ES2386140T3 - Derivados de pirazol, composición medicinal que contiene los mismos, uso medicinal de los mismos e intermedio para la producción de los mismos - Google Patents
Derivados de pirazol, composición medicinal que contiene los mismos, uso medicinal de los mismos e intermedio para la producción de los mismos Download PDFInfo
- Publication number
- ES2386140T3 ES2386140T3 ES03792760T ES03792760T ES2386140T3 ES 2386140 T3 ES2386140 T3 ES 2386140T3 ES 03792760 T ES03792760 T ES 03792760T ES 03792760 T ES03792760 T ES 03792760T ES 2386140 T3 ES2386140 T3 ES 2386140T3
- Authority
- ES
- Spain
- Prior art keywords
- group
- alkyl
- inhibitor
- hydroxy
- amino
- 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.)
- Expired - Lifetime
Links
- 150000003217 pyrazoles Chemical class 0.000 title claims abstract description 90
- 239000000203 mixture Substances 0.000 title claims description 41
- 238000004519 manufacturing process Methods 0.000 title description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 477
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 217
- 125000001424 substituent group Chemical group 0.000 claims abstract description 216
- 125000003277 amino group Chemical group 0.000 claims abstract description 170
- 125000005843 halogen group Chemical group 0.000 claims abstract description 144
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 133
- 150000003839 salts Chemical class 0.000 claims abstract description 91
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 89
- 125000003118 aryl group Chemical group 0.000 claims abstract description 79
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 68
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims abstract description 51
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 49
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 40
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims abstract description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 34
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 34
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 31
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 30
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 26
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims abstract description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 21
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 18
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 17
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 15
- 125000000565 sulfonamide group Chemical group 0.000 claims abstract description 14
- 125000004755 (C2-C7) acylamino group Chemical group 0.000 claims abstract description 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 12
- 125000002252 acyl group Chemical group 0.000 claims abstract description 11
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical group NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000004429 atom Chemical group 0.000 claims abstract description 8
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims abstract description 7
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 6
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 150
- 125000006239 protecting group Chemical group 0.000 claims description 131
- 239000003112 inhibitor Substances 0.000 claims description 123
- 238000000034 method Methods 0.000 claims description 78
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 50
- 239000003623 enhancer Substances 0.000 claims description 49
- 108010041872 Islet Amyloid Polypeptide Proteins 0.000 claims description 45
- 102000036770 Islet Amyloid Polypeptide Human genes 0.000 claims description 45
- 206010012601 diabetes mellitus Diseases 0.000 claims description 45
- 239000008103 glucose Substances 0.000 claims description 43
- 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 claims description 41
- 239000000556 agonist Substances 0.000 claims description 38
- 239000003795 chemical substances by application Substances 0.000 claims description 37
- 201000010099 disease Diseases 0.000 claims description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 31
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 31
- 239000008280 blood Substances 0.000 claims description 30
- 210000004369 blood Anatomy 0.000 claims description 30
- 238000010521 absorption reaction Methods 0.000 claims description 27
- 230000002265 prevention Effects 0.000 claims description 25
- UPSFNXFLBMJUQW-UHFFFAOYSA-N 5-hydroxy-1-methylimidazolidine-2,4-dione Chemical compound CN1C(O)C(=O)NC1=O UPSFNXFLBMJUQW-UHFFFAOYSA-N 0.000 claims description 24
- 208000002249 Diabetes Complications Diseases 0.000 claims description 24
- 206010012655 Diabetic complications Diseases 0.000 claims description 24
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 claims description 24
- 230000015572 biosynthetic process Effects 0.000 claims description 24
- 239000003102 growth factor Substances 0.000 claims description 24
- 229940030600 antihypertensive agent Drugs 0.000 claims description 23
- 239000002220 antihypertensive agent Substances 0.000 claims description 23
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 22
- 206010022489 Insulin Resistance Diseases 0.000 claims description 20
- 201000001421 hyperglycemia Diseases 0.000 claims description 20
- 230000002401 inhibitory effect Effects 0.000 claims description 20
- 230000003914 insulin secretion Effects 0.000 claims description 20
- 102000004877 Insulin Human genes 0.000 claims description 19
- 108090001061 Insulin Proteins 0.000 claims description 19
- 229940123518 Sodium/glucose cotransporter 2 inhibitor Drugs 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 19
- 230000001965 increasing effect Effects 0.000 claims description 19
- 229940125396 insulin Drugs 0.000 claims description 19
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical class C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 claims description 18
- 229940123208 Biguanide Drugs 0.000 claims description 18
- 239000000048 adrenergic agonist Substances 0.000 claims description 18
- 229930182830 galactose Natural products 0.000 claims description 18
- 230000002440 hepatic effect Effects 0.000 claims description 18
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 16
- 229940122904 Glucagon receptor antagonist Drugs 0.000 claims description 16
- 101800000224 Glucagon-like peptide 1 Proteins 0.000 claims description 16
- 102000003638 Glucose-6-Phosphatase Human genes 0.000 claims description 16
- 108010086800 Glucose-6-Phosphatase Proteins 0.000 claims description 16
- 102100040918 Pro-glucagon Human genes 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- CDAISMWEOUEBRE-LKPKBOIGSA-N 1D-chiro-inositol Chemical compound O[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O CDAISMWEOUEBRE-LKPKBOIGSA-N 0.000 claims description 15
- 229940124213 Dipeptidyl peptidase 4 (DPP IV) inhibitor Drugs 0.000 claims description 15
- 229940121929 Insulin receptor kinase stimulant Drugs 0.000 claims description 15
- 229940124117 Pyruvate dehydrogenase inhibitor Drugs 0.000 claims description 15
- 229940123286 Tripeptidyl peptidase II inhibitor Drugs 0.000 claims description 15
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 15
- 239000003603 dipeptidyl peptidase IV inhibitor Substances 0.000 claims description 15
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims description 15
- 238000003786 synthesis reaction Methods 0.000 claims description 15
- 229940093498 Fructose bisphosphatase inhibitor Drugs 0.000 claims description 14
- 229940121931 Gluconeogenesis inhibitor Drugs 0.000 claims description 14
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 14
- 239000002830 appetite depressant Substances 0.000 claims description 14
- 239000002792 enkephalinase inhibitor Substances 0.000 claims description 14
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 14
- 201000008980 hyperinsulinism Diseases 0.000 claims description 14
- ROJNYKZWTOHRNU-UHFFFAOYSA-N 2-chloro-4,5-difluoro-n-[[2-methoxy-5-(methylcarbamoylamino)phenyl]carbamoyl]benzamide Chemical compound CNC(=O)NC1=CC=C(OC)C(NC(=O)NC(=O)C=2C(=CC(F)=C(F)C=2)Cl)=C1 ROJNYKZWTOHRNU-UHFFFAOYSA-N 0.000 claims description 13
- 239000005541 ACE inhibitor Substances 0.000 claims description 13
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 13
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 13
- 208000008589 Obesity Diseases 0.000 claims description 13
- 239000003288 aldose reductase inhibitor Substances 0.000 claims description 13
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 13
- 239000005516 coenzyme A Substances 0.000 claims description 13
- 229940093530 coenzyme a Drugs 0.000 claims description 13
- 239000002934 diuretic Substances 0.000 claims description 13
- 235000020824 obesity Nutrition 0.000 claims description 13
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 13
- 239000003801 protein tyrosine phosphatase 1B inhibitor Substances 0.000 claims description 13
- NMOVJBAGBXIKCG-VKAVYKQESA-N (3z)-n-(2-hydroxy-3-piperidin-1-ylpropoxy)pyridine-3-carboximidoyl chloride Chemical compound C1CCCCN1CC(O)CO\N=C(/Cl)C1=CC=CN=C1 NMOVJBAGBXIKCG-VKAVYKQESA-N 0.000 claims description 12
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical class OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 claims description 12
- SXKBTDJJEQQEGE-UHFFFAOYSA-N 3-(3,5-dibromo-4-hydroxy-benzoyl)-2-ethyl-benzofuran-6-sulfonic acid [4-(thiazol-2-ylsulfamoyl)-phenyl]-amide Chemical compound CCC=1OC2=CC(S(=O)(=O)NC=3C=CC(=CC=3)S(=O)(=O)NC=3SC=CN=3)=CC=C2C=1C(=O)C1=CC(Br)=C(O)C(Br)=C1 SXKBTDJJEQQEGE-UHFFFAOYSA-N 0.000 claims description 12
- 102000051325 Glucagon Human genes 0.000 claims description 12
- 108060003199 Glucagon Proteins 0.000 claims description 12
- 108010001483 Glycogen Synthase Proteins 0.000 claims description 12
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 12
- 206010020772 Hypertension Diseases 0.000 claims description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 12
- 108010025020 Nerve Growth Factor Proteins 0.000 claims description 12
- 102000001494 Sterol O-Acyltransferase Human genes 0.000 claims description 12
- 108010054082 Sterol O-acyltransferase Proteins 0.000 claims description 12
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 12
- DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 claims description 12
- 229950002409 bimoclomol Drugs 0.000 claims description 12
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 12
- 229960004666 glucagon Drugs 0.000 claims description 12
- 239000003877 glucagon like peptide 1 receptor agonist Substances 0.000 claims description 12
- 230000005764 inhibitory process Effects 0.000 claims description 12
- 229940053128 nerve growth factor Drugs 0.000 claims description 12
- 239000011734 sodium Substances 0.000 claims description 12
- 229940083542 sodium Drugs 0.000 claims description 12
- 229910052708 sodium Inorganic materials 0.000 claims description 12
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 claims description 12
- 229940045145 uridine Drugs 0.000 claims description 12
- 230000002485 urinary effect Effects 0.000 claims description 12
- VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 claims description 12
- 108010005094 Advanced Glycation End Products Proteins 0.000 claims description 11
- 229940118148 Aldose reductase inhibitor Drugs 0.000 claims description 11
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims description 11
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims description 11
- 229940127291 Calcium channel antagonist Drugs 0.000 claims description 11
- 229940118365 Endothelin receptor antagonist Drugs 0.000 claims description 11
- 102400001368 Epidermal growth factor Human genes 0.000 claims description 11
- 101800003838 Epidermal growth factor Proteins 0.000 claims description 11
- 101000716688 Homo sapiens Sodium/glucose cotransporter 1 Proteins 0.000 claims description 11
- 102000000853 LDL receptors Human genes 0.000 claims description 11
- 108010001831 LDL receptors Proteins 0.000 claims description 11
- 229940123635 Lipid peroxidase inhibitor Drugs 0.000 claims description 11
- 239000000867 Lipoxygenase Inhibitor Substances 0.000 claims description 11
- 229940123924 Protein kinase C inhibitor Drugs 0.000 claims description 11
- 229940089973 Sodium channel antagonist Drugs 0.000 claims description 11
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims description 11
- 229940126317 angiotensin II receptor antagonist Drugs 0.000 claims description 11
- 230000001142 anti-diarrhea Effects 0.000 claims description 11
- 229940125714 antidiarrheal agent Drugs 0.000 claims description 11
- 239000003793 antidiarrheal agent Substances 0.000 claims description 11
- 229940127218 antiplatelet drug Drugs 0.000 claims description 11
- 239000000799 cathartic agent Substances 0.000 claims description 11
- 239000002308 endothelin receptor antagonist Substances 0.000 claims description 11
- 229940116977 epidermal growth factor Drugs 0.000 claims description 11
- MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 claims description 11
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 claims description 11
- 102000052194 human SLC5A1 Human genes 0.000 claims description 11
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 11
- 239000003881 protein kinase C inhibitor Substances 0.000 claims description 11
- 239000003195 sodium channel blocking agent Substances 0.000 claims description 11
- 229940116269 uric acid Drugs 0.000 claims description 11
- 201000001320 Atherosclerosis Diseases 0.000 claims description 10
- 229940086609 Lipase inhibitor Drugs 0.000 claims description 10
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 10
- 229940122142 Lipoxygenase inhibitor Drugs 0.000 claims description 10
- 102100031545 Microsomal triglyceride transfer protein large subunit Human genes 0.000 claims description 10
- 229940122954 Transcription factor inhibitor Drugs 0.000 claims description 10
- 229920000080 bile acid sequestrant Polymers 0.000 claims description 10
- 239000000480 calcium channel blocker Substances 0.000 claims description 10
- 239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 claims description 10
- 239000004026 insulin derivative Substances 0.000 claims description 10
- 108010038232 microsomal triglyceride transfer protein Proteins 0.000 claims description 10
- 229940121649 protein inhibitor Drugs 0.000 claims description 10
- 239000012268 protein inhibitor Substances 0.000 claims description 10
- 239000004059 squalene synthase inhibitor Substances 0.000 claims description 10
- 230000002889 sympathetic effect Effects 0.000 claims description 10
- 229940124549 vasodilator Drugs 0.000 claims description 10
- 239000003071 vasodilator agent Substances 0.000 claims description 10
- 101710175516 14 kDa zinc-binding protein Proteins 0.000 claims description 9
- 229940122502 Cholesterol absorption inhibitor Drugs 0.000 claims description 9
- 102000004218 Insulin-Like Growth Factor I Human genes 0.000 claims description 9
- 108090000723 Insulin-Like Growth Factor I Proteins 0.000 claims description 9
- 229940123495 Squalene synthetase inhibitor Drugs 0.000 claims description 9
- 239000002981 blocking agent Substances 0.000 claims description 9
- 229940044551 receptor antagonist Drugs 0.000 claims description 9
- 239000002464 receptor antagonist Substances 0.000 claims description 9
- 229940122215 Sodium/bile acid cotransporter inhibitor Drugs 0.000 claims description 8
- 229940116731 Uricosuric agent Drugs 0.000 claims description 8
- 239000002552 dosage form Substances 0.000 claims description 8
- 239000003383 uricosuric agent Substances 0.000 claims description 8
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 7
- 229940122184 Carnitine palmitoyltransferase inhibitor Drugs 0.000 claims description 7
- 229940090955 Dipeptidase inhibitor Drugs 0.000 claims description 7
- 229940122783 Endothelin converting-enzyme inhibitor Drugs 0.000 claims description 7
- 206010019280 Heart failures Diseases 0.000 claims description 7
- 206010030113 Oedema Diseases 0.000 claims description 7
- 229940121886 Thyroid hormone receptor agonist Drugs 0.000 claims description 7
- 239000002857 endothelin converting enzyme inhibitor Substances 0.000 claims description 7
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 102000004316 Oxidoreductases Human genes 0.000 claims description 6
- 108090000854 Oxidoreductases Proteins 0.000 claims description 6
- 239000002404 acyltransferase inhibitor Substances 0.000 claims description 6
- 229940127095 analogue insulin Drugs 0.000 claims description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- CABVTRNMFUVUDM-VRHQGPGLSA-N (3S)-3-hydroxy-3-methylglutaryl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@@](O)(CC(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 CABVTRNMFUVUDM-VRHQGPGLSA-N 0.000 claims description 5
- 201000005569 Gout Diseases 0.000 claims description 5
- 201000001431 Hyperuricemia Diseases 0.000 claims description 5
- 238000013268 sustained release Methods 0.000 claims description 5
