BG107132A - Фармацевтично активни пиролидинови производни - Google Patents

Info

Publication number

BG107132A

BG107132A BG107132A BG10713202A BG107132A BG 107132 A BG107132 A BG 107132A BG 107132 A BG107132 A BG 107132A BG 10713202 A BG10713202 A BG 10713202A BG 107132 A BG107132 A BG 107132A

Authority

BG

Bulgaria

Prior art keywords

pyrrolidinecarboxamide

methoxyimino

biphenyl

carbonyl

hydroxy

Prior art date

2000-03-27

Links

• Espacenet
• Global Dossier
• Discuss

• 150000003235 pyrrolidines Chemical class 0.000 title claims abstract description 41
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 52
• 125000003118 aryl group Chemical group 0.000 claims abstract description 45
• 238000000034 method Methods 0.000 claims abstract description 34
• 102000004279 Oxytocin receptors Human genes 0.000 claims abstract description 27
• 108090000876 Oxytocin receptors Proteins 0.000 claims abstract description 27
• 238000002360 preparation method Methods 0.000 claims abstract description 23
• 208000005107 Premature Birth Diseases 0.000 claims abstract description 17
• 208000005171 Dysmenorrhea Diseases 0.000 claims abstract description 14
• 206010013935 Dysmenorrhoea Diseases 0.000 claims abstract description 14
• 230000001404 mediated effect Effects 0.000 claims abstract description 12
• 206010036590 Premature baby Diseases 0.000 claims abstract description 10
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 10
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
• 230000002265 prevention Effects 0.000 claims abstract description 8
• -1 hydroxy, mercapto Chemical class 0.000 claims description 745
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 206
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 174
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 158
• 239000004305 biphenyl Substances 0.000 claims description 102
• 235000010290 biphenyl Nutrition 0.000 claims description 75
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 69
• 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 54
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 52
• 229910052757 nitrogen Inorganic materials 0.000 claims description 37
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 34
• ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 34
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 30
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 29
• 101800000989 Oxytocin Proteins 0.000 claims description 27
• XNOPRXBHLZRZKH-UHFFFAOYSA-N Oxytocin Natural products N1C(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CC(C)C)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(O)C=C1 XNOPRXBHLZRZKH-UHFFFAOYSA-N 0.000 claims description 27
• 102100031951 Oxytocin-neurophysin 1 Human genes 0.000 claims description 27
• XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 claims description 27
• 229960001723 oxytocin Drugs 0.000 claims description 27
• 229920006395 saturated elastomer Polymers 0.000 claims description 27
• 125000001424 substituent group Chemical group 0.000 claims description 26
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 21
• FKCMADOPPWWGNZ-YUMQZZPRSA-N [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O FKCMADOPPWWGNZ-YUMQZZPRSA-N 0.000 claims description 21
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 21
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 20
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 18
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• 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 18
• 238000006243 chemical reaction Methods 0.000 claims description 17
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 17
• ALLIZEAXNXSFGD-UHFFFAOYSA-N 1-methyl-2-phenylbenzene Chemical compound CC1=CC=CC=C1C1=CC=CC=C1 ALLIZEAXNXSFGD-UHFFFAOYSA-N 0.000 claims description 16
• 229910052739 hydrogen Inorganic materials 0.000 claims description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims description 16
• UTMYYLVADKNKHS-UHFFFAOYSA-N CON=C1CCNC1C(N)=O Chemical compound CON=C1CCNC1C(N)=O UTMYYLVADKNKHS-UHFFFAOYSA-N 0.000 claims description 15
• 125000000217 alkyl group Chemical group 0.000 claims description 15
• 229910052736 halogen Inorganic materials 0.000 claims description 14
• 150000002367 halogens Chemical class 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 150000003839 salts Chemical class 0.000 claims description 14
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 13
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 13
• 230000027455 binding Effects 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 125000002252 acyl group Chemical group 0.000 claims description 12
• 239000001257 hydrogen Substances 0.000 claims description 12
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
• 125000003107 substituted aryl group Chemical group 0.000 claims description 12
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 11
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 11
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
• 108090000765 processed proteins & peptides Proteins 0.000 claims description 11
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
• KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 9
• 239000011230 binding agent Substances 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• 125000005309 thioalkoxy group Chemical group 0.000 claims description 9
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 125000000981 3-amino-3-oxopropyl group Chemical group [H]C([*])([H])C([H])([H])C(=O)N([H])[H] 0.000 claims description 7
• 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 6
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 6
• 230000003042 antagnostic effect Effects 0.000 claims description 6
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
• 125000004432 carbon atom Chemical group C* 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 5
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 125000006239 protecting group Chemical group 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 102000005962 receptors Human genes 0.000 claims description 5
• 108020003175 receptors Proteins 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• WWBGFXQEZKPQFW-UHFFFAOYSA-N 1-(2,2-diphenylacetyl)pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 WWBGFXQEZKPQFW-UHFFFAOYSA-N 0.000 claims description 4
• JGERLVYILSRONJ-UHFFFAOYSA-N 1-[4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound CC1=CC=CC=C1C1=CC=C(C(=O)N2C(CCC2)C(N)=O)C=C1 JGERLVYILSRONJ-UHFFFAOYSA-N 0.000 claims description 4
• 125000004442 acylamino group Chemical group 0.000 claims description 4
• 125000004423 acyloxy group Chemical group 0.000 claims description 4
• 125000001118 alkylidene group Chemical group 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• VLJNHYLEOZPXFW-UHFFFAOYSA-N pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1 VLJNHYLEOZPXFW-UHFFFAOYSA-N 0.000 claims description 4
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
• 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 3
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 3
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 3
• 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 3
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 3
• XIXRUEBBHFCTRF-UHFFFAOYSA-N 1-(4-pyridin-3-ylbenzoyl)pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1C(=O)C1=CC=C(C=2C=NC=CC=2)C=C1 XIXRUEBBHFCTRF-UHFFFAOYSA-N 0.000 claims description 3
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 3
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 3
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
• 229910052794 bromium Inorganic materials 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000001041 indolyl group Chemical group 0.000 claims description 3
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
• 125000002971 oxazolyl group Chemical group 0.000 claims description 3
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000005493 quinolyl group Chemical group 0.000 claims description 3
• 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 3
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 3
• 125000001302 tertiary amino group Chemical group 0.000 claims description 3
• 125000000335 thiazolyl group Chemical group 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 2
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 2
• 230000000903 blocking effect Effects 0.000 claims description 2
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
• 229910052799 carbon Inorganic materials 0.000 claims description 2
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 208000035475 disorder Diseases 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000005990 isobenzothienyl group Chemical group 0.000 claims description 2
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 2
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 2
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 2
• 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
• 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 2
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
• ZAXLCZWBAWDNPZ-SANMLTNESA-N (4-hydroxy-4-phenylpiperidin-1-yl)-[(2S)-4-methoxyimino-1-(4-pyridin-3-ylbenzoyl)pyrrolidin-2-yl]methanone Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CCC(CC1)(C1=CC=CC=C1)O)C(C1=CC=C(C=C1)C=1C=NC=CC=1)=O ZAXLCZWBAWDNPZ-SANMLTNESA-N 0.000 claims 1
