergic antagonist Substances 0.000 claims description 4
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 4
- 239000000400 angiotensin II type 1 receptor blocker Substances 0.000 claims description 4
- 239000003146 anticoagulant agent Substances 0.000 claims description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 230000009977 dual effect Effects 0.000 claims description 4
- 239000003119 guanylate cyclase activator Substances 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 239000000692 natriuretic peptide Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229940044551 receptor antagonist Drugs 0.000 claims description 4
- 239000002464 receptor antagonist Substances 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- 239000005557 antagonist Substances 0.000 claims description 3
- 230000001142 anti-diarrhea Effects 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000003195 sodium channel blocking agent Substances 0.000 claims description 3
- 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 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical group C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 2
- 108010005094 Advanced Glycation End Products Proteins 0.000 claims description 2
- 229940123338 Aldosterone synthase inhibitor Drugs 0.000 claims description 2
- 101800000733 Angiotensin-2 Proteins 0.000 claims description 2
- 102400000345 Angiotensin-2 Human genes 0.000 claims description 2
- 102100030988 Angiotensin-converting enzyme Human genes 0.000 claims description 2
- 102100035765 Angiotensin-converting enzyme 2 Human genes 0.000 claims description 2
- 108090000975 Angiotensin-converting enzyme 2 Proteins 0.000 claims description 2
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims description 2
- 229940122155 Bradykinin receptor antagonist Drugs 0.000 claims description 2
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims description 2
- 229940127291 Calcium channel antagonist Drugs 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229940119334 Chymase inhibitor Drugs 0.000 claims description 2
- 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 description 2
- 229940097420 Diuretic Drugs 0.000 claims description 2
- 229940122783 Endothelin converting-enzyme inhibitor Drugs 0.000 claims description 2
- 229940118365 Endothelin receptor antagonist Drugs 0.000 claims description 2
- 229940127406 Estrogen Receptor Agonists Drugs 0.000 claims description 2
- 229940102550 Estrogen receptor antagonist Drugs 0.000 claims description 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 2
- 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 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims description 2
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical class O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 2
- 102000003840 Opioid Receptors Human genes 0.000 claims description 2
- 108090000137 Opioid Receptors Proteins 0.000 claims description 2
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- 229940127473 Prostaglandin Receptor Agonists Drugs 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- 102000007637 Soluble Guanylyl Cyclase Human genes 0.000 claims description 2
- 108010007205 Soluble Guanylyl Cyclase Proteins 0.000 claims description 2
- 229940123445 Tricyclic antidepressant Drugs 0.000 claims description 2
- 239000012190 activator Substances 0.000 claims description 2
- 229940121359 adenosine receptor antagonist Drugs 0.000 claims description 2
- 239000000048 adrenergic agonist Substances 0.000 claims description 2
- 239000000951 adrenergic alpha-1 receptor antagonist Substances 0.000 claims description 2
- 239000000332 adrenergic beta-1 receptor antagonist Substances 0.000 claims description 2
- 229940126157 adrenergic receptor agonist Drugs 0.000 claims description 2
- 239000002170 aldosterone antagonist Substances 0.000 claims description 2
- 229940083712 aldosterone antagonist Drugs 0.000 claims description 2
- 102000004305 alpha Adrenergic Receptors Human genes 0.000 claims description 2
- 108090000861 alpha Adrenergic Receptors Proteins 0.000 claims description 2