- 239000012730 sustained-release form Substances 0.000 claims description 5
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 5
- 229940123324 Acyltransferase inhibitor Drugs 0.000 claims description 4
- 102000004860 Dipeptidases Human genes 0.000 claims description 4
- 108090001081 Dipeptidases Proteins 0.000 claims description 4
- 208000027472 Galactosemias Diseases 0.000 claims description 4
- 229960004203 carnitine Drugs 0.000 claims description 4
- RGJOEKWQDUBAIZ-IBOSZNHHSA-N CoASH Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS)O[C@H]1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-IBOSZNHHSA-N 0.000 claims description 3
- 102000004357 Transferases Human genes 0.000 claims description 3
- 108090000992 Transferases Proteins 0.000 claims description 3
- 230000003113 alkalizing effect Effects 0.000 claims description 3
- 230000036528 appetite Effects 0.000 claims description 3
- 235000019789 appetite Nutrition 0.000 claims description 3
- RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 claims description 3
- KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 claims description 3
- 230000002608 insulinlike Effects 0.000 claims description 3
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 2
- 108091008776 CNR14-like Proteins 0.000 claims description 2
- 108091000080 Phosphotransferase Proteins 0.000 claims description 2
- 230000000702 anti-platelet effect Effects 0.000 claims description 2
- 239000003146 anticoagulant agent Substances 0.000 claims description 2
- 239000003613 bile acid Substances 0.000 claims description 2
- 235000012000 cholesterol Nutrition 0.000 claims description 2
- 102000020233 phosphotransferase Human genes 0.000 claims description 2
- 102100023995 Beta-nerve growth factor Human genes 0.000 claims 5
- 102000004190 Enzymes Human genes 0.000 claims 2
- 108090000790 Enzymes Proteins 0.000 claims 2
- 229940113549 Cholesterol inhibitor Drugs 0.000 claims 1
- 102000034534 Cotransporters Human genes 0.000 claims 1
- 108020003264 Cotransporters Proteins 0.000 claims 1
- 108050009340 Endothelin Proteins 0.000 claims 1
- 102000002045 Endothelin Human genes 0.000 claims 1
- 108010022535 Farnesyl-Diphosphate Farnesyltransferase Proteins 0.000 claims 1
- ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 235000015107 ale Nutrition 0.000 abstract 1
- -1 glucose monosaccharide Chemical class 0.000 description 104
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 92
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 84
- 238000006243 chemical reaction Methods 0.000 description 77
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 75
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
- 239000002904 solvent Substances 0.000 description 65
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 63
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
- 235000002639 sodium chloride Nutrition 0.000 description 57
- 239000012442 inert solvent Substances 0.000 description 55
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 238000010992 reflux Methods 0.000 description 50
- 239000012046 mixed solvent Substances 0.000 description 48
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 46
- 230000008569 process Effects 0.000 description 45
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 34
- 239000007858 starting material Substances 0.000 description 34
- 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 33
- 230000035484 reaction time Effects 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 238000005160 1H NMR spectroscopy Methods 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000003814 drug Substances 0.000 description 26
- 229940079593 drug Drugs 0.000 description 25
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 22
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 230000009102 absorption Effects 0.000 description 21
- 238000006460 hydrolysis reaction Methods 0.000 description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 21
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 20
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
- 230000002829 reductive effect Effects 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 230000007062 hydrolysis Effects 0.000 description 13
- 108091006277 SLC5A1 Proteins 0.000 description 12
- 102000058090 Sodium-Glucose Transporter 1 Human genes 0.000 description 12
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- KTFGWHSLIOZEKH-UHFFFAOYSA-N 5-benzyl-1h-pyrazole Chemical class C=1C=CC=CC=1CC1=CC=NN1 KTFGWHSLIOZEKH-UHFFFAOYSA-N 0.000 description 11
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 10
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 10
- 229910000024 caesium carbonate Inorganic materials 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 210000000813 small intestine Anatomy 0.000 description 9
- 239000012312 sodium hydride Substances 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- 239000005557 antagonist Substances 0.000 description 8
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 8
- 238000006482 condensation reaction Methods 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 102000015336 Nerve Growth Factor Human genes 0.000 description 7
- IQWIJOFMCDRBOO-UHFFFAOYSA-N [4-(3-phenylmethoxypropoxy)phenyl]methanol Chemical compound C1=CC(CO)=CC=C1OCCCOCC1=CC=CC=C1 IQWIJOFMCDRBOO-UHFFFAOYSA-N 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 7
- PSUXTZLDBVEZTD-UHFFFAOYSA-N 3-bromopropoxymethylbenzene Chemical compound BrCCCOCC1=CC=CC=C1 PSUXTZLDBVEZTD-UHFFFAOYSA-N 0.000 description 6
- OULBDBGCIUQACR-UHFFFAOYSA-N 4-[[4-(3-phenylmethoxypropoxy)phenyl]methyl]-5-propan-2-yl-1,2-dihydropyrazol-3-one Chemical compound N1NC(=O)C(CC=2C=CC(OCCCOCC=3C=CC=CC=3)=CC=2)=C1C(C)C OULBDBGCIUQACR-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 235000009518 sodium iodide Nutrition 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- RZTAMFZIAATZDJ-HNNXBMFYSA-N 5-o-ethyl 3-o-methyl (4s)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-HNNXBMFYSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- 229940122907 Phosphatase inhibitor Drugs 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000002168 alkylating agent Substances 0.000 description 5
- 229940100198 alkylating agent Drugs 0.000 description 5
- 235000021258 carbohydrate absorption Nutrition 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 229960003580 felodipine Drugs 0.000 description 5
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000005905 mesyloxy group Chemical group 0.000 description 5
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 5
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- WKNMKGVLOWGGOU-UHFFFAOYSA-N 2-aminoacetamide;hydron;chloride Chemical compound Cl.NCC(N)=O WKNMKGVLOWGGOU-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229940088597 hormone Drugs 0.000 description 4
- 239000005556 hormone Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000000018 receptor agonist Substances 0.000 description 4
- 229940044601 receptor agonist Drugs 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 3
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 3
- FWOHDAGPWDEWIB-UHFFFAOYSA-N 2-bromoethoxymethylbenzene Chemical compound BrCCOCC1=CC=CC=C1 FWOHDAGPWDEWIB-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 239000003148 4 aminobutyric acid receptor blocking agent Substances 0.000 description 3
- 102100034159 Beta-3 adrenergic receptor Human genes 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 102400000739 Corticotropin Human genes 0.000 description 3
- 101800000414 Corticotropin Proteins 0.000 description 3
- 102000048186 Endothelin-converting enzyme 1 Human genes 0.000 description 3
- 108030001679 Endothelin-converting enzyme 1 Proteins 0.000 description 3
- 102000016267 Leptin Human genes 0.000 description 3
- 108010092277 Leptin Proteins 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 239000000384 adrenergic alpha-2 receptor agonist Substances 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- 108040005346 beta3-adrenergic receptor activity proteins Proteins 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229960005069 calcium Drugs 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 3
- 229960000258 corticotropin Drugs 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000003572 glycogen synthase kinase 3 inhibitor Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 230000003345 hyperglycaemic effect Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- 229940039781 leptin Drugs 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 206010062198 microangiopathy Diseases 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000000021 stimulant Substances 0.000 description 3
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 2
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 2
- BOOOLEGQBVUTKC-NVQSDHBMSA-N (2e,4e)-3-methyl-5-[(1s,2s)-2-methyl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)cyclopropyl]penta-2,4-dienoic acid Chemical compound OC(=O)\C=C(/C)\C=C\[C@@H]1C[C@]1(C)C1=CC=C2C(C)(C)CCC(C)(C)C2=C1 BOOOLEGQBVUTKC-NVQSDHBMSA-N 0.000 description 2
- FOZFSEMFCIPOSZ-SPCKQMHLSA-N (2r,3r,4r,5s)-2-(hydroxymethyl)-1-[[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]piperidine-3,4,5-triol;trihydrate Chemical compound O.O.O.O[C@H]1[C@H](O)[C@@H](O)[C@@H](OC)O[C@@H]1CN1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1.O[C@H]1[C@H](O)[C@@H](O)[C@@H](OC)O[C@@H]1CN1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1 FOZFSEMFCIPOSZ-SPCKQMHLSA-N 0.000 description 2
- USVVENVKYJZFMW-ONEGZZNKSA-N (e)-carboxyiminocarbamic acid Chemical compound OC(=O)\N=N\C(O)=O USVVENVKYJZFMW-ONEGZZNKSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 2-amino-2-methylpropanamide Chemical compound CC(C)(N)C(N)=O ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 0.000 description 2
- OGJPSKLXUGOZFD-UHFFFAOYSA-N 4-[(4-phenylmethoxyphenyl)methyl]-5-propan-2-yl-1,2-dihydropyrazol-3-one Chemical compound N1NC(=O)C(CC=2C=CC(OCC=3C=CC=CC=3)=CC=2)=C1C(C)C OGJPSKLXUGOZFD-UHFFFAOYSA-N 0.000 description 2
- WHJJAQSRKKNNKR-UHFFFAOYSA-N 4-[[2-methyl-4-(2-phenylmethoxyethoxy)phenyl]methyl]-5-propan-2-yl-1,2-dihydropyrazol-3-one Chemical compound N1NC(=O)C(CC=2C(=CC(OCCOCC=3C=CC=CC=3)=CC=2)C)=C1C(C)C WHJJAQSRKKNNKR-UHFFFAOYSA-N 0.000 description 2
- RCAGCKFYRWCVQW-UHFFFAOYSA-N 4-[[4-(4-phenylmethoxybutoxy)phenyl]methyl]-5-propan-2-yl-1,2-dihydropyrazol-3-one Chemical compound N1NC(=O)C(CC=2C=CC(OCCCCOCC=3C=CC=CC=3)=CC=2)=C1C(C)C RCAGCKFYRWCVQW-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- 102000016912 Aldehyde Reductase Human genes 0.000 description 2
- 108010053754 Aldehyde reductase Proteins 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 108060001064 Calcitonin Proteins 0.000 description 2
- 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 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 2
- 101800001982 Cholecystokinin Proteins 0.000 description 2
- 102100025841 Cholecystokinin Human genes 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- 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 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 229930091371 Fructose Natural products 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 102000007390 Glycogen Phosphorylase Human genes 0.000 description 2
- 108010046163 Glycogen Phosphorylase Proteins 0.000 description 2
- 229940123856 Glycogen synthase kinase 3 inhibitor Drugs 0.000 description 2
- OMCPLEZZPVJJIS-UHFFFAOYSA-N Hypadil (TN) Chemical compound C1C(O[N+]([O-])=O)COC2=C1C=CC=C2OCC(O)CNC(C)C OMCPLEZZPVJJIS-UHFFFAOYSA-N 0.000 description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 238000007126 N-alkylation reaction Methods 0.000 description 2
- 238000010934 O-alkylation reaction Methods 0.000 description 2
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 2
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 108091006269 SLC5A2 Proteins 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 102000058081 Sodium-Glucose Transporter 2 Human genes 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- AUYYCJSJGJYCDS-LBPRGKRZSA-N Thyrolar Chemical class IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-LBPRGKRZSA-N 0.000 description 2
- KJADKKWYZYXHBB-XBWDGYHZSA-N Topiramic acid Chemical compound C1O[C@@]2(COS(N)(=O)=O)OC(C)(C)O[C@H]2[C@@H]2OC(C)(C)O[C@@H]21 KJADKKWYZYXHBB-XBWDGYHZSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 229940118484 Tyrosine phosphatase 1B inhibitor Drugs 0.000 description 2
- KLZUXDPJWSUAGO-UHFFFAOYSA-N [2-methyl-4-(2-phenylmethoxyethoxy)phenyl]methanol Chemical compound C1=C(CO)C(C)=CC(OCCOCC=2C=CC=CC=2)=C1 KLZUXDPJWSUAGO-UHFFFAOYSA-N 0.000 description 2
- JIWMYVFLOMJOTH-UHFFFAOYSA-N [2-methyl-4-(3-phenylmethoxypropoxy)phenyl]methanol Chemical compound C1=C(CO)C(C)=CC(OCCCOCC=2C=CC=CC=2)=C1 JIWMYVFLOMJOTH-UHFFFAOYSA-N 0.000 description 2
- JANXAAOLQGFURG-UHFFFAOYSA-N [4-(2-phenylmethoxyethoxy)phenyl]methanol Chemical compound C1=CC(CO)=CC=C1OCCOCC1=CC=CC=C1 JANXAAOLQGFURG-UHFFFAOYSA-N 0.000 description 2
- BZROTFMKPQIQDQ-UHFFFAOYSA-N [4-(4-phenylmethoxybutoxy)phenyl]methanol Chemical compound C1=CC(CO)=CC=C1OCCCCOCC1=CC=CC=C1 BZROTFMKPQIQDQ-UHFFFAOYSA-N 0.000 description 2
- 229960002632 acarbose Drugs 0.000 description 2
- XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 229940025084 amphetamine Drugs 0.000 description 2
- 239000000739 antihistaminic agent Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- BXUMISWXFKCEIA-UHFFFAOYSA-N benzyl (ne)-n-[amino(pyrazol-1-yl)methylidene]carbamate Chemical compound C1=CC=NN1C(N)=NC(=O)OCC1=CC=CC=C1 BXUMISWXFKCEIA-UHFFFAOYSA-N 0.000 description 2
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 2
- 150000004283 biguanides Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 229960004349 candesartan cilexetil Drugs 0.000 description 2
- 235000021257 carbohydrate digestion Nutrition 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229940107137 cholecystokinin Drugs 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229940052760 dopamine agonists Drugs 0.000 description 2
- 239000003136 dopamine receptor stimulating agent Substances 0.000 description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
- 229940125753 fibrate Drugs 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 230000004110 gluconeogenesis Effects 0.000 description 2
- 238000005858 glycosidation reaction Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 229960002003 hydrochlorothiazide 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
- 229960004569 indapamide Drugs 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 108020004999 messenger RNA Proteins 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 230000000407 monoamine reuptake Effects 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- XXGPJVZDKNCYDC-UHFFFAOYSA-N n,n'-dicyclohexylmethanediimine;hydrochloride Chemical compound Cl.C1CCCCC1N=C=NC1CCCCC1 XXGPJVZDKNCYDC-UHFFFAOYSA-N 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229950000754 nipradilol Drugs 0.000 description 2
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 description 2
- 229960002748 norepinephrine Drugs 0.000 description 2
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- NHZMQXZHNVQTQA-UHFFFAOYSA-N pyridoxamine Chemical compound CC1=NC=C(CO)C(CN)=C1O NHZMQXZHNVQTQA-UHFFFAOYSA-N 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000000952 serotonin receptor agonist Substances 0.000 description 2
- 239000003772 serotonin uptake inhibitor Substances 0.000 description 2
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
- NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 description 2
- 229960002920 sorbitol Drugs 0.000 description 2
- 239000003774 sulfhydryl reagent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 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 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 239000005495 thyroid hormone Substances 0.000 description 2
- 229940036555 thyroid hormone Drugs 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 229960004394 topiramate Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 1
- HMJIYCCIJYRONP-UHFFFAOYSA-N (+-)-Isradipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12 HMJIYCCIJYRONP-UHFFFAOYSA-N 0.000 description 1
- KIOUIMVIZXYLFV-BRFIBAHXSA-N (1r,7s,9ar,11ar)-3a-(1-hydroxyprop-2-enyl)-6,6,9a,11a-tetramethyl-1-(6-methylheptan-2-yl)-1,2,4,5,5a,7,8,9,10,11-decahydronaphtho[1,2-g][1]benzofuran-7-ol Chemical compound C([C@]12C)C[C@H](O)C(C)(C)C1CCC1=C2CC[C@]2(C)[C@@H](C(C)CCCC(C)C)COC21C(O)C=C KIOUIMVIZXYLFV-BRFIBAHXSA-N 0.000 description 1
- MLBHFBKZUPLWBD-ZETCQYMHSA-N (2S)-1-[3-(trifluoromethyl)phenyl]-2-propanamine Chemical compound C[C@H](N)CC1=CC=CC(C(F)(F)F)=C1 MLBHFBKZUPLWBD-ZETCQYMHSA-N 0.000 description 1
- HNODNXQAYXJFMQ-LQUSFLDPSA-N (2e,4e,6z)-3-methyl-7-(5,5,8,8-tetramethyl-3-propoxy-6,7-dihydronaphthalen-2-yl)octa-2,4,6-trienoic acid Chemical compound CC1(C)CCC(C)(C)C2=C1C=C(\C(C)=C/C=C/C(/C)=C/C(O)=O)C(OCCC)=C2 HNODNXQAYXJFMQ-LQUSFLDPSA-N 0.000 description 1