• ZPCQUOAPUIJCMW-UHFFFAOYSA-N 2-(2,1,3-benzothiadiazol-4-yl)-4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound N=1SN=C2C=1C=CC=C2C1(N(CC(C1)=NOC)C(=O)C1=CC=C(C=C1)C1=CC=CC=C1)C(=O)N ZPCQUOAPUIJCMW-UHFFFAOYSA-N 0.000 claims 1
• 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
• SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims 1
• 125000003368 amide group Chemical group 0.000 claims 1
• VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 claims 1
• AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 claims 1
• 150000001875 compounds Chemical class 0.000 abstract description 542
• 230000000694 effects Effects 0.000 abstract description 23
• 239000005557 antagonist Substances 0.000 abstract description 7
• 208000006399 Premature Obstetric Labor Diseases 0.000 abstract description 4
• 206010036600 Premature labour Diseases 0.000 abstract description 3
• 208000026440 premature labor Diseases 0.000 abstract description 3
• 230000006806 disease prevention Effects 0.000 abstract description 2
• 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 abstract 1
• 238000004949 mass spectrometry Methods 0.000 description 681
• 238000007429 general method Methods 0.000 description 439
• 238000004128 high performance liquid chromatography Methods 0.000 description 183
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 141
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 83
• 239000000243 solution Substances 0.000 description 73
• OXEUETBFKVCRNP-UHFFFAOYSA-N 9-ethyl-3-carbazolamine Chemical compound NC1=CC=C2N(CC)C3=CC=CC=C3C2=C1 OXEUETBFKVCRNP-UHFFFAOYSA-N 0.000 description 65
• 125000005336 allyloxy group Chemical group 0.000 description 57
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
• 239000000203 mixture Substances 0.000 description 52
• JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 50
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
• 238000005481 NMR spectroscopy Methods 0.000 description 46
• 239000011541 reaction mixture Substances 0.000 description 43
• 239000000047 product Substances 0.000 description 40
• 239000000543 intermediate Substances 0.000 description 31
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
• 239000002904 solvent Substances 0.000 description 30
• 235000019439 ethyl acetate Nutrition 0.000 description 29
• MSYLETHDEIJMAF-UHFFFAOYSA-N 2,2-diphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(C(=O)Cl)C1=CC=CC=C1 MSYLETHDEIJMAF-UHFFFAOYSA-N 0.000 description 28
• 239000002253 acid Substances 0.000 description 27
• ULLGRIBXGPATMA-QMMMGPOBSA-N (2s)-4-methylidene-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CC(=C)C[C@H]1C(O)=O ULLGRIBXGPATMA-QMMMGPOBSA-N 0.000 description 25
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 23
• ALBQXDHCMLLQMB-UHFFFAOYSA-N 4-phenylbenzenesulfonyl chloride Chemical compound C1=CC(S(=O)(=O)Cl)=CC=C1C1=CC=CC=C1 ALBQXDHCMLLQMB-UHFFFAOYSA-N 0.000 description 22
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 22
• JKBGXBVHOKKEJO-UHFFFAOYSA-N 2-oxo-6-pentylpyran-3-carbonyl chloride Chemical compound CCCCCC1=CC=C(C(Cl)=O)C(=O)O1 JKBGXBVHOKKEJO-UHFFFAOYSA-N 0.000 description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• RJSRSRITMWVIQT-UHFFFAOYSA-N quinolin-6-amine Chemical compound N1=CC=CC2=CC(N)=CC=C21 RJSRSRITMWVIQT-UHFFFAOYSA-N 0.000 description 21
• 239000007787 solid Substances 0.000 description 21
• NDNIPPKLIDCYGD-UHFFFAOYSA-N 4-(2-methylphenyl)benzoic acid Chemical compound CC1=CC=CC=C1C1=CC=C(C(O)=O)C=C1 NDNIPPKLIDCYGD-UHFFFAOYSA-N 0.000 description 20
• 238000004440 column chromatography Methods 0.000 description 20
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 17
• 239000012044 organic layer Substances 0.000 description 17
• 238000003786 synthesis reaction Methods 0.000 description 17
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 16
• 230000015572 biosynthetic process Effects 0.000 description 16
• 239000003921 oil Substances 0.000 description 16
• ZKWYUNRBXBVNTO-UHFFFAOYSA-N NC(=O)C1C(=NOC)CCN1C(=O)C1=CC=C(C=2C(=CC=CC=2)C)C=C1 Chemical compound NC(=O)C1C(=NOC)CCN1C(=O)C1=CC=C(C=2C(=CC=CC=2)C)C=C1 ZKWYUNRBXBVNTO-UHFFFAOYSA-N 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
• 235000019341 magnesium sulphate Nutrition 0.000 description 15
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 14
• 239000012267 brine Substances 0.000 description 14
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 14
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 14
• 238000000746 purification Methods 0.000 description 14
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
• VRVUKQWNRPNACD-UHFFFAOYSA-N 1-isocyanatopentane Chemical compound CCCCCN=C=O VRVUKQWNRPNACD-UHFFFAOYSA-N 0.000 description 13
• PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 13
• GYUKEVKPDRXPAB-UHFFFAOYSA-N 4-pyridin-3-ylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CN=C1 GYUKEVKPDRXPAB-UHFFFAOYSA-N 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
• DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 13
• NVSYANRBXPURRQ-UHFFFAOYSA-N naphthalen-1-ylmethanamine Chemical compound C1=CC=C2C(CN)=CC=CC2=C1 NVSYANRBXPURRQ-UHFFFAOYSA-N 0.000 description 13
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
• DIVNUTGTTIRPQA-UHFFFAOYSA-N (3,4-dimethoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1OC DIVNUTGTTIRPQA-UHFFFAOYSA-N 0.000 description 11
• USEDMAWWQDFMFY-UHFFFAOYSA-N 4-cyanobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(C#N)C=C1 USEDMAWWQDFMFY-UHFFFAOYSA-N 0.000 description 11
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 11
• 239000012346 acetyl chloride Substances 0.000 description 11
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
• GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 10
• NPOVTGVGOBJZPY-UHFFFAOYSA-N 1-isocyanato-3-methoxybenzene Chemical compound COC1=CC=CC(N=C=O)=C1 NPOVTGVGOBJZPY-UHFFFAOYSA-N 0.000 description 10
• VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 10
• HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 10
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
• 239000003795 chemical substances by application Substances 0.000 description 10
• 238000003818 flash chromatography Methods 0.000 description 10
• 238000012360 testing method Methods 0.000 description 10
• XEFUJGURFLOFAN-UHFFFAOYSA-N 1,3-dichloro-5-isocyanatobenzene Chemical compound ClC1=CC(Cl)=CC(N=C=O)=C1 XEFUJGURFLOFAN-UHFFFAOYSA-N 0.000 description 9
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 9
• JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 9
• ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 9
• LRGHHVXWOZHPJF-UHFFFAOYSA-N 4-(dimethylamino)butanoyl chloride Chemical compound CN(C)CCCC(Cl)=O LRGHHVXWOZHPJF-UHFFFAOYSA-N 0.000 description 9
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
• 210000004027 cell Anatomy 0.000 description 9
• 239000013058 crude material Substances 0.000 description 9
• 239000000843 powder Substances 0.000 description 9
• 229920005989 resin Polymers 0.000 description 9
• 239000011347 resin Substances 0.000 description 9
• FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 9
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
• DRLGIZIAMHIQHL-UHFFFAOYSA-N 2,1,3-benzothiadiazol-4-amine Chemical compound NC1=CC=CC2=NSN=C12 DRLGIZIAMHIQHL-UHFFFAOYSA-N 0.000 description 8
• AOOZVQGGMFGGEE-UHFFFAOYSA-N 4-phenoxybenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1OC1=CC=CC=C1 AOOZVQGGMFGGEE-UHFFFAOYSA-N 0.000 description 8
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
• CKYGSXRXTIKGAJ-ZETCQYMHSA-N Boc-L-Pro(4-oxo) Chemical compound CC(C)(C)OC(=O)N1CC(=O)C[C@H]1C(O)=O CKYGSXRXTIKGAJ-ZETCQYMHSA-N 0.000 description 8
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• 150000001412 amines Chemical class 0.000 description 8
• LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 8
• 238000004587 chromatography analysis Methods 0.000 description 8
• 238000001914 filtration Methods 0.000 description 8
• 238000000926 separation method Methods 0.000 description 8
• 239000000741 silica gel Substances 0.000 description 8
• 229910002027 silica gel Inorganic materials 0.000 description 8
• BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 7
• GDMZHPUPLWQIBD-UHFFFAOYSA-N 2-pyrrol-1-ylaniline Chemical compound NC1=CC=CC=C1N1C=CC=C1 GDMZHPUPLWQIBD-UHFFFAOYSA-N 0.000 description 7
• KXJMVLOPRWOQOJ-UHFFFAOYSA-N 3-methoxyimino-1-(4-pyridin-3-ylbenzoyl)pyrrolidine-2-carboxamide Chemical compound NC(=O)C1C(=NOC)CCN1C(=O)C1=CC=C(C=2C=NC=CC=2)C=C1 KXJMVLOPRWOQOJ-UHFFFAOYSA-N 0.000 description 7
• 239000005711 Benzoic acid Substances 0.000 description 7
• 235000010233 benzoic acid Nutrition 0.000 description 7
• 239000003153 chemical reaction reagent Substances 0.000 description 7
• 150000001805 chlorine compounds Chemical class 0.000 description 7
• BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 7
• 201000010099 disease Diseases 0.000 description 7
• 239000002552 dosage form Substances 0.000 description 7
• 230000005764 inhibitory process Effects 0.000 description 7
• 239000010410 layer Substances 0.000 description 7
• 239000002609 medium Substances 0.000 description 7
• CPPGZWWUPFWALU-UHFFFAOYSA-N 1-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(N=C=O)=C1 CPPGZWWUPFWALU-UHFFFAOYSA-N 0.000 description 6
• VRBVHQUSAOKVDH-UHFFFAOYSA-N 2-(4-chlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=C(Cl)C=C1 VRBVHQUSAOKVDH-UHFFFAOYSA-N 0.000 description 6
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
