DE69712425T2

DE69712425T2 - Naphthalin-Derivate, Zwischenprodukte und Verwendungen

Naphthalin-Derivate, Zwischenprodukte und Verwendungen

Info

Publication number: DE69712425T2
Authority: DE; Germany
Prior art keywords: formula; phenyl; compound; ethoxy; piperidinyl
Prior art date: 1996-08-29
Legal status : Expired - Fee Related

Application number

DE69712425T

Other languages

German (de)

English (en)

Other versions

DE69712425D1 (de

Inventor

Henry Uhlman Bryant

Thomas Alan Crowell

Charles David Jones

Current Assignee

Eli Lilly and Co

Original Assignee

Eli Lilly and Co

Priority date

1996-08-29

Filing date

1997-08-27

Publication date

2002-10-31

1997-08-27 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

2002-06-13 Application granted granted Critical

2002-06-13 Publication of DE69712425D1 publication Critical patent/DE69712425D1/de

2002-10-31 Publication of DE69712425T2 publication Critical patent/DE69712425T2/de

2017-08-28 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000543 intermediate Substances 0.000 title description 12
150000002790 naphthalenes Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 175
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 88
-1 methyl-1-pyrrolidinyl Chemical group 0.000 claims description 49
239000000262 estrogen Substances 0.000 claims description 33
229940011871 estrogen Drugs 0.000 claims description 31
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 18
208000024891 symptom Diseases 0.000 claims description 17
125000006239 protecting group Chemical group 0.000 claims description 14
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
239000004480 active ingredient Substances 0.000 claims description 13
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
206010028980 Neoplasm Diseases 0.000 claims description 11
RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class 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 claims description 11
239000000583 progesterone congener Substances 0.000 claims description 11
206010027304 Menopausal symptoms Diseases 0.000 claims description 10
208000001132 Osteoporosis Diseases 0.000 claims description 10
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
208000024172 Cardiovascular disease Diseases 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
208000031226 Hyperlipidaemia Diseases 0.000 claims description 6
230000001575 pathological effect Effects 0.000 claims description 6
239000012453 solvate Substances 0.000 claims description 6
230000001419 dependent effect Effects 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 4
206010006187 Breast cancer Diseases 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 4
201000011510 cancer Diseases 0.000 claims description 4
XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 claims description 4
208000037803 restenosis Diseases 0.000 claims description 4
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
208000026310 Breast neoplasm Diseases 0.000 claims description 3
201000009273 Endometriosis Diseases 0.000 claims description 3
210000003433 aortic smooth muscle cell Anatomy 0.000 claims description 3
230000004663 cell proliferation Effects 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
208000002495 Uterine Neoplasms Diseases 0.000 claims description 2
206010046798 Uterine leiomyoma Diseases 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
210000000481 breast Anatomy 0.000 claims description 2
201000010260 leiomyoma Diseases 0.000 claims description 2
206010046766 uterine cancer Diseases 0.000 claims description 2
208000010579 uterine corpus leiomyoma Diseases 0.000 claims description 2
201000007954 uterine fibroid Diseases 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 2
125000005103 alkyl silyl group Chemical group 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 84
238000006243 chemical reaction Methods 0.000 description 59
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
239000000203 mixture Substances 0.000 description 32
239000000243 solution Substances 0.000 description 31
125000003870 2-(1-piperidinyl)ethoxy group Chemical group [*]OC([H])([H])C([H])([H])N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 29
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 29
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
238000000034 method Methods 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
238000002360 preparation method Methods 0.000 description 22
239000002904 solvent Substances 0.000 description 22
238000009472 formulation Methods 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000002253 acid Substances 0.000 description 18
239000000047 product Substances 0.000 description 18
238000011282 treatment Methods 0.000 description 16
238000004458 analytical method Methods 0.000 description 14
235000019439 ethyl acetate Nutrition 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
230000015572 biosynthetic process Effects 0.000 description 13
239000003921 oil Substances 0.000 description 13
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
239000003795 chemical substances by application Substances 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
210000004027 cell Anatomy 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 10
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
229910000041 hydrogen chloride Inorganic materials 0.000 description 10
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 10
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 10
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 9
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
210000000988 bone and bone Anatomy 0.000 description 9
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 9
239000012442 inert solvent Substances 0.000 description 9
BFPYWIDHMRZLRN-UHFFFAOYSA-N 17alpha-ethynyl estradiol Natural products OC1=CC=C2C3CCC(C)(C(CC4)(O)C#C)C4C3CCC2=C1 BFPYWIDHMRZLRN-UHFFFAOYSA-N 0.000 description 8
238000005160 1H NMR spectroscopy Methods 0.000 description 8
239000003153 chemical reaction reagent Substances 0.000 description 8
238000003379 elimination reaction Methods 0.000 description 8
229960002568 ethinylestradiol Drugs 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
238000005481 NMR spectroscopy Methods 0.000 description 7
150000008064 anhydrides Chemical class 0.000 description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
239000012267 brine Substances 0.000 description 7
150000002632 lipids Chemical class 0.000 description 7
239000012299 nitrogen atmosphere Substances 0.000 description 7
210000002966 serum Anatomy 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
239000003826 tablet Substances 0.000 description 7
210000004291 uterus Anatomy 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
229910019142 PO4 Inorganic materials 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
239000002585 base Substances 0.000 description 6
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
201000010099 disease Diseases 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000012458 free base Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 6
239000010452 phosphate Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
238000002560 therapeutic procedure Methods 0.000 description 6
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
241000124008 Mammalia Species 0.000 description 5
239000012359 Methanesulfonyl chloride Substances 0.000 description 5
BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
239000001768 carboxy methyl cellulose Substances 0.000 description 5
230000017858 demethylation Effects 0.000 description 5
238000010520 demethylation reaction Methods 0.000 description 5
238000009164 estrogen replacement therapy Methods 0.000 description 5
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
230000008569 process Effects 0.000 description 5
239000002516 radical scavenger Substances 0.000 description 5
230000009467 reduction Effects 0.000 description 5
230000002829 reductive effect Effects 0.000 description 5
239000007858 starting material Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
108091003079 Bovine Serum Albumin Proteins 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
239000007818 Grignard reagent Substances 0.000 description 4
206010030247 Oestrogen deficiency Diseases 0.000 description 4
102000003982 Parathyroid hormone Human genes 0.000 description 4
108090000445 Parathyroid hormone Proteins 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 4
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
239000012043 crude product Substances 0.000 description 4
230000008030 elimination Effects 0.000 description 4
230000001076 estrogenic effect Effects 0.000 description 4
239000012091 fetal bovine serum Substances 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
239000002609 medium Substances 0.000 description 4
230000009245 menopause Effects 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000000199 parathyroid hormone Substances 0.000 description 4
238000006366 phosphorylation reaction Methods 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
239000000843 powder Substances 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
150000003333 secondary alcohols Chemical class 0.000 description 4
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 4
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000000725 suspension Substances 0.000 description 4
DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 3
KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical class C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
VFLQQZCRHPIGJU-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine;hydron;chloride Chemical compound Cl.ClCCN1CCCCC1 VFLQQZCRHPIGJU-UHFFFAOYSA-N 0.000 description 3
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
229910015845 BBr3 Inorganic materials 0.000 description 3
229940122361 Bisphosphonate Drugs 0.000 description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
239000007832 Na2SO4 Substances 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
ZJAMMHNGLLKZRM-UHFFFAOYSA-N [6-methoxy-2-(3-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=2C=C(OC)C=CC=2)CCC2=CC(OC)=CC=C12 ZJAMMHNGLLKZRM-UHFFFAOYSA-N 0.000 description 3
LOBCWWFINVHKJN-UHFFFAOYSA-N [6-methoxy-2-(3-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound COC1=CC=CC(C=2CCC3=CC(OC)=CC=C3C=2C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)=C1 LOBCWWFINVHKJN-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000000556 agonist Substances 0.000 description 3
239000003513 alkali Substances 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
239000012911 assay medium Substances 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
239000000969 carrier Substances 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
238000006356 dehydrogenation reaction Methods 0.000 description 3
239000003814 drug Substances 0.000 description 3
210000003979 eosinophil Anatomy 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000010410 layer Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
FKUUDDGRDRPAQQ-UHFFFAOYSA-M magnesium;methoxybenzene;bromide Chemical compound [Mg+2].[Br-].COC1=CC=C[C-]=C1 FKUUDDGRDRPAQQ-UHFFFAOYSA-M 0.000 description 3
238000012423 maintenance Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229940053934 norethindrone Drugs 0.000 description 3
VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 3
230000000269 nucleophilic effect Effects 0.000 description 3
229960001319 parathyroid hormone Drugs 0.000 description 3
230000007170 pathology Effects 0.000 description 3
239000001267 polyvinylpyrrolidone Substances 0.000 description 3
229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
208000001685 postmenopausal osteoporosis Diseases 0.000 description 3
239000000376 reactant Substances 0.000 description 3
230000004044 response Effects 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000829 suppository Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
DKLBIQFPQRSEQG-UHFFFAOYSA-N (4-hydroxyphenyl)-[6-methoxy-2-(3-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]methanone Chemical compound COC1=CC=CC(C=2CCC3=CC(OC)=CC=C3C=2C(=O)C=2C=CC(O)=CC=2)=C1 DKLBIQFPQRSEQG-UHFFFAOYSA-N 0.000 description 2
OBOBUDMMFXRNDO-UHFFFAOYSA-N 1-(3-chloropropyl)piperidine;hydron;chloride Chemical compound Cl.ClCCCN1CCCCC1 OBOBUDMMFXRNDO-UHFFFAOYSA-N 0.000 description 2
FBPKIDYMDOOHNS-UHFFFAOYSA-N 1-[2-[4-[[2-(3,4-dimethoxyphenyl)-6-methoxynaphthalen-1-yl]methyl]phenoxy]ethyl]piperidine Chemical compound C=1C=C(OC)C(OC)=CC=1C=1C=CC2=CC(OC)=CC=C2C=1CC(C=C1)=CC=C1OCCN1CCCCC1 FBPKIDYMDOOHNS-UHFFFAOYSA-N 0.000 description 2
XEMFCGQJUPENPR-UHFFFAOYSA-N 1-[2-[4-[[6-methoxy-2-(3-methoxyphenyl)naphthalen-1-yl]methyl]phenoxy]ethyl]piperidine;hydrochloride Chemical compound Cl.COC1=CC=CC(C=2C(=C3C=CC(OC)=CC3=CC=2)CC=2C=CC(OCCN3CCCCC3)=CC=2)=C1 XEMFCGQJUPENPR-UHFFFAOYSA-N 0.000 description 2
XWPPFVHIBBPUCT-UHFFFAOYSA-N 1-[3-[4-[[2-(3-fluoro-4-methoxyphenyl)-6-methoxynaphthalen-1-yl]methyl]phenoxy]propyl]piperidine Chemical compound C=1C=C(OC)C(F)=CC=1C=1C=CC2=CC(OC)=CC=C2C=1CC(C=C1)=CC=C1OCCCN1CCCCC1 XWPPFVHIBBPUCT-UHFFFAOYSA-N 0.000 description 2
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
KCKZIWSINLBROE-UHFFFAOYSA-N 3,4-dihydro-1h-naphthalen-2-one Chemical class C1=CC=C2CC(=O)CCC2=C1 KCKZIWSINLBROE-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
IMTAODPOJFXBCD-UHFFFAOYSA-N 6-(3-methoxyphenyl)-5-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]naphthalen-2-ol Chemical compound COC1=CC=CC(C=2C(=C3C=CC(O)=CC3=CC=2)CC=2C=CC(OCCN3CCCCC3)=CC=2)=C1 IMTAODPOJFXBCD-UHFFFAOYSA-N 0.000 description 2
OGSPWJRAVKPPFI-UHFFFAOYSA-N Alendronic Acid Chemical compound NCCCC(O)(P(O)(O)=O)P(O)(O)=O OGSPWJRAVKPPFI-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
229910015844 BCl3 Inorganic materials 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
208000006386 Bone Resorption Diseases 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
239000007995 HEPES buffer Substances 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
229910010084 LiAlH4 Inorganic materials 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-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
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
CMMRDFPKYZDLGI-UHFFFAOYSA-N [6-hydroxy-2-(3-hydroxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound OC1=CC=CC(C=2CCC3=CC(O)=CC=C3C=2C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)=C1 CMMRDFPKYZDLGI-UHFFFAOYSA-N 0.000 description 2
YVNCHXSEUNTQBQ-UHFFFAOYSA-N [6-methoxy-2-(3-methoxyphenyl)naphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanol Chemical compound COC1=CC=CC(C=2C(=C3C=CC(OC)=CC3=CC=2)C(O)C=2C=CC(OCCN3CCCCC3)=CC=2)=C1 YVNCHXSEUNTQBQ-UHFFFAOYSA-N 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
229940046836 anti-estrogen Drugs 0.000 description 2