- FONCZICQWCUXEB-RUZDIDTESA-N (2r)-2-[4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)-2,6-dimethylphenoxy]-3-phenylpropanoic acid Chemical compound C([C@@H](OC1=C(C)C=C(C=C1C)C=1C2=CC=CC=C2C(Br)=C2SC(=C(C2=1)C)C)C(O)=O)C1=CC=CC=C1 FONCZICQWCUXEB-RUZDIDTESA-N 0.000 description 1
- QHSRPPJQBFQWSC-OJDZSJEKSA-N (2r)-2-[[(2r)-2-[[(2s)-2-(azepane-1-carbonylamino)-4-methylpentanoyl]amino]-3-(1-formylindol-3-yl)propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@H](CC=1C2=CC=CC=C2N(C=O)C=1)C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)C(=O)N1CCCCCC1 QHSRPPJQBFQWSC-OJDZSJEKSA-N 0.000 description 1
- XSOXUIXLUNBLJA-RNRVQEDPSA-N (2r)-6-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid Chemical compound C1([C@@H](O)CN[C@@H](CC=2C=C3OC[C@@H](OC3=CC=2)C(O)=O)C)=CC=CC(Cl)=C1 XSOXUIXLUNBLJA-RNRVQEDPSA-N 0.000 description 1
- VCIPQQCYKMORDY-KBYFLBCBSA-N (2r,3r,4s,5s,6r)-2-(hydroxymethyl)-6-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]piperidine-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)N[C@@H]1CO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 VCIPQQCYKMORDY-KBYFLBCBSA-N 0.000 description 1
- QIJLJZOGPPQCOG-NFAWXSAZSA-N (2s)-1-[(2s)-3-[(2r)-2-(cyclohexanecarbonylamino)propanoyl]sulfanyl-2-methylpropanoyl]pyrrolidine-2-carboxylic acid Chemical compound N([C@H](C)C(=O)SC[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)C(=O)C1CCCCC1 QIJLJZOGPPQCOG-NFAWXSAZSA-N 0.000 description 1
- BAVDEDVBIHTHJQ-UVJOBNTFSA-N (2s)-1-[(2s)-6-amino-2-[[(1s)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid;hydrate Chemical compound O.C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 BAVDEDVBIHTHJQ-UVJOBNTFSA-N 0.000 description 1
- JGLICGWVWBQYCQ-LURJTMIESA-N (2s)-2-[(2-nitrophenyl)sulfonylamino]propanamide Chemical compound NC(=O)[C@H](C)NS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O JGLICGWVWBQYCQ-LURJTMIESA-N 0.000 description 1
- HWEMEKZYQCJVEZ-PPHPATTJSA-N (2s)-2-[(7-fluoro-2,3-dihydro-1h-inden-4-yl)oxymethyl]morpholine;hydrochloride Chemical compound Cl.C1=2CCCC=2C(F)=CC=C1OC[C@@H]1CNCCO1 HWEMEKZYQCJVEZ-PPHPATTJSA-N 0.000 description 1
- YPGILAVWVRBSAJ-MOPGFXCFSA-N (2s)-2-[[(2s)-2-benzyl-3-sulfanylpropanoyl]amino]-3-[4-(1,3-thiazol-2-yl)phenyl]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)[C@@H](CS)CC=1C=CC=CC=1)C(C=C1)=CC=C1C1=NC=CS1 YPGILAVWVRBSAJ-MOPGFXCFSA-N 0.000 description 1
- GKYIONYOYVKKQI-MPGHIAIKSA-N (2s)-2-[[(2s,3r)-2-(benzoylsulfanylmethyl)-3-phenylbutanoyl]amino]propanoic acid Chemical compound C([C@H](C(=O)N[C@@H](C)C(O)=O)[C@@H](C)C=1C=CC=CC=1)SC(=O)C1=CC=CC=C1 GKYIONYOYVKKQI-MPGHIAIKSA-N 0.000 description 1
- LPUDGHQMOAHMMF-JBACZVJFSA-N (2s)-2-[[[(2s)-6-amino-2-(methanesulfonamido)hexanoyl]amino]methyl]-3-[1-[[(1s)-1-carboxy-2-(4-hydroxyphenyl)ethyl]carbamoyl]cyclopentyl]propanoic acid Chemical compound N([C@@H](CC=1C=CC(O)=CC=1)C(O)=O)C(=O)C1(C[C@@H](CNC(=O)[C@H](CCCCN)NS(=O)(=O)C)C(O)=O)CCCC1 LPUDGHQMOAHMMF-JBACZVJFSA-N 0.000 description 1
- YKFCISHFRZHKHY-NGQGLHOPSA-N (2s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid;trihydrate Chemical compound O.O.O.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 YKFCISHFRZHKHY-NGQGLHOPSA-N 0.000 description 1
- QNDFBOXBUCDYNZ-NRFANRHFSA-N (2s)-2-ethoxy-3-[4-[2-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=CC=C(NC(=O)OC(C)(C)C)C=C1 QNDFBOXBUCDYNZ-NRFANRHFSA-N 0.000 description 1
- RDGUFKZGMLPVHL-QFIPXVFZSA-N (2s)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-(propylamino)propanoic acid Chemical compound C1=CC(C[C@H](NCCC)C(O)=O)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 RDGUFKZGMLPVHL-QFIPXVFZSA-N 0.000 description 1
- CRUVAUSVWLATAE-ZDUSSCGKSA-N (2s)-3-dibenzofuran-3-yl-2-(phosphonomethylamino)propanoic acid Chemical compound C1=CC=C2C3=CC=C(C[C@@H](C(=O)O)NCP(O)(O)=O)C=C3OC2=C1 CRUVAUSVWLATAE-ZDUSSCGKSA-N 0.000 description 1
- OAEWNSKRLBVVBV-QSEAXJEQSA-N (2s,3r,4s)-1-[2-(dibutylamino)-2-oxoethyl]-2-(2,2-dimethylpentyl)-4-(7-methoxy-1,3-benzodioxol-5-yl)pyrrolidine-3-carboxylic acid Chemical compound OC(=O)[C@H]1[C@H](CC(C)(C)CCC)N(CC(=O)N(CCCC)CCCC)C[C@@H]1C(C=C1OC)=CC2=C1OCO2 OAEWNSKRLBVVBV-QSEAXJEQSA-N 0.000 description 1
- FXAAOALUHHXBSO-ILDUYXDCSA-N (3,3,5-trimethylcyclohexyl) (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)[C@H]1NC(=O)CC1 FXAAOALUHHXBSO-ILDUYXDCSA-N 0.000 description 1
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 1
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- JICDBMXIQNEXKV-QFIPXVFZSA-N (3r)-3-(4-quinolin-6-ylphenyl)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound N1=CC=CC2=CC(C3=CC=C(C=C3)[C@@]3(C4CCN(CC4)C3)O)=CC=C21 JICDBMXIQNEXKV-QFIPXVFZSA-N 0.000 description 1
- KTFMPDDJYRFWQE-DDWIOCJRSA-N (3r)-3-propanoyloxy-4-(trimethylazaniumyl)butanoate;hydrochloride Chemical compound [Cl-].CCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C KTFMPDDJYRFWQE-DDWIOCJRSA-N 0.000 description 1
- CKFWDLFFXXVSBJ-DHIUTWEWSA-N (3r,5r)-3-butyl-3-ethyl-7,8-dimethoxy-5-phenyl-4,5-dihydro-2h-1$l^{6},4-benzothiazepine 1,1-dioxide Chemical compound C1([C@@H]2C3=CC(OC)=C(OC)C=C3S(=O)(=O)C[C@@](N2)(CC)CCCC)=CC=CC=C1 CKFWDLFFXXVSBJ-DHIUTWEWSA-N 0.000 description 1
- HPFIYXJJZZWEPC-MMKWGKFASA-N (3r,5s,6e)-9,9-bis(4-fluorophenyl)-3,5-dihydroxy-8-(1-methyltetrazol-5-yl)nona-6,8-dienoic acid Chemical compound CN1N=NN=C1C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 HPFIYXJJZZWEPC-MMKWGKFASA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- RICKQPKTSOSCOF-HKUYNNGSSA-N (3s)-2-[(2s)-2-amino-3-(1h-indol-3-yl)propanoyl]-3,4-dihydro-1h-isoquinoline-3-carboxylic acid Chemical compound C1C2=CC=CC=C2C[C@@H](C(O)=O)N1C(=O)[C@@H](N)CC1=CNC2=CC=CC=C12 RICKQPKTSOSCOF-HKUYNNGSSA-N 0.000 description 1
- DLOJBPLQFCFYKX-QQYYTUMTSA-N (3s)-4-[[(2r)-1-[2-[[(2s)-2-[[1h-indol-3-ylmethyl-[2-[[(2s)-2-[3-(4-sulfooxyphenyl)propanoylamino]hexanoyl]amino]acetyl]carbamoyl]amino]hexanoyl]carbamoyl]phenyl]propan-2-yl]amino]-3-(methylamino)-4-oxobutanoic acid Chemical compound N([C@@H](CCCC)C(=O)NCC(=O)N(CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCCC)C(=O)NC(=O)C=1C(=CC=CC=1)C[C@@H](C)NC(=O)[C@H](CC(O)=O)NC)C(=O)CCC1=CC=C(OS(O)(=O)=O)C=C1 DLOJBPLQFCFYKX-QQYYTUMTSA-N 0.000 description 1
- VMDKRSNUUUUARH-MQDBWYGVSA-N (3s)-4-[[(2s)-1-[[(2s)-2-[[(2s)-3-(1h-indol-3-yl)-2-[[2-[[(2s)-2-[[2-(4-sulfooxyphenyl)acetyl]amino]hexanoyl]amino]acetyl]amino]propanoyl]amino]hexanoyl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(methylamino)-4-oxobutanoic acid Chemical compound N([C@@H](CCCC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCCC)C(=O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(O)=O)NC)C(=O)CC1=CC=C(OS(O)(=O)=O)C=C1 VMDKRSNUUUUARH-MQDBWYGVSA-N 0.000 description 1
- 108010040581 (4-hydroxy-3-(2-(2-propenyl)-4-quinoline)benzoyl)-(3-chloro-4-hydroxyarginyl)-(3-hydroxy-3-methylprolyl)-dehydrovaline Proteins 0.000 description 1
- BMHZAHGTGIZZCT-LJQANCHMSA-N (4r)-2-[(4-bromo-2-fluorophenyl)methyl]-6-fluorospiro[isoquinoline-4,3'-pyrrolidine]-1,2',3,5'-tetrone Chemical compound C1([C@]2(C(NC(=O)C2)=O)C2=O)=CC(F)=CC=C1C(=O)N2CC1=CC=C(Br)C=C1F BMHZAHGTGIZZCT-LJQANCHMSA-N 0.000 description 1
- VIMMECPCYZXUCI-MMKWGKFASA-N (4r,6s)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical compound CN1N=NN=C1C(\C=C\[C@H]1OC(=O)C[C@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MMKWGKFASA-N 0.000 description 1
- VDSBXXDKCUBMQC-HNGSOEQISA-N (4r,6s)-6-[(e)-2-[2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethylcyclohexen-1-yl]ethenyl]-4-hydroxyoxan-2-one Chemical compound C1=C(F)C(C)=CC(C=2CC(C)(C)CC(C)(C)C=2\C=C\[C@H]2OC(=O)C[C@H](O)C2)=C1 VDSBXXDKCUBMQC-HNGSOEQISA-N 0.000 description 1
- AIEZUMPHACQOGT-BJESRGMDSA-N (4s,7s,12br)-7-[[(2s)-2-acetylsulfanyl-3-phenylpropanoyl]amino]-6-oxo-2,3,4,7,8,12b-hexahydro-1h-pyrido[2,1-a][2]benzazepine-4-carboxylic acid Chemical compound C([C@H](SC(=O)C)C(=O)N[C@@H]1C(N2[C@@H](CCC[C@@H]2C2=CC=CC=C2C1)C(O)=O)=O)C1=CC=CC=C1 AIEZUMPHACQOGT-BJESRGMDSA-N 0.000 description 1
- IUHMIOAKWHUFKU-YINIXLNUSA-N (5s,6r,7r)-5-(1,3-benzodioxol-5-yl)-2-butyl-7-[2-[(2s)-2-carboxypropyl]-4-methoxyphenyl]-6,7-dihydro-5h-cyclopenta[b]pyridine-6-carboxylic acid Chemical compound C1([C@H]2[C@@H]([C@H](C3=CC=C(N=C32)CCCC)C=2C=C3OCOC3=CC=2)C(O)=O)=CC=C(OC)C=C1C[C@H](C)C(O)=O IUHMIOAKWHUFKU-YINIXLNUSA-N 0.000 description 1
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 description 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
- METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- PVHUJELLJLJGLN-INIZCTEOSA-N (S)-nitrendipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 PVHUJELLJLJGLN-INIZCTEOSA-N 0.000 description 1
- WLRMANUAADYWEA-NWASOUNVSA-N (S)-timolol maleate Chemical compound OC(=O)\C=C/C(O)=O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 WLRMANUAADYWEA-NWASOUNVSA-N 0.000 description 1
- LONWRQOYFPYMQD-DTQAZKPQSA-N (e)-n-[6-methoxy-5-(2-methoxyphenoxy)-2-pyrimidin-2-ylpyrimidin-4-yl]-2-phenylethenesulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=CC=CN=2)OC)=C1NS(=O)(=O)\C=C\C1=CC=CC=C1 LONWRQOYFPYMQD-DTQAZKPQSA-N 0.000 description 1
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- FTUXVMVEKYLKGE-WECFPGDBSA-N (z)-but-2-enedioic acid;[(2s,3s)-8-chloro-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl] acetate Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=C(Cl)C=C2S1 FTUXVMVEKYLKGE-WECFPGDBSA-N 0.000 description 1
- 125000004814 1,1-dimethylethylene group Chemical group [H]C([H])([H])C([*:1])(C([H])([H])[H])C([H])([H])[*:2] 0.000 description 1
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 1
- UUOJIACWOAYWEZ-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(2-methyl-1H-indol-4-yl)oxy]propan-2-yl benzoate Chemical compound C1=CC=C2NC(C)=CC2=C1OCC(CNC(C)(C)C)OC(=O)C1=CC=CC=C1 UUOJIACWOAYWEZ-UHFFFAOYSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- GEVQMCFWDDZLMU-UHFFFAOYSA-N 1-[1-(3-ethoxyphenyl)propyl]-7-(pyrimidin-5-ylmethoxy)-4,5-dihydrobenzo[g]indazole-3-carboxylic acid Chemical compound CCOC1=CC=CC(C(CC)N2C=3C4=CC=C(OCC=5C=NC=NC=5)C=C4CCC=3C(C(O)=O)=N2)=C1 GEVQMCFWDDZLMU-UHFFFAOYSA-N 0.000 description 1
- KFNNPQDSPLWLCX-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)cyclobutyl]-n,n,3-trimethylbutan-1-amine;hydron;chloride;hydrate Chemical compound O.Cl.C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 KFNNPQDSPLWLCX-UHFFFAOYSA-N 0.000 description 1
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 1
- VDTWKXAPIQBOMO-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)-4,6-di(propan-2-yl)-3-propylphenyl]ethanol Chemical compound CCCC1=C(C(C)C)C=C(C(C)C)C(C(C)O)=C1C1=CC=C(F)C=C1 VDTWKXAPIQBOMO-UHFFFAOYSA-N 0.000 description 1
- POQMHHDKXWTFHB-HKBQPEDESA-N 1-[5-[(s)-(4,5-diphenyl-1h-imidazol-2-yl)sulfinyl]pentyl]-3,5-dimethylpyrazole Chemical compound N1=C(C)C=C(C)N1CCCCC[S@](=O)C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 POQMHHDKXWTFHB-HKBQPEDESA-N 0.000 description 1
- PMGZJNCIQHGNLT-UHFFFAOYSA-N 1-[bis(2,2-dimethylpropanoyloxymethoxy)phosphoryl]-4-(3-phenoxyphenyl)butane-1-sulfonic acid Chemical compound CC(C)(C)C(=O)OCOP(=O)(OCOC(=O)C(C)(C)C)C(S(O)(=O)=O)CCCC1=CC=CC(OC=2C=CC=CC=2)=C1 PMGZJNCIQHGNLT-UHFFFAOYSA-N 0.000 description 1
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 1
- NHVQKYFNCQUKFI-UHFFFAOYSA-N 1-bromo-2-methyl-4-(3-phenylmethoxypropoxy)benzene Chemical compound C1=C(Br)C(C)=CC(OCCCOCC=2C=CC=CC=2)=C1 NHVQKYFNCQUKFI-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- AKJWTZIUYIFCCS-UHFFFAOYSA-N 1-cycloheptyl-1-[[3-[[cycloheptyl-[[4-(dimethylamino)phenyl]carbamoyl]amino]methyl]phenyl]methyl]-3-[4-(dimethylamino)phenyl]urea;dihydrochloride Chemical compound Cl.Cl.C1=CC(N(C)C)=CC=C1NC(=O)N(C1CCCCCC1)CC1=CC=CC(CN(C2CCCCCC2)C(=O)NC=2C=CC(=CC=2)N(C)C)=C1 AKJWTZIUYIFCCS-UHFFFAOYSA-N 0.000 description 1
- SIHFCVXQGXGQQO-UHFFFAOYSA-N 1-cyclohexyl-1-[[4-[[cyclohexyl-[[4-(dimethylamino)phenyl]carbamoyl]amino]methyl]cyclohexyl]methyl]-3-[4-(dimethylamino)phenyl]urea Chemical compound C1=CC(N(C)C)=CC=C1NC(=O)N(C1CCCCC1)CC1CCC(CN(C2CCCCC2)C(=O)NC=2C=CC(=CC=2)N(C)C)CC1 SIHFCVXQGXGQQO-UHFFFAOYSA-N 0.000 description 1
- KFRPWMWQOMPNMA-UHFFFAOYSA-N 1-heptyl-1-[[4-(3-methylbutyl)phenyl]methyl]-3-(2,4,6-trifluorophenyl)urea Chemical compound FC=1C=C(F)C=C(F)C=1NC(=O)N(CCCCCCC)CC1=CC=C(CCC(C)C)C=C1 KFRPWMWQOMPNMA-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000006411 1-propenylene group Chemical group [H]\C(*)=C(\[H])C([H])([H])[H] 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- OIWIYLWZIIJNHU-UHFFFAOYSA-N 1-sulfanylpyrazole Chemical compound SN1C=CC=N1 OIWIYLWZIIJNHU-UHFFFAOYSA-N 0.000 description 1
- ICFGFAUMBISMLR-UHFFFAOYSA-N 1h-pyrazole-5-carbaldehyde Chemical class O=CC=1C=CNN=1 ICFGFAUMBISMLR-UHFFFAOYSA-N 0.000 description 1
- WAFNZAURAWBNDZ-UHFFFAOYSA-N 2,2-dimethyl-N-(2,4,6-trimethoxyphenyl)dodecanamide Chemical compound CCCCCCCCCCC(C)(C)C(=O)NC1=C(OC)C=C(OC)C=C1OC WAFNZAURAWBNDZ-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- QCCHBHSAIQIQGO-UHFFFAOYSA-N 2,7-difluorospiro[fluorene-9,5'-imidazolidine]-2',4'-dione Chemical compound C12=CC(F)=CC=C2C2=CC=C(F)C=C2C21NC(=O)NC2=O QCCHBHSAIQIQGO-UHFFFAOYSA-N 0.000 description 1
- NVYSVDRYESXWBD-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfanyl)-1-(3,4-dihydroxyphenyl)ethanone Chemical compound C1=C(O)C(O)=CC=C1C(=O)CSC1=NC2=CC=CC=C2N1 NVYSVDRYESXWBD-UHFFFAOYSA-N 0.000 description 1
- FNLNSQHJKVQCBP-UHFFFAOYSA-N 2-(3-sulfanylpropyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CCCS FNLNSQHJKVQCBP-UHFFFAOYSA-N 0.000 description 1
- 239000003315 2-(4-chlorophenoxy)-2-methylpropanoic acid Substances 0.000 description 1
- RIMAGTAWNVQRCT-UHFFFAOYSA-N 2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalene-2-carbonyl)benzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C(=O)C1=CC=CC=C1C(O)=O RIMAGTAWNVQRCT-UHFFFAOYSA-N 0.000 description 1
- DEMLYXMVPJAVFU-UHFFFAOYSA-N 2-(chloromethyl)oxirane;2-methyl-1h-imidazole Chemical compound ClCC1CO1.CC1=NC=CN1 DEMLYXMVPJAVFU-UHFFFAOYSA-N 0.000 description 1
- VTAKZNRDSPNOAU-UHFFFAOYSA-M 2-(chloromethyl)oxirane;hydron;prop-2-en-1-amine;n-prop-2-enyldecan-1-amine;trimethyl-[6-(prop-2-enylamino)hexyl]azanium;dichloride Chemical compound Cl.[Cl-].NCC=C.ClCC1CO1.CCCCCCCCCCNCC=C.C[N+](C)(C)CCCCCCNCC=C VTAKZNRDSPNOAU-UHFFFAOYSA-M 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- UKHLQJAHGDFIDT-UHFFFAOYSA-N 2-[(2-nitrophenyl)sulfonylamino]acetamide Chemical compound NC(=O)CNS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O UKHLQJAHGDFIDT-UHFFFAOYSA-N 0.000 description 1
- XMQODGUTLZXUGZ-RPBOFIJWSA-N 2-[(3s)-3-[[1-[(2r)-2-ethoxycarbonyl-4-phenylbutyl]cyclopentanecarbonyl]amino]-2-oxo-4,5-dihydro-3h-1-benzazepin-1-yl]acetic acid Chemical compound C([C@@H](C(=O)OCC)CC1(CCCC1)C(=O)N[C@@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 XMQODGUTLZXUGZ-RPBOFIJWSA-N 0.000 description 1
- FEDJGPQLLNQAIY-UHFFFAOYSA-N 2-[(6-oxo-1h-pyridazin-3-yl)oxy]acetic acid Chemical compound OC(=O)COC=1C=CC(=O)NN=1 FEDJGPQLLNQAIY-UHFFFAOYSA-N 0.000 description 1
- IRGLQUMAHASUTG-IUCAKERBSA-N 2-[(6s,9s)-3-ethoxycarbonyl-6-methyl-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-9-yl]acetic acid Chemical compound OC(=O)C[C@@H]1CC[C@H](C)N2C(=O)C(C(=O)OCC)=CN=C21 IRGLQUMAHASUTG-IUCAKERBSA-N 0.000 description 1
- YREIRIKJAMPPHC-UHFFFAOYSA-N 2-[3-[(3-nitrophenyl)methyl]-2,4,5-trioxoimidazolidin-1-yl]acetic acid Chemical compound O=C1C(=O)N(CC(=O)O)C(=O)N1CC1=CC=CC([N+]([O-])=O)=C1 YREIRIKJAMPPHC-UHFFFAOYSA-N 0.000 description 1
- DLZGQGBHYCAKQA-UHFFFAOYSA-N 2-[3-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methyl]indol-1-yl]acetic acid;hydrate Chemical compound O.C12=CC=CC=C2N(CC(=O)O)C=C1CC1=NC2=C(F)C(F)=CC(F)=C2S1 DLZGQGBHYCAKQA-UHFFFAOYSA-N 0.000 description 1
- LKBFFDOJUKLQNY-UHFFFAOYSA-N 2-[3-[(4-bromo-2-fluorophenyl)methyl]-4-oxo-1-phthalazinyl]acetic acid Chemical compound O=C1C2=CC=CC=C2C(CC(=O)O)=NN1CC1=CC=C(Br)C=C1F LKBFFDOJUKLQNY-UHFFFAOYSA-N 0.000 description 1
- ZGGNJJJYUVRADP-ACJLOTCBSA-N 2-[4-[(2R)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]phenoxy]acetic acid Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(Cl)C=CC=1)C1=CC=C(OCC(O)=O)C=C1 ZGGNJJJYUVRADP-ACJLOTCBSA-N 0.000 description 1
- BKONADSQADEJJP-SFTDATJTSA-N 2-[4-[(2s)-2-[[(1s)-1-carboxy-2-phenylethyl]carbamoylamino]-3-oxo-3-(pentylamino)propyl]phenoxy]propanedioic acid Chemical compound C([C@@H](C(=O)NCCCCC)NC(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C1=CC=C(OC(C(O)=O)C(O)=O)C=C1 BKONADSQADEJJP-SFTDATJTSA-N 0.000 description 1
- KCEFVYIWOQSJCH-LMOVPXPDSA-N 2-[4-[2-[[(2r)-2-hydroxy-2-phenylethyl]amino]ethoxy]phenyl]acetic acid;hydrochloride Chemical compound Cl.C([C@H](O)C=1C=CC=CC=1)NCCOC1=CC=C(CC(O)=O)C=C1 KCEFVYIWOQSJCH-LMOVPXPDSA-N 0.000 description 1
- RVMBDLSFFNKKLG-SFHVURJKSA-N 2-[4-[2-[[(2s)-2-hydroxy-3-phenoxypropyl]amino]ethoxy]phenoxy]-n-(2-methoxyethyl)acetamide Chemical compound C1=CC(OCC(=O)NCCOC)=CC=C1OCCNC[C@H](O)COC1=CC=CC=C1 RVMBDLSFFNKKLG-SFHVURJKSA-N 0.000 description 1
- MUGOTNWCTZMBLV-UHFFFAOYSA-N 2-[4-oxo-2-(2-propan-2-ylidenehydrazinyl)-1,3-thiazol-5-yl]-n-phenylacetamide Chemical compound S1C(NN=C(C)C)=NC(=O)C1CC(=O)NC1=CC=CC=C1 MUGOTNWCTZMBLV-UHFFFAOYSA-N 0.000 description 1
