PT1635839E - Benzo[4,5]tieno[2,3-d]pirimidin-4-onas e sua utilização em terapia - Google Patents

Info

Publication number

PT1635839E

PT1635839E PT04803089T PT04803089T PT1635839E PT 1635839 E PT1635839 E PT 1635839E PT 04803089 T PT04803089 T PT 04803089T PT 04803089 T PT04803089 T PT 04803089T PT 1635839 E PT1635839 E PT 1635839E

Authority

PT

Portugal

Prior art keywords

alkyl

group

optionally substituted

compound

benzo

Prior art date

2003-06-10

Links

• Espacenet
• Global Dossier
• Discuss

• 238000002560 therapeutic procedure Methods 0.000 title claims description 13
• UELJJSQADCDBMU-UHFFFAOYSA-N 3h-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical class S1C2=CC=CC=C2C2=C1N=CNC2=O UELJJSQADCDBMU-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims description 457
• -1 hydroxylphenyl Chemical group 0.000 claims description 412
• 125000001424 substituent group Chemical group 0.000 claims description 159
• 229910052736 halogen Inorganic materials 0.000 claims description 145
• 125000003118 aryl group Chemical group 0.000 claims description 133
• 150000002367 halogens Chemical class 0.000 claims description 129
• 229910052739 hydrogen Inorganic materials 0.000 claims description 127
• 239000001257 hydrogen Substances 0.000 claims description 127
• 125000000217 alkyl group Chemical group 0.000 claims description 108
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 106
• 125000001072 heteroaryl group Chemical group 0.000 claims description 89
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 86
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 74
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 73
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 53
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 53
• 125000004122 cyclic group Chemical group 0.000 claims description 49
• 125000004043 oxo group Chemical group O=* 0.000 claims description 45
• 208000035475 disorder Diseases 0.000 claims description 42
• 238000011282 treatment Methods 0.000 claims description 40
• 230000001419 dependent effect Effects 0.000 claims description 39
• 125000001544 thienyl group Chemical group 0.000 claims description 37
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 35
• 150000002825 nitriles Chemical class 0.000 claims description 34
• 102000004190 Enzymes Human genes 0.000 claims description 33
• 108090000790 Enzymes Proteins 0.000 claims description 33
• 125000002541 furyl group Chemical group 0.000 claims description 33
• 125000004104 aryloxy group Chemical group 0.000 claims description 31
• 201000010099 disease Diseases 0.000 claims description 31
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
• 125000004414 alkyl thio group Chemical group 0.000 claims description 29
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
• 125000002252 acyl group Chemical group 0.000 claims description 27
• 125000004432 carbon atom Chemical group C* 0.000 claims description 27
• 125000003545 alkoxy group Chemical group 0.000 claims description 26
• 125000004076 pyridyl group Chemical group 0.000 claims description 26
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 24
• 201000010260 leiomyoma Diseases 0.000 claims description 24
• 125000001624 naphthyl group Chemical group 0.000 claims description 24
• 239000003270 steroid hormone Substances 0.000 claims description 24
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 23
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 23
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 23
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 22
• 210000001519 tissue Anatomy 0.000 claims description 21
• 206010046798 Uterine leiomyoma Diseases 0.000 claims description 20
• 125000003368 amide group Chemical group 0.000 claims description 20
• 125000002757 morpholinyl group Chemical group 0.000 claims description 20
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 20
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 19
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 18
• 125000003386 piperidinyl group Chemical group 0.000 claims description 18
• 201000009273 Endometriosis Diseases 0.000 claims description 17
• 125000005110 aryl thio group Chemical group 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
• 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 16
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 16
• 125000004423 acyloxy group Chemical group 0.000 claims description 16
• 229910052794 bromium Inorganic materials 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 16
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
• 150000002430 hydrocarbons Chemical group 0.000 claims description 15
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 15
• 230000005764 inhibitory process Effects 0.000 claims description 14
• 125000004193 piperazinyl group Chemical group 0.000 claims description 14
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 14
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 14
• 125000003725 azepanyl group Chemical group 0.000 claims description 13
• 125000002393 azetidinyl group Chemical group 0.000 claims description 13
• 125000005959 diazepanyl group Chemical group 0.000 claims description 13
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 13
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
• 125000005961 oxazepanyl group Chemical group 0.000 claims description 13
• 125000000160 oxazolidinyl group Chemical group 0.000 claims description 13
• 230000002265 prevention Effects 0.000 claims description 13
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 13
• 125000001984 thiazolidinyl group Chemical group 0.000 claims description 13
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 13
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 12
• 239000004305 biphenyl Substances 0.000 claims description 12
• 235000010290 biphenyl Nutrition 0.000 claims description 12
• 125000003107 substituted aryl group Chemical group 0.000 claims description 12
• 229940124530 sulfonamide Drugs 0.000 claims description 12
• 150000003456 sulfonamides Chemical class 0.000 claims description 12
• 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims description 12
• 125000000335 thiazolyl group Chemical group 0.000 claims description 12
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 11
• 206010060862 Prostate cancer Diseases 0.000 claims description 11
• 125000004442 acylamino group Chemical group 0.000 claims description 11
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 11
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 229920006395 saturated elastomer Polymers 0.000 claims description 10
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 9
• JEDVKUHCDPPWNR-UHFFFAOYSA-N 3h-thieno[2,3-d]pyrimidin-4-one Chemical compound O=C1NC=NC2=C1C=CS2 JEDVKUHCDPPWNR-UHFFFAOYSA-N 0.000 claims description 9
• 101710088194 Dehydrogenase Proteins 0.000 claims description 9
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000002883 imidazolyl group Chemical group 0.000 claims description 9
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 9
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 9
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 206010006187 Breast cancer Diseases 0.000 claims description 8
• 208000026310 Breast neoplasm Diseases 0.000 claims description 8
• 239000013543 active substance Substances 0.000 claims description 8
• 125000005251 aryl acyl group Chemical group 0.000 claims description 8
• 125000001041 indolyl group Chemical group 0.000 claims description 8
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
• 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 claims description 7
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 7
• 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 7
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
• 208000007106 menorrhagia Diseases 0.000 claims description 7
• 125000002971 oxazolyl group Chemical group 0.000 claims description 7
• 125000001680 trimethoxyphenyl group Chemical group 0.000 claims description 7
• 201000007954 uterine fibroid Diseases 0.000 claims description 7
• 208000002874 Acne Vulgaris Diseases 0.000 claims description 6
• 201000004384 Alopecia Diseases 0.000 claims description 6
• 208000005171 Dysmenorrhea Diseases 0.000 claims description 6
• 206010013935 Dysmenorrhoea Diseases 0.000 claims description 6
• 206010014733 Endometrial cancer Diseases 0.000 claims description 6
• 206010014759 Endometrial neoplasm Diseases 0.000 claims description 6
• 206010020112 Hirsutism Diseases 0.000 claims description 6
• 206010027514 Metrorrhagia Diseases 0.000 claims description 6
• 206010033128 Ovarian cancer Diseases 0.000 claims description 6
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 6
• 206010000496 acne Diseases 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 6
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 208000001132 Osteoporosis Diseases 0.000 claims description 5
• 206010039792 Seborrhoea Diseases 0.000 claims description 5
• 208000002495 Uterine Neoplasms Diseases 0.000 claims description 5
• 201000002996 androgenic alopecia Diseases 0.000 claims description 5
• 239000003433 contraceptive agent Substances 0.000 claims description 5
• 230000004064 dysfunction Effects 0.000 claims description 5
• 201000006828 endometrial hyperplasia Diseases 0.000 claims description 5
• JZGZKRJVTIRPOK-UHFFFAOYSA-N ethyl thiophene-2-carboxylate Chemical compound CCOC(=O)C1=CC=CS1 JZGZKRJVTIRPOK-UHFFFAOYSA-N 0.000 claims description 5
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
• 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 5
• 208000006155 precocious puberty Diseases 0.000 claims description 5
• 201000001514 prostate carcinoma Diseases 0.000 claims description 5
• 201000007094 prostatitis Diseases 0.000 claims description 5
• 230000021595 spermatogenesis Effects 0.000 claims description 5
• 230000002485 urinary effect Effects 0.000 claims description 5
• 206010046766 uterine cancer Diseases 0.000 claims description 5
• MPBUVXZOTUEAOE-UHFFFAOYSA-N 2,3-dibenzyl-7-tert-butyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound C1C(C(C)(C)C)CCC(C=2C(=O)N3CC=4C=CC=CC=4)=C1SC=2N=C3CC1=CC=CC=C1 MPBUVXZOTUEAOE-UHFFFAOYSA-N 0.000 claims description 4
• 208000024827 Alzheimer disease Diseases 0.000 claims description 4
• 208000002177 Cataract Diseases 0.000 claims description 4
• 206010009944 Colon cancer Diseases 0.000 claims description 4
• 208000008448 Congenital adrenal hyperplasia Diseases 0.000 claims description 4
• PWPCBTSIPLBQSH-UHFFFAOYSA-N O=C[S+](C=C1)C2=C1C=NC=N2 Chemical compound O=C[S+](C=C1)C2=C1C=NC=N2 PWPCBTSIPLBQSH-UHFFFAOYSA-N 0.000 claims description 4
• 206010052428 Wound Diseases 0.000 claims description 4
• 208000027418 Wounds and injury Diseases 0.000 claims description 4
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 4
• 230000000903 blocking effect Effects 0.000 claims description 4
• 208000029742 colonic neoplasm Diseases 0.000 claims description 4
• 150000002148 esters Chemical class 0.000 claims description 4
• 201000006417 multiple sclerosis Diseases 0.000 claims description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
• 208000008742 seborrheic dermatitis Diseases 0.000 claims description 4
• 230000037303 wrinkles Effects 0.000 claims description 4
• QCKAVYPIXVSRIP-UHFFFAOYSA-N 2-(2-chloro-3,4,5-trimethoxyphenyl)-8-hydroxy-3-(oxolan-2-ylmethyl)-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=CC=CC(O)=C4SC=3N=2)CC2OCCC2)=C1Cl QCKAVYPIXVSRIP-UHFFFAOYSA-N 0.000 claims description 3
• XQSDTRVRYXPNAZ-UHFFFAOYSA-N 3-butyl-2-(2,4-difluorophenyl)-8-hydroxy-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound N=1C=2SC3=C(O)C=CC=C3C=2C(=O)N(CCCC)C=1C1=CC=C(F)C=C1F XQSDTRVRYXPNAZ-UHFFFAOYSA-N 0.000 claims description 3
• HHBJKZCQWKMHNL-UHFFFAOYSA-N 3-butyl-8-hydroxy-2-(3,4,5-trimethoxyphenyl)-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound N=1C=2SC3=C(O)C=CC=C3C=2C(=O)N(CCCC)C=1C1=CC(OC)=C(OC)C(OC)=C1 HHBJKZCQWKMHNL-UHFFFAOYSA-N 0.000 claims description 3
• FVCXLTHFQRFWJY-UHFFFAOYSA-N 5-bromo-3-(2-methylpropyl)-2-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=C(C(CCC4Br)=O)SC=3N=2)CC(C)C)=C1 FVCXLTHFQRFWJY-UHFFFAOYSA-N 0.000 claims description 3
• IERNYVIIHPXXCC-UHFFFAOYSA-N 8-hydroxy-3-(2-methylbutyl)-2-(3,4,5-trimethoxyphenyl)-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound N=1C=2SC3=C(O)C=CC=C3C=2C(=O)N(CC(C)CC)C=1C1=CC(OC)=C(OC)C(OC)=C1 IERNYVIIHPXXCC-UHFFFAOYSA-N 0.000 claims description 3
• 125000003282 alkyl amino group Chemical group 0.000 claims description 3
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• 125000000950 dibromo group Chemical group Br* 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
• FBFTVBPTKNXUJZ-UHFFFAOYSA-N 7-bromo-3-(2-methylbutyl)-2-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound N=1C=2SC(C(C(Br)CC3)=O)=C3C=2C(=O)N(CC(C)CC)C=1C1=CC(OC)=C(OC)C(OC)=C1 FBFTVBPTKNXUJZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000001246 bromo group Chemical group Br* 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 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 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
• 125000003396 thiol group Chemical class [H]S* 0.000 claims 10
• 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
