JP2014515401A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2014515401A5 JP2014515401A5 JP2014513547A JP2014513547A JP2014515401A5 JP 2014515401 A5 JP2014515401 A5 JP 2014515401A5 JP 2014513547 A JP2014513547 A JP 2014513547A JP 2014513547 A JP2014513547 A JP 2014513547A JP 2014515401 A5 JP2014515401 A5 JP 2014515401A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkylene
- halo
- compound
- pharmaceutically acceptable
- 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 123
- 150000001875 compounds Chemical class 0.000 claims description 62
- 125000005843 halogen group Chemical group 0.000 claims description 53
- -1 alkylene morpholine Chemical compound 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000002947 alkylene group Chemical group 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 239000005541 ACE inhibitor Substances 0.000 claims description 7
- 239000002934 diuretic Substances 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 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
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000002792 enkephalinase inhibitor Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 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
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 206010019280 Heart failures Diseases 0.000 claims description 5
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 239000002253 acid Substances 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
- 239000000203 mixture Substances 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- 108020001621 Natriuretic Peptide Proteins 0.000 claims description 4
- 102000004571 Natriuretic peptide Human genes 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-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
- 239000000400 angiotensin II type 1 receptor blocker Substances 0.000 claims description 4
- 239000003146 anticoagulant agent Substances 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229940125904 compound 1 Drugs 0.000 claims description 4
- 229940126214 compound 3 Drugs 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 230000009977 dual effect Effects 0.000 claims description 4
- 239000003119 guanylate cyclase activator Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000000692 natriuretic peptide Substances 0.000 claims description 4
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002170 aldosterone antagonist Substances 0.000 claims description 3
- 229940083712 aldosterone antagonist Drugs 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 229940044551 receptor antagonist Drugs 0.000 claims description 3
- 239000002464 receptor antagonist Substances 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
- 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
- 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
- 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
- 229940099433 NMDA receptor antagonist Drugs 0.000 claims description 2
- 229940121954 Opioid receptor agonist Drugs 0.000 claims description 2
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims description 2
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims description 2
- 229940127473 Prostaglandin Receptor Agonists Drugs 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
- YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 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
- 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
- 239000005557 antagonist Substances 0.000 claims description 2
- 230000001142 anti-diarrhea Effects 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
- 125000005002 aryl methyl group Chemical group 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 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
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000003152 bradykinin antagonist Substances 0.000 claims description 2
- 239000000480 calcium channel blocker Substances 0.000 claims description 2
- 229940125782 compound 2 Drugs 0.000 claims description 2
- 230000000593 degrading effect Effects 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
- 229960005156 digoxin Drugs 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
- 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 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
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000000262 estrogen Substances 0.000 claims description 2
- 229940011871 estrogen Drugs 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- IDWRRERRVGBYMR-UHFFFAOYSA-N furan;pyrazine Chemical group C=1C=COC=1.C1=CN=CC=N1 IDWRRERRVGBYMR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 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
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims description 2
- SEKGKTDOBOZQAV-UHFFFAOYSA-N naphthalene;pyridine Chemical group C1=CC=NC=C1.C1=CC=CC2=CC=CC=C21 SEKGKTDOBOZQAV-UHFFFAOYSA-N 0.000 claims description 2
- 239000002840 nitric oxide donor Substances 0.000 claims description 2
- 239000003402 opiate agonist Substances 0.000 claims description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000003180 prostaglandins Chemical class 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 2
- 238000003786 synthesis reaction Methods 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
- 229930192474 thiophene Chemical group 0.000 claims description 2
- 239000003029 tricyclic antidepressant agent Substances 0.000 claims description 2
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical group CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 229960005486 vaccine Drugs 0.000 claims description 2
- 239000002536 vasopressin receptor antagonist Substances 0.000 claims description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims 1