230000001833 anti-estrogenic effect Effects 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
230000024279 bone resorption Effects 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
229910000024 caesium carbonate Inorganic materials 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
235000010216 calcium carbonate Nutrition 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
235000012000 cholesterol Nutrition 0.000 description 2
229910052681 coesite Inorganic materials 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000003246 corticosteroid Substances 0.000 description 2
229960001334 corticosteroids Drugs 0.000 description 2
DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 2
229910052906 cristobalite Inorganic materials 0.000 description 2
230000020335 dealkylation Effects 0.000 description 2
238000006900 dealkylation reaction Methods 0.000 description 2
230000002950 deficient Effects 0.000 description 2
239000012649 demethylating agent Substances 0.000 description 2
230000001335 demethylating effect Effects 0.000 description 2
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000328 estrogen antagonist Substances 0.000 description 2
JKKFKPJIXZFSSB-CBZIJGRNSA-N estrone 3-sulfate Chemical compound OS(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 JKKFKPJIXZFSSB-CBZIJGRNSA-N 0.000 description 2
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000019634 flavors Nutrition 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
150000004795 grignard reagents Chemical class 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
230000008595 infiltration Effects 0.000 description 2
238000001764 infiltration Methods 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
230000000670 limiting effect Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
238000005259 measurement Methods 0.000 description 2
230000003821 menstrual periods Effects 0.000 description 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
230000026731 phosphorylation Effects 0.000 description 2
239000000902 placebo Substances 0.000 description 2
229940068196 placebo Drugs 0.000 description 2
235000015320 potassium carbonate Nutrition 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
229940063238 premarin Drugs 0.000 description 2
230000002265 prevention Effects 0.000 description 2
238000000746 purification Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000011552 rat model Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate 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
238000010561 standard procedure Methods 0.000 description 2
230000004936 stimulating effect Effects 0.000 description 2
230000000638 stimulation Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
229910052682 stishovite Inorganic materials 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000000758 substrate Substances 0.000 description 2
229960001603 tamoxifen Drugs 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 2
229910052905 tridymite Inorganic materials 0.000 description 2
PROQIPRRNZUXQM-UHFFFAOYSA-N (16alpha,17betaOH)-Estra-1,3,5(10)-triene-3,16,17-triol Natural products OC1=CC=C2C3CCC(C)(C(C(O)C4)O)C4C3CCC2=C1 PROQIPRRNZUXQM-UHFFFAOYSA-N 0.000 description 1
WZSYSTXLQVXIFG-UHFFFAOYSA-N (4-hydroxyphenyl)-[2-(3-methoxy-4-methylphenyl)-3,4-dihydronaphthalen-1-yl]methanone Chemical compound C1=C(C)C(OC)=CC(C=2CCC3=CC=CC=C3C=2C(=O)C=2C=CC(O)=CC=2)=C1 WZSYSTXLQVXIFG-UHFFFAOYSA-N 0.000 description 1
HJEVRUPXUJPSQO-UHFFFAOYSA-N (4-hydroxyphenyl)-[6-methoxy-2-(3-methoxyphenyl)naphthalen-1-yl]methanone Chemical compound COC1=CC=CC(C=2C(=C3C=CC(OC)=CC3=CC=2)C(=O)C=2C=CC(O)=CC=2)=C1 HJEVRUPXUJPSQO-UHFFFAOYSA-N 0.000 description 1
NBQRSESGSXQGOL-UHFFFAOYSA-N (4-hydroxyphenyl)-[6-methoxy-2-(5-methoxy-6,6-dimethylcyclohexa-2,4-dien-1-yl)-3,4-dihydronaphthalen-1-yl]methanone Chemical compound CC1(C)C(OC)=CC=CC1C(CCC1=CC(OC)=CC=C11)=C1C(=O)C1=CC=C(O)C=C1 NBQRSESGSXQGOL-UHFFFAOYSA-N 0.000 description 1
QRPUVEAHEMVOOG-UHFFFAOYSA-O (4-hydroxyphenyl)methanone Chemical compound OC1=CC=C([C+]=O)C=C1 QRPUVEAHEMVOOG-UHFFFAOYSA-O 0.000 description 1
MRNBRPRICFKSAQ-UHFFFAOYSA-N (4-methoxyphenyl)-[2-(3-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=2C=C(OC)C=CC=2)CCC2=CC=CC=C12 MRNBRPRICFKSAQ-UHFFFAOYSA-N 0.000 description 1
FDGCNGPUZIIRQI-UHFFFAOYSA-N (4-methoxyphenyl)methanone Chemical compound O(C1=CC=C([C-]=O)C=C1)C FDGCNGPUZIIRQI-UHFFFAOYSA-N 0.000 description 1
UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
PTIMCMKSBMGYGJ-UHFFFAOYSA-N 1-(2-chloroethyl)-3,3-dimethylpyrrolidine;hydrochloride Chemical compound Cl.CC1(C)CCN(CCCl)C1 PTIMCMKSBMGYGJ-UHFFFAOYSA-N 0.000 description 1
NVNJVLADICADBL-UHFFFAOYSA-N 1-(2-chloroethyl)-3-methylpyrrolidine;hydrochloride Chemical compound Cl.CC1CCN(CCCl)C1 NVNJVLADICADBL-UHFFFAOYSA-N 0.000 description 1
WNRWEBKEQARBKV-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine Chemical compound ClCCN1CCCCC1 WNRWEBKEQARBKV-UHFFFAOYSA-N 0.000 description 1
FSNGFFWICFYWQC-UHFFFAOYSA-N 1-(2-chloroethyl)pyrrolidine;hydron;chloride Chemical compound Cl.ClCCN1CCCC1 FSNGFFWICFYWQC-UHFFFAOYSA-N 0.000 description 1
MMZAYRBXBZQPEP-UHFFFAOYSA-N 1-(3-chloropropyl)-2-methylpyrrolidine;hydrochloride Chemical compound Cl.CC1CCCN1CCCCl MMZAYRBXBZQPEP-UHFFFAOYSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
IQFYYKKMVGJFEH-OFKYTIFKSA-N 1-[(2r,4s,5r)-4-hydroxy-5-(tritiooxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound C1[C@H](O)[C@@H](CO[3H])O[C@H]1N1C(=O)NC(=O)C(C)=C1 IQFYYKKMVGJFEH-OFKYTIFKSA-N 0.000 description 1
HUBDJUHAFGYZNJ-UHFFFAOYSA-N 1-[2-[4-[[2-(2,3-dimethoxyphenyl)naphthalen-1-yl]methyl]phenoxy]ethyl]piperidine Chemical compound COC1=CC=CC(C=2C(=C3C=CC=CC3=CC=2)CC=2C=CC(OCCN3CCCCC3)=CC=2)=C1OC HUBDJUHAFGYZNJ-UHFFFAOYSA-N 0.000 description 1
JGYGZPCTVFXVFU-UHFFFAOYSA-N 1-[2-[4-[[2-(2,4-dimethoxyphenyl)-6-methoxynaphthalen-1-yl]methyl]phenoxy]ethyl]piperidine Chemical compound COC1=CC(OC)=CC=C1C1=CC=C(C=C(OC)C=C2)C2=C1CC(C=C1)=CC=C1OCCN1CCCCC1 JGYGZPCTVFXVFU-UHFFFAOYSA-N 0.000 description 1
BNYUQGMOGHOAMV-UHFFFAOYSA-N 1-[2-[4-[[2-(2-ethyl-3-methoxyphenyl)-6-methoxynaphthalen-1-yl]methyl]phenoxy]ethyl]piperidine Chemical compound CCC1=C(OC)C=CC=C1C1=CC=C(C=C(OC)C=C2)C2=C1CC(C=C1)=CC=C1OCCN1CCCCC1 BNYUQGMOGHOAMV-UHFFFAOYSA-N 0.000 description 1
AGLLAQSIPGRXIP-UHFFFAOYSA-N 1-[2-[4-[[2-(2-methoxyphenyl)naphthalen-1-yl]methyl]phenoxy]ethyl]piperidine Chemical compound COC1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1CC(C=C1)=CC=C1OCCN1CCCCC1 AGLLAQSIPGRXIP-UHFFFAOYSA-N 0.000 description 1
NGFNEIHRQRIKOZ-UHFFFAOYSA-N 1-[2-[4-[[2-(3,4-dimethoxyphenyl)naphthalen-1-yl]methyl]phenoxy]ethyl]pyrrolidine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(C=CC=C2)C2=C1CC(C=C1)=CC=C1OCCN1CCCC1 NGFNEIHRQRIKOZ-UHFFFAOYSA-N 0.000 description 1
LZVQBXVDOVRWJZ-UHFFFAOYSA-N 1-[2-[4-[[2-(3-chloro-4-fluoro-2-methoxyphenyl)-6-methoxynaphthalen-1-yl]methyl]phenoxy]ethyl]piperidine Chemical compound C=1C=C(F)C(Cl)=C(OC)C=1C=1C=CC2=CC(OC)=CC=C2C=1CC(C=C1)=CC=C1OCCN1CCCCC1 LZVQBXVDOVRWJZ-UHFFFAOYSA-N 0.000 description 1
WFOHMMNAEAXLOX-UHFFFAOYSA-N 1-[2-[4-[[2-(3-chlorophenyl)-6-methoxynaphthalen-1-yl]methyl]phenoxy]ethyl]pyrrolidine Chemical compound C=1C=CC(Cl)=CC=1C=1C=CC2=CC(OC)=CC=C2C=1CC(C=C1)=CC=C1OCCN1CCCC1 WFOHMMNAEAXLOX-UHFFFAOYSA-N 0.000 description 1
IJDHLOIUTAKUHB-UHFFFAOYSA-N 1-[2-[4-[[2-(3-ethyl-2-methylphenyl)-6-methoxynaphthalen-1-yl]methyl]phenoxy]ethyl]piperidine Chemical compound CCC1=CC=CC(C=2C(=C3C=CC(OC)=CC3=CC=2)CC=2C=CC(OCCN3CCCCC3)=CC=2)=C1C IJDHLOIUTAKUHB-UHFFFAOYSA-N 0.000 description 1
