NO872463L

NO872463L - Fremgangsmaate for fremstilling av dihydropyridinderivater med antihypertensiv virkning.

Fremgangsmaate for fremstilling av dihydropyridinderivater med antihypertensiv virkning.

Info

Publication number: NO872463L
Authority: NO; Norway
Prior art keywords: nitrophenyl; carbomethoxy; dimethyl; phenoxy; dihydropyridine
Prior art date: 1986-06-13

Application number

NO872463A

Other languages

English (en)

Norwegian (no)

Other versions

NO872463D0 (no

Inventor

Gilles Genain

Original Assignee

Syntex Lab

Priority date

1986-06-13

Filing date

1987-06-12

Publication date

1987-12-14

1987-06-12 Application filed by Syntex Lab filed Critical Syntex Lab

1987-06-12 Publication of NO872463D0 publication Critical patent/NO872463D0/no

1987-12-14 Publication of NO872463L publication Critical patent/NO872463L/no

Links

238000002360 preparation method Methods 0.000 title claims description 55
238000000034 method Methods 0.000 title claims description 37
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title description 17
230000003276 anti-hypertensive effect Effects 0.000 title description 6
229940085304 dihydropyridine derivative selective calcium channel blockers with mainly vascular effects Drugs 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 287
-1 alkoxycycloalkyl Chemical group 0.000 claims description 129
125000000217 alkyl group Chemical group 0.000 claims description 83
239000002904 solvent Substances 0.000 claims description 65
239000000203 mixture Substances 0.000 claims description 44
150000003839 salts Chemical class 0.000 claims description 37
239000002253 acid Substances 0.000 claims description 28
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 28
230000003287 optical effect Effects 0.000 claims description 20
238000010992 reflux Methods 0.000 claims description 19
KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 17
150000002367 halogens Chemical class 0.000 claims description 17
KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 claims description 16
125000000623 heterocyclic group Chemical group 0.000 claims description 15
125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
125000002252 acyl group Chemical group 0.000 claims description 13
125000000753 cycloalkyl group Chemical group 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 11
125000002947 alkylene group Chemical group 0.000 claims description 11
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 11
125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 11
229920006395 saturated elastomer Polymers 0.000 claims description 11
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 11
125000005842 heteroatom Chemical group 0.000 claims description 10
229910052500 inorganic mineral Inorganic materials 0.000 claims description 10
239000011707 mineral Substances 0.000 claims description 10
125000004430 oxygen atom Chemical group O* 0.000 claims description 10
AAKPGBJVBKCHHC-UHFFFAOYSA-N 3-o-methyl 5-o-[3-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]propyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCOC3OCCCC3)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 AAKPGBJVBKCHHC-UHFFFAOYSA-N 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
239000000825 pharmaceutical preparation Substances 0.000 claims description 8
125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 claims description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 6
230000002526 effect on cardiovascular system Effects 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 claims description 6
AAKPGBJVBKCHHC-MILIPEGGSA-N 3-o-methyl 5-o-[3-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]propyl] (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1([C@@H]2C(=C(C)NC(C)=C2C(=O)OC)C(=O)OCCCOC=2C=CC(CCOC3OCCCC3)=CC=2)=CC=CC([N+]([O-])=O)=C1 AAKPGBJVBKCHHC-MILIPEGGSA-N 0.000 claims description 4
FGLNHXKNBBFDTO-UHFFFAOYSA-N 5-o-[2-[4-(2-hydroxyethyl)phenoxy]ethyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC=2C=CC(CCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 FGLNHXKNBBFDTO-UHFFFAOYSA-N 0.000 claims description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
239000005977 Ethylene Substances 0.000 claims description 4
239000005557 antagonist Substances 0.000 claims description 4
230000003185 calcium uptake Effects 0.000 claims description 4
150000007529 inorganic bases Chemical class 0.000 claims description 4
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 4
GPLGAQQQNWMVMM-UHFFFAOYSA-N n,n-dimethylcon-5-enin-3-amine Chemical compound C1C=C2CC(N(C)C)CCC2(C)C2C1C1CCC3C(C)N(C)CC31CC2 GPLGAQQQNWMVMM-UHFFFAOYSA-N 0.000 claims description 4
150000007530 organic bases Chemical class 0.000 claims description 4
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
WHJQWUXKUSLABI-UHFFFAOYSA-N 5-o-[3-[4-(2-hydroxyethyl)phenoxy]propyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 WHJQWUXKUSLABI-UHFFFAOYSA-N 0.000 claims description 3
235000001258 Cinchona calisaya Nutrition 0.000 claims description 3
239000012024 dehydrating agents‎ Substances 0.000 claims description 3
229960001404 quinidine Drugs 0.000 claims description 3
229960000948 quinine Drugs 0.000 claims description 3
150000003512 tertiary amines Chemical class 0.000 claims description 3
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims description 2
MTXSIJUGVMTTMU-JTQLQIEISA-N (S)-anabasine Chemical compound N1CCCC[C@H]1C1=CC=CN=C1 MTXSIJUGVMTTMU-JTQLQIEISA-N 0.000 claims description 2
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 2
PIIQLZXRLGJEKE-LSDHHAIUSA-N 3-[(3r,4r)-3-ethenylpiperidin-4-yl]-1-quinolin-4-ylpropan-1-one Chemical compound C=C[C@H]1CNCC[C@H]1CCC(=O)C1=CC=NC2=CC=CC=C12 PIIQLZXRLGJEKE-LSDHHAIUSA-N 0.000 claims description 2
MDUKHCZXGKVKOT-UHFFFAOYSA-N 3-o-methyl 5-o-[3-[4-(2-propoxyethyl)phenoxy]propyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CCOCCC)=CC=C1OCCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 MDUKHCZXGKVKOT-UHFFFAOYSA-N 0.000 claims description 2
AAKPGBJVBKCHHC-DINWUYGQSA-N 3-o-methyl 5-o-[3-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]propyl] (4r)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1([C@H]2C(=C(C)NC(C)=C2C(=O)OC)C(=O)OCCCOC=2C=CC(CCOC3OCCCC3)=CC=2)=CC=CC([N+]([O-])=O)=C1 AAKPGBJVBKCHHC-DINWUYGQSA-N 0.000 claims description 2
USEYWIBMTKYFBX-UHFFFAOYSA-N 3-o-methyl 5-o-[3-[4-[2-(propoxymethoxy)ethyl]phenoxy]propyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CCOCOCCC)=CC=C1OCCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 USEYWIBMTKYFBX-UHFFFAOYSA-N 0.000 claims description 2
VIWGGBGFDJTZDS-UHFFFAOYSA-N 5-o-[2-[4-(2-methoxyethyl)phenoxy]ethyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CCOC)=CC=C1OCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 VIWGGBGFDJTZDS-UHFFFAOYSA-N 0.000 claims description 2
WHJQWUXKUSLABI-RUZDIDTESA-N 5-o-[3-[4-(2-hydroxyethyl)phenoxy]propyl] 3-o-methyl (4r)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1([C@H]2C(=C(C)NC(C)=C2C(=O)OC)C(=O)OCCCOC=2C=CC(CCO)=CC=2)=CC=CC([N+]([O-])=O)=C1 WHJQWUXKUSLABI-RUZDIDTESA-N 0.000 claims description 2
WHJQWUXKUSLABI-VWLOTQADSA-N 5-o-[3-[4-(2-hydroxyethyl)phenoxy]propyl] 3-o-methyl (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1([C@@H]2C(=C(C)NC(C)=C2C(=O)OC)C(=O)OCCCOC=2C=CC(CCO)=CC=2)=CC=CC([N+]([O-])=O)=C1 WHJQWUXKUSLABI-VWLOTQADSA-N 0.000 claims description 2
ZVKKIEBOQWHQFL-UHFFFAOYSA-N 5-o-[3-[4-(2-hydroxyethyl)phenoxy]propyl] 3-o-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCO)=CC=2)C1C1=CC=CC(Cl)=C1Cl ZVKKIEBOQWHQFL-UHFFFAOYSA-N 0.000 claims description 2
UESDFSTWYPJWFC-UHFFFAOYSA-N 5-o-[3-[4-(2-methoxyethyl)phenoxy]propyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CCOC)=CC=C1OCCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 UESDFSTWYPJWFC-UHFFFAOYSA-N 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
239000004475 Arginine Substances 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
229910002651 NO3 Inorganic materials 0.000 claims description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
229930014345 anabasine Natural products 0.000 claims description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 2
RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 claims description 2
RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 claims description 2
229960000632 dexamfetamine Drugs 0.000 claims description 2
229960002442 glucosamine Drugs 0.000 claims description 2
229960005181 morphine Drugs 0.000 claims description 2
ZLEZHBUYIBSRDP-JEBGQCBNSA-N 3-o-methyl 5-o-[2-[4-(2-propoxypropyl)phenoxy]ethyl] (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CC(C)OCCC)=CC=C1OCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 ZLEZHBUYIBSRDP-JEBGQCBNSA-N 0.000 claims 1
