HRP980487A2

HRP980487A2 - 2-(arylphenyl)amino-imidazoline derivatives

2-(arylphenyl)amino-imidazoline derivatives

Info

Publication number: HRP980487A2
Authority: HR; Croatia
Prior art keywords: phenyl; amino; imidazoline; formula; compound
Prior art date: 1997-09-04

Application number

Other languages

English (en)

Croatian (hr)

Inventor

Thomas Weitao Sun

Original Assignee

Hoffmann La Roche

Priority date

1997-09-04

Filing date

1998-09-03

Publication date

1999-06-30

1998-09-03 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1999-06-30 Publication of HRP980487A2 publication Critical patent/HRP980487A2/hr

Links

MSYFITFSZJKRQJ-UHFFFAOYSA-N 4,5-dihydroimidazol-1-amine Chemical class NN1CCN=C1 MSYFITFSZJKRQJ-UHFFFAOYSA-N 0.000 title claims description 18
150000001875 compounds Chemical class 0.000 claims description 243
238000000034 method Methods 0.000 claims description 123
239000000203 mixture Substances 0.000 claims description 123
-1 2-ethoxy-1- (ethoxymethyl)ethyl Chemical group 0.000 claims description 103
238000006243 chemical reaction Methods 0.000 claims description 68
239000001257 hydrogen Substances 0.000 claims description 43
229910052739 hydrogen Inorganic materials 0.000 claims description 43
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
125000000217 alkyl group Chemical group 0.000 claims description 32
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 24
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
238000011282 treatment Methods 0.000 claims description 21
125000000753 cycloalkyl group Chemical group 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 19
201000010099 disease Diseases 0.000 claims description 18
125000000623 heterocyclic group Chemical group 0.000 claims description 18
229910052757 nitrogen Inorganic materials 0.000 claims description 18
208000002193 Pain Diseases 0.000 claims description 17
230000036407 pain Effects 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 13
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
206010040070 Septic Shock Diseases 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
239000004615 ingredient Substances 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 9
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
125000001072 heteroaryl group Chemical group 0.000 claims description 8
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
125000001188 haloalkyl group Chemical group 0.000 claims description 7
108091006335 Prostaglandin I receptors Proteins 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
239000002464 receptor antagonist Substances 0.000 claims description 6
229940044551 receptor antagonist Drugs 0.000 claims description 6
230000036303 septic shock Effects 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 5
125000004181 carboxyalkyl group Chemical group 0.000 claims description 5
125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
125000002950 monocyclic group Chemical group 0.000 claims description 5
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 5
206010061218 Inflammation Diseases 0.000 claims description 4
206010046543 Urinary incontinence Diseases 0.000 claims description 4
208000006673 asthma Diseases 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 4
230000004054 inflammatory process Effects 0.000 claims description 4
ZODCLJXQLFWUHZ-UHFFFAOYSA-N n-[4-[[4-(oxan-4-yloxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C=1C=C(OC2CCOCC2)C=CC=1CC(C=C1)=CC=C1NC1=NCCN1 ZODCLJXQLFWUHZ-UHFFFAOYSA-N 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
VCSASCHCRWKXIK-UHFFFAOYSA-N 2-[4-[[4-(oxan-4-ylmethoxy)phenyl]methyl]phenyl]-4,5-dihydroimidazol-1-amine Chemical compound NN1CCN=C1c1ccc(Cc2ccc(OCC3CCOCC3)cc2)cc1 VCSASCHCRWKXIK-UHFFFAOYSA-N 0.000 claims description 3
GYYRMJMXXLJZAB-UHFFFAOYSA-N n-[4-[(4-propan-2-yloxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1=CC(OC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 GYYRMJMXXLJZAB-UHFFFAOYSA-N 0.000 claims description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
230000001225 therapeutic effect Effects 0.000 claims description 3
QKRWWYXZUXIMNY-UHFFFAOYSA-N 2-[4-[[4-(1,3-diethoxypropan-2-yloxy)phenyl]methyl]phenyl]-4,5-dihydroimidazol-1-amine Chemical compound C1=CC(OC(COCC)COCC)=CC=C1CC1=CC=C(C=2N(CCN=2)N)C=C1 QKRWWYXZUXIMNY-UHFFFAOYSA-N 0.000 claims description 2
JDLYEHJOMPVQFU-UHFFFAOYSA-N 2-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenoxy]propan-1-ol Chemical compound C1=CC(OC(CO)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 JDLYEHJOMPVQFU-UHFFFAOYSA-N 0.000 claims description 2
CLXATQQHVVAEID-UHFFFAOYSA-N 2-[4-[[4-(oxan-2-ylmethoxy)phenyl]methyl]phenyl]-4,5-dihydroimidazol-1-amine Chemical compound NN1CCN=C1C(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1OCCCC1 CLXATQQHVVAEID-UHFFFAOYSA-N 0.000 claims description 2
JFODXFPIYJCKGA-UHFFFAOYSA-N 4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]-n-(2-methylpropyl)benzamide Chemical compound C1=CC(C(=O)NCC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 JFODXFPIYJCKGA-UHFFFAOYSA-N 0.000 claims description 2
GVNBSLRDMFBJJL-UHFFFAOYSA-N 4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]-n-(2-methylpropyl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 GVNBSLRDMFBJJL-UHFFFAOYSA-N 0.000 claims description 2
MLJPVCGKYSYMJC-UHFFFAOYSA-N 4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]-n-propan-2-ylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 MLJPVCGKYSYMJC-UHFFFAOYSA-N 0.000 claims description 2
LNKKILTYFJGMJF-UHFFFAOYSA-N n-[4-[(4-butan-2-yloxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1=CC(OC(C)CC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 LNKKILTYFJGMJF-UHFFFAOYSA-N 0.000 claims description 2
YDNNLWHCIDLUFN-UHFFFAOYSA-N n-[4-[(4-cyclopentyloxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C=1C=C(OC2CCCC2)C=CC=1CC(C=C1)=CC=C1NC1=NCCN1 YDNNLWHCIDLUFN-UHFFFAOYSA-N 0.000 claims description 2
JLNFCMIBOXQHSH-UHFFFAOYSA-N n-[4-[[2-fluoro-4-(oxan-4-ylmethoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C=1C=C(CC=2C=CC(NC=3NCCN=3)=CC=2)C(F)=CC=1OCC1CCOCC1 JLNFCMIBOXQHSH-UHFFFAOYSA-N 0.000 claims description 2
MXPUNYONDDMSHO-UHFFFAOYSA-N n-[4-[[4-(butan-2-yloxymethyl)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1=CC(COC(C)CC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 MXPUNYONDDMSHO-UHFFFAOYSA-N 0.000 claims description 2
OLPAAAJTXBQPIL-UHFFFAOYSA-N n-[4-[ethoxy-[4-[(4-methoxyphenyl)sulfonylmethylamino]phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C=1C=C(NC=2NCCN=2)C=CC=1C(OCC)C(C=C1)=CC=C1NCS(=O)(=O)C1=CC=C(OC)C=C1 OLPAAAJTXBQPIL-UHFFFAOYSA-N 0.000 claims description 2
HYAQHWBZFXCUKL-UHFFFAOYSA-N n-benzyl-4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]benzamide Chemical compound C=1C=C(CC=2C=CC(NC=3NCCN=3)=CC=2)C=CC=1C(=O)NCC1=CC=CC=C1 HYAQHWBZFXCUKL-UHFFFAOYSA-N 0.000 claims description 2
YGJRAVQHTWJWBA-UHFFFAOYSA-N n-butyl-4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCCCC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 YGJRAVQHTWJWBA-UHFFFAOYSA-N 0.000 claims description 2
RBYQCNLYMCZGMK-UHFFFAOYSA-N n-tert-butyl-4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC(C)(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 RBYQCNLYMCZGMK-UHFFFAOYSA-N 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims 1
230000003000 nontoxic effect Effects 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 256
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 180
238000002844 melting Methods 0.000 description 139
230000008018 melting Effects 0.000 description 137
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 114
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 114
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
229910001868 water Inorganic materials 0.000 description 99
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 96
239000000243 solution Substances 0.000 description 86
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 75
238000004458 analytical method Methods 0.000 description 71
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 69
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
239000002904 solvent Substances 0.000 description 66
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 57
238000002360 preparation method Methods 0.000 description 52
239000007787 solid Substances 0.000 description 52
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 48
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 47
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 37
239000003960 organic solvent Substances 0.000 description 36
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
239000011541 reaction mixture Substances 0.000 description 28
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 26
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
239000012298 atmosphere Substances 0.000 description 24
239000002585 base Substances 0.000 description 24
150000002431 hydrogen Chemical class 0.000 description 23
239000000741 silica gel Substances 0.000 description 23
229910002027 silica gel Inorganic materials 0.000 description 23
239000007832 Na2SO4 Substances 0.000 description 22
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
239000013543 active substance Substances 0.000 description 22
229910052938 sodium sulfate Inorganic materials 0.000 description 22
235000011152 sodium sulphate Nutrition 0.000 description 22
239000003921 oil Substances 0.000 description 21
235000019198 oils Nutrition 0.000 description 21
239000003054 catalyst Substances 0.000 description 20
239000003795 chemical substances by application Substances 0.000 description 20
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 20
239000012043 crude product Substances 0.000 description 19
239000012044 organic layer Substances 0.000 description 19
238000010992 reflux Methods 0.000 description 19
239000000543 intermediate Substances 0.000 description 18
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 18
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 17
241000700159 Rattus Species 0.000 description 17
239000000284 extract Substances 0.000 description 17
238000009472 formulation Methods 0.000 description 17
239000000843 powder Substances 0.000 description 17
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 17
239000000047 product Substances 0.000 description 16
125000006239 protecting group Chemical group 0.000 description 16
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
230000008602 contraction Effects 0.000 description 15
210000002683 foot Anatomy 0.000 description 15
239000012266 salt solution Substances 0.000 description 15
229910000027 potassium carbonate Inorganic materials 0.000 description 14
229910052786 argon Inorganic materials 0.000 description 13
239000002775 capsule Substances 0.000 description 13
238000004587 chromatography analysis Methods 0.000 description 13
230000005764 inhibitory process Effects 0.000 description 13
238000005160 1H NMR spectroscopy Methods 0.000 description 12
208000004454 Hyperalgesia Diseases 0.000 description 12
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 12
241001465754 Metazoa Species 0.000 description 12
230000000694 effects Effects 0.000 description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 12
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 12
235000011181 potassium carbonates Nutrition 0.000 description 12
238000000746 purification Methods 0.000 description 12
239000000725 suspension Substances 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 11
239000012267 brine Substances 0.000 description 11
239000013078 crystal Substances 0.000 description 11
230000009467 reduction Effects 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
239000000126 substance Substances 0.000 description 11
239000003826 tablet Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
