JP4160295B2

JP4160295B2 - ３−ピリジル基を有する置換チアゾール誘導体、その製造法および用途

３−ピリジル基を有する置換チアゾール誘導体、その製造法および用途 Download PDF

Info

Publication number: JP4160295B2
Authority: JP; Japan
Prior art keywords: group; substituent; optionally; optionally substituted; pyridyl
Prior art date: 2000-12-08
Legal status : Expired - Fee Related

Application number

JP2001375062A

Other languages

English (en)

Japanese (ja)

Other versions

JP2002234843A (ja

JP2002234843A5 (https=

Inventor

典孝黒田

禎奈良

昌平橋口

昭弘田坂

雅美日下

万寿夫山岡

智弘加来

Current Assignee

Takeda Pharmaceutical Co Ltd

Original Assignee

Takeda Pharmaceutical Co Ltd

Priority date

2000-12-08

Filing date

2001-12-07

Publication date

2008-10-01

2001-12-07 Application filed by Takeda Pharmaceutical Co Ltd filed Critical Takeda Pharmaceutical Co Ltd

2001-12-07 Priority to JP2001375062A priority Critical patent/JP4160295B2/ja

2002-08-23 Publication of JP2002234843A publication Critical patent/JP2002234843A/ja

2005-05-26 Publication of JP2002234843A5 publication Critical patent/JP2002234843A5/ja