• 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
• BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 claims 1
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
• 206010036049 Polycystic ovaries Diseases 0.000 claims 1
• 125000004422 alkyl sulphonamide group Chemical group 0.000 claims 1
• 125000004802 cyanophenyl group Chemical group 0.000 claims 1
• 125000004188 dichlorophenyl group Chemical group 0.000 claims 1
• 125000004212 difluorophenyl group Chemical group 0.000 claims 1
• 125000001207 fluorophenyl group Chemical group 0.000 claims 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
• 206010020718 hyperplasia Diseases 0.000 claims 1
• 125000006513 pyridinyl methyl group Chemical group 0.000 claims 1
• 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 179
• 238000005481 NMR spectroscopy Methods 0.000 description 130
• 238000000034 method Methods 0.000 description 108
• 239000007858 starting material Substances 0.000 description 83
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 72
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
• 239000011734 sodium Substances 0.000 description 50
• XPNGNIFUDRPBFJ-UHFFFAOYSA-N (2-methylphenyl)methanol Chemical compound CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 47
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 34
• 239000000203 mixture Substances 0.000 description 30
• 238000006243 chemical reaction Methods 0.000 description 29
• 239000011541 reaction mixture Substances 0.000 description 28
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
• 239000006227 byproduct Substances 0.000 description 26
• DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 26
• 239000000243 solution Substances 0.000 description 26
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
• VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 23
• 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 21
• 239000000460 chlorine Substances 0.000 description 21
• OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 21
• 239000012043 crude product Substances 0.000 description 20
• 210000004027 cell Anatomy 0.000 description 19
• 230000000694 effects Effects 0.000 description 19
• 229960005309 estradiol Drugs 0.000 description 19
• 239000000047 product Substances 0.000 description 18
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
• 150000003431 steroids Chemical class 0.000 description 18
• MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 16
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 16
• 229910052801 chlorine Inorganic materials 0.000 description 16
• 239000003112 inhibitor Substances 0.000 description 16
• 239000007787 solid Substances 0.000 description 16
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 15
• 229930182833 estradiol Natural products 0.000 description 15
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 15
• 102100038595 Estrogen receptor Human genes 0.000 description 14
• 230000015572 biosynthetic process Effects 0.000 description 14
• GDNWCNZMRFWJPO-UHFFFAOYSA-N 1,3-benzodioxol-5-ylmethanamine;hydrochloride Chemical compound Cl.NCC1=CC=C2OCOC2=C1 GDNWCNZMRFWJPO-UHFFFAOYSA-N 0.000 description 13
• 150000001408 amides Chemical class 0.000 description 13
• 239000000262 estrogen Substances 0.000 description 13
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• ICXXXLGATNSZAV-UHFFFAOYSA-N butylazanium;chloride Chemical compound [Cl-].CCCC[NH3+] ICXXXLGATNSZAV-UHFFFAOYSA-N 0.000 description 12
• 229940011871 estrogen Drugs 0.000 description 12
• 108010038795 estrogen receptors Proteins 0.000 description 12
• 150000003573 thiols Chemical group 0.000 description 12
• 235000019439 ethyl acetate Nutrition 0.000 description 11
• 239000002904 solvent Substances 0.000 description 11
• 238000012360 testing method Methods 0.000 description 11
• UQJNPPXLUJHLCR-UHFFFAOYSA-N 2-phenoxyethylazanium;chloride Chemical compound Cl.NCCOC1=CC=CC=C1 UQJNPPXLUJHLCR-UHFFFAOYSA-N 0.000 description 10
• 239000003098 androgen Substances 0.000 description 10
• XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 10
• 238000004587 chromatography analysis Methods 0.000 description 10
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
• 238000002360 preparation method Methods 0.000 description 10
• LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 10
• MNNZINNZIQVULG-UHFFFAOYSA-N 2-chloroethylbenzene Chemical compound ClCCC1=CC=CC=C1 MNNZINNZIQVULG-UHFFFAOYSA-N 0.000 description 9
• ZZLKPFGLOQUCNC-UHFFFAOYSA-N 2-thiophen-2-ylethanamine;hydrochloride Chemical compound Cl.NCCC1=CC=CS1 ZZLKPFGLOQUCNC-UHFFFAOYSA-N 0.000 description 9
• 241000282414 Homo sapiens Species 0.000 description 9
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 9
• 230000027455 binding Effects 0.000 description 9
• 239000003480 eluent Substances 0.000 description 9
• 239000002244 precipitate Substances 0.000 description 9
• 230000002829 reductive effect Effects 0.000 description 9
• 238000003786 synthesis reaction Methods 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
• SELMBIXOWHGETQ-UHFFFAOYSA-N NCCCN(CCC1)C1=O.Cl Chemical compound NCCCN(CCC1)C1=O.Cl SELMBIXOWHGETQ-UHFFFAOYSA-N 0.000 description 8
• 239000002253 acid Substances 0.000 description 8
• 125000001309 chloro group Chemical group Cl* 0.000 description 8
• 230000002401 inhibitory effect Effects 0.000 description 8
• 239000012074 organic phase Substances 0.000 description 8
• 238000010992 reflux Methods 0.000 description 8
• 229960003604 testosterone Drugs 0.000 description 8
• RLGVDTCKJKBXOC-UHFFFAOYSA-N (3,4-dichlorophenyl)methanamine;hydrochloride Chemical compound Cl.NCC1=CC=C(Cl)C(Cl)=C1 RLGVDTCKJKBXOC-UHFFFAOYSA-N 0.000 description 7
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical class O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 7
• CGTWPKMZGWJCGE-UHFFFAOYSA-N 2-pyridin-2-ylethanamine;hydrochloride Chemical compound Cl.NCCC1=CC=CC=N1 CGTWPKMZGWJCGE-UHFFFAOYSA-N 0.000 description 7
• HVLUYXIJZLDNIS-UHFFFAOYSA-N 2-thiophen-2-ylethanamine Chemical compound NCCC1=CC=CS1 HVLUYXIJZLDNIS-UHFFFAOYSA-N 0.000 description 7
• DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 7
• 238000003818 flash chromatography Methods 0.000 description 7
• 238000009472 formulation Methods 0.000 description 7
• 239000003163 gonadal steroid hormone Substances 0.000 description 7
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
• 238000007254 oxidation reaction Methods 0.000 description 7
• 238000003756 stirring Methods 0.000 description 7
• DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 6
• FVPSNVVHINDDKH-UHFFFAOYSA-N 1-bromo-1,3,3,3-tetrafluoroprop-1-ene Chemical compound FC(Br)=CC(F)(F)F FVPSNVVHINDDKH-UHFFFAOYSA-N 0.000 description 6
• 108010084625 17-beta-hydroxysteroid dehydrogenase type 3 Proteins 0.000 description 6
• XPQIPUZPSLAZDV-UHFFFAOYSA-N 2-pyridylethylamine Chemical compound NCCC1=CC=CC=N1 XPQIPUZPSLAZDV-UHFFFAOYSA-N 0.000 description 6
• 108010070743 3(or 17)-beta-hydroxysteroid dehydrogenase Proteins 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 6
• 208000000236 Prostatic Neoplasms Diseases 0.000 description 6
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
• MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 6
• 230000037396 body weight Effects 0.000 description 6
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
• 239000012267 brine Substances 0.000 description 6
• 238000011161 development Methods 0.000 description 6
• 229960003399 estrone Drugs 0.000 description 6
• 230000003647 oxidation Effects 0.000 description 6
• YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 6
• ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 6
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
• 239000000725 suspension Substances 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
• BYHOTUFEUBWUME-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-5-ylmethanamine;hydrochloride Chemical compound Cl.NCC1=CC=C2OCCC2=C1 BYHOTUFEUBWUME-UHFFFAOYSA-N 0.000 description 5
• IMLAIXAZMVDRGA-UHFFFAOYSA-N 2-phenoxyethanamine Chemical compound NCCOC1=CC=CC=C1 IMLAIXAZMVDRGA-UHFFFAOYSA-N 0.000 description 5
• YFWNJDNDEMWGDW-UHFFFAOYSA-N 3,5-dihydro-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound N1=CNC(=O)C2=C1SC1=C2CC=CC1=O YFWNJDNDEMWGDW-UHFFFAOYSA-N 0.000 description 5
• OUGMRQJTULXVDC-UHFFFAOYSA-N 9h-fluoren-9-amine Chemical compound C1=CC=C2C(N)C3=CC=CC=C3C2=C1 OUGMRQJTULXVDC-UHFFFAOYSA-N 0.000 description 5
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
• 101100451536 Arabidopsis thaliana HSD2 gene Proteins 0.000 description 5
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
• 101100451537 Caenorhabditis elegans hsd-1 gene Proteins 0.000 description 5
• 102100034067 Dehydrogenase/reductase SDR family member 11 Human genes 0.000 description 5
• 101000652369 Homo sapiens Spermatogenesis-associated protein 7 Proteins 0.000 description 5
• 102100036501 Hydroxysteroid 11-beta-dehydrogenase 1-like protein Human genes 0.000 description 5
• 241000124008 Mammalia Species 0.000 description 5
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
• BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 description 5
• 239000000556 agonist Substances 0.000 description 5
• RSIHSRDYCUFFLA-DYKIIFRCSA-N boldenone Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 RSIHSRDYCUFFLA-DYKIIFRCSA-N 0.000 description 5
• 239000003153 chemical reaction reagent Substances 0.000 description 5
• RSIHSRDYCUFFLA-UHFFFAOYSA-N dehydrotestosterone Natural products O=C1C=CC2(C)C3CCC(C)(C(CC4)O)C4C3CCC2=C1 RSIHSRDYCUFFLA-UHFFFAOYSA-N 0.000 description 5
• 229940079593 drug Drugs 0.000 description 5
• 210000004696 endometrium Anatomy 0.000 description 5
• 230000002427 irreversible effect Effects 0.000 description 5
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• 229950006238 nadide Drugs 0.000 description 5
• 239000013642 negative control Substances 0.000 description 5
• 150000003141 primary amines Chemical class 0.000 description 5
• 230000002441 reversible effect Effects 0.000 description 5
• 239000000758 substrate Substances 0.000 description 5
• 229910052717 sulfur Inorganic materials 0.000 description 5
• 208000024891 symptom Diseases 0.000 description 5
• QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 5
• 210000004291 uterus Anatomy 0.000 description 5
• HJORCZCMNWLHMB-UHFFFAOYSA-N 1-(3-aminopropyl)pyrrolidin-2-one Chemical compound NCCCN1CCCC1=O HJORCZCMNWLHMB-UHFFFAOYSA-N 0.000 description 4
• JOIJPKUXOCCGSN-UHFFFAOYSA-N 1-benzylpiperidin-4-amine;hydrochloride Chemical compound Cl.C1CC(N)CCN1CC1=CC=CC=C1 JOIJPKUXOCCGSN-UHFFFAOYSA-N 0.000 description 4
• 108010082514 17-Hydroxysteroid Dehydrogenases Proteins 0.000 description 4
• 102000004026 17-Hydroxysteroid Dehydrogenases Human genes 0.000 description 4
• 102100022586 17-beta-hydroxysteroid dehydrogenase type 2 Human genes 0.000 description 4
• 102100022585 17-beta-hydroxysteroid dehydrogenase type 3 Human genes 0.000 description 4
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 4
• SYVNVEGIRVXRQH-UHFFFAOYSA-N 3-fluorobenzoyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=C1 SYVNVEGIRVXRQH-UHFFFAOYSA-N 0.000 description 4
• FXNSVEQMUYPYJS-UHFFFAOYSA-N 4-(2-aminoethyl)benzenesulfonamide Chemical compound NCCC1=CC=C(S(N)(=O)=O)C=C1 FXNSVEQMUYPYJS-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• 239000004342 Benzoyl peroxide Substances 0.000 description 4
• OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
• 101710174214 Estradiol 17-beta-dehydrogenase 2 Proteins 0.000 description 4
• 108010044467 Isoenzymes Proteins 0.000 description 4
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
• 208000002193 Pain Diseases 0.000 description 4
• 239000004480 active ingredient Substances 0.000 description 4
• 239000005557 antagonist Substances 0.000 description 4
• 238000003556 assay Methods 0.000 description 4
• 239000002585 base Substances 0.000 description 4
• 235000019400 benzoyl peroxide Nutrition 0.000 description 4
• 230000033228 biological regulation Effects 0.000 description 4
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
• 239000000839 emulsion Substances 0.000 description 4
• 239000002532 enzyme inhibitor Substances 0.000 description 4
• DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
• JHCRHXQSYPTWPT-UHFFFAOYSA-N ethyl 2-amino-7-hydroxy-1-benzothiophene-3-carboxylate Chemical compound C1=CC=C2C(C(=O)OCC)=C(N)SC2=C1O JHCRHXQSYPTWPT-UHFFFAOYSA-N 0.000 description 4
• 229910052731 fluorine Inorganic materials 0.000 description 4
• 239000007943 implant Substances 0.000 description 4
• 238000002347 injection Methods 0.000 description 4
• 239000007924 injection Substances 0.000 description 4
• AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
• BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 4
• KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
• 150000007522 mineralic acids Chemical class 0.000 description 4
• 239000012044 organic layer Substances 0.000 description 4
• 239000000546 pharmaceutical excipient Substances 0.000 description 4
• 230000003389 potentiating effect Effects 0.000 description 4
• 230000035755 proliferation Effects 0.000 description 4
• 239000000523 sample Substances 0.000 description 4
• JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 4