RAMZJIZPBMJGCP-UHFFFAOYSA-N 1-[2-[4-[[2-(3-ethyl-4-methoxyphenyl)-6-methoxynaphthalen-1-yl]methyl]phenoxy]ethyl]piperidine Chemical compound C1=C(OC)C(CC)=CC(C=2C(=C3C=CC(OC)=CC3=CC=2)CC=2C=CC(OCCN3CCCCC3)=CC=2)=C1 RAMZJIZPBMJGCP-UHFFFAOYSA-N 0.000 description 1
LZSYFCHIKPWAMY-UHFFFAOYSA-N 1-[2-[4-[[2-(4-chloro-2-ethylphenyl)-6-methoxynaphthalen-1-yl]methyl]phenoxy]ethyl]piperidine Chemical compound CCC1=CC(Cl)=CC=C1C1=CC=C(C=C(OC)C=C2)C2=C1CC(C=C1)=CC=C1OCCN1CCCCC1 LZSYFCHIKPWAMY-UHFFFAOYSA-N 0.000 description 1
GNZARHWOZNOUSZ-UHFFFAOYSA-N 1-[2-[4-[[2-(4-chloro-3-methoxyphenyl)-6-methoxynaphthalen-1-yl]methyl]phenoxy]ethyl]pyrrolidine Chemical compound C=1C=C(Cl)C(OC)=CC=1C=1C=CC2=CC(OC)=CC=C2C=1CC(C=C1)=CC=C1OCCN1CCCC1 GNZARHWOZNOUSZ-UHFFFAOYSA-N 0.000 description 1
GANLLQNDFXEPMF-UHFFFAOYSA-N 1-[2-[4-[[2-(4-fluoro-3-methoxy-2-methylphenyl)-6-methoxynaphthalen-1-yl]methyl]phenoxy]ethyl]piperidine Chemical compound C=1C=C(F)C(OC)=C(C)C=1C=1C=CC2=CC(OC)=CC=C2C=1CC(C=C1)=CC=C1OCCN1CCCCC1 GANLLQNDFXEPMF-UHFFFAOYSA-N 0.000 description 1
AYKTYTVEBQBYPQ-UHFFFAOYSA-N 1-[2-[4-[[2-(4-fluoro-3-methoxyphenyl)-6-methoxynaphthalen-1-yl]methyl]phenoxy]ethyl]piperidine Chemical compound C=1C=C(F)C(OC)=CC=1C=1C=CC2=CC(OC)=CC=C2C=1CC(C=C1)=CC=C1OCCN1CCCCC1 AYKTYTVEBQBYPQ-UHFFFAOYSA-N 0.000 description 1
GUQXQRJHGOXVEZ-UHFFFAOYSA-N 1-[2-[4-[[2-(4-methoxy-2-methylphenyl)naphthalen-1-yl]methyl]phenoxy]ethyl]pyrrolidine Chemical compound CC1=CC(OC)=CC=C1C1=CC=C(C=CC=C2)C2=C1CC(C=C1)=CC=C1OCCN1CCCC1 GUQXQRJHGOXVEZ-UHFFFAOYSA-N 0.000 description 1
VOLUAQNUUIENKL-UHFFFAOYSA-N 1-[2-[4-[[6-methoxy-2-(2-methoxyphenyl)naphthalen-1-yl]methyl]phenoxy]ethyl]piperidine Chemical compound C=1C=CC=C(OC)C=1C=1C=CC2=CC(OC)=CC=C2C=1CC(C=C1)=CC=C1OCCN1CCCCC1 VOLUAQNUUIENKL-UHFFFAOYSA-N 0.000 description 1
RJAXQEDSJVNTQS-UHFFFAOYSA-N 1-[2-[4-[[6-methoxy-2-(3-methoxyphenyl)naphthalen-1-yl]methyl]phenoxy]ethyl]piperidine Chemical compound COC1=CC=CC(C=2C(=C3C=CC(OC)=CC3=CC=2)CC=2C=CC(OCCN3CCCCC3)=CC=2)=C1 RJAXQEDSJVNTQS-UHFFFAOYSA-N 0.000 description 1
KNBCRLOUKMZTQN-UHFFFAOYSA-N 1-[3-[4-[[2-(2-ethyl-3-methoxyphenyl)-6-methoxynaphthalen-1-yl]methyl]phenoxy]propyl]piperidine Chemical compound CCC1=C(OC)C=CC=C1C1=CC=C(C=C(OC)C=C2)C2=C1CC(C=C1)=CC=C1OCCCN1CCCCC1 KNBCRLOUKMZTQN-UHFFFAOYSA-N 0.000 description 1
QWUOYJGYLJLAGE-UHFFFAOYSA-N 1-[3-[4-[[6-methoxy-2-(3-methoxy-2-methylphenyl)naphthalen-1-yl]methyl]phenoxy]propyl]piperidine Chemical compound C=1C=CC(OC)=C(C)C=1C=1C=CC2=CC(OC)=CC=C2C=1CC(C=C1)=CC=C1OCCCN1CCCCC1 QWUOYJGYLJLAGE-UHFFFAOYSA-N 0.000 description 1
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
SPXOTSHWBDUUMT-UHFFFAOYSA-N 138-42-1 Chemical compound OS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-N 0.000 description 1
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 1
HCSBTDBGTNZOAB-UHFFFAOYSA-N 2,3-dinitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O HCSBTDBGTNZOAB-UHFFFAOYSA-N 0.000 description 1
XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-UHFFFAOYSA-N 2-(hydroxymethyl)-6-[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol Chemical compound OCC1OC(OC2C(O)C(O)C(O)OC2CO)C(O)C(O)C1O GUBGYTABKSRVRQ-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
DZELFJDPEKCFSD-UHFFFAOYSA-N 2-[1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]naphthalen-2-yl]phenol Chemical compound OC1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1CC(C=C1)=CC=C1OCCN1CCCCC1 DZELFJDPEKCFSD-UHFFFAOYSA-N 0.000 description 1
LEDHQIGNLVGNBR-UHFFFAOYSA-N 2-[4-[[2-(3-chloro-2-methoxyphenyl)-6-methoxynaphthalen-1-yl]methyl]phenoxy]-n,n-dimethylethanamine Chemical compound C=1C=CC(Cl)=C(OC)C=1C=1C=CC2=CC(OC)=CC=C2C=1CC1=CC=C(OCCN(C)C)C=C1 LEDHQIGNLVGNBR-UHFFFAOYSA-N 0.000 description 1
JSBXRGRSLWYGOL-UHFFFAOYSA-N 2-[4-[[6-methoxy-2-(3-methoxyphenyl)naphthalen-1-yl]methyl]phenoxy]-n,n-dimethylethanamine Chemical compound COC1=CC=CC(C=2C(=C3C=CC(OC)=CC3=CC=2)CC=2C=CC(OCCN(C)C)=CC=2)=C1 JSBXRGRSLWYGOL-UHFFFAOYSA-N 0.000 description 1
MNURPFVONZPVLA-UHFFFAOYSA-N 2-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1Cl MNURPFVONZPVLA-UHFFFAOYSA-N 0.000 description 1
LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 description 1
NNFPOQHHJDPRKK-UHFFFAOYSA-N 2-methoxy-5-[1-[[4-(2-pyrrolidin-1-ylethoxy)phenyl]methyl]naphthalen-2-yl]phenol Chemical compound C1=C(O)C(OC)=CC=C1C1=CC=C(C=CC=C2)C2=C1CC(C=C1)=CC=C1OCCN1CCCC1 NNFPOQHHJDPRKK-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
HMGCGUWFPZVPEK-UHFFFAOYSA-N 2-naphthalen-2-ylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1 HMGCGUWFPZVPEK-UHFFFAOYSA-N 0.000 description 1
CGGABFBZAKYKKT-UHFFFAOYSA-N 3-[1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]naphthalen-2-yl]phenol Chemical compound OC1=CC=CC(C=2C(=C3C=CC=CC3=CC=2)CC=2C=CC(OCCN3CCCCC3)=CC=2)=C1 CGGABFBZAKYKKT-UHFFFAOYSA-N 0.000 description 1
WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 1
XCTJVXJYNQOEMJ-UHFFFAOYSA-N 3-methyl-4-[1-[[4-(2-pyrrolidin-1-ylethoxy)phenyl]methyl]naphthalen-2-yl]phenol Chemical compound CC1=CC(O)=CC=C1C1=CC=C(C=CC=C2)C2=C1CC(C=C1)=CC=C1OCCN1CCCC1 XCTJVXJYNQOEMJ-UHFFFAOYSA-N 0.000 description 1
JNZDYUPZUHCHFK-UHFFFAOYSA-N 3-pyrrolidin-3-ylpyridine Chemical compound C1NCCC1C1=CC=CN=C1 JNZDYUPZUHCHFK-UHFFFAOYSA-N 0.000 description 1
PPHFMOTZOURFDQ-UHFFFAOYSA-N 4-[6-hydroxy-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]naphthalen-2-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1=CC=C(C=C(O)C=C2)C2=C1CC(C=C1)=CC=C1OCCN1CCCCC1 PPHFMOTZOURFDQ-UHFFFAOYSA-N 0.000 description 1
PXACTUVBBMDKRW-UHFFFAOYSA-M 4-bromobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-M 0.000 description 1
PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 description 1
IWYVYUZADLIDEY-UHFFFAOYSA-M 4-methoxybenzenesulfonate Chemical compound COC1=CC=C(S([O-])(=O)=O)C=C1 IWYVYUZADLIDEY-UHFFFAOYSA-M 0.000 description 1
OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 1
RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 1
PENQMBBFZSZRNU-UHFFFAOYSA-N 6-(2-ethyl-3-hydroxyphenyl)-5-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]naphthalen-2-ol Chemical compound CCC1=C(O)C=CC=C1C1=CC=C(C=C(O)C=C2)C2=C1CC(C=C1)=CC=C1OCCN1CCCCC1 PENQMBBFZSZRNU-UHFFFAOYSA-N 0.000 description 1
YONVVHMHNGUANR-UHFFFAOYSA-N 6-(2-ethyl-3-methoxyphenyl)-5-[[4-(3-piperidin-1-ylpropoxy)phenyl]methyl]naphthalen-2-ol Chemical compound CCC1=C(OC)C=CC=C1C1=CC=C(C=C(O)C=C2)C2=C1CC(C=C1)=CC=C1OCCCN1CCCCC1 YONVVHMHNGUANR-UHFFFAOYSA-N 0.000 description 1
YWBJTUSHVUXEPG-UHFFFAOYSA-N 6-(2-ethylphenyl)-5-[[4-(3-piperidin-1-ylpropoxy)phenyl]methyl]naphthalen-2-ol Chemical compound CCC1=CC=CC=C1C1=CC=C(C=C(O)C=C2)C2=C1CC(C=C1)=CC=C1OCCCN1CCCCC1 YWBJTUSHVUXEPG-UHFFFAOYSA-N 0.000 description 1
DJOLQWXBIVYFAN-UHFFFAOYSA-N 6-(2-hydroxyphenyl)-5-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]naphthalen-2-ol Chemical compound C=1C=CC=C(O)C=1C=1C=CC2=CC(O)=CC=C2C=1CC(C=C1)=CC=C1OCCN1CCCCC1 DJOLQWXBIVYFAN-UHFFFAOYSA-N 0.000 description 1
ABWFJTIVJJFYPH-UHFFFAOYSA-N 6-(3-chloro-4-fluoro-2-hydroxyphenyl)-5-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]naphthalen-2-ol Chemical compound C=1C=C(F)C(Cl)=C(O)C=1C=1C=CC2=CC(O)=CC=C2C=1CC(C=C1)=CC=C1OCCN1CCCCC1 ABWFJTIVJJFYPH-UHFFFAOYSA-N 0.000 description 1