2008-10-01 Application granted granted Critical

2008-10-01 Publication of JP4160295B2 publication Critical patent/JP4160295B2/ja

2021-12-07 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 title claims description 49
238000004519 manufacturing process Methods 0.000 title description 20
150000007979 thiazole derivatives Chemical class 0.000 title description 2
-1 4-benzyl-piperidinyloxy Chemical group 0.000 claims description 582
150000001875 compounds Chemical class 0.000 claims description 397
125000001424 substituent group Chemical group 0.000 claims description 232
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 108
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 106
125000005843 halogen group Chemical group 0.000 claims description 89
150000003839 salts Chemical class 0.000 claims description 66
125000001931 aliphatic group Chemical group 0.000 claims description 63
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 60
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 51
229910052801 chlorine Inorganic materials 0.000 claims description 47
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 38
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 37
229910052731 fluorine Inorganic materials 0.000 claims description 37
125000005530 alkylenedioxy group Chemical group 0.000 claims description 33
125000000623 heterocyclic group Chemical group 0.000 claims description 33
239000003814 drug Substances 0.000 claims description 30
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 29
239000002697 lyase inhibitor Substances 0.000 claims description 27
125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 27
229920006395 saturated elastomer Polymers 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 25
125000001309 chloro group Chemical group Cl* 0.000 claims description 25
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
125000004414 alkyl thio group Chemical group 0.000 claims description 24
IHOBBYHEOBWAPZ-UHFFFAOYSA-L steroid c Chemical compound [Na+].[Na+].C1CC2CC(OS([O-])(=O)=O)C(OS([O-])(=O)=O)CC2(C)C(CCC23C)C1C3CC(O1)C2C2(C)OC1OC2CC(C(C)C)=C(C)C IHOBBYHEOBWAPZ-UHFFFAOYSA-L 0.000 claims description 24
239000000460 chlorine Substances 0.000 claims description 23
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 22
125000004122 cyclic group Chemical group 0.000 claims description 22
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 20
239000011737 fluorine Substances 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 17
239000003795 chemical substances by application Substances 0.000 claims description 17
125000001153 fluoro group Chemical group F* 0.000 claims description 17
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
229940122014 Lyase inhibitor Drugs 0.000 claims description 14
239000003098 androgen Substances 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 12
102000004317 Lyases Human genes 0.000 claims description 11
108090000856 Lyases Proteins 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
201000010099 disease Diseases 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
229940011871 estrogen Drugs 0.000 claims description 9
239000000262 estrogen Substances 0.000 claims description 9
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 9
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 8
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
102000008238 LHRH Receptors Human genes 0.000 claims description 7
108010021290 LHRH Receptors Proteins 0.000 claims description 7
239000003163 gonadal steroid hormone Substances 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
201000004384 Alopecia Diseases 0.000 claims description 5
206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 5
206010020112 Hirsutism Diseases 0.000 claims description 5
206010036590 Premature baby Diseases 0.000 claims description 5
208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 5
206010046798 Uterine leiomyoma Diseases 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
208000030270 breast disease Diseases 0.000 claims description 5
201000010260 leiomyoma Diseases 0.000 claims description 5
201000010065 polycystic ovary syndrome Diseases 0.000 claims description 5