- NQBWPTQVUAPLEM-BXKDBHETSA-N 3-[[(1r,2r)-1-carboxy-1-hydroxy-3-[2-(trifluoromethyl)phenyl]propan-2-yl]carbamoyl]-1h-pyrazole-5-carboxylic acid Chemical compound C([C@H]([C@@H](O)C(O)=O)NC(=O)C1=NNC(=C1)C(O)=O)C1=CC=CC=C1C(F)(F)F NQBWPTQVUAPLEM-BXKDBHETSA-N 0.000 claims 1
- SJKPYEYSTBGYBF-VQIMIIECSA-N 5-[[(1r,2r)-1-carboxy-1-hydroxy-3-phenylpropan-2-yl]carbamoyl]-2-[(3-fluorophenyl)methyl]pyrazole-3-carboxylic acid Chemical compound C([C@H]([C@@H](O)C(O)=O)NC(=O)C1=NN(CC=2C=C(F)C=CC=2)C(C(O)=O)=C1)C1=CC=CC=C1 SJKPYEYSTBGYBF-VQIMIIECSA-N 0.000 claims 1
- CBJMVLVAPQKKKW-VQIMIIECSA-N 5-[[(1r,2r)-1-carboxy-1-hydroxy-3-phenylpropan-2-yl]carbamoyl]-2-[(4-chloro-2,6-difluorophenyl)methyl]pyrazole-3-carboxylic acid Chemical compound C([C@H]([C@@H](O)C(O)=O)NC(=O)C1=NN(CC=2C(=CC(Cl)=CC=2F)F)C(C(O)=O)=C1)C1=CC=CC=C1 CBJMVLVAPQKKKW-VQIMIIECSA-N 0.000 claims 1
- BYXIRXAXIPXMRN-YLJYHZDGSA-N 5-[[(1r,2r)-1-carboxy-3-(2-chlorophenyl)-1-hydroxypropan-2-yl]carbamoyl]-2-[(3-methoxyphenyl)methyl]pyrazole-3-carboxylic acid Chemical compound COC1=CC=CC(CN2C(=CC(=N2)C(=O)N[C@H](CC=2C(=CC=CC=2)Cl)[C@@H](O)C(O)=O)C(O)=O)=C1 BYXIRXAXIPXMRN-YLJYHZDGSA-N 0.000 claims 1
- 239000005973 Carvone Substances 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 0 Cc1c(*)c(*)c(*)c(*)c1* Chemical compound Cc1c(*)c(*)c(*)c(*)c1* 0.000 description 36
- 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
- 229960004773 losartan Drugs 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
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960004349 candesartan cilexetil Drugs 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
- XPCFTKFZXHTYIP-PMACEKPBSA-N Benazepril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 XPCFTKFZXHTYIP-PMACEKPBSA-N 0.000 description 2
- 239000002080 C09CA02 - Eprosartan Substances 0.000 description 2
- 239000004072 C09CA03 - Valsartan Substances 0.000 description 2
- 239000002947 C09CA04 - Irbesartan Substances 0.000 description 2
- 239000005537 C09CA07 - Telmisartan Substances 0.000 description 2
- 239000003861 C09CA09 - Azilsartan medoxomil Substances 0.000 description 2
- 108010061435 Enalapril Proteins 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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
- 108010007859 Lisinopril Proteins 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- FNYLWPVRPXGIIP-UHFFFAOYSA-N Triamterene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 description 2
- 229960000571 acetazolamide Drugs 0.000 description 2
- BZKPWHYZMXOIDC-UHFFFAOYSA-N acetazolamide Chemical compound CC(=O)NC1=NN=C(S(N)(=O)=O)S1 BZKPWHYZMXOIDC-UHFFFAOYSA-N 0.000 description 2
- XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 2
- 229960002576 amiloride Drugs 0.000 description 2
- 229960001671 azapropazone Drugs 0.000 description 2
- WOIIIUDZSOLAIW-NSHDSACASA-N azapropazone Chemical compound C1=C(C)C=C2N3C(=O)[C@H](CC=C)C(=O)N3C(N(C)C)=NC2=C1 WOIIIUDZSOLAIW-NSHDSACASA-N 0.000 description 2
- 229960001211 azilsartan medoxomil Drugs 0.000 description 2
- QJFSABGVXDWMIW-UHFFFAOYSA-N azilsartan medoxomil Chemical compound C=12N(CC=3C=CC(=CC=3)C=3C(=CC=CC=3)C=3NC(=O)ON=3)C(OCC)=NC2=CC=CC=1C(=O)OCC=1OC(=O)OC=1C QJFSABGVXDWMIW-UHFFFAOYSA-N 0.000 description 2
- 229960004530 benazepril Drugs 0.000 description 2
- 229960004064 bumetanide Drugs 0.000 description 2
- MAEIEVLCKWDQJH-UHFFFAOYSA-N bumetanide Chemical compound CCCCNC1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 MAEIEVLCKWDQJH-UHFFFAOYSA-N 0.000 description 2
- 229960000830 captopril Drugs 0.000 description 2
- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 2
- 229960002155 chlorothiazide Drugs 0.000 description 2
- 229960001523 chlortalidone Drugs 0.000 description 2
- 229960005081 diclofenamide Drugs 0.000 description 2
- GJQPMPFPNINLKP-UHFFFAOYSA-N diclofenamide Chemical compound NS(=O)(=O)C1=CC(Cl)=C(Cl)C(S(N)(=O)=O)=C1 GJQPMPFPNINLKP-UHFFFAOYSA-N 0.000 description 2
- 229940030606 diuretics Drugs 0.000 description 2
- 229960000873 enalapril Drugs 0.000 description 2
- GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 2
- 229960004563 eprosartan Drugs 0.000 description 2
- OROAFUQRIXKEMV-LDADJPATSA-N eprosartan Chemical compound C=1C=C(C(O)=O)C=CC=1CN1C(CCCC)=NC=C1\C=C(C(O)=O)/CC1=CC=CS1 OROAFUQRIXKEMV-LDADJPATSA-N 0.000 description 2
- 229960005293 etodolac Drugs 0.000 description 2
- XFBVBWWRPKNWHW-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=N[C]3C(CC)=CC=CC3=C21 XFBVBWWRPKNWHW-UHFFFAOYSA-N 0.000 description 2
- 229960002390 flurbiprofen Drugs 0.000 description 2
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 2
- 229960003883 furosemide Drugs 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 229960002003 hydrochlorothiazide Drugs 0.000 description 2
- 229960003313 hydroflumethiazide Drugs 0.000 description 2
- DMDGGSIALPNSEE-UHFFFAOYSA-N hydroflumethiazide Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O DMDGGSIALPNSEE-UHFFFAOYSA-N 0.000 description 2
- 229960001680 ibuprofen Drugs 0.000 description 2
- 229960004569 indapamide Drugs 0.000 description 2
- NDDAHWYSQHTHNT-UHFFFAOYSA-N indapamide Chemical compound CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 NDDAHWYSQHTHNT-UHFFFAOYSA-N 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- 229960002198 irbesartan Drugs 0.000 description 2
- YCPOHTHPUREGFM-UHFFFAOYSA-N irbesartan Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2[N]N=NN=2)C(CCCC)=NC21CCCC2 YCPOHTHPUREGFM-UHFFFAOYSA-N 0.000 description 2
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 2
- 229960000991 ketoprofen Drugs 0.000 description 2
- 229960004752 ketorolac Drugs 0.000 description 2
- OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 description 2
- 229960002394 lisinopril Drugs 0.000 description 2
- RLAWWYSOJDYHDC-BZSNNMDCSA-N lisinopril Chemical compound C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 RLAWWYSOJDYHDC-BZSNNMDCSA-N 0.000 description 2
- KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 description 2
- 229960001929 meloxicam Drugs 0.000 description 2
- 229960002817 metolazone Drugs 0.000 description 2
- AQCHWTWZEMGIFD-UHFFFAOYSA-N metolazone Chemical compound CC1NC2=CC(Cl)=C(S(N)(=O)=O)C=C2C(=O)N1C1=CC=CC=C1C AQCHWTWZEMGIFD-UHFFFAOYSA-N 0.000 description 2
- 229960002009 naproxen Drugs 0.000 description 2
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 2
- 229960002739 oxaprozin Drugs 0.000 description 2
- OFPXSFXSNFPTHF-UHFFFAOYSA-N oxaprozin Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 OFPXSFXSNFPTHF-UHFFFAOYSA-N 0.000 description 2
- 229960002702 piroxicam Drugs 0.000 description 2
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 2
- 229960003401 ramipril Drugs 0.000 description 2
- HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 description 2
- WVYADZUPLLSGPU-UHFFFAOYSA-N salsalate Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O WVYADZUPLLSGPU-UHFFFAOYSA-N 0.000 description 2
- 229960005187 telmisartan Drugs 0.000 description 2
- 239000003451 thiazide diuretic agent Substances 0.000 description 2
- 229960001288 triamterene Drugs 0.000 description 2
- 229960004699 valsartan Drugs 0.000 description 2
- SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 2
- VLPIATFUUWWMKC-SNVBAGLBSA-N (2r)-1-(2,6-dimethylphenoxy)propan-2-amine Chemical compound C[C@@H](N)COC1=C(C)C=CC=C1C VLPIATFUUWWMKC-SNVBAGLBSA-N 0.000 description 1
- RJMIEHBSYVWVIN-LLVKDONJSA-N (2r)-2-[4-(3-oxo-1h-isoindol-2-yl)phenyl]propanoic acid Chemical compound C1=CC([C@H](C(O)=O)C)=CC=C1N1C(=O)C2=CC=CC=C2C1 RJMIEHBSYVWVIN-LLVKDONJSA-N 0.000 description 1
- BHTRKISIDQZUQX-VXGBXAGGSA-N (2r,3r)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutanoic acid Chemical compound CC(C)(C)OC(=O)N[C@@H]([C@@H](O)C(O)=O)CC1=CC=CC=C1 BHTRKISIDQZUQX-VXGBXAGGSA-N 0.000 description 1
- NVXFXLSOGLFXKQ-JMSVASOKSA-N (2s)-1-[(2r,4r)-5-ethoxy-2,4-dimethyl-5-oxopentanoyl]-2,3-dihydroindole-2-carboxylic acid Chemical compound C1=CC=C2N(C(=O)[C@H](C)C[C@@H](C)C(=O)OCC)[C@H](C(O)=O)CC2=C1 NVXFXLSOGLFXKQ-JMSVASOKSA-N 0.000 description 1
- RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 description 1
- MDKGKXOCJGEUJW-VIFPVBQESA-N (2s)-2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-VIFPVBQESA-N 0.000 description 1
- BIDNLKIUORFRQP-XYGFDPSESA-N (2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C(O)=O)CCCC1=CC=CC=C1 BIDNLKIUORFRQP-XYGFDPSESA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IFYLTXNCFVRALQ-UHFFFAOYSA-N 1-[6-amino-2-[hydroxy(4-phenylbutyl)phosphoryl]oxyhexanoyl]pyrrolidine-2-carboxylic acid Chemical compound C1CCC(C(O)=O)N1C(=O)C(CCCCN)OP(O)(=O)CCCCC1=CC=CC=C1 IFYLTXNCFVRALQ-UHFFFAOYSA-N 0.000 description 1
- PRKWVSHZYDOZLP-UHFFFAOYSA-N 2-[(6,7-dichloro-2-methyl-1-oxo-2-phenyl-3h-inden-5-yl)oxy]acetic acid Chemical compound C1C2=CC(OCC(O)=O)=C(Cl)C(Cl)=C2C(=O)C1(C)C1=CC=CC=C1 PRKWVSHZYDOZLP-UHFFFAOYSA-N 0.000 description 1
- APBSKHYXXKHJFK-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-1,3-thiazol-4-yl]acetic acid Chemical compound OC(=O)CC1=CSC(C=2C=CC(Cl)=CC=2)=N1 APBSKHYXXKHJFK-UHFFFAOYSA-N 0.000 description 1
- TYCOFFBAZNSQOJ-UHFFFAOYSA-N 2-[4-(3-fluorophenyl)phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC(F)=C1 TYCOFFBAZNSQOJ-UHFFFAOYSA-N 0.000 description 1
- XKSAJZSJKURQRX-UHFFFAOYSA-N 2-acetyloxy-5-(4-fluorophenyl)benzoic acid Chemical compound C1=C(C(O)=O)C(OC(=O)C)=CC=C1C1=CC=C(F)C=C1 XKSAJZSJKURQRX-UHFFFAOYSA-N 0.000 description 1
- QCLFSYYUWPUWQR-UHFFFAOYSA-N 4-(chloromethyl)-5-methyl-1,3-dioxol-2-one Chemical compound CC=1OC(=O)OC=1CCl QCLFSYYUWPUWQR-UHFFFAOYSA-N 0.000 description 1
- LTSOENFXCPOCHG-GQCTYLIASA-N 4-chloro-6-[[(e)-3-oxobut-1-enyl]amino]-1-n-prop-2-enylbenzene-1,3-disulfonamide Chemical compound CC(=O)\C=C\NC1=CC(Cl)=C(S(N)(=O)=O)C=C1S(=O)(=O)NCC=C LTSOENFXCPOCHG-GQCTYLIASA-N 0.000 description 1
- LBXHRAWDUMTPSE-AOOOYVTPSA-N 4-chloro-N-[(2S,6R)-2,6-dimethyl-1-piperidinyl]-3-sulfamoylbenzamide Chemical compound C[C@H]1CCC[C@@H](C)N1NC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 LBXHRAWDUMTPSE-AOOOYVTPSA-N 0.000 description 1
- SYCHUQUJURZQMO-UHFFFAOYSA-N 4-hydroxy-2-methyl-1,1-dioxo-n-(1,3-thiazol-2-yl)-1$l^{6},2-benzothiazine-3-carboxamide Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=CS1 SYCHUQUJURZQMO-UHFFFAOYSA-N 0.000 description 1
- PJJGZPJJTHBVMX-UHFFFAOYSA-N 5,7-Dihydroxyisoflavone Chemical compound C=1C(O)=CC(O)=C(C2=O)C=1OC=C2C1=CC=CC=C1 PJJGZPJJTHBVMX-UHFFFAOYSA-N 0.000 description 1
- YROKAAIPBSCMJN-UHFFFAOYSA-N 5-hydroxy-2,4-dimethyl-8-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(C)=NC(C)=C2C(O)=CC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 YROKAAIPBSCMJN-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
- USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 description 1
- VGLGVJVUHYTIIU-UHFFFAOYSA-N 6-chloro-1,1-dioxo-3-[(prop-2-enylthio)methyl]-3,4-dihydro-2H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC(CSCC=C)NS2(=O)=O VGLGVJVUHYTIIU-UHFFFAOYSA-N 0.000 description 1
- BKYKPTRYDKTTJY-UHFFFAOYSA-N 6-chloro-3-(cyclopentylmethyl)-1,1-dioxo-3,4-dihydro-2H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1NC2CC1CCCC1 BKYKPTRYDKTTJY-UHFFFAOYSA-N 0.000 description 1
- ANOGOQXCGBMIJV-UHFFFAOYSA-N 7-chloro-n-(3,4-dichlorophenyl)-5-hydroxy-1,1-dioxo-2,3-dihydro-1$l^{6}-benzothiepine-4-carboxamide Chemical compound C1CS(=O)(=O)C2=CC=C(Cl)C=C2C(O)=C1C(=O)NC1=CC=C(Cl)C(Cl)=C1 ANOGOQXCGBMIJV-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- FHHHOYXPRDYHEZ-COXVUDFISA-N Alacepril Chemical compound CC(=O)SC[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 FHHHOYXPRDYHEZ-COXVUDFISA-N 0.000 description 1
- JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 description 1