ZLEZHBUYIBSRDP-UHFFFAOYSA-N 3-o-methyl 5-o-[2-[4-(2-propoxypropyl)phenoxy]ethyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CC(C)OCCC)=CC=C1OCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 ZLEZHBUYIBSRDP-UHFFFAOYSA-N 0.000 claims 1
SJXAKLRKQPQDJB-BTMGADRYSA-N 3-o-methyl 5-o-[2-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]ethyl] (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1([C@@H]2C(=C(C)NC(C)=C2C(=O)OC)C(=O)OCCOC=2C=CC(CCOC3OCCCC3)=CC=2)=CC=CC([N+]([O-])=O)=C1 SJXAKLRKQPQDJB-BTMGADRYSA-N 0.000 claims 1
MLRMMUFHVGRQRJ-GPWDHUIYSA-N 3-o-methyl 5-o-[2-[4-[2-(oxan-2-yloxy)propyl]phenoxy]ethyl] (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1([C@@H]2C(=C(C)NC(C)=C2C(=O)OC)C(=O)OCCOC=2C=CC(CC(C)OC3OCCCC3)=CC=2)=CC=CC([N+]([O-])=O)=C1 MLRMMUFHVGRQRJ-GPWDHUIYSA-N 0.000 claims 1
YJIZGOPSUJZOFY-NDEPHWFRSA-N 3-o-methyl 5-o-[2-[4-[2-(propoxymethoxy)ethyl]phenoxy]ethyl] (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CCOCOCCC)=CC=C1OCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 YJIZGOPSUJZOFY-NDEPHWFRSA-N 0.000 claims 1
YJIZGOPSUJZOFY-UHFFFAOYSA-N 3-o-methyl 5-o-[2-[4-[2-(propoxymethoxy)ethyl]phenoxy]ethyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CCOCOCCC)=CC=C1OCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 YJIZGOPSUJZOFY-UHFFFAOYSA-N 0.000 claims 1
PHSAOLYFIRERAP-PRTIIRGTSA-N 3-o-methyl 5-o-[2-[4-[2-(propoxymethoxy)propyl]phenoxy]ethyl] (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CC(C)OCOCCC)=CC=C1OCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 PHSAOLYFIRERAP-PRTIIRGTSA-N 0.000 claims 1
MDUKHCZXGKVKOT-MUUNZHRXSA-N 3-o-methyl 5-o-[3-[4-(2-propoxyethyl)phenoxy]propyl] (4r)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CCOCCC)=CC=C1OCCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 MDUKHCZXGKVKOT-MUUNZHRXSA-N 0.000 claims 1
MDUKHCZXGKVKOT-NDEPHWFRSA-N 3-o-methyl 5-o-[3-[4-(2-propoxyethyl)phenoxy]propyl] (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CCOCCC)=CC=C1OCCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 MDUKHCZXGKVKOT-NDEPHWFRSA-N 0.000 claims 1
OAKDGTOSZQSIDS-UHFFFAOYSA-N 3-o-methyl 5-o-[3-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]propyl] 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCOC3OCCCC3)=CC=2)C1C1=CC=CC(Cl)=C1Cl OAKDGTOSZQSIDS-UHFFFAOYSA-N 0.000 claims 1
FGLNHXKNBBFDTO-DEOSSOPVSA-N 5-o-[2-[4-(2-hydroxyethyl)phenoxy]ethyl] 3-o-methyl (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1([C@@H]2C(=C(C)NC(C)=C2C(=O)OC)C(=O)OCCOC=2C=CC(CCO)=CC=2)=CC=CC([N+]([O-])=O)=C1 FGLNHXKNBBFDTO-DEOSSOPVSA-N 0.000 claims 1
XUOCEPUPMRAZIJ-UHFFFAOYSA-N 5-o-[2-[4-(2-hydroxypropyl)phenoxy]ethyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC=2C=CC(CC(C)O)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 XUOCEPUPMRAZIJ-UHFFFAOYSA-N 0.000 claims 1
JLTPSXUZMJJPCA-KKFPZRRJSA-N 5-o-[2-[4-(2-methoxypropyl)phenoxy]ethyl] 3-o-methyl (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CC(C)OC)=CC=C1OCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 JLTPSXUZMJJPCA-KKFPZRRJSA-N 0.000 claims 1
JLTPSXUZMJJPCA-UHFFFAOYSA-N 5-o-[2-[4-(2-methoxypropyl)phenoxy]ethyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CC(C)OC)=CC=C1OCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 JLTPSXUZMJJPCA-UHFFFAOYSA-N 0.000 claims 1
XUNMSVXQNSJKTD-UHFFFAOYSA-N 5-o-[2-[4-[2-(cyclohexyloxymethoxy)ethyl]phenoxy]ethyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC=2C=CC(CCOCOC3CCCCC3)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 XUNMSVXQNSJKTD-UHFFFAOYSA-N 0.000 claims 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
229960005335 propanol Drugs 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 120
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 68
238000006243 chemical reaction Methods 0.000 description 53
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
239000000243 solution Substances 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
229910001868 water Inorganic materials 0.000 description 32
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
239000002585 base Substances 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
238000012360 testing method Methods 0.000 description 19
239000000543 intermediate Substances 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
238000004519 manufacturing process Methods 0.000 description 15
RKSLCFPZGOQVMW-UHFFFAOYSA-N 3-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]propyl 3-oxobutanoate Chemical compound C1=CC(OCCCOC(=O)CC(=O)C)=CC=C1CCOC1OCCCC1 RKSLCFPZGOQVMW-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
PVZHUWSNINUEJJ-UHFFFAOYSA-N 4-[2-(oxan-2-yloxy)ethyl]phenol Chemical compound C1=CC(O)=CC=C1CCOC1OCCCC1 PVZHUWSNINUEJJ-UHFFFAOYSA-N 0.000 description 13
JPXPPUOCSLMCHK-UHFFFAOYSA-N 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid Chemical compound COC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 JPXPPUOCSLMCHK-UHFFFAOYSA-N 0.000 description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
239000000047 product Substances 0.000 description 13
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
230000036772 blood pressure Effects 0.000 description 11
RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 10
AEHPROFRJZEEPF-UHFFFAOYSA-N 5-methoxycarbonyl-1-(2-methoxyethoxymethyl)-2,6-dimethyl-4-(3-nitrophenyl)-4h-pyridine-3-carboxylic acid Chemical compound COC(=O)C1=C(C)N(COCCOC)C(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 AEHPROFRJZEEPF-UHFFFAOYSA-N 0.000 description 10
241000282472 Canis lupus familiaris Species 0.000 description 10
235000019439 ethyl acetate Nutrition 0.000 description 10
210000002216 heart Anatomy 0.000 description 10
239000003921 oil Substances 0.000 description 10
235000019198 oils Nutrition 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
241001465754 Metazoa Species 0.000 description 9
241000700159 Rattus Species 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
235000010755 mineral Nutrition 0.000 description 9
MFDGPQJXANCIQM-UHFFFAOYSA-N 3-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]propan-1-ol Chemical compound C1=CC(OCCCO)=CC=C1CCOC1OCCCC1 MFDGPQJXANCIQM-UHFFFAOYSA-N 0.000 description 8
ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 8
208000024172 Cardiovascular disease Diseases 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
201000010099 disease Diseases 0.000 description 8
239000013067 intermediate product Substances 0.000 description 8
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
206010020772 Hypertension Diseases 0.000 description 7
241000124008 Mammalia Species 0.000 description 7
230000003197 catalytic effect Effects 0.000 description 7
238000002474 experimental method Methods 0.000 description 7
238000001990 intravenous administration Methods 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
YCCILVSKPBXVIP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=C(O)C=C1 YCCILVSKPBXVIP-UHFFFAOYSA-N 0.000 description 6
JCUJAHLWCDISCC-UHFFFAOYSA-N 2-(4-phenylmethoxyphenyl)ethanol Chemical compound C1=CC(CCO)=CC=C1OCC1=CC=CC=C1 JCUJAHLWCDISCC-UHFFFAOYSA-N 0.000 description 6
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
MCIAPXKGANXQCE-UHFFFAOYSA-N 5-o-(3-bromopropyl) 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCBr)C1C1=CC=CC([N+]([O-])=O)=C1 MCIAPXKGANXQCE-UHFFFAOYSA-N 0.000 description 6
JPXPPUOCSLMCHK-CQSZACIVSA-N 76093-33-9 Chemical compound COC(=O)C1=C(C)NC(C)=C(C(O)=O)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 JPXPPUOCSLMCHK-CQSZACIVSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
206010002383 Angina Pectoris Diseases 0.000 description 6
206010007559 Cardiac failure congestive Diseases 0.000 description 6
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 6
206010019280 Heart failures Diseases 0.000 description 6
208000019695 Migraine disease Diseases 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
238000003818 flash chromatography Methods 0.000 description 6
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
NKSXDMWAVIOSTD-PLNGDYQASA-N methyl (z)-3-aminopent-2-enoate Chemical compound CC\C(N)=C\C(=O)OC NKSXDMWAVIOSTD-PLNGDYQASA-N 0.000 description 6
206010027599 migraine Diseases 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
230000002455 vasospastic effect Effects 0.000 description 6
FHSUFDYFOHSYHI-UHFFFAOYSA-N 3-oxopentanoic acid Chemical compound CCC(=O)CC(O)=O FHSUFDYFOHSYHI-UHFFFAOYSA-N 0.000 description 5
PVYKGJCGTZQNJL-UHFFFAOYSA-N 5-o-(2-cyanoethyl) 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCC#N)C1C1=CC=CC([N+]([O-])=O)=C1 PVYKGJCGTZQNJL-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 5
229940073608 benzyl chloride Drugs 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
230000037396 body weight Effects 0.000 description 5
238000001816 cooling Methods 0.000 description 5