238000002474 experimental method Methods 0.000 description 10
KAQKFAOMNZTLHT-OZUDYXHBSA-N prostaglandin I2 Chemical compound O1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-OZUDYXHBSA-N 0.000 description 10
229940127293 prostanoid Drugs 0.000 description 10
150000003814 prostanoids Chemical class 0.000 description 10
230000004044 response Effects 0.000 description 10
238000003756 stirring Methods 0.000 description 10
239000003981 vehicle Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
101000862089 Clarkia lewisii Glucose-6-phosphate isomerase, cytosolic 1A Proteins 0.000 description 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
239000000010 aprotic solvent Substances 0.000 description 9
235000010418 carrageenan Nutrition 0.000 description 9
239000000679 carrageenan Substances 0.000 description 9
229920001525 carrageenan Polymers 0.000 description 9
229940113118 carrageenan Drugs 0.000 description 9
238000002425 crystallisation Methods 0.000 description 9
230000008025 crystallization Effects 0.000 description 9
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 9
150000008282 halocarbons Chemical class 0.000 description 9
229910052763 palladium Inorganic materials 0.000 description 9
229910052697 platinum Inorganic materials 0.000 description 9
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 9
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 9
VZHOUEQLAZZYKK-UHFFFAOYSA-N 2-chloro-4,5-dihydro-1h-imidazole;sulfuric acid Chemical compound OS(O)(=O)=O.ClC1=NCCN1 VZHOUEQLAZZYKK-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 8
239000010410 layer Substances 0.000 description 8
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 8
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
PLQPJMPBVQUMGY-UHFFFAOYSA-N 4-[(4-propan-2-yloxyphenyl)methyl]aniline Chemical compound C1=CC(OC(C)C)=CC=C1CC1=CC=C(N)C=C1 PLQPJMPBVQUMGY-UHFFFAOYSA-N 0.000 description 7
238000002441 X-ray diffraction Methods 0.000 description 7
239000007810 chemical reaction solvent Substances 0.000 description 7
125000000468 ketone group Chemical group 0.000 description 7
239000007788 liquid Substances 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
238000012360 testing method Methods 0.000 description 7
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
208000001953 Hypotension Diseases 0.000 description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
239000002168 alkylating agent Substances 0.000 description 6
229940100198 alkylating agent Drugs 0.000 description 6
239000000908 ammonium hydroxide Substances 0.000 description 6
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 6
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 6
229960002986 dinoprostone Drugs 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
239000000839 emulsion Substances 0.000 description 6
239000002158 endotoxin Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000006260 foam Substances 0.000 description 6
230000036543 hypotension Effects 0.000 description 6
208000014674 injury Diseases 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 6
108020003175 receptors Proteins 0.000 description 6
102000005962 receptors Human genes 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
235000009518 sodium iodide Nutrition 0.000 description 6
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 6
IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 5
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 5
SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 5
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
208000035154 Hyperesthesia Diseases 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
125000003277 amino group Chemical group 0.000 description 5
150000001448 anilines Chemical class 0.000 description 5
230000003110 anti-inflammatory effect Effects 0.000 description 5
125000004744 butyloxycarbonyl group Chemical group 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
229940125807 compound 37 Drugs 0.000 description 5
239000003937 drug carrier Substances 0.000 description 5
238000001727 in vivo Methods 0.000 description 5
239000012948 isocyanate Substances 0.000 description 5
150000002513 isocyanates Chemical class 0.000 description 5
239000011734 sodium Substances 0.000 description 5
125000000565 sulfonamide group Chemical group 0.000 description 5
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 5
208000024891 symptom Diseases 0.000 description 5
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
TVRVBFNDNURZJF-UHFFFAOYSA-N (4-nitrophenyl)-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)C1=CC=C([N+]([O-])=O)C=C1 TVRVBFNDNURZJF-UHFFFAOYSA-N 0.000 description 4
FPONJHKBJZMGCX-UHFFFAOYSA-N 1-bromo-4-(propan-2-yloxymethyl)benzene Chemical compound CC(C)OCC1=CC=C(Br)C=C1 FPONJHKBJZMGCX-UHFFFAOYSA-N 0.000 description 4
OKEHURCMYKPVFW-UHFFFAOYSA-N 2-methoxythiophene Chemical compound COC1=CC=CS1 OKEHURCMYKPVFW-UHFFFAOYSA-N 0.000 description 4
208000035143 Bacterial infection Diseases 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
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 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
208000036142 Viral infection Diseases 0.000 description 4
208000027418 Wounds and injury Diseases 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 4
230000004913 activation Effects 0.000 description 4
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 4
230000001476 alcoholic effect Effects 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
230000001760 anti-analgesic effect Effects 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000003556 assay Methods 0.000 description 4
208000022362 bacterial infectious disease Diseases 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
239000000969 carrier Substances 0.000 description 4
238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 4
XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000012458 free base Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
239000005457 ice water Substances 0.000 description 4
230000002757 inflammatory effect Effects 0.000 description 4
239000008101 lactose Substances 0.000 description 4
239000007937 lozenge Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
239000000463 material Substances 0.000 description 4
239000002480 mineral oil Substances 0.000 description 4
235000010446 mineral oil Nutrition 0.000 description 4
230000004048 modification Effects 0.000 description 4
238000012986 modification Methods 0.000 description 4
UOWPPPOMBGRWGP-UHFFFAOYSA-N n-[4-[(4-propan-2-yloxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC(OC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 UOWPPPOMBGRWGP-UHFFFAOYSA-N 0.000 description 4
229940097496 nasal spray Drugs 0.000 description 4
239000007922 nasal spray Substances 0.000 description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
238000012746 preparative thin layer chromatography Methods 0.000 description 4
238000011160 research Methods 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
239000007921 spray Substances 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000829 suppository Substances 0.000 description 4
239000000375 suspending agent Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
239000002562 thickening agent Substances 0.000 description 4
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 3
SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 3
ZEYDQRVULMQZIU-UHFFFAOYSA-N (4-hydroxyphenyl)-(4-nitrophenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C([N+]([O-])=O)C=C1 ZEYDQRVULMQZIU-UHFFFAOYSA-N 0.000 description 3
NZZIYFZVUDLYBJ-UHFFFAOYSA-N 1-(bromomethyl)-4-[(4-nitrophenyl)methyl]benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC1=CC=C(CBr)C=C1 NZZIYFZVUDLYBJ-UHFFFAOYSA-N 0.000 description 3
WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 3
LDCVBNCPHSEWGX-UHFFFAOYSA-N 2,2,2-trifluoro-n-[4-(piperidin-4-ylmethyl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C(F)(F)F)=CC=C1CC1CCNCC1 LDCVBNCPHSEWGX-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UZQPQWGAOHUDRO-UHFFFAOYSA-N 2-benzyl-3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1CC1=CC=CC=C1 UZQPQWGAOHUDRO-UHFFFAOYSA-N 0.000 description 3
NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
BLNHLPPJDFYMDH-UHFFFAOYSA-N 4-(piperidin-4-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CC1CCNCC1 BLNHLPPJDFYMDH-UHFFFAOYSA-N 0.000 description 3
KGJPFPRRUKNQJJ-UHFFFAOYSA-N 4-[(4-nitrophenyl)methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CC1=CC=C([N+]([O-])=O)C=C1 KGJPFPRRUKNQJJ-UHFFFAOYSA-N 0.000 description 3
GXQVXPWSUFKZBD-UHFFFAOYSA-N 4-[(5-methoxythiophen-2-yl)methyl]aniline Chemical compound S1C(OC)=CC=C1CC1=CC=C(N)C=C1 GXQVXPWSUFKZBD-UHFFFAOYSA-N 0.000 description 3
DTJVECUKADWGMO-UHFFFAOYSA-N 4-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1 DTJVECUKADWGMO-UHFFFAOYSA-N 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
229910015900 BF3 Inorganic materials 0.000 description 3
206010005033 Bladder dilatation Diseases 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
206010065390 Inflammatory pain Diseases 0.000 description 3
235000010643 Leucaena leucocephala Nutrition 0.000 description 3
240000007472 Leucaena leucocephala Species 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
229910019020 PtO2 Inorganic materials 0.000 description 3
206010066218 Stress Urinary Incontinence Diseases 0.000 description 3
GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 3
208000000921 Urge Urinary Incontinence Diseases 0.000 description 3
SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 3
150000001266 acyl halides Chemical class 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
150000001350 alkyl halides Chemical class 0.000 description 3
230000002152 alkylating effect Effects 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
239000012300 argon atmosphere Substances 0.000 description 3
230000036772 blood pressure Effects 0.000 description 3
QDWJUBJKEHXSMT-UHFFFAOYSA-N boranylidynenickel Chemical compound [Ni]#B QDWJUBJKEHXSMT-UHFFFAOYSA-N 0.000 description 3
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
229910000024 caesium carbonate Inorganic materials 0.000 description 3
239000001768 carboxy methyl cellulose Substances 0.000 description 3
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000006071 cream Substances 0.000 description 3
201000003146 cystitis Diseases 0.000 description 3
230000006378 damage Effects 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
230000036541 health Effects 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
150000007517 lewis acids Chemical class 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
OFTFBQYRYRZMTQ-UHFFFAOYSA-N n-[4-[(4-aminophenyl)methyl]phenyl]ethanesulfonamide Chemical compound C1=CC(NS(=O)(=O)CC)=CC=C1CC1=CC=C(N)C=C1 OFTFBQYRYRZMTQ-UHFFFAOYSA-N 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
229910017604 nitric acid Inorganic materials 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
229920006316 polyvinylpyrrolidine Polymers 0.000 description 3
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
238000000634 powder X-ray diffraction Methods 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
150000003180 prostaglandins Chemical class 0.000 description 3
239000003586 protic polar solvent Substances 0.000 description 3
230000001020 rhythmical effect Effects 0.000 description 3
150000003335 secondary amines Chemical class 0.000 description 3
210000001044 sensory neuron Anatomy 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 3
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 3
239000012453 solvate Substances 0.000 description 3
208000022170 stress incontinence Diseases 0.000 description 3
150000003461 sulfonyl halides Chemical class 0.000 description 3