• DRJKOQOGSXDPKO-UHFFFAOYSA-N 2-(2-chloro-3,4,5-trimethoxyphenyl)-8-hydroxy-3-(2-methylbutyl)-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound N=1C=2SC3=C(O)C=CC=C3C=2C(=O)N(CC(C)CC)C=1C1=CC(OC)=C(OC)C(OC)=C1Cl DRJKOQOGSXDPKO-UHFFFAOYSA-N 0.000 description 3
• SVNCRRZKBNSMIV-UHFFFAOYSA-N 3-Aminoquinoline Chemical compound C1=CC=CC2=CC(N)=CN=C21 SVNCRRZKBNSMIV-UHFFFAOYSA-N 0.000 description 3
• KTOWKFGFWLSVAH-UHFFFAOYSA-N 3-benzyl-2-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C=4CCCCC=4SC=3N=2)CC=2C=CC=CC=2)=C1 KTOWKFGFWLSVAH-UHFFFAOYSA-N 0.000 description 3
• FEHWURPDQSWPJM-UHFFFAOYSA-N 3-benzyl-2-thiophen-2-yl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound C=1C=CSC=1C1=NC=2SC=3CCCCC=3C=2C(=O)N1CC1=CC=CC=C1 FEHWURPDQSWPJM-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
• DBMKBKPJYAHLQP-UHFFFAOYSA-N Azasetron hydrochloride Chemical compound Cl.C1N(CC2)CCC2C1NC(=O)C1=CC(Cl)=CC2=C1OCC(=O)N2C DBMKBKPJYAHLQP-UHFFFAOYSA-N 0.000 description 3
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
• HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 3
• WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical class F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
• 108060001084 Luciferase Proteins 0.000 description 3
• 239000005089 Luciferase Substances 0.000 description 3
• 206010028980 Neoplasm Diseases 0.000 description 3
• 229910019213 POCl3 Inorganic materials 0.000 description 3
• BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 3
• 229940124639 Selective inhibitor Drugs 0.000 description 3
• 229920002472 Starch Polymers 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• HXOYWCSTHVTLOW-YFKPBYRVSA-N [(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]methanamine Chemical compound CC1(C)OC[C@H](CN)O1 HXOYWCSTHVTLOW-YFKPBYRVSA-N 0.000 description 3
• 230000004913 activation Effects 0.000 description 3
• 238000004458 analytical method Methods 0.000 description 3
• 230000001833 anti-estrogenic effect Effects 0.000 description 3
• 238000005893 bromination reaction Methods 0.000 description 3
• 229910052799 carbon Inorganic materials 0.000 description 3
• 150000001728 carbonyl compounds Chemical class 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 229940124558 contraceptive agent Drugs 0.000 description 3
• 230000003247 decreasing effect Effects 0.000 description 3
• 230000004069 differentiation Effects 0.000 description 3
• 239000003085 diluting agent Substances 0.000 description 3
• 230000002357 endometrial effect Effects 0.000 description 3
• 239000003623 enhancer Substances 0.000 description 3
• 239000000328 estrogen antagonist Substances 0.000 description 3
• 230000001076 estrogenic effect Effects 0.000 description 3
• CDYVTVLXEWMCHU-UHFFFAOYSA-N ethyl 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate Chemical compound C1CCCC2=C1SC(N)=C2C(=O)OCC CDYVTVLXEWMCHU-UHFFFAOYSA-N 0.000 description 3
• 238000001704 evaporation Methods 0.000 description 3
• 230000008020 evaporation Effects 0.000 description 3
• 239000000706 filtrate Substances 0.000 description 3
• 239000011737 fluorine Substances 0.000 description 3
• 229940088597 hormone Drugs 0.000 description 3
• 239000005556 hormone Substances 0.000 description 3
• 238000000338 in vitro Methods 0.000 description 3
• 208000000509 infertility Diseases 0.000 description 3
• 230000036512 infertility Effects 0.000 description 3
• 231100000535 infertility Toxicity 0.000 description 3
• 239000004615 ingredient Substances 0.000 description 3
• 150000007529 inorganic bases Chemical class 0.000 description 3
• 150000002576 ketones Chemical class 0.000 description 3
• 230000003902 lesion Effects 0.000 description 3
• BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 3
• SJGFVFYSANQLLE-UHFFFAOYSA-N n-chlorocyclohexanamine Chemical compound ClNC1CCCCC1 SJGFVFYSANQLLE-UHFFFAOYSA-N 0.000 description 3
• 231100000252 nontoxic Toxicity 0.000 description 3
• 230000003000 nontoxic effect Effects 0.000 description 3
• 150000007524 organic acids Chemical class 0.000 description 3
• 210000000963 osteoblast Anatomy 0.000 description 3
• 230000001590 oxidative effect Effects 0.000 description 3
• 229910052760 oxygen Inorganic materials 0.000 description 3
• 238000007911 parenteral administration Methods 0.000 description 3
• 230000007170 pathology Effects 0.000 description 3
• 230000000144 pharmacologic effect Effects 0.000 description 3
• RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 3
• 239000013612 plasmid Substances 0.000 description 3
• 239000000186 progesterone Substances 0.000 description 3
• 229960003387 progesterone Drugs 0.000 description 3
• 238000011321 prophylaxis Methods 0.000 description 3
• HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 3
• LHJPZMGHTSQVLC-UHFFFAOYSA-N quinolin-3-amine;hydrochloride Chemical compound Cl.C1=CC=CC2=CC(N)=CN=C21 LHJPZMGHTSQVLC-UHFFFAOYSA-N 0.000 description 3
• 102000005962 receptors Human genes 0.000 description 3
• 108020003175 receptors Proteins 0.000 description 3
• 238000006722 reduction reaction Methods 0.000 description 3
• 239000008107 starch Substances 0.000 description 3
• 235000019698 starch Nutrition 0.000 description 3
• 239000011593 sulfur Substances 0.000 description 3
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
• 210000001550 testis Anatomy 0.000 description 3
• 229930192474 thiophene Natural products 0.000 description 3
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
• VSLJKXDXVIJAFZ-UHFFFAOYSA-N (2-chloro-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CCl)C1=CC=CC=C1 VSLJKXDXVIJAFZ-UHFFFAOYSA-N 0.000 description 2
• HGDABRKJGCGDAS-UHFFFAOYSA-N (3-benzyl-7-bromo-4-oxo-2-phenyl-[1]benzothiolo[2,3-d]pyrimidin-8-yl) acetate Chemical compound CC(=O)OC1=C(Br)C=CC(C=2C(=O)N3CC=4C=CC=CC=4)=C1SC=2N=C3C1=CC=CC=C1 HGDABRKJGCGDAS-UHFFFAOYSA-N 0.000 description 2
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 2
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 2
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
• DNGLRCHMGDDHNC-UHFFFAOYSA-N 1-benzothiophene-2-carbonyl chloride Chemical compound C1=CC=C2SC(C(=O)Cl)=CC2=C1 DNGLRCHMGDDHNC-UHFFFAOYSA-N 0.000 description 2
• WQXWNTPLZFVZNX-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-5-ylmethanamine Chemical compound NCC1=CC=C2OCCC2=C1 WQXWNTPLZFVZNX-UHFFFAOYSA-N 0.000 description 2
• XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 description 2
• RHAAGWRBIVCBSY-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine;hydron;chloride Chemical compound Cl.C1=CC=C2C(N)CCC2=C1 RHAAGWRBIVCBSY-UHFFFAOYSA-N 0.000 description 2
• HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
• AKVFJMJGKHPLQN-UHFFFAOYSA-N 2-(2-bromo-3,4,5-trimethoxyphenyl)-8-hydroxy-3-(2-methoxyethyl)-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound N=1C=2SC3=C(O)C=CC=C3C=2C(=O)N(CCOC)C=1C1=CC(OC)=C(OC)C(OC)=C1Br AKVFJMJGKHPLQN-UHFFFAOYSA-N 0.000 description 2
• XHHYIAWXOGUEII-UHFFFAOYSA-N 2-(2-bromo-3,4,5-trimethoxyphenyl)-8-hydroxy-3-(2-methylpropyl)-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=CC=CC(O)=C4SC=3N=2)CC(C)C)=C1Br XHHYIAWXOGUEII-UHFFFAOYSA-N 0.000 description 2
• CSMKOJLLUVNZOQ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-phenyl-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound C1=CC(OC)=CC=C1C(N(C1=O)C=2C=CC=CC=2)=NC2=C1C(CCCC1=O)=C1S2 CSMKOJLLUVNZOQ-UHFFFAOYSA-N 0.000 description 2
• KCTINEUOTAIIHL-UHFFFAOYSA-N 2-(methoxymethyl)-3-phenyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COCC1=NC=2SC=3CCCCC=3C=2C(=O)N1C1=CC=CC=C1 KCTINEUOTAIIHL-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• 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 2
• PIWJQKSYUVKDIO-UHFFFAOYSA-N 3-(2-methylbutyl)-2-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound N=1C=2SC(C(CCC3)=O)=C3C=2C(=O)N(CC(C)CC)C=1C1=CC(OC)=C(OC)C(OC)=C1 PIWJQKSYUVKDIO-UHFFFAOYSA-N 0.000 description 2
• ZOHCVQINDOJOHV-UHFFFAOYSA-N 3-(2-methylpropyl)-2-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C=4CCCCC=4SC=3N=2)CC(C)C)=C1 ZOHCVQINDOJOHV-UHFFFAOYSA-N 0.000 description 2
• RYPPOOQAGAETCB-UHFFFAOYSA-N 3-(2-methylpropyl)-2-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=C(C(CCC4)=O)SC=3N=2)CC(C)C)=C1 RYPPOOQAGAETCB-UHFFFAOYSA-N 0.000 description 2
• HUNNJRPAZOOJPB-UHFFFAOYSA-N 3-(furan-2-ylmethyl)-2-propyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound CCCC1=NC=2SC=3CCCCC=3C=2C(=O)N1CC1=CC=CO1 HUNNJRPAZOOJPB-UHFFFAOYSA-N 0.000 description 2
• BBWSCERDVFKRLN-UHFFFAOYSA-N 3-(furan-2-ylmethyl)-2-propyl-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound CCCC1=NC=2SC(C(CCC3)=O)=C3C=2C(=O)N1CC1=CC=CO1 BBWSCERDVFKRLN-UHFFFAOYSA-N 0.000 description 2
• UVXLSJHHBLRTOH-UHFFFAOYSA-N 3-[(2-methoxyphenyl)methyl]-2-propyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound CCCC1=NC=2SC=3CCCCC=3C=2C(=O)N1CC1=CC=CC=C1OC UVXLSJHHBLRTOH-UHFFFAOYSA-N 0.000 description 2
• BNEIWTXSZZDKFT-UHFFFAOYSA-N 3-[(2-methoxyphenyl)methyl]-2-propyl-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound CCCC1=NC=2SC(C(CCC3)=O)=C3C=2C(=O)N1CC1=CC=CC=C1OC BNEIWTXSZZDKFT-UHFFFAOYSA-N 0.000 description 2
• LLKLVELDILEPPT-UHFFFAOYSA-N 3-[(5-bromo-2-hydroxyphenyl)methyl]-8-hydroxy-2-propyl-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound CCCC1=NC=2SC3=C(O)C=CC=C3C=2C(=O)N1CC1=CC(Br)=CC=C1O LLKLVELDILEPPT-UHFFFAOYSA-N 0.000 description 2
• CNHKQRNSMFJJRK-UHFFFAOYSA-N 3-[(5-bromofuran-2-yl)methyl]-8-hydroxy-2-(3,4,5-trimethoxyphenyl)-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=CC=CC(O)=C4SC=3N=2)CC=2OC(Br)=CC=2)=C1 CNHKQRNSMFJJRK-UHFFFAOYSA-N 0.000 description 2
• DCLCVMZXAZXDIA-UHFFFAOYSA-N 3-[(5-bromofuran-2-yl)methyl]-8-hydroxy-2-propyl-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound CCCC1=NC=2SC3=C(O)C=CC=C3C=2C(=O)N1CC1=CC=C(Br)O1 DCLCVMZXAZXDIA-UHFFFAOYSA-N 0.000 description 2
• BYLUGBTVNKWOOP-UHFFFAOYSA-N 3-benzyl-2-(2-chloro-3,4,5-trimethoxyphenyl)-8-hydroxy-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=CC=CC(O)=C4SC=3N=2)CC=2C=CC=CC=2)=C1Cl BYLUGBTVNKWOOP-UHFFFAOYSA-N 0.000 description 2
• IHFCTBYGNJBHLU-UHFFFAOYSA-N 3-benzyl-2-(4-methoxyphenyl)-4-oxo-[1]benzothiolo[2,3-d]pyrimidine-7-carbaldehyde Chemical compound C1=CC(OC)=CC=C1C(N(C1=O)CC=2C=CC=CC=2)=NC2=C1C1=CC=C(C=O)C=C1S2 IHFCTBYGNJBHLU-UHFFFAOYSA-N 0.000 description 2
• QXKMHASBNVOUTQ-UHFFFAOYSA-N 3-benzyl-2-(4-methoxyphenyl)-7-methyl-8-phenoxy-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(N(C1=O)CC=2C=CC=CC=2)=NC2=C1C1=CC=C(C)C(OC=3C=CC=CC=3)=C1S2 QXKMHASBNVOUTQ-UHFFFAOYSA-N 0.000 description 2
• CHPCEQCCJAFWRL-UHFFFAOYSA-N 3-benzyl-2-(5-bromothiophen-2-yl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound S1C(Br)=CC=C1C(N(C1=O)CC=2C=CC=CC=2)=NC2=C1C(CCCC1=O)=C1S2 CHPCEQCCJAFWRL-UHFFFAOYSA-N 0.000 description 2
• CAAORZBJACKSKT-UHFFFAOYSA-N 3-benzyl-2-(hydroxymethyl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound OCC1=NC=2SC=3CCCCC=3C=2C(=O)N1CC1=CC=CC=C1 CAAORZBJACKSKT-UHFFFAOYSA-N 0.000 description 2
• APXKSUFUMITXIG-UHFFFAOYSA-N 3-benzyl-4,8-dioxo-6,7-dihydro-5H-[1]benzothiolo[2,3-d]pyrimidine-2-carboxylic acid Chemical compound C(C1=CC=CC=C1)N1C(=NC2=C(C1=O)C1=C(S2)C(CCC1)=O)C(=O)O APXKSUFUMITXIG-UHFFFAOYSA-N 0.000 description 2
• ZZDHJDWBTRGLLZ-UHFFFAOYSA-N 3-benzyl-4-oxo-8-phenylsulfanyl-2-(3,4,5-trimethoxyphenyl)-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-7-carbaldehyde Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=C(C(=C(C=O)CC4)SC=4C=CC=CC=4)SC=3N=2)CC=2C=CC=CC=2)=C1 ZZDHJDWBTRGLLZ-UHFFFAOYSA-N 0.000 description 2
• HVQNOVRWOGCYNH-UHFFFAOYSA-N 3-benzyl-4-oxo-8-phenylsulfanyl-2-(3,4,5-trimethoxyphenyl)-[1]benzothiolo[2,3-d]pyrimidine-7-carbaldehyde Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=CC=C(C=O)C(SC=5C=CC=CC=5)=C4SC=3N=2)CC=2C=CC=CC=2)=C1 HVQNOVRWOGCYNH-UHFFFAOYSA-N 0.000 description 2
• SZGBZHQMALWQKM-UHFFFAOYSA-N 3-benzyl-7,7-dibromo-2-(3-methoxyphenyl)-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COC1=CC=CC(C=2N(C(=O)C=3C4=C(C(C(Br)(Br)CC4)=O)SC=3N=2)CC=2C=CC=CC=2)=C1 SZGBZHQMALWQKM-UHFFFAOYSA-N 0.000 description 2
• QUCDFIZPJHVLKD-UHFFFAOYSA-N 3-benzyl-7,7-dibromo-2-phenyl-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound O=C1C(Br)(Br)CCC(C=2C(=O)N3CC=4C=CC=CC=4)=C1SC=2N=C3C1=CC=CC=C1 QUCDFIZPJHVLKD-UHFFFAOYSA-N 0.000 description 2
• BVCUGLVMPPRHHO-UHFFFAOYSA-N 3-benzyl-7-(hydroxymethyl)-2-(4-methoxyphenyl)-8-phenoxy-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(N(C1=O)CC=2C=CC=CC=2)=NC2=C1C1=CC=C(CO)C(OC=3C=CC=CC=3)=C1S2 BVCUGLVMPPRHHO-UHFFFAOYSA-N 0.000 description 2
• BRVXERSTTHPKCH-UHFFFAOYSA-N 3-benzyl-7-bromo-2-(2-bromo-3,4,5-trimethoxyphenyl)-8-hydroxy-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=CC=C(Br)C(O)=C4SC=3N=2)CC=2C=CC=CC=2)=C1Br BRVXERSTTHPKCH-UHFFFAOYSA-N 0.000 description 2
• KRIYXJNTLSPIED-UHFFFAOYSA-N 3-benzyl-7-bromo-2-phenyl-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound O=C1C(Br)CCC(C=2C(=O)N3CC=4C=CC=CC=4)=C1SC=2N=C3C1=CC=CC=C1 KRIYXJNTLSPIED-UHFFFAOYSA-N 0.000 description 2
• PKYJISHHPQTSPB-UHFFFAOYSA-N 3-benzyl-7-bromo-8-hydroxy-2-phenyl-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound OC1=C(Br)C=CC(C=2C(=O)N3CC=4C=CC=CC=4)=C1SC=2N=C3C1=CC=CC=C1 PKYJISHHPQTSPB-UHFFFAOYSA-N 0.000 description 2
• KYVABHFXVYWILI-UHFFFAOYSA-N 3-benzyl-7-chloro-2-(2-chloro-3,4,5-trimethoxyphenyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=C(C(C(Cl)CC4)=O)SC=3N=2)CC=2C=CC=CC=2)=C1Cl KYVABHFXVYWILI-UHFFFAOYSA-N 0.000 description 2