CGOLIZCLQPQROP-UHFFFAOYSA-N 6-(3-chlorophenyl)-5-[[4-(2-pyrrolidin-1-ylethoxy)phenyl]methyl]naphthalen-2-ol Chemical compound ClC=1C=C(C=CC=1)C1=C(C2=CC=C(C=C2C=C1)O)CC1=CC=C(C=C1)OCCN1CCCC1 CGOLIZCLQPQROP-UHFFFAOYSA-N 0.000 description 1
WSDKAJXFXDCVME-UHFFFAOYSA-N 6-(3-ethyl-2-methylphenyl)-5-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]naphthalen-2-ol Chemical compound CCC1=CC=CC(C=2C(=C3C=CC(O)=CC3=CC=2)CC=2C=CC(OCCN3CCCCC3)=CC=2)=C1C WSDKAJXFXDCVME-UHFFFAOYSA-N 0.000 description 1
RJUURKYXSFNOEE-UHFFFAOYSA-N 6-(3-fluoro-4-hydroxyphenyl)-5-[[4-(3-piperidin-1-ylpropoxy)phenyl]methyl]naphthalen-2-ol Chemical compound C=1C=C(O)C(F)=CC=1C=1C=CC2=CC(O)=CC=C2C=1CC(C=C1)=CC=C1OCCCN1CCCCC1 RJUURKYXSFNOEE-UHFFFAOYSA-N 0.000 description 1
WVBDKCJUPBSEIG-UHFFFAOYSA-N 6-(3-fluoro-4-methoxyphenyl)-5-[[4-(3-piperidin-1-ylpropoxy)phenyl]methyl]naphthalen-2-ol Chemical compound C1=C(F)C(OC)=CC=C1C1=CC=C(C=C(O)C=C2)C2=C1CC(C=C1)=CC=C1OCCCN1CCCCC1 WVBDKCJUPBSEIG-UHFFFAOYSA-N 0.000 description 1
VIOAZAPFAAGCRX-UHFFFAOYSA-N 6-(3-fluorophenyl)-5-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]naphthalen-2-ol Chemical compound C=1C=CC(F)=CC=1C=1C=CC2=CC(O)=CC=C2C=1CC(C=C1)=CC=C1OCCN1CCCCC1 VIOAZAPFAAGCRX-UHFFFAOYSA-N 0.000 description 1
IFWVXJOMPQWGPK-UHFFFAOYSA-N 6-(3-hydroxy-2-methylphenyl)-5-[[4-(3-piperidin-1-ylpropoxy)phenyl]methyl]naphthalen-2-ol Chemical compound CC1=C(O)C=CC=C1C1=CC=C(C=C(O)C=C2)C2=C1CC(C=C1)=CC=C1OCCCN1CCCCC1 IFWVXJOMPQWGPK-UHFFFAOYSA-N 0.000 description 1
IDDWLLOIUNWLIQ-UHFFFAOYSA-N 6-(3-hydroxy-4-methylphenyl)-5-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]naphthalen-2-ol Chemical compound C1=C(O)C(C)=CC=C1C1=CC=C(C=C(O)C=C2)C2=C1CC(C=C1)=CC=C1OCCN1CCCCC1 IDDWLLOIUNWLIQ-UHFFFAOYSA-N 0.000 description 1
KYSKRDWKKUPONP-UHFFFAOYSA-N 6-(3-hydroxyphenyl)-5-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]naphthalen-2-ol Chemical compound OC1=CC=CC(C=2C(=C3C=CC(O)=CC3=CC=2)CC=2C=CC(OCCN3CCCCC3)=CC=2)=C1 KYSKRDWKKUPONP-UHFFFAOYSA-N 0.000 description 1
NFNCJBNCXDJPSH-UHFFFAOYSA-N 6-(3-hydroxyphenyl)-5-[[4-(2-pyrrolidin-1-ylethoxy)phenyl]methyl]naphthalen-2-ol Chemical compound OC1=CC=CC(C=2C(=C3C=CC(O)=CC3=CC=2)CC=2C=CC(OCCN3CCCC3)=CC=2)=C1 NFNCJBNCXDJPSH-UHFFFAOYSA-N 0.000 description 1
NDJVRCFQCMKBGM-UHFFFAOYSA-N 6-(3-hydroxyphenyl)-5-[[4-(3-piperidin-1-ylpropoxy)phenyl]methyl]naphthalen-2-ol Chemical compound OC1=CC=CC(C=2C(=C3C=CC(O)=CC3=CC=2)CC=2C=CC(OCCCN3CCCCC3)=CC=2)=C1 NDJVRCFQCMKBGM-UHFFFAOYSA-N 0.000 description 1
RQVQVGKOJMUWJP-UHFFFAOYSA-N 6-(3-methoxyphenyl)-5-[[4-(2-pyrrolidin-1-ylethoxy)phenyl]methyl]naphthalen-2-ol Chemical compound COC1=CC=CC(C=2C(=C3C=CC(O)=CC3=CC=2)CC=2C=CC(OCCN3CCCC3)=CC=2)=C1 RQVQVGKOJMUWJP-UHFFFAOYSA-N 0.000 description 1
SSKFWARRRDDWIV-UHFFFAOYSA-N 6-(4-chloro-2-ethylphenyl)-5-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]naphthalen-2-ol Chemical compound CCC1=CC(Cl)=CC=C1C1=CC=C(C=C(O)C=C2)C2=C1CC(C=C1)=CC=C1OCCN1CCCCC1 SSKFWARRRDDWIV-UHFFFAOYSA-N 0.000 description 1
QFBBEROXEUWFLG-UHFFFAOYSA-N 6-(4-fluoro-3-hydroxy-2-methylphenyl)-5-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]naphthalen-2-ol Chemical compound CC1=C(O)C(F)=CC=C1C1=CC=C(C=C(O)C=C2)C2=C1CC(C=C1)=CC=C1OCCN1CCCCC1 QFBBEROXEUWFLG-UHFFFAOYSA-N 0.000 description 1
PMZSMIMURRYLGE-UHFFFAOYSA-N 6-(4-fluoro-3-methoxyphenyl)-5-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]naphthalen-2-ol Chemical compound C1=C(F)C(OC)=CC(C=2C(=C3C=CC(O)=CC3=CC=2)CC=2C=CC(OCCN3CCCCC3)=CC=2)=C1 PMZSMIMURRYLGE-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
208000002874 Acne Vulgaris Diseases 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
102000002260 Alkaline Phosphatase Human genes 0.000 description 1
108020004774 Alkaline Phosphatase Proteins 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
208000004746 Atrophic Vaginitis Diseases 0.000 description 1
206010003693 Atrophic vulvovaginitis Diseases 0.000 description 1
208000010392 Bone Fractures Diseases 0.000 description 1
206010065687 Bone loss Diseases 0.000 description 1
101001011741 Bos taurus Insulin Proteins 0.000 description 1
LEMWWMPRSYVPPV-UHFFFAOYSA-M COc1ccc([Mg]Br)c(Cl)c1 Chemical compound COc1ccc([Mg]Br)c(Cl)c1 LEMWWMPRSYVPPV-UHFFFAOYSA-M 0.000 description 1
DQTRPTVYYLCSJK-UHFFFAOYSA-M COc1cccc([Mg]Br)c1C Chemical compound COc1cccc([Mg]Br)c1C DQTRPTVYYLCSJK-UHFFFAOYSA-M 0.000 description 1
102000055006 Calcitonin Human genes 0.000 description 1
108060001064 Calcitonin Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
ZQZFYGIXNQKOAV-OCEACIFDSA-N Droloxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)\C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-OCEACIFDSA-N 0.000 description 1
206010013908 Dysfunctional uterine bleeding Diseases 0.000 description 1
208000005171 Dysmenorrhea Diseases 0.000 description 1
206010013935 Dysmenorrhoea Diseases 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
108010092408 Eosinophil Peroxidase Proteins 0.000 description 1
102000044708 Eosinophil peroxidases Human genes 0.000 description 1
WKRLQDKEXYKHJB-UHFFFAOYSA-N Equilin Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3=CCC2=C1 WKRLQDKEXYKHJB-UHFFFAOYSA-N 0.000 description 1
UOACKFBJUYNSLK-XRKIENNPSA-N Estradiol Cypionate Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H](C4=CC=C(O)C=C4CC3)CC[C@@]21C)C(=O)CCC1CCCC1 UOACKFBJUYNSLK-XRKIENNPSA-N 0.000 description 1
RSEPBGGWRJCQGY-RBRWEJTLSA-N Estradiol valerate Chemical compound C1CC2=CC(O)=CC=C2[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCC)[C@@]1(C)CC2 RSEPBGGWRJCQGY-RBRWEJTLSA-N 0.000 description 1
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 1
239000004606 Fillers/Extenders Substances 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
241000206672 Gelidium Species 0.000 description 1
239000012981 Hank's balanced salt solution Substances 0.000 description 1
206010020100 Hip fracture Diseases 0.000 description 1
206010020112 Hirsutism Diseases 0.000 description 1
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 1
RWSXRVCMGQZWBV-PHDIDXHHSA-N L-Glutathione Natural products OC(=O)[C@H](N)CCC(=O)N[C@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-PHDIDXHHSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
206010027514 Metrorrhagia Diseases 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 1
QECVIPBZOPUTRD-UHFFFAOYSA-N N=S(=O)=O Chemical class N=S(=O)=O QECVIPBZOPUTRD-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
229910018954 NaNH2 Inorganic materials 0.000 description 1
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
ICTXHFFSOAJUMG-SLHNCBLASA-N Norethynodrel Chemical compound C1CC(=O)CC2=C1[C@H]1CC[C@](C)([C@](CC3)(O)C#C)[C@@H]3[C@@H]1CC2 ICTXHFFSOAJUMG-SLHNCBLASA-N 0.000 description 1
102000004067 Osteocalcin Human genes 0.000 description 1
108090000573 Osteocalcin Proteins 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229910020667 PBr3 Inorganic materials 0.000 description 1
BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
229920000081 Polyestradiol phosphate Polymers 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
206010060862 Prostate cancer Diseases 0.000 description 1
208000000236 Prostatic Neoplasms Diseases 0.000 description 1
LCYXYLLJXMAEMT-SAXRGWBVSA-N Pyridinoline Chemical compound OC(=O)[C@@H](N)CCC1=C[N+](C[C@H](O)CC[C@H](N)C([O-])=O)=CC(O)=C1C[C@H](N)C(O)=O LCYXYLLJXMAEMT-SAXRGWBVSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
DKJJVAGXPKPDRL-UHFFFAOYSA-N Tiludronic acid Chemical compound OP(O)(=O)C(P(O)(O)=O)SC1=CC=C(Cl)C=C1 DKJJVAGXPKPDRL-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