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 3
AOYUPZDCHAYHRL-UHFFFAOYSA-N tributyl-(5-methoxythiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=C(OC)S1 AOYUPZDCHAYHRL-UHFFFAOYSA-N 0.000 description 3
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 3
210000001170 unmyelinated nerve fiber Anatomy 0.000 description 3
206010046494 urge incontinence Diseases 0.000 description 3
239000008215 water for injection Substances 0.000 description 3
239000001993 wax Substances 0.000 description 3
ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 2
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
RLQAIJGXSWCGFY-UHFFFAOYSA-N (2-methoxy-6-nitrophenyl)-phenylmethanone Chemical compound COC1=CC=CC([N+]([O-])=O)=C1C(=O)C1=CC=CC=C1 RLQAIJGXSWCGFY-UHFFFAOYSA-N 0.000 description 2
STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 2
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 2
HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 2
DXVSAELNVPXMSQ-UHFFFAOYSA-N (4-methoxyphenyl)-(4-nitrophenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C([N+]([O-])=O)C=C1 DXVSAELNVPXMSQ-UHFFFAOYSA-N 0.000 description 2
HHTOMEBQNGDWDW-UHFFFAOYSA-N (4-methylphenyl)-(4-nitrophenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C([N+]([O-])=O)C=C1 HHTOMEBQNGDWDW-UHFFFAOYSA-N 0.000 description 2
OLMMJMQJVJEHBG-UHFFFAOYSA-N (4-morpholin-4-ylphenyl)-(4-nitrophenyl)methanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)C1=CC=C(N2CCOCC2)C=C1 OLMMJMQJVJEHBG-UHFFFAOYSA-N 0.000 description 2
IXYQGLFZHQGEJO-UHFFFAOYSA-N (4-nitrophenyl)-[4-(oxan-4-yloxy)phenyl]methanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)C(C=C1)=CC=C1OC1CCOCC1 IXYQGLFZHQGEJO-UHFFFAOYSA-N 0.000 description 2
VIMMECPCYZXUCI-MIMFYIINSA-N (4s,6r)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical compound CN1N=NN=C1C(\C=C\[C@@H]1OC(=O)C[C@@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MIMFYIINSA-N 0.000 description 2
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
UEMGWPRHOOEKTA-UHFFFAOYSA-N 1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 0.000 description 2
RYEMDQQMRYNVCR-UHFFFAOYSA-N 1-(azidomethyl)-4-[(4-nitrophenyl)methyl]benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC1=CC=C(CN=[N+]=[N-])C=C1 RYEMDQQMRYNVCR-UHFFFAOYSA-N 0.000 description 2
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 2
PSOGBDOMKMPEGW-UHFFFAOYSA-N 1-[4-[(4-aminophenyl)methyl]phenyl]-3-phenylurea Chemical compound C1=CC(N)=CC=C1CC(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 PSOGBDOMKMPEGW-UHFFFAOYSA-N 0.000 description 2
HIABURSNWJYQLZ-UHFFFAOYSA-N 1-[4-[(4-aminophenyl)methyl]phenyl]-n-benzylmethanesulfonamide Chemical compound C1=CC(N)=CC=C1CC(C=C1)=CC=C1CS(=O)(=O)NCC1=CC=CC=C1 HIABURSNWJYQLZ-UHFFFAOYSA-N 0.000 description 2
PQJXWCJJHGKPSU-UHFFFAOYSA-N 1-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]-3-phenylurea Chemical compound C=1C=C(CC=2C=CC(NC=3NCCN=3)=CC=2)C=CC=1NC(=O)NC1=CC=CC=C1 PQJXWCJJHGKPSU-UHFFFAOYSA-N 0.000 description 2
MPAOOLLBWUEXOM-UHFFFAOYSA-N 1-bromo-4-propan-2-yloxybenzene Chemical compound CC(C)OC1=CC=C(Br)C=C1 MPAOOLLBWUEXOM-UHFFFAOYSA-N 0.000 description 2
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
LLTUHUMPJYLFDV-UHFFFAOYSA-N 2,2,2-trifluoro-n-[4-[(1-piperidin-1-ylsulfonylpiperidin-4-yl)methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C(F)(F)F)=CC=C1CC1CCN(S(=O)(=O)N2CCCCC2)CC1 LLTUHUMPJYLFDV-UHFFFAOYSA-N 0.000 description 2
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
MSGKDAJGWJUECG-UHFFFAOYSA-N 2-[4-[[4-(propan-2-yloxymethyl)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazole Chemical compound C1=CC(COC(C)C)=CC=C1CC1=CC=C(C=2NCCN=2)C=C1 MSGKDAJGWJUECG-UHFFFAOYSA-N 0.000 description 2
TUIUHRYVQRQYFX-UHFFFAOYSA-N 2-benzyl-1-bromo-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Br)=C1CC1=CC=CC=C1 TUIUHRYVQRQYFX-UHFFFAOYSA-N 0.000 description 2
TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 2
PHZLWUWVDIGSGG-UHFFFAOYSA-N 2-chloro-3-cyclopentyloxythiophene Chemical compound S1C=CC(OC2CCCC2)=C1Cl PHZLWUWVDIGSGG-UHFFFAOYSA-N 0.000 description 2
BFYRXCWLDJORHM-UHFFFAOYSA-N 2-chloro-4,5-dihydro-1h-imidazole Chemical compound ClC1=NCCN1 BFYRXCWLDJORHM-UHFFFAOYSA-N 0.000 description 2
DSJYDNGDLXIQBC-UHFFFAOYSA-N 2-cyclopentyloxythiophene Chemical compound C1CCCC1OC1=CC=CS1 DSJYDNGDLXIQBC-UHFFFAOYSA-N 0.000 description 2
GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 2
AIMHGIXLOUZFFW-UHFFFAOYSA-N 3-cyclopentyloxythiophene Chemical compound C1CCCC1OC1=CSC=C1 AIMHGIXLOUZFFW-UHFFFAOYSA-N 0.000 description 2
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
WNPHSUPZNGMPEP-UHFFFAOYSA-N 4-[(4-aminophenyl)methyl]-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1CC1=CC=C(N)C=C1 WNPHSUPZNGMPEP-UHFFFAOYSA-N 0.000 description 2
PNSZAGHNXSPZBQ-UHFFFAOYSA-N 4-[(4-aminophenyl)methyl]-n-propan-2-ylpiperidine-1-carboxamide Chemical compound C1CN(C(=O)NC(C)C)CCC1CC1=CC=C(N)C=C1 PNSZAGHNXSPZBQ-UHFFFAOYSA-N 0.000 description 2
PNEPVUHARXRCJJ-UHFFFAOYSA-N 4-[(4-cyclopentyloxythiophen-2-yl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC(OC2CCCC2)=CS1 PNEPVUHARXRCJJ-UHFFFAOYSA-N 0.000 description 2
CPDJGEZDJOIEMC-UHFFFAOYSA-N 4-[(4-nitrophenyl)methyl]benzoyl chloride Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC1=CC=C(C(Cl)=O)C=C1 CPDJGEZDJOIEMC-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
LTHNIVACRBCFGD-UHFFFAOYSA-N 4-[[1-(benzenesulfonyl)piperidin-4-yl]methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1CCN(S(=O)(=O)C=2C=CC=CC=2)CC1 LTHNIVACRBCFGD-UHFFFAOYSA-N 0.000 description 2
RPPXORHTXXKMFN-UHFFFAOYSA-N 4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 RPPXORHTXXKMFN-UHFFFAOYSA-N 0.000 description 2
BJUBELAQNFWBSI-UHFFFAOYSA-N 4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]-n-propan-2-ylpiperidine-1-carboxamide Chemical compound C1CN(C(=O)NC(C)C)CCC1CC(C=C1)=CC=C1NC1=NCCN1 BJUBELAQNFWBSI-UHFFFAOYSA-N 0.000 description 2
YHPBBOATPIGUBH-UHFFFAOYSA-N 4-[[4-(ethylsulfonylmethylamino)phenyl]methyl]aniline Chemical compound C1=CC(NCS(=O)(=O)CC)=CC=C1CC1=CC=C(N)C=C1 YHPBBOATPIGUBH-UHFFFAOYSA-N 0.000 description 2
SNUMHRFKYDUMAY-UHFFFAOYSA-N 4-[[4-(propan-2-yloxymethyl)phenyl]methyl]aniline Chemical compound C1=CC(COC(C)C)=CC=C1CC1=CC=C(N)C=C1 SNUMHRFKYDUMAY-UHFFFAOYSA-N 0.000 description 2
FPHVRPCVNPHPBH-UHFFFAOYSA-N 4-benzylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CC1=CC=CC=C1 FPHVRPCVNPHPBH-UHFFFAOYSA-N 0.000 description 2
DRSVJOOHNLPLJV-UHFFFAOYSA-N 4-methoxy-n-[[4-[(4-nitrophenyl)methyl]phenyl]methyl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NCC(C=C1)=CC=C1CC1=CC=C([N+]([O-])=O)C=C1 DRSVJOOHNLPLJV-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
241000416162 Astragalus gummifer Species 0.000 description 2
208000025978 Athletic injury Diseases 0.000 description 2
239000004342 Benzoyl peroxide Substances 0.000 description 2
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
239000004255 Butylated hydroxyanisole Substances 0.000 description 2
206010058019 Cancer Pain Diseases 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
229940127007 Compound 39 Drugs 0.000 description 2
206010010741 Conjunctivitis Diseases 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
206010012335 Dependence Diseases 0.000 description 2
206010014824 Endotoxic shock Diseases 0.000 description 2
238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 2
206010017533 Fungal infection Diseases 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
238000003747 Grignard reaction Methods 0.000 description 2
206010019233 Headaches Diseases 0.000 description 2
206010020853 Hypertonic bladder Diseases 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
208000005615 Interstitial Cystitis Diseases 0.000 description 2
DNVXATUJJDPFDM-KRWDZBQOSA-N JQ1 Chemical compound N([C@@H](CC(=O)OC(C)(C)C)C1=NN=C(N1C=1SC(C)=C(C)C=11)C)=C1C1=CC=C(Cl)C=C1 DNVXATUJJDPFDM-KRWDZBQOSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
208000019695 Migraine disease Diseases 0.000 description 2
208000031888 Mycoses Diseases 0.000 description 2
208000028389 Nerve injury Diseases 0.000 description 2
206010029240 Neuritis Diseases 0.000 description 2
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
206010030113 Oedema Diseases 0.000 description 2
208000009722 Overactive Urinary Bladder Diseases 0.000 description 2
208000030852 Parasitic disease Diseases 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
208000005374 Poisoning Diseases 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
206010065347 Premenstrual pain Diseases 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
238000000692 Student's t-test Methods 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
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 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
229920001615 Tragacanth Polymers 0.000 description 2
LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 2
FEWBCCFISWXNAU-UHFFFAOYSA-N [4-(5-chloro-4-cyclopentyloxythiophen-2-yl)-4-nitrocyclohexa-1,5-dien-1-yl]methanol Chemical compound C1=CC(CO)=CCC1([N+]([O-])=O)C1=CC(OC2CCCC2)=C(Cl)S1 FEWBCCFISWXNAU-UHFFFAOYSA-N 0.000 description 2
XZWWQXQBOBGNCU-UHFFFAOYSA-N [4-(bromomethyl)phenyl]-(4-nitrophenyl)methanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)C1=CC=C(CBr)C=C1 XZWWQXQBOBGNCU-UHFFFAOYSA-N 0.000 description 2
YCJQGPDXEIWCIY-UHFFFAOYSA-N [4-[(4-nitrophenyl)methyl]phenyl]-pyrrolidin-1-ylmethanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC1=CC=C(C(=O)N2CCCC2)C=C1 YCJQGPDXEIWCIY-UHFFFAOYSA-N 0.000 description 2
DORDCDZXEBWHCW-UHFFFAOYSA-N [4-[(4-nitrophenyl)methyl]phenyl]methanamine Chemical compound C1=CC(CN)=CC=C1CC1=CC=C([N+]([O-])=O)C=C1 DORDCDZXEBWHCW-UHFFFAOYSA-N 0.000 description 2
WHEUCWGMPILKAF-UHFFFAOYSA-N [4-[(4-nitrophenyl)methyl]phenyl]methanesulfonic acid Chemical compound C1=CC(CS(=O)(=O)O)=CC=C1CC1=CC=C([N+]([O-])=O)C=C1 WHEUCWGMPILKAF-UHFFFAOYSA-N 0.000 description 2
AVSHNICHSGKLDP-UHFFFAOYSA-N [4-[(4-nitrophenyl)methyl]phenyl]methanesulfonyl chloride Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC1=CC=C(CS(Cl)(=O)=O)C=C1 AVSHNICHSGKLDP-UHFFFAOYSA-N 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
230000003444 anaesthetic effect Effects 0.000 description 2
METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
235000019400 benzoyl peroxide Nutrition 0.000 description 2
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
IVQRIMSOKFMBEJ-UHFFFAOYSA-N benzyl n-[4-[(4-aminophenyl)methyl]phenyl]carbamate Chemical compound C1=CC(N)=CC=C1CC(C=C1)=CC=C1NC(=O)OCC1=CC=CC=C1 IVQRIMSOKFMBEJ-UHFFFAOYSA-N 0.000 description 2
208000029162 bladder disease Diseases 0.000 description 2
230000031709 bromination Effects 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
235000019282 butylated hydroxyanisole Nutrition 0.000 description 2
229940043253 butylated hydroxyanisole Drugs 0.000 description 2
CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 2
125000006251 butylcarbonyl group Chemical group 0.000 description 2
238000004364 calculation method Methods 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
230000008859 change Effects 0.000 description 2
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
235000019868 cocoa butter Nutrition 0.000 description 2
229940110456 cocoa butter Drugs 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
229940125758 compound 15 Drugs 0.000 description 2
229940126142 compound 16 Drugs 0.000 description 2
229940125878 compound 36 Drugs 0.000 description 2
238000001816 cooling Methods 0.000 description 2
150000001879 copper Chemical class 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
238000011161 development Methods 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
239000000975 dye Substances 0.000 description 2
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