- MKJQESRCXYYHFR-UHFFFAOYSA-N 2-[7-(2,2-dimethylpropanoylamino)-4,6-dimethyl-1-octyl-2,3-dihydroindol-5-yl]acetic acid;sulfuric acid Chemical compound OS(O)(=O)=O.CC(C)(C)C(=O)NC1=C(C)C(CC(O)=O)=C(C)C2=C1N(CCCCCCCC)CC2.CC(C)(C)C(=O)NC1=C(C)C(CC(O)=O)=C(C)C2=C1N(CCCCCCCC)CC2 MKJQESRCXYYHFR-UHFFFAOYSA-N 0.000 description 1
- MCHCGWZNXSZKJY-OEAKJJBVSA-N 2-[[2-[2-butyl-4-[(e)-2-carboxy-3-(6-methoxy-1,3-benzodioxol-5-yl)prop-1-enyl]pyrazol-3-yl]-5-methoxyphenoxy]methyl]benzoic acid Chemical compound CCCCN1N=CC(\C=C(/CC=2C(=CC=3OCOC=3C=2)OC)C(O)=O)=C1C1=CC=C(OC)C=C1OCC1=CC=CC=C1C(O)=O MCHCGWZNXSZKJY-OEAKJJBVSA-N 0.000 description 1
- FHEYFIGWYQJVDR-ACJLOTCBSA-N 2-[[3-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1h-indol-7-yl]oxy]acetic acid Chemical compound C1([C@@H](O)CN[C@@H](CC=2C3=CC=CC(OCC(O)=O)=C3NC=2)C)=CC=CC(Cl)=C1 FHEYFIGWYQJVDR-ACJLOTCBSA-N 0.000 description 1
- NSVFSAJIGAJDMR-UHFFFAOYSA-N 2-[benzyl(phenyl)amino]ethyl 5-(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CC=1NC(C)=C(C(=O)OCCN(CC=2C=CC=CC=2)C=2C=CC=CC=2)C(C=2C=C(C=CC=2)[N+]([O-])=O)C=1P1(=O)OCC(C)(C)CO1 NSVFSAJIGAJDMR-UHFFFAOYSA-N 0.000 description 1
- BJBCSGQLZQGGIQ-QGZVFWFLSA-N 2-acetamidoethyl (2r)-2-(4-chlorophenyl)-2-[3-(trifluoromethyl)phenoxy]acetate Chemical compound O([C@@H](C(=O)OCCNC(=O)C)C=1C=CC(Cl)=CC=1)C1=CC=CC(C(F)(F)F)=C1 BJBCSGQLZQGGIQ-QGZVFWFLSA-N 0.000 description 1
- CCTREOMTIFSZAU-OGFXRTJISA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;5-[(3r)-dithiolan-3-yl]pentanoic acid Chemical compound OCC(N)(CO)CO.OC(=O)CCCC[C@@H]1CCSS1 CCTREOMTIFSZAU-OGFXRTJISA-N 0.000 description 1
- UBDZFAGVPPMTIT-UHFFFAOYSA-N 2-aminoguanidine;hydron;chloride Chemical compound [Cl-].NC(N)=N[NH3+] UBDZFAGVPPMTIT-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 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 1
- WMUIIGVAWPWQAW-UHFFFAOYSA-N 2-ethoxy-3-[4-(2-phenoxazin-10-ylethoxy)phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C2=CC=CC=C2OC2=CC=CC=C21 WMUIIGVAWPWQAW-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- QKVCSJBBYNYZNM-UHFFFAOYSA-N 2-methyl-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound OC(=O)C(C)(C)NC(=O)OCC1=CC=CC=C1 QKVCSJBBYNYZNM-UHFFFAOYSA-N 0.000 description 1
- JSQSMUUUWOOZCJ-UHFFFAOYSA-N 2-methyl-2-[(2-nitrophenyl)sulfonylamino]propanamide Chemical compound NC(=O)C(C)(C)NS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O JSQSMUUUWOOZCJ-UHFFFAOYSA-N 0.000 description 1
- TYEFTVXWOJQNJF-UHFFFAOYSA-N 2-methyl-4-(3-phenylmethoxypropoxy)benzaldehyde Chemical compound C1=C(C=O)C(C)=CC(OCCCOCC=2C=CC=CC=2)=C1 TYEFTVXWOJQNJF-UHFFFAOYSA-N 0.000 description 1
- HZOABPDJUQEYFK-UHFFFAOYSA-N 2-methyl-n-[4-(1,2,3,4-tetrahydro-1,5-benzodiazepine-5-carbonyl)phenyl]benzamide Chemical compound CC1=CC=CC=C1C(=O)NC1=CC=C(C(=O)N2C3=CC=CC=C3NCCC2)C=C1 HZOABPDJUQEYFK-UHFFFAOYSA-N 0.000 description 1
- YZQLWPMZQVHJED-UHFFFAOYSA-N 2-methylpropanethioic acid S-[2-[[[1-(2-ethylbutyl)cyclohexyl]-oxomethyl]amino]phenyl] ester Chemical compound C=1C=CC=C(SC(=O)C(C)C)C=1NC(=O)C1(CC(CC)CC)CCCCC1 YZQLWPMZQVHJED-UHFFFAOYSA-N 0.000 description 1
- WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 1
- BCSVCWVQNOXFGL-UHFFFAOYSA-N 3,4-dihydro-4-oxo-3-((5-trifluoromethyl-2-benzothiazolyl)methyl)-1-phthalazine acetic acid Chemical compound O=C1C2=CC=CC=C2C(CC(=O)O)=NN1CC1=NC2=CC(C(F)(F)F)=CC=C2S1 BCSVCWVQNOXFGL-UHFFFAOYSA-N 0.000 description 1
- TVXOXGBTADZYCZ-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-1-[5-[(4,5-diphenyl-1h-imidazol-2-yl)sulfanyl]pentyl]-1-heptylurea Chemical compound C=1C=C(F)C=C(F)C=1NC(=O)N(CCCCCCC)CCCCCSC(N1)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 TVXOXGBTADZYCZ-UHFFFAOYSA-N 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- QLMBAIRFQQLJJX-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol;hydron;chloride Chemical compound Cl.O1CC2=C(O)C(C)=NC=C2C1C1=CC=C(Cl)C=C1 QLMBAIRFQQLJJX-UHFFFAOYSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- OQEBBZSWEGYTPG-UHFFFAOYSA-N 3-aminobutanoic acid Chemical compound CC(N)CC(O)=O OQEBBZSWEGYTPG-UHFFFAOYSA-N 0.000 description 1
- GAGJMOQGABUOBK-UHFFFAOYSA-N 3-aminopropanamide;hydrochloride Chemical compound Cl.NCCC(N)=O GAGJMOQGABUOBK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- MEAPRSDUXBHXGD-UHFFFAOYSA-N 3-chloro-n-(4-propan-2-ylphenyl)propanamide Chemical compound CC(C)C1=CC=C(NC(=O)CCCl)C=C1 MEAPRSDUXBHXGD-UHFFFAOYSA-N 0.000 description 1
- 125000001137 3-hydroxypropoxy group Chemical group [H]OC([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- ZGRIPYHIFXGCHR-UHFFFAOYSA-N 3-o-[2-[(4-fluorophenyl)methyl-methylamino]ethyl] 5-o-propan-2-yl 4-(1,3-benzodioxol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C=1C=CC=2OCOC=2C=1C1C(C(=O)OC(C)C)=C(C)NC(C)=C1C(=O)OCCN(C)CC1=CC=C(F)C=C1 ZGRIPYHIFXGCHR-UHFFFAOYSA-N 0.000 description 1
- LINVVMHRTUSXHL-GGVPDPBRSA-N 3beta-hydroxy-5alpha-cholest-8(14)-en-15-one Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1C2=C2C(=O)C[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 LINVVMHRTUSXHL-GGVPDPBRSA-N 0.000 description 1
- GLQPTZAAUROJMO-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)benzaldehyde Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(C=O)C=C1 GLQPTZAAUROJMO-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- HPTISECXMUCRSR-UHFFFAOYSA-N 4-(3-phenylmethoxypropoxy)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1OCCCOCC1=CC=CC=C1 HPTISECXMUCRSR-UHFFFAOYSA-N 0.000 description 1
- OEBIVOHKFYSBPE-UHFFFAOYSA-N 4-Benzyloxybenzyl alcohol Chemical compound C1=CC(CO)=CC=C1OCC1=CC=CC=C1 OEBIVOHKFYSBPE-UHFFFAOYSA-N 0.000 description 1
- LUPJXXHWXBKHOO-DYVFJYSZSA-N 4-[(2r)-2-[[(2r)-2-hydroxy-2-phenylethyl]amino]propyl]benzoic acid Chemical compound C([C@@H](C)NC[C@H](O)C=1C=CC=CC=1)C1=CC=C(C(O)=O)C=C1 LUPJXXHWXBKHOO-DYVFJYSZSA-N 0.000 description 1
- LGSOKZOQANLOEU-UHFFFAOYSA-N 4-[2-(2,4-dioxo-1,3-thiazolidin-5-yl)ethoxy]benzonitrile Chemical compound S1C(=O)NC(=O)C1CCOC1=CC=C(C#N)C=C1 LGSOKZOQANLOEU-UHFFFAOYSA-N 0.000 description 1
- ZGLOYSNDXJVVCA-UHFFFAOYSA-N 4-[[2-methyl-4-(3-phenylmethoxypropoxy)phenyl]methyl]-5-propan-2-yl-1,2-dihydropyrazol-3-one Chemical compound N1NC(=O)C(CC=2C(=CC(OCCCOCC=3C=CC=CC=3)=CC=2)C)=C1C(C)C ZGLOYSNDXJVVCA-UHFFFAOYSA-N 0.000 description 1
- HUFUDYLPPPZLHM-UHFFFAOYSA-N 4-[[4-(2-phenylmethoxyethoxy)phenyl]methyl]-5-propan-2-yl-1,2-dihydropyrazol-3-one Chemical compound N1NC(=O)C(CC=2C=CC(OCCOCC=3C=CC=CC=3)=CC=2)=C1C(C)C HUFUDYLPPPZLHM-UHFFFAOYSA-N 0.000 description 1
- GPOQODYGMUTOQL-UHFFFAOYSA-N 4-bromo-3-methylphenol Chemical compound CC1=CC(O)=CC=C1Br GPOQODYGMUTOQL-UHFFFAOYSA-N 0.000 description 1
- ZQRVGYAMRJVUAK-UHFFFAOYSA-N 4-bromobutoxymethylbenzene Chemical compound BrCCCCOCC1=CC=CC=C1 ZQRVGYAMRJVUAK-UHFFFAOYSA-N 0.000 description 1
- MJRGSRRZKSJHOE-UHFFFAOYSA-N 5-(dimethylamino)-N-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulfonamide Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)NC=1ON=C(C)C=1C MJRGSRRZKSJHOE-UHFFFAOYSA-N 0.000 description 1
- NFFXEUUOMTXWCX-UHFFFAOYSA-N 5-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxy-n-[[4-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound C1=C(C(=O)NCC=2C=CC(=CC=2)C(F)(F)F)C(OC)=CC=C1CC1SC(=O)NC1=O NFFXEUUOMTXWCX-UHFFFAOYSA-N 0.000 description 1
- HGLFNRGXRCKGSW-UHFFFAOYSA-N 5-[(3,5-ditert-butyl-4-hydroxyanilino)-[[4-(2,2-dimethylpropyl)phenyl]methyl-hexylamino]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1NC(=C1C(OC(C)(C)OC1=O)=O)N(CCCCCC)CC1=CC=C(CC(C)(C)C)C=C1 HGLFNRGXRCKGSW-UHFFFAOYSA-N 0.000 description 1
- AZKFGOQRYCSQPK-UHFFFAOYSA-N 5-[(7-phenylmethoxyquinolin-3-yl)methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC1=CN=C(C=C(OCC=2C=CC=CC=2)C=C2)C2=C1 AZKFGOQRYCSQPK-UHFFFAOYSA-N 0.000 description 1
- MVDXXGIBARMXSA-PYUWXLGESA-N 5-[[(2r)-2-benzyl-3,4-dihydro-2h-chromen-6-yl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC1=CC=C(O[C@@H](CC=2C=CC=CC=2)CC2)C2=C1 MVDXXGIBARMXSA-PYUWXLGESA-N 0.000 description 1
- FQCUYGFIIAZMLU-UHFFFAOYSA-N 5-[[2-(naphthalen-2-ylmethyl)-1,3-benzoxazol-5-yl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC1=CC=C(OC(CC=2C=C3C=CC=CC3=CC=2)=N2)C2=C1 FQCUYGFIIAZMLU-UHFFFAOYSA-N 0.000 description 1
- PCAZCAZVHLGDBA-UHFFFAOYSA-N 5-[[4-(2-indol-1-ylethoxy)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC(C=C1)=CC=C1OCCN1C2=CC=CC=C2C=C1 PCAZCAZVHLGDBA-UHFFFAOYSA-N 0.000 description 1
- RWBBDSAYSNJJHM-UHFFFAOYSA-N 5-methyl-3-oxo-2-phenyl-1h-pyrazole-4-carbaldehyde Chemical compound O=C1C(C=O)=C(C)NN1C1=CC=CC=C1 RWBBDSAYSNJJHM-UHFFFAOYSA-N 0.000 description 1
- LWXHLNHAYCDUGT-UHFFFAOYSA-N 5-phenylmethoxy-1h-pyrazole Chemical class C=1C=CC=CC=1COC=1C=CNN=1 LWXHLNHAYCDUGT-UHFFFAOYSA-N 0.000 description 1
- SLXTWXQUEZSSTJ-UHFFFAOYSA-N 6-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopropyl]pyridine-3-carboxylic acid Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C1(C=2N=CC(=CC=2)C(O)=O)CC1 SLXTWXQUEZSSTJ-UHFFFAOYSA-N 0.000 description 1
- RBSGUQYXRDKPAE-QFIPXVFZSA-N 6-[4-[2-[[(2s)-3-(9h-carbazol-4-yloxy)-2-hydroxypropyl]amino]-2-methylpropyl]phenoxy]pyridine-3-carboxamide Chemical compound C([C@H](O)COC=1C=2C3=CC=CC=C3NC=2C=CC=1)NC(C)(C)CC(C=C1)=CC=C1OC1=CC=C(C(N)=O)C=N1 RBSGUQYXRDKPAE-QFIPXVFZSA-N 0.000 description 1
- DHSSDEDRBUKTQY-UHFFFAOYSA-N 6-prop-2-enyl-4,5,7,8-tetrahydrothiazolo[4,5-d]azepin-2-amine Chemical compound C1CN(CC=C)CCC2=C1N=C(N)S2 DHSSDEDRBUKTQY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 108010023016 A 71378 Proteins 0.000 description 1
- ITZMJCSORYKOSI-AJNGGQMLSA-N APGPR Enterostatin Chemical compound C[C@H](N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)N1[C@H](C(=O)N[C@@H](CCCN=C(N)N)C(O)=O)CCC1 ITZMJCSORYKOSI-AJNGGQMLSA-N 0.000 description 1
- DTDZLJHKVNTQGZ-GOSISDBHSA-N AZD7545 Chemical compound C1=CC(C(=O)N(C)C)=CC=C1S(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 DTDZLJHKVNTQGZ-GOSISDBHSA-N 0.000 description 1
- DJQOOSBJCLSSEY-UHFFFAOYSA-N Acipimox Chemical compound CC1=CN=C(C(O)=O)C=[N+]1[O-] DJQOOSBJCLSSEY-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
- 108010088751 Albumins Proteins 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- RDJQCOBTKKAQAH-FPOVZHCZSA-N Amibegron Chemical compound C1([C@@H](O)CN[C@H]2CCC3=CC=C(C=C3C2)OCC(=O)OCC)=CC=CC(Cl)=C1 RDJQCOBTKKAQAH-FPOVZHCZSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229940127438 Amylin Agonists Drugs 0.000 description 1
- 102000008873 Angiotensin II receptor Human genes 0.000 description 1
- 108050000824 Angiotensin II receptor Proteins 0.000 description 1
- 102000015427 Angiotensins Human genes 0.000 description 1
- 108010064733 Angiotensins Proteins 0.000 description 1
- NCUCGYYHUFIYNU-UHFFFAOYSA-N Aranidipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)=O)C1C1=CC=CC=C1[N+]([O-])=O NCUCGYYHUFIYNU-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
- 102100027936 Attractin Human genes 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- FBMCYYWIBYEOST-GJFSDDNBSA-N BIBO-3304 Chemical compound OC(=O)C(F)(F)F.N([C@H](CCCNC(=N)N)C(=O)NCC=1C=CC(CNC(N)=O)=CC=1)C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 FBMCYYWIBYEOST-GJFSDDNBSA-N 0.000 description 1
- 108010073982 BQ 610 Proteins 0.000 description 1
- XEMPUKIZUCIZEY-YSCHMLPRSA-N Barnidipine hydrochloride Chemical compound Cl.C1([C@@H]2C(=C(C)NC(C)=C2C(=O)OC)C(=O)O[C@@H]2CN(CC=3C=CC=CC=3)CC2)=CC=CC([N+]([O-])=O)=C1 XEMPUKIZUCIZEY-YSCHMLPRSA-N 0.000 description 1
- 108010081589 Becaplermin Proteins 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
- HWSISDHAHRVNMT-UHFFFAOYSA-N Bismuth subnitrate Chemical compound O[NH+]([O-])O[Bi](O[N+]([O-])=O)O[N+]([O-])=O HWSISDHAHRVNMT-UHFFFAOYSA-N 0.000 description 1
- 108010051479 Bombesin Proteins 0.000 description 1
- 102000013585 Bombesin Human genes 0.000 description 1
- 235000011960 Brassica ruvo Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000002083 C09CA01 - Losartan Substances 0.000 description 1
- 239000004072 C09CA03 - Valsartan Substances 0.000 description 1
- 239000002947 C09CA04 - Irbesartan Substances 0.000 description 1
- 239000005537 C09CA07 - Telmisartan Substances 0.000 description 1
- OBMZMSLWNNWEJA-XNCRXQDQSA-N C1=CC=2C(C[C@@H]3NC(=O)[C@@H](NC(=O)[C@H](NC(=O)N(CC#CCN(CCCC[C@H](NC(=O)[C@@H](CC4=CC=CC=C4)NC3=O)C(=O)N)CC=C)NC(=O)[C@@H](N)C)CC3=CNC4=C3C=CC=C4)C)=CNC=2C=C1 Chemical compound C1=CC=2C(C[C@@H]3NC(=O)[C@@H](NC(=O)[C@H](NC(=O)N(CC#CCN(CCCC[C@H](NC(=O)[C@@H](CC4=CC=CC=C4)NC3=O)C(=O)N)CC=C)NC(=O)[C@@H](N)C)CC3=CNC4=C3C=CC=C4)C)=CNC=2C=C1 OBMZMSLWNNWEJA-XNCRXQDQSA-N 0.000 description 1
- IOIFDQGQRNVROG-UHFFFAOYSA-N CCCCNC(=O)N=C Chemical compound CCCCNC(=O)N=C IOIFDQGQRNVROG-UHFFFAOYSA-N 0.000 description 1
- 108010055448 CJC 1131 Proteins 0.000 description 1
- PHKYGBHARUTZOY-UHFFFAOYSA-N CKD-711 Natural products OC1C(O)C(NC2C(C(O)C(O)C3(CO)OC32)O)C(CO)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O PHKYGBHARUTZOY-UHFFFAOYSA-N 0.000 description 1
- QLTVVOATEHFXLT-UHFFFAOYSA-N Cadralazine Chemical compound CCOC(=O)NNC1=CC=C(N(CC)CC(C)O)N=N1 QLTVVOATEHFXLT-UHFFFAOYSA-N 0.000 description 1
- 102000055006 Calcitonin Human genes 0.000 description 1
- 229940122820 Cannabinoid receptor antagonist Drugs 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 102000002666 Carnitine O-palmitoyltransferase Human genes 0.000 description 1
- 108010018424 Carnitine O-palmitoyltransferase Proteins 0.000 description 1
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 1
- 108010061846 Cholesterol Ester Transfer Proteins Proteins 0.000 description 1
- 102000012336 Cholesterol Ester Transfer Proteins Human genes 0.000 description 1
- 229920001268 Cholestyramine Polymers 0.000 description 1
- 108010005939 Ciliary Neurotrophic Factor Proteins 0.000 description 1
- 102100031614 Ciliary neurotrophic factor Human genes 0.000 description 1
- KPSRODZRAIWAKH-JTQLQIEISA-N Ciprofibrate Natural products C1=CC(OC(C)(C)C(O)=O)=CC=C1[C@H]1C(Cl)(Cl)C1 KPSRODZRAIWAKH-JTQLQIEISA-N 0.000 description 1
- BMOVQUBVGICXQN-UHFFFAOYSA-N Clinofibrate Chemical compound C1=CC(OC(C)(CC)C(O)=O)=CC=C1C1(C=2C=CC(OC(C)(CC)C(O)=O)=CC=2)CCCCC1 BMOVQUBVGICXQN-UHFFFAOYSA-N 0.000 description 1
- ZNIFSRGNXRYGHF-UHFFFAOYSA-N Clonidine hydrochloride Chemical compound Cl.ClC1=CC=CC(Cl)=C1NC1=NCCN1 ZNIFSRGNXRYGHF-UHFFFAOYSA-N 0.000 description 1
- 229920002905 Colesevelam Polymers 0.000 description 1
- 229920000230 Colestilan Polymers 0.000 description 1
- 208000032170 Congenital Abnormalities Diseases 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- YVIXXPCJZAUQHJ-YGRLFVJLSA-N Cp-114271 Chemical compound C([C@@H](C)NC[C@H](O)C=1N=C(SC=1)C(F)(F)F)C1=CC=C(OCC(O)=O)C=C1 YVIXXPCJZAUQHJ-YGRLFVJLSA-N 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- FDJCVHVKXFIEPJ-JCNFZFLDSA-N Delapril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N(CC(O)=O)C1CC2=CC=CC=C2C1)CC1=CC=CC=C1 FDJCVHVKXFIEPJ-JCNFZFLDSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 229940127422 Dipeptidase Inhibitors Drugs 0.000 description 1
- 102000003779 Dipeptidyl-peptidases and tripeptidyl-peptidases Human genes 0.000 description 1
- 108090000194 Dipeptidyl-peptidases and tripeptidyl-peptidases Proteins 0.000 description 1
- 108010061435 Enalapril Proteins 0.000 description 1
- 102000010180 Endothelin receptor Human genes 0.000 description 1
- 108050001739 Endothelin receptor Proteins 0.000 description 1
- 108010011459 Exenatide Proteins 0.000 description 1
- 241000282324 Felis Species 0.000 description 1
- LFMYNZPAVPMEGP-PIDGMYBPSA-N Fluvoxamine maleate Chemical compound OC(=O)\C=C/C(O)=O.COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 LFMYNZPAVPMEGP-PIDGMYBPSA-N 0.000 description 1
- 102000027487 Fructose-Bisphosphatase Human genes 0.000 description 1
- 108010017464 Fructose-Bisphosphatase Proteins 0.000 description 1
- QTQMRBZOBKYXCG-MHZLTWQESA-N GW 1929 Chemical compound N([C@@H](CC1=CC=C(C=C1)OCCN(C)C=1N=CC=CC=1)C(O)=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 QTQMRBZOBKYXCG-MHZLTWQESA-N 0.000 description 1
- GGUVRMBIEPYOKL-WMVCGJOFSA-N GW 409544 Chemical compound C([C@H](NC(/C)=C\C(=O)C=1C=CC=CC=1)C(O)=O)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 GGUVRMBIEPYOKL-WMVCGJOFSA-N 0.000 description 1
- 102400001370 Galanin Human genes 0.000 description 1
- 101800002068 Galanin Proteins 0.000 description 1
- HEMJJKBWTPKOJG-UHFFFAOYSA-N Gemfibrozil Chemical compound CC1=CC=C(C)C(OCCCC(C)(C)C(O)=O)=C1 HEMJJKBWTPKOJG-UHFFFAOYSA-N 0.000 description 1
- FAEKWTJYAYMJKF-QHCPKHFHSA-N GlucoNorm Chemical compound C1=C(C(O)=O)C(OCC)=CC(CC(=O)N[C@@H](CC(C)C)C=2C(=CC=CC=2)N2CCCCC2)=C1 FAEKWTJYAYMJKF-QHCPKHFHSA-N 0.000 description 1
- 102000030595 Glucokinase Human genes 0.000 description 1
- 108010021582 Glucokinase Proteins 0.000 description 1
- 102100022631 Glutamate receptor ionotropic, NMDA 2C Human genes 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- NMWQEPCLNXHPDX-UHFFFAOYSA-N Glybuzole Chemical compound S1C(C(C)(C)C)=NN=C1NS(=O)(=O)C1=CC=CC=C1 NMWQEPCLNXHPDX-UHFFFAOYSA-N 0.000 description 1
- 229920002527 Glycogen Polymers 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- MCSPBPXATWBACD-GAYQJXMFSA-N Guanabenz acetate Chemical compound CC(O)=O.NC(N)=N\N=C\C1=C(Cl)C=CC=C1Cl MCSPBPXATWBACD-GAYQJXMFSA-N 0.000 description 1
- DGFYECXYGUIODH-UHFFFAOYSA-N Guanfacine hydrochloride Chemical compound Cl.NC(N)=NC(=O)CC1=C(Cl)C=CC=C1Cl DGFYECXYGUIODH-UHFFFAOYSA-N 0.000 description 1