230000000069 prophylactic effect Effects 0.000 claims description 5
229940124597 therapeutic agent Drugs 0.000 claims description 5
201000009273 Endometriosis Diseases 0.000 claims description 4
201000009274 endometriosis of uterus Diseases 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
125000001589 carboacyl group Chemical group 0.000 claims description 3
230000001419 dependent effect Effects 0.000 claims description 3
230000003676 hair loss Effects 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims description 2
230000005764 inhibitory process Effects 0.000 claims description 2
125000005915 C6-C14 aryl group Chemical group 0.000 claims 3
VFTOHJFKIJLYKN-UHFFFAOYSA-N 7-nitro-9h-fluoren-2-ol Chemical compound [O-][N+](=O)C1=CC=C2C3=CC=C(O)C=C3CC2=C1 VFTOHJFKIJLYKN-UHFFFAOYSA-N 0.000 claims 1
125000004423 acyloxy group Chemical group 0.000 claims 1
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
239000003112 inhibitor Substances 0.000 claims 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 256
238000006243 chemical reaction Methods 0.000 description 184
238000005160 1H NMR spectroscopy Methods 0.000 description 154
238000002360 preparation method Methods 0.000 description 152
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 124
239000013078 crystal Substances 0.000 description 94
239000000843 powder Substances 0.000 description 92
239000000243 solution Substances 0.000 description 85
238000000034 method Methods 0.000 description 75
235000002639 sodium chloride Nutrition 0.000 description 69
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
125000003277 amino group Chemical group 0.000 description 55
239000000203 mixture Substances 0.000 description 54
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 49
230000002829 reductive effect Effects 0.000 description 49
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 47
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
239000002904 solvent Substances 0.000 description 43
239000012044 organic layer Substances 0.000 description 37
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 36
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
229910052799 carbon Inorganic materials 0.000 description 29
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 28
229910052794 bromium Inorganic materials 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
238000010898 silica gel chromatography Methods 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
238000000921 elemental analysis Methods 0.000 description 24
229940079593 drug Drugs 0.000 description 23
238000002844 melting Methods 0.000 description 23
230000008018 melting Effects 0.000 description 23
229910052757 nitrogen Inorganic materials 0.000 description 23
OVQVUSADZFZNNS-UHFFFAOYSA-N 2-bromo-1-(4-methylpyridin-3-yl)ethanone;hydrobromide Chemical compound Br.CC1=CC=NC=C1C(=O)CBr OVQVUSADZFZNNS-UHFFFAOYSA-N 0.000 description 22
125000004433 nitrogen atom Chemical group N* 0.000 description 21
125000003710 aryl alkyl group Chemical group 0.000 description 20
239000011541 reaction mixture Substances 0.000 description 20
125000004432 carbon atom Chemical group C* 0.000 description 19
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 19
229940002612 prodrug Drugs 0.000 description 19
239000000651 prodrug Substances 0.000 description 19
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
238000001816 cooling Methods 0.000 description 17
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 16
239000002994 raw material Substances 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000000126 substance Substances 0.000 description 15
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 14
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
239000003480 eluent Substances 0.000 description 13
239000000284 extract Substances 0.000 description 13
239000010410 layer Substances 0.000 description 13
239000003921 oil Substances 0.000 description 13
235000019198 oils Nutrition 0.000 description 13
238000010992 reflux Methods 0.000 description 13
150000003431 steroids Chemical class 0.000 description 13
125000005415 substituted alkoxy group Chemical group 0.000 description 13