230000002538 fungal effect Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
230000002140 halogenating effect Effects 0.000 description 2
BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 description 2
229960003132 halothane Drugs 0.000 description 2
231100000869 headache Toxicity 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
230000000917 hyperalgesic effect Effects 0.000 description 2
150000002462 imidazolines Chemical class 0.000 description 2
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
238000001802 infusion Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
208000002551 irritable bowel syndrome Diseases 0.000 description 2
208000037906 ischaemic injury Diseases 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
150000002540 isothiocyanates Chemical class 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
235000010445 lecithin Nutrition 0.000 description 2
239000000787 lecithin Substances 0.000 description 2
229940067606 lecithin Drugs 0.000 description 2
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
239000006210 lotion Substances 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000012528 membrane Substances 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
235000010981 methylcellulose Nutrition 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
206010027599 migraine Diseases 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
TXXHDPDFNKHHGW-UHFFFAOYSA-N muconic acid Chemical compound OC(=O)C=CC=CC(O)=O TXXHDPDFNKHHGW-UHFFFAOYSA-N 0.000 description 2
SMUWUPVVTQSUKI-UHFFFAOYSA-N n,n-dimethyl-4-[(4-nitrophenyl)methyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1CC1=CC=C([N+]([O-])=O)C=C1 SMUWUPVVTQSUKI-UHFFFAOYSA-N 0.000 description 2
ZJHMCNGBMCONHZ-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-n'-[5-(2-methylpropyl)-1,3,4-thiadiazol-2-yl]butanediamide Chemical compound S1C(CC(C)C)=NN=C1NC(=O)CCC(=O)NCCC1=CC=C(Cl)C=C1 ZJHMCNGBMCONHZ-UHFFFAOYSA-N 0.000 description 2
BARPTFVGRLHMNR-UHFFFAOYSA-N n-[4-[(4-cyclopentyloxythiophen-2-yl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C=1C=C(NC=2NCCN=2)C=CC=1CC(SC=1)=CC=1OC1CCCC1 BARPTFVGRLHMNR-UHFFFAOYSA-N 0.000 description 2
GKBZVMXIZBRFJN-UHFFFAOYSA-N n-[4-[(5-methoxythiophen-2-yl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound S1C(OC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 GKBZVMXIZBRFJN-UHFFFAOYSA-N 0.000 description 2
HRDACTNYTUBSIS-UHFFFAOYSA-N n-[4-[(5-propan-2-yloxythiophen-2-yl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound S1C(OC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 HRDACTNYTUBSIS-UHFFFAOYSA-N 0.000 description 2
AYEHGPGPHZAVFI-UHFFFAOYSA-N n-[4-[[1-(benzenesulfonyl)piperidin-4-yl]methyl]phenyl]-2,2,2-trifluoroacetamide Chemical compound C1=CC(NC(=O)C(F)(F)F)=CC=C1CC1CCN(S(=O)(=O)C=2C=CC=CC=2)CC1 AYEHGPGPHZAVFI-UHFFFAOYSA-N 0.000 description 2
ISLTYTMRRBUKKF-UHFFFAOYSA-N n-[4-[[1-(benzenesulfonyl)piperidin-4-yl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C=1C=CC=CC=1S(=O)(=O)N(CC1)CCC1CC(C=C1)=CC=C1NC1=NCCN1 ISLTYTMRRBUKKF-UHFFFAOYSA-N 0.000 description 2
PLJBNLLTFXKXAH-UHFFFAOYSA-N n-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]ethanesulfonamide Chemical compound C1=CC(NS(=O)(=O)CC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 PLJBNLLTFXKXAH-UHFFFAOYSA-N 0.000 description 2
WERHDYUYULUEKJ-UHFFFAOYSA-N n-[[4-[(4-aminophenyl)methyl]phenyl]methyl]-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NCC(C=C1)=CC=C1CC1=CC=C(N)C=C1 WERHDYUYULUEKJ-UHFFFAOYSA-N 0.000 description 2
AKQSVPJEFOHLTR-UHFFFAOYSA-N n-benzyl-1-[4-[(4-nitrophenyl)methyl]phenyl]methanesulfonamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC(C=C1)=CC=C1CS(=O)(=O)NCC1=CC=CC=C1 AKQSVPJEFOHLTR-UHFFFAOYSA-N 0.000 description 2
LZQREMCJERTDPM-UHFFFAOYSA-N n-benzyl-1-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]methanesulfonamide Chemical compound C=1C=CC=CC=1CNS(=O)(=O)CC(C=C1)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 LZQREMCJERTDPM-UHFFFAOYSA-N 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
230000008764 nerve damage Effects 0.000 description 2
208000004296 neuralgia Diseases 0.000 description 2
239000002674 ointment Substances 0.000 description 2
238000001543 one-way ANOVA Methods 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
201000008482 osteoarthritis Diseases 0.000 description 2
208000020629 overactive bladder Diseases 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
LMYJGUNNJIDROI-UHFFFAOYSA-N oxan-4-ol Chemical compound OC1CCOCC1 LMYJGUNNJIDROI-UHFFFAOYSA-N 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229940094443 oxytocics prostaglandins Drugs 0.000 description 2
230000003071 parasitic effect Effects 0.000 description 2
239000002245 particle Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
239000006187 pill Substances 0.000 description 2
QQJYAXDCMMXECR-UHFFFAOYSA-N piperidine-1-sulfonyl chloride Chemical compound ClS(=O)(=O)N1CCCCC1 QQJYAXDCMMXECR-UHFFFAOYSA-N 0.000 description 2
231100000572 poisoning Toxicity 0.000 description 2
230000000607 poisoning effect Effects 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
235000015320 potassium carbonate Nutrition 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
108050007059 prostanoid receptors Proteins 0.000 description 2
102000017953 prostanoid receptors Human genes 0.000 description 2
201000007094 prostatitis Diseases 0.000 description 2
230000002685 pulmonary effect Effects 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
230000005855 radiation Effects 0.000 description 2
206010039073 rheumatoid arthritis Diseases 0.000 description 2
125000006413 ring segment Chemical group 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
230000001235 sensitizing effect Effects 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
235000010265 sodium sulphite Nutrition 0.000 description 2
235000013599 spices Nutrition 0.000 description 2
238000013222 sprague-dawley male rat Methods 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
239000013589 supplement Substances 0.000 description 2
238000001356 surgical procedure Methods 0.000 description 2
238000013268 sustained release Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
235000010487 tragacanth Nutrition 0.000 description 2
239000000196 tragacanth Substances 0.000 description 2
229940116362 tragacanth Drugs 0.000 description 2
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
230000009385 viral infection Effects 0.000 description 2
230000003612 virological effect Effects 0.000 description 2
208000009935 visceral pain Diseases 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 1
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
FLXSTOQKSFVUHI-UHFFFAOYSA-N (2-bromo-6-nitrophenyl)-phenylmethanone Chemical compound [O-][N+](=O)C1=CC=CC(Br)=C1C(=O)C1=CC=CC=C1 FLXSTOQKSFVUHI-UHFFFAOYSA-N 0.000 description 1
JDDCDKIWYANHGS-UHFFFAOYSA-N (2-hydroxy-6-nitrophenyl)-phenylmethanone Chemical compound OC1=CC=CC([N+]([O-])=O)=C1C(=O)C1=CC=CC=C1 JDDCDKIWYANHGS-UHFFFAOYSA-N 0.000 description 1
SQPGALHLUVWYQD-UHFFFAOYSA-N (2-methyl-6-nitrophenyl)-phenylmethanone Chemical compound CC1=CC=CC([N+]([O-])=O)=C1C(=O)C1=CC=CC=C1 SQPGALHLUVWYQD-UHFFFAOYSA-N 0.000 description 1
UJHSIDUUJPTLDY-UHFFFAOYSA-N (2-nitrophenyl)-phenylmethanone Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 UJHSIDUUJPTLDY-UHFFFAOYSA-N 0.000 description 1
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-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
WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-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
NBYVSCDYHOKNQJ-UHFFFAOYSA-N (4-fluorophenyl)-(2-nitrophenyl)methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)C1=CC=C(F)C=C1 NBYVSCDYHOKNQJ-UHFFFAOYSA-N 0.000 description 1
ICDAYOOBGHYICW-UHFFFAOYSA-N (4-fluorophenyl)-(4-nitrophenyl)methanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)C1=CC=C(F)C=C1 ICDAYOOBGHYICW-UHFFFAOYSA-N 0.000 description 1
GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
IYCMLBJTAWOWAH-WLHGVMLRSA-N (e)-but-2-enedioic acid;n-[4-[(4-propan-2-ylphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound OC(=O)\C=C\C(O)=O.C1=CC(C(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 IYCMLBJTAWOWAH-WLHGVMLRSA-N 0.000 description 1
HDUZAAGCOXVJOA-WLHGVMLRSA-N (e)-but-2-enedioic acid;n-[4-[[4-(2-methylpropyl)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound OC(=O)\C=C\C(O)=O.C1=CC(CC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 HDUZAAGCOXVJOA-WLHGVMLRSA-N 0.000 description 1
UDSXVCPZAAXSCO-BTJKTKAUSA-N (z)-but-2-enedioic acid;2-[[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenoxy]methyl]propane-1,3-diol Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(OCC(CO)CO)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 UDSXVCPZAAXSCO-BTJKTKAUSA-N 0.000 description 1
LJAPQTTYZKSQOB-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-[4-[[2-fluoro-4-(oxan-2-ylmethoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound OC(=O)\C=C/C(O)=O.C=1C=C(CC=2C=CC(NC=3NCCN=3)=CC=2)C(F)=CC=1OCC1CCCCO1 LJAPQTTYZKSQOB-BTJKTKAUSA-N 0.000 description 1
LYVSNPYUSKXQEP-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-[4-[[4-(2-cyclohexylethoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound OC(=O)\C=C/C(O)=O.C=1C=C(CC=2C=CC(NC=3NCCN=3)=CC=2)C=CC=1OCCC1CCCCC1 LYVSNPYUSKXQEP-BTJKTKAUSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
OBYMZHLTKVXPQF-UHFFFAOYSA-N 1-(chloromethyl)-4-isocyanatobenzene Chemical compound ClCC1=CC=C(N=C=O)C=C1 OBYMZHLTKVXPQF-UHFFFAOYSA-N 0.000 description 1
NPMUAZBRENNCNC-UHFFFAOYSA-N 1-[2-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenoxy]ethyl]imidazolidin-2-one;hydrochloride Chemical compound Cl.O=C1NCCN1CCOC(C=C1)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 NPMUAZBRENNCNC-UHFFFAOYSA-N 0.000 description 1
KPUQTLKSBSIOKA-UHFFFAOYSA-N 1-[4-[[4-(1-amino-4,5-dihydroimidazol-2-yl)phenyl]methyl]piperidin-1-yl]-2-methylpropan-1-one Chemical compound CC(C)C(=O)N1CCC(Cc2ccc(cc2)C2=NCCN2N)CC1 KPUQTLKSBSIOKA-UHFFFAOYSA-N 0.000 description 1
DGOBLGRNQMIQCD-UHFFFAOYSA-N 1-[4-[[4-(1-amino-4,5-dihydroimidazol-2-yl)phenyl]methyl]piperidin-1-yl]-3-methylbutan-1-one Chemical compound CC(C)CC(=O)N1CCC(Cc2ccc(cc2)C2=NCCN2N)CC1 DGOBLGRNQMIQCD-UHFFFAOYSA-N 0.000 description 1
KAGDMZLSUWPAKM-UHFFFAOYSA-N 1-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenoxy]propan-2-ol;hydrochloride Chemical compound Cl.C1=CC(OCC(O)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 KAGDMZLSUWPAKM-UHFFFAOYSA-N 0.000 description 1
WKBWMYQOWVFTOH-UHFFFAOYSA-N 1-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]-n,n-dimethylmethanesulfonamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(CS(=O)(=O)N(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 WKBWMYQOWVFTOH-UHFFFAOYSA-N 0.000 description 1
AAZGIFWGFZPQCE-UHFFFAOYSA-N 1-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]-n-(2-methylpropyl)methanesulfonamide;hydrochloride Chemical compound Cl.C1=CC(CS(=O)(=O)NCC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 AAZGIFWGFZPQCE-UHFFFAOYSA-N 0.000 description 1
KFEGTURYLUBDIR-UHFFFAOYSA-N 1-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]piperidin-1-yl]-4-methylpentan-1-one;hydrochloride Chemical compound Cl.C1CN(C(=O)CCC(C)C)CCC1CC(C=C1)=CC=C1NC1=NCCN1 KFEGTURYLUBDIR-UHFFFAOYSA-N 0.000 description 1
HOLAPQAPVYUPLL-WLHGVMLRSA-N 1-[[4-[[4-(1-amino-4,5-dihydroimidazol-2-yl)phenyl]methyl]phenyl]methyl]-3-phenylurea;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.NN1CCN=C1C(C=C1)=CC=C1CC(C=C1)=CC=C1CNC(=O)NC1=CC=CC=C1 HOLAPQAPVYUPLL-WLHGVMLRSA-N 0.000 description 1
NRPLNCBKEXIMES-UHFFFAOYSA-N 1-azido-2-benzyl-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(N=[N+]=[N-])=C1CC1=CC=CC=C1 NRPLNCBKEXIMES-UHFFFAOYSA-N 0.000 description 1