• DZLGZIGLHCRIMF-UHFFFAOYSA-N 4-pyridin-4-ylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=NC=C1 DZLGZIGLHCRIMF-UHFFFAOYSA-N 0.000 description 6
• 101000986765 Homo sapiens Oxytocin receptor Proteins 0.000 description 6
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
• 125000003342 alkenyl group Chemical group 0.000 description 6
• 125000000304 alkynyl group Chemical group 0.000 description 6
• 239000002585 base Substances 0.000 description 6
• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
• 239000002775 capsule Substances 0.000 description 6
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
• 150000001735 carboxylic acids Chemical class 0.000 description 6
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 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
• 125000000547 substituted alkyl group Chemical group 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• 238000001308 synthesis method Methods 0.000 description 6
• ZILSBZLQGRBMOR-UHFFFAOYSA-N 1,3-benzodioxol-5-ylmethanamine Chemical compound NCC1=CC=C2OCOC2=C1 ZILSBZLQGRBMOR-UHFFFAOYSA-N 0.000 description 5
• 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 description 5
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 5
• LDNLTMRRJNZNRE-UHFFFAOYSA-N 4-(2,6-dimethylphenyl)benzoic acid Chemical compound CC1=CC=CC(C)=C1C1=CC=C(C(O)=O)C=C1 LDNLTMRRJNZNRE-UHFFFAOYSA-N 0.000 description 5
• AQIPNZHMXANQRC-UHFFFAOYSA-N 4-pyridin-2-ylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=N1 AQIPNZHMXANQRC-UHFFFAOYSA-N 0.000 description 5
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
• 241000124008 Mammalia Species 0.000 description 5
• 208000036029 Uterine contractions during pregnancy Diseases 0.000 description 5
• 238000004166 bioassay Methods 0.000 description 5
• ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
• 238000002347 injection Methods 0.000 description 5
• 239000007924 injection Substances 0.000 description 5
• KKHUSADXXDNRPW-UHFFFAOYSA-N malonic anhydride Chemical compound O=C1CC(=O)O1 KKHUSADXXDNRPW-UHFFFAOYSA-N 0.000 description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
• UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 5
• 125000003544 oxime group Chemical group 0.000 description 5
• 239000003336 oxytocin antagonist Substances 0.000 description 5
• 229940121361 oxytocin antagonists Drugs 0.000 description 5
• DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 5
• PXFJLKKZSWWVRX-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)piperazine Chemical compound C1=C(Cl)C(Cl)=CC=C1N1CCNCC1 PXFJLKKZSWWVRX-UHFFFAOYSA-N 0.000 description 4
• UPBHYYJZVWZCOZ-QMMMGPOBSA-N 1-o-tert-butyl 2-o-methyl (2s)-4-oxopyrrolidine-1,2-dicarboxylate Chemical compound COC(=O)[C@@H]1CC(=O)CN1C(=O)OC(C)(C)C UPBHYYJZVWZCOZ-QMMMGPOBSA-N 0.000 description 4
• WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 4
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 4
• MZIFVOLYXURHDM-UHFFFAOYSA-N 4-(2-cyanophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1C#N MZIFVOLYXURHDM-UHFFFAOYSA-N 0.000 description 4
• YQLGXBYAHYGABI-UHFFFAOYSA-N 4-(2-methoxyphenyl)benzoic acid Chemical compound COC1=CC=CC=C1C1=CC=C(C(O)=O)C=C1 YQLGXBYAHYGABI-UHFFFAOYSA-N 0.000 description 4
• RAFOEQLLARZUAM-UHFFFAOYSA-N 4-methoxyiminopyrrolidine-2-carboxamide Chemical compound CON=C1CNC(C(N)=O)C1 RAFOEQLLARZUAM-UHFFFAOYSA-N 0.000 description 4
• KQKFQBTWXOGINC-UHFFFAOYSA-N 4-phenylpiperidin-4-ol Chemical compound C=1C=CC=CC=1C1(O)CCNCC1 KQKFQBTWXOGINC-UHFFFAOYSA-N 0.000 description 4
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
• OUVXYXNWSVIOSJ-UHFFFAOYSA-N Fluo-4 Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(OCCOC=2C(=CC=C(C=2)C2=C3C=C(F)C(=O)C=C3OC3=CC(O)=C(F)C=C32)N(CC(O)=O)CC(O)=O)=C1 OUVXYXNWSVIOSJ-UHFFFAOYSA-N 0.000 description 4
• 108010010803 Gelatin Proteins 0.000 description 4
• 241000282412 Homo Species 0.000 description 4
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• ULSIYEODSMZIPX-UHFFFAOYSA-N alpha-hydroxyphenethylamine Natural products NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 4
• 235000019270 ammonium chloride Nutrition 0.000 description 4
• 239000000872 buffer Substances 0.000 description 4
• 239000000460 chlorine Substances 0.000 description 4
• 239000011248 coating agent Substances 0.000 description 4
• 238000000576 coating method Methods 0.000 description 4
• 125000000524 functional group Chemical group 0.000 description 4
• 229920000159 gelatin Polymers 0.000 description 4
• 239000008273 gelatin Substances 0.000 description 4
• 235000019322 gelatine Nutrition 0.000 description 4
• 235000011852 gelatine desserts Nutrition 0.000 description 4
• BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 4
• 230000007062 hydrolysis Effects 0.000 description 4
• 238000006460 hydrolysis reaction Methods 0.000 description 4
• 238000000338 in vitro Methods 0.000 description 4
• 230000001965 increasing effect Effects 0.000 description 4
• 229910052740 iodine Inorganic materials 0.000 description 4
• 239000012948 isocyanate Substances 0.000 description 4
• 150000002513 isocyanates Chemical class 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• GHFGJTVYMNRGBY-UHFFFAOYSA-N m-tyramine Chemical compound NCCC1=CC=CC(O)=C1 GHFGJTVYMNRGBY-UHFFFAOYSA-N 0.000 description 4
• RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• 150000003180 prostaglandins Chemical class 0.000 description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
• 229910000104 sodium hydride Inorganic materials 0.000 description 4
• 238000010532 solid phase synthesis reaction Methods 0.000 description 4
• 239000007858 starting material Substances 0.000 description 4
• 238000003756 stirring Methods 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
• DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 4
• 210000004291 uterus Anatomy 0.000 description 4
• 229940045860 white wax Drugs 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
• NBOOZXVYXHATOW-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-ylmethyl)piperazine Chemical compound C=1C=C2OCOC2=CC=1CN1CCNCC1 NBOOZXVYXHATOW-UHFFFAOYSA-N 0.000 description 3
• XUSXTHMTOSFZII-UHFFFAOYSA-N 1-(aminomethyl)cyclohexan-1-ol Chemical compound NCC1(O)CCCCC1 XUSXTHMTOSFZII-UHFFFAOYSA-N 0.000 description 3
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
• KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 3
• NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• JBHAFODHURIGOL-UHFFFAOYSA-N CON=C1C(NCC1)C(=O)O Chemical compound CON=C1C(NCC1)C(=O)O JBHAFODHURIGOL-UHFFFAOYSA-N 0.000 description 3
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• 229940122828 Oxytocin receptor antagonist Drugs 0.000 description 3
• WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 3
• 241000700159 Rattus Species 0.000 description 3
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
• 235000011054 acetic acid Nutrition 0.000 description 3
• 230000002378 acidificating effect Effects 0.000 description 3
• HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 3
• 239000000048 adrenergic agonist Substances 0.000 description 3
• 239000000556 agonist Substances 0.000 description 3
• 238000004458 analytical method Methods 0.000 description 3
• GMWFCJXSQQHBPI-UHFFFAOYSA-N azetidin-3-ol Chemical compound OC1CNC1 GMWFCJXSQQHBPI-UHFFFAOYSA-N 0.000 description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
• RSDOASZYYCOXIB-UHFFFAOYSA-N beta-alaninamide Chemical compound NCCC(N)=O RSDOASZYYCOXIB-UHFFFAOYSA-N 0.000 description 3
• 235000013877 carbamide Nutrition 0.000 description 3
• AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 3
• KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 3
• 239000012230 colorless oil Substances 0.000 description 3
• 230000000052 comparative effect Effects 0.000 description 3
• 238000002474 experimental method Methods 0.000 description 3
• 239000000796 flavoring agent Substances 0.000 description 3
• 230000006870 function Effects 0.000 description 3
• AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 3
• 239000004615 ingredient Substances 0.000 description 3
• 229960000367 inositol Drugs 0.000 description 3
• 238000001990 intravenous administration Methods 0.000 description 3
• 150000002540 isothiocyanates Chemical class 0.000 description 3
• 238000011068 loading method Methods 0.000 description 3
• 239000000314 lubricant Substances 0.000 description 3
• 235000019359 magnesium stearate Nutrition 0.000 description 3
• 238000012986 modification Methods 0.000 description 3
• 230000004048 modification Effects 0.000 description 3
• AXMJAJPZBCQNLP-UHFFFAOYSA-N n-methoxypyrrolidin-3-imine Chemical compound CON=C1CCNC1 AXMJAJPZBCQNLP-UHFFFAOYSA-N 0.000 description 3
• 150000002923 oximes Chemical class 0.000 description 3
• 229940094443 oxytocics prostaglandins Drugs 0.000 description 3
• HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
• 238000007127 saponification reaction Methods 0.000 description 3
• 239000011780 sodium chloride Substances 0.000 description 3
• 239000012312 sodium hydride Substances 0.000 description 3
• 229940124530 sulfonamide Drugs 0.000 description 3
• 150000003456 sulfonamides Chemical class 0.000 description 3
• 238000013268 sustained release Methods 0.000 description 3
• 239000012730 sustained-release form Substances 0.000 description 3
• 150000003512 tertiary amines Chemical class 0.000 description 3
• ULSIYEODSMZIPX-QMMMGPOBSA-N (1r)-2-amino-1-phenylethanol Chemical compound NC[C@H](O)C1=CC=CC=C1 ULSIYEODSMZIPX-QMMMGPOBSA-N 0.000 description 2