• OLPXQOVMCKUESX-UHFFFAOYSA-N 3-benzyl-8-chloro-4-oxo-2-(3,4,5-trimethoxyphenyl)-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-7-carbaldehyde Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=C(C(=C(C=O)CC4)Cl)SC=3N=2)CC=2C=CC=CC=2)=C1 OLPXQOVMCKUESX-UHFFFAOYSA-N 0.000 description 2
• PLMIWUYUHDKIOU-UHFFFAOYSA-N 3-benzyl-8-ethylsulfanyl-2-(4-methoxyphenyl)-4-oxo-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-7-carbaldehyde Chemical compound CCSC1=C(C=O)CCC(C=2C(=O)N3CC=4C=CC=CC=4)=C1SC=2N=C3C1=CC=C(OC)C=C1 PLMIWUYUHDKIOU-UHFFFAOYSA-N 0.000 description 2
• GOBGXFNVRDORKE-UHFFFAOYSA-N 3-benzyl-8-ethylsulfanyl-2-(4-methoxyphenyl)-4-oxo-[1]benzothiolo[2,3-d]pyrimidine-7-carbaldehyde Chemical compound CCSC1=C(C=O)C=CC(C=2C(=O)N3CC=4C=CC=CC=4)=C1SC=2N=C3C1=CC=C(OC)C=C1 GOBGXFNVRDORKE-UHFFFAOYSA-N 0.000 description 2
• HYWGXJAKHPWCPQ-UHFFFAOYSA-N 3-phenyl-2-(3,4,5-trihydroxyphenyl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound OC1=C(O)C(O)=CC(C=2N(C(=O)C=3C=4CCCCC=4SC=3N=2)C=2C=CC=CC=2)=C1 HYWGXJAKHPWCPQ-UHFFFAOYSA-N 0.000 description 2
• JCMSWJPYBQGUKQ-UHFFFAOYSA-N 3-phenyl-2-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C=4CCCCC=4SC=3N=2)C=2C=CC=CC=2)=C1 JCMSWJPYBQGUKQ-UHFFFAOYSA-N 0.000 description 2
• LCQXGFTXKWEWQC-UHFFFAOYSA-N 4-(dipropylsulfamoyl)benzoyl chloride Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(Cl)=O)C=C1 LCQXGFTXKWEWQC-UHFFFAOYSA-N 0.000 description 2
• 208000035116 46 XY Disorder of Sex Development Diseases 0.000 description 2
• JEJQJCKVMQVOHZ-UHFFFAOYSA-N 5,6-dihydro-4h-1-benzothiophen-7-one Chemical class O=C1CCCC2=C1SC=C2 JEJQJCKVMQVOHZ-UHFFFAOYSA-N 0.000 description 2
• KRTYWLYKAMQVQI-UHFFFAOYSA-N 7,7-dibromo-2-(2-bromo-3,4,5-trimethoxyphenyl)-3-(2-methoxyethyl)-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound N=1C=2SC(C(C(Br)(Br)CC3)=O)=C3C=2C(=O)N(CCOC)C=1C1=CC(OC)=C(OC)C(OC)=C1Br KRTYWLYKAMQVQI-UHFFFAOYSA-N 0.000 description 2
• LZDSKOPVTYZAAQ-UHFFFAOYSA-N 7,7-dibromo-2-(2-bromo-3,4,5-trimethoxyphenyl)-3-(2-methylbutyl)-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound N=1C=2SC(C(C(Br)(Br)CC3)=O)=C3C=2C(=O)N(CC(C)CC)C=1C1=CC(OC)=C(OC)C(OC)=C1Br LZDSKOPVTYZAAQ-UHFFFAOYSA-N 0.000 description 2
• HMBDXXFEWIONJC-UHFFFAOYSA-N 7,7-dibromo-3-butyl-2-(3,4,5-trimethoxyphenyl)-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound N=1C=2SC(C(C(Br)(Br)CC3)=O)=C3C=2C(=O)N(CCCC)C=1C1=CC(OC)=C(OC)C(OC)=C1 HMBDXXFEWIONJC-UHFFFAOYSA-N 0.000 description 2
• CWHQXXIBCKCPOD-UHFFFAOYSA-N 7,7-dichloro-2-(2-chloro-3,4,5-trimethoxyphenyl)-3-(2-methylbutyl)-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound N=1C=2SC(C(C(Cl)(Cl)CC3)=O)=C3C=2C(=O)N(CC(C)CC)C=1C1=CC(OC)=C(OC)C(OC)=C1Cl CWHQXXIBCKCPOD-UHFFFAOYSA-N 0.000 description 2
• ISHJWCPSUHYNRC-UHFFFAOYSA-N 7-bromo-2-(2-bromo-3,4,5-trimethoxyphenyl)-3-(2-methylpropyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=C(C(C(Br)CC4)=O)SC=3N=2)CC(C)C)=C1Br ISHJWCPSUHYNRC-UHFFFAOYSA-N 0.000 description 2
• PBCQMTMPIXTMJU-UHFFFAOYSA-N 7-bromo-2-(2-bromo-3,4,5-trimethoxyphenyl)-3-(oxolan-2-ylmethyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=C(C(C(Br)CC4)=O)SC=3N=2)CC2OCCC2)=C1Br PBCQMTMPIXTMJU-UHFFFAOYSA-N 0.000 description 2
• IUYRPQBPCFCYSL-UHFFFAOYSA-N 7-bromo-2-methyl-3-phenyl-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound CC1=NC=2SC(C(C(Br)CC3)=O)=C3C=2C(=O)N1C1=CC=CC=C1 IUYRPQBPCFCYSL-UHFFFAOYSA-N 0.000 description 2
• BZMABIGONIPDNG-UHFFFAOYSA-N 7-bromo-3-(2-methoxyethyl)-2-thiophen-2-yl-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound N=1C=2SC(C(C(Br)CC3)=O)=C3C=2C(=O)N(CCOC)C=1C1=CC=CS1 BZMABIGONIPDNG-UHFFFAOYSA-N 0.000 description 2
• KPSIDHHGSRSFOT-UHFFFAOYSA-N 7-bromo-3-(2-methylpropyl)-2-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=C(C(C(Br)CC4)=O)SC=3N=2)CC(C)C)=C1 KPSIDHHGSRSFOT-UHFFFAOYSA-N 0.000 description 2
• URGADRBPWPPKMY-UHFFFAOYSA-N 7-bromo-3-butyl-2-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound N=1C=2SC(C(C(Br)CC3)=O)=C3C=2C(=O)N(CCCC)C=1C1=CC(OC)=C(OC)C(OC)=C1 URGADRBPWPPKMY-UHFFFAOYSA-N 0.000 description 2
• WEQGSROXWBHSCH-UHFFFAOYSA-N 7-bromo-8-hydroxy-3-(2-hydroxyethyl)-2-thiophen-2-yl-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound N=1C=2SC3=C(O)C(Br)=CC=C3C=2C(=O)N(CCO)C=1C1=CC=CS1 WEQGSROXWBHSCH-UHFFFAOYSA-N 0.000 description 2
• RSKOJBUMOCXXJN-UHFFFAOYSA-N 7-bromo-8-hydroxy-3-(2-methoxyethyl)-2-thiophen-2-yl-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound N=1C=2SC3=C(O)C(Br)=CC=C3C=2C(=O)N(CCOC)C=1C1=CC=CS1 RSKOJBUMOCXXJN-UHFFFAOYSA-N 0.000 description 2
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
• 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 description 2
• 102100024089 Aldo-keto reductase family 1 member C2 Human genes 0.000 description 2
• RVRJIJCKXFCXJT-UHFFFAOYSA-N CCCCN.ClCCC1=CC=CC=C1 Chemical compound CCCCN.ClCCC1=CC=CC=C1 RVRJIJCKXFCXJT-UHFFFAOYSA-N 0.000 description 2
• 239000004215 Carbon black (E152) Substances 0.000 description 2
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• 229920000742 Cotton Polymers 0.000 description 2
• WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 2
• 108010007005 Estrogen Receptor alpha Proteins 0.000 description 2
• 108010041356 Estrogen Receptor beta Proteins 0.000 description 2
• 102100029951 Estrogen receptor beta Human genes 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• NMJREATYWWNIKX-UHFFFAOYSA-N GnRH Chemical compound C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CC(C)C)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 NMJREATYWWNIKX-UHFFFAOYSA-N 0.000 description 2
• 229910003556 H2 SO4 Inorganic materials 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
• FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• 108010065942 Prostaglandin-F synthase Proteins 0.000 description 2
• 206010037124 Pseudohermaphroditism male Diseases 0.000 description 2
• 244000000231 Sesamum indicum Species 0.000 description 2
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
• 101000857870 Squalus acanthias Gonadoliberin Proteins 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 2
• XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 2
• AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• 230000009471 action Effects 0.000 description 2
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
• 239000002671 adjuvant Substances 0.000 description 2
• 125000005157 alkyl carboxy group Chemical group 0.000 description 2
• 125000005037 alkyl phenyl group Chemical group 0.000 description 2
• 108010080146 androgen receptors Proteins 0.000 description 2
• 229940030486 androgens Drugs 0.000 description 2
• 229940046836 anti-estrogen Drugs 0.000 description 2
• 230000003110 anti-inflammatory effect Effects 0.000 description 2
• 238000000149 argon plasma sintering Methods 0.000 description 2
• 238000005899 aromatization reaction Methods 0.000 description 2
• SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
• 239000008280 blood Substances 0.000 description 2
• 210000004369 blood Anatomy 0.000 description 2
• 230000031709 bromination Effects 0.000 description 2
• DKSMCEUSSQTGBK-UHFFFAOYSA-M bromite Chemical compound [O-]Br=O DKSMCEUSSQTGBK-UHFFFAOYSA-M 0.000 description 2
• 150000001649 bromium compounds Chemical class 0.000 description 2
• 239000000872 buffer Substances 0.000 description 2
• 125000002837 carbocyclic group Chemical group 0.000 description 2
• 150000001721 carbon Chemical group 0.000 description 2
• 150000001735 carboxylic acids Chemical class 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• 239000003874 central nervous system depressant Substances 0.000 description 2
• 239000003795 chemical substances by application Substances 0.000 description 2
• 150000001805 chlorine compounds Chemical class 0.000 description 2
• HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical class CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
• 238000004440 column chromatography Methods 0.000 description 2
• 239000012141 concentrate Substances 0.000 description 2
• 235000008504 concentrate Nutrition 0.000 description 2
• 238000002425 crystallisation Methods 0.000 description 2
• 230000008025 crystallization Effects 0.000 description 2
• 125000000753 cycloalkyl group Chemical group 0.000 description 2
• ZJUGSKJHHWASAF-UHFFFAOYSA-N cyclohexylazanium;chloride Chemical compound [Cl-].[NH3+]C1CCCCC1 ZJUGSKJHHWASAF-UHFFFAOYSA-N 0.000 description 2
• SIIJRCRHAIMFNT-UHFFFAOYSA-N cyclopropanamine;hydrochloride Chemical compound Cl.NC1CC1 SIIJRCRHAIMFNT-UHFFFAOYSA-N 0.000 description 2
• IHFWMWVUSYTWDE-XWTMOSNGSA-N dimethamine Chemical compound C1[C@H](CN2C3=O)CN(C)C[C@H]1C2=CC=C3C(CCC(=O)N1C2)=C1[C@@H]1C[C@@H]2CN(C)C1 IHFWMWVUSYTWDE-XWTMOSNGSA-N 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 208000037765 diseases and disorders Diseases 0.000 description 2
• 239000002270 dispersing agent Substances 0.000 description 2
• 238000009826 distribution Methods 0.000 description 2
• 239000003995 emulsifying agent Substances 0.000 description 2
• 102000015694 estrogen receptors Human genes 0.000 description 2
• 230000001605 fetal effect Effects 0.000 description 2
• 125000001153 fluoro group Chemical group F* 0.000 description 2
• 235000019253 formic acid Nutrition 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 125000000623 heterocyclic group Chemical group 0.000 description 2
• 238000004128 high performance liquid chromatography Methods 0.000 description 2
• 230000003054 hormonal effect Effects 0.000 description 2
• 238000001794 hormone therapy Methods 0.000 description 2
• 229930195733 hydrocarbon Natural products 0.000 description 2
• 230000002779 inactivation Effects 0.000 description 2
• 238000011534 incubation Methods 0.000 description 2
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 2
• 230000003834 intracellular effect Effects 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 239000010410 layer Substances 0.000 description 2
• 239000003446 ligand Substances 0.000 description 2
• 239000002502 liposome Substances 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• 230000014759 maintenance of location Effects 0.000 description 2
• 230000007246 mechanism Effects 0.000 description 2
• WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
• 230000035772 mutation Effects 0.000 description 2
• 210000000754 myometrium Anatomy 0.000 description 2
• IUHYGONSJUAHBM-UHFFFAOYSA-N n-benzyl-3,4,5-trimethoxybenzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NCC=2C=CC=CC=2)=C1 IUHYGONSJUAHBM-UHFFFAOYSA-N 0.000 description 2
• DVKYBNATNLOJEM-UHFFFAOYSA-N n-chlorocyclopropanamine Chemical compound ClNC1CC1 DVKYBNATNLOJEM-UHFFFAOYSA-N 0.000 description 2
• 239000003921 oil Substances 0.000 description 2
• 235000019198 oils Nutrition 0.000 description 2
• TUXSUKLRDNJDOR-UHFFFAOYSA-N oxolan-2-ylmethylazanium;chloride Chemical compound [Cl-].[NH3+]CC1CCCO1 TUXSUKLRDNJDOR-UHFFFAOYSA-N 0.000 description 2
• 239000002953 phosphate buffered saline Substances 0.000 description 2
• 210000002826 placenta Anatomy 0.000 description 2
• 230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 2
• 239000003755 preservative agent Substances 0.000 description 2
• 239000000651 prodrug Substances 0.000 description 2
• 229940002612 prodrug Drugs 0.000 description 2
• 108090000623 proteins and genes Proteins 0.000 description 2
• AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
• 238000001525 receptor binding assay Methods 0.000 description 2
• 230000009467 reduction Effects 0.000 description 2
• 230000001850 reproductive effect Effects 0.000 description 2
• 230000004044 response Effects 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 239000001632 sodium acetate Substances 0.000 description 2
• 235000017281 sodium acetate Nutrition 0.000 description 2
• DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
• 239000012265 solid product Substances 0.000 description 2
• 230000003637 steroidlike Effects 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• 125000004434 sulfur atom Chemical group 0.000 description 2
• 239000004094 surface-active agent Substances 0.000 description 2
• 238000001356 surgical procedure Methods 0.000 description 2
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
• WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
• GFZLEUSLQORNJJ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine 5-oxide Chemical class C1=NC=C2S(=O)C=CC2=N1 GFZLEUSLQORNJJ-UHFFFAOYSA-N 0.000 description 2
• QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 2
• 230000000699 topical effect Effects 0.000 description 2
• YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
• RWBRUCCWZPSBFC-SJOKZOANSA-N (20R)-20-hydroxypregn-4-en-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](O)C)[C@@]1(C)CC2 RWBRUCCWZPSBFC-SJOKZOANSA-N 0.000 description 1
• LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
• IXHNFOOSLAWRBQ-UHFFFAOYSA-N (3,4-dichlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C(Cl)=C1 IXHNFOOSLAWRBQ-UHFFFAOYSA-N 0.000 description 1
• ZYNAMGYRDACTHK-UHFFFAOYSA-N (3,4-dichlorophenyl)methanamine 2,6-difluorobenzoyl chloride Chemical compound ClC=1C=C(CN)C=CC1Cl.FC1=C(C(=O)Cl)C(=CC=C1)F ZYNAMGYRDACTHK-UHFFFAOYSA-N 0.000 description 1