208000035475 disorder Diseases 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
210000001105 femoral artery Anatomy 0.000 description 5
XKORCTIIRYKLLG-ARJAWSKDSA-N methyl (z)-3-aminobut-2-enoate Chemical compound COC(=O)\C=C(\C)N XKORCTIIRYKLLG-ARJAWSKDSA-N 0.000 description 5
OWZKPLVEECROKR-UHFFFAOYSA-N methyl 2-(4-benzylsulfanylphenyl)acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1SCC1=CC=CC=C1 OWZKPLVEECROKR-UHFFFAOYSA-N 0.000 description 5
OUWFDISHMBDYON-UHFFFAOYSA-N methyl 2-(4-phenylmethoxyphenyl)acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1OCC1=CC=CC=C1 OUWFDISHMBDYON-UHFFFAOYSA-N 0.000 description 5
XJMIXEAZMCTAGH-UHFFFAOYSA-N methyl 3-oxopentanoate Chemical compound CCC(=O)CC(=O)OC XJMIXEAZMCTAGH-UHFFFAOYSA-N 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
238000010898 silica gel chromatography Methods 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
238000011699 spontaneously hypertensive rat Methods 0.000 description 5
AEHPROFRJZEEPF-GOSISDBHSA-N (4r)-5-methoxycarbonyl-1-(2-methoxyethoxymethyl)-2,6-dimethyl-4-(3-nitrophenyl)-4h-pyridine-3-carboxylic acid Chemical compound COC(=O)C1=C(C)N(COCCOC)C(C)=C(C(O)=O)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 AEHPROFRJZEEPF-GOSISDBHSA-N 0.000 description 4
RVYLMWSYBFGEPI-UHFFFAOYSA-N 2-[2-(4-phenylmethoxyphenyl)ethoxy]oxane Chemical compound C1CCCOC1OCCC(C=C1)=CC=C1OCC1=CC=CC=C1 RVYLMWSYBFGEPI-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000000010 aprotic solvent Substances 0.000 description 4
244000309464 bull Species 0.000 description 4
239000013078 crystal Substances 0.000 description 4
150000005690 diesters Chemical class 0.000 description 4
125000005594 diketone group Chemical group 0.000 description 4
LJCISGNCQACFPK-UHFFFAOYSA-N dimethyl 1-(2-methoxyethoxymethyl)-2,6-dimethyl-4-(3-nitrophenyl)-4h-pyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)N(COCCOC)C(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 LJCISGNCQACFPK-UHFFFAOYSA-N 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
238000005259 measurement Methods 0.000 description 4
235000006408 oxalic acid Nutrition 0.000 description 4
239000007787 solid Substances 0.000 description 4
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 4
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
BIAAQBNMRITRDV-UHFFFAOYSA-N 1-(chloromethoxy)-2-methoxyethane Chemical compound COCCOCCl BIAAQBNMRITRDV-UHFFFAOYSA-N 0.000 description 3
MFNFLRNYARCUKB-UHFFFAOYSA-N 1-(ethoxymethyl)-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-4h-pyridine-3-carboxylic acid Chemical compound COC(=O)C1=C(C)N(COCC)C(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 MFNFLRNYARCUKB-UHFFFAOYSA-N 0.000 description 3
LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 3
SWJVFAOGXDGTCX-UHFFFAOYSA-N 2-cyanoethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCC#N SWJVFAOGXDGTCX-UHFFFAOYSA-N 0.000 description 3
ABOLDLATEBBQHP-UHFFFAOYSA-N 3-o-methyl 5-o-[3-[4-[3-(oxan-2-yloxy)propyl]phenoxy]propyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCCOC3OCCCC3)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ABOLDLATEBBQHP-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
238000003512 Claisen condensation reaction Methods 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 0.000 description 3
239000007832 Na2SO4 Substances 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 3
238000005903 acid hydrolysis reaction Methods 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 3
125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 3
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 3
MCTRZKAKODSRLQ-UHFFFAOYSA-N dimethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 MCTRZKAKODSRLQ-UHFFFAOYSA-N 0.000 description 3
239000000284 extract Substances 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
150000002431 hydrogen Chemical group 0.000 description 3
239000011630 iodine Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
210000005240 left ventricle Anatomy 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
230000035488 systolic blood pressure Effects 0.000 description 3
239000003826 tablet Substances 0.000 description 3
239000003981 vehicle Substances 0.000 description 3
NCXUNZWLEYGQAH-UHFFFAOYSA-N 1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C NCXUNZWLEYGQAH-UHFFFAOYSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
LLMLNAVBOAMOEE-UHFFFAOYSA-N 2,3-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1Cl LLMLNAVBOAMOEE-UHFFFAOYSA-N 0.000 description 2
ZDVRPKUWYQVVDX-UHFFFAOYSA-N 2-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC=C1C=O ZDVRPKUWYQVVDX-UHFFFAOYSA-N 0.000 description 2
YEOOIZLPTYZLGX-UHFFFAOYSA-N 2-[2-(oxan-2-yloxy)ethyl]phenol Chemical compound OC1=CC=CC=C1CCOC1OCCCC1 YEOOIZLPTYZLGX-UHFFFAOYSA-N 0.000 description 2
DTRXZMDNTIUOAP-UHFFFAOYSA-N 2-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1CCOC1OCCCC1 DTRXZMDNTIUOAP-UHFFFAOYSA-N 0.000 description 2
YPZLMCNIWFWEBA-UHFFFAOYSA-N 2-[4-[3-(oxan-2-yloxy)propyl]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1CCCOC1OCCCC1 YPZLMCNIWFWEBA-UHFFFAOYSA-N 0.000 description 2
FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 2
ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 description 2
CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 2
238000011265 2D-echocardiography Methods 0.000 description 2
AMQIPHZFLIDOCB-UHFFFAOYSA-N 3-(2-hydroxyethyl)phenol Chemical compound OCCC1=CC=CC(O)=C1 AMQIPHZFLIDOCB-UHFFFAOYSA-N 0.000 description 2
YRMMRFLLVQRRJO-UHFFFAOYSA-N 3-[2-(oxan-2-yloxy)ethyl]phenol Chemical compound OC1=CC=CC(CCOC2OCCCC2)=C1 YRMMRFLLVQRRJO-UHFFFAOYSA-N 0.000 description 2
AGDZIWOTVMDDOY-UHFFFAOYSA-N 3-[4-[3-(oxan-2-yloxy)propyl]phenoxy]propan-1-ol Chemical compound C1=CC(OCCCO)=CC=C1CCCOC1OCCCC1 AGDZIWOTVMDDOY-UHFFFAOYSA-N 0.000 description 2
RWLOGDCTAOXYSC-UHFFFAOYSA-N 3-[4-[4-(oxan-2-yloxy)butyl]phenoxy]propan-1-ol Chemical compound C1=CC(OCCCO)=CC=C1CCCCOC1OCCCC1 RWLOGDCTAOXYSC-UHFFFAOYSA-N 0.000 description 2
SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 2
PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 description 2
WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 2
MAJSRDOAODSUCV-UHFFFAOYSA-N 3-o-methyl 5-o-[3-[4-[4-(oxan-2-yloxy)butyl]phenoxy]propyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCCCOC3OCCCC3)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 MAJSRDOAODSUCV-UHFFFAOYSA-N 0.000 description 2
SIJLYRDVTMMSIP-UHFFFAOYSA-N 4-Bromo-1-butanol Chemical compound OCCCCBr SIJLYRDVTMMSIP-UHFFFAOYSA-N 0.000 description 2
YBAHFHDLTYEIFA-UHFFFAOYSA-N 4-[4-(oxan-2-yloxy)butyl]phenol Chemical compound C1=CC(O)=CC=C1CCCCOC1OCCCC1 YBAHFHDLTYEIFA-UHFFFAOYSA-N 0.000 description 2
ACTWKWFBZDKRLC-UHFFFAOYSA-N 4-[4-[3-(oxan-2-yloxy)propyl]phenoxy]butan-1-ol Chemical compound C1=CC(OCCCCO)=CC=C1CCCOC1OCCCC1 ACTWKWFBZDKRLC-UHFFFAOYSA-N 0.000 description 2
QMHMFHOPOGGVOB-UHFFFAOYSA-N 4-[4-[4-(oxan-2-yloxy)butyl]phenoxy]butan-1-ol Chemical compound C1=CC(OCCCCO)=CC=C1CCCCOC1OCCCC1 QMHMFHOPOGGVOB-UHFFFAOYSA-N 0.000 description 2
150000008091 4-phenyl-1,4-dihydropyridines Chemical class 0.000 description 2
QIPUKTRPPCDOBN-UHFFFAOYSA-N 5-o-[3-[4-(3-hydroxypropyl)phenoxy]propyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 QIPUKTRPPCDOBN-UHFFFAOYSA-N 0.000 description 2
OWNSPNYTPGSMIX-UHFFFAOYSA-N 5-o-[3-[4-(4-hydroxybutyl)phenoxy]propyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 OWNSPNYTPGSMIX-UHFFFAOYSA-N 0.000 description 2
GMXIEASXPUEOTG-UHFFFAOYSA-N 8-bromooctan-1-ol Chemical compound OCCCCCCCCBr GMXIEASXPUEOTG-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
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 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 2
BVBSGGBDFJUSIH-UHFFFAOYSA-N Methyl (2-hydroxyphenyl)acetate Chemical compound COC(=O)CC1=CC=CC=C1O BVBSGGBDFJUSIH-UHFFFAOYSA-N 0.000 description 2
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
206010039424 Salivary hypersecretion Diseases 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
210000000709 aorta Anatomy 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
230000004872 arterial blood pressure Effects 0.000 description 2
150000003935 benzaldehydes Chemical class 0.000 description 2
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 2
230000017531 blood circulation Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 2
PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
210000005242 cardiac chamber Anatomy 0.000 description 2
210000001715 carotid artery Anatomy 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
229940126214 compound 3 Drugs 0.000 description 2
208000027744 congestion Diseases 0.000 description 2
230000008602 contraction Effects 0.000 description 2
210000004351 coronary vessel Anatomy 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000035487 diastolic blood pressure Effects 0.000 description 2