• ULSIYEODSMZIPX-MRVPVSSYSA-N (1s)-2-amino-1-phenylethanol Chemical compound NC[C@@H](O)C1=CC=CC=C1 ULSIYEODSMZIPX-MRVPVSSYSA-N 0.000 description 2
• HXKKHQJGJAFBHI-VKHMYHEASA-N (2s)-1-aminopropan-2-ol Chemical compound C[C@H](O)CN HXKKHQJGJAFBHI-VKHMYHEASA-N 0.000 description 2
• BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 2
• QHGUCRYDKWKLMG-MRVPVSSYSA-N (S)-octopamine Chemical compound NC[C@@H](O)C1=CC=C(O)C=C1 QHGUCRYDKWKLMG-MRVPVSSYSA-N 0.000 description 2
• LNOLJFCCYQZFBQ-BUHFOSPRSA-N (ne)-n-[(4-nitrophenyl)-phenylmethylidene]hydroxylamine Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(=N/O)/C1=CC=CC=C1 LNOLJFCCYQZFBQ-BUHFOSPRSA-N 0.000 description 2
• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
• XPXXRPJWTVSNHX-UHFFFAOYSA-N 1-(2-oxo-6-pentylpyran-3-carbonyl)pyrrolidine-2-carboxamide Chemical compound O=C1OC(=CC=C1C(=O)N1C(CCC1)C(=O)N)CCCCC XPXXRPJWTVSNHX-UHFFFAOYSA-N 0.000 description 2
• NLWCWEGVNJVLAX-UHFFFAOYSA-N 1-methoxy-2-phenylbenzene Chemical compound COC1=CC=CC=C1C1=CC=CC=C1 NLWCWEGVNJVLAX-UHFFFAOYSA-N 0.000 description 2
• PKDPUENCROCRCH-UHFFFAOYSA-N 1-piperazin-1-ylethanone Chemical compound CC(=O)N1CCNCC1 PKDPUENCROCRCH-UHFFFAOYSA-N 0.000 description 2
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 2
• PMVYCIJOHUIJLP-UHFFFAOYSA-N 1-quinolin-6-ylpyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1C1=CC=C(N=CC=C2)C2=C1 PMVYCIJOHUIJLP-UHFFFAOYSA-N 0.000 description 2
• XNIOWJUQPMKCIJ-UHFFFAOYSA-N 2-(benzylamino)ethanol Chemical compound OCCNCC1=CC=CC=C1 XNIOWJUQPMKCIJ-UHFFFAOYSA-N 0.000 description 2
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
• CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
• ZRVFFIXOCFUHDA-UHFFFAOYSA-N 2-ethoxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(OCC)=CC=C21 ZRVFFIXOCFUHDA-UHFFFAOYSA-N 0.000 description 2
• LZGDLTYIHXNYJS-UHFFFAOYSA-N 2-methyl-4-(2-methylphenyl)benzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC(C=2C(=CC=CC=2)C)=C1 LZGDLTYIHXNYJS-UHFFFAOYSA-N 0.000 description 2
• PFXXTYUSZRFQHC-UHFFFAOYSA-N 2-methylhept-5-enamide Chemical compound CC=CCCC(C)C(N)=O PFXXTYUSZRFQHC-UHFFFAOYSA-N 0.000 description 2
• 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 2
• VAYMIYBJLRRIFR-UHFFFAOYSA-N 2-tolyl isocyanate Chemical compound CC1=CC=CC=C1N=C=O VAYMIYBJLRRIFR-UHFFFAOYSA-N 0.000 description 2
• KUZNURGIXXKBEJ-UHFFFAOYSA-N 3-(4-methylphenyl)pyridine Chemical compound C1=CC(C)=CC=C1C1=CC=CN=C1 KUZNURGIXXKBEJ-UHFFFAOYSA-N 0.000 description 2
• XPZYMRGPCVWBRW-UHFFFAOYSA-N 3-methoxyimino-1-(3-phenoxybenzoyl)pyrrolidine-2-carboxamide Chemical compound NC(=O)C1C(=NOC)CCN1C(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 XPZYMRGPCVWBRW-UHFFFAOYSA-N 0.000 description 2
• LVFRCHIUUKWBLR-UHFFFAOYSA-N 4,6-dimethoxypyrimidin-2-amine Chemical compound COC1=CC(OC)=NC(N)=N1 LVFRCHIUUKWBLR-UHFFFAOYSA-N 0.000 description 2
• UQTIMPXCTPPTSJ-UHFFFAOYSA-N 4-(1-oxidopyridin-1-ium-3-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C[N+]([O-])=C1 UQTIMPXCTPPTSJ-UHFFFAOYSA-N 0.000 description 2
• AOTYKBXXCYCXRZ-UHFFFAOYSA-N 4-(2-chlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1Cl AOTYKBXXCYCXRZ-UHFFFAOYSA-N 0.000 description 2
• WQKDEUGMDSTMAK-UHFFFAOYSA-N 4-[2-(trifluoromethyl)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1C(F)(F)F WQKDEUGMDSTMAK-UHFFFAOYSA-N 0.000 description 2
• BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 2
• HFXAFXVXPMUQCQ-UHFFFAOYSA-N 4-oxoproline Chemical compound OC(=O)C1CC(=O)CN1 HFXAFXVXPMUQCQ-UHFFFAOYSA-N 0.000 description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
• 101150065749 Churc1 gene Proteins 0.000 description 2
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
• 229910004373 HOAc Inorganic materials 0.000 description 2
• SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
• 241001465754 Metazoa Species 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
• HBVZRPAKZOLBPL-UHFFFAOYSA-N O-Acetylethanolamine Chemical compound CC(=O)OCCN HBVZRPAKZOLBPL-UHFFFAOYSA-N 0.000 description 2
• 229910019142 PO4 Inorganic materials 0.000 description 2
• 208000002193 Pain Diseases 0.000 description 2
• 239000005662 Paraffin oil Substances 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• 239000004698 Polyethylene Substances 0.000 description 2
• 102100038239 Protein Churchill Human genes 0.000 description 2
• 229920002472 Starch Polymers 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
• 239000012317 TBTU Substances 0.000 description 2
• BHZIXWRWYBBDHE-UHFFFAOYSA-N [4-(3-methylpyridin-2-yl)phenyl]methanol Chemical compound CC1=CC=CN=C1C1=CC=C(CO)C=C1 BHZIXWRWYBBDHE-UHFFFAOYSA-N 0.000 description 2
• CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 2
• 230000009471 action Effects 0.000 description 2
• 239000013543 active substance Substances 0.000 description 2
• 150000001263 acyl chlorides Chemical class 0.000 description 2
• 239000000783 alginic acid Substances 0.000 description 2
• 235000010443 alginic acid Nutrition 0.000 description 2
• 229920000615 alginic acid Polymers 0.000 description 2
• 229960001126 alginic acid Drugs 0.000 description 2
• 150000004781 alginic acids Chemical class 0.000 description 2
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 235000010323 ascorbic acid Nutrition 0.000 description 2
• 239000011668 ascorbic acid Substances 0.000 description 2
• 238000011914 asymmetric synthesis Methods 0.000 description 2
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
• DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 2
• 230000001275 ca(2+)-mobilization Effects 0.000 description 2
• 239000004202 carbamide Substances 0.000 description 2
• 210000001715 carotid artery Anatomy 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• 239000003086 colorant Substances 0.000 description 2
• 239000000470 constituent Substances 0.000 description 2
• 230000009989 contractile response Effects 0.000 description 2
• 125000004122 cyclic group Chemical group 0.000 description 2
• 238000010511 deprotection reaction Methods 0.000 description 2
• 238000011161 development Methods 0.000 description 2
• RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 description 2
• 229960000452 diethylstilbestrol Drugs 0.000 description 2
• 230000003828 downregulation Effects 0.000 description 2
• 239000003480 eluent Substances 0.000 description 2
• 238000010828 elution Methods 0.000 description 2
• 210000004696 endometrium Anatomy 0.000 description 2
• 238000001704 evaporation Methods 0.000 description 2
• 230000008020 evaporation Effects 0.000 description 2
• 239000000706 filtrate Substances 0.000 description 2
• 239000006260 foam Substances 0.000 description 2
• 238000010230 functional analysis Methods 0.000 description 2
• BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
• 239000007789 gas Substances 0.000 description 2
• 229960001867 guaiacol Drugs 0.000 description 2
• IWCAQTQMDRGMPI-UHFFFAOYSA-N hexane-3,4-diamine Chemical compound CCC(N)C(N)CC IWCAQTQMDRGMPI-UHFFFAOYSA-N 0.000 description 2
• 125000005946 imidazo[1,2-a]pyridyl group Chemical group 0.000 description 2
• 238000001727 in vivo Methods 0.000 description 2
• 230000002401 inhibitory effect Effects 0.000 description 2
• CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 2
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
• 125000005956 isoquinolyl group Chemical group 0.000 description 2
• 239000008141 laxative Substances 0.000 description 2
• 229940125722 laxative agent Drugs 0.000 description 2
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
• 239000000463 material Substances 0.000 description 2
• 239000012528 membrane Substances 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
• 239000008108 microcrystalline cellulose Substances 0.000 description 2
• 229940016286 microcrystalline cellulose Drugs 0.000 description 2
• 125000001624 naphthyl group Chemical group 0.000 description 2
• 239000012299 nitrogen atmosphere Substances 0.000 description 2
• MVSMBIBGGPSEHQ-UHFFFAOYSA-N o-[(4-methoxyphenyl)methyl]hydroxylamine Chemical compound COC1=CC=C(CON)C=C1 MVSMBIBGGPSEHQ-UHFFFAOYSA-N 0.000 description 2
• 239000012074 organic phase Substances 0.000 description 2
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
• VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
• LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
• COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Chemical compound OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
• 239000010452 phosphate Substances 0.000 description 2
• 229920000573 polyethylene Polymers 0.000 description 2
• 229910000027 potassium carbonate Inorganic materials 0.000 description 2
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
• LCDCPQHFCOBUEF-UHFFFAOYSA-N pyrrolidine-1-carboxamide Chemical compound NC(=O)N1CCCC1 LCDCPQHFCOBUEF-UHFFFAOYSA-N 0.000 description 2
• 238000010992 reflux Methods 0.000 description 2
• CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 2
• 235000017557 sodium bicarbonate Nutrition 0.000 description 2
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
• 229910000029 sodium carbonate Inorganic materials 0.000 description 2
• 239000008107 starch Substances 0.000 description 2
• 235000019698 starch Nutrition 0.000 description 2
• 238000007920 subcutaneous administration Methods 0.000 description 2
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
• 239000005720 sucrose Substances 0.000 description 2