• OLFUPHOOXXQFOK-UHFFFAOYSA-N (3-benzyl-4,8-dioxo-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidin-2-yl)methyl acetate Chemical compound CC(=O)OCC1=NC=2SC(C(CCC3)=O)=C3C=2C(=O)N1CC1=CC=CC=C1 OLFUPHOOXXQFOK-UHFFFAOYSA-N 0.000 description 1
• BBYBMTKUVVVTSE-UHFFFAOYSA-N (3-benzyl-4-oxo-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl)methyl acetate Chemical compound CC(=O)OCC1=NC=2SC=3CCCCC=3C=2C(=O)N1CC1=CC=CC=C1 BBYBMTKUVVVTSE-UHFFFAOYSA-N 0.000 description 1
• DLUFGSSNIBZCNZ-UHFFFAOYSA-N (3-chlorothiophen-2-yl)methanamine Chemical compound NCC=1SC=CC=1Cl DLUFGSSNIBZCNZ-UHFFFAOYSA-N 0.000 description 1
• 102100022582 (3R)-3-hydroxyacyl-CoA dehydrogenase Human genes 0.000 description 1
• 101710120738 (3R)-3-hydroxyacyl-CoA dehydrogenase Proteins 0.000 description 1
• VYCRIPVKOJTSLP-UHFFFAOYSA-N (4-oxo-3-phenyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-2-yl)methyl acetate Chemical compound CC(=O)OCC1=NC=2SC=3CCCCC=3C=2C(=O)N1C1=CC=CC=C1 VYCRIPVKOJTSLP-UHFFFAOYSA-N 0.000 description 1
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 1
• 125000006529 (C3-C6) alkyl group Chemical group 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 1
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical group C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
• SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 description 1
• QMQDOJKBGXQCRR-UHFFFAOYSA-N 1,4-dichloro-4-methylpentane Chemical compound CC(C)(Cl)CCCCl QMQDOJKBGXQCRR-UHFFFAOYSA-N 0.000 description 1
• RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
• OFHAGSNEHHNRSV-UHFFFAOYSA-N 1-benzothiophene;hydrochloride Chemical compound Cl.C1=CC=C2SC=CC2=C1 OFHAGSNEHHNRSV-UHFFFAOYSA-N 0.000 description 1
• LIJPUYWRAJPDLJ-UHFFFAOYSA-N 1-benzyl-1,2,3,4-tetrahydronaphthalene Chemical class C1CCC2=CC=CC=C2C1CC1=CC=CC=C1 LIJPUYWRAJPDLJ-UHFFFAOYSA-N 0.000 description 1
• YUBDLZGUSSWQSS-UHFFFAOYSA-N 1-benzylpiperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=CC=C1 YUBDLZGUSSWQSS-UHFFFAOYSA-N 0.000 description 1
• RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
• XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical class C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 1
• 102000054917 17-beta-hydroxysteroid dehydrogenase type 3 Human genes 0.000 description 1
• NWQWQKUXRJYXFH-UHFFFAOYSA-N 2,2-Dichloroacetaldehyde Chemical compound ClC(Cl)C=O NWQWQKUXRJYXFH-UHFFFAOYSA-N 0.000 description 1
• NMKWKTZCPBLCJI-UHFFFAOYSA-N 2,2-diphenylethanamine;hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(C[NH3+])C1=CC=CC=C1 NMKWKTZCPBLCJI-UHFFFAOYSA-N 0.000 description 1
• OHYTXVVDBLCEOX-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran;hydrochloride Chemical compound Cl.C1=CC=C2OCCC2=C1 OHYTXVVDBLCEOX-UHFFFAOYSA-N 0.000 description 1
• IAPLQJOOHWDUGK-UHFFFAOYSA-N 2,4-dichlorobenzoyl chloride 2-phenoxyethanamine Chemical compound O(C1=CC=CC=C1)CCN.ClC1=C(C(=O)Cl)C=CC(=C1)Cl IAPLQJOOHWDUGK-UHFFFAOYSA-N 0.000 description 1
• CPTNVUZMWSFCGO-UHFFFAOYSA-N 2,6-difluoro-n-(2-phenoxyethyl)benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NCCOC1=CC=CC=C1 CPTNVUZMWSFCGO-UHFFFAOYSA-N 0.000 description 1
• JAWVDAMHURMGFO-UHFFFAOYSA-N 2-(2-bromo-3,4,5-trimethoxyphenyl)-8-hydroxy-3-(oxolan-2-ylmethyl)-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=CC=CC(O)=C4SC=3N=2)CC2OCCC2)=C1Br JAWVDAMHURMGFO-UHFFFAOYSA-N 0.000 description 1
• GRTWYIODJKVPEV-UHFFFAOYSA-N 2-(2-methylphenyl)pyridine Chemical compound CC1=CC=CC=C1C1=CC=CC=N1 GRTWYIODJKVPEV-UHFFFAOYSA-N 0.000 description 1
• OODRWLGKUBMFLZ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methylpropanoyl chloride Chemical compound ClC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 OODRWLGKUBMFLZ-UHFFFAOYSA-N 0.000 description 1
• GJYPPILDXASUIW-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-phenyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(N(C1=O)C=2C=CC=CC=2)=NC2=C1C(CCCC1)=C1S2 GJYPPILDXASUIW-UHFFFAOYSA-N 0.000 description 1
• WHSUXHFTSNTATH-UHFFFAOYSA-N 2-(hydroxymethyl)-3-phenyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound OCC1=NC=2SC=3CCCCC=3C=2C(=O)N1C1=CC=CC=C1 WHSUXHFTSNTATH-UHFFFAOYSA-N 0.000 description 1
• XPOVKASSWSSLDX-UHFFFAOYSA-N 2-(methoxymethyl)-3-phenyl-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COCC1=NC=2SC(C(CCC3)=O)=C3C=2C(=O)N1C1=CC=CC=C1 XPOVKASSWSSLDX-UHFFFAOYSA-N 0.000 description 1
• GMYDEDCMIQAOCT-UHFFFAOYSA-N 2-amino-1-phenylethanol;hydrochloride Chemical compound [Cl-].[NH3+]CC(O)C1=CC=CC=C1 GMYDEDCMIQAOCT-UHFFFAOYSA-N 0.000 description 1
• YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
• VVIABLBSEYWMNY-UHFFFAOYSA-N 2-aminoethanol 2,4-dichlorobenzoyl chloride Chemical compound C(O)CN.ClC1=C(C(=O)Cl)C=CC(=C1)Cl VVIABLBSEYWMNY-UHFFFAOYSA-N 0.000 description 1
• WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 1
• LUHVQTIAVRHOCA-UHFFFAOYSA-N 2-benzylthieno[3,2-d]pyrimidine 5-oxide Chemical class N=1C=C2S(=O)C=CC2=NC=1CC1=CC=CC=C1 LUHVQTIAVRHOCA-UHFFFAOYSA-N 0.000 description 1
• JXCHIQZWJKXVQC-UHFFFAOYSA-N 2-chloroethylbenzene 2-phenylethanamine Chemical compound NCCC1=CC=CC=C1.ClCCC1=CC=CC=C1 JXCHIQZWJKXVQC-UHFFFAOYSA-N 0.000 description 1
• CGYGETOMCSJHJU-UHFFFAOYSA-N 2-chloronaphthalene Chemical compound C1=CC=CC2=CC(Cl)=CC=C21 CGYGETOMCSJHJU-UHFFFAOYSA-N 0.000 description 1
• IJJJSNBMFDDFBC-UHFFFAOYSA-N 2-cyanoethyl acetate Chemical compound CC(=O)OCCC#N IJJJSNBMFDDFBC-UHFFFAOYSA-N 0.000 description 1
• UPJXJBBIJNJQAZ-UHFFFAOYSA-N 2-ethylbutanedioyl dichloride oxolan-2-ylmethanamine Chemical compound C(C1CCCO1)N.C(C)C(C(=O)Cl)CC(=O)Cl UPJXJBBIJNJQAZ-UHFFFAOYSA-N 0.000 description 1
• WFSGQBNCVASPMW-UHFFFAOYSA-N 2-ethylhexanoyl chloride Chemical compound CCCCC(CC)C(Cl)=O WFSGQBNCVASPMW-UHFFFAOYSA-N 0.000 description 1
• OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 1
• LEQAQBFYCMENLP-UHFFFAOYSA-N 2-methoxy-n-phenylacetamide Chemical compound COCC(=O)NC1=CC=CC=C1 LEQAQBFYCMENLP-UHFFFAOYSA-N 0.000 description 1
• 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
• ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
• JHALVXMWEIDCNP-UHFFFAOYSA-N 2-methyl-3-phenyl-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound CC1=NC=2SC(C(CCC3)=O)=C3C=2C(=O)N1C1=CC=CC=C1 JHALVXMWEIDCNP-UHFFFAOYSA-N 0.000 description 1
• XWGXLRRTBBCVMC-UHFFFAOYSA-N 2-methylbutanedioyl dichloride Chemical compound ClC(=O)C(C)CC(Cl)=O XWGXLRRTBBCVMC-UHFFFAOYSA-N 0.000 description 1
• 125000005916 2-methylpentyl group Chemical group 0.000 description 1
• IYAWBVSACPDZBW-UHFFFAOYSA-N 2-morpholin-2-ylethanamine Chemical compound NCCC1CNCCO1 IYAWBVSACPDZBW-UHFFFAOYSA-N 0.000 description 1
• BVERDZDSLLMYLC-UHFFFAOYSA-N 2-morpholin-4-ylethanamine;hydrochloride Chemical compound Cl.NCCN1CCOCC1 BVERDZDSLLMYLC-UHFFFAOYSA-N 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• IVBZTQOOIWVUEK-UHFFFAOYSA-N 3,4,5-trimethoxy-n-(2-methylbutyl)benzamide Chemical compound CCC(C)CNC(=O)C1=CC(OC)=C(OC)C(OC)=C1 IVBZTQOOIWVUEK-UHFFFAOYSA-N 0.000 description 1
• ISESBRZEYWFXAE-UHFFFAOYSA-N 3,4,5-trimethoxy-n-(2-methylpropyl)benzamide Chemical compound COC1=CC(C(=O)NCC(C)C)=CC(OC)=C1OC ISESBRZEYWFXAE-UHFFFAOYSA-N 0.000 description 1
• ALGAPMXFTBJIPJ-UHFFFAOYSA-N 3,4,5-trimethoxy-n-(oxolan-2-ylmethyl)benzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NCC2OCCC2)=C1 ALGAPMXFTBJIPJ-UHFFFAOYSA-N 0.000 description 1
• PCAHHUDNCNWNIG-UHFFFAOYSA-N 3,4,5-trimethoxy-n-phenylbenzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NC=2C=CC=CC=2)=C1 PCAHHUDNCNWNIG-UHFFFAOYSA-N 0.000 description 1
• BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 1
• ZZGHGUQIHJJZKN-UHFFFAOYSA-N 3,4-dichlorobenzoyl chloride 2-thiophen-2-ylethanamine Chemical compound S1C(=CC=C1)CCN.ClC=1C=C(C(=O)Cl)C=CC1Cl ZZGHGUQIHJJZKN-UHFFFAOYSA-N 0.000 description 1
• WAKMMQSMEDJRRI-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC(C(Cl)=O)=CC(C(F)(F)F)=C1 WAKMMQSMEDJRRI-UHFFFAOYSA-N 0.000 description 1
• XDWBMUOFXOKDNB-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-ylmethyl)-8-hydroxy-2-(2-methoxyphenyl)-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=CC=CC=C1C(N(C1=O)CC=2C=C3OCOC3=CC=2)=NC2=C1C1=CC=CC(O)=C1S2 XDWBMUOFXOKDNB-UHFFFAOYSA-N 0.000 description 1
• LVLOPTDNFFBZEJ-UHFFFAOYSA-N 3-(2-aminoethyl)benzenesulfonamide Chemical compound NCCC1=CC=CC(S(N)(=O)=O)=C1 LVLOPTDNFFBZEJ-UHFFFAOYSA-N 0.000 description 1
• VWXCTFPACYMQDS-UHFFFAOYSA-N 3-(2-methoxyethyl)-2-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound N=1C=2SC=3CCCCC=3C=2C(=O)N(CCOC)C=1C1=CC(OC)=C(OC)C(OC)=C1 VWXCTFPACYMQDS-UHFFFAOYSA-N 0.000 description 1
• MVJODCUZHBGKAI-UHFFFAOYSA-N 3-(2-methoxyethyl)-2-thiophen-2-yl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound N=1C=2SC=3CCCCC=3C=2C(=O)N(CCOC)C=1C1=CC=CS1 MVJODCUZHBGKAI-UHFFFAOYSA-N 0.000 description 1
• CIWSNDMNKHZEDT-UHFFFAOYSA-N 3-(2-methoxyethyl)-2-thiophen-2-yl-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound N=1C=2SC(C(CCC3)=O)=C3C=2C(=O)N(CCOC)C=1C1=CC=CS1 CIWSNDMNKHZEDT-UHFFFAOYSA-N 0.000 description 1
• FALRCEOQUHSKGC-UHFFFAOYSA-N 3-(furan-2-ylmethyl)-2-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C=4CCCCC=4SC=3N=2)CC=2OC=CC=2)=C1 FALRCEOQUHSKGC-UHFFFAOYSA-N 0.000 description 1
• LZYDCGUBNXAXPD-UHFFFAOYSA-N 3-(oxolan-2-ylmethyl)-2-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C=4CCCCC=4SC=3N=2)CC2OCCC2)=C1 LZYDCGUBNXAXPD-UHFFFAOYSA-N 0.000 description 1
• JXLKZBONACBOME-UHFFFAOYSA-N 3-(oxolan-2-ylmethyl)-2-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=C(C(CCC4)=O)SC=3N=2)CC2OCCC2)=C1 JXLKZBONACBOME-UHFFFAOYSA-N 0.000 description 1
• WUROSBWCHFRWAM-UHFFFAOYSA-N 3-(pyridin-3-ylmethyl)-2-(3,4,5-trimethylphenyl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound CC1=C(C)C(C)=CC(C=2N(C(=O)C=3C=4CCCCC=4SC=3N=2)CC=2C=NC=CC=2)=C1 WUROSBWCHFRWAM-UHFFFAOYSA-N 0.000 description 1
• VVQWCIXBRCHDBW-UHFFFAOYSA-N 3-[2-[4-(2,4-difluorobenzoyl)piperidin-1-yl]ethyl]-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical class CC=1N=C2CCCCN2C(=O)C=1CCN(CC1)CCC1C(=O)C1=CC=C(F)C=C1F VVQWCIXBRCHDBW-UHFFFAOYSA-N 0.000 description 1
• BGAJNPLDJJBRHK-UHFFFAOYSA-N 3-[2-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-3-methyl-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NN=C(N2C(=C3CN(CCC(O)=O)CCC3=N2)C)S1 BGAJNPLDJJBRHK-UHFFFAOYSA-N 0.000 description 1
• ZAGZIOYVEIDDJA-UHFFFAOYSA-N 3-aminopyrazine-2-carboxylic acid Chemical compound NC1=NC=CN=C1C(O)=O ZAGZIOYVEIDDJA-UHFFFAOYSA-N 0.000 description 1
• MIJSYHUMKXEFQH-UHFFFAOYSA-N 3-benzyl-2-(2-bromo-3,4,5-trimethoxyphenyl)-8-hydroxy-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=CC=CC(O)=C4SC=3N=2)CC=2C=CC=CC=2)=C1Br MIJSYHUMKXEFQH-UHFFFAOYSA-N 0.000 description 1
• HBUFJIKNBMAOPL-UHFFFAOYSA-N 3-benzyl-2-(2-bromo-3,4,5-trimethoxyphenyl)-8-methoxy-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=CC=CC(OC)=C4SC=3N=2)CC=2C=CC=CC=2)=C1Br HBUFJIKNBMAOPL-UHFFFAOYSA-N 0.000 description 1
• OXKZOICCNIWGHP-UHFFFAOYSA-N 3-benzyl-2-(3,4,5-trihydroxyphenyl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound OC1=C(O)C(O)=CC(C=2N(C(=O)C=3C=4CCCCC=4SC=3N=2)CC=2C=CC=CC=2)=C1 OXKZOICCNIWGHP-UHFFFAOYSA-N 0.000 description 1
• LODPQKHLOIFTJV-UHFFFAOYSA-N 3-benzyl-2-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=C(C(CCC4)=O)SC=3N=2)CC=2C=CC=CC=2)=C1 LODPQKHLOIFTJV-UHFFFAOYSA-N 0.000 description 1
• CLSPXKVXATZQDX-UHFFFAOYSA-N 3-benzyl-2-(3-methoxyphenyl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=CC=CC(C=2N(C(=O)C=3C=4CCCCC=4SC=3N=2)CC=2C=CC=CC=2)=C1 CLSPXKVXATZQDX-UHFFFAOYSA-N 0.000 description 1
• PLXIHHQVGBJKBR-UHFFFAOYSA-N 3-benzyl-2-(3-methoxyphenyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COC1=CC=CC(C=2N(C(=O)C=3C4=C(C(CCC4)=O)SC=3N=2)CC=2C=CC=CC=2)=C1 PLXIHHQVGBJKBR-UHFFFAOYSA-N 0.000 description 1
• JDNWDUUEUOBELL-UHFFFAOYSA-N 3-benzyl-2-(4-methoxyphenyl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(N(C1=O)CC=2C=CC=CC=2)=NC2=C1C(CCCC1)=C1S2 JDNWDUUEUOBELL-UHFFFAOYSA-N 0.000 description 1
• BLBSEQMNSPZMJT-UHFFFAOYSA-N 3-benzyl-2-(4-methoxyphenyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound C1=CC(OC)=CC=C1C(N(C1=O)CC=2C=CC=CC=2)=NC2=C1C(CCCC1=O)=C1S2 BLBSEQMNSPZMJT-UHFFFAOYSA-N 0.000 description 1
• VHKKOYCAWAPTIB-UHFFFAOYSA-N 3-benzyl-2-(5-bromothiophen-2-yl)-8-hydroxy-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound OC1=CC=CC(C=2C(=O)N3CC=4C=CC=CC=4)=C1SC=2N=C3C1=CC=C(Br)S1 VHKKOYCAWAPTIB-UHFFFAOYSA-N 0.000 description 1
• NNWWXFSOPUJMRQ-UHFFFAOYSA-N 3-benzyl-2-(methoxymethyl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COCC1=NC=2SC=3CCCCC=3C=2C(=O)N1CC1=CC=CC=C1 NNWWXFSOPUJMRQ-UHFFFAOYSA-N 0.000 description 1
• SIKDQGNHTTWRSW-UHFFFAOYSA-N 3-benzyl-2-(methoxymethyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COCC1=NC=2SC(C(CCC3)=O)=C3C=2C(=O)N1CC1=CC=CC=C1 SIKDQGNHTTWRSW-UHFFFAOYSA-N 0.000 description 1
• WZFMSNIKPXEQRV-UHFFFAOYSA-N 3-benzyl-2-phenyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound C=1C=CC=CC=1C1=NC=2SC=3CCCCC=3C=2C(=O)N1CC1=CC=CC=C1 WZFMSNIKPXEQRV-UHFFFAOYSA-N 0.000 description 1
• PJAXSIZTIAQZIE-UHFFFAOYSA-N 3-benzyl-2-phenyl-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound O=C1CCCC(C=2C(=O)N3CC=4C=CC=CC=4)=C1SC=2N=C3C1=CC=CC=C1 PJAXSIZTIAQZIE-UHFFFAOYSA-N 0.000 description 1
• WXVXINABPFCQED-UHFFFAOYSA-N 3-benzyl-2-thiophen-2-yl-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound O=C1CCCC(C=2C(=O)N3CC=4C=CC=CC=4)=C1SC=2N=C3C1=CC=CS1 WXVXINABPFCQED-UHFFFAOYSA-N 0.000 description 1