230000003205 diastolic effect Effects 0.000 description 2
OZFPNYCEAKMAOL-UHFFFAOYSA-N dimethyl 1-(ethoxymethyl)-2,6-dimethyl-4-(3-nitrophenyl)-4h-pyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)N(COCC)C(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 OZFPNYCEAKMAOL-UHFFFAOYSA-N 0.000 description 2
231100000673 dose–response relationship Toxicity 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
238000006266 etherification reaction Methods 0.000 description 2
FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
230000001631 hypertensive effect Effects 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
XGDZEDRBLVIUMX-UHFFFAOYSA-N methyl 2-(4-hydroxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(O)C=C1 XGDZEDRBLVIUMX-UHFFFAOYSA-N 0.000 description 2
NVQIKIDABBHFGT-UHFFFAOYSA-N methyl 2-(4-sulfanylphenyl)acetate Chemical compound COC(=O)CC1=CC=C(S)C=C1 NVQIKIDABBHFGT-UHFFFAOYSA-N 0.000 description 2
RZGRWVULDSXQSM-UHFFFAOYSA-N methyl 2-thiophen-3-ylacetate Chemical compound COC(=O)CC=1C=CSC=1 RZGRWVULDSXQSM-UHFFFAOYSA-N 0.000 description 2
HNBDRPTVWVGKBR-UHFFFAOYSA-N methyl pentanoate Chemical compound CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 2
229940017219 methyl propionate Drugs 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 description 2
229960001412 pentobarbital Drugs 0.000 description 2
SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 2
229960001802 phenylephrine Drugs 0.000 description 2
229920000136 polysorbate Polymers 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000009467 reduction Effects 0.000 description 2
208000026451 salivation Diseases 0.000 description 2
238000000926 separation method Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
QGMRQYFBGABWDR-UHFFFAOYSA-N sodium;5-ethyl-5-pentan-2-yl-1,3-diazinane-2,4,6-trione Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)NC1=O QGMRQYFBGABWDR-UHFFFAOYSA-N 0.000 description 2
125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
239000000725 suspension Substances 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
UKVYVZLTGQVOPX-IHWYPQMZSA-N (z)-3-aminobut-2-enoic acid Chemical compound C\C(N)=C\C(O)=O UKVYVZLTGQVOPX-IHWYPQMZSA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
VHUQXPJHMISKGS-UHFFFAOYSA-N 1-(chloromethoxy)propane Chemical compound CCCOCCl VHUQXPJHMISKGS-UHFFFAOYSA-N 0.000 description 1
ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
KOZZVNSEJLFMJW-UHFFFAOYSA-N 2-(2-hydroxyphenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=CC=CC=C1O KOZZVNSEJLFMJW-UHFFFAOYSA-N 0.000 description 1
ABFCOJLLBHXNOU-UHFFFAOYSA-N 2-(2-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=CC=C1O ABFCOJLLBHXNOU-UHFFFAOYSA-N 0.000 description 1
KAMXYCVETYXNSB-UHFFFAOYSA-N 2-(2-phenylmethoxyphenyl)ethanol Chemical compound OCCC1=CC=CC=C1OCC1=CC=CC=C1 KAMXYCVETYXNSB-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
GUZQNHDLUAULGY-UHFFFAOYSA-N 2-(3-hydroxyphenyl)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)C1=CC=CC(O)=C1 GUZQNHDLUAULGY-UHFFFAOYSA-N 0.000 description 1
RHHVCIKVRLMNFC-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)ethanol Chemical compound OCCC1=CC=CC(OCC=2C=CC=CC=2)=C1 RHHVCIKVRLMNFC-UHFFFAOYSA-N 0.000 description 1
PECVBUCAGSDWKQ-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)C1=CC=C(O)C=C1 PECVBUCAGSDWKQ-UHFFFAOYSA-N 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
WHAZIISQZLDQBK-UHFFFAOYSA-N 2-[2-[2-(oxan-2-yloxy)ethyl]phenoxy]ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC1=CC=CC=C1CCOC1OCCCC1 WHAZIISQZLDQBK-UHFFFAOYSA-N 0.000 description 1
DETPKOCZXJTNTI-UHFFFAOYSA-N 2-[2-[3-(oxan-2-yloxy)propyl]phenoxy]ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC1=CC=CC=C1CCCOC1OCCCC1 DETPKOCZXJTNTI-UHFFFAOYSA-N 0.000 description 1
YYRKLPARYKZMEY-UHFFFAOYSA-N 2-[2-[4-(oxan-2-yloxy)butyl]phenoxy]ethanol Chemical compound OCCOC1=CC=CC=C1CCCCOC1OCCCC1 YYRKLPARYKZMEY-UHFFFAOYSA-N 0.000 description 1
OQKBJYBNYCAODT-UHFFFAOYSA-N 2-[2-[4-(oxan-2-yloxy)butyl]phenoxy]ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC1=CC=CC=C1CCCCOC1OCCCC1 OQKBJYBNYCAODT-UHFFFAOYSA-N 0.000 description 1
SJYHRDCIUSEWBV-UHFFFAOYSA-N 2-[3-[2-(oxan-2-yloxy)ethyl]phenoxy]ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC1=CC=CC(CCOC2OCCCC2)=C1 SJYHRDCIUSEWBV-UHFFFAOYSA-N 0.000 description 1
XFNURXBBDYBOEQ-UHFFFAOYSA-N 2-[3-[2-(oxan-2-yloxy)ethyl]phenyl]sulfanylethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCSC1=CC=CC(CCOC2OCCCC2)=C1 XFNURXBBDYBOEQ-UHFFFAOYSA-N 0.000 description 1
JLWPZDXCMWNDNG-UHFFFAOYSA-N 2-[3-[3-(oxan-2-yloxy)propyl]phenoxy]ethanol Chemical compound OCCOC1=CC=CC(CCCOC2OCCCC2)=C1 JLWPZDXCMWNDNG-UHFFFAOYSA-N 0.000 description 1
WYBTYMQUQLODSO-UHFFFAOYSA-N 2-[3-[3-(oxan-2-yloxy)propyl]phenoxy]ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC1=CC=CC(CCCOC2OCCCC2)=C1 WYBTYMQUQLODSO-UHFFFAOYSA-N 0.000 description 1
WGHXZGFFVWSQCC-UHFFFAOYSA-N 2-[3-[4-(oxan-2-yloxy)butyl]phenoxy]ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC1=CC=CC(CCCCOC2OCCCC2)=C1 WGHXZGFFVWSQCC-UHFFFAOYSA-N 0.000 description 1
LWKKCPIDGXLSTG-UHFFFAOYSA-N 2-[4-(oxan-2-yloxy)butyl]phenol Chemical compound OC1=CC=CC=C1CCCCOC1OCCCC1 LWKKCPIDGXLSTG-UHFFFAOYSA-N 0.000 description 1
CMCNAQXVBBSIAA-UHFFFAOYSA-N 2-[4-[3-(oxan-2-yloxy)propyl]phenoxy]ethyl 3-oxobutanoate Chemical compound C1=CC(OCCOC(=O)CC(=O)C)=CC=C1CCCOC1OCCCC1 CMCNAQXVBBSIAA-UHFFFAOYSA-N 0.000 description 1
FTDHKEVFMYUOAJ-UHFFFAOYSA-N 2-[4-[3-(oxan-2-yloxy)propyl]phenoxy]ethyl 3-oxopentanoate Chemical compound C1=CC(OCCOC(=O)CC(=O)CC)=CC=C1CCCOC1OCCCC1 FTDHKEVFMYUOAJ-UHFFFAOYSA-N 0.000 description 1
ZJJLLFCTVPDZDE-UHFFFAOYSA-N 2-[4-[4-(oxan-2-yloxy)butyl]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1CCCCOC1OCCCC1 ZJJLLFCTVPDZDE-UHFFFAOYSA-N 0.000 description 1
XNDUCILBQZUJPI-UHFFFAOYSA-N 2-[4-[4-(oxan-2-yloxy)butyl]phenoxy]ethyl 3-oxobutanoate Chemical compound C1=CC(OCCOC(=O)CC(=O)C)=CC=C1CCCCOC1OCCCC1 XNDUCILBQZUJPI-UHFFFAOYSA-N 0.000 description 1
DNPCTGQCQKYTEP-UHFFFAOYSA-N 2-[4-[4-(oxan-2-yloxy)butyl]phenoxy]ethyl 3-oxopentanoate Chemical compound C1=CC(OCCOC(=O)CC(=O)CC)=CC=C1CCCCOC1OCCCC1 DNPCTGQCQKYTEP-UHFFFAOYSA-N 0.000 description 1
QPWQYDYDLGGVMY-UHFFFAOYSA-N 2-[4-[4-(oxan-2-yloxy)butyl]phenyl]sulfanylethyl 3-oxobutanoate Chemical compound C1=CC(SCCOC(=O)CC(=O)C)=CC=C1CCCCOC1OCCCC1 QPWQYDYDLGGVMY-UHFFFAOYSA-N 0.000 description 1
DWMRWBNFBDLXNM-UHFFFAOYSA-N 2-methoxyethyl 3-aminohept-2-enoate Chemical compound CCCCC(N)=CC(=O)OCCOC DWMRWBNFBDLXNM-UHFFFAOYSA-N 0.000 description 1
JDTLZFIOPCOQAA-UHFFFAOYSA-N 2-methoxyethyl 3-aminohex-2-enoate Chemical compound CCCC(N)=CC(=O)OCCOC JDTLZFIOPCOQAA-UHFFFAOYSA-N 0.000 description 1
SMOVCAQTHZDQRD-UHFFFAOYSA-N 2-methoxyethyl 3-aminopent-2-enoate Chemical compound CCC(N)=CC(=O)OCCOC SMOVCAQTHZDQRD-UHFFFAOYSA-N 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
RCNOGGGBSSVMAS-UHFFFAOYSA-N 2-thiophen-3-ylacetic acid Chemical compound OC(=O)CC=1C=CSC=1 RCNOGGGBSSVMAS-UHFFFAOYSA-N 0.000 description 1
ZJJFPIKMLKBRLY-UHFFFAOYSA-N 3-(3-phenylmethoxyphenyl)propan-1-ol Chemical compound OCCCC1=CC=CC(OCC=2C=CC=CC=2)=C1 ZJJFPIKMLKBRLY-UHFFFAOYSA-N 0.000 description 1
NJCVPQRHRKYSAZ-UHFFFAOYSA-N 3-(4-Hydroxyphenyl)-1-propanol Chemical compound OCCCC1=CC=C(O)C=C1 NJCVPQRHRKYSAZ-UHFFFAOYSA-N 0.000 description 1
FZALPKMIIYFLAP-UHFFFAOYSA-N 3-(4-phenylmethoxyphenyl)propan-1-ol Chemical compound C1=CC(CCCO)=CC=C1OCC1=CC=CC=C1 FZALPKMIIYFLAP-UHFFFAOYSA-N 0.000 description 1
BLMVSXRDIORXER-UHFFFAOYSA-N 3-O-(2-methoxyethyl) 5-O-[2-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]ethyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC=1NC(=C(C(C1C(=O)OCCOC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCOC1=CC=C(C=C1)CCOC1OCCCC1)C BLMVSXRDIORXER-UHFFFAOYSA-N 0.000 description 1
MVEBPTYOLGTKPP-UHFFFAOYSA-N 3-[2-[2-(oxan-2-yloxy)ethyl]phenoxy]propan-1-ol Chemical compound OCCCOC1=CC=CC=C1CCOC1OCCCC1 MVEBPTYOLGTKPP-UHFFFAOYSA-N 0.000 description 1
XAXLXEAFUMMZAY-UHFFFAOYSA-N 3-[2-[3-(oxan-2-yloxy)propyl]phenoxy]propyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCOC1=CC=CC=C1CCCOC1OCCCC1 XAXLXEAFUMMZAY-UHFFFAOYSA-N 0.000 description 1
KIWDSSSRYCFFAP-UHFFFAOYSA-N 3-[2-[4-(oxan-2-yloxy)butyl]phenoxy]propyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCOC1=CC=CC=C1CCCCOC1OCCCC1 KIWDSSSRYCFFAP-UHFFFAOYSA-N 0.000 description 1
QNULXJHGQWCZPZ-UHFFFAOYSA-N 3-[3-(oxan-2-yloxy)propyl]phenol Chemical compound OC1=CC=CC(CCCOC2OCCCC2)=C1 QNULXJHGQWCZPZ-UHFFFAOYSA-N 0.000 description 1
PKQQFLASVNRUKD-UHFFFAOYSA-N 3-[3-[2-(oxan-2-yloxy)ethyl]phenyl]sulfanylpropyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCSC1=CC=CC(CCOC2OCCCC2)=C1 PKQQFLASVNRUKD-UHFFFAOYSA-N 0.000 description 1