UPKQTNZSDMAYNO-UHFFFAOYSA-N 1-benzyl-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1CC1=CC=CC=C1 UPKQTNZSDMAYNO-UHFFFAOYSA-N 0.000 description 1
YLRBJYMANQKEAW-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)benzene Chemical compound BrCC1=CC=C(Br)C=C1 YLRBJYMANQKEAW-UHFFFAOYSA-N 0.000 description 1
SGWYZIWUBGPCQC-UHFFFAOYSA-N 1-bromo-4-(butan-2-yloxymethyl)benzene Chemical compound CCC(C)OCC1=CC=C(Br)C=C1 SGWYZIWUBGPCQC-UHFFFAOYSA-N 0.000 description 1
LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
AMMPLVWPWSYRDR-UHFFFAOYSA-N 1-methylbicyclo[2.2.2]oct-2-ene-4-carboxylic acid Chemical compound C1CC2(C(O)=O)CCC1(C)C=C2 AMMPLVWPWSYRDR-UHFFFAOYSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
JDYWOGGVVIWPBL-UHFFFAOYSA-N 2-(chloromethyl)-3-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenoxy]-2-methylpropan-1-ol;hydrochloride Chemical compound Cl.C1=CC(OCC(CO)(CCl)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 JDYWOGGVVIWPBL-UHFFFAOYSA-N 0.000 description 1
ASIAYIWDMKAWDO-UHFFFAOYSA-N 2-[4-[(1-piperidin-1-ylsulfonylpiperidin-4-yl)methyl]phenyl]-4,5-dihydroimidazol-1-amine Chemical compound N1(CCCCC1)S(=O)(=O)N1CCC(CC1)CC1=CC=C(C=C1)C=1N(CCN=1)N ASIAYIWDMKAWDO-UHFFFAOYSA-N 0.000 description 1
SQBCCVOQHFNPOI-UHFFFAOYSA-N 2-[4-[(1-propan-2-ylsulfonylpiperidin-4-yl)methyl]phenyl]-4,5-dihydroimidazol-1-amine Chemical compound CC(C)S(=O)(=O)N1CCC(Cc2ccc(cc2)C2=NCCN2N)CC1 SQBCCVOQHFNPOI-UHFFFAOYSA-N 0.000 description 1
LAAAJCBOARJZNT-UHFFFAOYSA-N 2-[4-[(1-pyrrolidin-1-ylsulfonylpiperidin-4-yl)methyl]phenyl]-4,5-dihydroimidazol-1-amine Chemical compound N1(CCCC1)S(=O)(=O)N1CCC(CC1)CC1=CC=C(C=C1)C=1N(CCN=1)N LAAAJCBOARJZNT-UHFFFAOYSA-N 0.000 description 1
JWLJKPAIUIPDRE-UHFFFAOYSA-N 2-[4-[(4-butan-2-yloxyphenyl)methyl]phenyl]-4,5-dihydroimidazol-1-amine Chemical compound CCC(C)Oc1ccc(Cc2ccc(cc2)C2=NCCN2N)cc1 JWLJKPAIUIPDRE-UHFFFAOYSA-N 0.000 description 1
HHJVFFIBBABUPN-UHFFFAOYSA-N 2-[4-[(4-propan-2-yloxyphenyl)methyl]phenyl]-4,5-dihydroimidazol-1-amine;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC(OC(C)C)=CC=C1CC1=CC=C(C=2N(CCN=2)N)C=C1 HHJVFFIBBABUPN-UHFFFAOYSA-N 0.000 description 1
QVMMDAVFIKAXDE-UHFFFAOYSA-N 2-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenoxy]-1-phenylethanone;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(=O)COC(C=C1)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 QVMMDAVFIKAXDE-UHFFFAOYSA-N 0.000 description 1
QLWPOXSYJMQSQP-UHFFFAOYSA-N 2-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenoxy]-n-(4-methoxyphenyl)acetamide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1NC(=O)COC(C=C1)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 QLWPOXSYJMQSQP-UHFFFAOYSA-N 0.000 description 1
YJAZVDNWRMDLKT-UHFFFAOYSA-N 2-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenoxy]-n-methyl-n-propan-2-ylacetamide;hydrochloride Chemical compound Cl.C1=CC(OCC(=O)N(C)C(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 YJAZVDNWRMDLKT-UHFFFAOYSA-N 0.000 description 1
OJZRYNLWSIUUBI-UHFFFAOYSA-N 2-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenoxy]-n-phenylacetamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1NC(=O)COC(C=C1)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 OJZRYNLWSIUUBI-UHFFFAOYSA-N 0.000 description 1
VWMJIWZZPAUXDU-UHFFFAOYSA-N 2-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 VWMJIWZZPAUXDU-UHFFFAOYSA-N 0.000 description 1
KKEBDELJOZAQRD-UHFFFAOYSA-N 2-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenoxy]propan-1-ol;hydrochloride Chemical compound Cl.C1=CC(OC(CO)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 KKEBDELJOZAQRD-UHFFFAOYSA-N 0.000 description 1
MURVMMYGXGZHDH-UHFFFAOYSA-N 2-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenoxy]propane-1,3-diol;hydrochloride Chemical compound Cl.C1=CC(OC(CO)CO)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 MURVMMYGXGZHDH-UHFFFAOYSA-N 0.000 description 1
HGTUTVLINJVLJJ-UHFFFAOYSA-N 2-[4-[[4-(butan-2-yloxymethyl)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazole;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(COC(C)CC)=CC=C1CC1=CC=C(C=2NCCN=2)C=C1 HGTUTVLINJVLJJ-UHFFFAOYSA-N 0.000 description 1
LJWSSSTWJDFAKQ-UHFFFAOYSA-N 2-[4-[[4-(dimethylsulfamoylamino)phenyl]methyl]anilino]-4,5-dihydro-1h-imidazole;hydrochloride Chemical compound Cl.C1=CC(NS(=O)(=O)N(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 LJWSSSTWJDFAKQ-UHFFFAOYSA-N 0.000 description 1
IYKBNDVVLGTHMH-UHFFFAOYSA-N 2-[4-[[4-(ethylsulfonylmethylamino)phenyl]methyl]phenyl]-4,5-dihydroimidazol-1-amine Chemical compound C(C)S(=O)(=O)CNC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN=2)N)C=C1 IYKBNDVVLGTHMH-UHFFFAOYSA-N 0.000 description 1
XVWTUWWYPXGQTQ-UHFFFAOYSA-N 2-[4-[[4-(oxan-4-yloxy)phenyl]methyl]phenyl]-4,5-dihydroimidazol-1-amine Chemical compound NN1CCN=C1C(C=C1)=CC=C1CC(C=C1)=CC=C1OC1CCOCC1 XVWTUWWYPXGQTQ-UHFFFAOYSA-N 0.000 description 1
BCSHRERPHLTPEE-NRFANRHFSA-N 2-[[5-chloro-2-[[(6s)-6-[4-(2-hydroxyethyl)piperazin-1-yl]-1-methoxy-6,7,8,9-tetrahydro-5h-benzo[7]annulen-2-yl]amino]pyrimidin-4-yl]amino]-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1NC1=NC(NC=2C(=C3CCC[C@@H](CC3=CC=2)N2CCN(CCO)CC2)OC)=NC=C1Cl BCSHRERPHLTPEE-NRFANRHFSA-N 0.000 description 1
QLVGHFBUSGYCCG-UHFFFAOYSA-N 2-amino-n-(1-cyano-2-phenylethyl)acetamide Chemical compound NCC(=O)NC(C#N)CC1=CC=CC=C1 QLVGHFBUSGYCCG-UHFFFAOYSA-N 0.000 description 1
FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 1
YGNKDXXRTJMQHJ-UHFFFAOYSA-N 2-benzyl-1-nitro-3-(sulfonylamino)benzene Chemical compound [O-][N+](=O)C1=CC=CC(N=S(=O)=O)=C1CC1=CC=CC=C1 YGNKDXXRTJMQHJ-UHFFFAOYSA-N 0.000 description 1
UMXDVFXUTDDFAS-UHFFFAOYSA-N 2-benzyl-3-nitrobenzamide Chemical compound NC(=O)C1=CC=CC([N+]([O-])=O)=C1CC1=CC=CC=C1 UMXDVFXUTDDFAS-UHFFFAOYSA-N 0.000 description 1
IZEDTNXLFWARBV-UHFFFAOYSA-N 2-benzyl-3-nitrobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1CC1=CC=CC=C1 IZEDTNXLFWARBV-UHFFFAOYSA-N 0.000 description 1
DDFYNJMBMVETED-UHFFFAOYSA-N 2-benzyl-3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(S(Cl)(=O)=O)=C1CC1=CC=CC=C1 DDFYNJMBMVETED-UHFFFAOYSA-N 0.000 description 1
ACAUJAGLAAHLIR-UHFFFAOYSA-N 2-benzyl-3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1CC1=CC=CC=C1 ACAUJAGLAAHLIR-UHFFFAOYSA-N 0.000 description 1
LAALHHHIGLIVHM-UHFFFAOYSA-N 2-benzyl-3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1CC1=CC=CC=C1 LAALHHHIGLIVHM-UHFFFAOYSA-N 0.000 description 1
FESDHLLVLYZNFY-UHFFFAOYSA-N 2-benzylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1CC1=CC=CC=C1 FESDHLLVLYZNFY-UHFFFAOYSA-N 0.000 description 1
VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-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
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
ZNGINKJHQQQORD-UHFFFAOYSA-N 2-trimethylsilylethanol Chemical compound C[Si](C)(C)CCO ZNGINKJHQQQORD-UHFFFAOYSA-N 0.000 description 1
TYDLXNUCTBUGLP-UHFFFAOYSA-N 2-trimethylsilylethyl n-[4-[[4-(propan-2-yloxymethyl)phenyl]methyl]phenyl]carbamate Chemical compound C1=CC(COC(C)C)=CC=C1CC1=CC=C(NC(=O)OCC[Si](C)(C)C)C=C1 TYDLXNUCTBUGLP-UHFFFAOYSA-N 0.000 description 1
XLZYKTYMLBOINK-UHFFFAOYSA-N 3-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C(=O)C=2C=CC(O)=CC=2)=C1 XLZYKTYMLBOINK-UHFFFAOYSA-N 0.000 description 1
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
IYVFXWHMMGAVRW-UHFFFAOYSA-N 3-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenoxy]propane-1,2-diol;hydrochloride Chemical compound Cl.C1=CC(OCC(O)CO)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 IYVFXWHMMGAVRW-UHFFFAOYSA-N 0.000 description 1
XCMISAPCWHTVNG-UHFFFAOYSA-N 3-bromothiophene Chemical compound BrC=1C=CSC=1 XCMISAPCWHTVNG-UHFFFAOYSA-N 0.000 description 1
ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
CCPUOOUROHGAOD-UHFFFAOYSA-N 3-methoxy-4-nitrobenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC=C1[N+]([O-])=O CCPUOOUROHGAOD-UHFFFAOYSA-N 0.000 description 1
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
HYQCTNVCGRXUAT-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-1-ium-1-amine;chloride Chemical compound Cl.NN1CCN=C1 HYQCTNVCGRXUAT-UHFFFAOYSA-N 0.000 description 1
JAOYYEIRRGTVRI-UHFFFAOYSA-N 4-(4-morpholin-4-ylphenyl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N2CCOCC2)C=C1 JAOYYEIRRGTVRI-UHFFFAOYSA-N 0.000 description 1
JJKRGKFHVADQNV-UHFFFAOYSA-N 4-[(1-piperidin-1-ylsulfonylpiperidin-4-yl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1CCN(S(=O)(=O)N2CCCCC2)CC1 JJKRGKFHVADQNV-UHFFFAOYSA-N 0.000 description 1
JKUKHEWMIYXQRK-UHFFFAOYSA-N 4-[(4-nitrophenyl)methyl]benzenesulfonyl chloride Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC1=CC=C(S(Cl)(=O)=O)C=C1 JKUKHEWMIYXQRK-UHFFFAOYSA-N 0.000 description 1
MNHKUCBXXMFQDM-UHFFFAOYSA-N 4-[(4-nitrophenyl)methyl]pyridine Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC1=CC=NC=C1 MNHKUCBXXMFQDM-UHFFFAOYSA-N 0.000 description 1
DWRWJSPDPPNOHC-UHFFFAOYSA-N 4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]-n,n-di(propan-2-yl)benzenesulfonamide;hydrochloride Chemical compound Cl.C1=CC(S(=O)(=O)N(C(C)C)C(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 DWRWJSPDPPNOHC-UHFFFAOYSA-N 0.000 description 1
WEEKJWKTHJGCHR-UHFFFAOYSA-N 4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]-n-(2-methylpropyl)benzamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(C(=O)NCC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 WEEKJWKTHJGCHR-UHFFFAOYSA-N 0.000 description 1
OMCAVHPJBNIOSK-UHFFFAOYSA-N 4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]-n-(2-methylpropyl)benzenesulfonamide;hydrochloride Chemical compound Cl.C1=CC(S(=O)(=O)NCC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 OMCAVHPJBNIOSK-UHFFFAOYSA-N 0.000 description 1
RQXGDQFYSDOVHB-UHFFFAOYSA-N 4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]-n-propan-2-ylbenzenesulfonamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(S(=O)(=O)NC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 RQXGDQFYSDOVHB-UHFFFAOYSA-N 0.000 description 1
QUPYPUJEPVRLGS-UHFFFAOYSA-N 4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]-n-pyrrolidin-1-ylbenzamide Chemical compound C=1C=C(CC=2C=CC(NC=3NCCN=3)=CC=2)C=CC=1C(=O)NN1CCCC1 QUPYPUJEPVRLGS-UHFFFAOYSA-N 0.000 description 1
XKBZDWYAMCEMRN-UHFFFAOYSA-N 4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenol Chemical compound C1=CC(O)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 XKBZDWYAMCEMRN-UHFFFAOYSA-N 0.000 description 1
IFQUPKAISSPFTE-UHFFFAOYSA-N 4-benzoylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)C1=CC=CC=C1 IFQUPKAISSPFTE-UHFFFAOYSA-N 0.000 description 1
GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
HIHOEGPXVVKJPP-JTQLQIEISA-N 5-fluoro-2-[[(1s)-1-(5-fluoropyridin-2-yl)ethyl]amino]-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyridine-3-carbonitrile Chemical compound N([C@@H](C)C=1N=CC(F)=CC=1)C(C(=CC=1F)C#N)=NC=1NC=1C=C(C)NN=1 HIHOEGPXVVKJPP-JTQLQIEISA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
206010027654 Allergic conditions Diseases 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
229930003347 Atropine Natural products 0.000 description 1
IVRMZWNICZWHMI-UHFFFAOYSA-N Azide Chemical compound [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
LBOAEMJAUHZTSB-UHFFFAOYSA-N C(C(=O)O)(=O)O.FC1=C(C=CC=C1)S(=O)(=O)NCC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1 Chemical compound C(C(=O)O)(=O)O.FC1=C(C=CC=C1)S(=O)(=O)NCC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1 LBOAEMJAUHZTSB-UHFFFAOYSA-N 0.000 description 1
VLKVGWZWXNSECH-UHFFFAOYSA-N C(C(=O)O)(=O)O.FC1=CC=C(C=C1)S(=O)(=O)NCC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1 Chemical compound C(C(=O)O)(=O)O.FC1=CC=C(C=C1)S(=O)(=O)NCC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1 VLKVGWZWXNSECH-UHFFFAOYSA-N 0.000 description 1
VPIDXLJVGVBFOW-UHFFFAOYSA-N C=1C=[C-]PC=1 Chemical class C=1C=[C-]PC=1 VPIDXLJVGVBFOW-UHFFFAOYSA-N 0.000 description 1
BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
208000018380 Chemical injury Diseases 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
CFAJYZUBFLKFNA-UHFFFAOYSA-N Cl.C(C)(C)N(C(=O)COC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1)C(C)C Chemical compound Cl.C(C)(C)N(C(=O)COC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1)C(C)C CFAJYZUBFLKFNA-UHFFFAOYSA-N 0.000 description 1
OAPVPMDPYWIPQR-UHFFFAOYSA-N Cl.C(C)(C)NC(=O)COC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1 Chemical compound Cl.C(C)(C)NC(=O)COC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1 OAPVPMDPYWIPQR-UHFFFAOYSA-N 0.000 description 1
LDXIPUSJBVNECE-UHFFFAOYSA-N Cl.C(C)(C)S(=O)(=O)CNC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1 Chemical compound Cl.C(C)(C)S(=O)(=O)CNC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1 LDXIPUSJBVNECE-UHFFFAOYSA-N 0.000 description 1
AWUIHNTVRFKTCU-UHFFFAOYSA-N Cl.C(C)N(C(=O)COC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1)CC Chemical compound Cl.C(C)N(C(=O)COC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1)CC AWUIHNTVRFKTCU-UHFFFAOYSA-N 0.000 description 1
GJGPDHODHBBURP-UHFFFAOYSA-N Cl.C(C)NC(=O)N1CCC(CC1)CC1=CC=C(C=C1)C=1N(CCN1)N Chemical compound Cl.C(C)NC(=O)N1CCC(CC1)CC1=CC=C(C=C1)C=1N(CCN1)N GJGPDHODHBBURP-UHFFFAOYSA-N 0.000 description 1
STPDWENGZQIKPM-UHFFFAOYSA-N Cl.C(C)OCCOCC1=CC=C(C(C2=CC=C(C=C2)C=2N(CCN2)N)OCC)C=C1 Chemical compound Cl.C(C)OCCOCC1=CC=C(C(C2=CC=C(C=C2)C=2N(CCN2)N)OCC)C=C1 STPDWENGZQIKPM-UHFFFAOYSA-N 0.000 description 1
UQLHTDGQWCMHCD-UHFFFAOYSA-N Cl.C1(CCCC1)NC(=O)COC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1 Chemical compound Cl.C1(CCCC1)NC(=O)COC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1 UQLHTDGQWCMHCD-UHFFFAOYSA-N 0.000 description 1
DJBICELMZOVYLG-UHFFFAOYSA-N Cl.COC1=CC=C(C=C1)S(=O)(=O)NC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1 Chemical compound Cl.COC1=CC=C(C=C1)S(=O)(=O)NC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1 DJBICELMZOVYLG-UHFFFAOYSA-N 0.000 description 1
XWYPBVBCMKHBRO-UHFFFAOYSA-N Cl.FC(CS(=O)(=O)NC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1)(F)F Chemical compound Cl.FC(CS(=O)(=O)NC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1)(F)F XWYPBVBCMKHBRO-UHFFFAOYSA-N 0.000 description 1
XITCCBLRWCUHIS-UHFFFAOYSA-N Cl.N1(CCCCC1)C(=O)COC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1 Chemical compound Cl.N1(CCCCC1)C(=O)COC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1 XITCCBLRWCUHIS-UHFFFAOYSA-N 0.000 description 1
AUMOXNHPJIMHJG-UHFFFAOYSA-N Cl.NN1CCN=C1c1ccc(CC2CCN(CC2)C(=O)Nc2ccccc2)cc1 Chemical compound Cl.NN1CCN=C1c1ccc(CC2CCN(CC2)C(=O)Nc2ccccc2)cc1 AUMOXNHPJIMHJG-UHFFFAOYSA-N 0.000 description 1
VXARIAFRGYNJRX-UHFFFAOYSA-N Cl.O=C1N(CCC1)CCOC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1 Chemical compound Cl.O=C1N(CCC1)CCOC1=CC=C(CC2=CC=C(C=C2)C=2N(CCN2)N)C=C1 VXARIAFRGYNJRX-UHFFFAOYSA-N 0.000 description 1
229920002785 Croscarmellose sodium Polymers 0.000 description 1
102000008130 Cyclic AMP-Dependent Protein Kinases Human genes 0.000 description 1
108010049894 Cyclic AMP-Dependent Protein Kinases Proteins 0.000 description 1
206010063057 Cystitis noninfective Diseases 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
208000009386 Experimental Arthritis Diseases 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
208000018522 Gastrointestinal disease Diseases 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
102100029100 Hematopoietic prostaglandin D synthase Human genes 0.000 description 1
241000282412 Homo Species 0.000 description 1
101000988802 Homo sapiens Hematopoietic prostaglandin D synthase Proteins 0.000 description 1
RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
108090000862 Ion Channels Proteins 0.000 description 1
102000004310 Ion Channels Human genes 0.000 description 1
206010069167 Kounis syndrome Diseases 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
239000000867 Lipoxygenase Inhibitor Substances 0.000 description 1
102000003820 Lipoxygenases Human genes 0.000 description 1
108090000128 Lipoxygenases Proteins 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
208000002720 Malnutrition Diseases 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
238000006751 Mitsunobu reaction Methods 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
TXXHDPDFNKHHGW-CCAGOZQPSA-N Muconic acid Natural products OC(=O)\C=C/C=C\C(O)=O TXXHDPDFNKHHGW-CCAGOZQPSA-N 0.000 description 1
241000699660 Mus musculus Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
IDSGFSCSMXRJON-UHFFFAOYSA-N N-Carbamyl-L-glutamicacid Chemical compound C1=CC([N+](=O)[O-])=CC=C1CC1=CC=CC=C1 IDSGFSCSMXRJON-UHFFFAOYSA-N 0.000 description 1
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
108700023400 Platelet-activating factor receptors Proteins 0.000 description 1
229920001214 Polysorbate 60 Polymers 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
102100026476 Prostacyclin receptor Human genes 0.000 description 1
101710170814 Prostacyclin receptor Proteins 0.000 description 1
102000003923 Protein Kinase C Human genes 0.000 description 1
108090000315 Protein Kinase C Proteins 0.000 description 1
206010037211 Psychomotor hyperactivity Diseases 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
241000283984 Rodentia Species 0.000 description 1
241000607142 Salmonella Species 0.000 description 1
238000003436 Schotten-Baumann reaction Methods 0.000 description 1
206010070834 Sensitisation Diseases 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
206010072005 Spinal pain Diseases 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
238000006619 Stille reaction Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
102000014384 Type C Phospholipases Human genes 0.000 description 1
108010079194 Type C Phospholipases Proteins 0.000 description 1
238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 1
LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
RYHSODLWMJUMBR-UHFFFAOYSA-N [chloro(isocyanato)methyl]benzene Chemical compound O=C=NC(Cl)C1=CC=CC=C1 RYHSODLWMJUMBR-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000009471 action Effects 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
102000030621 adenylate cyclase Human genes 0.000 description 1
108060000200 adenylate cyclase Proteins 0.000 description 1
229910001413 alkali metal ion Inorganic materials 0.000 description 1
229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
150000001351 alkyl iodides Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
SRVFFFJZQVENJC-IHRRRGAJSA-N aloxistatin Chemical compound CCOC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C SRVFFFJZQVENJC-IHRRRGAJSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229960000711 alprostadil Drugs 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
239000002333 angiotensin II receptor antagonist Substances 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
239000000427 antigen Substances 0.000 description 1
102000036639 antigens Human genes 0.000 description 1
108091007433 antigens Proteins 0.000 description 1
239000008365 aqueous carrier Substances 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000004872 arterial blood pressure Effects 0.000 description 1
235000021311 artificial sweeteners Nutrition 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
229960000396 atropine Drugs 0.000 description 1
125000005604 azodicarboxylate group Chemical group 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
UCQVOOALNNXLQS-UHFFFAOYSA-N benzyl n-[4-[[4-(phenylcarbamoylamino)phenyl]methyl]phenyl]carbamate Chemical compound C=1C=C(CC=2C=CC(NC(=O)OCC=3C=CC=CC=3)=CC=2)C=CC=1NC(=O)NC1=CC=CC=C1 UCQVOOALNNXLQS-UHFFFAOYSA-N 0.000 description 1
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
125000001743 benzylic group Chemical group 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
235000013361 beverage Nutrition 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000004768 bromobenzenes Chemical class 0.000 description 1
ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
239000000872 buffer Substances 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
OSVHLUXLWQLPIY-KBAYOESNSA-N butyl 2-[(6aR,9R,10aR)-1-hydroxy-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl]-2-methylpropanoate Chemical compound C(CCC)OC(C(C)(C)C1=CC(=C2[C@H]3[C@H](C(OC2=C1)(C)C)CC[C@H](C3)CO)O)=O OSVHLUXLWQLPIY-KBAYOESNSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001722 carbon compounds Chemical class 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
229960004424 carbon dioxide Drugs 0.000 description 1
QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
239000007806 chemical reaction intermediate Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940125797 compound 12 Drugs 0.000 description 1
229940126543 compound 14 Drugs 0.000 description 1
229940126208 compound 22 Drugs 0.000 description 1
229940125833 compound 23 Drugs 0.000 description 1
229940125961 compound 24 Drugs 0.000 description 1
229940125846 compound 25 Drugs 0.000 description 1
229940127204 compound 29 Drugs 0.000 description 1
229940127573 compound 38 Drugs 0.000 description 1
229940125796 compound 3d Drugs 0.000 description 1
229940125890 compound Ia Drugs 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
230000036461 convulsion Effects 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
229960001681 croscarmellose sodium Drugs 0.000 description 1
235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
230000008021 deposition Effects 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
230000035487 diastolic blood pressure Effects 0.000 description 1
VCJZTATVUDMNLU-UHFFFAOYSA-N dibromomethylbenzene Chemical compound BrC(Br)C1=CC=CC=C1 VCJZTATVUDMNLU-UHFFFAOYSA-N 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
229940042935 dichlorodifluoromethane Drugs 0.000 description 1
DITPMQDQFCSQFL-UHFFFAOYSA-N dichloromethane;4-[(4-nitrophenyl)methyl]benzenesulfonyl chloride Chemical compound ClCCl.C1=CC([N+](=O)[O-])=CC=C1CC1=CC=C(S(Cl)(=O)=O)C=C1 DITPMQDQFCSQFL-UHFFFAOYSA-N 0.000 description 1
229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
OMBRFUXPXNIUCZ-UHFFFAOYSA-N dioxidonitrogen(1+) Chemical class O=[N+]=O OMBRFUXPXNIUCZ-UHFFFAOYSA-N 0.000 description 1
230000006806 disease prevention Effects 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
238000012377 drug delivery Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
210000002615 epidermis Anatomy 0.000 description 1
229960001123 epoprostenol Drugs 0.000 description 1
AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
210000003746 feather Anatomy 0.000 description 1
210000001105 femoral artery Anatomy 0.000 description 1
210000003191 femoral vein Anatomy 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
230000006870 function Effects 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000003349 gelling agent Substances 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
244000144993 groups of animals Species 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
239000002035 hexane extract Substances 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 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
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000005414 inactive ingredient Substances 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
230000006698 induction Effects 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002458 infectious effect Effects 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000003999 initiator Substances 0.000 description 1
229910001867 inorganic solvent Inorganic materials 0.000 description 1
239000003049 inorganic solvent Substances 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