206010067269 Uterine fibrosis Diseases 0.000 description 1
ZZXDRXVIRVJQBT-UHFFFAOYSA-M Xylenesulfonate Chemical compound CC1=CC=CC(S([O-])(=O)=O)=C1C ZZXDRXVIRVJQBT-UHFFFAOYSA-M 0.000 description 1
YVSCLVLTEMGGAM-UHFFFAOYSA-N [2-(2,4-dimethoxyphenyl)-6-methoxy-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanol Chemical compound C=1C=C(OC)C=C(OC)C=1C=1CCC2=CC(OC)=CC=C2C=1C(O)C(C=C1)=CC=C1OCCN1CCCCC1 YVSCLVLTEMGGAM-UHFFFAOYSA-N 0.000 description 1
PSMFBFINPVCTEB-UHFFFAOYSA-N [2-(2-chloro-3-methoxyphenyl)-6-methoxy-3,4-dihydronaphthalen-1-yl]-(4-hydroxyphenyl)methanone Chemical compound C=1C=CC(OC)=C(Cl)C=1C=1CCC2=CC(OC)=CC=C2C=1C(=O)C1=CC=C(O)C=C1 PSMFBFINPVCTEB-UHFFFAOYSA-N 0.000 description 1
MYNRMRIYCXBHPA-UHFFFAOYSA-N [2-(2-chloro-4-fluoro-3-methoxyphenyl)-6-methoxy-3,4-dihydronaphthalen-1-yl]-(4-hydroxyphenyl)methanone Chemical compound C=1C=C(F)C(OC)=C(Cl)C=1C=1CCC2=CC(OC)=CC=C2C=1C(=O)C1=CC=C(O)C=C1 MYNRMRIYCXBHPA-UHFFFAOYSA-N 0.000 description 1
GZIJOOVBTUXSOV-UHFFFAOYSA-N [2-(2-chloro-4-fluorophenyl)-6-methoxy-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanol Chemical compound C=1C=C(F)C=C(Cl)C=1C=1CCC2=CC(OC)=CC=C2C=1C(O)C(C=C1)=CC=C1OCCN1CCCCC1 GZIJOOVBTUXSOV-UHFFFAOYSA-N 0.000 description 1
GCKLIBBJHXVLMA-UHFFFAOYSA-N [2-(2-ethyl-4-methoxyphenyl)-6-methoxy-3,4-dihydronaphthalen-1-yl]-(4-hydroxyphenyl)methanone Chemical compound CCC1=CC(OC)=CC=C1C(CCC1=CC(OC)=CC=C11)=C1C(=O)C1=CC=C(O)C=C1 GCKLIBBJHXVLMA-UHFFFAOYSA-N 0.000 description 1
DYTRPTQBFWOIFO-UHFFFAOYSA-N [2-(2-fluoro-3-hydroxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound OC1=CC=CC(C=2CCC3=CC=CC=C3C=2C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)=C1F DYTRPTQBFWOIFO-UHFFFAOYSA-N 0.000 description 1
PYNNBVMPAUFWCB-UHFFFAOYSA-N [2-(2-methylphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanol Chemical compound CC1=CC=CC=C1C(CCC1=CC=CC=C11)=C1C(O)C(C=C1)=CC=C1OCCN1CCCCC1 PYNNBVMPAUFWCB-UHFFFAOYSA-N 0.000 description 1
WLMDGGOCUJTZCK-UHFFFAOYSA-N [2-(3,4-dihydroxyphenyl)-6-hydroxy-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C=1C=C(O)C(O)=CC=1C=1CCC2=CC(O)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCCC1 WLMDGGOCUJTZCK-UHFFFAOYSA-N 0.000 description 1
DKZSYJFIJQDIPY-UHFFFAOYSA-N [2-(3,4-dimethoxyphenyl)-6-methoxy-3,4-dihydronaphthalen-1-yl]-(4-hydroxyphenyl)methanone Chemical compound C=1C=C(OC)C(OC)=CC=1C=1CCC2=CC(OC)=CC=C2C=1C(=O)C1=CC=C(O)C=C1 DKZSYJFIJQDIPY-UHFFFAOYSA-N 0.000 description 1
KBRMRSUYRWZQNZ-UHFFFAOYSA-N [2-(3,4-dimethoxyphenyl)-6-methoxy-3,4-dihydronaphthalen-1-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=2C=C(OC)C(OC)=CC=2)CCC2=CC(OC)=CC=C12 KBRMRSUYRWZQNZ-UHFFFAOYSA-N 0.000 description 1
XZZGSMZKHBIMJZ-UHFFFAOYSA-N [2-(3,4-dimethoxyphenyl)-6-methoxy-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanol Chemical compound C=1C=C(OC)C(OC)=CC=1C=1CCC2=CC(OC)=CC=C2C=1C(O)C(C=C1)=CC=C1OCCN1CCCCC1 XZZGSMZKHBIMJZ-UHFFFAOYSA-N 0.000 description 1
RUSPYPGSMWYJPQ-UHFFFAOYSA-N [2-(3,4-dimethoxyphenyl)-6-methoxy-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C=1C=C(OC)C(OC)=CC=1C=1CCC2=CC(OC)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCCC1 RUSPYPGSMWYJPQ-UHFFFAOYSA-N 0.000 description 1
RJIYPDVZVNGJRP-UHFFFAOYSA-N [2-(3-chloro-4-methoxyphenyl)-6-methoxy-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C=1C=C(OC)C(Cl)=CC=1C=1CCC2=CC(OC)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCCC1 RJIYPDVZVNGJRP-UHFFFAOYSA-N 0.000 description 1
YTEKICYDMGDSHI-UHFFFAOYSA-N [2-(3-chlorophenyl)-6-methoxy-3,4-dihydronaphthalen-1-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=2C=C(Cl)C=CC=2)CCC2=CC(OC)=CC=C12 YTEKICYDMGDSHI-UHFFFAOYSA-N 0.000 description 1
IWUHQNPKBMWCAY-UHFFFAOYSA-N [2-(3-fluoro-2-methoxyphenyl)-6-methoxy-3,4-dihydronaphthalen-1-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=2C(=C(F)C=CC=2)OC)CCC2=CC(OC)=CC=C12 IWUHQNPKBMWCAY-UHFFFAOYSA-N 0.000 description 1
YIWBWKKNKYGJNR-UHFFFAOYSA-N [2-(3-hydroxyphenyl)-6-methoxy-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C=1C=CC(O)=CC=1C=1CCC2=CC(OC)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCCC1 YIWBWKKNKYGJNR-UHFFFAOYSA-N 0.000 description 1
APIZNMTYIQNBPX-UHFFFAOYSA-N [2-(3-methoxy-2,4-dimethylphenyl)-3,4-dihydronaphthalen-1-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=2C(=C(OC)C(C)=CC=2)C)CCC2=CC=CC=C12 APIZNMTYIQNBPX-UHFFFAOYSA-N 0.000 description 1
SGZDTHHMUHOVKP-UHFFFAOYSA-N [2-(3-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanol Chemical compound COC1=CC=CC(C=2CCC3=CC=CC=C3C=2C(O)C=2C=CC(OCCN3CCCCC3)=CC=2)=C1 SGZDTHHMUHOVKP-UHFFFAOYSA-N 0.000 description 1
GVUPKWOITUCECX-UHFFFAOYSA-N [2-(4-fluoro-3-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=2C=C(OC)C(F)=CC=2)CCC2=CC=CC=C12 GVUPKWOITUCECX-UHFFFAOYSA-N 0.000 description 1
CPWQQDOUGRIJEC-UHFFFAOYSA-N [2-(4-fluoro-3-methoxyphenyl)-6-methoxy-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanol Chemical compound C=1C=C(F)C(OC)=CC=1C=1CCC2=CC(OC)=CC=C2C=1C(O)C(C=C1)=CC=C1OCCN1CCCCC1 CPWQQDOUGRIJEC-UHFFFAOYSA-N 0.000 description 1
XTRWVIGUHXIGKH-UHFFFAOYSA-N [2-(4-fluoro-3-methoxyphenyl)-6-methoxy-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C=1C=C(F)C(OC)=CC=1C=1CCC2=CC(OC)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCCC1 XTRWVIGUHXIGKH-UHFFFAOYSA-N 0.000 description 1
JHCYTEWIXWCCIE-UHFFFAOYSA-N [4-(2-bromoethoxy)phenyl]-[2-(2-chloro-3-methoxyphenyl)-6-methoxy-3,4-dihydronaphthalen-1-yl]methanone Chemical compound C=1C=CC(OC)=C(Cl)C=1C=1CCC2=CC(OC)=CC=C2C=1C(=O)C1=CC=C(OCCBr)C=C1 JHCYTEWIXWCCIE-UHFFFAOYSA-N 0.000 description 1
RZQAGRTUGPEQBT-UHFFFAOYSA-N [4-(2-bromoethoxy)phenyl]-[2-(3-chlorophenyl)-6-methoxy-3,4-dihydronaphthalen-1-yl]methanone Chemical compound C=1C=CC(Cl)=CC=1C=1CCC2=CC(OC)=CC=C2C=1C(=O)C1=CC=C(OCCBr)C=C1 RZQAGRTUGPEQBT-UHFFFAOYSA-N 0.000 description 1
MWNBYRCKTZLNNZ-UHFFFAOYSA-N [4-(2-bromoethoxy)phenyl]-[2-(4-fluoro-3-methoxyphenyl)-6-methoxy-3,4-dihydronaphthalen-1-yl]methanone Chemical compound C=1C=C(F)C(OC)=CC=1C=1CCC2=CC(OC)=CC=C2C=1C(=O)C1=CC=C(OCCBr)C=C1 MWNBYRCKTZLNNZ-UHFFFAOYSA-N 0.000 description 1
LBTNGNNUOAAKFW-UHFFFAOYSA-N [4-(2-bromoethoxy)phenyl]-[2-(4-methoxy-3-methylphenyl)-3,4-dihydronaphthalen-1-yl]methanone Chemical compound C1=C(C)C(OC)=CC=C1C(CCC1=CC=CC=C11)=C1C(=O)C1=CC=C(OCCBr)C=C1 LBTNGNNUOAAKFW-UHFFFAOYSA-N 0.000 description 1
YTHVCDAAIQOHJD-UHFFFAOYSA-N [4-(3-bromopropoxy)phenyl]-[6-methoxy-2-(3-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]methanone Chemical compound C=1C=CC(OC)=CC=1C=1CCC2=CC(OC)=CC=C2C=1C(=O)C1=CC=C(OCCCBr)C=C1 YTHVCDAAIQOHJD-UHFFFAOYSA-N 0.000 description 1
UXRGOIUBTAMHSY-UHFFFAOYSA-N [6-hydroxy-2-(2-hydroxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C=1C=CC=C(O)C=1C=1CCC2=CC(O)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCCC1 UXRGOIUBTAMHSY-UHFFFAOYSA-N 0.000 description 1
LHEPIUWKBVQHHR-UHFFFAOYSA-N [6-hydroxy-2-(3-hydroxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C=1C=CC(O)=CC=1C=1CCC2=CC(O)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCC1 LHEPIUWKBVQHHR-UHFFFAOYSA-N 0.000 description 1
OTKFRZCUUJBVDH-UHFFFAOYSA-N [6-hydroxy-2-(3-hydroxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(3-piperidin-1-ylpropoxy)phenyl]methanone Chemical compound C=1C=CC(O)=CC=1C=1CCC2=CC(O)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCCN1CCCCC1 OTKFRZCUUJBVDH-UHFFFAOYSA-N 0.000 description 1