• QPYOQQFCCXHEPL-UHFFFAOYSA-N 3-benzyl-4-oxo-8-phenoxy-2-(3,4,5-trimethoxyphenyl)-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-7-carbaldehyde Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=C(C(=C(C=O)CC4)OC=4C=CC=CC=4)SC=3N=2)CC=2C=CC=CC=2)=C1 QPYOQQFCCXHEPL-UHFFFAOYSA-N 0.000 description 1
• DLYWJYDANFJOCX-UHFFFAOYSA-N 3-benzyl-4-oxo-8-phenoxy-2-(3,4,5-trimethoxyphenyl)-[1]benzothiolo[2,3-d]pyrimidine-7-carbaldehyde Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=CC=C(C=O)C(OC=5C=CC=CC=5)=C4SC=3N=2)CC=2C=CC=CC=2)=C1 DLYWJYDANFJOCX-UHFFFAOYSA-N 0.000 description 1
• CBQMYGCXDHJJTN-UHFFFAOYSA-N 3-benzyl-5-bromo-2-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=C(C(CCC4Br)=O)SC=3N=2)CC=2C=CC=CC=2)=C1 CBQMYGCXDHJJTN-UHFFFAOYSA-N 0.000 description 1
• DAEJRVZPMISZNO-UHFFFAOYSA-N 3-benzyl-7,7-dibromo-2-(2-bromo-3,4,5-trimethoxyphenyl)-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=C(C(C(Br)(Br)CC4)=O)SC=3N=2)CC=2C=CC=CC=2)=C1Br DAEJRVZPMISZNO-UHFFFAOYSA-N 0.000 description 1
• UZJKALMHAXCSDB-UHFFFAOYSA-N 3-benzyl-7,7-dibromo-2-(3-bromo-5-methoxyphenyl)-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COC1=CC(Br)=CC(C=2N(C(=O)C=3C4=C(C(C(Br)(Br)CC4)=O)SC=3N=2)CC=2C=CC=CC=2)=C1 UZJKALMHAXCSDB-UHFFFAOYSA-N 0.000 description 1
• FCOIAPTVVVCJNK-UHFFFAOYSA-N 3-benzyl-7,7-dibromo-2-(4-methoxyphenyl)-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound C1=CC(OC)=CC=C1C(N(C1=O)CC=2C=CC=CC=2)=NC2=C1C(CCC(Br)(Br)C1=O)=C1S2 FCOIAPTVVVCJNK-UHFFFAOYSA-N 0.000 description 1
• AUKSAEUUCAWDHK-UHFFFAOYSA-N 3-benzyl-7,7-dibromo-2-(5-bromothiophen-2-yl)-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound S1C(Br)=CC=C1C(N(C1=O)CC=2C=CC=CC=2)=NC2=C1C(CCC(Br)(Br)C1=O)=C1S2 AUKSAEUUCAWDHK-UHFFFAOYSA-N 0.000 description 1
• WHMBJFRKPPEOQV-UHFFFAOYSA-N 3-benzyl-7-bromo-2-(2-bromo-3,4,5-trimethoxyphenyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=C(C(C(Br)CC4)=O)SC=3N=2)CC=2C=CC=CC=2)=C1Br WHMBJFRKPPEOQV-UHFFFAOYSA-N 0.000 description 1
• MHUXOOUHKVCLCH-UHFFFAOYSA-N 3-benzyl-7-bromo-2-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=C(C(C(Br)CC4)=O)SC=3N=2)CC=2C=CC=CC=2)=C1 MHUXOOUHKVCLCH-UHFFFAOYSA-N 0.000 description 1
• ULDRQDFFFNQXRZ-UHFFFAOYSA-N 3-benzyl-7-bromo-2-(3-methoxyphenyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COC1=CC=CC(C=2N(C(=O)C=3C4=C(C(C(Br)CC4)=O)SC=3N=2)CC=2C=CC=CC=2)=C1 ULDRQDFFFNQXRZ-UHFFFAOYSA-N 0.000 description 1
• BAWWUQUWAHUZGC-UHFFFAOYSA-N 3-benzyl-7-bromo-2-(4-methoxyphenyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound C1=CC(OC)=CC=C1C(N(C1=O)CC=2C=CC=CC=2)=NC2=C1C(CCC(Br)C1=O)=C1S2 BAWWUQUWAHUZGC-UHFFFAOYSA-N 0.000 description 1
• DZZXSJKEGLHANE-UHFFFAOYSA-N 3-benzyl-7-bromo-2-(5-bromothiophen-2-yl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound O=C1C(Br)CCC(C=2C(=O)N3CC=4C=CC=CC=4)=C1SC=2N=C3C1=CC=C(Br)S1 DZZXSJKEGLHANE-UHFFFAOYSA-N 0.000 description 1
• RUYVBGHJZXUEHC-UHFFFAOYSA-N 3-benzyl-8-chloro-2-(2-chloro-3,4,5-trimethoxyphenyl)-4-oxo-[1]benzothiolo[2,3-d]pyrimidine-7-carbaldehyde Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=CC=C(C=O)C(Cl)=C4SC=3N=2)CC=2C=CC=CC=2)=C1Cl RUYVBGHJZXUEHC-UHFFFAOYSA-N 0.000 description 1
• ZEAJKQDSKBQRGY-UHFFFAOYSA-N 3-benzyl-8-ethoxy-4-oxo-2-(3,4,5-trimethoxyphenyl)-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-7-carbaldehyde Chemical compound CCOC1=C(C=O)CCC(C=2C(=O)N3CC=4C=CC=CC=4)=C1SC=2N=C3C1=CC(OC)=C(OC)C(OC)=C1 ZEAJKQDSKBQRGY-UHFFFAOYSA-N 0.000 description 1
• XMNTUMHCOWDSJE-UHFFFAOYSA-N 3-benzyl-8-ethylsulfanyl-4-oxo-2-(3,4,5-trimethoxyphenyl)-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-7-carbaldehyde Chemical compound CCSC1=C(C=O)CCC(C=2C(=O)N3CC=4C=CC=CC=4)=C1SC=2N=C3C1=CC(OC)=C(OC)C(OC)=C1 XMNTUMHCOWDSJE-UHFFFAOYSA-N 0.000 description 1
• QDVKOTFSULVAST-UHFFFAOYSA-N 3-benzyl-8-hydroxy-2-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C=4CCCC(O)C=4SC=3N=2)CC=2C=CC=CC=2)=C1 QDVKOTFSULVAST-UHFFFAOYSA-N 0.000 description 1
• LUJUGAFUEKFNRY-UHFFFAOYSA-N 3-benzyl-8-hydroxy-2-(3,4,5-trimethoxyphenyl)-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=CC=CC(O)=C4SC=3N=2)CC=2C=CC=CC=2)=C1 LUJUGAFUEKFNRY-UHFFFAOYSA-N 0.000 description 1
• XPTDTOFYTCYHSF-UHFFFAOYSA-N 3-benzyl-8-hydroxy-2-thiophen-2-yl-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound OC1=CC=CC(C=2C(=O)N3CC=4C=CC=CC=4)=C1SC=2N=C3C1=CC=CS1 XPTDTOFYTCYHSF-UHFFFAOYSA-N 0.000 description 1
• RFVMPZCTJZNJAC-UHFFFAOYSA-N 3-benzyl-8-methoxy-2-(3,4,5-trimethoxyphenyl)-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=CC=CC(OC)=C4SC=3N=2)CC=2C=CC=CC=2)=C1 RFVMPZCTJZNJAC-UHFFFAOYSA-N 0.000 description 1
• UTAYSTYKSTUBKK-UHFFFAOYSA-N 3-butyl-2-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound N=1C=2SC=3CCCCC=3C=2C(=O)N(CCCC)C=1C1=CC(OC)=C(OC)C(OC)=C1 UTAYSTYKSTUBKK-UHFFFAOYSA-N 0.000 description 1
• NGLPEXAUQDYNFM-UHFFFAOYSA-N 3-butyl-2-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound N=1C=2SC(C(CCC3)=O)=C3C=2C(=O)N(CCCC)C=1C1=CC(OC)=C(OC)C(OC)=C1 NGLPEXAUQDYNFM-UHFFFAOYSA-N 0.000 description 1
• XFHQWOGMVXJHCL-UHFFFAOYSA-N 3-butyl-2-thiophen-2-yl-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound N=1C=2SC(C(CCC3)=O)=C3C=2C(=O)N(CCCC)C=1C1=CC=CS1 XFHQWOGMVXJHCL-UHFFFAOYSA-N 0.000 description 1
• RPESZQVUWMFBEO-UHFFFAOYSA-N 3-cyanobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(C#N)=C1 RPESZQVUWMFBEO-UHFFFAOYSA-N 0.000 description 1
• WCGOYSNWWKKLCM-UHFFFAOYSA-N 3-cyanobenzoyl chloride (3,4-dichlorophenyl)methanamine Chemical compound ClC=1C=C(CN)C=CC1Cl.C(#N)C=1C=C(C(=O)Cl)C=CC1 WCGOYSNWWKKLCM-UHFFFAOYSA-N 0.000 description 1
• HQKVVFMIBPIOKT-UHFFFAOYSA-N 3-fluorobenzoyl chloride 2-phenoxyethanamine Chemical compound O(C1=CC=CC=C1)CCN.FC=1C=C(C(=O)Cl)C=CC1 HQKVVFMIBPIOKT-UHFFFAOYSA-N 0.000 description 1
• 125000005917 3-methylpentyl group Chemical group 0.000 description 1
• MYTQCXFNHQQRME-UHFFFAOYSA-N 3-phenyl-2-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=C(C(CCC4)=O)SC=3N=2)C=2C=CC=CC=2)=C1 MYTQCXFNHQQRME-UHFFFAOYSA-N 0.000 description 1
• OSJPPGNTCRNQQC-UHFFFAOYSA-N 3-phosphoglyceric acid Chemical compound OC(=O)C(O)COP(O)(O)=O OSJPPGNTCRNQQC-UHFFFAOYSA-N 0.000 description 1
• KBSDLBVPAHQCRY-UHFFFAOYSA-N 307496-19-1 Chemical group C1CC=CCC1CC[Si](O1)(O2)O[Si](O3)(C4CCCC4)O[Si](O4)(C5CCCC5)O[Si]1(C1CCCC1)O[Si](O1)(C5CCCC5)O[Si]2(C2CCCC2)O[Si]3(C2CCCC2)O[Si]41C1CCCC1 KBSDLBVPAHQCRY-UHFFFAOYSA-N 0.000 description 1
• ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 1
• QRKCBYHJIGTFSO-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1-benzothiophen-7-ol Chemical class OC1CCCC2=C1SC=C2 QRKCBYHJIGTFSO-UHFFFAOYSA-N 0.000 description 1
• LFRARYNEDYNCOT-UHFFFAOYSA-N 4-(aminomethyl)benzene-1,2-diol;hydrochloride Chemical compound Cl.NCC1=CC=C(O)C(O)=C1 LFRARYNEDYNCOT-UHFFFAOYSA-N 0.000 description 1
• IIQFBBQJYPGOHJ-UHFFFAOYSA-N 4-(cyclohexen-1-yl)morpholine Chemical compound C1CCCC(N2CCOCC2)=C1 IIQFBBQJYPGOHJ-UHFFFAOYSA-N 0.000 description 1
• SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
• XOJAJRFBOKCXPI-UHFFFAOYSA-N 4-methoxy-n-phenylbenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=CC=C1 XOJAJRFBOKCXPI-UHFFFAOYSA-N 0.000 description 1
• YUUFAJOXLZUDJG-UHFFFAOYSA-N 4-methoxybutan-1-amine Chemical compound COCCCCN YUUFAJOXLZUDJG-UHFFFAOYSA-N 0.000 description 1
• JCCFKRNCMIHDFF-UHFFFAOYSA-N 4h-cyclohepta[b]thiophene Chemical compound C1C=CC=CC2=C1C=CS2 JCCFKRNCMIHDFF-UHFFFAOYSA-N 0.000 description 1
• FILWIBNCJYZQTN-UHFFFAOYSA-N 5-oxo-[1]benzothiolo[3,2-d]pyrimidin-8-ol Chemical class C1=NC=C2S(=O)C3=CC=C(O)C=C3C2=N1 FILWIBNCJYZQTN-UHFFFAOYSA-N 0.000 description 1
• QGXBDMJGAMFCBF-HLUDHZFRSA-N 5α-Androsterone Chemical compound C1[C@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 QGXBDMJGAMFCBF-HLUDHZFRSA-N 0.000 description 1
• IPDQHOMJRIQENQ-UHFFFAOYSA-N 7,7-dibromo-2-methyl-3-phenyl-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound CC1=NC=2SC(C(C(Br)(Br)CC3)=O)=C3C=2C(=O)N1C1=CC=CC=C1 IPDQHOMJRIQENQ-UHFFFAOYSA-N 0.000 description 1
• PHZHMMJCUNZTGJ-UHFFFAOYSA-N 7,7-dibromo-3-[(5-bromo-2-methoxyphenyl)methyl]-2-propyl-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound CCCC1=NC=2SC(C(C(Br)(Br)CC3)=O)=C3C=2C(=O)N1CC1=CC(Br)=CC=C1OC PHZHMMJCUNZTGJ-UHFFFAOYSA-N 0.000 description 1
• WCTBOQVJDRVZNO-UHFFFAOYSA-N 7,7-dibromo-3-[(5-bromofuran-2-yl)methyl]-2-propyl-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound CCCC1=NC=2SC(C(C(Br)(Br)CC3)=O)=C3C=2C(=O)N1CC1=CC=C(Br)O1 WCTBOQVJDRVZNO-UHFFFAOYSA-N 0.000 description 1
• BFJFBYPGHVIBTC-UHFFFAOYSA-N 7-bromo-2-(2-bromo-3,4,5-trimethoxyphenyl)-3-(2-methoxyethyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound N=1C=2SC(C(C(Br)CC3)=O)=C3C=2C(=O)N(CCOC)C=1C1=CC(OC)=C(OC)C(OC)=C1Br BFJFBYPGHVIBTC-UHFFFAOYSA-N 0.000 description 1
• XINLGGNUTGZDPU-UHFFFAOYSA-N 7-bromo-3-[(2-methoxyphenyl)methyl]-2-propyl-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound CCCC1=NC=2SC(C(C(Br)CC3)=O)=C3C=2C(=O)N1CC1=CC=CC=C1OC XINLGGNUTGZDPU-UHFFFAOYSA-N 0.000 description 1
• KUUPACSNDFKNRS-UHFFFAOYSA-N 7-bromo-3-[(5-bromofuran-2-yl)methyl]-2-propyl-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound CCCC1=NC=2SC(C(C(Br)CC3)=O)=C3C=2C(=O)N1CC1=CC=C(Br)O1 KUUPACSNDFKNRS-UHFFFAOYSA-N 0.000 description 1
• ISLDBGFKPFKEGN-UHFFFAOYSA-N 7-bromo-3-[(5-bromofuran-2-yl)methyl]-8-hydroxy-2-propyl-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound CCCC1=NC=2SC3=C(O)C(Br)=CC=C3C=2C(=O)N1CC1=CC=C(Br)O1 ISLDBGFKPFKEGN-UHFFFAOYSA-N 0.000 description 1
• QRHOTVHBNYWIGU-UHFFFAOYSA-N 7-bromo-3-butyl-8-hydroxy-2-(3,4,5-trimethoxyphenyl)-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound N=1C=2SC3=C(O)C(Br)=CC=C3C=2C(=O)N(CCCC)C=1C1=CC(OC)=C(OC)C(OC)=C1 QRHOTVHBNYWIGU-UHFFFAOYSA-N 0.000 description 1
• LMFKGUPUNZNTDW-UHFFFAOYSA-N 7-chloro-2-(2-chloro-3,4,5-trimethoxyphenyl)-3-(2-methylbutyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound N=1C=2SC(C(C(Cl)CC3)=O)=C3C=2C(=O)N(CC(C)CC)C=1C1=CC(OC)=C(OC)C(OC)=C1Cl LMFKGUPUNZNTDW-UHFFFAOYSA-N 0.000 description 1
• MEAUAXXEQHWESG-UHFFFAOYSA-N 7-chloro-2-(2-chloro-3,4,5-trimethoxyphenyl)-3-(oxolan-2-ylmethyl)-6,7-dihydro-5h-[1]benzothiolo[2,3-d]pyrimidine-4,8-dione Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=C(C(C(Cl)CC4)=O)SC=3N=2)CC2OCCC2)=C1Cl MEAUAXXEQHWESG-UHFFFAOYSA-N 0.000 description 1
• FDHVLBOUVWGUDD-UHFFFAOYSA-N 8-chloro-2-(4-methoxyphenyl)-4-oxo-3-phenyl-5,6-dihydro-[1]benzothiolo[2,3-d]pyrimidine-7-carbaldehyde Chemical compound C1=CC(OC)=CC=C1C(N(C1=O)C=2C=CC=CC=2)=NC2=C1C(CCC(C=O)=C1Cl)=C1S2 FDHVLBOUVWGUDD-UHFFFAOYSA-N 0.000 description 1
• IVQXONSWINIKHX-UHFFFAOYSA-N 8-hydroxy-3-(2-methylpropyl)-2-(3,4,5-trimethoxyphenyl)-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=CC=CC(O)=C4SC=3N=2)CC(C)C)=C1 IVQXONSWINIKHX-UHFFFAOYSA-N 0.000 description 1
• KHABCFDPXWVPMN-UHFFFAOYSA-N 8-methoxy-3-(2-methylpropyl)-2-(3,4,5-trimethoxyphenyl)-[1]benzothiolo[2,3-d]pyrimidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2N(C(=O)C=3C4=CC=CC(OC)=C4SC=3N=2)CC(C)C)=C1 KHABCFDPXWVPMN-UHFFFAOYSA-N 0.000 description 1
• SYKJOJSYQSVNOM-UHFFFAOYSA-N 9h-fluoren-9-ylazanium;chloride Chemical compound Cl.C1=CC=C2C(N)C3=CC=CC=C3C2=C1 SYKJOJSYQSVNOM-UHFFFAOYSA-N 0.000 description 1
• 244000215068 Acacia senegal Species 0.000 description 1
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
• 108060003345 Adrenergic Receptor Proteins 0.000 description 1
• 102000017910 Adrenergic receptor Human genes 0.000 description 1
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
• 102100032187 Androgen receptor Human genes 0.000 description 1
• KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 1
• 208000033258 Bifunctional enzyme deficiency Diseases 0.000 description 1
• JHMSHSRGLCEXGY-UHFFFAOYSA-N C(C1=CC=2OCOC2C=C1)N.COC1=C(C(=O)Cl)C=CC=C1 Chemical compound C(C1=CC=2OCOC2C=C1)N.COC1=C(C(=O)Cl)C=CC=C1 JHMSHSRGLCEXGY-UHFFFAOYSA-N 0.000 description 1
• OFNIOSSNUNALQM-UHFFFAOYSA-N C(C1=CC=2OCOC2C=C1)N.FC=1C=C(C(=O)Cl)C=CC1 Chemical compound C(C1=CC=2OCOC2C=C1)N.FC=1C=C(C(=O)Cl)C=CC1 OFNIOSSNUNALQM-UHFFFAOYSA-N 0.000 description 1
• CVXKPPFUKWBZPT-UHFFFAOYSA-N C(CCC)N.COC1=C(C(=O)Cl)C=CC=C1 Chemical compound C(CCC)N.COC1=C(C(=O)Cl)C=CC=C1 CVXKPPFUKWBZPT-UHFFFAOYSA-N 0.000 description 1
• BTOWQPUNFZIEBW-UHFFFAOYSA-N C(CCC)N.[Cl] Chemical compound C(CCC)N.[Cl] BTOWQPUNFZIEBW-UHFFFAOYSA-N 0.000 description 1
• CCAWYEARIRQUQK-UHFFFAOYSA-N C1C=CC=CC1(CC2=CC=CC=C2)C(=O)N Chemical compound C1C=CC=CC1(CC2=CC=CC=C2)C(=O)N CCAWYEARIRQUQK-UHFFFAOYSA-N 0.000 description 1
• WVNABITYBXWHOB-UHFFFAOYSA-N CCCCC(CC)C(Cl)=O.NCc1ccc2OCOc2c1 Chemical compound CCCCC(CC)C(Cl)=O.NCc1ccc2OCOc2c1 WVNABITYBXWHOB-UHFFFAOYSA-N 0.000 description 1
• WGRYCAMDZAHQMF-UHFFFAOYSA-N CClC Chemical compound CClC WGRYCAMDZAHQMF-UHFFFAOYSA-N 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• BQDDHULWNMQYEM-UHFFFAOYSA-N ClC=1C=C(CN)C=CC1Cl.C(#N)C1=CC=C(C(=O)Cl)C=C1 Chemical compound ClC=1C=C(CN)C=CC1Cl.C(#N)C1=CC=C(C(=O)Cl)C=C1 BQDDHULWNMQYEM-UHFFFAOYSA-N 0.000 description 1
• 108020004414 DNA Proteins 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 238000009007 Diagnostic Kit Methods 0.000 description 1
• 208000027877 Disorders of Sex Development Diseases 0.000 description 1
• 208000004483 Dyspareunia Diseases 0.000 description 1