SABOWRYVBKXQFE-UHFFFAOYSA-N 3-[3-[2-(oxan-2-yloxy)ethyl]phenyl]sulfanylpropyl 3-oxohexanoate Chemical compound CCCC(=O)CC(=O)OCCCSC1=CC=CC(CCOC2OCCCC2)=C1 SABOWRYVBKXQFE-UHFFFAOYSA-N 0.000 description 1
LXWKYIRSMZGQDB-UHFFFAOYSA-N 3-[3-[2-(oxan-2-yloxy)ethyl]phenyl]sulfanylpropyl 3-oxopentanoate Chemical compound CCC(=O)CC(=O)OCCCSC1=CC=CC(CCOC2OCCCC2)=C1 LXWKYIRSMZGQDB-UHFFFAOYSA-N 0.000 description 1
HWFPNZRSKDEILR-UHFFFAOYSA-N 3-[3-[3-(oxan-2-yloxy)propyl]phenoxy]propyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCOC1=CC=CC(CCCOC2OCCCC2)=C1 HWFPNZRSKDEILR-UHFFFAOYSA-N 0.000 description 1
HAYGOFHNSOSVFG-UHFFFAOYSA-N 3-[3-[4-(oxan-2-yloxy)butyl]phenoxy]propyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCOC1=CC=CC(CCCCOC2OCCCC2)=C1 HAYGOFHNSOSVFG-UHFFFAOYSA-N 0.000 description 1
PFWJUMUEBRMOQR-UHFFFAOYSA-N 3-[4-[2-(oxan-2-yloxy)ethyl]phenyl]sulfanylpropyl 3-oxohexanoate Chemical compound C1=CC(SCCCOC(=O)CC(=O)CCC)=CC=C1CCOC1OCCCC1 PFWJUMUEBRMOQR-UHFFFAOYSA-N 0.000 description 1
CZQCXFALDFWFKO-UHFFFAOYSA-N 3-[4-[8-(oxan-2-yloxy)octyl]phenoxy]propan-1-ol Chemical compound C1=CC(OCCCO)=CC=C1CCCCCCCCOC1OCCCC1 CZQCXFALDFWFKO-UHFFFAOYSA-N 0.000 description 1
MIEKIMPKTSNGRO-UHFFFAOYSA-N 3-[4-[8-(oxan-2-yloxy)octyl]phenoxy]propyl 3-oxobutanoate Chemical compound C1=CC(OCCCOC(=O)CC(=O)C)=CC=C1CCCCCCCCOC1OCCCC1 MIEKIMPKTSNGRO-UHFFFAOYSA-N 0.000 description 1
LIFUJLSSTFGJJV-UHFFFAOYSA-N 3-hydroxypropyl phenylmethanesulfonate Chemical compound OCCCOS(=O)(=O)CC1=CC=CC=C1 LIFUJLSSTFGJJV-UHFFFAOYSA-N 0.000 description 1
QNGNLAJAWWLCNC-UHFFFAOYSA-N 3-o-[2-[4-(2-acetyloxyethyl)phenoxy]ethyl] 5-o-propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC(C)OC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC=2C=CC(CCOC(C)=O)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 QNGNLAJAWWLCNC-UHFFFAOYSA-N 0.000 description 1
UFPCMBFSIUYIOZ-UHFFFAOYSA-N 3-o-[2-[4-(2-butanoyloxyethyl)phenoxy]ethyl] 5-o-propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CCOC(=O)CCC)=CC=C1OCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 UFPCMBFSIUYIOZ-UHFFFAOYSA-N 0.000 description 1
GWNLPCIRUXXJCX-UHFFFAOYSA-N 3-o-[2-[4-(2-hydroxyethyl)phenoxy]ethyl] 5-o-propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC(C)OC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC=2C=CC(CCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 GWNLPCIRUXXJCX-UHFFFAOYSA-N 0.000 description 1
BWTUDVSTIBRYIS-UHFFFAOYSA-N 3-o-[2-[4-(2-hydroxyethyl)phenyl]sulfanylethyl] 5-o-propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC(C)OC(=O)C1=C(C)NC(C)=C(C(=O)OCCSC=2C=CC(CCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 BWTUDVSTIBRYIS-UHFFFAOYSA-N 0.000 description 1
CGSMAXIAYKKZMD-UHFFFAOYSA-N 3-o-[2-[4-(2-propanoyloxyethyl)phenoxy]ethyl] 5-o-propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CCOC(=O)CC)=CC=C1OCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 CGSMAXIAYKKZMD-UHFFFAOYSA-N 0.000 description 1
QRCDCXNXIKYHQI-UHFFFAOYSA-N 3-o-[2-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]ethyl] 5-o-propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC(C)OC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC=2C=CC(CCOC3OCCCC3)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 QRCDCXNXIKYHQI-UHFFFAOYSA-N 0.000 description 1
BGIFLUJKJVQQDK-UHFFFAOYSA-N 3-o-[3-[4-(2-hydroxyethyl)phenoxy]propyl] 5-o-methyl 2-ethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(CC)=C(C(=O)OCCCOC=2C=CC(CCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 BGIFLUJKJVQQDK-UHFFFAOYSA-N 0.000 description 1
FNDDUPXMYNHFSL-UHFFFAOYSA-N 3-o-[3-[4-(2-hydroxyethyl)phenyl]sulfanylpropyl] 5-o-methyl 2-ethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(CC)=C(C(=O)OCCCSC=2C=CC(CCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 FNDDUPXMYNHFSL-UHFFFAOYSA-N 0.000 description 1
MIWPJLIJPGGQID-UHFFFAOYSA-N 3-o-[3-[4-(3-hydroxypropyl)phenoxy]propyl] 5-o-methyl 2-ethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(CC)=C(C(=O)OCCCOC=2C=CC(CCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 MIWPJLIJPGGQID-UHFFFAOYSA-N 0.000 description 1
APSHZPFNLCNDBI-UHFFFAOYSA-N 3-o-[3-[4-(3-hydroxypropyl)phenyl]sulfanylpropyl] 5-o-methyl 2-ethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(CC)=C(C(=O)OCCCSC=2C=CC(CCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 APSHZPFNLCNDBI-UHFFFAOYSA-N 0.000 description 1
OHRPENRBHOIEKE-UHFFFAOYSA-N 3-o-[3-[4-(4-hydroxybutyl)phenyl]sulfanylpropyl] 5-o-methyl 2-ethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(CC)=C(C(=O)OCCCSC=2C=CC(CCCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 OHRPENRBHOIEKE-UHFFFAOYSA-N 0.000 description 1
ZHLOJGQMIMRIOL-UHFFFAOYSA-N 3-o-butyl 5-o-[3-[4-(2-hydroxyethyl)phenoxy]propyl] 2-ethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCCCOC(=O)C1=C(CC)NC(C)=C(C(=O)OCCCOC=2C=CC(CCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZHLOJGQMIMRIOL-UHFFFAOYSA-N 0.000 description 1
LZHYXAONAYWIKZ-UHFFFAOYSA-N 3-o-ethyl 5-o-[3-[4-(3-hydroxypropyl)phenoxy]propyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 LZHYXAONAYWIKZ-UHFFFAOYSA-N 0.000 description 1
XBZDDUIBTNYABX-UHFFFAOYSA-N 3-o-ethyl 5-o-[3-[4-(4-hydroxybutyl)phenoxy]propyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 XBZDDUIBTNYABX-UHFFFAOYSA-N 0.000 description 1
ANYVMIMJZDZCDR-UHFFFAOYSA-N 3-o-ethyl 5-o-[3-[4-(4-hydroxybutyl)phenyl]sulfanylpropyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCCSC=2C=CC(CCCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ANYVMIMJZDZCDR-UHFFFAOYSA-N 0.000 description 1
KEHMZPMYYJYFAN-UHFFFAOYSA-N 3-o-ethyl 5-o-[3-[4-[4-(oxan-2-yloxy)butyl]phenyl]sulfanylpropyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCCSC=2C=CC(CCCCOC3OCCCC3)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 KEHMZPMYYJYFAN-UHFFFAOYSA-N 0.000 description 1
IJQWSFITMJTYEB-UHFFFAOYSA-N 3-o-methyl 5-o-[2-[4-[3-(oxan-2-yloxy)propyl]phenoxy]ethyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC=2C=CC(CCCOC3OCCCC3)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 IJQWSFITMJTYEB-UHFFFAOYSA-N 0.000 description 1
LWRRUESKMFCDOQ-UHFFFAOYSA-N 3-o-methyl 5-o-[2-[4-[3-(oxan-2-yloxy)propyl]phenyl]sulfanylethyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCSC=2C=CC(CCCOC3OCCCC3)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 LWRRUESKMFCDOQ-UHFFFAOYSA-N 0.000 description 1
TZQHUOAOFVUOAE-UHFFFAOYSA-N 3-o-methyl 5-o-[2-[4-[4-(oxan-2-yloxy)butyl]phenyl]sulfanylethyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCSC=2C=CC(CCCCOC3OCCCC3)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 TZQHUOAOFVUOAE-UHFFFAOYSA-N 0.000 description 1
QNLTXRWFNAOMRP-UHFFFAOYSA-N 3-o-methyl 5-o-[3-[4-(2-propanoyloxyethyl)phenoxy]propyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CCOC(=O)CC)=CC=C1OCCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 QNLTXRWFNAOMRP-UHFFFAOYSA-N 0.000 description 1
HMFNYZJQQSDJSF-UHFFFAOYSA-N 3-o-methyl 5-o-[3-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]propyl] 4-(2-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCOC3OCCCC3)=CC=2)C1C1=CC=CC=C1Cl HMFNYZJQQSDJSF-UHFFFAOYSA-N 0.000 description 1
BHTCUDIOCLZHBE-UHFFFAOYSA-N 3-o-methyl 5-o-[3-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]propyl] 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCOC3OCCCC3)=CC=2)C1C1=CC=CC(Cl)=C1 BHTCUDIOCLZHBE-UHFFFAOYSA-N 0.000 description 1
HMATUJYRUVQZPH-UHFFFAOYSA-N 3-o-methyl 5-o-[3-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]propyl] 4-(3-fluorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCOC3OCCCC3)=CC=2)C1C1=CC=CC(F)=C1 HMATUJYRUVQZPH-UHFFFAOYSA-N 0.000 description 1
NHZSOODBMDJXIB-UHFFFAOYSA-N 3-o-methyl 5-o-[3-[4-[2-(oxan-2-yloxy)ethyl]phenyl]propyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCC=2C=CC(CCOC3OCCCC3)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 NHZSOODBMDJXIB-UHFFFAOYSA-N 0.000 description 1
LLQIFRXMNLZSRY-UHFFFAOYSA-N 3-o-methyl 5-o-[3-[4-[2-(oxan-2-yloxy)ethyl]phenyl]sulfanylpropyl] 2,6-diethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCC=1NC(CC)=C(C(=O)OC)C(C=2C=C(C=CC=2)[N+]([O-])=O)C=1C(=O)OCCCSC(C=C1)=CC=C1CCOC1CCCCO1 LLQIFRXMNLZSRY-UHFFFAOYSA-N 0.000 description 1
USEYWIBMTKYFBX-LJAQVGFWSA-N 3-o-methyl 5-o-[3-[4-[2-(propoxymethoxy)ethyl]phenoxy]propyl] (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CCOCOCCC)=CC=C1OCCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 USEYWIBMTKYFBX-LJAQVGFWSA-N 0.000 description 1
IEIPLIJTCXQJON-UHFFFAOYSA-N 3-o-methyl 5-o-[3-[4-[3-(oxan-2-yloxy)propyl]phenoxy]propyl] 2-ethyl-4-(3-nitrophenyl)-6-propyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(CC)NC(CCC)=C(C(=O)OCCCOC=2C=CC(CCCOC3OCCCC3)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 IEIPLIJTCXQJON-UHFFFAOYSA-N 0.000 description 1