238000001361 intraarterial administration Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007913 intrathecal administration Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical compound O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
239000000644 isotonic solution Substances 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
150000002576 ketones Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
150000002642 lithium compounds Chemical class 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
235000019426 modified starch Nutrition 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
210000004877 mucosa Anatomy 0.000 description 1
210000003097 mucus Anatomy 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
QAPTWHXHEYAIKG-RCOXNQKVSA-N n-[(1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 QAPTWHXHEYAIKG-RCOXNQKVSA-N 0.000 description 1
SBFAIJRNMXJDBD-UHFFFAOYSA-N n-[4-(piperidin-4-ylmethyl)phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C=1C=C(NC=2NCCN=2)C=CC=1CC1CCNCC1 SBFAIJRNMXJDBD-UHFFFAOYSA-N 0.000 description 1
WBIUOKOGSOXTDK-UHFFFAOYSA-N n-[4-[(1-methylsulfonylpiperidin-4-yl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1CN(S(=O)(=O)C)CCC1CC(C=C1)=CC=C1NC1=NCCN1 WBIUOKOGSOXTDK-UHFFFAOYSA-N 0.000 description 1
MAPZKWQAGONNFO-UHFFFAOYSA-N n-[4-[(1-piperidin-1-ylsulfonylpiperidin-4-yl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1CC(CC=2C=CC(NC=3NCCN=3)=CC=2)CCN1S(=O)(=O)N1CCCCC1 MAPZKWQAGONNFO-UHFFFAOYSA-N 0.000 description 1
CWMWTAKFUVKBOP-UHFFFAOYSA-N n-[4-[(2,4-dimethoxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.COC1=CC(OC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 CWMWTAKFUVKBOP-UHFFFAOYSA-N 0.000 description 1
BDOQUKRTRJSDJF-UHFFFAOYSA-N n-[4-[(2-fluoro-4-methoxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.FC1=CC(OC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 BDOQUKRTRJSDJF-UHFFFAOYSA-N 0.000 description 1
DVIPXLIZFIMDQB-UHFFFAOYSA-N n-[4-[(2-fluoro-4-propoxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;oxalic acid Chemical compound OC(=O)C(O)=O.FC1=CC(OCCC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 DVIPXLIZFIMDQB-UHFFFAOYSA-N 0.000 description 1
VEAGNLFLPFWFDL-UHFFFAOYSA-N n-[4-[(3,4-dimethoxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 VEAGNLFLPFWFDL-UHFFFAOYSA-N 0.000 description 1
GVWFREQJSXNGFY-UHFFFAOYSA-N n-[4-[(3-chloro-4-methoxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=C(Cl)C(OC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 GVWFREQJSXNGFY-UHFFFAOYSA-N 0.000 description 1
BGCVGUCNYMTATA-UHFFFAOYSA-N n-[4-[(3-chloro-4-propan-2-yloxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=C(Cl)C(OC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 BGCVGUCNYMTATA-UHFFFAOYSA-N 0.000 description 1
UQCCBCUMPHZICY-UHFFFAOYSA-N n-[4-[(3-fluoro-4-methoxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=C(F)C(OC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 UQCCBCUMPHZICY-UHFFFAOYSA-N 0.000 description 1
NKRUWALETVLUNS-UHFFFAOYSA-N n-[4-[(3-fluoro-4-propan-2-yloxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=C(F)C(OC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 NKRUWALETVLUNS-UHFFFAOYSA-N 0.000 description 1
HTJQVAJLOJHOPA-UHFFFAOYSA-N n-[4-[(4-aminophenyl)methyl]phenyl]-3-chloropropane-1-sulfonamide Chemical compound C1=CC(N)=CC=C1CC1=CC=C(NS(=O)(=O)CCCCl)C=C1 HTJQVAJLOJHOPA-UHFFFAOYSA-N 0.000 description 1
KOVVWBCHDAXITP-UHFFFAOYSA-N n-[4-[(4-butan-2-yloxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=CC(OC(C)CC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 KOVVWBCHDAXITP-UHFFFAOYSA-N 0.000 description 1
ANOVSNCOIIBJNA-UHFFFAOYSA-N n-[4-[(4-butoxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=CC(OCCCC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 ANOVSNCOIIBJNA-UHFFFAOYSA-N 0.000 description 1
LQZMFEHJNGSKNI-UHFFFAOYSA-N n-[4-[(4-butoxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCCCC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 LQZMFEHJNGSKNI-UHFFFAOYSA-N 0.000 description 1
PNGXKMYALKHXRC-UHFFFAOYSA-N n-[4-[(4-cyclohexyloxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C=1C=C(OC2CCCCC2)C=CC=1CC(C=C1)=CC=C1NC1=NCCN1 PNGXKMYALKHXRC-UHFFFAOYSA-N 0.000 description 1
JEWYFMLGUCVXJY-UHFFFAOYSA-N n-[4-[(4-cyclopentyloxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C=1C=C(OC2CCCC2)C=CC=1CC(C=C1)=CC=C1NC1=NCCN1 JEWYFMLGUCVXJY-UHFFFAOYSA-N 0.000 description 1
IMECZUFDOXCNNW-UHFFFAOYSA-N n-[4-[(4-cyclopentyloxythiophen-2-yl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C=1C=C(NC=2NCCN=2)C=CC=1CC(SC=1)=CC=1OC1CCCC1 IMECZUFDOXCNNW-UHFFFAOYSA-N 0.000 description 1
UGSSYVIMTQECGQ-UHFFFAOYSA-N n-[4-[(4-ethoxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1=CC(OCC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 UGSSYVIMTQECGQ-UHFFFAOYSA-N 0.000 description 1
ICXIVGZOVSMBMI-UHFFFAOYSA-N n-[4-[(4-ethylphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=CC(CC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 ICXIVGZOVSMBMI-UHFFFAOYSA-N 0.000 description 1
ZQZKBWQGKCOLGY-UHFFFAOYSA-N n-[4-[(4-fluoro-2-methoxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.COC1=CC(F)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 ZQZKBWQGKCOLGY-UHFFFAOYSA-N 0.000 description 1
XHZCGIRANZZJFD-UHFFFAOYSA-N n-[4-[(4-fluorophenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1=CC(F)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 XHZCGIRANZZJFD-UHFFFAOYSA-N 0.000 description 1
LDMOFLOHTSSUJG-UHFFFAOYSA-N n-[4-[(4-hexoxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OCCCCCC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 LDMOFLOHTSSUJG-UHFFFAOYSA-N 0.000 description 1
LTUAWAFNHHSHLF-UHFFFAOYSA-N n-[4-[(4-methoxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1=CC(OC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 LTUAWAFNHHSHLF-UHFFFAOYSA-N 0.000 description 1
BVYSZICQCQBYQP-UHFFFAOYSA-N n-[4-[(4-morpholin-4-ylphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C=1C=C(N2CCOCC2)C=CC=1CC(C=C1)=CC=C1NC1=NCCN1 BVYSZICQCQBYQP-UHFFFAOYSA-N 0.000 description 1
QBBJQPWZFCITQP-UHFFFAOYSA-N n-[4-[(4-pentan-2-yloxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1=CC(OC(C)CCC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 QBBJQPWZFCITQP-UHFFFAOYSA-N 0.000 description 1
KUYKQWVPAMATOG-UHFFFAOYSA-N n-[4-[(4-pentan-3-yloxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1=CC(OC(CC)CC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 KUYKQWVPAMATOG-UHFFFAOYSA-N 0.000 description 1
VKTJNHRFDBOKFA-UHFFFAOYSA-N n-[4-[(4-phenylmethoxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1COC(C=C1)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 VKTJNHRFDBOKFA-UHFFFAOYSA-N 0.000 description 1
NCVMFOYEDQKDCA-UHFFFAOYSA-N n-[4-[(4-propylphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=CC(CCC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 NCVMFOYEDQKDCA-UHFFFAOYSA-N 0.000 description 1
AQOKBJJXNUMMAD-UHFFFAOYSA-N n-[4-[(4-pyrrolidin-1-ylsulfonylphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C=1C=C(CC=2C=CC(NC=3NCCN=3)=CC=2)C=CC=1S(=O)(=O)N1CCCC1 AQOKBJJXNUMMAD-UHFFFAOYSA-N 0.000 description 1
NEHSNGOEEYTZOB-UHFFFAOYSA-N n-[4-[(5-cyclopentyloxythiophen-2-yl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C=1C=C(NC=2NCCN=2)C=CC=1CC(S1)=CC=C1OC1CCCC1 NEHSNGOEEYTZOB-UHFFFAOYSA-N 0.000 description 1
JVQDVHMOZQEYQS-UHFFFAOYSA-N n-[4-[(5-cyclopentyloxythiophen-2-yl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C=1C=C(NC=2NCCN=2)C=CC=1CC(S1)=CC=C1OC1CCCC1 JVQDVHMOZQEYQS-UHFFFAOYSA-N 0.000 description 1
FZBSFVCYKFIQCL-UHFFFAOYSA-N n-[4-[(5-methoxythiophen-2-yl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;oxalic acid Chemical compound OC(=O)C(O)=O.S1C(OC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 FZBSFVCYKFIQCL-UHFFFAOYSA-N 0.000 description 1
FCGONPBEENGTNP-UHFFFAOYSA-N n-[4-[2-(4-methoxyphenyl)ethoxy-phenylmethyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1=CC(OC)=CC=C1CCOC(C=1C=CC(NC=2NCCN=2)=CC=1)C1=CC=CC=C1 FCGONPBEENGTNP-UHFFFAOYSA-N 0.000 description 1
RFSWHPUXUKFKFQ-UHFFFAOYSA-N n-[4-[[(4-methylsulfonylphenyl)methylamino]-phenylmethyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=CC(S(=O)(=O)C)=CC=C1CNC(C=1C=CC(NC=2NCCN=2)=CC=1)C1=CC=CC=C1 RFSWHPUXUKFKFQ-UHFFFAOYSA-N 0.000 description 1
DIPHQNPMLBNKSX-UHFFFAOYSA-N n-[4-[[2-fluoro-4-(2-methylpropoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.FC1=CC(OCC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 DIPHQNPMLBNKSX-UHFFFAOYSA-N 0.000 description 1
PSUPBJGTTVPGJW-UHFFFAOYSA-N n-[4-[[3-fluoro-4-(2-methylpropoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=C(F)C(OCC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 PSUPBJGTTVPGJW-UHFFFAOYSA-N 0.000 description 1
RZADYPWEFCCSHW-UHFFFAOYSA-N n-[4-[[3-fluoro-4-(oxan-4-ylmethoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C=1C=C(OCC2CCOCC2)C(F)=CC=1CC(C=C1)=CC=C1NC1=NCCN1 RZADYPWEFCCSHW-UHFFFAOYSA-N 0.000 description 1
KFQZQDZRPIRIMX-UHFFFAOYSA-N n-[4-[[4-(1-methoxypropan-2-yloxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=CC(OC(C)COC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 KFQZQDZRPIRIMX-UHFFFAOYSA-N 0.000 description 1
XVZQLTYAGBLHRV-UHFFFAOYSA-N n-[4-[[4-(2,2,2-trifluoroethoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=CC(OCC(F)(F)F)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 XVZQLTYAGBLHRV-UHFFFAOYSA-N 0.000 description 1
ZVKXFPOWQAXCGJ-UHFFFAOYSA-N n-[4-[[4-(2-cyclopentylethoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C=1C=C(CC=2C=CC(NC=3NCCN=3)=CC=2)C=CC=1OCCC1CCCC1 ZVKXFPOWQAXCGJ-UHFFFAOYSA-N 0.000 description 1
CUSMBWJIMCBIHL-UHFFFAOYSA-N n-[4-[[4-(2-ethylsulfonylethylamino)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=CC(NCCS(=O)(=O)CC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 CUSMBWJIMCBIHL-UHFFFAOYSA-N 0.000 description 1
OSDWVOABXFQJLX-UHFFFAOYSA-N n-[4-[[4-(2-methoxyethoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1=CC(OCCOC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 OSDWVOABXFQJLX-UHFFFAOYSA-N 0.000 description 1
WUPCOCBKEQMNJU-UHFFFAOYSA-N n-[4-[[4-(2-methylpropoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=CC(OCC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 WUPCOCBKEQMNJU-UHFFFAOYSA-N 0.000 description 1
SNKUVSMRMODSHB-UHFFFAOYSA-N n-[4-[[4-(2-methylsulfonylethoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=CC(OCCS(=O)(=O)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 SNKUVSMRMODSHB-UHFFFAOYSA-N 0.000 description 1
RKXPFPQTRNGOCG-UHFFFAOYSA-N n-[4-[[4-(2-phenoxyethoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1OCCOC(C=C1)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 RKXPFPQTRNGOCG-UHFFFAOYSA-N 0.000 description 1
SJKJGPLXFLILFL-UHFFFAOYSA-N n-[4-[[4-(2-phenylethoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C=1C=C(CC=2C=CC(NC=3NCCN=3)=CC=2)C=CC=1OCCC1=CC=CC=C1 SJKJGPLXFLILFL-UHFFFAOYSA-N 0.000 description 1
UMUFRDRSEKHPLB-UHFFFAOYSA-N n-[4-[[4-(2-propan-2-yloxyethoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=CC(OCCOC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 UMUFRDRSEKHPLB-UHFFFAOYSA-N 0.000 description 1
NJUOSSZXDNRIQV-UHFFFAOYSA-N n-[4-[[4-(2-thiophen-2-ylethoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C=1C=C(CC=2C=CC(NC=3NCCN=3)=CC=2)C=CC=1OCCC1=CC=CS1 NJUOSSZXDNRIQV-UHFFFAOYSA-N 0.000 description 1
LQMQOIPZWGDWNV-UHFFFAOYSA-N n-[4-[[4-(2-thiophen-3-ylethoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C=1C=C(CC=2C=CC(NC=3NCCN=3)=CC=2)C=CC=1OCCC=1C=CSC=1 LQMQOIPZWGDWNV-UHFFFAOYSA-N 0.000 description 1
HUVBMSDHLIESQW-UHFFFAOYSA-N n-[4-[[4-(3-ethoxypropoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=CC(OCCCOCC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 HUVBMSDHLIESQW-UHFFFAOYSA-N 0.000 description 1