- 239000005485 Azilsartan Substances 0.000 description 1
- BWSSMIJUDVUASQ-UHFFFAOYSA-N Benzylhydrochlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1NC2CC1=CC=CC=C1 BWSSMIJUDVUASQ-UHFFFAOYSA-N 0.000 description 1
- 239000002081 C09CA05 - Tasosartan Substances 0.000 description 1
- 239000002053 C09CA06 - Candesartan Substances 0.000 description 1
- LMFUFDQNDUGNCE-UHFFFAOYSA-N CNc1cc(CCC2)c2cc1 Chemical compound CNc1cc(CCC2)c2cc1 LMFUFDQNDUGNCE-UHFFFAOYSA-N 0.000 description 1
- 108091006146 Channels Proteins 0.000 description 1
- OIRAEJWYWSAQNG-UHFFFAOYSA-N Clidanac Chemical compound ClC=1C=C2C(C(=O)O)CCC2=CC=1C1CCCCC1 OIRAEJWYWSAQNG-UHFFFAOYSA-N 0.000 description 1
- NENBAISIHCWPKP-UHFFFAOYSA-N Clofenamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 NENBAISIHCWPKP-UHFFFAOYSA-N 0.000 description 1
- VPMWFZKOWULPGT-UHFFFAOYSA-N Clorexolone Chemical compound C1C=2C=C(Cl)C(S(=O)(=O)N)=CC=2C(=O)N1C1CCCCC1 VPMWFZKOWULPGT-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 108010066671 Enalaprilat Proteins 0.000 description 1
- VXLCNTLWWUDBSO-UHFFFAOYSA-N Ethiazide Chemical compound ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)NC(CC)NC2=C1 VXLCNTLWWUDBSO-UHFFFAOYSA-N 0.000 description 1
- RBBWCVQDXDFISW-UHFFFAOYSA-N Feprazone Chemical compound O=C1C(CC=C(C)C)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 RBBWCVQDXDFISW-UHFFFAOYSA-N 0.000 description 1
- XWLUWCNOOVRFPX-UHFFFAOYSA-N Fosphenytoin Chemical compound O=C1N(COP(O)(=O)O)C(=O)NC1(C=1C=CC=CC=1)C1=CC=CC=C1 XWLUWCNOOVRFPX-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- LINHZVMHXABQLB-ZDUSSCGKSA-N Isoboldine Chemical compound CN1CCC2=CC(OC)=C(O)C3=C2[C@@H]1CC1=C3C=C(OC)C(O)=C1 LINHZVMHXABQLB-ZDUSSCGKSA-N 0.000 description 1
- UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 description 1
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 1
- ALFGKMXHOUSVAD-UHFFFAOYSA-N Ketobemidone Chemical compound C=1C=CC(O)=CC=1C1(C(=O)CC)CCN(C)CC1 ALFGKMXHOUSVAD-UHFFFAOYSA-N 0.000 description 1
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- CESYKOGBSMNBPD-UHFFFAOYSA-N Methyclothiazide Chemical compound ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)N(C)C(CCl)NC2=C1 CESYKOGBSMNBPD-UHFFFAOYSA-N 0.000 description 1
- UWWDHYUMIORJTA-HSQYWUDLSA-N Moexipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC(OC)=C(OC)C=C2C1)C(O)=O)CC1=CC=CC=C1 UWWDHYUMIORJTA-HSQYWUDLSA-N 0.000 description 1
- BLXXJMDCKKHMKV-UHFFFAOYSA-N Nabumetone Chemical compound C1=C(CCC(C)=O)C=CC2=CC(OC)=CC=C21 BLXXJMDCKKHMKV-UHFFFAOYSA-N 0.000 description 1
- 102000003729 Neprilysin Human genes 0.000 description 1
- 108090000028 Neprilysin Proteins 0.000 description 1
- JZFPYUNJRRFVQU-UHFFFAOYSA-N Niflumic acid Chemical compound OC(=O)C1=CC=CN=C1NC1=CC=CC(C(F)(F)F)=C1 JZFPYUNJRRFVQU-UHFFFAOYSA-N 0.000 description 1
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
- UJEWTUDSLQGTOA-UHFFFAOYSA-N Piretanide Chemical compound C=1C=CC=CC=1OC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1N1CCCC1 UJEWTUDSLQGTOA-UHFFFAOYSA-N 0.000 description 1
- CYLWJCABXYDINA-UHFFFAOYSA-N Polythiazide Polymers ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)N(C)C(CSCC(F)(F)F)NC2=C1 CYLWJCABXYDINA-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- TVQZAMVBTVNYLA-UHFFFAOYSA-N Pranoprofen Chemical compound C1=CC=C2CC3=CC(C(C(O)=O)C)=CC=C3OC2=N1 TVQZAMVBTVNYLA-UHFFFAOYSA-N 0.000 description 1
- 239000005477 Pratosartan Substances 0.000 description 1
- 239000005478 Saprisartan Substances 0.000 description 1
- DUEWVPTZCSAMNB-UHFFFAOYSA-N Saprisartan Chemical compound NC(=O)C=1N(CC=2C=C3C(Br)=C(OC3=CC=2)C=2C(=CC=CC=2)NS(=O)(=O)C(F)(F)F)C(CC)=NC=1C1CC1 DUEWVPTZCSAMNB-UHFFFAOYSA-N 0.000 description 1
- NGBFQHCMQULJNZ-UHFFFAOYSA-N Torsemide Chemical compound CC(C)NC(=O)NS(=O)(=O)C1=CN=CC=C1NC1=CC=CC(C)=C1 NGBFQHCMQULJNZ-UHFFFAOYSA-N 0.000 description 1
- VXFJYXUZANRPDJ-WTNASJBWSA-N Trandopril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@H]2CCCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 VXFJYXUZANRPDJ-WTNASJBWSA-N 0.000 description 1
- 229950010933 abitesartan Drugs 0.000 description 1
- ZUMPSVPHCDJCMD-UHFFFAOYSA-N abitesartan Chemical compound C1CCCC1(C(O)=O)CN(C(=O)CCCC)CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ZUMPSVPHCDJCMD-UHFFFAOYSA-N 0.000 description 1
- 229960004892 acemetacin Drugs 0.000 description 1
- FSQKKOOTNAMONP-UHFFFAOYSA-N acemetacin Chemical compound CC1=C(CC(=O)OCC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 FSQKKOOTNAMONP-UHFFFAOYSA-N 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229950007884 alacepril Drugs 0.000 description 1
- 229960005142 alclofenac Drugs 0.000 description 1
- ARHWPKZXBHOEEE-UHFFFAOYSA-N alclofenac Chemical compound OC(=O)CC1=CC=C(OCC=C)C(Cl)=C1 ARHWPKZXBHOEEE-UHFFFAOYSA-N 0.000 description 1
- 229960004663 alminoprofen Drugs 0.000 description 1
- FPHLBGOJWPEVME-UHFFFAOYSA-N alminoprofen Chemical compound OC(=O)C(C)C1=CC=C(NCC(C)=C)C=C1 FPHLBGOJWPEVME-UHFFFAOYSA-N 0.000 description 1
- 229950007522 altizide Drugs 0.000 description 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
- 229960003805 amantadine Drugs 0.000 description 1
- 229950007019 ambuside Drugs 0.000 description 1
- 229950008930 amfenac Drugs 0.000 description 1
- SOYCMDCMZDHQFP-UHFFFAOYSA-N amfenac Chemical compound NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=CC=C1 SOYCMDCMZDHQFP-UHFFFAOYSA-N 0.000 description 1
- 229940006133 antiglaucoma drug and miotics carbonic anhydrase inhibitors Drugs 0.000 description 1
- 229960002731 azilsartan Drugs 0.000 description 1
- KGSXMPPBFPAXLY-UHFFFAOYSA-N azilsartan Chemical compound CCOC1=NC2=CC=CC(C(O)=O)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NOC(=O)N1 KGSXMPPBFPAXLY-UHFFFAOYSA-N 0.000 description 1
- 229960004067 benazeprilat Drugs 0.000 description 1