LNZKUBLESXZGBW-UHFFFAOYSA-N 3-o-methyl 5-o-[4-[4-[3-(oxan-2-yloxy)propyl]phenyl]sulfanylbutyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCCSC=2C=CC(CCCOC3OCCCC3)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 LNZKUBLESXZGBW-UHFFFAOYSA-N 0.000 description 1
UYICJHKRHWFKKL-UHFFFAOYSA-N 3-o-methyl 5-o-[4-[4-[4-(oxan-2-yloxy)butyl]phenyl]sulfanylbutyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCCSC=2C=CC(CCCCOC3OCCCC3)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 UYICJHKRHWFKKL-UHFFFAOYSA-N 0.000 description 1
QWEDBUUPMLVCDP-UHFFFAOYSA-N 4-(4-hydroxybutyl)phenol Chemical compound OCCCCC1=CC=C(O)C=C1 QWEDBUUPMLVCDP-UHFFFAOYSA-N 0.000 description 1
WCNQWIWLMNNLSC-UHFFFAOYSA-N 4-(4-phenylmethoxyphenyl)butan-1-ol Chemical compound C1=CC(CCCCO)=CC=C1OCC1=CC=CC=C1 WCNQWIWLMNNLSC-UHFFFAOYSA-N 0.000 description 1
JCYPECIVGRXBMO-UHFFFAOYSA-N 4-(dimethylamino)azobenzene Chemical compound C1=CC(N(C)C)=CC=C1N=NC1=CC=CC=C1 JCYPECIVGRXBMO-UHFFFAOYSA-N 0.000 description 1
RRFXQTWVFQYGJT-UHFFFAOYSA-N 4-(oxan-2-yloxymethyl)phenol Chemical compound C1=CC(O)=CC=C1COC1OCCCC1 RRFXQTWVFQYGJT-UHFFFAOYSA-N 0.000 description 1
JENGJNZEJWIBLW-UHFFFAOYSA-N 4-[2-[2-(oxan-2-yloxy)ethyl]phenoxy]butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCCOC1=CC=CC=C1CCOC1OCCCC1 JENGJNZEJWIBLW-UHFFFAOYSA-N 0.000 description 1
CWEHEHBLHOOROV-UHFFFAOYSA-N 4-[2-[3-(oxan-2-yloxy)propyl]phenoxy]butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCCOC1=CC=CC=C1CCCOC1OCCCC1 CWEHEHBLHOOROV-UHFFFAOYSA-N 0.000 description 1
RJQGHMQMNXINHK-UHFFFAOYSA-N 4-[2-[4-(oxan-2-yloxy)butyl]phenoxy]butan-1-ol Chemical compound OCCCCOC1=CC=CC=C1CCCCOC1OCCCC1 RJQGHMQMNXINHK-UHFFFAOYSA-N 0.000 description 1
HVWFJCCCUPRBOW-UHFFFAOYSA-N 4-[2-[4-(oxan-2-yloxy)butyl]phenoxy]butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCCOC1=CC=CC=C1CCCCOC1OCCCC1 HVWFJCCCUPRBOW-UHFFFAOYSA-N 0.000 description 1
UEXCALVBACNYRW-UHFFFAOYSA-N 4-[3-(oxan-2-yloxy)propyl]phenol Chemical compound C1=CC(O)=CC=C1CCCOC1OCCCC1 UEXCALVBACNYRW-UHFFFAOYSA-N 0.000 description 1
YULGDXDVDWFKMH-UHFFFAOYSA-N 4-[3-[2-(oxan-2-yloxy)ethyl]phenoxy]butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCCOC1=CC=CC(CCOC2OCCCC2)=C1 YULGDXDVDWFKMH-UHFFFAOYSA-N 0.000 description 1
PJAWNYPRXYCREZ-UHFFFAOYSA-N 4-[3-[2-(oxan-2-yloxy)ethyl]phenyl]sulfanylbutyl 3-oxohexanoate Chemical compound CCCC(=O)CC(=O)OCCCCSC1=CC=CC(CCOC2OCCCC2)=C1 PJAWNYPRXYCREZ-UHFFFAOYSA-N 0.000 description 1
FDSDOMQXPXIGHG-UHFFFAOYSA-N 4-[3-[3-(oxan-2-yloxy)propyl]phenoxy]butan-1-ol Chemical compound OCCCCOC1=CC=CC(CCCOC2OCCCC2)=C1 FDSDOMQXPXIGHG-UHFFFAOYSA-N 0.000 description 1
HECMDVZFSQCDEU-UHFFFAOYSA-N 4-[3-[3-(oxan-2-yloxy)propyl]phenoxy]butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCCOC1=CC=CC(CCCOC2OCCCC2)=C1 HECMDVZFSQCDEU-UHFFFAOYSA-N 0.000 description 1
GAZDHQHBRDAHAK-UHFFFAOYSA-N 4-[3-[4-(oxan-2-yloxy)butyl]phenoxy]butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCCOC1=CC=CC(CCCCOC2OCCCC2)=C1 GAZDHQHBRDAHAK-UHFFFAOYSA-N 0.000 description 1
NELKTLZNNNYTCO-UHFFFAOYSA-N 4-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]butan-1-ol Chemical compound C1=CC(OCCCCO)=CC=C1CCOC1OCCCC1 NELKTLZNNNYTCO-UHFFFAOYSA-N 0.000 description 1
YYHWECJKDVJJMC-UHFFFAOYSA-N 4-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]butyl 3-oxobutanoate Chemical compound C1=CC(OCCCCOC(=O)CC(=O)C)=CC=C1CCOC1OCCCC1 YYHWECJKDVJJMC-UHFFFAOYSA-N 0.000 description 1
FBFWVUGFIKSPEQ-UHFFFAOYSA-N 4-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]butyl 3-oxopentanoate Chemical compound C1=CC(OCCCCOC(=O)CC(=O)CC)=CC=C1CCOC1OCCCC1 FBFWVUGFIKSPEQ-UHFFFAOYSA-N 0.000 description 1
SGHUZUARPMEMEO-UHFFFAOYSA-N 4-[4-[2-(oxan-2-yloxy)ethyl]phenyl]sulfanylbutyl 3-oxobutanoate Chemical compound C1=CC(SCCCCOC(=O)CC(=O)C)=CC=C1CCOC1OCCCC1 SGHUZUARPMEMEO-UHFFFAOYSA-N 0.000 description 1
CEJZQLHAAGXPLW-UHFFFAOYSA-N 4-[4-[3-(oxan-2-yloxy)propyl]phenoxy]butyl 3-oxobutanoate Chemical compound C1=CC(OCCCCOC(=O)CC(=O)C)=CC=C1CCCOC1OCCCC1 CEJZQLHAAGXPLW-UHFFFAOYSA-N 0.000 description 1
WMKZOWFLBMLECN-UHFFFAOYSA-N 4-[4-[3-(oxan-2-yloxy)propyl]phenyl]sulfanylbutyl 3-oxobutanoate Chemical compound C1=CC(SCCCCOC(=O)CC(=O)C)=CC=C1CCCOC1OCCCC1 WMKZOWFLBMLECN-UHFFFAOYSA-N 0.000 description 1
APCCRBOCTWBGLX-UHFFFAOYSA-N 4-[4-[4-(oxan-2-yloxy)butyl]phenoxy]butyl 3-oxobutanoate Chemical compound C1=CC(OCCCCOC(=O)CC(=O)C)=CC=C1CCCCOC1OCCCC1 APCCRBOCTWBGLX-UHFFFAOYSA-N 0.000 description 1
JTBIQQOQURWPNK-UHFFFAOYSA-N 4-[4-[8-(oxan-2-yloxy)octyl]phenoxy]butan-1-ol Chemical compound C1=CC(OCCCCO)=CC=C1CCCCCCCCOC1OCCCC1 JTBIQQOQURWPNK-UHFFFAOYSA-N 0.000 description 1
WNJGMJHCEVRMEA-UHFFFAOYSA-N 4-[8-(oxan-2-yloxy)octyl]phenol Chemical compound C1=CC(O)=CC=C1CCCCCCCCOC1OCCCC1 WNJGMJHCEVRMEA-UHFFFAOYSA-N 0.000 description 1
JCAMUKBEZGDUBB-UHFFFAOYSA-N 5-O-[3-[4-[2-(methoxymethoxy)ethyl]phenoxy]propyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC=1NC(=C(C(C1C(=O)OC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCCOC1=CC=C(C=C1)CCOCOC)C JCAMUKBEZGDUBB-UHFFFAOYSA-N 0.000 description 1
LVSQQLVIUOKRDU-UHFFFAOYSA-N 5-O-methyl 3-O-[3-[4-[3-(oxan-2-yloxy)propyl]phenoxy]propyl] 2-ethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC=1NC(=C(C(C=1C(=O)OC)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCCOC1=CC=C(C=C1)CCCOC1OCCCC1)CC LVSQQLVIUOKRDU-UHFFFAOYSA-N 0.000 description 1
KXVNQIGNPGFYBG-UHFFFAOYSA-N 5-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]pentan-1-ol Chemical compound C1=CC(OCCCCCO)=CC=C1CCOC1OCCCC1 KXVNQIGNPGFYBG-UHFFFAOYSA-N 0.000 description 1
WJVQJXVMLRGNGA-UHFFFAOYSA-N 5-bromopentan-1-ol Chemical compound OCCCCCBr WJVQJXVMLRGNGA-UHFFFAOYSA-N 0.000 description 1
NAESRGXBHWECTA-UHFFFAOYSA-N 5-o-(8-bromooctyl) 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCCCCCCBr)C1C1=CC=CC([N+]([O-])=O)=C1 NAESRGXBHWECTA-UHFFFAOYSA-N 0.000 description 1
OJJJAPCGNPLLTM-UHFFFAOYSA-N 5-o-[2-[4-(2-acetyloxyethyl)phenoxy]ethyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC=2C=CC(CCOC(C)=O)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 OJJJAPCGNPLLTM-UHFFFAOYSA-N 0.000 description 1
IJDAFYSHDYABEG-UHFFFAOYSA-N 5-o-[2-[4-(2-hydroxyethyl)phenoxy]ethyl] 3-o-(2-methoxyethyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC=2C=CC(CCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 IJDAFYSHDYABEG-UHFFFAOYSA-N 0.000 description 1
NRZWCBHWPFOTDM-UHFFFAOYSA-N 5-o-[2-[4-(2-hydroxyethyl)phenyl]sulfanylethyl] 3-o-(2-methoxyethyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCSC=2C=CC(CCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 NRZWCBHWPFOTDM-UHFFFAOYSA-N 0.000 description 1
IQWMKHAIRGKHJL-UHFFFAOYSA-N 5-o-[2-[4-(3-hydroxypropyl)phenoxy]ethyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC=2C=CC(CCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 IQWMKHAIRGKHJL-UHFFFAOYSA-N 0.000 description 1
ZKHYIGJNUCLMQB-UHFFFAOYSA-N 5-o-[2-[4-(3-hydroxypropyl)phenyl]sulfanylethyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCSC=2C=CC(CCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZKHYIGJNUCLMQB-UHFFFAOYSA-N 0.000 description 1
FSDHOGOQZOICEZ-UHFFFAOYSA-N 5-o-[2-[4-(4-hydroxybutyl)phenoxy]ethyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCOC=2C=CC(CCCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 FSDHOGOQZOICEZ-UHFFFAOYSA-N 0.000 description 1
DSNIVGWLRZFOQM-UHFFFAOYSA-N 5-o-[2-[4-(4-hydroxybutyl)phenyl]sulfanylethyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCSC=2C=CC(CCCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 DSNIVGWLRZFOQM-UHFFFAOYSA-N 0.000 description 1
NDPGEEBAWDJKEF-UHFFFAOYSA-N 5-o-[3-[4-(2-acetyloxyethyl)phenoxy]propyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCOC(C)=O)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 NDPGEEBAWDJKEF-UHFFFAOYSA-N 0.000 description 1
ZPHZTWMNQBRIBH-UHFFFAOYSA-N 5-o-[3-[4-(2-butanoyloxyethyl)phenoxy]propyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CCOC(=O)CCC)=CC=C1OCCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 ZPHZTWMNQBRIBH-UHFFFAOYSA-N 0.000 description 1
XNFHAEKZDLFCHA-HKBQPEDESA-N 5-o-[3-[4-(2-cyclohexyloxyethyl)phenoxy]propyl] 3-o-methyl (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1([C@@H]2C(=C(C)NC(C)=C2C(=O)OC)C(=O)OCCCOC=2C=CC(CCOC3CCCCC3)=CC=2)=CC=CC([N+]([O-])=O)=C1 XNFHAEKZDLFCHA-HKBQPEDESA-N 0.000 description 1
XNFHAEKZDLFCHA-UHFFFAOYSA-N 5-o-[3-[4-(2-cyclohexyloxyethyl)phenoxy]propyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCOC3CCCCC3)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 XNFHAEKZDLFCHA-UHFFFAOYSA-N 0.000 description 1
SYOYCBKPKYLHMF-UHFFFAOYSA-N 5-o-[3-[4-(2-hydroxyethyl)phenoxy]propyl] 3-o-methyl 2,6-diethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCC=1NC(CC)=C(C(=O)OC)C(C=2C=C(C=CC=2)[N+]([O-])=O)C=1C(=O)OCCCOC1=CC=C(CCO)C=C1 SYOYCBKPKYLHMF-UHFFFAOYSA-N 0.000 description 1