- LJIZUXQINHXGAO-ITWZMISCSA-N HR 780 Chemical compound C(\[C@H]1OC(=O)C[C@H](O)C1)=C/C=1C(C(C)C)=NC(C=2C=CC=CC=2)=CC=1C1=CC=C(F)C=C1 LJIZUXQINHXGAO-ITWZMISCSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101000697936 Homo sapiens Attractin Proteins 0.000 description 1
- 101000976075 Homo sapiens Insulin Proteins 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 102000003746 Insulin Receptor Human genes 0.000 description 1
- 108010001127 Insulin Receptor Proteins 0.000 description 1
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 108010018112 LY 315902 Proteins 0.000 description 1
- WTOVRSWDBLIFHU-UHFFFAOYSA-N Lemildipine Chemical compound COC(=O)C1=C(C)NC(COC(N)=O)=C(C(=O)OC(C)C)C1C1=CC=CC(Cl)=C1Cl WTOVRSWDBLIFHU-UHFFFAOYSA-N 0.000 description 1
- WMFYOYKPJLRMJI-UHFFFAOYSA-N Lercanidipine hydrochloride Chemical compound Cl.COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)(C)CN(C)CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 WMFYOYKPJLRMJI-UHFFFAOYSA-N 0.000 description 1
- 102000003960 Ligases Human genes 0.000 description 1
- 108090000364 Ligases Proteins 0.000 description 1
- 229940127470 Lipase Inhibitors Drugs 0.000 description 1
- 108010013563 Lipoprotein Lipase Proteins 0.000 description 1
- 102100022119 Lipoprotein lipase Human genes 0.000 description 1
- 108010007859 Lisinopril Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- ZPXSCAKFGYXMGA-UHFFFAOYSA-N Mazindol Chemical compound N12CCN=C2C2=CC=CC=C2C1(O)C1=CC=C(Cl)C=C1 ZPXSCAKFGYXMGA-UHFFFAOYSA-N 0.000 description 1
- 102400001132 Melanin-concentrating hormone Human genes 0.000 description 1
- 101800002739 Melanin-concentrating hormone Proteins 0.000 description 1
- 102100023726 Melanocortin receptor 3 Human genes 0.000 description 1
- 101710085774 Melanocortin receptor 3 Proteins 0.000 description 1
- 102100023724 Melanocortin receptor 4 Human genes 0.000 description 1
- 101710085775 Melanocortin receptor 4 Proteins 0.000 description 1
- 239000000637 Melanocyte-Stimulating Hormone Substances 0.000 description 1
- 101710151321 Melanostatin Proteins 0.000 description 1
- 229940127308 Microsomal Triglyceride Transfer Protein Inhibitors Drugs 0.000 description 1
- IBAQFPQHRJAVAV-ULAWRXDQSA-N Miglitol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO IBAQFPQHRJAVAV-ULAWRXDQSA-N 0.000 description 1
- JXRAXHBVZQZSIC-JKVLGAQCSA-N Moexipril hydrochloride Chemical compound Cl.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 JXRAXHBVZQZSIC-JKVLGAQCSA-N 0.000 description 1
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 1
- WPNJAUFVNXKLIM-UHFFFAOYSA-N Moxonidine Chemical compound COC1=NC(C)=NC(Cl)=C1NC1=NCCN1 WPNJAUFVNXKLIM-UHFFFAOYSA-N 0.000 description 1
- WGZDBVOTUVNQFP-UHFFFAOYSA-N N-(1-phthalazinylamino)carbamic acid ethyl ester Chemical compound C1=CC=C2C(NNC(=O)OCC)=NN=CC2=C1 WGZDBVOTUVNQFP-UHFFFAOYSA-N 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 102400000064 Neuropeptide Y Human genes 0.000 description 1
- 102000003797 Neuropeptides Human genes 0.000 description 1
- 108090000189 Neuropeptides Proteins 0.000 description 1
- 102400001103 Neurotensin Human genes 0.000 description 1
- 101800001814 Neurotensin Proteins 0.000 description 1
- KUEUWHJGRZKESU-UHFFFAOYSA-N Niceritrol Chemical compound C=1C=CN=CC=1C(=O)OCC(COC(=O)C=1C=NC=CC=1)(COC(=O)C=1C=NC=CC=1)COC(=O)C1=CC=CN=C1 KUEUWHJGRZKESU-UHFFFAOYSA-N 0.000 description 1
- VRAHPESAMYMDQI-UHFFFAOYSA-N Nicomol Chemical compound C1CCC(COC(=O)C=2C=NC=CC=2)(COC(=O)C=2C=NC=CC=2)C(O)C1(COC(=O)C=1C=NC=CC=1)COC(=O)C1=CC=CN=C1 VRAHPESAMYMDQI-UHFFFAOYSA-N 0.000 description 1
- FAIIFDPAEUKBEP-UHFFFAOYSA-N Nilvadipine Chemical compound COC(=O)C1=C(C#N)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 FAIIFDPAEUKBEP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 102000001490 Opioid Peptides Human genes 0.000 description 1
- 108010093625 Opioid Peptides Proteins 0.000 description 1
- 229940123730 Orexin receptor antagonist Drugs 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 101710176384 Peptide 1 Proteins 0.000 description 1
- 229940122985 Peptide agonist Drugs 0.000 description 1
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 1
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 1
- 102000003992 Peroxidases Human genes 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 102000009097 Phosphorylases Human genes 0.000 description 1
- 108010073135 Phosphorylases Proteins 0.000 description 1
- GHUUBYQTCDQWRA-UHFFFAOYSA-N Pioglitazone hydrochloride Chemical compound Cl.N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 GHUUBYQTCDQWRA-UHFFFAOYSA-N 0.000 description 1
- 229920000148 Polycarbophil calcium Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
- 102000003923 Protein Kinase C Human genes 0.000 description 1
- 108090000315 Protein Kinase C Proteins 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- 208000017442 Retinal disease Diseases 0.000 description 1
- 108010038912 Retinoid X Receptors Proteins 0.000 description 1
- 102000034527 Retinoid X Receptors Human genes 0.000 description 1
- 206010038923 Retinopathy Diseases 0.000 description 1
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
- AJLFOPYRIVGYMJ-UHFFFAOYSA-N SJ000287055 Natural products C12C(OC(=O)C(C)CC)CCC=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 AJLFOPYRIVGYMJ-UHFFFAOYSA-N 0.000 description 1
- 229940127505 Sodium Channel Antagonists Drugs 0.000 description 1
- 102100029795 Sodium-dependent glucose transporter 1 Human genes 0.000 description 1
- 101710181093 Sodium-dependent glucose transporter 1 Proteins 0.000 description 1
- 102100021988 Sodium/bile acid cotransporter Human genes 0.000 description 1
- 101710195873 Sodium/bile acid cotransporter Proteins 0.000 description 1
- 102000005157 Somatostatin Human genes 0.000 description 1
- 108010056088 Somatostatin Proteins 0.000 description 1
- 229940127504 Somatostatin Receptor Agonists Drugs 0.000 description 1
- ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000000219 Sympatholytic Substances 0.000 description 1
- NAVMQTYZDKMPEU-UHFFFAOYSA-N Targretin Chemical compound CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C(=C)C1=CC=C(C(O)=O)C=C1 NAVMQTYZDKMPEU-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- HTWFXPCUFWKXOP-UHFFFAOYSA-N Tertatalol Chemical compound C1CCSC2=C1C=CC=C2OCC(O)CNC(C)(C)C HTWFXPCUFWKXOP-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229940127535 Thyroid Hormone Receptor Agonists Drugs 0.000 description 1
- 102000011923 Thyrotropin Human genes 0.000 description 1
- 108010061174 Thyrotropin Proteins 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-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
- 108091023040 Transcription factor Proteins 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- GSNOZLZNQMLSKJ-UHFFFAOYSA-N Trapidil Chemical compound CCN(CC)C1=CC(C)=NC2=NC=NN12 GSNOZLZNQMLSKJ-UHFFFAOYSA-N 0.000 description 1
- FNYLWPVRPXGIIP-UHFFFAOYSA-N Triamterene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 description 1
- 102100040411 Tripeptidyl-peptidase 2 Human genes 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 102000005630 Urocortins Human genes 0.000 description 1
- 108010059705 Urocortins Proteins 0.000 description 1
- MVMIPBPFTZGTBS-UHFFFAOYSA-N Vatanidipine hydrochloride Chemical compound Cl.Cl.COC(=O)C1=C(C)NC(C)=C(C(=O)OCCC=2C=CC(=CC=2)N2CCN(CC2)C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 MVMIPBPFTZGTBS-UHFFFAOYSA-N 0.000 description 1
- 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 1
- FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 description 1
- NWLFOBZKYXKBOF-NSVAZKTRSA-N [(1s,2s)-2-[[2,2-dimethylpropyl(nonyl)carbamoyl]amino]cyclohexyl] 3-[[(4r)-2,2,5,5-tetramethyl-1,3-dioxane-4-carbonyl]amino]propanoate Chemical compound CCCCCCCCCN(CC(C)(C)C)C(=O)N[C@H]1CCCC[C@@H]1OC(=O)CCNC(=O)[C@H]1C(C)(C)COC(C)(C)O1 NWLFOBZKYXKBOF-NSVAZKTRSA-N 0.000 description 1
- JATPLOXBFFRHDN-DDWIOCJRSA-N [(2r)-2-acetyloxy-3-carboxypropyl]-trimethylazanium;chloride Chemical compound [Cl-].CC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C JATPLOXBFFRHDN-DDWIOCJRSA-N 0.000 description 1
- BXNCIERBDJYIQT-PRDVQWLOSA-N [(2r,3s,4s,5r,6s)-6-[2-[3-(1-benzofuran-5-yl)propanoyl]-3-hydroxy-5-methylphenoxy]-3,4,5-trihydroxyoxan-2-yl]methyl methyl carbonate Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(=O)OC)O[C@H]1OC1=CC(C)=CC(O)=C1C(=O)CCC1=CC=C(OC=C2)C2=C1 BXNCIERBDJYIQT-PRDVQWLOSA-N 0.000 description 1
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 1
- HIILOVHYWAEGDS-QBHOUYDASA-N [3-naphthalen-1-yl-1-[[(1s)-2-(4-phenylphenyl)-1-(2h-tetrazol-5-yl)ethyl]amino]propyl]phosphonic acid Chemical compound C([C@H](NC(CCC=1C2=CC=CC=C2C=CC=1)P(O)(=O)O)C1=NNN=N1)C(C=C1)=CC=C1C1=CC=CC=C1 HIILOVHYWAEGDS-QBHOUYDASA-N 0.000 description 1
- WUEHURHTEPWPPO-QZTJIDSGSA-N [4-[(4r,5r)-2-[[[2,6-di(propan-2-yl)phenyl]carbamoylamino]methyl]-4,5-dimethyl-1,3-dioxolan-2-yl]phenyl] dihydrogen phosphate Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NC(=O)NCC1(C=2C=CC(OP(O)(O)=O)=CC=2)O[C@H](C)[C@@H](C)O1 WUEHURHTEPWPPO-QZTJIDSGSA-N 0.000 description 1
- DOQPXTMNIUCOSY-UHFFFAOYSA-N [4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl]-[2-(3,4-dimethoxyphenyl)ethyl]-methylazanium;chloride Chemical compound [H+].[Cl-].C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 DOQPXTMNIUCOSY-UHFFFAOYSA-N 0.000 description 1
- 229960003830 acebutolol hydrochloride Drugs 0.000 description 1
- KTUFKADDDORSSI-UHFFFAOYSA-N acebutolol hydrochloride Chemical compound Cl.CCCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1 KTUFKADDDORSSI-UHFFFAOYSA-N 0.000 description 1
- BZKPWHYZMXOIDC-UHFFFAOYSA-N acetazolamide Chemical compound CC(=O)NC1=NN=C(S(N)(=O)=O)S1 BZKPWHYZMXOIDC-UHFFFAOYSA-N 0.000 description 1
- 229960000571 acetazolamide Drugs 0.000 description 1
- 229960001466 acetohexamide Drugs 0.000 description 1
- VGZSUPCWNCWDAN-UHFFFAOYSA-N acetohexamide Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 VGZSUPCWNCWDAN-UHFFFAOYSA-N 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 229960003526 acipimox Drugs 0.000 description 1
- 229950010285 acitemate Drugs 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 102000030621 adenylate cyclase Human genes 0.000 description 1
- 108060000200 adenylate cyclase Proteins 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- WSLOHMLGIVSUPR-UHFFFAOYSA-N adn-138 Chemical compound C1COC2=CC(Cl)=CC3=C2N1C(=O)C31CC(=O)NC1=O WSLOHMLGIVSUPR-UHFFFAOYSA-N 0.000 description 1
- 229950007884 alacepril Drugs 0.000 description 1
- MKOMESMZHZNBIZ-UHFFFAOYSA-M alagebrium Chemical compound [Cl-].CC1=C(C)SC=[N+]1CC(=O)C1=CC=CC=C1 MKOMESMZHZNBIZ-UHFFFAOYSA-M 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- OFCNXPDARWKPPY-UHFFFAOYSA-N allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 description 1
- 229960003459 allopurinol Drugs 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- PECIYKGSSMCNHN-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=NC=N[C]21.O=C1N(C)C(=O)N(C)C2=NC=N[C]21 PECIYKGSSMCNHN-UHFFFAOYSA-N 0.000 description 1
- 229960003556 aminophylline Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- LVEXHFZHOIWIIP-UHFFFAOYSA-N amosulalol Chemical compound COC1=CC=CC=C1OCCNCC(O)C1=CC=C(C)C(S(N)(=O)=O)=C1 LVEXHFZHOIWIIP-UHFFFAOYSA-N 0.000 description 1
- 229950010351 amosulalol Drugs 0.000 description 1
- 239000003392 amylase inhibitor Substances 0.000 description 1
- 230000006538 anaerobic glycolysis Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 229940125708 antidiabetic agent Drugs 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 229950007556 aranidipine Drugs 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000003289 ascorbyl group Chemical group [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 229960002274 atenolol Drugs 0.000 description 1
- 229960005370 atorvastatin Drugs 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- 125000005604 azodicarboxylate group Chemical group 0.000 description 1
- 229950009252 beclobrate Drugs 0.000 description 1
- YWQGBCXVCXMSLJ-UHFFFAOYSA-N beclobrate Chemical compound C1=CC(OC(C)(CC)C(=O)OCC)=CC=C1CC1=CC=C(Cl)C=C1 YWQGBCXVCXMSLJ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229960004916 benidipine Drugs 0.000 description 1
- QZVNQOLPLYWLHQ-ZEQKJWHPSA-N benidipine Chemical compound C1([C@H]2C(=C(C)NC(C)=C2C(=O)OC)C(=O)O[C@H]2CN(CC=3C=CC=CC=3)CCC2)=CC=CC([N+]([O-])=O)=C1 QZVNQOLPLYWLHQ-ZEQKJWHPSA-N 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- WHQCHUCQKNIQEC-UHFFFAOYSA-N benzbromarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(Br)=C(O)C(Br)=C1 WHQCHUCQKNIQEC-UHFFFAOYSA-N 0.000 description 1
- 229960002529 benzbromarone Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 229950003745 benzfetamine Drugs 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- YXKTVDFXDRQTKV-HNNXBMFYSA-N benzphetamine Chemical compound C([C@H](C)N(C)CC=1C=CC=CC=1)C1=CC=CC=C1 YXKTVDFXDRQTKV-HNNXBMFYSA-N 0.000 description 1
- KKBIUAUSZKGNOA-HNAYVOBHSA-N benzyl (2s)-2-[[(2s)-2-(acetylsulfanylmethyl)-3-(1,3-benzodioxol-5-yl)propanoyl]amino]propanoate Chemical compound O=C([C@@H](NC(=O)[C@@H](CSC(C)=O)CC=1C=C2OCOC2=CC=1)C)OCC1=CC=CC=C1 KKBIUAUSZKGNOA-HNAYVOBHSA-N 0.000 description 1
- IUGQFMIATSVYLK-UHFFFAOYSA-N benzyl 2-(4-hydroxyphenyl)acetate Chemical compound C1=CC(O)=CC=C1CC(=O)OCC1=CC=CC=C1 IUGQFMIATSVYLK-UHFFFAOYSA-N 0.000 description 1
- PIIYOXFGVHEMGI-UHFFFAOYSA-N benzyl n-(1-amino-2-methyl-1-oxopropan-2-yl)carbamate Chemical compound NC(=O)C(C)(C)NC(=O)OCC1=CC=CC=C1 PIIYOXFGVHEMGI-UHFFFAOYSA-N 0.000 description 1
- 229950007003 benzylhydrochlorothiazide Drugs 0.000 description 1
- 229960002890 beraprost Drugs 0.000 description 1
- CTPOHARTNNSRSR-APJZLKAGSA-N beraprost Chemical compound O([C@H]1C[C@@H](O)[C@@H]([C@@H]21)/C=C/[C@@H](O)C(C)CC#CC)C1=C2C=CC=C1CCCC(O)=O CTPOHARTNNSRSR-APJZLKAGSA-N 0.000 description 1
- 229950005357 bervastatin Drugs 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 229960003588 bevantolol Drugs 0.000 description 1
- HXLAFSUPPDYFEO-UHFFFAOYSA-N bevantolol Chemical compound C1=C(OC)C(OC)=CC=C1CCNCC(O)COC1=CC=CC(C)=C1 HXLAFSUPPDYFEO-UHFFFAOYSA-N 0.000 description 1
- 229960002938 bexarotene Drugs 0.000 description 1
- 229960000516 bezafibrate Drugs 0.000 description 1
- IIBYAHWJQTYFKB-UHFFFAOYSA-N bezafibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 IIBYAHWJQTYFKB-UHFFFAOYSA-N 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 229940096699 bile acid sequestrants Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229950004495 binifibrate Drugs 0.000 description 1
- BFYRHDVAEJIBON-UHFFFAOYSA-N binifibrate Chemical compound C=1C=CN=CC=1C(=O)OCC(COC(=O)C=1C=NC=CC=1)OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 BFYRHDVAEJIBON-UHFFFAOYSA-N 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- RSMSFENOAKAUJU-UHFFFAOYSA-L bis[[2-(4-chlorophenoxy)-2-methylpropanoyl]oxy]aluminum;hydrate Chemical compound O.C=1C=C(Cl)C=CC=1OC(C)(C)C(=O)O[Al]OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 RSMSFENOAKAUJU-UHFFFAOYSA-L 0.000 description 1
- 229960001482 bismuth subnitrate Drugs 0.000 description 1
- 229960002781 bisoprolol Drugs 0.000 description 1
- VHYCDWMUTMEGQY-UHFFFAOYSA-N bisoprolol Chemical compound CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1 VHYCDWMUTMEGQY-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- DNDCVAGJPBKION-DOPDSADYSA-N bombesin Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC=1NC2=CC=CC=C2C=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1NC(=O)CC1)C(C)C)C1=CN=CN1 DNDCVAGJPBKION-DOPDSADYSA-N 0.000 description 1
- 229960001035 bopindolol Drugs 0.000 description 1
- 229960003065 bosentan Drugs 0.000 description 1
- SXTRWVVIEPWAKM-UHFFFAOYSA-N bosentan hydrate Chemical compound O.COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=CC=CN=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 SXTRWVVIEPWAKM-UHFFFAOYSA-N 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 229960002802 bromocriptine Drugs 0.000 description 1
- NOJMTMIRQRDZMT-GSPXQYRGSA-N bromocriptine methanesulfonate Chemical compound CS(O)(=O)=O.C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 NOJMTMIRQRDZMT-GSPXQYRGSA-N 0.000 description 1
- DQGFCLJXYFXXIJ-LFIBNONCSA-N budralazine Chemical compound C1=CC=C2C(N/N=C(C)/C=C(C)C)=NN=CC2=C1 DQGFCLJXYFXXIJ-LFIBNONCSA-N 0.000 description 1
- 229950001730 budralazine Drugs 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229960004111 buformin Drugs 0.000 description 1
- XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 description 1
- 229960003612 bunazosin hydrochloride Drugs 0.000 description 1
- SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 description 1
- 229960001058 bupropion Drugs 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960005211 cadralazine Drugs 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229960004015 calcitonin Drugs 0.000 description 1
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 229940095498 calcium polycarbophil Drugs 0.000 description 1
- MWKXCSMICWVRGW-UHFFFAOYSA-N calcium;phosphane Chemical compound P.[Ca] MWKXCSMICWVRGW-UHFFFAOYSA-N 0.000 description 1