- MADRIHWFJGRSBP-ROUUACIJSA-N benazeprilat Chemical compound C([C@H](N[C@H]1CCC2=CC=CC=C2N(C1=O)CC(=O)O)C(O)=O)CC1=CC=CC=C1 MADRIHWFJGRSBP-ROUUACIJSA-N 0.000 description 1
- 229960003515 bendroflumethiazide Drugs 0.000 description 1
- HDWIHXWEUNVBIY-UHFFFAOYSA-N bendroflumethiazidum Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1NC2CC1=CC=CC=C1 HDWIHXWEUNVBIY-UHFFFAOYSA-N 0.000 description 1
- 229960004277 benorilate Drugs 0.000 description 1
- FEJKLNWAOXSSNR-UHFFFAOYSA-N benorilate Chemical compound C1=CC(NC(=O)C)=CC=C1OC(=O)C1=CC=CC=C1OC(C)=O FEJKLNWAOXSSNR-UHFFFAOYSA-N 0.000 description 1
- 229960005430 benoxaprofen Drugs 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 229950007003 benzylhydrochlorothiazide Drugs 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- HZIYHIRJHYIRQO-UHFFFAOYSA-N butazolamide Chemical compound CCCC(=O)NC1=NN=C(S(N)(=O)=O)S1 HZIYHIRJHYIRQO-UHFFFAOYSA-N 0.000 description 1
- 229950000426 butazolamide Drugs 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229960000932 candesartan Drugs 0.000 description 1
- 229960000623 carbamazepine Drugs 0.000 description 1
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 1
- 239000003489 carbonate dehydratase inhibitor Substances 0.000 description 1
- 229960003184 carprofen Drugs 0.000 description 1
- IVUMCTKHWDRRMH-UHFFFAOYSA-N carprofen Chemical compound C1=CC(Cl)=C[C]2C3=CC=C(C(C(O)=O)C)C=C3N=C21 IVUMCTKHWDRRMH-UHFFFAOYSA-N 0.000 description 1
- IHJCXVZDYSXXFT-UHFFFAOYSA-N chloraminophenamide Chemical compound NC1=CC(Cl)=C(S(N)(=O)=O)C=C1S(N)(=O)=O IHJCXVZDYSXXFT-UHFFFAOYSA-N 0.000 description 1
- 229960005025 cilazapril Drugs 0.000 description 1
- HHHKFGXWKKUNCY-FHWLQOOXSA-N cilazapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N2[C@@H](CCCN2CCC1)C(O)=O)=O)CC1=CC=CC=C1 HHHKFGXWKKUNCY-FHWLQOOXSA-N 0.000 description 1
- 229950010886 clidanac Drugs 0.000 description 1
- 229960002883 clofenamide Drugs 0.000 description 1
- 229960004070 clopamide Drugs 0.000 description 1
- 229960005315 clorexolone Drugs 0.000 description 1
- 229960003206 cyclopenthiazide Drugs 0.000 description 1
- 229960003176 cyclothiazide Drugs 0.000 description 1
- BOCUKUHCLICSIY-QJWLJZLASA-N cyclothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1NC2C1[C@H](C=C2)C[C@H]2C1 BOCUKUHCLICSIY-QJWLJZLASA-N 0.000 description 1
- 229960005227 delapril Drugs 0.000 description 1
- WOUOLAUOZXOLJQ-MBSDFSHPSA-N delapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N(CC(O)=O)C1CC2=CC=CC=C2C1)CC1=CC=CC=C1 WOUOLAUOZXOLJQ-MBSDFSHPSA-N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 1
- 229960004193 dextropropoxyphene Drugs 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 229960001259 diclofenac Drugs 0.000 description 1
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
- 229960000616 diflunisal Drugs 0.000 description 1
- HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 description 1
- 229950008177 disulfamide Drugs 0.000 description 1
- RCFKEIREOSXLET-UHFFFAOYSA-N disulfamide Chemical compound CC1=CC(Cl)=C(S(N)(=O)=O)C=C1S(N)(=O)=O RCFKEIREOSXLET-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229950006127 embusartan Drugs 0.000 description 1
- 229960002680 enalaprilat Drugs 0.000 description 1
- LZFZMUMEGBBDTC-QEJZJMRPSA-N enalaprilat (anhydrous) Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 LZFZMUMEGBBDTC-QEJZJMRPSA-N 0.000 description 1
- 229950002107 enolicam Drugs 0.000 description 1
- 229950010350 epitizide Drugs 0.000 description 1
- RINBGYCKMGDWPY-UHFFFAOYSA-N epitizide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC(CSCC(F)(F)F)NS2(=O)=O RINBGYCKMGDWPY-UHFFFAOYSA-N 0.000 description 1
- 229960000573 eprosartan mesylate Drugs 0.000 description 1
- DJSLTDBPKHORNY-XMMWENQYSA-N eprosartan methanesulfonate Chemical compound CS(O)(=O)=O.C=1C=C(C(O)=O)C=CC=1CN1C(CCCC)=NC=C1\C=C(C(O)=O)/CC1=CC=CS1 DJSLTDBPKHORNY-XMMWENQYSA-N 0.000 description 1
- AVOLMBLBETYQHX-UHFFFAOYSA-N etacrynic acid Chemical compound CCC(=C)C(=O)C1=CC=C(OCC(O)=O)C(Cl)=C1Cl AVOLMBLBETYQHX-UHFFFAOYSA-N 0.000 description 1
- 229960003199 etacrynic acid Drugs 0.000 description 1
- 229950007164 ethiazide Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- ULANGSAJTINEBA-UHFFFAOYSA-N ethyl n-(3-benzoylphenyl)-n-(trifluoromethylsulfonyl)carbamate Chemical compound CCOC(=O)N(S(=O)(=O)C(F)(F)F)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 ULANGSAJTINEBA-UHFFFAOYSA-N 0.000 description 1
- 229960001395 fenbufen Drugs 0.000 description 1
- ZPAKPRAICRBAOD-UHFFFAOYSA-N fenbufen Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1 ZPAKPRAICRBAOD-UHFFFAOYSA-N 0.000 description 1
- 229950006236 fenclofenac Drugs 0.000 description 1
- IDKAXRLETRCXKS-UHFFFAOYSA-N fenclofenac Chemical compound OC(=O)CC1=CC=CC=C1OC1=CC=C(Cl)C=C1Cl IDKAXRLETRCXKS-UHFFFAOYSA-N 0.000 description 1
- 229950011481 fenclozic acid Drugs 0.000 description 1
- 229960001419 fenoprofen Drugs 0.000 description 1
- 229960000489 feprazone Drugs 0.000 description 1
- 229960004369 flufenamic acid Drugs 0.000 description 1
- LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 description 1
- 229950007979 flufenisal Drugs 0.000 description 1
- 229960003028 flumethiazide Drugs 0.000 description 1
- RGUQWGXAYZNLMI-UHFFFAOYSA-N flumethiazide Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O RGUQWGXAYZNLMI-UHFFFAOYSA-N 0.000 description 1
- 229950001284 fluprofen Drugs 0.000 description 1
- 229960002490 fosinopril Drugs 0.000 description 1
- 229960000693 fosphenytoin Drugs 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229950009183 ibufenac Drugs 0.000 description 1
- CYWFCPPBTWOZSF-UHFFFAOYSA-N ibufenac Chemical compound CC(C)CC1=CC=C(CC(O)=O)C=C1 CYWFCPPBTWOZSF-UHFFFAOYSA-N 0.000 description 1
- 229960001195 imidapril Drugs 0.000 description 1