• 239000003826 tablet Substances 0.000 description 2
• IYRULVWLVRRRIS-UHFFFAOYSA-N tert-butyl 3-amino-2-hydroxypropanoate Chemical compound CC(C)(C)OC(=O)C(O)CN IYRULVWLVRRRIS-UHFFFAOYSA-N 0.000 description 2
• 125000003831 tetrazolyl group Chemical group 0.000 description 2
• 229940125712 tocolytic agent Drugs 0.000 description 2
• 239000003675 tocolytic agent Substances 0.000 description 2
• 238000012546 transfer Methods 0.000 description 2
• ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 2
• 239000003981 vehicle Substances 0.000 description 2
• XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 1
• VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
• PGJHAXAIVJIVSM-GFCCVEGCSA-N (1S)-2-amino-1-naphthalen-2-ylethanol Chemical compound C1=CC=CC2=CC([C@H](O)CN)=CC=C21 PGJHAXAIVJIVSM-GFCCVEGCSA-N 0.000 description 1
• SOCAXRLFGRNEPK-IFZYUDKTSA-N (1r,3s,5r)-2-n-[1-carbamoyl-5-(cyanomethoxy)indol-3-yl]-3-n-[(3-chloro-2-fluorophenyl)methyl]-2-azabicyclo[3.1.0]hexane-2,3-dicarboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)NC1=CN(C2=CC=C(OCC#N)C=C21)C(=O)N)NCC1=CC=CC(Cl)=C1F SOCAXRLFGRNEPK-IFZYUDKTSA-N 0.000 description 1
• SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 description 1
• VLXDQDJEENQBCU-UHFFFAOYSA-N (2-amino-1-phenylethyl) acetate Chemical compound CC(=O)OC(CN)C1=CC=CC=C1 VLXDQDJEENQBCU-UHFFFAOYSA-N 0.000 description 1
• NSJVYHOPHZMZPN-UHFFFAOYSA-N (2-methylphenyl)boronic acid Chemical compound CC1=CC=CC=C1B(O)O NSJVYHOPHZMZPN-UHFFFAOYSA-N 0.000 description 1
• ABBLBAYYMZDQGA-BXRBKJIMSA-N (2S)-3-amino-2-hydroxypropanoic acid Chemical compound NC[C@H](O)C(O)=O.NC[C@H](O)C(O)=O ABBLBAYYMZDQGA-BXRBKJIMSA-N 0.000 description 1
• DOMQFIFVDIAOOT-ROUUACIJSA-N (2S,3R)-N-[4-(2,6-dimethoxyphenyl)-5-(5-methylpyridin-3-yl)-1,2,4-triazol-3-yl]-3-(5-methylpyrimidin-2-yl)butane-2-sulfonamide Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NN=C1C=1C=NC=C(C=1)C)NS(=O)(=O)[C@@H](C)[C@H](C)C1=NC=C(C=N1)C DOMQFIFVDIAOOT-ROUUACIJSA-N 0.000 description 1
• AOFUBOWZWQFQJU-SNOJBQEQSA-N (2r,3s,4s,5r)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol;(2s,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O.OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O AOFUBOWZWQFQJU-SNOJBQEQSA-N 0.000 description 1
• JZEHWMUIAKALDN-QMMMGPOBSA-N (2s)-1-amino-3-phenoxypropan-2-ol Chemical compound NC[C@H](O)COC1=CC=CC=C1 JZEHWMUIAKALDN-QMMMGPOBSA-N 0.000 description 1
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
• SZILGJCJFXNDMP-AWEZNQCLSA-N (2s)-2-(3-hydroxyazetidine-1-carbonyl)-n-(3-methylphenyl)-4-oxopyrrolidine-1-carboxamide Chemical compound CC1=CC=CC(NC(=O)N2[C@@H](CC(=O)C2)C(=O)N2CC(O)C2)=C1 SZILGJCJFXNDMP-AWEZNQCLSA-N 0.000 description 1
• RPEKVXSOLUPBLF-QMMMGPOBSA-N (2s)-4-methoxyimino-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CON=C1C[C@@H](C(O)=O)N(C(=O)OC(C)(C)C)C1 RPEKVXSOLUPBLF-QMMMGPOBSA-N 0.000 description 1
• HLYIUIAODDCEFB-RRPNLBNLSA-N (2s)-n-[(3r)-3-hydroxy-3-phenylpropyl]-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)NCC[C@@H](O)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1C HLYIUIAODDCEFB-RRPNLBNLSA-N 0.000 description 1
• RPEKVXSOLUPBLF-OTIXFSKASA-N (2s,4e)-4-methoxyimino-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CO\N=C1/C[C@@H](C(O)=O)N(C(=O)OC(C)(C)C)C1 RPEKVXSOLUPBLF-OTIXFSKASA-N 0.000 description 1
• MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
• HGRWHBQLRXWSLV-DEOSSOPVSA-N (4s)-3'-(3,6-dihydro-2h-pyran-5-yl)-1'-fluoro-7'-(3-fluoropyridin-2-yl)spiro[5h-1,3-oxazole-4,5'-chromeno[2,3-c]pyridine]-2-amine Chemical compound C1OC(N)=N[C@]21C1=CC(C=3COCCC=3)=NC(F)=C1OC1=CC=C(C=3C(=CC=CN=3)F)C=C12 HGRWHBQLRXWSLV-DEOSSOPVSA-N 0.000 description 1
• HNGJTIMDNFIMFO-NSHDSACASA-N (5S)-5-(1H-benzimidazol-2-yl)-N-methoxypyrrolidin-3-imine Chemical compound C1C(=NOC)CN[C@@H]1C1=NC2=CC=CC=C2N1 HNGJTIMDNFIMFO-NSHDSACASA-N 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• SFLSHLFXELFNJZ-MRVPVSSYSA-N (S)-noradrenaline Chemical compound NC[C@@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-MRVPVSSYSA-N 0.000 description 1
• UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
• ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
• MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
• DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 1
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
• APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
• MJUVRTYWUMPBTR-MRXNPFEDSA-N 1-(2,2-difluoro-1,3-benzodioxol-5-yl)-n-[1-[(2r)-2,3-dihydroxypropyl]-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)indol-5-yl]cyclopropane-1-carboxamide Chemical compound FC=1C=C2N(C[C@@H](O)CO)C(C(C)(CO)C)=CC2=CC=1NC(=O)C1(C=2C=C3OC(F)(F)OC3=CC=2)CC1 MJUVRTYWUMPBTR-MRXNPFEDSA-N 0.000 description 1
• AGECZFKPNRSRDG-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-1-yl)piperidine Chemical class C1CC2=CC=CC=C2C1N1CCCCC1 AGECZFKPNRSRDG-UHFFFAOYSA-N 0.000 description 1
• QKFZLXYMTBTBTR-UHFFFAOYSA-N 1-(2-hydroxyethyl)-4-methoxyiminopyrrolidine-2-carboxamide Chemical compound OCCN1C(CC(C1)=NOC)C(=O)N QKFZLXYMTBTBTR-UHFFFAOYSA-N 0.000 description 1
• QOPFPPLWAWSYQN-UHFFFAOYSA-N 1-(2-methoxyacetyl)pyrrolidine-2-carboxamide Chemical compound COCC(=O)N1CCCC1C(N)=O QOPFPPLWAWSYQN-UHFFFAOYSA-N 0.000 description 1
• KKIMDKMETPPURN-UHFFFAOYSA-N 1-(3-(trifluoromethyl)phenyl)piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCNCC2)=C1 KKIMDKMETPPURN-UHFFFAOYSA-N 0.000 description 1
• IBQMAPSJLHRQPE-UHFFFAOYSA-N 1-(4-(trifluoromethyl)phenyl)piperazine Chemical compound C1=CC(C(F)(F)F)=CC=C1N1CCNCC1 IBQMAPSJLHRQPE-UHFFFAOYSA-N 0.000 description 1
• MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 1
• SAHRUXJRNZXDIB-UHFFFAOYSA-N 1-(thiophen-2-ylmethyl)pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1CC1=CC=CS1 SAHRUXJRNZXDIB-UHFFFAOYSA-N 0.000 description 1
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
• TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
• UBXZYAGCGXKZDX-WKAHHKJFSA-N 1-[(1R,2R)-2-(hydroxymethyl)cyclohexyl]-4-methoxyiminopyrrolidine-2-carboxamide Chemical compound OC[C@H]1[C@@H](CCCC1)N1C(CC(C1)=NOC)C(=O)N UBXZYAGCGXKZDX-WKAHHKJFSA-N 0.000 description 1
• JGUZGDFTVMINHU-ZGTCLIOFSA-N 1-[(2S)-2-hydroxy-2-phenylethyl]-4-methoxyiminopyrrolidine-2-carboxamide Chemical compound O[C@H](CN1C(CC(C1)=NOC)C(=O)N)C1=CC=CC=C1 JGUZGDFTVMINHU-ZGTCLIOFSA-N 0.000 description 1
• ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
• QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 1
• IGERQMDMYFFQLC-UHFFFAOYSA-N 1-methylpyrrolidine-2-carboxamide Chemical compound CN1CCCC1C(N)=O IGERQMDMYFFQLC-UHFFFAOYSA-N 0.000 description 1
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
• KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
• PYHXGXCGESYPCW-UHFFFAOYSA-M 2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)[O-])C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-M 0.000 description 1
• PCAXITAPTVOLGL-UHFFFAOYSA-N 2,3-diaminophenol Chemical compound NC1=CC=CC(O)=C1N PCAXITAPTVOLGL-UHFFFAOYSA-N 0.000 description 1
• KNHJIEOCVVIBIV-UHFFFAOYSA-N 2,3-dimethylphenyl isocyanate Chemical compound CC1=CC=CC(N=C=O)=C1C KNHJIEOCVVIBIV-UHFFFAOYSA-N 0.000 description 1
• HMIOLEOLMUNFJN-UHFFFAOYSA-N 2-(2-methoxyethyl)-1-N-(3-methylphenyl)pyrrolidine-1,2-dicarboxamide Chemical compound COCCC1(C(N)=O)CCCN1C(=O)NC1=CC=CC(C)=C1 HMIOLEOLMUNFJN-UHFFFAOYSA-N 0.000 description 1
• YDDSASJZESWCJC-UHFFFAOYSA-N 2-(3-methoxyphenyl)pyrrolidine-1,2-dicarboxamide Chemical compound COC1=CC=CC(C2(N(CCC2)C(N)=O)C(N)=O)=C1 YDDSASJZESWCJC-UHFFFAOYSA-N 0.000 description 1
• VGXKOUVHTCYTNS-UHFFFAOYSA-N 2-(9-ethylcarbazol-3-yl)pyrrolidine-1,2-dicarboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1C1(C(N)=O)CCCN1C(N)=O VGXKOUVHTCYTNS-UHFFFAOYSA-N 0.000 description 1
• GVOYKJPMUUJXBS-UHFFFAOYSA-N 2-(aminomethyl)aniline Chemical compound NCC1=CC=CC=C1N GVOYKJPMUUJXBS-UHFFFAOYSA-N 0.000 description 1
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
• PPBMVZJOBAGISL-DEOSSOPVSA-N 2-[4-[(2S)-2-[4-(2-hydroxyethyl)piperazine-1-carbonyl]-4-methoxyiminopyrrolidine-1-carbonyl]phenyl]benzonitrile Chemical compound N1([C@@H](CC(C1)=NOC)C(=O)N1CCN(CCO)CC1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1C#N PPBMVZJOBAGISL-DEOSSOPVSA-N 0.000 description 1
• QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
• QXTRPGAMVIONMK-UHFFFAOYSA-N 2-amino-5-ethyl-1,3,4-thiadiazole Chemical compound CCC1=NN=C(N)S1 QXTRPGAMVIONMK-UHFFFAOYSA-N 0.000 description 1
• BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 1
• PZSISEFPCYMBDL-UHFFFAOYSA-N 2-bromo-3-methylpyridine Chemical compound CC1=CC=CN=C1Br PZSISEFPCYMBDL-UHFFFAOYSA-N 0.000 description 1
• IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
• STNAQENUCOFEKN-UHFFFAOYSA-N 2-cyanobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C#N STNAQENUCOFEKN-UHFFFAOYSA-N 0.000 description 1
• KWMBADTWRIGGGG-UHFFFAOYSA-N 2-diethoxyphosphorylacetonitrile Chemical compound CCOP(=O)(CC#N)OCC KWMBADTWRIGGGG-UHFFFAOYSA-N 0.000 description 1
• NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical group C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
• 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 1
• WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 description 1
• XCQPCFULNWOZSD-UHFFFAOYSA-N 2-methoxyiminopyrrolidine-1-carboxylic acid Chemical compound CON=C1CCCN1C(=O)O XCQPCFULNWOZSD-UHFFFAOYSA-N 0.000 description 1