LVGRWQLAYDZBNU-UHFFFAOYSA-N n-[4-[[4-(3-ethylsulfonylpropylamino)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=CC(NCCCS(=O)(=O)CC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 LVGRWQLAYDZBNU-UHFFFAOYSA-N 0.000 description 1
OXPOFGFRIGULEP-UHFFFAOYSA-N n-[4-[[4-(3-methoxybutoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=CC(OCCC(C)OC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 OXPOFGFRIGULEP-UHFFFAOYSA-N 0.000 description 1
LVPWHMJEVCHKDA-UHFFFAOYSA-N n-[4-[[4-(3-methylbutyl)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=CC(CCC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 LVPWHMJEVCHKDA-UHFFFAOYSA-N 0.000 description 1
XUIYZOWYMJUXIY-UHFFFAOYSA-N n-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]-1-phenylmethanesulfonamide;hydrochloride Chemical compound Cl.C=1C=C(CC=2C=CC(NC=3NCCN=3)=CC=2)C=CC=1NS(=O)(=O)CC1=CC=CC=C1 XUIYZOWYMJUXIY-UHFFFAOYSA-N 0.000 description 1
LWPBJNHPDUZKIT-UHFFFAOYSA-N n-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]-2-methylpropanamide;hydrochloride Chemical compound Cl.C1=CC(NC(=O)C(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 LWPBJNHPDUZKIT-UHFFFAOYSA-N 0.000 description 1
ZLYJCQRAQNVKMY-UHFFFAOYSA-N n-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]-4-methylbenzenesulfonamide;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1S(=O)(=O)NC(C=C1)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 ZLYJCQRAQNVKMY-UHFFFAOYSA-N 0.000 description 1
CDXGALJEFVRQCN-UHFFFAOYSA-N n-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]benzenesulfonamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1S(=O)(=O)NC(C=C1)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 CDXGALJEFVRQCN-UHFFFAOYSA-N 0.000 description 1
YTKOSVYJDVHLBD-UHFFFAOYSA-N n-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]butane-1-sulfonamide;hydrochloride Chemical compound Cl.C1=CC(NS(=O)(=O)CCCC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 YTKOSVYJDVHLBD-UHFFFAOYSA-N 0.000 description 1
MHMOEJKIKCJHHI-UHFFFAOYSA-N n-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]ethanesulfonamide;hydrochloride Chemical compound Cl.C1=CC(NS(=O)(=O)CC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 MHMOEJKIKCJHHI-UHFFFAOYSA-N 0.000 description 1
CHBBYUUSSPZZMV-UHFFFAOYSA-N n-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 CHBBYUUSSPZZMV-UHFFFAOYSA-N 0.000 description 1
RZSAXXYNQOLYJN-UHFFFAOYSA-N n-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]oxane-4-carboxamide Chemical compound C1COCCC1C(=O)NC(C=C1)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 RZSAXXYNQOLYJN-UHFFFAOYSA-N 0.000 description 1
KZJXLMAILJWOKV-UHFFFAOYSA-N n-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]propane-1-sulfonamide;hydrochloride Chemical compound Cl.C1=CC(NS(=O)(=O)CCC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 KZJXLMAILJWOKV-UHFFFAOYSA-N 0.000 description 1
XPSTTZOBUOKOIG-UHFFFAOYSA-N n-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]propane-2-sulfonamide;hydrochloride Chemical compound Cl.C1=CC(NS(=O)(=O)C(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 XPSTTZOBUOKOIG-UHFFFAOYSA-N 0.000 description 1
XFVZYFVECDGWAJ-UHFFFAOYSA-N n-[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]thiophene-2-sulfonamide;hydrochloride Chemical compound Cl.C=1C=CSC=1S(=O)(=O)NC(C=C1)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 XFVZYFVECDGWAJ-UHFFFAOYSA-N 0.000 description 1
VRVVBEHOXROAQS-UHFFFAOYSA-N n-[4-[[4-(4-methylcyclohexyl)oxyphenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1CC(C)CCC1OC(C=C1)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 VRVVBEHOXROAQS-UHFFFAOYSA-N 0.000 description 1
ZTLUOSVBBJGTLF-UHFFFAOYSA-N n-[4-[[4-(cyclohexylmethoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1CCCCC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 ZTLUOSVBBJGTLF-UHFFFAOYSA-N 0.000 description 1
XNAXXOQGUWLYKF-UHFFFAOYSA-N n-[4-[[4-(ethylsulfonylmethylamino)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound C1=CC(NCS(=O)(=O)CC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 XNAXXOQGUWLYKF-UHFFFAOYSA-N 0.000 description 1
UCFYVPWVSHKZAJ-UHFFFAOYSA-N n-[4-[[4-(propylsulfonylmethylamino)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=CC(NCS(=O)(=O)CCC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 UCFYVPWVSHKZAJ-UHFFFAOYSA-N 0.000 description 1
MZHMLYJVHZDELV-HFNHQGOYSA-N n-[4-[[4-[(2r)-butan-2-yl]oxyphenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;(z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(O[C@H](C)CC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 MZHMLYJVHZDELV-HFNHQGOYSA-N 0.000 description 1
WKPHJWVSILYTOD-NTISSMGPSA-N n-[4-[[4-[(2s)-2-methylbutoxy]phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C1=CC(OC[C@@H](C)CC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 WKPHJWVSILYTOD-NTISSMGPSA-N 0.000 description 1
MZHMLYJVHZDELV-DASCVMRKSA-N n-[4-[[4-[(2s)-butan-2-yl]oxyphenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;(z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(O[C@@H](C)CC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 MZHMLYJVHZDELV-DASCVMRKSA-N 0.000 description 1
IOEGQQCLDGHZMV-UHFFFAOYSA-N n-[4-[[4-[(5-methyl-1,3-dioxan-5-yl)methoxy]phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine;hydrochloride Chemical compound Cl.C=1C=C(CC=2C=CC(NC=3NCCN=3)=CC=2)C=CC=1OCC1(C)COCOC1 IOEGQQCLDGHZMV-UHFFFAOYSA-N 0.000 description 1
CKNURATYSWRSRX-UHFFFAOYSA-N n-[[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]methyl]-4-methoxybenzenesulfonamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OC)=CC=C1S(=O)(=O)NCC(C=C1)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 CKNURATYSWRSRX-UHFFFAOYSA-N 0.000 description 1
JUTHLKGGVGRFHB-UHFFFAOYSA-N n-[[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]methyl]benzenesulfonamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1S(=O)(=O)NCC(C=C1)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 JUTHLKGGVGRFHB-UHFFFAOYSA-N 0.000 description 1
JVMGDHWXPJAXJV-UHFFFAOYSA-N n-[[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]methyl]propane-1-sulfonamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(CNS(=O)(=O)CCC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 JVMGDHWXPJAXJV-UHFFFAOYSA-N 0.000 description 1
PLTOWZBDGHGJNR-UHFFFAOYSA-N n-[[4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]phenyl]methyl]propane-2-sulfonamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(CNS(=O)(=O)C(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 PLTOWZBDGHGJNR-UHFFFAOYSA-N 0.000 description 1
NSNQFAUOOCAWPQ-UHFFFAOYSA-N n-benzyl-4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]benzenesulfonamide;hydrochloride Chemical compound Cl.C=1C=C(CC=2C=CC(NC=3NCCN=3)=CC=2)C=CC=1S(=O)(=O)NCC1=CC=CC=C1 NSNQFAUOOCAWPQ-UHFFFAOYSA-N 0.000 description 1
FFHAZAPIQSQOMU-UHFFFAOYSA-N n-butyl-4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]benzenesulfonamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(S(=O)(=O)NCCCC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 FFHAZAPIQSQOMU-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
YQCLYEZDVZVAFL-UHFFFAOYSA-N n-tert-butyl-4-[[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]methyl]benzenesulfonamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(S(=O)(=O)NC(C)(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 YQCLYEZDVZVAFL-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
235000021096 natural sweeteners Nutrition 0.000 description 1
230000008035 nerve activity Effects 0.000 description 1
210000001640 nerve ending Anatomy 0.000 description 1
230000007383 nerve stimulation Effects 0.000 description 1
230000003957 neurotransmitter release Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
235000018343 nutrient deficiency Nutrition 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
230000004768 organ dysfunction Effects 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
PAIACQTUAPDCCC-UHFFFAOYSA-N oxalic acid;n-[4-[(4-pentoxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound OC(=O)C(O)=O.C1=CC(OCCCCC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 PAIACQTUAPDCCC-UHFFFAOYSA-N 0.000 description 1
FJFDQNPOYAJEAZ-UHFFFAOYSA-N oxalic acid;n-[4-[(4-propan-2-yloxythiophen-2-yl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound OC(=O)C(O)=O.CC(C)OC1=CSC(CC=2C=CC(NC=3NCCN=3)=CC=2)=C1 FJFDQNPOYAJEAZ-UHFFFAOYSA-N 0.000 description 1
HQKUZUBFWBUJKI-UHFFFAOYSA-N oxalic acid;n-[4-[(4-propoxyphenyl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound OC(=O)C(O)=O.C1=CC(OCCC)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 HQKUZUBFWBUJKI-UHFFFAOYSA-N 0.000 description 1
YJKULZMVCBLFOQ-UHFFFAOYSA-N oxalic acid;n-[4-[(5-propan-2-yloxythiophen-2-yl)methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound OC(=O)C(O)=O.S1C(OC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 YJKULZMVCBLFOQ-UHFFFAOYSA-N 0.000 description 1
JZRIWDHLDKUTON-UHFFFAOYSA-N oxalic acid;n-[4-[[4-(2-propan-2-yloxyethoxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound OC(=O)C(O)=O.C1=CC(OCCOC(C)C)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 JZRIWDHLDKUTON-UHFFFAOYSA-N 0.000 description 1
AZIGHPRFEUMGRA-UHFFFAOYSA-N oxalic acid;n-[4-[[4-(oxan-2-yloxy)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound OC(=O)C(O)=O.C=1C=C(OC2OCCCC2)C=CC=1CC(C=C1)=CC=C1NC1=NCCN1 AZIGHPRFEUMGRA-UHFFFAOYSA-N 0.000 description 1
CMCQAMFBEPDVKL-UHFFFAOYSA-N oxalic acid;n-[4-[[4-(pyrrolidin-1-ylsulfonylmethyl)phenyl]methyl]phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound OC(=O)C(O)=O.C1CCCN1S(=O)(=O)CC(C=C1)=CC=C1CC(C=C1)=CC=C1NC1=NCCN1 CMCQAMFBEPDVKL-UHFFFAOYSA-N 0.000 description 1
238000012856 packing Methods 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
238000005192 partition Methods 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000007310 pathophysiology Effects 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
QARVLSVVCXYDNA-UHFFFAOYSA-N phenyl bromide Natural products BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000003371 phospholipase C inhibitor Substances 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
102000030769 platelet activating factor receptor Human genes 0.000 description 1
229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
235000019252 potassium sulphite Nutrition 0.000 description 1
WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000003380 propellant Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 description 1
GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
JRIQCVWTPGVBBH-UHFFFAOYSA-N pyrrolidine-1-sulfonyl chloride Chemical class ClS(=O)(=O)N1CCCC1 JRIQCVWTPGVBBH-UHFFFAOYSA-N 0.000 description 1
QFYXSLAAXZTRLG-UHFFFAOYSA-N pyrrolidine-2,3-dione Chemical compound O=C1CCNC1=O QFYXSLAAXZTRLG-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000011514 reflex Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
238000012552 review Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
125000005920 sec-butoxy group Chemical group 0.000 description 1
230000028327 secretion Effects 0.000 description 1
230000008313 sensitization Effects 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
230000016160 smooth muscle contraction Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
210000000278 spinal cord Anatomy 0.000 description 1
238000013223 sprague-dawley female rat Methods 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
238000005797 stannylation reaction Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000007885 tablet disintegrant Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
230000008719 thickening Effects 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000009261 transgenic effect Effects 0.000 description 1
238000011830 transgenic mouse model Methods 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
210000000626 ureter Anatomy 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1