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 12
235000017557 sodium bicarbonate Nutrition 0.000 description 12
229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
238000003756 stirring Methods 0.000 description 12
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 11
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
229910052740 iodine Inorganic materials 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 10
238000001914 filtration Methods 0.000 description 10
239000000047 product Substances 0.000 description 10
XLAPHZHNODDMDD-UHFFFAOYSA-N 4-methylpyridine-3-carbonitrile Chemical compound CC1=CC=NC=C1C#N XLAPHZHNODDMDD-UHFFFAOYSA-N 0.000 description 9
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
239000012267 brine Substances 0.000 description 9
230000010261 cell growth Effects 0.000 description 9
230000000694 effects Effects 0.000 description 9
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
OYUNSJVIHQHOIM-UHFFFAOYSA-N 2-bromo-1-(2,4-dimethylphenyl)-2-phenylethanone Chemical compound CC1=CC(C)=CC=C1C(=O)C(Br)C1=CC=CC=C1 OYUNSJVIHQHOIM-UHFFFAOYSA-N 0.000 description 8
WDIPQCJUEWOCJT-UHFFFAOYSA-N 4-methylpyridine-3-carbothioamide Chemical compound CC1=CC=NC=C1C(N)=S WDIPQCJUEWOCJT-UHFFFAOYSA-N 0.000 description 8
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 8
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 8
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 8
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 8
239000003960 organic solvent Substances 0.000 description 8
125000000547 substituted alkyl group Chemical group 0.000 description 8
125000001544 thienyl group Chemical group 0.000 description 8
QBKPXDUZFDINDV-UHFFFAOYSA-N 4-chloropyridine-3-carbonitrile Chemical compound ClC1=CC=NC=C1C#N QBKPXDUZFDINDV-UHFFFAOYSA-N 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 7
229910021590 Copper(II) bromide Inorganic materials 0.000 description 7
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
238000007796 conventional method Methods 0.000 description 7
239000003102 growth factor Substances 0.000 description 7
239000011630 iodine Substances 0.000 description 7
239000008101 lactose Substances 0.000 description 7
235000019359 magnesium stearate Nutrition 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
239000000825 pharmaceutical preparation Substances 0.000 description 7
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 7
102000005962 receptors Human genes 0.000 description 7
108020003175 receptors Proteins 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 6
125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 6
LCEINQHGZAFADC-UHFFFAOYSA-N 1-(4-methylpyridin-3-yl)ethanone Chemical compound CC(=O)C1=CN=CC=C1C LCEINQHGZAFADC-UHFFFAOYSA-N 0.000 description 6
OJVXIEGAUZGHDR-UHFFFAOYSA-N 4-ethylpyridine-3-carbonitrile Chemical compound CCC1=CC=NC=C1C#N OJVXIEGAUZGHDR-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
229920002261 Corn starch Polymers 0.000 description 6
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
229920002472 Starch Polymers 0.000 description 6
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
239000008120 corn starch Substances 0.000 description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
238000009472 formulation Methods 0.000 description 6
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 6
229910000037 hydrogen sulfide Inorganic materials 0.000 description 6
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
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 description 6
125000006239 protecting group Chemical group 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000008107 starch Substances 0.000 description 6
235000019698 starch Nutrition 0.000 description 6
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 5
MUTFXQJYBJMMFG-UHFFFAOYSA-N 2-bromo-1-(4-ethylpyridin-3-yl)ethanone hydrobromide Chemical compound Br.CCc1ccncc1C(=O)CBr MUTFXQJYBJMMFG-UHFFFAOYSA-N 0.000 description 5
QBRGRSYZRUCWNH-UHFFFAOYSA-N 2-bromo-4-(4-chlorophenyl)-1,3-thiazole Chemical compound C1=CC(Cl)=CC=C1C1=CSC(Br)=N1 QBRGRSYZRUCWNH-UHFFFAOYSA-N 0.000 description 5