- 239000003098 androgen Substances 0.000 claims description 2
- 229950006323 angiotensin ii Drugs 0.000 claims description 2
- 229940127219 anticoagulant drug Drugs 0.000 claims description 2
- 239000003472 antidiabetic agent Substances 0.000 claims description 2
- 229940125708 antidiabetic agent Drugs 0.000 claims description 2
- 239000003793 antidiarrheal agent Substances 0.000 claims description 2
- 229940125714 antidiarrheal agent Drugs 0.000 claims description 2
- 239000000030 antiglaucoma agent Substances 0.000 claims description 2
- 239000003965 antinociceptive agent Substances 0.000 claims description 2
- 229960004676 antithrombotic agent Drugs 0.000 claims description 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 claims description 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000003152 bradykinin antagonist Substances 0.000 claims description 2
- 239000000480 calcium channel blocker Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000003601 chymase inhibitor Substances 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 229960005156 digoxin Drugs 0.000 claims description 2
- 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 description 2
- 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 description 2
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000002857 endothelin converting enzyme inhibitor Substances 0.000 claims description 2
- 239000002308 endothelin receptor antagonist Substances 0.000 claims description 2
- 239000000262 estrogen Substances 0.000 claims description 2
- 229940011871 estrogen Drugs 0.000 claims description 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
- 230000000407 monoamine reuptake Effects 0.000 claims description 2
- 229940035363 muscle relaxants Drugs 0.000 claims description 2
- 239000003158 myorelaxant agent Substances 0.000 claims description 2
- 239000002840 nitric oxide donor Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims description 2
- 150000003180 prostaglandins Chemical class 0.000 claims description 2
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000018 receptor agonist Substances 0.000 claims description 2
- 229940044601 receptor agonist Drugs 0.000 claims description 2
- 239000002461 renin inhibitor Substances 0.000 claims description 2
- 229940086526 renin-inhibitors Drugs 0.000 claims description 2
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims description 2
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical group C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 2
- 229930192474 thiophene Chemical group 0.000 claims description 2
- 239000003029 tricyclic antidepressant agent Substances 0.000 claims description 2
- 229960005486 vaccine Drugs 0.000 claims description 2
- 239000002536 vasopressin receptor antagonist Substances 0.000 claims description 2
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical group C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 229960004773 losartan Drugs 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002051 C09CA08 - Olmesartan medoxomil Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 description 3
- 229960004349 candesartan cilexetil Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229960001199 olmesartan medoxomil Drugs 0.000 description 3
- WJXAVNPIJIPGMN-PNGYUKAISA-N (2s)-2-[[(2s)-1-[(2s)-2-[[(2s,3s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-5-(diaminomethylideneamino)-2-[[2-(methylamino)acetyl]amino]pentanoyl]amino]-3-methylbutanoyl]amino]-3-(4-methoxyphenyl)propanoyl]amino]-3-methylpentanoyl]amino]-3-(1h-imidazol-5-yl)propanoyl]py 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](CCCN=C(N)N)NC(=O)CNC)C(C)C)C1=CC=C(OC)C=C1 WJXAVNPIJIPGMN-PNGYUKAISA-N 0.000 description 2
- JIVPVXMEBJLZRO-CQSZACIVSA-N 2-chloro-5-[(1r)-1-hydroxy-3-oxo-2h-isoindol-1-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC([C@@]2(O)C3=CC=CC=C3C(=O)N2)=C1 JIVPVXMEBJLZRO-CQSZACIVSA-N 0.000 description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 2