JGVLKHZDIGDYKE-UHFFFAOYSA-N [6-hydroxy-2-(3-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound COC1=CC=CC(C=2CCC3=CC(O)=CC=C3C=2C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)=C1 JGVLKHZDIGDYKE-UHFFFAOYSA-N 0.000 description 1
QFWBXCCVCRGHPB-UHFFFAOYSA-N [6-methoxy-2-(2-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=2C(=CC=CC=2)OC)CCC2=CC(OC)=CC=C12 QFWBXCCVCRGHPB-UHFFFAOYSA-N 0.000 description 1
ZVWFDOCFFBUJKH-UHFFFAOYSA-N [6-methoxy-2-(2-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanol Chemical compound C=1C=CC=C(OC)C=1C=1CCC2=CC(OC)=CC=C2C=1C(O)C(C=C1)=CC=C1OCCN1CCCCC1 ZVWFDOCFFBUJKH-UHFFFAOYSA-N 0.000 description 1
QJJXUUIQKVKMAT-UHFFFAOYSA-N [6-methoxy-2-(2-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C=1C=CC=C(OC)C=1C=1CCC2=CC(OC)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCCC1 QJJXUUIQKVKMAT-UHFFFAOYSA-N 0.000 description 1
NSLDXFALNKTPQM-UHFFFAOYSA-N [6-methoxy-2-(3-methoxy-2-methylphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanol Chemical compound C=1C=CC(OC)=C(C)C=1C=1CCC2=CC(OC)=CC=C2C=1C(O)C(C=C1)=CC=C1OCCN1CCCCC1 NSLDXFALNKTPQM-UHFFFAOYSA-N 0.000 description 1
JNRAJPWGMUSOPP-UHFFFAOYSA-N [6-methoxy-2-(3-methoxy-2-methylphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C=1C=CC(OC)=C(C)C=1C=1CCC2=CC(OC)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCCC1 JNRAJPWGMUSOPP-UHFFFAOYSA-N 0.000 description 1
VYLYFTDFUFYSRR-UHFFFAOYSA-N [6-methoxy-2-(3-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanol Chemical compound COC1=CC=CC(C=2CCC3=CC(OC)=CC=C3C=2C(O)C=2C=CC(OCCN3CCCCC3)=CC=2)=C1 VYLYFTDFUFYSRR-UHFFFAOYSA-N 0.000 description 1
CIHOZFBHZRKDET-UHFFFAOYSA-N [6-methoxy-2-(3-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone;hydrochloride Chemical compound Cl.C=1C=CC(OC)=CC=1C=1CCC2=CC(OC)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCCC1 CIHOZFBHZRKDET-UHFFFAOYSA-N 0.000 description 1
WSFXONWZKCACJY-UHFFFAOYSA-N [6-methoxy-2-(3-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanol Chemical compound C=1C=CC(OC)=CC=1C=1CCC2=CC(OC)=CC=C2C=1C(O)C(C=C1)=CC=C1OCCN1CCCC1 WSFXONWZKCACJY-UHFFFAOYSA-N 0.000 description 1
PXILOZSCGNSYCT-UHFFFAOYSA-N [6-methoxy-2-(3-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(3-piperidin-1-ylpropoxy)phenyl]methanol Chemical compound C=1C=CC(OC)=CC=1C=1CCC2=CC(OC)=CC=C2C=1C(O)C(C=C1)=CC=C1OCCCN1CCCCC1 PXILOZSCGNSYCT-UHFFFAOYSA-N 0.000 description 1
OBQAUNRPNIQSCR-UHFFFAOYSA-N [6-methoxy-2-(3-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(3-piperidin-1-ylpropoxy)phenyl]methanone Chemical compound C=1C=CC(OC)=CC=1C=1CCC2=CC(OC)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCCN1CCCCC1 OBQAUNRPNIQSCR-UHFFFAOYSA-N 0.000 description 1
AQYBIAKVLZTAKT-UHFFFAOYSA-N [6-methoxy-2-(3-methoxyphenyl)naphthalen-1-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=2C=C(OC)C=CC=2)C=CC2=CC(OC)=CC=C12 AQYBIAKVLZTAKT-UHFFFAOYSA-N 0.000 description 1
DWWHWTFQCJWTDI-UHFFFAOYSA-N [6-methoxy-2-(3-methoxyphenyl)naphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound COC1=CC=CC(C=2C(=C3C=CC(OC)=CC3=CC=2)C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)=C1 DWWHWTFQCJWTDI-UHFFFAOYSA-N 0.000 description 1
YLLATSHZXUVPND-UHFFFAOYSA-N [6-methoxy-2-(3-methylphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanol Chemical compound C=1C=CC(C)=CC=1C=1CCC2=CC(OC)=CC=C2C=1C(O)C(C=C1)=CC=C1OCCN1CCCCC1 YLLATSHZXUVPND-UHFFFAOYSA-N 0.000 description 1
NFSMTXPGEBBLLV-UHFFFAOYSA-M [Br-].CC1=CC=CC([Mg+])=C1 Chemical compound [Br-].CC1=CC=CC([Mg+])=C1 NFSMTXPGEBBLLV-UHFFFAOYSA-M 0.000 description 1
QHGDTNICCBNQFB-UHFFFAOYSA-M [Br-].COC1=CC([Mg+])=CC=C1F Chemical compound [Br-].COC1=CC([Mg+])=CC=C1F QHGDTNICCBNQFB-UHFFFAOYSA-M 0.000 description 1
NQTAUIUPWYKMRS-UHFFFAOYSA-N [[6-methoxy-2-(3-methoxyphenyl)naphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methyl] methanesulfonate Chemical compound COC1=CC=CC(C=2C(=C3C=CC(OC)=CC3=CC=2)C(OS(C)(=O)=O)C=2C=CC(OCCN3CCCCC3)=CC=2)=C1 NQTAUIUPWYKMRS-UHFFFAOYSA-N 0.000 description 1
239000003655 absorption accelerator Substances 0.000 description 1
IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
YTIVTFGABIZHHX-UHFFFAOYSA-L acetylenedicarboxylate(2-) Chemical compound [O-]C(=O)C#CC([O-])=O YTIVTFGABIZHHX-UHFFFAOYSA-L 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
206010000496 acne Diseases 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
230000000274 adsorptive effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229940062527 alendronate Drugs 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
159000000032 aromatic acids Chemical class 0.000 description 1
238000005899 aromatization reaction Methods 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
229940072107 ascorbate Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
230000008901 benefit Effects 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
150000004663 bisphosphonates Chemical class 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
IXIBAKNTJSCKJM-BUBXBXGNSA-N bovine insulin Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3NC=NC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 IXIBAKNTJSCKJM-BUBXBXGNSA-N 0.000 description 1
201000008274 breast adenocarcinoma Diseases 0.000 description 1
244000309464 bull Species 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 1
229960004015 calcitonin Drugs 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229960005069 calcium Drugs 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
230000005907 cancer growth Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
230000036996 cardiovascular health Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
JOYKCMAPFCSKNO-UHFFFAOYSA-N chloro benzenesulfonate Chemical compound ClOS(=O)(=O)C1=CC=CC=C1 JOYKCMAPFCSKNO-UHFFFAOYSA-N 0.000 description 1
KVSASDOGYIBWTA-UHFFFAOYSA-N chloro benzoate Chemical compound ClOC(=O)C1=CC=CC=C1 KVSASDOGYIBWTA-UHFFFAOYSA-N 0.000 description 1
229960002559 chlorotrianisene Drugs 0.000 description 1
BFPSDSIWYFKGBC-UHFFFAOYSA-N chlorotrianisene Chemical compound C1=CC(OC)=CC=C1C(Cl)=C(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 BFPSDSIWYFKGBC-UHFFFAOYSA-N 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
229940114081 cinnamate Drugs 0.000 description 1
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 1
229960003608 clomifene Drugs 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229940035811 conjugated estrogen Drugs 0.000 description 1
229940109239 creatinine Drugs 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
PDRGHUMCVRDZLQ-UHFFFAOYSA-N d-equilenin Natural products OC1=CC=C2C(CCC3(C4CCC3=O)C)=C4C=CC2=C1 PDRGHUMCVRDZLQ-UHFFFAOYSA-N 0.000 description 1
GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
238000003795 desorption Methods 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
NFDFQCUYFHCNBW-SCGPFSFSSA-N dienestrol Chemical compound C=1C=C(O)C=CC=1\C(=C/C)\C(=C\C)\C1=CC=C(O)C=C1 NFDFQCUYFHCNBW-SCGPFSFSSA-N 0.000 description 1
229960003839 dienestrol Drugs 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
235000011180 diphosphates Nutrition 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229950004203 droloxifene Drugs 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000001278 effect on cholesterol Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
150000002085 enols Chemical group 0.000 description 1
PDRGHUMCVRDZLQ-WMZOPIPTSA-N equilenin Chemical compound OC1=CC=C2C(CC[C@]3([C@H]4CCC3=O)C)=C4C=CC2=C1 PDRGHUMCVRDZLQ-WMZOPIPTSA-N 0.000 description 1