ZMEMLNQJRMTRCU-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(4-chloropyridin-3-yl)-1,3-thiazole Chemical compound C1=CC(Cl)=CC=C1C1=CSC(C=2C(=CC=NC=2)Cl)=N1 ZMEMLNQJRMTRCU-UHFFFAOYSA-N 0.000 description 5
DYRMBQRXOMOMNW-UHFFFAOYSA-N 4-chloropyridine-3-carbaldehyde Chemical compound ClC1=CC=NC=C1C=O DYRMBQRXOMOMNW-UHFFFAOYSA-N 0.000 description 5
125000002373 5 membered heterocyclic group Chemical group 0.000 description 5
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
239000005711 Benzoic acid Substances 0.000 description 5
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 5
102000018233 Fibroblast Growth Factor Human genes 0.000 description 5
108050007372 Fibroblast Growth Factor Proteins 0.000 description 5
101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 description 5
102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 5
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
235000010233 benzoic acid Nutrition 0.000 description 5
201000011510 cancer Diseases 0.000 description 5
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 5
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
229940126864 fibroblast growth factor Drugs 0.000 description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
230000002140 halogenating effect Effects 0.000 description 5
150000002430 hydrocarbons Chemical group 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
230000002401 inhibitory effect Effects 0.000 description 5
150000007524 organic acids Chemical class 0.000 description 5
VJIHFHYGNAOPPU-UHFFFAOYSA-N s-cyano 2-(4-chlorophenyl)ethanethioate Chemical compound ClC1=CC=C(CC(=O)SC#N)C=C1 VJIHFHYGNAOPPU-UHFFFAOYSA-N 0.000 description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
WDTSYONULAZKIE-UHFFFAOYSA-N 2-bromo-1-pyridin-3-ylethanone;hydron;bromide Chemical compound [Br-].BrCC(=O)C1=CC=C[NH+]=C1 WDTSYONULAZKIE-UHFFFAOYSA-N 0.000 description 4
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 4
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 4
KEWIQALTMXCKSH-UHFFFAOYSA-N 3-[2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]benzoic acid Chemical compound CC1=CC=NC=C1C1=NC(C=2C=C(C=CC=2)C(O)=O)=CS1 KEWIQALTMXCKSH-UHFFFAOYSA-N 0.000 description 4
HTQCFZPTODLHQH-UHFFFAOYSA-N 3-[2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazol-4-yl]aniline Chemical compound NC1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C(F)(F)F)=C1 HTQCFZPTODLHQH-UHFFFAOYSA-N 0.000 description 4
LKOWUDYGBOMPTM-UHFFFAOYSA-N 3-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-2-methylpyridine-4-carboxylic acid Chemical compound CC1=NC=CC(C(O)=O)=C1C1=NC(C=2C=CC(Cl)=CC=2)=CS1 LKOWUDYGBOMPTM-UHFFFAOYSA-N 0.000 description 4
JCOQBCLTGOENLA-UHFFFAOYSA-N 3-iodo-4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1I JCOQBCLTGOENLA-UHFFFAOYSA-N 0.000 description 4
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
STNJYJAJIRQBHF-UHFFFAOYSA-N 4-[2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]benzenesulfonamide Chemical compound CC1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)S(N)(=O)=O)=CS1 STNJYJAJIRQBHF-UHFFFAOYSA-N 0.000 description 4
HTHKGFUYXFAKNV-UHFFFAOYSA-N 4-[2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazol-4-yl]aniline Chemical compound C1=CC(N)=CC=C1C1=CSC(C=2C(=CC=NC=2)C(F)(F)F)=N1 HTHKGFUYXFAKNV-UHFFFAOYSA-N 0.000 description 4
KWTIXZMJYDTFJM-UHFFFAOYSA-N 4-ethenylpyridine-3-carbonitrile Chemical compound C=CC1=CC=NC=C1C#N KWTIXZMJYDTFJM-UHFFFAOYSA-N 0.000 description 4
RTVZZFXJASCNCE-UHFFFAOYSA-N 4-methoxypyridine-3-carbonitrile Chemical compound COC1=CC=NC=C1C#N RTVZZFXJASCNCE-UHFFFAOYSA-N 0.000 description 4
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
101100132433 Arabidopsis thaliana VIII-1 gene Proteins 0.000 description 4
GFSGXWFXCUZNAS-UHFFFAOYSA-N Br.CC(C)C1=CC=NC=C1C(=O)CBr Chemical compound Br.CC(C)C1=CC=NC=C1C(=O)CBr GFSGXWFXCUZNAS-UHFFFAOYSA-N 0.000 description 4
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
102000001301 EGF receptor Human genes 0.000 description 4
108060006698 EGF receptor Proteins 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
230000009471 action Effects 0.000 description 4