• 108010085330 Estradiol Receptors Proteins 0.000 description 1
• 101710196141 Estrogen receptor Proteins 0.000 description 1
• 229940122880 Estrogen receptor agonist Drugs 0.000 description 1
• 229940102550 Estrogen receptor antagonist Drugs 0.000 description 1
• OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
• QGXBDMJGAMFCBF-UHFFFAOYSA-N Etiocholanolone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC21 QGXBDMJGAMFCBF-UHFFFAOYSA-N 0.000 description 1
• 235000019973 FDA food additive Nutrition 0.000 description 1
• 108700012941 GNRH1 Proteins 0.000 description 1
• 108010010803 Gelatin Proteins 0.000 description 1
• BJJXHLWLUDYTGC-ANULTFPQSA-N Gestrinone Chemical compound C1CC(=O)C=C2CC[C@@H]([C@H]3[C@@](CC)([C@](CC3)(O)C#C)C=C3)C3=C21 BJJXHLWLUDYTGC-ANULTFPQSA-N 0.000 description 1
• DHCLVCXQIBBOPH-UHFFFAOYSA-N Glycerol 2-phosphate Chemical compound OCC(CO)OP(O)(O)=O DHCLVCXQIBBOPH-UHFFFAOYSA-N 0.000 description 1
• 239000000579 Gonadotropin-Releasing Hormone Substances 0.000 description 1
• 229920000084 Gum arabic Polymers 0.000 description 1
• 208000032843 Hemorrhage Diseases 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• 101000869981 Homo sapiens Dehydrogenase/reductase SDR family member 11 Proteins 0.000 description 1
• 101000882584 Homo sapiens Estrogen receptor Proteins 0.000 description 1
• 102000011145 Hydroxysteroid Dehydrogenases Human genes 0.000 description 1
• 108010062875 Hydroxysteroid Dehydrogenases Proteins 0.000 description 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
• 206010061218 Inflammation Diseases 0.000 description 1
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
• 229930182816 L-glutamine Natural products 0.000 description 1
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
• 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
• 239000002841 Lewis acid Substances 0.000 description 1
• 229910010082 LiAlH Inorganic materials 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 241000713333 Mouse mammary tumor virus Species 0.000 description 1
• WEFXFKCQWITFAC-UHFFFAOYSA-N N-chlorylaniline Chemical compound O=Cl(=O)NC1=CC=CC=C1 WEFXFKCQWITFAC-UHFFFAOYSA-N 0.000 description 1
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
• JBTPFZXCYRLRDI-UHFFFAOYSA-N NCCC1=NC=CC=C1.ClC1=C(C(=O)Cl)C=CC(=C1)Cl Chemical compound NCCC1=NC=CC=C1.ClC1=C(C(=O)Cl)C=CC(=C1)Cl JBTPFZXCYRLRDI-UHFFFAOYSA-N 0.000 description 1
• JDDNQMLEDWFXMZ-UHFFFAOYSA-N NCCN1CCOCC1.ClC1=C(C(=O)Cl)C=CC(=C1)Cl Chemical compound NCCN1CCOCC1.ClC1=C(C(=O)Cl)C=CC(=C1)Cl JDDNQMLEDWFXMZ-UHFFFAOYSA-N 0.000 description 1
• 229910004809 Na2 SO4 Inorganic materials 0.000 description 1
• YKYQRMFUKKKKIF-UHFFFAOYSA-N O(C1=CC=CC=C1)CCN.C(#N)C=1C=C(C(=O)Cl)C=CC1 Chemical compound O(C1=CC=CC=C1)CCN.C(#N)C=1C=C(C(=O)Cl)C=CC1 YKYQRMFUKKKKIF-UHFFFAOYSA-N 0.000 description 1
• MPVCZRJJVJIHRL-UHFFFAOYSA-N O(C1=CC=CC=C1)CCN.COC1=C(C(=O)Cl)C=CC=C1 Chemical compound O(C1=CC=CC=C1)CCN.COC1=C(C(=O)Cl)C=CC=C1 MPVCZRJJVJIHRL-UHFFFAOYSA-N 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 235000019483 Peanut oil Nutrition 0.000 description 1
• 102100022587 Peroxisomal multifunctional enzyme type 2 Human genes 0.000 description 1
• 101710125609 Peroxisomal multifunctional enzyme type 2 Proteins 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 241000288906 Primates Species 0.000 description 1
• 102100025803 Progesterone receptor Human genes 0.000 description 1
• 201000005613 Pseudohermaphroditism Diseases 0.000 description 1
• 239000012980 RPMI-1640 medium Substances 0.000 description 1
• 108700008625 Reporter Genes Proteins 0.000 description 1
• 108091027981 Response element Proteins 0.000 description 1
• RPWWNMTYLIXQMH-UHFFFAOYSA-N S1C(=CC=C1)CCN.ClC1=C(C(=O)Cl)C=CC(=C1)Cl Chemical compound S1C(=CC=C1)CCN.ClC1=C(C(=O)Cl)C=CC(=C1)Cl RPWWNMTYLIXQMH-UHFFFAOYSA-N 0.000 description 1
• RNEWKIRBRGKVDR-UHFFFAOYSA-N S1C(=CC=C1)CCN.FC=1C=C(C(=O)Cl)C=CC1 Chemical compound S1C(=CC=C1)CCN.FC=1C=C(C(=O)Cl)C=CC1 RNEWKIRBRGKVDR-UHFFFAOYSA-N 0.000 description 1
• 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
• 108010085012 Steroid Receptors Proteins 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
• 108010090932 Vitellogenins Proteins 0.000 description 1
• AMZNRTQMWPOWCJ-UHFFFAOYSA-N [1]benzothiolo[3,2-d]pyrimidine 5-oxide Chemical class C1=NC=C2S(=O)C3=CC=CC=C3C2=N1 AMZNRTQMWPOWCJ-UHFFFAOYSA-N 0.000 description 1
• SWLGGRRPGHOZCV-UHFFFAOYSA-N [3-benzyl-2-(3-methoxyphenyl)-4-oxo-[1]benzothiolo[2,3-d]pyrimidin-8-yl] acetate Chemical compound COC1=CC=CC(C=2N(C(=O)C=3C4=CC=CC(OC(C)=O)=C4SC=3N=2)CC=2C=CC=CC=2)=C1 SWLGGRRPGHOZCV-UHFFFAOYSA-N 0.000 description 1
• 230000003187 abdominal effect Effects 0.000 description 1
• 239000000205 acacia gum Substances 0.000 description 1
• 235000010489 acacia gum Nutrition 0.000 description 1
• TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical class C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
• 230000021736 acetylation Effects 0.000 description 1
• 238000006640 acetylation reaction Methods 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 239000008186 active pharmaceutical agent Substances 0.000 description 1
• 150000001266 acyl halides Chemical class 0.000 description 1
• 230000010933 acylation Effects 0.000 description 1
• 238000005917 acylation reaction Methods 0.000 description 1
• 239000000654 additive Substances 0.000 description 1
• 239000001361 adipic acid Substances 0.000 description 1
• 235000011037 adipic acid Nutrition 0.000 description 1
• 239000000674 adrenergic antagonist Substances 0.000 description 1
• 238000011292 agonist therapy Methods 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 150000001299 aldehydes Chemical class 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
• 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
• 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
• 125000005257 alkyl acyl group Chemical group 0.000 description 1
• 150000003973 alkyl amines Chemical class 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 150000001412 amines Chemical class 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 239000000908 ammonium hydroxide Substances 0.000 description 1
• 102000001307 androgen receptors Human genes 0.000 description 1
• 230000001548 androgenic effect Effects 0.000 description 1
• 229940094957 androgens and estrogen Drugs 0.000 description 1
• AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 description 1
• 229960005471 androstenedione Drugs 0.000 description 1
• AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 description 1
• 229940061641 androsterone Drugs 0.000 description 1
• JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
• 230000002280 anti-androgenic effect Effects 0.000 description 1
• 229940121363 anti-inflammatory agent Drugs 0.000 description 1
• 239000002260 anti-inflammatory agent Substances 0.000 description 1
• 238000011861 anti-inflammatory therapy Methods 0.000 description 1
• 230000000840 anti-viral effect Effects 0.000 description 1
• 239000000051 antiandrogen Substances 0.000 description 1
• 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 238000003782 apoptosis assay Methods 0.000 description 1
• 238000013459 approach Methods 0.000 description 1
• 239000003125 aqueous solvent Substances 0.000 description 1
• 150000001491 aromatic compounds Chemical class 0.000 description 1
• 125000005163 aryl sulfanyl group Chemical group 0.000 description 1
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
• HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
• CUNTVNYKYKGHLP-UHFFFAOYSA-N benzenesulfonamide;dihydrochloride Chemical compound Cl.Cl.NS(=O)(=O)C1=CC=CC=C1 CUNTVNYKYKGHLP-UHFFFAOYSA-N 0.000 description 1
• 235000019445 benzyl alcohol Nutrition 0.000 description 1
• 229960002903 benzyl benzoate Drugs 0.000 description 1
• 150000003939 benzylamines Chemical class 0.000 description 1
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 238000004166 bioassay Methods 0.000 description 1
• 230000000740 bleeding effect Effects 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 210000000988 bone and bone Anatomy 0.000 description 1
• 210000002449 bone cell Anatomy 0.000 description 1
• 210000000481 breast Anatomy 0.000 description 1
• VCLCZBKXIDCTKX-UHFFFAOYSA-N butan-1-amine 2-ethylhexanoyl chloride Chemical compound C(CCC)N.C(C)C(C(=O)Cl)CCCC VCLCZBKXIDCTKX-UHFFFAOYSA-N 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
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
• MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• 244000309466 calf Species 0.000 description 1
• 201000011510 cancer Diseases 0.000 description 1
• 239000001569 carbon dioxide Substances 0.000 description 1
• 229910002092 carbon dioxide Inorganic materials 0.000 description 1
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
• MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
• 239000002327 cardiovascular agent Substances 0.000 description 1
• 229940125692 cardiovascular agent Drugs 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 239000012876 carrier material Substances 0.000 description 1
• 239000004359 castor oil Substances 0.000 description 1
• 235000019438 castor oil Nutrition 0.000 description 1
• 230000015556 catabolic process Effects 0.000 description 1
• 230000001364 causal effect Effects 0.000 description 1
• 239000013592 cell lysate Substances 0.000 description 1
• 230000004663 cell proliferation Effects 0.000 description 1
• 230000001413 cellular effect Effects 0.000 description 1
• 239000003610 charcoal Substances 0.000 description 1
• 239000003638 chemical reducing agent Substances 0.000 description 1
• ASDRZZPTJLDISZ-UHFFFAOYSA-N chlorine;pyridine Chemical compound [Cl].C1=CC=NC=C1 ASDRZZPTJLDISZ-UHFFFAOYSA-N 0.000 description 1
• QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 1
• AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 description 1
• 229910001916 chloryl Inorganic materials 0.000 description 1
• 230000001684 chronic effect Effects 0.000 description 1
• 235000015165 citric acid Nutrition 0.000 description 1
• 238000003776 cleavage reaction Methods 0.000 description 1
• 239000011248 coating agent Substances 0.000 description 1
• 238000000576 coating method Methods 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 239000002131 composite material Substances 0.000 description 1
• 229940125782 compound 2 Drugs 0.000 description 1
• 239000000470 constituent Substances 0.000 description 1
• 239000013068 control sample Substances 0.000 description 1
• 238000013270 controlled release Methods 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 239000002537 cosmetic Substances 0.000 description 1
• 235000012343 cottonseed oil Nutrition 0.000 description 1
• 239000002385 cottonseed oil Substances 0.000 description 1
• 239000006071 cream Substances 0.000 description 1
• 239000003431 cross linking reagent Substances 0.000 description 1
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• UQYYMHWDLORBOQ-UHFFFAOYSA-N cyclopropanamine 3-fluorobenzoyl chloride Chemical compound C1(CC1)N.FC=1C=C(C(=O)Cl)C=CC1 UQYYMHWDLORBOQ-UHFFFAOYSA-N 0.000 description 1
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
• POZRVZJJTULAOH-LHZXLZLDSA-N danazol Chemical compound C1[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=CC2=C1C=NO2 POZRVZJJTULAOH-LHZXLZLDSA-N 0.000 description 1
• 229960000766 danazol Drugs 0.000 description 1
• 238000006731 degradation reaction Methods 0.000 description 1
• 230000017858 demethylation Effects 0.000 description 1
• 238000010520 demethylation reaction Methods 0.000 description 1
• 230000008021 deposition Effects 0.000 description 1
• 230000006866 deterioration Effects 0.000 description 1
• 239000000032 diagnostic agent Substances 0.000 description 1
• 229940039227 diagnostic agent Drugs 0.000 description 1
• 238000010586 diagram Methods 0.000 description 1
• NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
• WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
• 235000005911 diet Nutrition 0.000 description 1
• 230000037213 diet Effects 0.000 description 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
• VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
• UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
• 239000000890 drug combination Substances 0.000 description 1
• 230000002500 effect on skin Effects 0.000 description 1
• 238000009261 endocrine therapy Methods 0.000 description 1
• 229940034984 endocrine therapy antineoplastic and immunomodulating agent Drugs 0.000 description 1
• 210000005168 endometrial cell Anatomy 0.000 description 1
• 229940125532 enzyme inhibitor Drugs 0.000 description 1
• 239000003797 essential amino acid Substances 0.000 description 1
• 235000020776 essential amino acid Nutrition 0.000 description 1
• IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
• 150000002170 ethers Chemical class 0.000 description 1
• MYGDFSFTVVUJHF-UHFFFAOYSA-N ethyl 2-acetamido-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate Chemical compound C1CCCC2=C1SC(NC(C)=O)=C2C(=O)OCC MYGDFSFTVVUJHF-UHFFFAOYSA-N 0.000 description 1
• CDCGUOVAAKPRKR-UHFFFAOYSA-N ethyl 2-acetamido-6-bromo-7-oxo-5,6-dihydro-4h-1-benzothiophene-3-carboxylate Chemical compound C1CC(Br)C(=O)C2=C1C(C(=O)OCC)=C(NC(C)=O)S2 CDCGUOVAAKPRKR-UHFFFAOYSA-N 0.000 description 1