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| CN100518998C (zh) * | 2005-09-29 | 2009-07-29 | 宝山钢铁股份有限公司 | 薄带连铸结晶辊加热方法和装置 |
| CA2819153A1 (en) | 2010-12-15 | 2012-06-21 | Theravance, Inc. | Neprilysin inhibitors |
| HUE028051T2 (hu) | 2010-12-15 | 2016-11-28 | Theravance Biopharma R&D Ip Llc | Neprilizin inhibitorok |
| JP5959065B2 (ja) | 2011-02-17 | 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としての置換アミノ酪酸誘導体 |
| JP5959066B2 (ja) * | 2011-02-17 | 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としての置換アミノ酪酸誘導体 |
| CN103582630B (zh) | 2011-05-31 | 2016-08-17 | 施万生物制药研发Ip有限责任公司 | 脑啡肽酶抑制剂 |
| 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 |
| TWI560172B (en) | 2011-11-02 | 2016-12-01 | Theravance Biopharma R&D Ip Llc | Neprilysin inhibitors |
| WO2013148768A1 (en) | 2012-03-28 | 2013-10-03 | Theravance, Inc. | Crystalline forms of (r)-3-[n-(3'-chlorobiphenyl-4-ylmethyl)-n'-(3-hydroxyisoxazole-5-carbonyl)hydrazino]-2-hydroxypropionic acid isopropyl ester |
| CA2871292A1 (en) | 2012-05-31 | 2013-12-05 | Theravance Biopharma R&D Ip, Llc | Nitric oxide donor neprilysin inhibitors |
| WO2013184898A1 (en) | 2012-06-08 | 2013-12-12 | Theravance, Inc. | Neprilysin inhibitors |
| SMT201700306T1 (it) | 2012-06-08 | 2017-07-18 | Theravance Biopharma R&D Ip Llc | Inibitori di neprilisina |
| MX366149B (es) | 2012-08-08 | 2019-06-28 | Theravance Biopharma R&D Ip Llc | Inhibidores de neprilisina. |
| DK2964616T3 (en) | 2013-03-05 | 2017-08-28 | Theravance Biopharma R&D Ip Llc | Neprilysin inhibitors |
| CA2934936A1 (en) | 2014-01-30 | 2015-08-06 | Theravance Biopharma R&D Ip, Llc | Neprilysin inhibitors |
| CA2934898A1 (en) | 2014-01-30 | 2015-08-06 | Theravance Biopharma R&D Ip, Llc | 5-biphenyl-4-heteroarylcarbonylamino-pentanoic acid derivatives as neprilysin inhibitors |
| JP6766055B2 (ja) | 2015-02-11 | 2020-10-07 | 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としての（２ｓ，４ｒ）−５−（５’−クロロ−２’−フルオロビフェニル−４−イル）−４−（エトキシオキサリルアミノ）−２−ヒドロキシメチル−２−メチルペンタン酸 |
| LT3259255T (lt) | 2015-02-19 | 2021-04-26 | Theravance Biopharma R&D Ip, Llc | (2r,4r)-5-(5`-chlor-2`-fluorbifenil-4-il)-2-hidroksi-4-[(5-metiloksazol-2-karbonil)amino]pentano rūgštis |
| JP7306828B2 (ja) | 2016-03-08 | 2023-07-11 | 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 | 結晶性（２ｓ，４ｒ）－５－（５’－クロロ－２’－フルオロ－［１，１’－ビフェニル］－４－イル）－２－（エトキシメチル）－４－（３－ヒドロキシイソオキサゾール－５－カルボキサミド）－２－メチルペンタン酸およびその使用 |
| US11993590B2 (en) | 2016-12-04 | 2024-05-28 | 712 North Inc. | Pyranone compounds useful to modulate OMA1 protease |
| EP3548039B1 (en) | 2016-12-04 | 2023-07-19 | Alavi Khorassani Moghadam, Marcel Victor | Ribavirin for use in the treatment of a mitochondrial disease |
| CA3087557C (en) | 2018-01-03 | 2025-06-17 | Ecolab Usa Inc. | Benzotriazole derivatives as corrosion inhibitors |
| UY38072A (es) | 2018-02-07 | 2019-10-01 | Novartis Ag | Compuestos derivados de éster butanoico sustituido con bisfenilo como inhibidores de nep, composiciones y combinaciones de los mismos |
Family Cites Families (48)
| 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 |
| 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 |
| US5294632A (en) | 1991-05-01 | 1994-03-15 | Ciba-Geigy Corporation | Phosphono/biaryl substituted dipetide derivatives |
| US5155100A (en) | 1991-05-01 | 1992-10-13 | Ciba-Geigy Corporation | Phosphono/biaryl substituted dipeptide 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 |
| US5977075A (en) | 1995-04-21 | 1999-11-02 | Novartis Ag | N-aroylamino acid amides as endothelin inhibitors |
| 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 |
| EA014191B1 (ru) * | 2003-06-24 | 2010-10-29 | Юнироял Кемикал Компани, Инк. | Фунгицидные феноксифенилгидразиновые производные |
| WO2006027680A1 (en) | 2004-09-10 | 2006-03-16 | Pfizer Limited | 3-(1-carbamoylcyclohexyl) propionic acid derivatives as inhibitors of neutral endopeptidase enzyme |
| CA2594395A1 (en) * | 2005-02-10 | 2006-08-17 | Medivir Ab | Hiv protease inhibitors |
| 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 |
| PH12012502091A1 (en) | 2007-01-12 | 2019-06-14 | Novartis Ag | Process for preparing 5-biphenyl-4-amino-2-methyl pentanoic acid |