125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000012300 argon atmosphere Substances 0.000 description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
235000010980 cellulose Nutrition 0.000 description 4
229920002678 cellulose Polymers 0.000 description 4
239000001913 cellulose Substances 0.000 description 4
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 4
238000006482 condensation reaction Methods 0.000 description 4
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
125000000524 functional group Chemical group 0.000 description 4
239000007789 gas Substances 0.000 description 4
229940093915 gynecological organic acid Drugs 0.000 description 4
238000005658 halogenation reaction Methods 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 4
235000010355 mannitol Nutrition 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
OIZSNDSDCLHFQN-UHFFFAOYSA-N n,n-dibenzyl-4-(2-bromoacetyl)benzenesulfonamide Chemical compound C1=CC(C(=O)CBr)=CC=C1S(=O)(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 OIZSNDSDCLHFQN-UHFFFAOYSA-N 0.000 description 4
235000005152 nicotinamide Nutrition 0.000 description 4
239000011570 nicotinamide Substances 0.000 description 4
229960003966 nicotinamide Drugs 0.000 description 4
235000005985 organic acids Nutrition 0.000 description 4
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
229930195734 saturated hydrocarbon Natural products 0.000 description 4
238000012360 testing method Methods 0.000 description 4
125000003396 thiol group Chemical group [H]S* 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
229920002554 vinyl polymer Polymers 0.000 description 4
125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 description 3
125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 description 3
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 3
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
125000005999 2-bromoethyl group Chemical group 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
ULQOTJJATJHDAS-UHFFFAOYSA-N 3-iodo-n,n,4-trimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=C(C)C(I)=C1 ULQOTJJATJHDAS-UHFFFAOYSA-N 0.000 description 3
CGPOMGKVXLLMDX-UHFFFAOYSA-N 4-(2,4-dimethylphenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole;hydrochloride Chemical compound Cl.CC1=CC(C)=CC=C1C1=CSC(C=2C(=CC=NC=2)C)=N1 CGPOMGKVXLLMDX-UHFFFAOYSA-N 0.000 description 3
ORFGHTLYEABIRY-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=CC(Cl)=CC=2)=CS1 ORFGHTLYEABIRY-UHFFFAOYSA-N 0.000 description 3
XODFWCAVOQHJFC-UHFFFAOYSA-N 4-(4-chlorophenyl)-3h-1,3-thiazol-2-one Chemical compound C1=CC(Cl)=CC=C1C1=CSC(=O)N1 XODFWCAVOQHJFC-UHFFFAOYSA-N 0.000 description 3
UWWLJPXSMUXNOG-UHFFFAOYSA-N 4-[2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]benzoic acid Chemical compound CC1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)C(O)=O)=CS1 UWWLJPXSMUXNOG-UHFFFAOYSA-N 0.000 description 3
KOSOUOXOWJLMII-UHFFFAOYSA-N 4-[2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazol-4-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CSC(C=2C(=CC=NC=2)C(F)(F)F)=N1 KOSOUOXOWJLMII-UHFFFAOYSA-N 0.000 description 3
125000006618 5- to 10-membered aromatic heterocyclic group Chemical group 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
0 C*(C)Cc1cccc(-c2c(*)[s]c(-c3c(*)c(*)cnc3)n2)c1 Chemical compound C*(C)Cc1cccc(-c2c(*)[s]c(-c3c(*)c(*)cnc3)n2)c1 0.000 description 3
125000005914 C6-C14 aryloxy group Chemical group 0.000 description 3
BUKJJDAXOSOXOP-UHFFFAOYSA-N CC1=C(C=NC=C1)C(=O)C(C)Br.Br Chemical compound CC1=C(C=NC=C1)C(=O)C(C)Br.Br BUKJJDAXOSOXOP-UHFFFAOYSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
102400001368 Epidermal growth factor Human genes 0.000 description 3
101800003838 Epidermal growth factor Proteins 0.000 description 3
102000003951 Erythropoietin Human genes 0.000 description 3
108090000394 Erythropoietin Proteins 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
108090000723 Insulin-Like Growth Factor I Proteins 0.000 description 3
206010028980 Neoplasm Diseases 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
206010060862 Prostate cancer Diseases 0.000 description 3
208000000236 Prostatic Neoplasms Diseases 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