RWIRQZSYQJKEGJ-UHFFFAOYSA-N 5-o-[3-[4-(2-hydroxyethyl)phenoxy]propyl] 3-o-methyl 2-ethyl-4-(3-nitrophenyl)-6-propyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(CC)NC(CCC)=C(C(=O)OCCCOC=2C=CC(CCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 RWIRQZSYQJKEGJ-UHFFFAOYSA-N 0.000 description 1
JRUKUYWFQRKSFC-UHFFFAOYSA-N 5-o-[3-[4-(2-hydroxyethyl)phenoxy]propyl] 3-o-methyl 2-ethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC=1NC(CC)=C(C(=O)OC)C(C=2C=C(C=CC=2)[N+]([O-])=O)C=1C(=O)OCCCOC1=CC=C(CCO)C=C1 JRUKUYWFQRKSFC-UHFFFAOYSA-N 0.000 description 1
DZHIKSUNHRALNT-UHFFFAOYSA-N 5-o-[3-[4-(2-hydroxyethyl)phenoxy]propyl] 3-o-methyl 4-(2-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCO)=CC=2)C1C1=CC=CC=C1Cl DZHIKSUNHRALNT-UHFFFAOYSA-N 0.000 description 1
GMZCIFSUEAAWPF-UHFFFAOYSA-N 5-o-[3-[4-(2-hydroxyethyl)phenoxy]propyl] 3-o-methyl 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCO)=CC=2)C1C1=CC=CC(Cl)=C1 GMZCIFSUEAAWPF-UHFFFAOYSA-N 0.000 description 1
SZOITWFBHAMFDL-UHFFFAOYSA-N 5-o-[3-[4-(2-hydroxyethyl)phenoxy]propyl] 3-o-methyl 4-(3-fluorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCO)=CC=2)C1C1=CC=CC(F)=C1 SZOITWFBHAMFDL-UHFFFAOYSA-N 0.000 description 1
UFTZXUXUTPJIKO-UHFFFAOYSA-N 5-o-[3-[4-(2-hydroxyethyl)phenyl]sulfanylpropyl] 3-o-methyl 2,6-diethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCC=1NC(CC)=C(C(=O)OC)C(C=2C=C(C=CC=2)[N+]([O-])=O)C=1C(=O)OCCCSC1=CC=C(CCO)C=C1 UFTZXUXUTPJIKO-UHFFFAOYSA-N 0.000 description 1
PSJIVCPVYPIZJL-UHFFFAOYSA-N 5-o-[3-[4-(2-hydroxyethyl)phenyl]sulfanylpropyl] 3-o-methyl 2-ethyl-4-(3-nitrophenyl)-6-propyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(CC)NC(CCC)=C(C(=O)OCCCSC=2C=CC(CCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 PSJIVCPVYPIZJL-UHFFFAOYSA-N 0.000 description 1
GRRVRBGRSLKQJT-UHFFFAOYSA-N 5-o-[3-[4-(2-hydroxyethyl)phenyl]sulfanylpropyl] 3-o-methyl 2-ethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC=1NC(CC)=C(C(=O)OC)C(C=2C=C(C=CC=2)[N+]([O-])=O)C=1C(=O)OCCCSC1=CC=C(CCO)C=C1 GRRVRBGRSLKQJT-UHFFFAOYSA-N 0.000 description 1
MACNNDFERYHMFD-UHFFFAOYSA-N 5-o-[3-[4-(2-methoxyethyl)phenyl]sulfanylpropyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CCOC)=CC=C1SCCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 MACNNDFERYHMFD-UHFFFAOYSA-N 0.000 description 1
ZYDUNNMAFXSZGY-UHFFFAOYSA-N 5-o-[3-[4-(2-methoxyethyl)phenyl]sulfinylpropyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CCOC)=CC=C1S(=O)CCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 ZYDUNNMAFXSZGY-UHFFFAOYSA-N 0.000 description 1
JZCFQWGHQDVEDO-UHFFFAOYSA-N 5-o-[3-[4-(2-methoxyethyl)phenyl]sulfonylpropyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1=CC(CCOC)=CC=C1S(=O)(=O)CCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 JZCFQWGHQDVEDO-UHFFFAOYSA-N 0.000 description 1
UEFQBPJIYACUCE-UHFFFAOYSA-N 5-o-[3-[4-(3-hydroxypropyl)phenoxy]propyl] 3-o-methyl 2,6-diethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCC=1NC(CC)=C(C(=O)OC)C(C=2C=C(C=CC=2)[N+]([O-])=O)C=1C(=O)OCCCOC1=CC=C(CCCO)C=C1 UEFQBPJIYACUCE-UHFFFAOYSA-N 0.000 description 1
FRVWRUHJKUIFRI-UHFFFAOYSA-N 5-o-[3-[4-(3-hydroxypropyl)phenoxy]propyl] 3-o-methyl 2-ethyl-4-(3-nitrophenyl)-6-propyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(CC)NC(CCC)=C(C(=O)OCCCOC=2C=CC(CCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 FRVWRUHJKUIFRI-UHFFFAOYSA-N 0.000 description 1
MOHIALGFJQUGQH-UHFFFAOYSA-N 5-o-[3-[4-(3-hydroxypropyl)phenoxy]propyl] 3-o-methyl 2-ethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC=1NC(CC)=C(C(=O)OC)C(C=2C=C(C=CC=2)[N+]([O-])=O)C=1C(=O)OCCCOC1=CC=C(CCCO)C=C1 MOHIALGFJQUGQH-UHFFFAOYSA-N 0.000 description 1
DLDNIZGGCULTOA-UHFFFAOYSA-N 5-o-[3-[4-(3-hydroxypropyl)phenyl]sulfanylpropyl] 3-o-methyl 2-ethyl-4-(3-nitrophenyl)-6-propyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(CC)NC(CCC)=C(C(=O)OCCCSC=2C=CC(CCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 DLDNIZGGCULTOA-UHFFFAOYSA-N 0.000 description 1
XJLHNUXUAUWBSS-UHFFFAOYSA-N 5-o-[3-[4-(3-hydroxypropyl)phenyl]sulfanylpropyl] 3-o-methyl 2-ethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CC=1NC(CC)=C(C(=O)OC)C(C=2C=C(C=CC=2)[N+]([O-])=O)C=1C(=O)OCCCSC1=CC=C(CCCO)C=C1 XJLHNUXUAUWBSS-UHFFFAOYSA-N 0.000 description 1
YSKZGXOLVAPPMJ-UHFFFAOYSA-N 5-o-[3-[4-(4-hydroxybutyl)phenoxy]propyl] 3-o-methyl 2-ethyl-4-(3-nitrophenyl)-6-propyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(CC)NC(CCC)=C(C(=O)OCCCOC=2C=CC(CCCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 YSKZGXOLVAPPMJ-UHFFFAOYSA-N 0.000 description 1
QUGZHPOWMLPZKM-UHFFFAOYSA-N 5-o-[3-[4-(4-hydroxybutyl)phenyl]sulfanylpropyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCSC=2C=CC(CCCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 QUGZHPOWMLPZKM-UHFFFAOYSA-N 0.000 description 1
ZKCSKZYPEFOSCA-UHFFFAOYSA-N 5-o-[3-[4-(4-hydroxybutyl)phenyl]sulfanylpropyl] 3-o-methyl 2-ethyl-4-(3-nitrophenyl)-6-propyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(CC)NC(CCC)=C(C(=O)OCCCSC=2C=CC(CCCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZKCSKZYPEFOSCA-UHFFFAOYSA-N 0.000 description 1
WEMNIWIZBQAPKE-YTTGMZPUSA-N 5-o-[3-[4-[2-(cyclohexyloxymethoxy)ethyl]phenoxy]propyl] 3-o-methyl (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound C1([C@@H]2C(=C(C)NC(C)=C2C(=O)OC)C(=O)OCCCOC=2C=CC(CCOCOC3CCCCC3)=CC=2)=CC=CC([N+]([O-])=O)=C1 WEMNIWIZBQAPKE-YTTGMZPUSA-N 0.000 description 1
WEMNIWIZBQAPKE-UHFFFAOYSA-N 5-o-[3-[4-[2-(cyclohexyloxymethoxy)ethyl]phenoxy]propyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCOC=2C=CC(CCOCOC3CCCCC3)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 WEMNIWIZBQAPKE-UHFFFAOYSA-N 0.000 description 1
ROCKACFXCIZDKF-UHFFFAOYSA-N 5-o-[4-[4-(2-hydroxyethyl)phenoxy]butyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCCOC=2C=CC(CCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ROCKACFXCIZDKF-UHFFFAOYSA-N 0.000 description 1
PXNCWTYVDREJSF-UHFFFAOYSA-N 5-o-[4-[4-(2-hydroxyethyl)phenyl]sulfanylbutyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCCSC=2C=CC(CCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 PXNCWTYVDREJSF-UHFFFAOYSA-N 0.000 description 1
BEXQQROGHPLOAI-UHFFFAOYSA-N 5-o-[4-[4-(3-hydroxypropyl)phenoxy]butyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCCOC=2C=CC(CCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 BEXQQROGHPLOAI-UHFFFAOYSA-N 0.000 description 1
KGSSXXWFBWVIKO-UHFFFAOYSA-N 5-o-[4-[4-(3-hydroxypropyl)phenyl]sulfanylbutyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCCSC=2C=CC(CCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 KGSSXXWFBWVIKO-UHFFFAOYSA-N 0.000 description 1
HHSXSFDUTPOGBF-UHFFFAOYSA-N 5-o-[4-[4-(4-hydroxybutyl)phenoxy]butyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCCOC=2C=CC(CCCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 HHSXSFDUTPOGBF-UHFFFAOYSA-N 0.000 description 1
AEACKVLSFJKKKQ-UHFFFAOYSA-N 5-o-[4-[4-(4-hydroxybutyl)phenyl]sulfanylbutyl] 3-o-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCCCSC=2C=CC(CCCCO)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 AEACKVLSFJKKKQ-UHFFFAOYSA-N 0.000 description 1
VZBIJNACWBORNS-UHFFFAOYSA-N 5-o-methyl 3-o-[3-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]propyl] 2-ethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(CC)=C(C(=O)OCCCOC=2C=CC(CCOC3OCCCC3)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 VZBIJNACWBORNS-UHFFFAOYSA-N 0.000 description 1
QPDLVAOHBRMXKF-UHFFFAOYSA-N 5-o-methyl 3-o-[3-[4-[4-(oxan-2-yloxy)butyl]phenoxy]propyl] 2-ethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(CC)=C(C(=O)OCCCOC=2C=CC(CCCCOC3OCCCC3)=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 QPDLVAOHBRMXKF-UHFFFAOYSA-N 0.000 description 1
JPXPPUOCSLMCHK-AWEZNQCLSA-N 76093-34-0 Chemical compound COC(=O)C1=C(C)NC(C)=C(C(O)=O)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 JPXPPUOCSLMCHK-AWEZNQCLSA-N 0.000 description 1
DAXUDTBZGUYBHK-UHFFFAOYSA-N 8-(4-phenylmethoxyphenyl)octan-1-ol Chemical compound C1=CC(CCCCCCCCO)=CC=C1OCC1=CC=CC=C1 DAXUDTBZGUYBHK-UHFFFAOYSA-N 0.000 description 1
PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 description 1
GRZGHPXRROHARG-UHFFFAOYSA-N 8-[4-[2-(oxan-2-yloxy)ethyl]phenoxy]octan-1-ol Chemical compound C1=CC(OCCCCCCCCO)=CC=C1CCOC1OCCCC1 GRZGHPXRROHARG-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
101100439288 Bombyx mori nuclear polyhedrosis virus CG30 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
DIIWSYPKAJVXBV-UHFFFAOYSA-N Hantzch dihydropyridine Natural products CCOC(=O)C1=CC(C(=O)OCC)=C(C)N=C1C DIIWSYPKAJVXBV-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
229910018954 NaNH2 Inorganic materials 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
150000004729 acetoacetic acid derivatives Chemical class 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000009471 action Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