- 235000019577 caloric intake Nutrition 0.000 description 1
- 229950001261 camiglibose Drugs 0.000 description 1
- 239000003537 cannabinoid receptor agonist Substances 0.000 description 1
- 229940121376 cannabinoid receptor agonist Drugs 0.000 description 1
- 239000003536 cannabinoid receptor antagonist Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229960000830 captopril Drugs 0.000 description 1
- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- VDTNNGKXZGSZIP-UHFFFAOYSA-N carbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VDTNNGKXZGSZIP-UHFFFAOYSA-N 0.000 description 1
- 229960003362 carbutamide Drugs 0.000 description 1
- FYBXRCFPOTXTJF-UHFFFAOYSA-N carteolol hydrochloride Chemical compound [Cl-].N1C(=O)CCC2=C1C=CC=C2OCC(O)C[NH2+]C(C)(C)C FYBXRCFPOTXTJF-UHFFFAOYSA-N 0.000 description 1
- 229960002165 carteolol hydrochloride Drugs 0.000 description 1
- 229960004195 carvedilol Drugs 0.000 description 1
- NPAKNKYSJIDKMW-UHFFFAOYSA-N carvedilol Chemical compound COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=NC3=CC=C[CH]C3=C12 NPAKNKYSJIDKMW-UHFFFAOYSA-N 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000005779 cell damage Effects 0.000 description 1
- 229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 description 1
- SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 description 1
- 229960005110 cerivastatin Drugs 0.000 description 1
- 229950005749 ceronapril Drugs 0.000 description 1
- MVCQKIKWYUURMU-UHFFFAOYSA-N cetilistat Chemical compound C1=C(C)C=C2C(=O)OC(OCCCCCCCCCCCCCCCC)=NC2=C1 MVCQKIKWYUURMU-UHFFFAOYSA-N 0.000 description 1
- 229950002397 cetilistat Drugs 0.000 description 1
- JUFFVKRROAPVBI-PVOYSMBESA-N chembl1210015 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(=O)N[C@H]1[C@@H]([C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO[C@]3(O[C@@H](C[C@H](O)[C@H](O)CO)[C@H](NC(C)=O)[C@@H](O)C3)C(O)=O)O2)O)[C@@H](CO)O1)NC(C)=O)C(=O)NCC(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 JUFFVKRROAPVBI-PVOYSMBESA-N 0.000 description 1
- ZWGWSFHAZWNQQE-VPLSKCCHSA-N chembl1836102 Chemical compound Cl.C1=CC=C2C(N)=NC(NC[C@@H]3CC[C@@H](CNS(=O)(=O)C=4C=C5C=CC=CC5=CC=4)CC3)=NC2=C1 ZWGWSFHAZWNQQE-VPLSKCCHSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229960001761 chlorpropamide Drugs 0.000 description 1
- 229960001523 chlortalidone Drugs 0.000 description 1
- 230000001906 cholesterol absorption Effects 0.000 description 1
- YZFWTZACSRHJQD-UHFFFAOYSA-N ciglitazone Chemical compound C=1C=C(CC2C(NC(=O)S2)=O)C=CC=1OCC1(C)CCCCC1 YZFWTZACSRHJQD-UHFFFAOYSA-N 0.000 description 1
- 229950009226 ciglitazone Drugs 0.000 description 1
- 229960005025 cilazapril Drugs 0.000 description 1
- JQRZBPFGBRIWSN-YOTVLOEGSA-N cilazapril monohydrate Chemical compound O.C([C@@H](C(=O)OCC)N[C@@H]1C(N2[C@@H](CCCN2CCC1)C(O)=O)=O)CC1=CC=CC=C1 JQRZBPFGBRIWSN-YOTVLOEGSA-N 0.000 description 1
- RRGUKTPIGVIEKM-UHFFFAOYSA-N cilostazol Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCC1=NN=NN1C1CCCCC1 RRGUKTPIGVIEKM-UHFFFAOYSA-N 0.000 description 1
- 229960004588 cilostazol Drugs 0.000 description 1
- 229960002174 ciprofibrate Drugs 0.000 description 1
- KPSRODZRAIWAKH-UHFFFAOYSA-N ciprofibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C1C(Cl)(Cl)C1 KPSRODZRAIWAKH-UHFFFAOYSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- PHKYGBHARUTZOY-KTVVNDHVSA-N ckd-711 Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@]2(CO)O[C@@H]21)O)CO)[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O PHKYGBHARUTZOY-KTVVNDHVSA-N 0.000 description 1
- 229950003072 clinofibrate Drugs 0.000 description 1
- 229960001214 clofibrate Drugs 0.000 description 1
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
- 229950008441 clofibric acid Drugs 0.000 description 1
- TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 description 1
- 229960002925 clonidine hydrochloride Drugs 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 229960000674 colesevelam hydrochloride Drugs 0.000 description 1
- 229960004095 colestilan Drugs 0.000 description 1
- 229950010523 colestolone Drugs 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- JGBBVDFNZSRLIF-UHFFFAOYSA-N conivaptan Chemical compound C12=CC=CC=C2C=2[N]C(C)=NC=2CCN1C(=O)C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=CC=C1 JGBBVDFNZSRLIF-UHFFFAOYSA-N 0.000 description 1
- 229960000562 conivaptan Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229950002753 crilvastatin Drugs 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- DZFSTAUMUPHORN-NRFANRHFSA-N cyclohexyl-[[4-[2-[[(2s)-2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]phenoxy]methyl]phosphinic acid Chemical compound C([C@H](O)COC=1C=CC(O)=CC=1)NCCC(C=C1)=CC=C1OCP(O)(=O)C1CCCCC1 DZFSTAUMUPHORN-NRFANRHFSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229950003040 dalvastatin Drugs 0.000 description 1
- FEJVSJIALLTFRP-LJQANCHMSA-N darusentan Chemical compound COC1=CC(OC)=NC(O[C@H](C(O)=O)C(OC)(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 FEJVSJIALLTFRP-LJQANCHMSA-N 0.000 description 1
- 229950008833 darusentan Drugs 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229960000632 dexamfetamine Drugs 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229960001079 dilazep Drugs 0.000 description 1
- VILIWRRWAWKXRW-UHFFFAOYSA-N dilazep dihydrochloride Chemical compound [Cl-].[Cl-].COC1=C(OC)C(OC)=CC(C(=O)OCCC[NH+]2CC[NH+](CCCOC(=O)C=3C=C(OC)C(OC)=C(OC)C=3)CCC2)=C1 VILIWRRWAWKXRW-UHFFFAOYSA-N 0.000 description 1
- 229960005316 diltiazem hydrochloride Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 1
- 229960002768 dipyridamole Drugs 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- FXHKSTYWSZZOBF-NTEVMMBTSA-L disodium;(3s)-4-[2-[1-(4-fluorophenyl)-3-propan-2-ylindol-2-yl]ethynyl-oxidophosphoryl]-3-hydroxybutanoate Chemical compound [Na+].[Na+].C12=CC=CC=C2C(C(C)C)=C(C#CP([O-])(=O)C[C@@H](O)CC([O-])=O)N1C1=CC=C(F)C=C1 FXHKSTYWSZZOBF-NTEVMMBTSA-L 0.000 description 1
- FUZBPOHHSBDTJQ-CFOQQKEYSA-L disodium;5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound [Na+].[Na+].C1([C@@H](O)CN[C@@H](CC=2C=C3OC(OC3=CC=2)(C([O-])=O)C([O-])=O)C)=CC=CC(Cl)=C1 FUZBPOHHSBDTJQ-CFOQQKEYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 1
- VJECBOKJABCYMF-UHFFFAOYSA-N doxazosin mesylate Chemical compound [H+].CS([O-])(=O)=O.C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 VJECBOKJABCYMF-UHFFFAOYSA-N 0.000 description 1
- 229960000220 doxazosin mesylate Drugs 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- ODUOJXZPIYUATO-LJQANCHMSA-N ecadotril Chemical compound C([C@H](CSC(=O)C)C(=O)NCC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 ODUOJXZPIYUATO-LJQANCHMSA-N 0.000 description 1
- 229950001184 ecadotril Drugs 0.000 description 1
- 229950003102 efonidipine Drugs 0.000 description 1
- 229950007075 eldacimibe Drugs 0.000 description 1
- 229950010020 elgodipine Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- OYFJQPXVCSSHAI-QFPUQLAESA-N enalapril maleate Chemical compound OC(=O)\C=C/C(O)=O.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 OYFJQPXVCSSHAI-QFPUQLAESA-N 0.000 description 1
- 229960000309 enalapril maleate Drugs 0.000 description 1
- 229950002375 englitazone Drugs 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000006862 enzymatic digestion Effects 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 229940125532 enzyme inhibitor Drugs 0.000 description 1
- CHNUOJQWGUIOLD-NFZZJPOKSA-N epalrestat Chemical compound C=1C=CC=CC=1\C=C(/C)\C=C1/SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-NFZZJPOKSA-N 0.000 description 1
- 229950010170 epalrestat Drugs 0.000 description 1
- CHNUOJQWGUIOLD-UHFFFAOYSA-N epalrestate Natural products C=1C=CC=CC=1C=C(C)C=C1SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-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
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- SSQPWTVBQMWLSZ-AAQCHOMXSA-N ethyl (5Z,8Z,11Z,14Z,17Z)-icosapentaenoate Chemical compound CCOC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC SSQPWTVBQMWLSZ-AAQCHOMXSA-N 0.000 description 1
- ZADJRRFMOOACHL-WQICJITCSA-N ethyl (e,3s,5r)-7-[4-(4-fluorophenyl)spiro[chromene-2,1'-cyclopentane]-3-yl]-3,5-dihydroxyhept-6-enoate Chemical compound C12=CC=CC=C2OC2(CCCC2)C(/C=C/[C@H](O)C[C@H](O)CC(=O)OCC)=C1C1=CC=C(F)C=C1 ZADJRRFMOOACHL-WQICJITCSA-N 0.000 description 1
- PWRYMMTWSPKRJD-NSLUPJTDSA-N ethyl 3-[(7r)-7-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-5,6,7,8-tetrahydronaphthalen-2-yl]propanoate;hydrochloride Chemical compound Cl.C1([C@@H](O)CN[C@@H]2CCC3=CC=C(C=C3C2)CCC(=O)OCC)=CC=CC(Cl)=C1 PWRYMMTWSPKRJD-NSLUPJTDSA-N 0.000 description 1
- NWWORXYTJRPSMC-QKPAOTATSA-N ethyl 4-[2-[(2r,3r,4r,5s)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]ethoxy]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1OCCN1[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C1 NWWORXYTJRPSMC-QKPAOTATSA-N 0.000 description 1
- XCLDSQRVMMXWMS-UHFFFAOYSA-N ethyl 4-methyl-3-oxopentanoate Chemical compound CCOC(=O)CC(=O)C(C)C XCLDSQRVMMXWMS-UHFFFAOYSA-N 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 229960003501 etofibrate Drugs 0.000 description 1
- XXRVYAFBUDSLJX-UHFFFAOYSA-N etofibrate Chemical compound C=1C=CN=CC=1C(=O)OCCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 XXRVYAFBUDSLJX-UHFFFAOYSA-N 0.000 description 1
- 229960001519 exenatide Drugs 0.000 description 1
- 238000009207 exercise therapy Methods 0.000 description 1
- OLNTVTPDXPETLC-XPWALMASSA-N ezetimibe Chemical compound N1([C@@H]([C@H](C1=O)CC[C@H](O)C=1C=CC(F)=CC=1)C=1C=CC(O)=CC=1)C1=CC=C(F)C=C1 OLNTVTPDXPETLC-XPWALMASSA-N 0.000 description 1
- 229960000815 ezetimibe Drugs 0.000 description 1
- ZZCHHVUQYRMYLW-HKBQPEDESA-N farglitazar Chemical compound N([C@@H](CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 ZZCHHVUQYRMYLW-HKBQPEDESA-N 0.000 description 1
- 229950005203 fasidotril Drugs 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229960001582 fenfluramine Drugs 0.000 description 1
- 229960002297 fenofibrate Drugs 0.000 description 1
- YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 description 1
- WAAPEIZFCHNLKK-PELKAZGASA-N fidarestat Chemical compound C([C@@H](OC1=CC=C(F)C=C11)C(=O)N)[C@@]21NC(=O)NC2=O WAAPEIZFCHNLKK-PELKAZGASA-N 0.000 description 1
- 229950007256 fidarestat Drugs 0.000 description 1
- 229960003765 fluvastatin Drugs 0.000 description 1
- 229960002107 fluvoxamine maleate Drugs 0.000 description 1
- 229940013688 formic acid Drugs 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 229960002737 fructose Drugs 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229960003883 furosemide Drugs 0.000 description 1
- AIWAEWBZDJARBJ-PXUUZXDZSA-N fz7co35x2s Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCCCNC(=O)COCCOCCNC(=O)CCN1C(C=CC1=O)=O)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 AIWAEWBZDJARBJ-PXUUZXDZSA-N 0.000 description 1
- 229960003627 gemfibrozil Drugs 0.000 description 1
- 229950000806 glenvastatin Drugs 0.000 description 1
- 229960001764 glibornuride Drugs 0.000 description 1
- RMTYNAPTNBJHQI-LLDVTBCESA-N glibornuride Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N[C@H]1[C@H](C2(C)C)CC[C@@]2(C)[C@H]1O RMTYNAPTNBJHQI-LLDVTBCESA-N 0.000 description 1
- 229960004346 glimepiride Drugs 0.000 description 1
- WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 description 1
- JRJLFQURIXLQJD-YCLXMMFGSA-N glucobrassicin Natural products OC[C@@H]1O[C@H](SC(=NOS(=O)(=O)O)[C@H](O)[C@H](O)Cc2c[nH]c3ccccc23)[C@@H](O)[C@H](O)[C@H]1O JRJLFQURIXLQJD-YCLXMMFGSA-N 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 1
- DVQVBLBKEXITIK-UHFFFAOYSA-N glybuthiazol Chemical compound S1C(C(C)(C)C)=NN=C1NS(=O)(=O)C1=CC=C(N)C=C1 DVQVBLBKEXITIK-UHFFFAOYSA-N 0.000 description 1
- 230000036252 glycation Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 229940096919 glycogen Drugs 0.000 description 1
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229960003050 guanabenz acetate Drugs 0.000 description 1
- 229960004746 guanfacine hydrochloride Drugs 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004871 hexylcarbonyl group Chemical group C(CCCCC)C(=O)* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229960002885 histidine Drugs 0.000 description 1
- 239000003667 hormone antagonist Substances 0.000 description 1
- ZUXNZUWOTSUBMN-UHFFFAOYSA-N hydralazine hydrochloride Chemical compound Cl.C1=CC=C2C(NN)=NN=CC2=C1 ZUXNZUWOTSUBMN-UHFFFAOYSA-N 0.000 description 1
- 229960005384 hydralazine hydrochloride Drugs 0.000 description 1
- 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 1
- 229960003313 hydroflumethiazide Drugs 0.000 description 1
- TWTMQRXNAZGSCE-UHFFFAOYSA-N hydron;[6-(methylamino)-1-(2-methylpropanoyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl] 2-methylpropanoate;chloride Chemical compound Cl.C1=CC(OC(=O)C(C)C)=C(OC(=O)C(C)C)C2=C1CC(NC)CC2 TWTMQRXNAZGSCE-UHFFFAOYSA-N 0.000 description 1
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 1
- 229960002600 icosapent ethyl 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
- 229960003409 imidapril hydrochloride Drugs 0.000 description 1
- 229950007327 imirestat Drugs 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PBGKTOXHQIOBKM-FHFVDXKLSA-N insulin (human) Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3NC=NC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 PBGKTOXHQIOBKM-FHFVDXKLSA-N 0.000 description 1
- 230000007154 intracellular accumulation Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229960002198 irbesartan Drugs 0.000 description 1
- 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 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- 125000005932 isopentyloxycarbonyl group Chemical group 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 229960002479 isosorbide Drugs 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 229960004427 isradipine Drugs 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 229960004340 lacidipine Drugs 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229950005959 lecimibide Drugs 0.000 description 1
- 229950001530 lemildipine Drugs 0.000 description 1
- 102000005861 leptin receptors Human genes 0.000 description 1
- 108010019813 leptin receptors Proteins 0.000 description 1
- 229960002162 lercanidipine hydrochloride Drugs 0.000 description 1
- 229960001518 levocarnitine Drugs 0.000 description 1
- YDTFRJLNMPSCFM-YDALLXLXSA-M levothyroxine sodium anhydrous Chemical compound [Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 YDTFRJLNMPSCFM-YDALLXLXSA-M 0.000 description 1
- SBXXSUDPJJJJLC-YDALLXLXSA-M liothyronine sodium Chemical compound [Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 SBXXSUDPJJJJLC-YDALLXLXSA-M 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229960002394 lisinopril Drugs 0.000 description 1
- 150000002641 lithium Chemical group 0.000 description 1
- KSMAGQUYOIHWFS-UHFFFAOYSA-N lofexidine Chemical compound N=1CCNC=1C(C)OC1=C(Cl)C=CC=C1Cl KSMAGQUYOIHWFS-UHFFFAOYSA-N 0.000 description 1
- 229960005209 lofexidine Drugs 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- ZEUXAIYYDDCIRX-UHFFFAOYSA-N losartan carboxylic acid Chemical compound CCCCC1=NC(Cl)=C(C(O)=O)N1CC1=CC=C(C=2C(=CC=CC=2)C2=NNN=N2)C=C1 ZEUXAIYYDDCIRX-UHFFFAOYSA-N 0.000 description 1
- 229960000519 losartan potassium Drugs 0.000 description 1
- 229960004844 lovastatin Drugs 0.000 description 1
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960003963 manidipine Drugs 0.000 description 1
- ANEBWFXPVPTEET-UHFFFAOYSA-N manidipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN2CCN(CC2)C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ANEBWFXPVPTEET-UHFFFAOYSA-N 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- ORRDHOMWDPJSNL-UHFFFAOYSA-N melanin concentrating hormone Chemical compound N1C(=O)C(C(C)C)NC(=O)C(CCCNC(N)=N)NC(=O)CNC(=O)C(C(C)C)NC(=O)C(CCSC)NC(=O)C(NC(=O)C(CCCNC(N)=N)NC(=O)C(NC(=O)C(NC(=O)C(N)CC(O)=O)C(C)O)CCSC)CSSCC(C(=O)NC(CC=2C3=CC=CC=C3NC=2)C(=O)NC(CCC(O)=O)C(=O)NC(C(C)C)C(O)=O)NC(=O)C2CCCN2C(=O)C(CCCNC(N)=N)NC(=O)C1CC1=CC=C(O)C=C1 ORRDHOMWDPJSNL-UHFFFAOYSA-N 0.000 description 1
- 239000000336 melanocortin receptor agonist Substances 0.000 description 1
- 229960004329 metformin hydrochloride Drugs 0.000 description 1
- OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin hydrochloride Natural products CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 229960001252 methamphetamine Drugs 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 229940098779 methanesulfonic acid 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
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- IVAQJHSXBVHUQT-ZVHZXABRSA-N methyl (e)-3-(3,5-dimethoxyphenyl)-2-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]phenyl]prop-2-enoate Chemical compound C=1C=C(OC=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)C=CC=1/C(C(=O)OC)=C\C1=CC(OC)=CC(OC)=C1 IVAQJHSXBVHUQT-ZVHZXABRSA-N 0.000 description 1
- ZFLBZHXQAMUEFS-KUHUBIRLSA-N methyl 2-[4-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]phenoxy]acetate Chemical compound C1=CC(OCC(=O)OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=CC(Cl)=C1 ZFLBZHXQAMUEFS-KUHUBIRLSA-N 0.000 description 1