• CAHIDRFUQUEUTR-UHFFFAOYSA-N 2-methyl-4-phenylbenzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC(C=2C=CC=CC=2)=C1 CAHIDRFUQUEUTR-UHFFFAOYSA-N 0.000 description 1
• LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
• YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
• RPKCLSMBVQLWIN-UHFFFAOYSA-N 2-n-methylbenzene-1,2-diamine Chemical compound CNC1=CC=CC=C1N RPKCLSMBVQLWIN-UHFFFAOYSA-N 0.000 description 1
• NYCDSJNKGZMFSX-UHFFFAOYSA-N 2-oxo-6-pentylpyran-3-carboxylic acid Chemical compound CCCCCC1=CC=C(C(O)=O)C(=O)O1 NYCDSJNKGZMFSX-UHFFFAOYSA-N 0.000 description 1
• WGUCLERYUKVGBU-UHFFFAOYSA-N 2-pentylpyrrolidine-1,2-dicarboxamide Chemical compound CCCCCC1(C(N)=O)CCCN1C(N)=O WGUCLERYUKVGBU-UHFFFAOYSA-N 0.000 description 1
• PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
• HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
• BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
• PRRULTKCQWIHRK-UHFFFAOYSA-N 3-(chloromethylidene)pyrrolidine-2-carboxylic acid Chemical compound ClC=C1C(NCC1)C(=O)O PRRULTKCQWIHRK-UHFFFAOYSA-N 0.000 description 1
• YGYGASJNJTYNOL-CQSZACIVSA-N 3-[(4r)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C1CS(=O)(=O)C(C)(C)C[C@@H]1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(F)=CC=3)C=C12 YGYGASJNJTYNOL-CQSZACIVSA-N 0.000 description 1
• WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
• SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 1
• GCUGPBDAPGIXDF-UHFFFAOYSA-N 3-methoxyimino-1-[4-(2-methoxyphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound NC(=O)C1C(=NOC)CCN1C(=O)C1=CC=C(C=2C(=CC=CC=2)OC)C=C1 GCUGPBDAPGIXDF-UHFFFAOYSA-N 0.000 description 1
• ZGBAXFOVTPCBRW-UHFFFAOYSA-N 3-methyl-4-(2-methylphenyl)benzoic acid Chemical compound CC1=CC=CC=C1C1=CC=C(C(O)=O)C=C1C ZGBAXFOVTPCBRW-UHFFFAOYSA-N 0.000 description 1
• ITLWSYAJGXPQSO-UHFFFAOYSA-N 3-methyl-4-phenylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C1=CC=CC=C1 ITLWSYAJGXPQSO-UHFFFAOYSA-N 0.000 description 1
• NXTDJHZGHOFSQG-UHFFFAOYSA-N 3-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 NXTDJHZGHOFSQG-UHFFFAOYSA-N 0.000 description 1
• XNLWJFYYOIRPIO-UHFFFAOYSA-N 3-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1 XNLWJFYYOIRPIO-UHFFFAOYSA-N 0.000 description 1
• OTZSTWZWLJLAAB-UHFFFAOYSA-N 4-(1-oxidopyridin-1-ium-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=[N+]1[O-] OTZSTWZWLJLAAB-UHFFFAOYSA-N 0.000 description 1
• STLGUJTWUAPIIL-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC(Cl)=C1Cl STLGUJTWUAPIIL-UHFFFAOYSA-N 0.000 description 1
• DGHGRAZWNAQANC-UHFFFAOYSA-N 4-(2,4-difluorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(F)C=C1F DGHGRAZWNAQANC-UHFFFAOYSA-N 0.000 description 1
• NVYOOVLWXDVFAA-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(Cl)C(Cl)=C1 NVYOOVLWXDVFAA-UHFFFAOYSA-N 0.000 description 1
• SJIVTXJWSYIMDG-UHFFFAOYSA-N 4-(3-chlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC(Cl)=C1 SJIVTXJWSYIMDG-UHFFFAOYSA-N 0.000 description 1
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
• OAMJQKDGQYAQKD-UHFFFAOYSA-N 4-(3-methoxyphenyl)benzoic acid Chemical compound COC1=CC=CC(C=2C=CC(=CC=2)C(O)=O)=C1 OAMJQKDGQYAQKD-UHFFFAOYSA-N 0.000 description 1
• BNNVIEYGJYMYHU-UHFFFAOYSA-N 4-(3-methylpyridin-2-yl)benzoic acid Chemical compound CC1=CC=CN=C1C1=CC=C(C(O)=O)C=C1 BNNVIEYGJYMYHU-UHFFFAOYSA-N 0.000 description 1
• FDPKGXQCDURRBM-UHFFFAOYSA-N 4-(4-methoxyphenyl)benzoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(O)=O)C=C1 FDPKGXQCDURRBM-UHFFFAOYSA-N 0.000 description 1
• RZOCCLOTCXINRG-UHFFFAOYSA-N 4-(4-methylphenyl)benzoic acid Chemical compound C1=CC(C)=CC=C1C1=CC=C(C(O)=O)C=C1 RZOCCLOTCXINRG-UHFFFAOYSA-N 0.000 description 1
• DVNBYCHKMPBWCJ-ZDUSSCGKSA-N 4-(dimethylamino)-1-[(2s)-2-(3-hydroxyazetidine-1-carbonyl)-4-methylidenepyrrolidin-1-yl]butan-1-one Chemical compound CN(C)CCCC(=O)N1CC(=C)C[C@H]1C(=O)N1CC(O)C1 DVNBYCHKMPBWCJ-ZDUSSCGKSA-N 0.000 description 1
• VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 description 1
• LFMPHDUPXVEMAB-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC(C(F)(F)F)=C1 LFMPHDUPXVEMAB-UHFFFAOYSA-N 0.000 description 1
• YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
• XYWIPYBIIRTJMM-IBGZPJMESA-N 4-[[(2S)-2-[4-[5-chloro-2-[4-(trifluoromethyl)triazol-1-yl]phenyl]-5-methoxy-2-oxopyridin-1-yl]butanoyl]amino]-2-fluorobenzamide Chemical compound CC[C@H](N1C=C(OC)C(=CC1=O)C1=C(C=CC(Cl)=C1)N1C=C(N=N1)C(F)(F)F)C(=O)NC1=CC(F)=C(C=C1)C(N)=O XYWIPYBIIRTJMM-IBGZPJMESA-N 0.000 description 1
• KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
• IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-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
• TUXYZHVUPGXXQG-UHFFFAOYSA-N 4-bromobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-N 0.000 description 1
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
• FPWNLURCHDRMHC-UHFFFAOYSA-N 4-chlorobiphenyl Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1 FPWNLURCHDRMHC-UHFFFAOYSA-N 0.000 description 1
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
• CNIWGSMGPQXANC-UHFFFAOYSA-N 4-methoxyimino-1-(4-phenylbenzoyl)pyrrolidine-2-carboxamide Chemical compound C1C(=NOC)CC(C(N)=O)N1C(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 CNIWGSMGPQXANC-UHFFFAOYSA-N 0.000 description 1
• RPEKVXSOLUPBLF-UHFFFAOYSA-N 4-methoxyimino-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CON=C1CC(C(O)=O)N(C(=O)OC(C)(C)C)C1 RPEKVXSOLUPBLF-UHFFFAOYSA-N 0.000 description 1
• HFEVBHWSDZPBBU-UHFFFAOYSA-N 4-methoxyimino-1-[4-(2-methoxyphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound C1C(=NOC)CC(C(N)=O)N1C(=O)C1=CC=C(C=2C(=CC=CC=2)OC)C=C1 HFEVBHWSDZPBBU-UHFFFAOYSA-N 0.000 description 1
• LQCDCVRVQFYZHH-UHFFFAOYSA-N 4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]pyrrolidine-2-carboxamide Chemical compound CON=C1CC(N(C1)C(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C)C(=O)N LQCDCVRVQFYZHH-UHFFFAOYSA-N 0.000 description 1
• CCBKADQVSXLSDN-UHFFFAOYSA-N 4-pyrimidin-5-ylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CN=CN=C1 CCBKADQVSXLSDN-UHFFFAOYSA-N 0.000 description 1
• IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
• KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
• MAUFTTLGOUBZNA-UHFFFAOYSA-N 6-n-Pentyl-alpha-pyrone Chemical compound CCCCCC1=CC=CC(=O)O1 MAUFTTLGOUBZNA-UHFFFAOYSA-N 0.000 description 1
• UNQYAAAWKOOBFQ-UHFFFAOYSA-N 7-[(4-chlorophenyl)methyl]-8-[4-chloro-3-(trifluoromethoxy)phenoxy]-1-(3-hydroxypropyl)-3-methylpurine-2,6-dione Chemical compound C=1C=C(Cl)C=CC=1CN1C=2C(=O)N(CCCO)C(=O)N(C)C=2N=C1OC1=CC=C(Cl)C(OC(F)(F)F)=C1 UNQYAAAWKOOBFQ-UHFFFAOYSA-N 0.000 description 1
• QZUNGZQACLCXSW-UHFFFAOYSA-N 7-amino-2-tert-butyl-4-(1H-pyrrol-2-yl)pyrido[2,3-d]pyrimidine-6-carboxamide Chemical compound CC(C)(C)c1nc(-c2ccc[nH]2)c2cc(C(N)=O)c(N)nc2n1 QZUNGZQACLCXSW-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
• PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 description 1
• ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 description 1
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• XMALGCMIIBIHMJ-UHFFFAOYSA-N C(C)N1C2=CC=CC=C2C=2C=C(C=CC12)C1(N(CC(C1)=NOC)C(=O)N)C(=O)N Chemical compound C(C)N1C2=CC=CC=C2C=2C=C(C=CC12)C1(N(CC(C1)=NOC)C(=O)N)C(=O)N XMALGCMIIBIHMJ-UHFFFAOYSA-N 0.000 description 1
• GWYFXQSWBXVODW-UHFFFAOYSA-N C(C)N1C2=CC=CC=C2C=2C=C(C=CC12)C1(N(CC(C1)=NOC)C(=O)NCCCCC)C(=O)N Chemical compound C(C)N1C2=CC=CC=C2C=2C=C(C=CC12)C1(N(CC(C1)=NOC)C(=O)NCCCCC)C(=O)N GWYFXQSWBXVODW-UHFFFAOYSA-N 0.000 description 1
• DCKOQVTWLKEBBB-UHFFFAOYSA-N C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1N1CCCC1C(N)=O Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1N1CCCC1C(N)=O DCKOQVTWLKEBBB-UHFFFAOYSA-N 0.000 description 1
• OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
• QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical class C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
• 238000007698 E/Z-isomerization reaction Methods 0.000 description 1
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
• 239000001263 FEMA 3042 Substances 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
• 108090000045 G-Protein-Coupled Receptors Proteins 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
• AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
• 208000010496 Heart Arrest Diseases 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
• 208000013016 Hypoglycemia Diseases 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• 244000246386 Mentha pulegium Species 0.000 description 1
• 235000016257 Mentha pulegium Nutrition 0.000 description 1
• 235000004357 Mentha x piperita Nutrition 0.000 description 1
• 102000005741 Metalloproteases Human genes 0.000 description 1
• 108010006035 Metalloproteases Proteins 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
• AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
• FEYNFHSRETUBEM-UHFFFAOYSA-N N-[3-(1,1-difluoroethyl)phenyl]-1-(4-methoxyphenyl)-3-methyl-5-oxo-4H-pyrazole-4-carboxamide Chemical compound COc1ccc(cc1)N1N=C(C)C(C(=O)Nc2cccc(c2)C(C)(F)F)C1=O FEYNFHSRETUBEM-UHFFFAOYSA-N 0.000 description 1
• OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 239000006057 Non-nutritive feed additive Substances 0.000 description 1
• WKYDBMVFIAHDEK-UHFFFAOYSA-N O=C1CC(N(C1)C(=O)N)C(=O)N Chemical compound O=C1CC(N(C1)C(=O)N)C(=O)N WKYDBMVFIAHDEK-UHFFFAOYSA-N 0.000 description 1
• IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
• 102100028139 Oxytocin receptor Human genes 0.000 description 1
• 229930040373 Paraformaldehyde Natural products 0.000 description 1