102000013275 Somatomedins Human genes 0.000 description 3
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
229930006000 Sucrose Natural products 0.000 description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
239000012346 acetyl chloride Substances 0.000 description 3
239000002253 acid Substances 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
235000001014 amino acid Nutrition 0.000 description 3
150000001413 amino acids Chemical class 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
239000002585 base Substances 0.000 description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
239000001768 carboxy methyl cellulose Substances 0.000 description 3
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 3
230000008878 coupling Effects 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 3
239000007884 disintegrant Substances 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
229940088598 enzyme Drugs 0.000 description 3
229940116977 epidermal growth factor Drugs 0.000 description 3
229940105423 erythropoietin Drugs 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 3
MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 3
125000006125 ethylsulfonyl group Chemical group 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000001530 fumaric acid Substances 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000002198 insoluble material Substances 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 3
239000000314 lubricant Substances 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
125000004430 oxygen atom Chemical group O* 0.000 description 3
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
125000004742 propyloxycarbonyl group Chemical group 0.000 description 3
229940075993 receptor modulator Drugs 0.000 description 3
239000008159 sesame oil Substances 0.000 description 3
235000011803 sesame oil Nutrition 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
239000000758 substrate Substances 0.000 description 3
239000005720 sucrose Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
125000004434 sulfur atom Chemical group 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
239000005483 tyrosine kinase inhibitor Substances 0.000 description 3
229940121358 tyrosine kinase inhibitor Drugs 0.000 description 3
VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
PHDZGBPNBLHTJT-UHFFFAOYSA-N (3-iodo-4-methylphenyl)-pyrrolidin-1-ylmethanone Chemical compound C1=C(I)C(C)=CC=C1C(=O)N1CCCC1 PHDZGBPNBLHTJT-UHFFFAOYSA-N 0.000 description 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 2
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 2
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 description 2
YQJXKHMRBXPWQS-UHFFFAOYSA-N 1-(4-methylpyridin-3-yl)propan-1-one Chemical compound CCC(=O)C1=CN=CC=C1C YQJXKHMRBXPWQS-UHFFFAOYSA-N 0.000 description 2
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 2
BNPJWSHRMGQVSG-UHFFFAOYSA-N 1-oxo-2,3-dihydroisoindole-4-carbothioamide Chemical compound NC(=S)C1=CC=CC2=C1CNC2=O BNPJWSHRMGQVSG-UHFFFAOYSA-N 0.000 description 2
VDNKJMUNLKAGAM-UHFFFAOYSA-N 1-pyridin-3-ylpropan-1-one Chemical compound CCC(=O)C1=CC=CN=C1 VDNKJMUNLKAGAM-UHFFFAOYSA-N 0.000 description 2
AGJATLRDZXCNDV-UHFFFAOYSA-N 2,4-dimethoxypyrimidine-5-carbonitrile Chemical compound COC1=NC=C(C#N)C(OC)=N1 AGJATLRDZXCNDV-UHFFFAOYSA-N 0.000 description 2
QWIDNZQVIOCZFC-UHFFFAOYSA-N 2,4-dimethoxypyrimidine-5-carbothioamide Chemical compound COC1=NC=C(C(N)=S)C(OC)=N1 QWIDNZQVIOCZFC-UHFFFAOYSA-N 0.000 description 2
IVSBMERICWXPLN-UHFFFAOYSA-N 2-(2,4-dimethoxypyrimidin-5-yl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound COC1=NC(OC)=NC=C1C1=NC(C=2C(=CC=NC=2)C)=CS1 IVSBMERICWXPLN-UHFFFAOYSA-N 0.000 description 2
SSVSDYFFUMAMHO-UHFFFAOYSA-N 2-(2-methyl-5-nitrophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C(=CC=C(C=2)[N+]([O-])=O)C)=N1 SSVSDYFFUMAMHO-UHFFFAOYSA-N 0.000 description 2
UPEHFYYPEFCBGV-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C=CC(F)=CC=2)=N1 UPEHFYYPEFCBGV-UHFFFAOYSA-N 0.000 description 2
AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical class CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