DLGYNVMUCSTYDQ-UHFFFAOYSA-N azane;pyridine Chemical compound N.C1=CC=NC=C1 DLGYNVMUCSTYDQ-UHFFFAOYSA-N 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
230000036760 body temperature Effects 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
NCZTZFYSDMXEPN-UHFFFAOYSA-N bromomethoxycyclohexane Chemical compound BrCOC1CCCCC1 NCZTZFYSDMXEPN-UHFFFAOYSA-N 0.000 description 1
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
230000005792 cardiovascular activity Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
230000008859 change Effects 0.000 description 1
GYCLGFVWNVHUPA-UHFFFAOYSA-N chloromethoxycyclohexane Chemical compound ClCOC1CCCCC1 GYCLGFVWNVHUPA-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000004087 circulation Effects 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940125797 compound 12 Drugs 0.000 description 1
229940126142 compound 16 Drugs 0.000 description 1
210000002808 connective tissue Anatomy 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
230000001186 cumulative effect Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000002993 cycloalkylene group Chemical group 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
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([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
125000004859 cyclopropyloxymethyl group Chemical group C1(CC1)OC* 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
238000011067 equilibration Methods 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
SKOURRNNESBPHU-UHFFFAOYSA-N ethyl 3-aminohept-2-enoate Chemical compound CCCCC(N)=CC(=O)OCC SKOURRNNESBPHU-UHFFFAOYSA-N 0.000 description 1
WLIGDZJHZGUCTD-UHFFFAOYSA-N ethyl 3-aminohex-2-enoate Chemical compound CCCC(N)=CC(=O)OCC WLIGDZJHZGUCTD-UHFFFAOYSA-N 0.000 description 1
ZRLNPHNIOXIZHR-UHFFFAOYSA-N ethyl 3-aminopent-2-enoate Chemical compound CCOC(=O)C=C(N)CC ZRLNPHNIOXIZHR-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
210000003191 femoral vein Anatomy 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000007710 freezing Methods 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000003304 gavage Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
230000014509 gene expression Effects 0.000 description 1
239000008103 glucose Substances 0.000 description 1
YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
244000144993 groups of animals Species 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000005911 haloform reaction Methods 0.000 description 1
210000003709 heart valve Anatomy 0.000 description 1
230000000004 hemodynamic effect Effects 0.000 description 1
DDTGNKBZWQHIEH-UHFFFAOYSA-N heptalene Chemical compound C1=CC=CC=C2C=CC=CC=C21 DDTGNKBZWQHIEH-UHFFFAOYSA-N 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
208000015210 hypertensive heart disease Diseases 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
230000003601 intercostal effect Effects 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000010410 layer Substances 0.000 description 1
229960004194 lidocaine Drugs 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000008297 liquid dosage form Substances 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
231100000682 maximum tolerated dose Toxicity 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
AHRVBVXGIXUOBR-CQSZACIVSA-N methyl (4s)-5-carbonochloridoyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(Cl)=O)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 AHRVBVXGIXUOBR-CQSZACIVSA-N 0.000 description 1
UKEDCGAGOCUUFO-UHFFFAOYSA-N methyl 2-(2-benzylsulfanylphenyl)acetate Chemical compound COC(=O)CC1=CC=CC=C1SCC1=CC=CC=C1 UKEDCGAGOCUUFO-UHFFFAOYSA-N 0.000 description 1
CPIKEDMPXDEUED-UHFFFAOYSA-N methyl 2-(2-phenylmethoxyphenyl)acetate Chemical compound COC(=O)CC1=CC=CC=C1OCC1=CC=CC=C1 CPIKEDMPXDEUED-UHFFFAOYSA-N 0.000 description 1
JKXJOTDLJPWAQA-UHFFFAOYSA-N methyl 2-(2-sulfanylphenyl)acetate Chemical compound COC(=O)CC1=CC=CC=C1S JKXJOTDLJPWAQA-UHFFFAOYSA-N 0.000 description 1
WSRIYLUNABOEMY-UHFFFAOYSA-N methyl 2-(3-benzylsulfanylphenyl)acetate Chemical compound COC(CC1=CC(=CC=C1)SCC1=CC=CC=C1)=O WSRIYLUNABOEMY-UHFFFAOYSA-N 0.000 description 1
AMDDOQIUPAINLH-UHFFFAOYSA-N methyl 2-(3-hydroxyphenyl)acetate Chemical compound COC(=O)CC1=CC=CC(O)=C1 AMDDOQIUPAINLH-UHFFFAOYSA-N 0.000 description 1
PGBWCJFWJDBDOY-UHFFFAOYSA-N methyl 2-(3-phenylmethoxyphenyl)acetate Chemical compound COC(=O)CC1=CC=CC(OCC=2C=CC=CC=2)=C1 PGBWCJFWJDBDOY-UHFFFAOYSA-N 0.000 description 1
XFBPQJQVVAADEG-UHFFFAOYSA-N methyl 2-(3-sulfanylphenyl)acetate Chemical compound COC(=O)CC1=CC=CC(S)=C1 XFBPQJQVVAADEG-UHFFFAOYSA-N 0.000 description 1
TXAJWLXWNZRELC-UHFFFAOYSA-N methyl 3-(3-phenylmethoxyphenyl)propanoate Chemical compound COC(=O)CCC1=CC=CC(OCC=2C=CC=CC=2)=C1 TXAJWLXWNZRELC-UHFFFAOYSA-N 0.000 description 1
QUASQDDMPBZTJV-UHFFFAOYSA-N methyl 3-(4-benzylsulfanylphenyl)propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1SCC1=CC=CC=C1 QUASQDDMPBZTJV-UHFFFAOYSA-N 0.000 description 1
XAAMAAXKDLWBKO-UHFFFAOYSA-N methyl 3-(4-phenylmethoxyphenyl)propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1OCC1=CC=CC=C1 XAAMAAXKDLWBKO-UHFFFAOYSA-N 0.000 description 1
BXMQSECLXFZSSW-UHFFFAOYSA-N methyl 3-(4-sulfanylphenyl)propanoate Chemical compound COC(=O)CCC1=CC=C(S)C=C1 BXMQSECLXFZSSW-UHFFFAOYSA-N 0.000 description 1
BFEOFKSBOLJJBC-UHFFFAOYSA-N methyl 3-aminohept-2-enoate Chemical compound CCCCC(N)=CC(=O)OC BFEOFKSBOLJJBC-UHFFFAOYSA-N 0.000 description 1
GLHATHZBPJZOFM-UHFFFAOYSA-N methyl 3-aminohex-2-enoate Chemical compound CCCC(N)=CC(=O)OC GLHATHZBPJZOFM-UHFFFAOYSA-N 0.000 description 1
NKSXDMWAVIOSTD-UHFFFAOYSA-N methyl 3-aminopent-2-enoate Chemical compound CCC(N)=CC(=O)OC NKSXDMWAVIOSTD-UHFFFAOYSA-N 0.000 description 1
UUMPJJUSWJCWJU-UHFFFAOYSA-N methyl 4-(2-hydroxyphenyl)butanoate Chemical compound COC(=O)CCCC1=CC=CC=C1O UUMPJJUSWJCWJU-UHFFFAOYSA-N 0.000 description 1
AFAJLADAPGVGEW-UHFFFAOYSA-N methyl 4-(2-phenylmethoxyphenyl)butanoate Chemical compound COC(=O)CCCC1=CC=CC=C1OCC1=CC=CC=C1 AFAJLADAPGVGEW-UHFFFAOYSA-N 0.000 description 1
DBUXPVJVONZZRG-UHFFFAOYSA-N methyl 4-(4-benzylsulfanylphenyl)butanoate Chemical compound C1=CC(CCCC(=O)OC)=CC=C1SCC1=CC=CC=C1 DBUXPVJVONZZRG-UHFFFAOYSA-N 0.000 description 1
KIAAKSMOURTFPF-UHFFFAOYSA-N methyl 4-(4-phenylmethoxyphenyl)butanoate Chemical compound C1=CC(CCCC(=O)OC)=CC=C1OCC1=CC=CC=C1 KIAAKSMOURTFPF-UHFFFAOYSA-N 0.000 description 1
AWPBIOJPJCZQAF-UHFFFAOYSA-N methyl 4-(4-sulfanylphenyl)butanoate Chemical compound COC(=O)CCCC1=CC=C(S)C=C1 AWPBIOJPJCZQAF-UHFFFAOYSA-N 0.000 description 1
AHRVBVXGIXUOBR-UHFFFAOYSA-N methyl 5-carbonochloridoyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(Cl)=O)C1C1=CC=CC([N+]([O-])=O)=C1 AHRVBVXGIXUOBR-UHFFFAOYSA-N 0.000 description 1
UTMRJTFGOWKODR-UHFFFAOYSA-N methyl 8-(4-hydroxyphenyl)octanoate Chemical compound COC(=O)CCCCCCCC1=CC=C(O)C=C1 UTMRJTFGOWKODR-UHFFFAOYSA-N 0.000 description 1
PILNDXCLDCPGLT-UHFFFAOYSA-N methyl 8-(4-phenylmethoxyphenyl)octanoate Chemical compound C1=CC(CCCCCCCC(=O)OC)=CC=C1OCC1=CC=CC=C1 PILNDXCLDCPGLT-UHFFFAOYSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
RAYLUPYCGGKXQO-UHFFFAOYSA-N n,n-dimethylacetamide;hydrate Chemical compound O.CN(C)C(C)=O RAYLUPYCGGKXQO-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000026536 negative regulation of muscle contraction Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
OVPVGJFDFSJUIG-UHFFFAOYSA-N octalene Chemical compound C1=CC=CC=C2C=CC=CC=CC2=C1 OVPVGJFDFSJUIG-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
210000003540 papillary muscle Anatomy 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
230000036513 peripheral conductance Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
239000012071 phase Substances 0.000 description 1
229960005323 phenoxyethanol Drugs 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
230000035479 physiological effects, processes and functions Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
CQUZJDGPLCZZHE-UHFFFAOYSA-N propan-2-yl 3-aminohept-2-enoate Chemical compound CCCCC(N)=CC(=O)OC(C)C CQUZJDGPLCZZHE-UHFFFAOYSA-N 0.000 description 1
OOECCWJKLLYVRK-UHFFFAOYSA-N propan-2-yl 3-aminohex-2-enoate Chemical compound CCCC(N)=CC(=O)OC(C)C OOECCWJKLLYVRK-UHFFFAOYSA-N 0.000 description 1
NWUVNUVXKGJKEJ-UHFFFAOYSA-N propan-2-yl 3-aminopent-2-enoate Chemical compound CCC(N)=CC(=O)OC(C)C NWUVNUVXKGJKEJ-UHFFFAOYSA-N 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
230000005588 protonation Effects 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
239000000523 sample Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
235000020183 skimmed milk Nutrition 0.000 description 1
239000002002 slurry Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
230000002792 vascular Effects 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1