• 229920002230 Pectic acid Polymers 0.000 description 1
• LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 1
• BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
• 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
• 108010020346 Polyglutamic Acid Proteins 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
• 101000986756 Rattus norvegicus Oxytocin receptor Proteins 0.000 description 1
• 206010062237 Renal impairment Diseases 0.000 description 1
• 208000004756 Respiratory Insufficiency Diseases 0.000 description 1
• 206010038678 Respiratory depression Diseases 0.000 description 1
• 206010038687 Respiratory distress Diseases 0.000 description 1
• 229910004298 SiO 2 Inorganic materials 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• 208000001871 Tachycardia Diseases 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
• KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• 241000209140 Triticum Species 0.000 description 1
• 235000021307 Triticum Nutrition 0.000 description 1
• 206010046797 Uterine ischaemia Diseases 0.000 description 1
• 102000004136 Vasopressin Receptors Human genes 0.000 description 1
• 108090000643 Vasopressin Receptors Proteins 0.000 description 1
• LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
• GCWPGEWXYDEQAY-NKWVEPMBSA-N [(1r,2r)-2-aminocyclohexyl]methanol Chemical compound N[C@@H]1CCCC[C@H]1CO GCWPGEWXYDEQAY-NKWVEPMBSA-N 0.000 description 1
• QBXSMAPFDIXJKJ-NDEPHWFRSA-N [(2S)-4-methoxyimino-1-[4-(2-methylphenyl)benzoyl]pyrrolidin-2-yl]-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]methanone Chemical compound CON=C1CN([C@@H](C1)C(=O)N1CCN(CC1)C1=CC=C(C=C1)C(F)(F)F)C(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C QBXSMAPFDIXJKJ-NDEPHWFRSA-N 0.000 description 1
• RZRSXJVNVKHMEC-HZONWBDVSA-N [(2s,4z)-2-(1h-benzimidazol-2-yl)-4-methoxyiminopyrrolidin-1-yl]-(4-phenylphenyl)methanone Chemical compound N1([C@@H](C/C(C1)=N/OC)C=1NC2=CC=CC=C2N=1)C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 RZRSXJVNVKHMEC-HZONWBDVSA-N 0.000 description 1
• PZRPBPMLSSNFOM-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]boronic acid Chemical compound OCC1=CC=C(B(O)O)C=C1 PZRPBPMLSSNFOM-UHFFFAOYSA-N 0.000 description 1
• 150000001241 acetals Chemical class 0.000 description 1
• 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 1
• 239000003929 acidic solution Substances 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 239000004480 active ingredient Substances 0.000 description 1
• 239000000654 additive Substances 0.000 description 1
• 230000000996 additive effect Effects 0.000 description 1
• NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
• 150000003931 anilides Chemical class 0.000 description 1
• 150000001448 anilines Chemical class 0.000 description 1
• 238000010171 animal model Methods 0.000 description 1
• 238000013459 approach Methods 0.000 description 1
• 239000012736 aqueous medium Substances 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 150000004982 aromatic amines Chemical class 0.000 description 1
• 125000003710 aryl alkyl group Chemical group 0.000 description 1
• 150000001499 aryl bromides Chemical class 0.000 description 1
• 229940072107 ascorbate Drugs 0.000 description 1
• 229960005070 ascorbic acid Drugs 0.000 description 1
• 239000000305 astragalus gummifer gum Substances 0.000 description 1
• VWXRQYYUEIYXCZ-OBIMUBPZSA-N atosiban Chemical compound C1=CC(OCC)=CC=C1C[C@@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CCCN)C(=O)NCC(N)=O)CSSCCC(=O)N1 VWXRQYYUEIYXCZ-OBIMUBPZSA-N 0.000 description 1
• 229960002403 atosiban Drugs 0.000 description 1
• 108700007535 atosiban Proteins 0.000 description 1
• 239000011324 bead Substances 0.000 description 1
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
• 229940077388 benzenesulfonate Drugs 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
• USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 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
• 125000002619 bicyclic group Chemical group 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• 230000005540 biological transmission Effects 0.000 description 1
• 125000006267 biphenyl group Chemical group 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 238000010241 blood sampling Methods 0.000 description 1
• 235000010338 boric acid Nutrition 0.000 description 1
• 125000005619 boric acid group Chemical class 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 244000309464 bull Species 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
• FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
• 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
• 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
• 125000004555 carbazol-3-yl group Chemical group C1=CC(=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
• 125000002837 carbocyclic group Chemical group 0.000 description 1
• 150000001718 carbodiimides Chemical class 0.000 description 1
• 150000003857 carboxamides Chemical class 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• 150000007942 carboxylates Chemical class 0.000 description 1
• 230000011128 cardiac conduction Effects 0.000 description 1
• 230000015556 catabolic process Effects 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 235000013339 cereals Nutrition 0.000 description 1
• 150000001793 charged compounds Chemical class 0.000 description 1
• 229920001429 chelating resin Polymers 0.000 description 1
• DGLFSNZWRYADFC-UHFFFAOYSA-N chembl2334586 Chemical compound C1CCC2=CN=C(N)N=C2C2=C1NC1=CC=C(C#CC(C)(O)C)C=C12 DGLFSNZWRYADFC-UHFFFAOYSA-N 0.000 description 1
• 125000003636 chemical group Chemical group 0.000 description 1
• 239000007810 chemical reaction solvent Substances 0.000 description 1
• 210000004978 chinese hamster ovary cell Anatomy 0.000 description 1
• YMNRWRKDEPEIAQ-UHFFFAOYSA-M chloromethyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCl)C1=CC=CC=C1 YMNRWRKDEPEIAQ-UHFFFAOYSA-M 0.000 description 1
• 229940117975 chromium trioxide Drugs 0.000 description 1
• WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
• GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
• 229940114081 cinnamate Drugs 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 229940001468 citrate Drugs 0.000 description 1
• 239000008119 colloidal silica Substances 0.000 description 1
• 239000013065 commercial product Substances 0.000 description 1
• 230000008602 contraction Effects 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 239000012043 crude product Substances 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 210000003785 decidua Anatomy 0.000 description 1
• 230000007423 decrease Effects 0.000 description 1
• 238000006731 degradation reaction Methods 0.000 description 1
• WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
• 229910001873 dinitrogen Inorganic materials 0.000 description 1
• NWVNXDKZIQLBNM-UHFFFAOYSA-N diphenylmethylpiperazine Chemical compound C1CNCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 NWVNXDKZIQLBNM-UHFFFAOYSA-N 0.000 description 1
• LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 230000002222 downregulating effect Effects 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1
• 238000012377 drug delivery Methods 0.000 description 1
• 210000001198 duodenum Anatomy 0.000 description 1
• 230000002526 effect on cardiovascular system Effects 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 230000002708 enhancing effect Effects 0.000 description 1
• 125000004185 ester group Chemical group 0.000 description 1
• 230000032050 esterification Effects 0.000 description 1
• 238000005886 esterification reaction Methods 0.000 description 1
• 229940011871 estrogen Drugs 0.000 description 1
• 239000000262 estrogen Substances 0.000 description 1
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
• VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 1
• DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 230000001747 exhibiting effect Effects 0.000 description 1
• 230000001605 fetal effect Effects 0.000 description 1
• 238000011049 filling Methods 0.000 description 1
• 239000012467 final product Substances 0.000 description 1
• 235000019634 flavors Nutrition 0.000 description 1
• 239000012530 fluid Substances 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• 229940050411 fumarate Drugs 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 235000011087 fumaric acid Nutrition 0.000 description 1
• LRBQNJMCXXYXIU-QWKBTXIPSA-N gallotannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@H]2[C@@H]([C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-QWKBTXIPSA-N 0.000 description 1
• 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 229940093915 gynecological organic acid Drugs 0.000 description 1
• 238000011141 high resolution liquid chromatography Methods 0.000 description 1
• 238000000265 homogenisation Methods 0.000 description 1
• 229940088597 hormone Drugs 0.000 description 1
• 239000005556 hormone Substances 0.000 description 1
• 235000001050 hortel pimenta Nutrition 0.000 description 1
• 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
• 150000002429 hydrazines Chemical class 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
• BNSOYWDFFBDEFB-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O BNSOYWDFFBDEFB-UHFFFAOYSA-L 0.000 description 1
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
• 150000002443 hydroxylamines Chemical class 0.000 description 1