| TWI448284B (zh) | 2007-04-24 | 2014-08-11 | Theravance Inc | 雙效抗高血壓劑 |
| 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 |
| JP5466759B2 (ja) | 2009-05-28 | 2014-04-09 | ノバルティス アーゲー | ネプリライシン阻害剤としての置換アミノ酪酸誘導体 |
| SG176009A1 (en) * | 2009-05-28 | 2011-12-29 | Novartis Ag | Substituted aminopropionic derivatives as neprilysin inhibitors |
| JO2967B1 (en) | 2009-11-20 | 2016-03-15 | نوفارتس ايه جي | Acetic acid derivatives of carbamoyl methyl amino are substituted as new NEP inhibitors |
| AU2011207020B2 (en) | 2010-01-22 | 2014-04-17 | Novartis Ag | Intermediates of neutral endopeptidase inhibitors and preparation method thereof |
| US8673974B2 (en) | 2010-11-16 | 2014-03-18 | Novartis Ag | Substituted amino bisphenyl pentanoic acid derivatives as NEP inhibitors |
| US8993631B2 (en) | 2010-11-16 | 2015-03-31 | Novartis Ag | Method of treating contrast-induced nephropathy |
| CA2819153A1 (en) | 2010-12-15 | 2012-06-21 | Theravance, Inc. | Neprilysin inhibitors |
| HUE028051T2 (hu) | 2010-12-15 | 2016-11-28 | Theravance Biopharma R&D Ip Llc | Neprilizin inhibitorok |
| JP5959065B2 (ja) * | 2011-02-17 | 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としての置換アミノ酪酸誘導体 |
| JP5959066B2 (ja) * | 2011-02-17 | 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としての置換アミノ酪酸誘導体 |
| CN103748070B (zh) | 2011-05-31 | 2015-06-24 | 施万生物制药研发Ip有限责任公司 | 脑啡肽酶抑制剂 |
| 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 |
| CN103582630B (zh) | 2011-05-31 | 2016-08-17 | 施万生物制药研发Ip有限责任公司 | 脑啡肽酶抑制剂 |
| TWI560172B (en) | 2011-11-02 | 2016-12-01 | Theravance Biopharma R&D Ip Llc | Neprilysin inhibitors |
| WO2013148768A1 (en) | 2012-03-28 | 2013-10-03 | Theravance, Inc. | Crystalline forms of (r)-3-[n-(3'-chlorobiphenyl-4-ylmethyl)-n'-(3-hydroxyisoxazole-5-carbonyl)hydrazino]-2-hydroxypropionic acid isopropyl ester |
| CA2871292A1 (en) | 2012-05-31 | 2013-12-05 | Theravance Biopharma R&D Ip, Llc | Nitric oxide donor neprilysin inhibitors |
| SMT201700306T1 (it) | 2012-06-08 | 2017-07-18 | Theravance Biopharma R&D Ip Llc | Inibitori di neprilisina |
| WO2013184898A1 (en) | 2012-06-08 | 2013-12-12 | Theravance, Inc. | Neprilysin inhibitors |
| MX366149B (es) | 2012-08-08 | 2019-06-28 | Theravance Biopharma R&D Ip Llc | Inhibidores de neprilisina. |
-
2011
- 2011-12-14 CA CA2819153A patent/CA2819153A1/en not_active Abandoned
- 2011-12-14 JP JP2013544731A patent/JP5944922B2/ja not_active Expired - Fee Related
- 2011-12-14 CN CN201180060322.XA patent/CN103261168B/zh not_active Expired - Fee Related
- 2011-12-14 RU RU2013132524/04A patent/RU2605557C2/ru not_active IP Right Cessation
- 2011-12-14 SG SG2013046107A patent/SG191175A1/en unknown
- 2011-12-14 AR ARP110104683 patent/AR084290A1/es unknown
- 2011-12-14 US US13/325,453 patent/US8563512B2/en not_active Expired - Fee Related
- 2011-12-14 MX MX2013006802A patent/MX354476B/es active IP Right Grant
- 2011-12-14 EP EP11805709.0A patent/EP2651900B1/en active Active
- 2011-12-14 KR KR1020137018340A patent/KR101892611B1/ko not_active Expired - Fee Related
- 2011-12-14 AU AU2011343903A patent/AU2011343903B2/en not_active Ceased
- 2011-12-14 ES ES11805709.0T patent/ES2548887T3/es active Active
- 2011-12-14 NZ NZ611528A patent/NZ611528A/en not_active IP Right Cessation
- 2011-12-14 WO PCT/US2011/064837 patent/WO2012082857A1/en not_active Ceased
- 2011-12-14 BR BR112013014952A patent/BR112013014952A2/pt not_active Application Discontinuation
- 2011-12-15 TW TW100146635A patent/TWI523843B/zh not_active IP Right Cessation
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2013
- 2013-05-20 IL IL226451A patent/IL226451A/en active IP Right Grant
- 2013-06-07 ZA ZA2013/04208A patent/ZA201304208B/en unknown
- 2013-09-12 US US14/024,974 patent/US9120758B2/en active Active
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2015
- 2015-07-21 US US14/804,407 patent/US9555041B2/en not_active Expired - Fee Related
- 2015-09-24 JP JP2015186388A patent/JP2015232044A/ja not_active Withdrawn
-
2016
- 2016-12-14 US US15/379,188 patent/US9873696B2/en not_active Expired - Fee Related
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