- KLZWOWYOHUKJIG-BPUTZDHNSA-N imidapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1C(N(C)C[C@H]1C(O)=O)=O)CC1=CC=CC=C1 KLZWOWYOHUKJIG-BPUTZDHNSA-N 0.000 description 1
- 229950009607 indacrinone Drugs 0.000 description 1
- 229960004187 indoprofen Drugs 0.000 description 1
- 229950011455 isoxepac Drugs 0.000 description 1
- QFGMXJOBTNZHEL-UHFFFAOYSA-N isoxepac Chemical compound O1CC2=CC=CC=C2C(=O)C2=CC(CC(=O)O)=CC=C21 QFGMXJOBTNZHEL-UHFFFAOYSA-N 0.000 description 1
- 229960003299 ketamine Drugs 0.000 description 1
- 229960003029 ketobemidone Drugs 0.000 description 1
- 229960004194 lidocaine Drugs 0.000 description 1
- 239000002171 loop diuretic Substances 0.000 description 1
- OXROWJKCGCOJDO-JLHYYAGUSA-N lornoxicam Chemical compound O=C1C=2SC(Cl)=CC=2S(=O)(=O)N(C)\C1=C(\O)NC1=CC=CC=N1 OXROWJKCGCOJDO-JLHYYAGUSA-N 0.000 description 1
- 229960002202 lornoxicam Drugs 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 229940013798 meclofenamate Drugs 0.000 description 1
- 229960003803 meclofenamic acid Drugs 0.000 description 1
- 229960003464 mefenamic acid Drugs 0.000 description 1
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 description 1
- 229960004640 memantine Drugs 0.000 description 1
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 1
- 229960004963 mesalazine Drugs 0.000 description 1
- 229960001797 methadone Drugs 0.000 description 1
- FLOSMHQXBMRNHR-DAXSKMNVSA-N methazolamide Chemical compound CC(=O)\N=C1/SC(S(N)(=O)=O)=NN1C FLOSMHQXBMRNHR-DAXSKMNVSA-N 0.000 description 1
- 229960004083 methazolamide Drugs 0.000 description 1
- 229960003739 methyclothiazide Drugs 0.000 description 1
- LYVGOAYMIAQLHI-UHFFFAOYSA-N methyl 2-butyl-1-[[2-fluoro-4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]-6-oxopyridine-4-carboxylate Chemical compound CCCCC1=CC(C(=O)OC)=CC(=O)N1CC1=CC=C(C=2C(=CC=CC=2)C2=NNN=N2)C=C1F LYVGOAYMIAQLHI-UHFFFAOYSA-N 0.000 description 1
- 229960003404 mexiletine Drugs 0.000 description 1
- 229960005170 moexipril Drugs 0.000 description 1
- 229960005285 mofebutazone Drugs 0.000 description 1
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical compound O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 1
- 229960004270 nabumetone Drugs 0.000 description 1
- 229960000916 niflumic acid Drugs 0.000 description 1
- 239000002337 osmotic diuretic agent Substances 0.000 description 1
- CTRLABGOLIVAIY-UHFFFAOYSA-N oxcarbazepine Chemical compound C1C(=O)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 CTRLABGOLIVAIY-UHFFFAOYSA-N 0.000 description 1
- 229960001816 oxcarbazepine Drugs 0.000 description 1
- 229960000649 oxyphenbutazone Drugs 0.000 description 1
- HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 description 1
- 229950008492 pentopril Drugs 0.000 description 1
- 229960002582 perindopril Drugs 0.000 description 1
- IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 229960002036 phenytoin Drugs 0.000 description 1
- 229960001085 piretanide Drugs 0.000 description 1
- 229960000851 pirprofen Drugs 0.000 description 1
- PIDSZXPFGCURGN-UHFFFAOYSA-N pirprofen Chemical compound ClC1=CC(C(C(O)=O)C)=CC=C1N1CC=CC1 PIDSZXPFGCURGN-UHFFFAOYSA-N 0.000 description 1
- 229960005483 polythiazide Drugs 0.000 description 1
- 229920000046 polythiazide Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical class [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 1
- 229960003101 pranoprofen Drugs 0.000 description 1
- KCTFTBCZZUBAKN-UHFFFAOYSA-N pratosartan Chemical compound CCCC1=NC=2CCCCC(=O)C=2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 KCTFTBCZZUBAKN-UHFFFAOYSA-N 0.000 description 1
- 229950005649 pratosartan Drugs 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229960001455 quinapril Drugs 0.000 description 1
- JSDRRTOADPPCHY-HSQYWUDLSA-N quinapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 JSDRRTOADPPCHY-HSQYWUDLSA-N 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 229960000953 salsalate Drugs 0.000 description 1
- 229950006241 saprisartan Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940125794 sodium channel blocker Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960002909 spirapril Drugs 0.000 description 1
- HRWCVUIFMSZDJS-SZMVWBNQSA-N spirapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2(C1)SCCS2)C(O)=O)CC1=CC=CC=C1 HRWCVUIFMSZDJS-SZMVWBNQSA-N 0.000 description 1
- 108700035424 spirapril Proteins 0.000 description 1
- 229960002256 spironolactone Drugs 0.000 description 1
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
- 229950005175 sudoxicam Drugs 0.000 description 1
- 229960001940 sulfasalazine Drugs 0.000 description 1
- NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 description 1
- NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 229960000894 sulindac Drugs 0.000 description 1
- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 1
- 229960004492 suprofen Drugs 0.000 description 1
- 229960000651 tasosartan Drugs 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- 229960004084 temocapril Drugs 0.000 description 1
- FIQOFIRCTOWDOW-BJLQDIEVSA-N temocapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N(CC(O)=O)C[C@H](SC1)C=1SC=CC=1)=O)CC1=CC=CC=C1 FIQOFIRCTOWDOW-BJLQDIEVSA-N 0.000 description 1
- 229960002871 tenoxicam Drugs 0.000 description 1
- WZWYJBNHTWCXIM-UHFFFAOYSA-N tenoxicam Chemical compound O=C1C=2SC=CC=2S(=O)(=O)N(C)C1=C(O)NC1=CC=CC=N1 WZWYJBNHTWCXIM-UHFFFAOYSA-N 0.000 description 1
- 239000005458 thiazide-like diuretic Substances 0.000 description 1
- AGHANLSBXUWXTB-UHFFFAOYSA-N tienilic acid Chemical compound ClC1=C(Cl)C(OCC(=O)O)=CC=C1C(=O)C1=CC=CS1 AGHANLSBXUWXTB-UHFFFAOYSA-N 0.000 description 1
- 229960000356 tienilic acid Drugs 0.000 description 1
- 229960002905 tolfenamic acid Drugs 0.000 description 1
- YEZNLOUZAIOMLT-UHFFFAOYSA-N tolfenamic acid Chemical compound CC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(O)=O YEZNLOUZAIOMLT-UHFFFAOYSA-N 0.000 description 1