• CJBGJHJKMOOCQE-UHFFFAOYSA-N ethyl 2-acetamido-7-hydroxy-1-benzothiophene-3-carboxylate Chemical compound C1=CC=C2C(C(=O)OCC)=C(NC(C)=O)SC2=C1O CJBGJHJKMOOCQE-UHFFFAOYSA-N 0.000 description 1
• JPJXZTHTKNOGNH-UHFFFAOYSA-N ethyl 2-acetamido-7-oxo-5,6-dihydro-4h-1-benzothiophene-3-carboxylate Chemical compound C1CCC(=O)C2=C1C(C(=O)OCC)=C(NC(C)=O)S2 JPJXZTHTKNOGNH-UHFFFAOYSA-N 0.000 description 1
• XNASJEQIJMDBQN-UHFFFAOYSA-N ethyl 2-amino-1-benzothiophene-3-carboxylate Chemical compound C1=CC=C2C(C(=O)OCC)=C(N)SC2=C1 XNASJEQIJMDBQN-UHFFFAOYSA-N 0.000 description 1
• YDGAUBHNAKCSKF-UHFFFAOYSA-N ethyl 2-anilino-2-oxoacetate Chemical compound CCOC(=O)C(=O)NC1=CC=CC=C1 YDGAUBHNAKCSKF-UHFFFAOYSA-N 0.000 description 1
• ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
• ROMCYYOFVGNQRB-UHFFFAOYSA-N ethyl 4-oxo-3-phenyl-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidine-2-carboxylate Chemical compound CCOC(=O)C1=NC=2SC=3CCCCC=3C=2C(=O)N1C1=CC=CC=C1 ROMCYYOFVGNQRB-UHFFFAOYSA-N 0.000 description 1
• 229960003750 ethyl chloride Drugs 0.000 description 1
• 238000011156 evaluation Methods 0.000 description 1
• 230000029142 excretion Effects 0.000 description 1
• 238000001400 expression cloning Methods 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 230000035558 fertility Effects 0.000 description 1
• 239000000945 filler Substances 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 235000011087 fumaric acid Nutrition 0.000 description 1
• 125000000524 functional group Chemical group 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• 239000000499 gel Substances 0.000 description 1
• 239000008273 gelatin Substances 0.000 description 1
• 229920000159 gelatin Polymers 0.000 description 1
• 235000019322 gelatine Nutrition 0.000 description 1
• 235000011852 gelatine desserts Nutrition 0.000 description 1
• 238000007429 general method Methods 0.000 description 1
• 230000008570 general process Effects 0.000 description 1
• 235000021472 generally recognized as safe Nutrition 0.000 description 1
• 229960004761 gestrinone Drugs 0.000 description 1
• 210000004907 gland Anatomy 0.000 description 1
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
• 239000001963 growth medium Substances 0.000 description 1
• 208000024963 hair loss Diseases 0.000 description 1
• 230000003676 hair loss Effects 0.000 description 1
• 230000003862 health status Effects 0.000 description 1
• 125000005253 heteroarylacyl group Chemical group 0.000 description 1
• 125000006038 hexenyl group Chemical group 0.000 description 1
• 108700010802 human intersex Proteins 0.000 description 1
• 102000058032 human intersex Human genes 0.000 description 1
• 150000004679 hydroxides Chemical class 0.000 description 1
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
• 238000009802 hysterectomy Methods 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 239000012729 immediate-release (IR) formulation Substances 0.000 description 1
• 238000002513 implantation Methods 0.000 description 1
• 238000000099 in vitro assay Methods 0.000 description 1
• 238000001727 in vivo Methods 0.000 description 1
• 230000008595 infiltration Effects 0.000 description 1
• 238000001764 infiltration Methods 0.000 description 1
• 230000004054 inflammatory process Effects 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 238000010253 intravenous injection Methods 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 125000000468 ketone group Chemical group 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 150000007517 lewis acids Chemical class 0.000 description 1
• 150000002632 lipids Chemical class 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 239000007791 liquid phase Substances 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
• 229910052808 lithium carbonate Inorganic materials 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 239000012139 lysis buffer Substances 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
• 235000019341 magnesium sulphate Nutrition 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 230000036210 malignancy Effects 0.000 description 1
• 230000003211 malignant effect Effects 0.000 description 1
• 210000005075 mammary gland Anatomy 0.000 description 1
• 238000004949 mass spectrometry Methods 0.000 description 1
• 238000005259 measurement Methods 0.000 description 1
• 238000010907 mechanical stirring Methods 0.000 description 1
• 238000013160 medical therapy Methods 0.000 description 1
• 210000004914 menses Anatomy 0.000 description 1
• 230000002175 menstrual effect Effects 0.000 description 1
• OZUAADDJYWWUAD-UHFFFAOYSA-N methyl 3-(benzylamino)-3-oxopropanoate Chemical compound COC(=O)CC(=O)NCC1=CC=CC=C1 OZUAADDJYWWUAD-UHFFFAOYSA-N 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
• 150000004702 methyl esters Chemical class 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 239000011859 microparticle Substances 0.000 description 1
• 230000003228 microsomal effect Effects 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 238000012544 monitoring process Methods 0.000 description 1
• REUFZACIJMPYOK-UHFFFAOYSA-N n-(2-phenylethyl)aniline Chemical compound C=1C=CC=CC=1NCCC1=CC=CC=C1 REUFZACIJMPYOK-UHFFFAOYSA-N 0.000 description 1
• PEUKYEPLCRXPHU-UHFFFAOYSA-N n-(furan-2-ylmethyl)-3,4,5-trimethoxybenzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NCC=2OC=CC=2)=C1 PEUKYEPLCRXPHU-UHFFFAOYSA-N 0.000 description 1
• KQMWYONYWFVEPU-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-1-phenyl-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound FC(F)(F)C1=C(C(=O)NCC=2C=C(Cl)C(Cl)=CC=2)C=NN1C1=CC=CC=C1 KQMWYONYWFVEPU-UHFFFAOYSA-N 0.000 description 1
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
• YESSCAAPLLHWRJ-UHFFFAOYSA-N n-benzyl-1-phenyl-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound FC(F)(F)C1=C(C(=O)NCC=2C=CC=CC=2)C=NN1C1=CC=CC=C1 YESSCAAPLLHWRJ-UHFFFAOYSA-N 0.000 description 1
• BKKTVCDRBAYRCS-UHFFFAOYSA-N n-benzyl-2,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CNCC1=CC=CC=C1 BKKTVCDRBAYRCS-UHFFFAOYSA-N 0.000 description 1
• WCGCLWNPEQTVSG-UHFFFAOYSA-N n-benzylthiophene-2-carboxamide Chemical compound C=1C=CSC=1C(=O)NCC1=CC=CC=C1 WCGCLWNPEQTVSG-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
• VMBFKKOESWAMII-UHFFFAOYSA-N n-butyl-3,4,5-trimethoxybenzamide Chemical compound CCCCNC(=O)C1=CC(OC)=C(OC)C(OC)=C1 VMBFKKOESWAMII-UHFFFAOYSA-N 0.000 description 1
• BAULSHLTGVOYKM-UHFFFAOYSA-N n-butylbenzamide Chemical compound CCCCNC(=O)C1=CC=CC=C1 BAULSHLTGVOYKM-UHFFFAOYSA-N 0.000 description 1
• ANORDWOIBSUYBN-UHFFFAOYSA-N n-chloro-1-phenylmethanamine Chemical compound ClNCC1=CC=CC=C1 ANORDWOIBSUYBN-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
• 239000002105 nanoparticle Substances 0.000 description 1
• 239000006070 nanosuspension Substances 0.000 description 1
• 239000006225 natural substrate Substances 0.000 description 1
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 238000006386 neutralization reaction Methods 0.000 description 1
• 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
• 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
• 231100000344 non-irritating Toxicity 0.000 description 1
• 108091008589 nuclear estrogen receptors Proteins 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 239000004006 olive oil Substances 0.000 description 1
• 235000008390 olive oil Nutrition 0.000 description 1
• 210000000056 organ Anatomy 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 201000008968 osteosarcoma Diseases 0.000 description 1
• 230000002611 ovarian Effects 0.000 description 1
• 230000027758 ovulation cycle Effects 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 230000003076 paracrine Effects 0.000 description 1
• 239000012188 paraffin wax Substances 0.000 description 1
• 239000002245 particle Substances 0.000 description 1
• 239000006072 paste Substances 0.000 description 1
• 230000008506 pathogenesis Effects 0.000 description 1
• 230000001575 pathological effect Effects 0.000 description 1
• 230000007310 pathophysiology Effects 0.000 description 1
• 230000037361 pathway Effects 0.000 description 1
• 239000000312 peanut oil Substances 0.000 description 1
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
• 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
• 125000005981 pentynyl group Chemical group 0.000 description 1
• 230000002093 peripheral effect Effects 0.000 description 1
• 210000003200 peritoneal cavity Anatomy 0.000 description 1
• 239000000825 pharmaceutical preparation Substances 0.000 description 1
• 239000012071 phase Substances 0.000 description 1
• 229940117803 phenethylamine Drugs 0.000 description 1
• 150000002989 phenols Chemical class 0.000 description 1
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• 150000003009 phosphonic acids Chemical class 0.000 description 1
• 230000004962 physiological condition Effects 0.000 description 1
• 239000003075 phytoestrogen Substances 0.000 description 1
• 150000003053 piperidines Chemical class 0.000 description 1
• 208000030761 polycystic kidney disease Diseases 0.000 description 1
• 229920001296 polysiloxane Polymers 0.000 description 1
• 239000013641 positive control Substances 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• 150000003138 primary alcohols Chemical class 0.000 description 1
• 230000008569 process Effects 0.000 description 1
• 239000000583 progesterone congener Substances 0.000 description 1
• 108090000468 progesterone receptors Proteins 0.000 description 1
• 229940095055 progestogen systemic hormonal contraceptives Drugs 0.000 description 1
• 230000005522 programmed cell death Effects 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• 238000000159 protein binding assay Methods 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 230000002685 pulmonary effect Effects 0.000 description 1
• 230000000541 pulsatile effect Effects 0.000 description 1
• RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 description 1
• 150000003235 pyrrolidines Chemical class 0.000 description 1
• 125000001453 quaternary ammonium group Chemical group 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 230000035484 reaction time Effects 0.000 description 1
• 239000002464 receptor antagonist Substances 0.000 description 1
• 229940044551 receptor antagonist Drugs 0.000 description 1
• 230000030541 receptor transactivation Effects 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 210000000664 rectum Anatomy 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 238000012552 review Methods 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 230000007017 scission Effects 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 230000035945 sensitivity Effects 0.000 description 1
• 210000002966 serum Anatomy 0.000 description 1
• 239000008159 sesame oil Substances 0.000 description 1
• 235000011803 sesame oil Nutrition 0.000 description 1
• 238000010898 silica gel chromatography Methods 0.000 description 1
• 229920002379 silicone rubber Polymers 0.000 description 1
• 239000004945 silicone rubber Substances 0.000 description 1
• 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• 229940054269 sodium pyruvate Drugs 0.000 description 1
• 239000007962 solid dispersion Substances 0.000 description 1
• 239000007790 solid phase Substances 0.000 description 1
• 239000008137 solubility enhancer Substances 0.000 description 1
• 239000003549 soybean oil Substances 0.000 description 1
• 235000012424 soybean oil Nutrition 0.000 description 1
• 230000009870 specific binding Effects 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 238000011272 standard treatment Methods 0.000 description 1
• 102000005969 steroid hormone receptors Human genes 0.000 description 1
• 101150035983 str1 gene Proteins 0.000 description 1
• 235000000346 sugar Nutrition 0.000 description 1
• 150000008163 sugars Chemical class 0.000 description 1
• 150000003460 sulfonic acids Chemical class 0.000 description 1
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 238000013268 sustained release Methods 0.000 description 1
• 239000012730 sustained-release form Substances 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 238000010189 synthetic method Methods 0.000 description 1
• 229920001059 synthetic polymer Polymers 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 230000009885 systemic effect Effects 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 230000002381 testicular Effects 0.000 description 1
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
• WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
• GRGKQINPJUNCDI-UHFFFAOYSA-N thieno[2,3-d]pyrimidine-2-carbaldehyde Chemical compound N1=C(N=CC2=C1SC=C2)C=O GRGKQINPJUNCDI-UHFFFAOYSA-N 0.000 description 1
• BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
• 238000013518 transcription Methods 0.000 description 1
• 230000035897 transcription Effects 0.000 description 1
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
• 229910052722 tritium Inorganic materials 0.000 description 1
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
• 238000011144 upstream manufacturing Methods 0.000 description 1
• 210000001215 vagina Anatomy 0.000 description 1
• 239000006213 vaginal ring Substances 0.000 description 1
• 239000003981 vehicle Substances 0.000 description 1
• 239000000341 volatile oil Substances 0.000 description 1