238000011067 equilibration Methods 0.000 description 1
WKRLQDKEXYKHJB-HFTRVMKXSA-N equilin Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4C3=CCC2=C1 WKRLQDKEXYKHJB-HFTRVMKXSA-N 0.000 description 1
QTTMOCOWZLSYSV-QWAPEVOJSA-M equilin sodium sulfate Chemical compound [Na+].[O-]S(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4C3=CCC2=C1 QTTMOCOWZLSYSV-QWAPEVOJSA-M 0.000 description 1
229930182833 estradiol Natural products 0.000 description 1
229960005309 estradiol Drugs 0.000 description 1
229960005416 estradiol cypionate Drugs 0.000 description 1
229960004766 estradiol valerate Drugs 0.000 description 1
PROQIPRRNZUXQM-ZXXIGWHRSA-N estriol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H]([C@H](O)C4)O)[C@@H]4[C@@H]3CCC2=C1 PROQIPRRNZUXQM-ZXXIGWHRSA-N 0.000 description 1
229960001348 estriol Drugs 0.000 description 1
229960003399 estrone Drugs 0.000 description 1
HZEQBCVBILBTEP-ZFINNJDLSA-N estropipate Chemical compound C1CNCCN1.OS(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 HZEQBCVBILBTEP-ZFINNJDLSA-N 0.000 description 1
229940081345 estropipate Drugs 0.000 description 1
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229940001490 fosamax Drugs 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000007710 freezing Methods 0.000 description 1
210000001035 gastrointestinal tract Anatomy 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
RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 1
YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
208000035474 group of disease Diseases 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
239000003906 humectant Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
229960002591 hydroxyproline Drugs 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
238000010829 isocratic elution Methods 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
JPSNJFMTQIIVFG-UHFFFAOYSA-M lithium;ethanethiolate Chemical compound [Li+].CC[S-] JPSNJFMTQIIVFG-UHFFFAOYSA-M 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
ZMPYQGQHGLLBQI-UHFFFAOYSA-M magnesium;chlorobenzene;bromide Chemical compound [Mg+2].[Br-].ClC1=CC=C[C-]=C1 ZMPYQGQHGLLBQI-UHFFFAOYSA-M 0.000 description 1
DTKMKZYEOXZPQZ-UHFFFAOYSA-M magnesium;fluorobenzene;bromide Chemical compound [Mg+2].[Br-].FC1=CC=C[C-]=C1 DTKMKZYEOXZPQZ-UHFFFAOYSA-M 0.000 description 1
FCPRDUXJWIUVPZ-UHFFFAOYSA-M magnesium;methoxybenzene;bromide Chemical compound [Mg+2].[Br-].COC1=CC=CC=[C-]1 FCPRDUXJWIUVPZ-UHFFFAOYSA-M 0.000 description 1
YAMQOOCGNXAQGW-UHFFFAOYSA-M magnesium;methylbenzene;bromide Chemical compound [Mg+2].[Br-].CC1=CC=CC=[C-]1 YAMQOOCGNXAQGW-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
229960004616 medroxyprogesterone Drugs 0.000 description 1
FRQMUZJSZHZSGN-HBNHAYAOSA-N medroxyprogesterone Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](O)(C(C)=O)CC[C@H]21 FRQMUZJSZHZSGN-HBNHAYAOSA-N 0.000 description 1
PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
229960004296 megestrol acetate Drugs 0.000 description 1
RQZAXGRLVPAYTJ-GQFGMJRRSA-N megestrol acetate Chemical compound C1=C(C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RQZAXGRLVPAYTJ-GQFGMJRRSA-N 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000005906 menstruation Effects 0.000 description 1
IMSSROKUHAOUJS-MJCUULBUSA-N mestranol Chemical compound C1C[C@]2(C)[C@@](C#C)(O)CC[C@H]2[C@@H]2CCC3=CC(OC)=CC=C3[C@H]21 IMSSROKUHAOUJS-MJCUULBUSA-N 0.000 description 1
229960001390 mestranol Drugs 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
125000005341 metaphosphate group Chemical group 0.000 description 1
FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
PPGQXIUFJSJUMP-UHFFFAOYSA-N methyl 2-[(4-methoxyphenyl)methyl]-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound CC(C)(C)OC(=O)NCC(C(=O)OC)CC1=CC=C(OC)C=C1 PPGQXIUFJSJUMP-UHFFFAOYSA-N 0.000 description 1
IZYBEMGNIUSSAX-UHFFFAOYSA-N methyl benzenecarboperoxoate Chemical compound COOC(=O)C1=CC=CC=C1 IZYBEMGNIUSSAX-UHFFFAOYSA-N 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
230000000921 morphogenic effect Effects 0.000 description 1
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-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
XMRSVLCCIJUKDQ-UHFFFAOYSA-N n-diazobenzenesulfonamide Chemical compound [N-]=[N+]=NS(=O)(=O)C1=CC=CC=C1 XMRSVLCCIJUKDQ-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
229960001858 norethynodrel Drugs 0.000 description 1
230000001473 noxious effect Effects 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
239000002674 ointment Substances 0.000 description 1
238000009806 oophorectomy Methods 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
239000003960 organic solvent Substances 0.000 description 1
230000011164 ossification Effects 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229960003531 phenolsulfonphthalein Drugs 0.000 description 1
DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
229950009215 phenylbutanoic acid Drugs 0.000 description 1
IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
230000000865 phosphorylative effect Effects 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
239000006187 pill Substances 0.000 description 1
229960001298 polyestradiol phosphate Drugs 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
201000010808 postmenopausal atrophic vaginitis Diseases 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
230000001072 progestational effect Effects 0.000 description 1
239000000186 progesterone Substances 0.000 description 1
229960003387 progesterone Drugs 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
HLVVVMPXONYIGM-UHFFFAOYSA-N propane-1-sulfonyl bromide Chemical compound CCCS(Br)(=O)=O HLVVVMPXONYIGM-UHFFFAOYSA-N 0.000 description 1
HNDXKIMMSFCCFW-UHFFFAOYSA-M propane-2-sulfonate Chemical compound CC(C)S([O-])(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-M 0.000 description 1
239000003380 propellant Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000005588 protonation Effects 0.000 description 1
229940063222 provera Drugs 0.000 description 1
239000008213 purified water Substances 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 description 1
229960004622 raloxifene Drugs 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000001850 reproductive effect Effects 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229940116351 sebacate Drugs 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229940054269 sodium pyruvate Drugs 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000012058 sterile packaged powder Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229940086735 succinate Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
OGBMKVWORPGQRR-UMXFMPSGSA-N teriparatide Chemical compound C([C@H](NC(=O)[C@H](CCSC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@@H](N)CO)C(C)C)[C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C1=CNC=N1 OGBMKVWORPGQRR-UMXFMPSGSA-N 0.000 description 1
238000010257 thawing Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000007944 thiolates Chemical class 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
229940019375 tiludronate Drugs 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1
FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
230000004565 tumor cell growth Effects 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
230000001836 utereotrophic effect Effects 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1
229940071104 xylenesulfonate Drugs 0.000 description 1