- 229960005461 torasemide Drugs 0.000 description 1
- 229960002051 trandolapril Drugs 0.000 description 1
- 229950000451 triflumidate Drugs 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229960000537 xipamide Drugs 0.000 description 1
- MTZBBNMLMNBNJL-UHFFFAOYSA-N xipamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C1=CC(S(N)(=O)=O)=C(Cl)C=C1O MTZBBNMLMNBNJL-UHFFFAOYSA-N 0.000 description 1
- 229960002769 zofenopril Drugs 0.000 description 1
- IAIDUHCBNLFXEF-MNEFBYGVSA-N zofenopril Chemical compound C([C@@H](C)C(=O)N1[C@@H](C[C@@H](C1)SC=1C=CC=CC=1)C(O)=O)SC(=O)C1=CC=CC=C1 IAIDUHCBNLFXEF-MNEFBYGVSA-N 0.000 description 1
- 229950004433 zolasartan Drugs 0.000 description 1
- FIKYECRHLXONOX-UHFFFAOYSA-N zolasartan Chemical compound CCCCC1=NC(Cl)=C(C(O)=O)N1CC1=CC=C(OC(=C2Br)C=3C(=CC=CC=3)C3=NNN=N3)C2=C1 FIKYECRHLXONOX-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161491750P | 2011-05-31 | 2011-05-31 | |
| US61/491,750 | 2011-05-31 | ||
| PCT/US2012/038511 WO2012166387A1 (en) | 2011-05-31 | 2012-05-18 | Neprilysin inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016000344A Division JP2016047857A (ja) | 2011-05-31 | 2016-01-05 | ネプリライシン阻害剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014515401A JP2014515401A (ja) | 2014-06-30 |
| JP2014515401A5 true JP2014515401A5 (OSRAM) | 2015-04-16 |
| JP5959074B2 JP5959074B2 (ja) | 2016-08-02 |
Family
ID=46201815
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014513547A Expired - Fee Related JP5959074B2 (ja) | 2011-05-31 | 2012-05-18 | ネプリライシン阻害剤 |
| JP2016000344A Withdrawn JP2016047857A (ja) | 2011-05-31 | 2016-01-05 | ネプリライシン阻害剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016000344A Withdrawn JP2016047857A (ja) | 2011-05-31 | 2016-01-05 | ネプリライシン阻害剤 |
Country Status (7)
| Country | Link |
|---|---|
| US (5) | US8513244B2 (OSRAM) |
| EP (1) | EP2714662B1 (OSRAM) |
| JP (2) | JP5959074B2 (OSRAM) |
| CN (1) | CN103596928B (OSRAM) |
| CA (1) | CA2835216A1 (OSRAM) |
| ES (1) | ES2653215T3 (OSRAM) |
| WO (1) | WO2012166387A1 (OSRAM) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9468637B2 (en) | 2009-05-13 | 2016-10-18 | Intra-Cellular Therapies, Inc. | Organic compounds |
| RS54348B1 (sr) | 2010-12-15 | 2016-02-29 | Theravance Biopharma R&D Ip, Llc | Inhibitori neprilizina |
| KR101892611B1 (ko) | 2010-12-15 | 2018-08-28 | 세라밴스 바이오파마 알앤디 아이피, 엘엘씨 | 네프릴리신 억제제 |
| CN103380119B (zh) | 2011-02-17 | 2016-02-17 | 施万生物制药研发Ip有限责任公司 | 作为脑啡肽酶抑制剂的经取代的氨基丁酸衍生物 |
| WO2012154249A1 (en) | 2011-02-17 | 2012-11-15 | Theravance, Inc. | Substituted aminobutyric derivatives as neprilysin inhibitors |
| EP2714660B1 (en) | 2011-05-31 | 2018-09-26 | Theravance Biopharma R&D IP, LLC | 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 |
| WO2013014204A2 (en) * | 2011-07-26 | 2013-01-31 | Sanofi | 3-heteroaroylamino-propionic acid derivatives and their use as pharmaceuticals |
| TWI560172B (en) | 2011-11-02 | 2016-12-01 | Theravance Biopharma R&D Ip Llc | Neprilysin inhibitors |
| CA2871292A1 (en) | 2012-05-31 | 2013-12-05 | Theravance Biopharma R&D Ip, Llc | Nitric oxide donor neprilysin inhibitors |
| MX356260B (es) | 2012-06-08 | 2018-05-21 | Theravance Biopharma R&D Ip Llc | Inhibidores de la neprilisina. |
| CA2873328A1 (en) | 2012-06-08 | 2013-12-12 | Theravance Biopharma R&D Ip, Llc | Neprilysin inhibitors |
| CN104520277B (zh) | 2012-08-08 | 2018-01-19 | 施万生物制药研发Ip有限责任公司 | 脑啡肽酶抑制剂 |
| US9801882B2 (en) | 2013-02-17 | 2017-10-31 | Intra-Cellular Therapies, Inc. | Phosphodiesterase-1 inhibitors and their use in treatment of cardiovascular diseases |
| HRP20171097T1 (hr) | 2013-03-05 | 2017-10-06 | Theravance Biopharma R&D Ip, Llc | Inhibitori neprilizina |
| JP2017504625A (ja) | 2014-01-30 | 2017-02-09 | 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５−ビフェニル−４−ヘテロアリールカルボニルアミノ−ペンタン酸誘導体 |
| SG11201605965UA (en) | 2014-01-30 | 2016-08-30 | Theravance Biopharma R&D Ip Llc | Neprilysin inhibitors |
| WO2015188073A1 (en) * | 2014-06-06 | 2015-12-10 | Research Triangle Institute | Apelin receptor (apj) agonists and uses thereof |
| US10285992B2 (en) | 2014-08-07 | 2019-05-14 | Intra-Cellular Therapies, Inc. | Combinations of PDE1 inhibitors and NEP inhibitors and associated methods |
| ES2745819T3 (es) | 2014-08-07 | 2020-03-03 | Intra Cellular Therapies Inc | Derivados de imidazo[1,2-a]-pirazolo[4,3-e]-pirimidin-4-ona con actividad inhibidora de la PDE1 |
| JP6783230B2 (ja) * | 2014-10-10 | 2020-11-11 | ジェネンテック， インコーポレイテッド | ヒストンデメチラーゼのインヒビターとしてのピロリドンアミド化合物 |
| 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 |
| HRP20210040T1 (hr) | 2015-02-19 | 2021-04-02 | Theravance Biopharma R&D Ip, Llc | (2r,4r)-5-(5′-klor-2’-fluorbifenil-4-il)-2-hidroksi-4-[(5-metiloksazol-2-karbonil)amino]pentanska kiselina |
| BR112018011784A2 (pt) | 2015-12-09 | 2018-12-04 | Res Triangle Inst | agonistas aprimorados do receptor de apelina (apj) e usos dos mesmos |
| CA3015505C (en) | 2016-03-08 | 2024-03-05 | 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 |
| JP2019510039A (ja) | 2016-03-28 | 2019-04-11 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 新規組成物および方法 |
| WO2019022436A2 (ko) * | 2017-07-27 | 2019-01-31 | 에리슨제약(주) | Nep 저해제 및 베타-차단제를 포함하는 약제학적 조성물 |
| EP3746081A4 (en) | 2018-01-31 | 2021-10-27 | Intra-Cellular Therapies, Inc. | Novel uses |
| EP3887363A1 (en) | 2018-11-27 | 2021-10-06 | Novartis AG | Cyclic pentamer compounds as proprotein convertase subtilisin/kexin type 9 (pcsk9) inhibitors for the treatment of metabolic disorder |
| 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 |
| 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 |
| WO2021041791A1 (en) * | 2019-08-29 | 2021-03-04 | Rti International, Inc. | Methods and uses for apelin receptor agonists |
| 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 |