- MVQOMOXWRUVMOG-UHFFFAOYSA-N methyl 2-[4-[2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]acetate;hydrochloride Chemical compound Cl.C1=CC(OCC(=O)OC)=CC=C1OCCNCC(O)COC1=CC=CC=C1 MVQOMOXWRUVMOG-UHFFFAOYSA-N 0.000 description 1
- VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 description 1
- OIZISCUUSLPUEN-LMORPYAASA-N methyl 4-[(2s)-2-[[(2s)-2-hydroxy-2-phenylethyl]amino]propyl]benzoate;(e)-4-oxopent-2-enoic acid Chemical compound CC(=O)\C=C\C(O)=O.C1=CC(C(=O)OC)=CC=C1C[C@H](C)NC[C@@H](O)C1=CC=CC=C1 OIZISCUUSLPUEN-LMORPYAASA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 229960001300 metoprolol tartrate Drugs 0.000 description 1
- AJLFOPYRIVGYMJ-INTXDZFKSA-N mevastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=CCC[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 AJLFOPYRIVGYMJ-INTXDZFKSA-N 0.000 description 1
- 229950009116 mevastatin Drugs 0.000 description 1
- BOZILQFLQYBIIY-UHFFFAOYSA-N mevastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CCC=C21 BOZILQFLQYBIIY-UHFFFAOYSA-N 0.000 description 1
- VLPIATFUUWWMKC-UHFFFAOYSA-N mexiletine Chemical compound CC(N)COC1=C(C)C=CC=C1C VLPIATFUUWWMKC-UHFFFAOYSA-N 0.000 description 1
- 229960001070 mexiletine hydrochloride Drugs 0.000 description 1
- BMGQWWVMWDBQGC-IIFHNQTCSA-N midostaurin Chemical compound CN([C@H]1[C@H]([C@]2(C)O[C@@H](N3C4=CC=CC=C4C4=C5C(=O)NCC5=C5C6=CC=CC=C6N2C5=C43)C1)OC)C(=O)C1=CC=CC=C1 BMGQWWVMWDBQGC-IIFHNQTCSA-N 0.000 description 1
- 229950010895 midostaurin Drugs 0.000 description 1
- 229960001110 miglitol Drugs 0.000 description 1
- 229950002259 minalrestat Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229960003365 mitiglinide Drugs 0.000 description 1
- WPGGHFDDFPHPOB-BBWFWOEESA-N mitiglinide Chemical compound C([C@@H](CC(=O)N1C[C@@H]2CCCC[C@@H]2C1)C(=O)O)C1=CC=CC=C1 WPGGHFDDFPHPOB-BBWFWOEESA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229960004185 moexipril hydrochloride Drugs 0.000 description 1
- SLZIZIJTGAYEKK-CIJSCKBQSA-N molport-023-220-247 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)CN)[C@@H](C)O)C1=CNC=N1 SLZIZIJTGAYEKK-CIJSCKBQSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 229950006549 moveltipril Drugs 0.000 description 1
- 229960003938 moxonidine Drugs 0.000 description 1
- 229950000546 mozavaptan Drugs 0.000 description 1
- 230000003232 mucoadhesive effect Effects 0.000 description 1
- CVABPTLRAQIZJU-UHFFFAOYSA-N n'-[3-(2,6-dichloro-4-methoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl]-n-(oxan-4-yl)ethane-1,2-diamine Chemical compound ClC1=CC(OC)=CC(Cl)=C1C1=C2N=C(C)C=C(NCCNC3CCOCC3)N2N=C1C CVABPTLRAQIZJU-UHFFFAOYSA-N 0.000 description 1
- YFJUSGDKCDQMNE-UHFFFAOYSA-N n-(2-acetyl-4,6-dimethylphenyl)-3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]thiophene-2-carboxamide Chemical compound CC(=O)C1=CC(C)=CC(C)=C1NC(=O)C1=C(S(=O)(=O)NC2=C(C(C)=NO2)Cl)C=CS1 YFJUSGDKCDQMNE-UHFFFAOYSA-N 0.000 description 1
- LJGUZUROJOJEMI-UHFFFAOYSA-N n-(3,4-dimethyl-1,2-oxazol-5-yl)-2-[4-(1,3-oxazol-2-yl)phenyl]benzenesulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C(=CC=CC=2)C=2C=CC(=CC=2)C=2OC=CN=2)=C1C LJGUZUROJOJEMI-UHFFFAOYSA-N 0.000 description 1
- CMCWIHQJEQYHPX-UHFFFAOYSA-N n-[2-[(2-aminohydrazinyl)methylideneamino]ethyl]acetamide;hydrochloride Chemical compound Cl.CC(=O)NCCN=CNNN CMCWIHQJEQYHPX-UHFFFAOYSA-N 0.000 description 1
- DSEGFUSAJVUFLK-OFNKIYASSA-N n-[5-[(1r)-2-[[(1r)-2-(3-chlorophenyl)-1-[4-(difluoromethoxy)phenyl]ethyl]amino]-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC([C@@H](O)CN[C@H](CC=2C=C(Cl)C=CC=2)C=2C=CC(OC(F)F)=CC=2)=C1 DSEGFUSAJVUFLK-OFNKIYASSA-N 0.000 description 1
- FUKHGCVTMAEHRG-NRFANRHFSA-N n-[5-[(1r)-2-[bis[4-(difluoromethoxy)phenyl]methylamino]-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC([C@@H](O)CNC(C=2C=CC(OC(F)F)=CC=2)C=2C=CC(OC(F)F)=CC=2)=C1 FUKHGCVTMAEHRG-NRFANRHFSA-N 0.000 description 1
- TUYWTLTWNJOZNY-UHFFFAOYSA-N n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-[2-(2h-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]-5-propan-2-ylpyridine-2-sulfonamide Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2C=C(N=CC=2)C2=NNN=N2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)C)C=N1 TUYWTLTWNJOZNY-UHFFFAOYSA-N 0.000 description 1
- GBHZRMWZYDRRRK-UHFFFAOYSA-N n-[[2-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]-5-(1,3-oxazol-2-yl)phenyl]methyl]-3,3-dimethylbutanamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C(=CC=CC=2)C=2C(=CC(=CC=2)C=2OC=CN=2)CNC(=O)CC(C)(C)C)=C1C GBHZRMWZYDRRRK-UHFFFAOYSA-N 0.000 description 1
- OZMWNRSILHTVFV-UHFFFAOYSA-N n-butyl-3-[(4-decoxybenzoyl)amino]-4-methylsulfanylbenzamide Chemical compound C1=CC(OCCCCCCCCCC)=CC=C1C(=O)NC1=CC(C(=O)NCCCC)=CC=C1SC OZMWNRSILHTVFV-UHFFFAOYSA-N 0.000 description 1
- 229960004255 nadolol Drugs 0.000 description 1
- VWPOSFSPZNDTMJ-UCWKZMIHSA-N nadolol Chemical compound C1[C@@H](O)[C@@H](O)CC2=C1C=CC=C2OCC(O)CNC(C)(C)C VWPOSFSPZNDTMJ-UCWKZMIHSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229960000698 nateglinide Drugs 0.000 description 1
- OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 description 1
- 125000005484 neopentoxy group Chemical group 0.000 description 1
- 125000005933 neopentyloxycarbonyl group Chemical group 0.000 description 1
- PKWDZWYVIHVNKS-UHFFFAOYSA-N netoglitazone Chemical compound FC1=CC=CC=C1COC1=CC=C(C=C(CC2C(NC(=O)S2)=O)C=C2)C2=C1 PKWDZWYVIHVNKS-UHFFFAOYSA-N 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- PCJGZPGTCUMMOT-ISULXFBGSA-N neurotensin Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 PCJGZPGTCUMMOT-ISULXFBGSA-N 0.000 description 1
- 230000000508 neurotrophic effect Effects 0.000 description 1
- AIKVCUNQWYTVTO-UHFFFAOYSA-N nicardipine hydrochloride Chemical compound Cl.COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 AIKVCUNQWYTVTO-UHFFFAOYSA-N 0.000 description 1
- 229960002289 nicardipine hydrochloride Drugs 0.000 description 1
- 229960000827 niceritrol Drugs 0.000 description 1
- 229950005171 nicofibrate Drugs 0.000 description 1
- RARQHAFNGNPQCZ-UHFFFAOYSA-N nicofibrate Chemical compound C=1C=CN=CC=1COC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 RARQHAFNGNPQCZ-UHFFFAOYSA-N 0.000 description 1
- 229950001071 nicomol Drugs 0.000 description 1
- 229960002497 nicorandil Drugs 0.000 description 1
- LBHIOVVIQHSOQN-UHFFFAOYSA-N nicorandil Chemical compound [O-][N+](=O)OCCNC(=O)C1=CC=CN=C1 LBHIOVVIQHSOQN-UHFFFAOYSA-N 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960001597 nifedipine Drugs 0.000 description 1
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
- 229960005366 nilvadipine Drugs 0.000 description 1
- 229960000227 nisoldipine Drugs 0.000 description 1
- 229960005425 nitrendipine Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229940127221 norepinephrine reuptake inhibitor Drugs 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- LVRLSYPNFFBYCZ-VGWMRTNUSA-N omapatrilat Chemical compound C([C@H](S)C(=O)N[C@H]1CCS[C@H]2CCC[C@H](N2C1=O)C(=O)O)C1=CC=CC=C1 LVRLSYPNFFBYCZ-VGWMRTNUSA-N 0.000 description 1
- 229950000973 omapatrilat Drugs 0.000 description 1
- 239000003399 opiate peptide Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- 229960001243 orlistat Drugs 0.000 description 1
- BYERNKLVBZCFJW-UHFFFAOYSA-N oxadiazole;1h-pyrazole Chemical compound C=1C=NNC=1.C1=CON=N1 BYERNKLVBZCFJW-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- HXNFUBHNUDHIGC-UHFFFAOYSA-N oxypurinol Chemical compound O=C1NC(=O)N=C2NNC=C21 HXNFUBHNUDHIGC-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229960004493 penbutolol sulfate Drugs 0.000 description 1
- FEDSNBHHWZEYTP-ZFQYHYQMSA-N penbutolol sulfate Chemical compound OS(O)(=O)=O.CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1.CC(C)(C)NC[C@H](O)COC1=CC=CC=C1C1CCCC1 FEDSNBHHWZEYTP-ZFQYHYQMSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- 239000003614 peroxisome proliferator Substances 0.000 description 1
- AFOGBLYPWJJVAL-UHFFFAOYSA-N phenbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=CC=C1 AFOGBLYPWJJVAL-UHFFFAOYSA-N 0.000 description 1
- 229950008557 phenbutamide Drugs 0.000 description 1
- 229960003243 phenformin Drugs 0.000 description 1
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 1
- 229960003562 phentermine Drugs 0.000 description 1
- DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 description 1
- 229960000395 phenylpropanolamine Drugs 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 229960004984 pimagedine hydrochloride Drugs 0.000 description 1
- 229960002508 pindolol Drugs 0.000 description 1
- PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 description 1
- 229960002827 pioglitazone hydrochloride Drugs 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 description 1
- 229960002797 pitavastatin Drugs 0.000 description 1
- 230000001817 pituitary effect Effects 0.000 description 1
- 108010017843 platelet-derived growth factor A Proteins 0.000 description 1
- 108010000685 platelet-derived growth factor AB Proteins 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229950010884 ponalrestat Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- MZWCHWWQSPPZRH-UHFFFAOYSA-M potassium;4-(7-ethyl-1,3-benzodioxol-5-yl)-1,1-dioxo-2-[2-(trifluoromethyl)phenyl]-1$l^{6},2-benzothiazine-3-carboxylate Chemical compound [K+].C=1C=2OCOC=2C(CC)=CC=1C(C1=CC=CC=C1S1(=O)=O)=C(C([O-])=O)N1C1=CC=CC=C1C(F)(F)F MZWCHWWQSPPZRH-UHFFFAOYSA-M 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 compound [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
- 108010029667 pramlintide Proteins 0.000 description 1
- NRKVKVQDUCJPIZ-MKAGXXMWSA-N pramlintide acetate Chemical compound C([C@@H](C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@@H](N)CCCCN)[C@@H](C)O)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 NRKVKVQDUCJPIZ-MKAGXXMWSA-N 0.000 description 1
- 229960004457 pramlintide acetate Drugs 0.000 description 1
- 229960002965 pravastatin Drugs 0.000 description 1
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
- WFXFYZULCQKPIP-UHFFFAOYSA-N prazosin hydrochloride Chemical compound [H+].[Cl-].N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 WFXFYZULCQKPIP-UHFFFAOYSA-N 0.000 description 1
- 229960002386 prazosin hydrochloride Drugs 0.000 description 1
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
- 229960003081 probenecid Drugs 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108010070701 procolipase Proteins 0.000 description 1
- AZGZXUZMWKHDDH-UHFFFAOYSA-N propan-2-yl n-[3-chloro-5-[1-[[6-[2-(5-ethyl-4-methyl-1,3-thiazol-2-yl)ethyl]-4-morpholin-4-ylpyridin-2-yl]amino]ethyl]phenyl]carbamate Chemical compound CC1=C(CC)SC(CCC=2N=C(NC(C)C=3C=C(NC(=O)OC(C)C)C=C(Cl)C=3)C=C(C=2)N2CCOCC2)=N1 AZGZXUZMWKHDDH-UHFFFAOYSA-N 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229960004604 propranolol hydrochloride Drugs 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol hydrochloride Natural products C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 210000000512 proximal kidney tubule Anatomy 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000013014 purified material Substances 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 235000008151 pyridoxamine Nutrition 0.000 description 1
- 239000011699 pyridoxamine Substances 0.000 description 1
- 229960003042 quinapril hydrochloride Drugs 0.000 description 1
- IBBLRJGOOANPTQ-JKVLGAQCSA-N quinapril hydrochloride Chemical compound Cl.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 IBBLRJGOOANPTQ-JKVLGAQCSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 108700040249 racecadotril Proteins 0.000 description 1
- 229960003401 ramipril Drugs 0.000 description 1
- 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 1
- 230000009103 reabsorption Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229950010098 rentiapril Drugs 0.000 description 1
- BSHDUMDXSRLRBI-JOYOIKCWSA-N rentiapril Chemical compound SCCC(=O)N1[C@H](C(=O)O)CS[C@@H]1C1=CC=CC=C1O BSHDUMDXSRLRBI-JOYOIKCWSA-N 0.000 description 1
- 229960002354 repaglinide Drugs 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- JZCPYUJPEARBJL-UHFFFAOYSA-N rimonabant Chemical compound CC=1C(C(=O)NN2CCCCC2)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 JZCPYUJPEARBJL-UHFFFAOYSA-N 0.000 description 1
- 229960003015 rimonabant Drugs 0.000 description 1
- CRPGRUONUFDYBG-UHFFFAOYSA-N risarestat Chemical compound C1=C(OCC)C(OCCCCC)=CC=C1C1C(=O)NC(=O)S1 CRPGRUONUFDYBG-UHFFFAOYSA-N 0.000 description 1
- 229950006433 risarestat Drugs 0.000 description 1
- XMSXOLDPMGMWTH-UHFFFAOYSA-N rivoglitazone Chemical compound CN1C2=CC(OC)=CC=C2N=C1COC(C=C1)=CC=C1CC1SC(=O)NC1=O XMSXOLDPMGMWTH-UHFFFAOYSA-N 0.000 description 1
- HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 description 1
- 229950005741 rolipram Drugs 0.000 description 1
- 229960000804 ronifibrate Drugs 0.000 description 1
- AYJVGKWCGIYEAK-UHFFFAOYSA-N ronifibrate Chemical compound C=1C=CN=CC=1C(=O)OCCCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 AYJVGKWCGIYEAK-UHFFFAOYSA-N 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- SUFUKZSWUHZXAV-BTJKTKAUSA-N rosiglitazone maleate Chemical compound [H+].[H+].[O-]C(=O)\C=C/C([O-])=O.C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O SUFUKZSWUHZXAV-BTJKTKAUSA-N 0.000 description 1
- 229960003271 rosiglitazone maleate Drugs 0.000 description 1
- 229960000672 rosuvastatin Drugs 0.000 description 1
- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 description 1
- 229950001780 sampatrilat Drugs 0.000 description 1
- FFYNAVGJSYHHFO-UHFFFAOYSA-N sarpogrelate Chemical compound COC1=CC=CC(CCC=2C(=CC=CC=2)OCC(CN(C)C)OC(=O)CCC(O)=O)=C1 FFYNAVGJSYHHFO-UHFFFAOYSA-N 0.000 description 1
- 229950005789 sarpogrelate Drugs 0.000 description 1
- IMNTVVOUWFPRSB-JWQCQUIFSA-N sch-48461 Chemical compound C1=CC(OC)=CC=C1[C@H]1N(C=2C=CC(OC)=CC=2)C(=O)[C@@H]1CCCC1=CC=CC=C1 IMNTVVOUWFPRSB-JWQCQUIFSA-N 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 229960003660 sertraline hydrochloride Drugs 0.000 description 1
- 229960003466 sibutramine hydrochloride Drugs 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 229960002855 simvastatin Drugs 0.000 description 1
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
- PHWXUGHIIBDVKD-UHFFFAOYSA-N sitaxentan Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)CC=2C(=CC=3OCOC=3C=2)C)=C1Cl PHWXUGHIIBDVKD-UHFFFAOYSA-N 0.000 description 1
- 229960002578 sitaxentan Drugs 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- NTDIRNUKAZNMSW-IYVGUKHKSA-M sodium;(3s,5r,6e)-9,9-bis(4-fluorophenyl)-3,5-dihydroxy-8-(1-methyltetrazol-5-yl)nona-6,8-dienoate Chemical compound [Na+].CN1N=NN=C1C(\C=C\[C@H](O)C[C@H](O)CC([O-])=O)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 NTDIRNUKAZNMSW-IYVGUKHKSA-M 0.000 description 1
- FBSZSOXTWRKLKD-UHFFFAOYSA-M sodium;(4-chlorophenyl)sulfonyl-[(4-cyano-5-methyl-2-phenylpyrazol-3-yl)carbamoyl]azanide Chemical compound [Na+].N#CC=1C(C)=NN(C=2C=CC=CC=2)C=1NC(=O)[N-]S(=O)(=O)C1=CC=C(Cl)C=C1 FBSZSOXTWRKLKD-UHFFFAOYSA-M 0.000 description 1
- AMCPCELVARAPHJ-UHFFFAOYSA-M sodium;5-[[4-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propanoyl]phenyl]methyl]-1,3-thiazolidin-3-ide-2,4-dione Chemical compound [Na+].CC=1OC(C=2C=CC=CC=2)=NC=1CCC(=O)C(C=C1)=CC=C1CC1SC(=O)[N-]C1=O AMCPCELVARAPHJ-UHFFFAOYSA-M 0.000 description 1
- LLDXOPKUNJTIRF-QFIPXVFZSA-N solabegron Chemical compound C([C@H](O)C=1C=C(Cl)C=CC=1)NCCNC(C=1)=CC=CC=1C1=CC=CC(C(O)=O)=C1 LLDXOPKUNJTIRF-QFIPXVFZSA-N 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229960000553 somatostatin Drugs 0.000 description 1
- 229940075620 somatostatin analogue Drugs 0.000 description 1
- LXANPKRCLVQAOG-NSHDSACASA-N sorbinil Chemical compound C12=CC(F)=CC=C2OCC[C@@]21NC(=O)NC2=O LXANPKRCLVQAOG-NSHDSACASA-N 0.000 description 1
- 229950004311 sorbinil Drugs 0.000 description 1
- 239000000600 sorbitol 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
- 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
- 229960002256 spironolactone Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
- 229960001052 streptozocin Drugs 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229950008418 talipexole Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960005187 telmisartan Drugs 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
- VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 description 1
- 229960001909 terazosin hydrochloride Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WUBVEMGCQRSBBT-UHFFFAOYSA-N tert-butyl 4-(trifluoromethylsulfonyloxy)-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(OS(=O)(=O)C(F)(F)F)=CC1 WUBVEMGCQRSBBT-UHFFFAOYSA-N 0.000 description 1
- 125000005922 tert-pentoxy group Chemical group 0.000 description 1
- 229960000347 tertatolol hydrochloride Drugs 0.000 description 1
- 108091008646 testicular receptors Proteins 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229950000584 tezosentan Drugs 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 108090000721 thyroid hormone receptors Proteins 0.000 description 1
- 102000004217 thyroid hormone receptors Human genes 0.000 description 1
- 229960000874 thyrotropin Drugs 0.000 description 1
- 230000001748 thyrotropin Effects 0.000 description 1