• 201000001421 hyperglycemia Diseases 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 239000003112 inhibitor Substances 0.000 description 1
• 239000007972 injectable composition Substances 0.000 description 1
• 230000037038 intracellular mobilization Effects 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000005342 ion exchange Methods 0.000 description 1
• 150000002500 ions Chemical class 0.000 description 1
• VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 210000004731 jugular vein Anatomy 0.000 description 1
• 238000002372 labelling Methods 0.000 description 1
• 238000011005 laboratory method Methods 0.000 description 1
• 208000037805 labour Diseases 0.000 description 1
• 150000003951 lactams Chemical class 0.000 description 1
• 150000002596 lactones Chemical class 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
• 239000003446 ligand Substances 0.000 description 1
• 239000007791 liquid phase Substances 0.000 description 1
• 239000006193 liquid solution Substances 0.000 description 1
• 239000006194 liquid suspension Substances 0.000 description 1
• 229940049920 malate Drugs 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 239000003550 marker Substances 0.000 description 1
• 238000001819 mass spectrum Methods 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 210000004914 menses Anatomy 0.000 description 1
• 230000002503 metabolic effect Effects 0.000 description 1
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
• BLWYXBNNBYXPPL-YFKPBYRVSA-N methyl (2s)-pyrrolidine-2-carboxylate Chemical class COC(=O)[C@@H]1CCCN1 BLWYXBNNBYXPPL-YFKPBYRVSA-N 0.000 description 1
• 125000006178 methyl benzyl group Chemical group 0.000 description 1
• 150000004702 methyl esters Chemical class 0.000 description 1
• STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
• 229940012189 methyl orange Drugs 0.000 description 1
• 229960001047 methyl salicylate Drugs 0.000 description 1
• LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
• 210000000754 myometrium Anatomy 0.000 description 1
• FEKRFYZGYUTGRY-UHFFFAOYSA-N n'-ethylmethanediimine Chemical compound CCN=C=N FEKRFYZGYUTGRY-UHFFFAOYSA-N 0.000 description 1
• FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 1
• VFBILHPIHUPBPZ-UHFFFAOYSA-N n-[[2-[4-(difluoromethoxy)-3-propan-2-yloxyphenyl]-1,3-oxazol-4-yl]methyl]-2-ethoxybenzamide Chemical compound CCOC1=CC=CC=C1C(=O)NCC1=COC(C=2C=C(OC(C)C)C(OC(F)F)=CC=2)=N1 VFBILHPIHUPBPZ-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• DOWVMJFBDGWVML-UHFFFAOYSA-N n-cyclohexyl-n-methyl-4-(1-oxidopyridin-1-ium-3-yl)imidazole-1-carboxamide Chemical compound C1=NC(C=2C=[N+]([O-])C=CC=2)=CN1C(=O)N(C)C1CCCCC1 DOWVMJFBDGWVML-UHFFFAOYSA-N 0.000 description 1
• NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• AEMBWNDIEFEPTH-UHFFFAOYSA-N n-tert-butyl-n-ethylnitrous amide Chemical compound CCN(N=O)C(C)(C)C AEMBWNDIEFEPTH-UHFFFAOYSA-N 0.000 description 1
• YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
• 230000002232 neuromuscular Effects 0.000 description 1
• 238000006386 neutralization reaction Methods 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 231100000957 no side effect Toxicity 0.000 description 1
• 230000009871 nonspecific binding Effects 0.000 description 1
• NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 description 1
• VYCHJEXJHFTAQI-UHFFFAOYSA-N o-prop-2-enylhydroxylamine;hydrate;hydrochloride Chemical compound O.Cl.NOCC=C VYCHJEXJHFTAQI-UHFFFAOYSA-N 0.000 description 1
• 238000005457 optimization Methods 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 230000016087 ovulation Effects 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 230000003647 oxidation Effects 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• 230000020477 pH reduction Effects 0.000 description 1
• 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 1
• WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
• 229920002866 paraformaldehyde Polymers 0.000 description 1
• 230000032696 parturition Effects 0.000 description 1
• 230000037361 pathway Effects 0.000 description 1
• UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
• 239000000813 peptide hormone Substances 0.000 description 1
• 108091005465 peptide hormone receptors Proteins 0.000 description 1
• 102000014187 peptide receptors Human genes 0.000 description 1
• 230000009984 peri-natal effect Effects 0.000 description 1
• 239000003208 petroleum Substances 0.000 description 1
• 229940124531 pharmaceutical excipient Drugs 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
• 239000002953 phosphate buffered saline Substances 0.000 description 1
• 229910052698 phosphorus Inorganic materials 0.000 description 1
• 239000011574 phosphorus Substances 0.000 description 1
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• 229960005235 piperonyl butoxide Drugs 0.000 description 1
• 230000036470 plasma concentration Effects 0.000 description 1
• 229920001983 poloxamer Polymers 0.000 description 1
• 239000010318 polygalacturonic acid Substances 0.000 description 1
• 229920002643 polyglutamic acid Polymers 0.000 description 1
• 231100000857 poor renal function Toxicity 0.000 description 1
• LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• 230000035935 pregnancy Effects 0.000 description 1
• 150000003141 primary amines Chemical class 0.000 description 1
• 238000000159 protein binding assay Methods 0.000 description 1
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
• NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 1
• 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
• 230000009467 reduction Effects 0.000 description 1
• 230000002829 reductive effect Effects 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 238000009877 rendering Methods 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• 238000006798 ring closing metathesis reaction Methods 0.000 description 1
• 238000007363 ring formation reaction Methods 0.000 description 1
• 230000000630 rising effect Effects 0.000 description 1
• IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical group N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
• 229960001634 ritodrine Drugs 0.000 description 1
• CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
• 229940081974 saccharin Drugs 0.000 description 1
• 235000019204 saccharin Nutrition 0.000 description 1
• 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
• 229960002052 salbutamol Drugs 0.000 description 1
• 238000003345 scintillation counting Methods 0.000 description 1
• 150000003335 secondary amines Chemical class 0.000 description 1
• 230000003248 secreting effect Effects 0.000 description 1
• 230000028327 secretion Effects 0.000 description 1
• XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
• 230000035945 sensitivity Effects 0.000 description 1
• 238000010898 silica gel chromatography Methods 0.000 description 1
• XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
• 150000003384 small molecules Chemical class 0.000 description 1
• WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
• 235000010234 sodium benzoate Nutrition 0.000 description 1
• 239000004299 sodium benzoate Substances 0.000 description 1
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
• 239000008247 solid mixture Substances 0.000 description 1
• 238000003746 solid phase reaction Methods 0.000 description 1
• 239000012265 solid product Substances 0.000 description 1
• 230000002269 spontaneous effect Effects 0.000 description 1
• 230000006641 stabilisation Effects 0.000 description 1
• 238000011105 stabilization Methods 0.000 description 1
• 230000000638 stimulation Effects 0.000 description 1
• 239000012089 stop solution Substances 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
• 239000006228 supernatant Substances 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 208000024891 symptom Diseases 0.000 description 1
• 230000006794 tachycardia Effects 0.000 description 1
• 235000015523 tannic acid Nutrition 0.000 description 1
• 229940033123 tannic acid Drugs 0.000 description 1
• 229920002258 tannic acid Polymers 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• 229960000195 terbutaline Drugs 0.000 description 1
• DRDVJQOGFWAVLH-UHFFFAOYSA-N tert-butyl n-hydroxycarbamate Chemical compound CC(C)(C)OC(=O)NO DRDVJQOGFWAVLH-UHFFFAOYSA-N 0.000 description 1
• 238000011287 therapeutic dose Methods 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 150000003555 thioacetals Chemical class 0.000 description 1
• 150000003585 thioureas Chemical class 0.000 description 1
• 230000003195 tocolytic effect Effects 0.000 description 1
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
• 125000003944 tolyl group Chemical group 0.000 description 1
• 210000003437 trachea Anatomy 0.000 description 1
• WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
• 125000004953 trihalomethyl group Chemical group 0.000 description 1
• JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical group OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
• 229960000281 trometamol Drugs 0.000 description 1
• 230000001228 trophic effect Effects 0.000 description 1
• 230000003827 upregulation Effects 0.000 description 1
• 150000003672 ureas Chemical class 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 239000001993 wax Substances 0.000 description 1
• 239000000230 xanthan gum Substances 0.000 description 1
• 229920001285 xanthan gum Polymers 0.000 description 1
• 235000010493 xanthan gum Nutrition 0.000 description 1
• 229940082509 xanthan gum Drugs 0.000 description 1