| CN115894373B (zh) * | 2022-10-27 | 2025-08-01 | 常州大学 | N-取代苄基吡唑衍生物在作为β2肾上腺素受体调节剂、拮抗剂和激动剂的应用 |
| CN115745891B (zh) * | 2022-11-10 | 2025-08-01 | 常州大学 | 吡唑衍生物在作为β2-肾上腺素受体拮抗剂的应用 |
Family Cites Families (58)
| 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 |
| 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 |
| CA2218716A1 (en) | 1995-04-21 | 1996-10-24 | Novartis Ag | N-aroylamino acid amides as endothelin inhibitors |
| MX9709874A (es) | 1995-06-06 | 1998-03-31 | Pfizer | N-(INDOL-2-CARBONIL) beta-ALANILAMIDAS SUSTITUIDAS Y DERIVADOS COMO INHIBIDORES DE GLUCOGENO FOSFORILASA, USO DE LOS MISMOS Y COMPOSICIONES QUE LOS CONTIENEN. |
| US5932550A (en) | 1995-06-30 | 1999-08-03 | Japan Energy Corporation | Dipeptide compound or pharmaceutically acceptable salt thereof and medical use thereof |
| AU3213799A (en) | 1998-04-01 | 1999-10-18 | Du Pont Pharmaceuticals Company | 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 |
| NZ543482A (en) | 2003-05-21 | 2009-02-28 | Prosidion Ltd | 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 |
| SG185318A1 (en) | 2007-01-12 | 2012-11-29 | 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 |
| EP2225210B1 (en) | 2007-12-11 | 2012-04-25 | Theravance, Inc. | Dual-acting benzoimidazole derivative and their use as antihypertensive agents |
| 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 |
| US8236798B2 (en) | 2009-05-07 | 2012-08-07 | Abbott Gmbh & Co. Kg | Carboxamide compounds and their use as calpain inhibitors |
| BRPI1011657A2 (pt) * | 2009-05-28 | 2019-04-16 | Novartis Ag | derivados aminopropiônicos substituídos como inibidores de neprilisina |
| EP2435402B1 (en) | 2009-05-28 | 2016-04-13 | Novartis AG | Substituted aminobutyric derivatives as neprilysin inhibitors |
| EP2451782B1 (en) * | 2009-07-07 | 2016-11-09 | Theravance Biopharma R&D IP, LLC | Dual-acting pyrazole antihypertensive agents |
| US8372984B2 (en) | 2009-07-22 | 2013-02-12 | Theravance, Inc. | Dual-acting oxazole antihypertensive agents |
| JO2967B1 (en) | 2009-11-20 | 2016-03-15 | نوفارتس ايه جي | Acetic acid derivatives of carbamoyl methyl amino are substituted as new NEP inhibitors |
| CN104262228B (zh) | 2010-01-22 | 2017-01-18 | 诺华股份有限公司 | 中性内肽酶抑制剂中间体和其制备方法 |
| AR079967A1 (es) * | 2010-01-26 | 2012-02-29 | Sanofi Aventis | Derivados de acido 3-heteroaroilamino-propionico sustituidos con oxigeno y su uso como productos farmaceuticos |
| 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 |
| KR101892611B1 (ko) | 2010-12-15 | 2018-08-28 | 세라밴스 바이오파마 알앤디 아이피, 엘엘씨 | 네프릴리신 억제제 |
| RS54348B1 (sr) | 2010-12-15 | 2016-02-29 | Theravance Biopharma R&D Ip, Llc | Inhibitori neprilizina |
| TWI523844B (zh) * | 2011-01-26 | 2016-03-01 | 賽諾菲公司 | 經胺基取代之３－雜芳醯基胺基－丙酸衍生物及其作為藥物之用途 |
| WO2012154249A1 (en) | 2011-02-17 | 2012-11-15 | Theravance, Inc. | Substituted aminobutyric derivatives as neprilysin inhibitors |
| CN103380119B (zh) | 2011-02-17 | 2016-02-17 | 施万生物制药研发Ip有限责任公司 | 作为脑啡肽酶抑制剂的经取代的氨基丁酸衍生物 |
| 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 |
| US8686184B2 (en) | 2011-05-31 | 2014-04-01 | Theravance, Inc. | Neprilysin inhibitors |
| 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 |
| CA2871292A1 (en) | 2012-05-31 | 2013-12-05 | Theravance Biopharma R&D Ip, Llc | Nitric oxide donor neprilysin inhibitors |
| CA2873328A1 (en) | 2012-06-08 | 2013-12-12 | Theravance Biopharma R&D Ip, Llc | Neprilysin inhibitors |
| MX356260B (es) | 2012-06-08 | 2018-05-21 | Theravance Biopharma R&D Ip Llc | Inhibidores de la neprilisina. |
| CN104520277B (zh) | 2012-08-08 | 2018-01-19 | 施万生物制药研发Ip有限责任公司 | 脑啡肽酶抑制剂 |
| HRP20171097T1 (hr) | 2013-03-05 | 2017-10-06 | Theravance Biopharma R&D Ip, Llc | Inhibitori neprilizina |
-
2012
- 2012-05-18 JP JP2014513547A patent/JP5959074B2/ja not_active Expired - Fee Related
- 2012-05-18 EP EP12725202.1A patent/EP2714662B1/en active Active
- 2012-05-18 WO PCT/US2012/038511 patent/WO2012166387A1/en not_active Ceased
- 2012-05-18 ES ES12725202.1T patent/ES2653215T3/es active Active
- 2012-05-18 US US13/474,987 patent/US8513244B2/en not_active Expired - Fee Related
- 2012-05-18 CN CN201280026418.9A patent/CN103596928B/zh not_active Expired - Fee Related
- 2012-05-18 CA CA2835216A patent/CA2835216A1/en not_active Abandoned
-
2013
- 2013-07-08 US US13/936,343 patent/US8993752B2/en active Active
-
2015
- 2015-02-18 US US14/624,729 patent/US9422245B2/en not_active Expired - Fee Related
-
2016
- 2016-01-05 JP JP2016000344A patent/JP2016047857A/ja not_active Withdrawn
- 2016-07-21 US US15/215,763 patent/US9828367B2/en active Active
-
2017
- 2017-10-24 US US15/791,713 patent/US20180194757A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2014515401A5 (OSRAM) | ||
| JP2014528903A5 (OSRAM) | ||
| JP2014503534A5 (OSRAM) | ||
| JP2013545811A5 (OSRAM) | ||
| JP2014515402A5 (OSRAM) | ||
| JP5944921B2 (ja) | ネプリライシン阻害剤 | |
| JP5959074B2 (ja) | ネプリライシン阻害剤 | |
| JP5959065B2 (ja) | ネプリライシン阻害剤としての置換アミノ酪酸誘導体 | |
| JP5959075B2 (ja) | ネプリライシン阻害剤 | |
| JP5944922B2 (ja) | ネプリライシン阻害剤 | |
| JP6092390B2 (ja) | ネプリライシン阻害剤 | |
| TWI406850B (zh) | 雙效苯并咪唑抗高血壓劑 | |
| JP5959066B2 (ja) | ネプリライシン阻害剤としての置換アミノ酪酸誘導体 | |
| TWI583671B (zh) | 腦啡肽酶抑制劑 | |
| JP2018203761A (ja) | ネプリライシン阻害剤 | |
| HUE034647T2 (hu) | Oxálsavamidok mint neprilizin inhibitorok, gyógyszerkészítményeik és elõállításuk | |
| JP2016047846A (ja) | ネプリライシン阻害剤 | |
| SK13195A3 (en) | Imidazole carboxylic acids and pharmaceutical agent containing thereof | |
| JP2018199709A (ja) | ネプリライシン阻害剤としての５−ビフェニル−４−ヘテロアリールカルボニルアミノ−ペンタン酸誘導体 | |
| JP2012533626A (ja) | 二重作用オキサゾール降圧剤 | |
| JP2013517295A (ja) | 二重に作用するチオフェン、ピロール、チアゾールおよびフラン抗高血圧症薬 | |
| RU2715241C2 (ru) | (2r,4r)-5-(5′-хлор-2′-фторбифенил-4-ил)-2-гидрокси-4-[(5-метилоксазол-2-карбонил)амино]пентановая кислота | |
| TWI731943B (zh) | 結晶型（2s，4r）－5－（5’－氯－2’－氟－［1，1’－聯苯］－4－基）－2－（乙氧基甲基）－4－（3－羥基異㗁唑－5－甲醯胺基）－2－甲基戊酸及其用途 |