- MTKNGOHFNXIVOS-UHFFFAOYSA-N ticlopidine hydrochloride Chemical compound [H+].[Cl-].ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 MTKNGOHFNXIVOS-UHFFFAOYSA-N 0.000 description 1
- 229960002961 ticlopidine hydrochloride Drugs 0.000 description 1
- 229950008411 tilisolol Drugs 0.000 description 1
- TWVUMMQUXMYOOH-UHFFFAOYSA-N tilisolol Chemical compound C1=CC=C2C(=O)N(C)C=C(OCC(O)CNC(C)(C)C)C2=C1 TWVUMMQUXMYOOH-UHFFFAOYSA-N 0.000 description 1
- 229960005221 timolol maleate Drugs 0.000 description 1
- 229950001089 todralazine Drugs 0.000 description 1
- 229960002277 tolazamide Drugs 0.000 description 1
- OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- LUBHDINQXIHVLS-UHFFFAOYSA-N tolrestat Chemical compound OC(=O)CN(C)C(=S)C1=CC=CC2=C(C(F)(F)F)C(OC)=CC=C21 LUBHDINQXIHVLS-UHFFFAOYSA-N 0.000 description 1
- 229960003069 tolrestat Drugs 0.000 description 1
- 229960002051 trandolapril Drugs 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 229960000363 trapidil Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 229960001288 triamterene Drugs 0.000 description 1
- LMJSLTNSBFUCMU-UHFFFAOYSA-N trichlormethiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC(C(Cl)Cl)NS2(=O)=O LMJSLTNSBFUCMU-UHFFFAOYSA-N 0.000 description 1
- 229960004813 trichlormethiazide Drugs 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- UHLOVGKIEARANS-QZHINBJYSA-N tripamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(=O)NN2C[C@@H]3[C@H]4CC[C@H](C4)[C@@H]3C2)=C1 UHLOVGKIEARANS-QZHINBJYSA-N 0.000 description 1
- 229950004678 tripamide Drugs 0.000 description 1
- 108010039189 tripeptidyl-peptidase 2 Proteins 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000003424 uricosuric effect Effects 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
- 239000000777 urocortin Substances 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960004699 valsartan Drugs 0.000 description 1
- ACWBQPMHZXGDFX-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=NN1 ACWBQPMHZXGDFX-QFIPXVFZSA-N 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 229960000881 verapamil hydrochloride Drugs 0.000 description 1
- 229960001729 voglibose Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- SXONDGSPUVNZLO-UHFFFAOYSA-N zenarestat Chemical compound O=C1N(CC(=O)O)C2=CC(Cl)=CC=C2C(=O)N1CC1=CC=C(Br)C=C1F SXONDGSPUVNZLO-UHFFFAOYSA-N 0.000 description 1
- 229950006343 zenarestat Drugs 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
- 229950005346 zopolrestat Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/18—Growth factors; Growth regulators
- A61K38/185—Nerve growth factor [NGF]; Brain derived neurotrophic factor [BDNF]; Ciliary neurotrophic factor [CNTF]; Glial derived neurotrophic factor [GDNF]; Neurotrophins, e.g. NT-3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
- A61K31/10—Sulfides; Sulfoxides; Sulfones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
- A61K31/37—Coumarins, e.g. psoralen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4166—1,3-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/7056—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing five-membered rings with nitrogen as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
- A61K31/7072—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/737—Sulfated polysaccharides, e.g. chondroitin sulfate, dermatan sulfate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/18—Growth factors; Growth regulators
- A61K38/1858—Platelet-derived growth factor [PDGF]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
- A61K38/28—Insulins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Zoology (AREA)
- Immunology (AREA)
- Gastroenterology & Hepatology (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Biotechnology (AREA)
- Heart & Thoracic Surgery (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Psychology (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Child & Adolescent Psychology (AREA)
- Vascular Medicine (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002244381 | 2002-08-23 | ||
| JP2002244381 | 2002-08-23 | ||
| JP2002324076A JP2004137245A (ja) | 2002-08-23 | 2002-11-07 | ピラゾール誘導体、それを含有する医薬組成物、その医薬用途及びその製造中間体 |
| JP2002324076 | 2002-11-07 | ||
| PCT/JP2003/010551 WO2004018491A1 (ja) | 2002-08-23 | 2003-08-21 | ピラゾール誘導体、それを含有する医薬組成物、その医薬用途及びその製造中間体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2386140T3 true ES2386140T3 (es) | 2012-08-10 |
Family
ID=31949579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03792760T Expired - Lifetime ES2386140T3 (es) | 2002-08-23 | 2003-08-21 | Derivados de pirazol, composición medicinal que contiene los mismos, uso medicinal de los mismos e intermedio para la producción de los mismos |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US7635684B2 (enExample) |
| EP (1) | EP1548024B1 (enExample) |
| JP (2) | JP2004137245A (enExample) |
| KR (1) | KR100985504B1 (enExample) |
| AU (1) | AU2003262263B8 (enExample) |
| BR (1) | BRPI0313694B8 (enExample) |
| CA (1) | CA2496329C (enExample) |
| ES (1) | ES2386140T3 (enExample) |
| IL (1) | IL167038A (enExample) |
| MX (1) | MXPA05002129A (enExample) |
| NO (1) | NO330569B1 (enExample) |
| NZ (1) | NZ538423A (enExample) |
| PL (1) | PL213094B1 (enExample) |
| RU (1) | RU2369613C2 (enExample) |
| TW (1) | TW200410980A (enExample) |
| WO (1) | WO2004018491A1 (enExample) |
Families Citing this family (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ538117A (en) * | 2002-08-08 | 2007-01-26 | Kissei Pharmaceutical | Pyrazole derivative, medicinal composition containing the same, medicinal use thereof, and intermediate for production thereof |
| JP2004137245A (ja) | 2002-08-23 | 2004-05-13 | Kissei Pharmaceut Co Ltd | ピラゾール誘導体、それを含有する医薬組成物、その医薬用途及びその製造中間体 |
| JP4606876B2 (ja) * | 2002-08-27 | 2011-01-05 | キッセイ薬品工業株式会社 | ピラゾール誘導体、それを含有する医薬組成物及びその医薬用途 |
| WO2004050122A1 (ja) * | 2002-12-04 | 2004-06-17 | Kissei Pharmaceutical Co., Ltd. | 高血糖症に起因する疾患の予防又は治療剤 |
| AU2003289440A1 (en) * | 2002-12-25 | 2004-07-22 | Kissei Pharmaceutical Co., Ltd. | Nitrogen-containing heterocycic derivatives, medicinal compositions containing the same and medicinal use thereof |
| US7375090B2 (en) * | 2003-08-26 | 2008-05-20 | Boehringer Ingelheim International Gmbh | Glucopyranosyloxy-pyrazoles, pharmaceutical compositions containing these compounds, the use thereof and processed for the preparation thereof |
| US7838552B2 (en) | 2004-06-04 | 2010-11-23 | Forest Laboratories Holdings Limited | Compositions comprising nebivolol |
| US7803838B2 (en) | 2004-06-04 | 2010-09-28 | Forest Laboratories Holdings Limited | Compositions comprising nebivolol |
| DE102004028241B4 (de) * | 2004-06-11 | 2007-09-13 | Sanofi-Aventis Deutschland Gmbh | Neue Fluorglykosidderivate von Pyrazolen, diese Verbindungen enthaltende Arzneimittel und Herstellung dieser Arzneimittel |
| WO2006054629A1 (ja) | 2004-11-18 | 2006-05-26 | Kissei Pharmaceutical Co., Ltd. | １－置換－３－（β－Ｄ－グリコピラノシル）含窒素ヘテロ環化合物、及びそれを含有する医薬 |
| JP2008007405A (ja) * | 2004-12-07 | 2008-01-17 | Takeda Chem Ind Ltd | カルボキサミド誘導体 |
| WO2007010015A1 (en) * | 2005-07-22 | 2007-01-25 | Boehringer Ingelheim International Gmbh | Processes for preparing pyrazole-o-glycoside derivatives and novel intermediates of said processes |
| UY30082A1 (es) | 2006-01-11 | 2007-08-31 | Boehringer Ingelheim Int | Forma cristalina de 1-(1-metiletil)-4`-((2-fluoro-4-metoxifenil)metil)-5`- metil-1h-pirazol-3`-o-b-d-glucopiranosido, un metodo para su preparacion y el uso de la misma para preparar medicamentos |
| JP2009167103A (ja) * | 2006-05-02 | 2009-07-30 | Taisho Pharmaceutical Co Ltd | ピラゾリル５−チオグリコシド化合物 |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| AR061026A1 (es) | 2006-05-19 | 2008-07-30 | Taisho Pharmaceutical Co Ltd | Compuesto glicitol c-fenilo y preparacion farmaceutica |
| CN101479254B (zh) | 2006-06-29 | 2012-05-30 | 大正制药株式会社 | C-苯基1-硫代山梨醇化合物 |
| AU2007332476A1 (en) | 2006-12-14 | 2008-06-19 | Taisho Pharmaceutical Co., Ltd. | 1-phenyl 1-thio-D-glucitol derivative |
| NZ586336A (en) | 2007-12-27 | 2011-06-30 | Kissei Pharmaceutical | Monosebacate of pyrazole derivative |
| US8354382B2 (en) | 2008-04-16 | 2013-01-15 | Kissei Pharmaceutical Co., Ltd. | Hemifumarate of a pyrazole derivative |
| ATE540040T1 (de) | 2008-08-28 | 2012-01-15 | Pfizer | Dioxabicycloä3.2.1üoctan-2,3,4-triolderivate |
| MY155658A (en) * | 2009-02-23 | 2015-11-13 | Taisho Pharmaceutical Co Ltd | A-isopropylphenyl glucitol compounds as sglti inhibitors |
| JPWO2011002001A1 (ja) * | 2009-07-01 | 2012-12-13 | キッセイ薬品工業株式会社 | ピラゾール誘導体とビグアナイド薬との組み合わせ医薬 |
| WO2011002011A1 (ja) * | 2009-07-01 | 2011-01-06 | キッセイ薬品工業株式会社 | Sglt1阻害薬とdpp-iv阻害薬を組み合わせてなる医薬 |
| TW201105337A (en) * | 2009-07-01 | 2011-02-16 | Dainippon Sumitomo Pharma Co | Medicine derived from a combination of SGLT1-inhibitor and insulin sensitizer |
| CN102574776A (zh) | 2009-07-31 | 2012-07-11 | 桑多斯股份公司 | ω-氨基-烷酰胺和ω-氨基-烷硫酰胺的制备方法及该方法的中间体 |
| EP2298782A1 (en) * | 2009-08-26 | 2011-03-23 | Sanofi-Aventis | Method for producing pyrazole glycoside derivatives |
| US20120270819A1 (en) | 2009-10-02 | 2012-10-25 | Sanofi | Use of compounds with sglt-1/sglt-2 inhibitor activity for producing medicaments for treatment of bone disease |
| WO2011048148A2 (en) | 2009-10-20 | 2011-04-28 | Novartis Ag | Glycoside derivative and uses thereof |
| US8163704B2 (en) | 2009-10-20 | 2012-04-24 | Novartis Ag | Glycoside derivatives and uses thereof |
| ME02016B (me) | 2009-11-02 | 2015-05-20 | Pfizer | Derivati dioksabiciklo[3.2.1]oktan-2,3,4-triola |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012010651A2 (en) | 2010-07-23 | 2012-01-26 | Sandoz Ag | Method for the preparation of omega-amino-alkaneamides and omega-amino-alkanethioamides as well as intermediates of this method |
| EP2607360B1 (en) | 2010-08-20 | 2015-08-19 | Taisho Pharmaceutical Co., Ltd. | 4-Isopropyl-6-methoxyphenyl glucitol compound |
| JP5656092B2 (ja) | 2010-08-20 | 2015-01-21 | 大正製薬株式会社 | ４−イソプロピルフェニルグルシトール化合物の結晶形及びその製造方法 |
| US8614195B2 (en) | 2011-04-14 | 2013-12-24 | Novartis Ag | Glycoside derivatives and uses thereof |
| BR112013026361A2 (pt) | 2011-04-14 | 2016-12-27 | Novartis Ag | derivados de glicosídeo e usos dos mesmos |
| AR087701A1 (es) * | 2011-08-31 | 2014-04-09 | Japan Tobacco Inc | Derivados de pirazol con actividad inhibidora de sglt1 |
| CA2872002C (en) | 2012-05-07 | 2019-01-15 | Masayuki Isaji | Pyrazole derivative and use thereof for medical purposes |
| UA113086C2 (xx) | 2012-05-10 | 2016-12-12 | Піразольні сполуки як інгібітори sglt1 | |
| TW201425326A (zh) * | 2012-10-05 | 2014-07-01 | Lilly Co Eli | 新穎脲化合物 |
| RU2015123738A (ru) | 2012-11-20 | 2017-01-10 | Лексикон Фармасьютикалз, Инк. | Ингибиторы котранспортера натрий-глюкозы 1 |
| RU2648467C2 (ru) | 2013-02-04 | 2018-03-26 | Тайсо Фармасьютикал Ко., Лтд. | Профилактическое или терапевтическое лекарственное средство для лечения запора |
| EP2774619B1 (de) | 2013-03-04 | 2016-05-18 | BioActive Food GmbH | Zusammensetzung zur Behandlung von hyperglykämischen Erkrankungen |
| US8652527B1 (en) | 2013-03-13 | 2014-02-18 | Upsher-Smith Laboratories, Inc | Extended-release topiramate capsules |
| US9101545B2 (en) | 2013-03-15 | 2015-08-11 | Upsher-Smith Laboratories, Inc. | Extended-release topiramate capsules |
| AR098670A1 (es) | 2013-11-08 | 2016-06-08 | Lilly Co Eli | Inhibidor de sglt1 |
| EP2944311A1 (de) | 2014-05-16 | 2015-11-18 | BioActive Food GmbH | Kombination von biologisch aktiven Substanzen zur Behandlung von hyperglykämischen Erkrankungen |
| US11186602B2 (en) | 2018-01-31 | 2021-11-30 | Sunshine Lake Pharma Co., Ltd. | Glucopyranosyl derivative and use thereof |
| MX2020009349A (es) | 2018-03-28 | 2021-04-28 | Avolynt | Método para el tratamiento de la hipoglucemia posprandial. |
| EP3886854A4 (en) | 2018-11-30 | 2022-07-06 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| BR112021024165A2 (pt) * | 2019-05-31 | 2022-04-26 | Avolynt | Composições e métodos para o tratamento de doenças metabólicas |
| WO2024254354A1 (en) * | 2023-06-06 | 2024-12-12 | Vogenx | Compositions and methods for treating refractory or intractable epilepsy |
| WO2024254302A1 (en) * | 2023-06-06 | 2024-12-12 | Vogenx | Compositions and methods for treating hyperinsulinemic hypoglycemia |
| WO2025117962A1 (en) * | 2023-12-01 | 2025-06-05 | Vogenx | Compositions and methods for treating glucose-dependent insulinotropic peptide-dependent cushing's syndrome |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2219172C2 (ru) * | 1999-04-06 | 2003-12-20 | Санкио Компани, Лимитед | α-ЗАМЕЩЕННЫЕ ПРОИЗВОДНЫЕ КАРБОНОВЫХ КИСЛОТ |
| CA2382480C (en) * | 1999-08-31 | 2008-09-30 | Kissei Pharmaceutical Co., Ltd. | Glucopyranosyloxypyrazole derivatives, medicinal compositions containing the same and intermediates in the production thereof |
| EP2163555A1 (en) * | 2000-11-02 | 2010-03-17 | Ajinomoto Co., Inc. | New pyrazole derivatives and diabetic medicine containing them |
| SK287786B6 (sk) * | 2000-12-28 | 2011-09-05 | Kissei Pharmaceutical Co., Ltd. | Glukopyranosyloxypyrazolový derivát, farmaceutická kompozícia alebo kombinácia s jeho obsahom a ich použitie |
| NZ538117A (en) * | 2002-08-08 | 2007-01-26 | Kissei Pharmaceutical | Pyrazole derivative, medicinal composition containing the same, medicinal use thereof, and intermediate for production thereof |
| JP2004137245A (ja) | 2002-08-23 | 2004-05-13 | Kissei Pharmaceut Co Ltd | ピラゾール誘導体、それを含有する医薬組成物、その医薬用途及びその製造中間体 |
| WO2004031203A1 (ja) * | 2002-10-04 | 2004-04-15 | Kissei Pharmaceutical Co., Ltd. | ピラゾール誘導体、それを含有する医薬組成物、その医薬用途及びその製造中間体 |
| US7576064B2 (en) * | 2003-06-20 | 2009-08-18 | Kissei Pharmaceutical Co., Ltd. | Pyrazole derivative, drug composition containing the same and production intermediate therefor |
-
2002
- 2002-11-07 JP JP2002324076A patent/JP2004137245A/ja active Pending
-
2003
- 2003-08-21 KR KR1020057003117A patent/KR100985504B1/ko not_active Expired - Lifetime
- 2003-08-21 MX MXPA05002129A patent/MXPA05002129A/es active IP Right Grant
- 2003-08-21 WO PCT/JP2003/010551 patent/WO2004018491A1/ja not_active Ceased
- 2003-08-21 ES ES03792760T patent/ES2386140T3/es not_active Expired - Lifetime
- 2003-08-21 PL PL375551A patent/PL213094B1/pl unknown
- 2003-08-21 US US10/525,197 patent/US7635684B2/en active Active
- 2003-08-21 BR BRPI0313694A patent/BRPI0313694B8/pt not_active IP Right Cessation
- 2003-08-21 RU RU2005108055/04A patent/RU2369613C2/ru active
- 2003-08-21 CA CA2496329A patent/CA2496329C/en not_active Expired - Lifetime
- 2003-08-21 JP JP2005501231A patent/JP4597048B2/ja not_active Expired - Lifetime
- 2003-08-21 NZ NZ538423A patent/NZ538423A/en not_active IP Right Cessation
- 2003-08-21 AU AU2003262263A patent/AU2003262263B8/en not_active Expired
- 2003-08-21 EP EP03792760A patent/EP1548024B1/en not_active Expired - Lifetime
- 2003-08-22 TW TW092123126A patent/TW200410980A/zh not_active IP Right Cessation
-
2005
- 2005-02-22 IL IL167038A patent/IL167038A/en unknown
- 2005-03-17 NO NO20051411A patent/NO330569B1/no not_active IP Right Cessation
-
2009
- 2009-04-09 US US12/421,236 patent/US8324176B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR20050038633A (ko) | 2005-04-27 |
| EP1548024A1 (en) | 2005-06-29 |
| NO20051411L (no) | 2005-04-26 |
| BRPI0313694B8 (pt) | 2021-05-25 |
| NZ538423A (en) | 2007-02-23 |
| AU2003262263B2 (en) | 2009-06-25 |
| BRPI0313694B1 (pt) | 2017-12-19 |
| PL375551A1 (en) | 2005-11-28 |
| MXPA05002129A (es) | 2005-06-03 |
| US8324176B2 (en) | 2012-12-04 |
| JPWO2004018491A1 (ja) | 2005-12-08 |
| KR100985504B1 (ko) | 2010-10-05 |
| RU2369613C2 (ru) | 2009-10-10 |
| AU2003262263B8 (en) | 2009-08-06 |
| TW200410980A (en) | 2004-07-01 |
| RU2005108055A (ru) | 2006-02-10 |
| JP4597048B2 (ja) | 2010-12-15 |
| HK1082744A1 (zh) | 2006-06-16 |
| IL167038A (en) | 2010-11-30 |
| US20090203633A1 (en) | 2009-08-13 |
| TWI298071B (enExample) | 2008-06-21 |
| EP1548024A4 (en) | 2010-05-12 |
| JP2004137245A (ja) | 2004-05-13 |
| US7635684B2 (en) | 2009-12-22 |
| BR0313694A (pt) | 2005-07-05 |
| AU2003262263A1 (en) | 2004-03-11 |
| WO2004018491A1 (ja) | 2004-03-04 |
| PL213094B1 (pl) | 2013-01-31 |
| CA2496329A1 (en) | 2004-03-04 |
| NO330569B1 (no) | 2011-05-16 |
| CA2496329C (en) | 2012-05-15 |
| EP1548024B1 (en) | 2012-06-06 |
| US20050272669A1 (en) | 2005-12-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2386140T3 (es) | Derivados de pirazol, composición medicinal que contiene los mismos, uso medicinal de los mismos e intermedio para la producción de los mismos | |
| ES2345250T3 (es) | Derivado de pirazol en la composicion medicinal que contiene el mismo, el uso medicinal del mismo, y un intermedio para la produccion del mismo. | |
| US7655633B2 (en) | Nitrogen-containing heterocyclic derivatives, medicinal compositions containing the same and medicinal use thereof | |
| ES2468219T3 (es) | Derivados de anillo condensado nitrogenados, composiciones medicinales que contienen los derivados y uso de los mismos como fármacos | |
| CN100413878C (zh) | 吡唑衍生物、含该衍生物的医药组合物、其医药用途及用于制备的中间体 | |
| HK1082744B (en) | Pyrazole derivatives, medicinal composition containing the same, medicinal use thereof, and intermediate for production thereof |