OKZWLWBBFIZXNE-UHFFFAOYSA-N 2-[3-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]pyridin-4-yl]propan-2-ol Chemical compound CC(C)(O)C1=CC=NC=C1C1=NC(C=2C=CC(Cl)=CC=2)=CS1 OKZWLWBBFIZXNE-UHFFFAOYSA-N 0.000 description 2
RXNZFHIEDZEUQM-UHFFFAOYSA-N 2-bromo-1,3-thiazole Chemical compound BrC1=NC=CS1 RXNZFHIEDZEUQM-UHFFFAOYSA-N 0.000 description 2
NVCNENXQUDVWRV-UHFFFAOYSA-N 2-bromo-1-(3-bromo-4-fluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CBr)C=C1Br NVCNENXQUDVWRV-UHFFFAOYSA-N 0.000 description 2
RIERXTXOIBGUSW-UHFFFAOYSA-N 2-chloro-5-cyano-n-methylbenzamide Chemical compound CNC(=O)C1=CC(C#N)=CC=C1Cl RIERXTXOIBGUSW-UHFFFAOYSA-N 0.000 description 2
OKHUBROPJSZSLG-UHFFFAOYSA-N 2-chloro-n-methyl-5-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]benzamide Chemical compound C1=C(Cl)C(C(=O)NC)=CC(C=2SC=C(N=2)C=2C(=CC=NC=2)C)=C1 OKHUBROPJSZSLG-UHFFFAOYSA-N 0.000 description 2
IGCHYOGADZFLHK-UHFFFAOYSA-N 2-methyl-4-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]-3h-isoindol-1-one Chemical compound O=C1N(C)CC2=C1C=CC=C2C(SC=1)=NC=1C1=CN=CC=C1C IGCHYOGADZFLHK-UHFFFAOYSA-N 0.000 description 2
BNJIRTGJVDWUAW-UHFFFAOYSA-N 2-methyl-5-nitrobenzenecarbothioamide Chemical compound CC1=CC=C([N+]([O-])=O)C=C1C(N)=S BNJIRTGJVDWUAW-UHFFFAOYSA-N 0.000 description 2
125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 description 2
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
XWCGNFLHRINYCE-UHFFFAOYSA-N 3-(2-bromoacetyl)benzonitrile Chemical compound BrCC(=O)C1=CC=CC(C#N)=C1 XWCGNFLHRINYCE-UHFFFAOYSA-N 0.000 description 2
WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 description 2
KDUYDLLJPHEHQD-UHFFFAOYSA-N 3-[2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]benzonitrile Chemical compound CC1=CC=NC=C1C1=NC(C=2C=C(C=CC=2)C#N)=CS1 KDUYDLLJPHEHQD-UHFFFAOYSA-N 0.000 description 2
OILUBPPQHGBXAA-UHFFFAOYSA-N 3-[2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazol-4-yl]benzonitrile Chemical compound FC(F)(F)C1=CC=NC=C1C1=NC(C=2C=C(C=CC=2)C#N)=CS1 OILUBPPQHGBXAA-UHFFFAOYSA-N 0.000 description 2
CQVWICTYIJQYMC-UHFFFAOYSA-N 3-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-n,n-dimethylpyridine-4-carboxamide Chemical compound CN(C)C(=O)C1=CC=NC=C1C1=NC(C=2C=CC(Cl)=CC=2)=CS1 CQVWICTYIJQYMC-UHFFFAOYSA-N 0.000 description 2
JBCDOXRHGXVXLS-UHFFFAOYSA-N 3-[4-(4-ethylpyridin-3-yl)-1,3-thiazol-2-yl]benzamide Chemical compound CCC1=CC=NC=C1C1=CSC(C=2C=C(C=CC=2)C(N)=O)=N1 JBCDOXRHGXVXLS-UHFFFAOYSA-N 0.000 description 2
KVAAJJRSKXOIIX-UHFFFAOYSA-N 3-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]benzamide Chemical compound CC1=CC=NC=C1C1=CSC(C=2C=C(C=CC=2)C(N)=O)=N1 KVAAJJRSKXOIIX-UHFFFAOYSA-N 0.000 description 2
YVVZOQRQAYFFIY-UHFFFAOYSA-N 3-[5-methyl-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]benzamide Chemical compound CC=1SC(C=2C=C(C=CC=2)C(N)=O)=NC=1C1=CN=CC=C1C YVVZOQRQAYFFIY-UHFFFAOYSA-N 0.000 description 2
NGGRBNLCFLPBCQ-UHFFFAOYSA-N 3-cyano-4-fluoro-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(F)C(C#N)=C1 NGGRBNLCFLPBCQ-UHFFFAOYSA-N 0.000 description 2
QAIPOQRSBWSIFC-UHFFFAOYSA-N 3-cyano-n,4-dimethylbenzamide Chemical compound CNC(=O)C1=CC=C(C)C(C#N)=C1 QAIPOQRSBWSIFC-UHFFFAOYSA-N 0.000 description 2
YMGRILKXIBCQFT-UHFFFAOYSA-N 3-cyano-n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC(C#N)=C1 YMGRILKXIBCQFT-UHFFFAOYSA-N 0.000 description 2
RPESZQVUWMFBEO-UHFFFAOYSA-N 3-cyanobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(C#N)=C1 RPESZQVUWMFBEO-UHFFFAOYSA-N 0.000 description 2
BJUUQJJXYSGLAD-UHFFFAOYSA-N 3-methyl-1-(4-methylpyridin-3-yl)butan-1-one Chemical compound CC(C)CC(=O)C1=CN=CC=C1C BJUUQJJXYSGLAD-UHFFFAOYSA-N 0.000 description 2
FREQQHVRMDVJQF-UHFFFAOYSA-N 3-sulfamoylbenzenecarbothioamide Chemical compound NC(=S)C1=CC=CC(S(N)(=O)=O)=C1 FREQQHVRMDVJQF-UHFFFAOYSA-N 0.000 description 2
IAQDWUWZDGAEBO-UHFFFAOYSA-N 4-(3-bromo-4-fluorophenyl)-2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazole Chemical compound C1=C(Br)C(F)=CC=C1C1=CSC(C=2C(=CC=NC=2)C(F)(F)F)=N1 IAQDWUWZDGAEBO-UHFFFAOYSA-N 0.000 description 2
TZLSMOAEVGIRLZ-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=CC(F)=CC=2)=CS1 TZLSMOAEVGIRLZ-UHFFFAOYSA-N 0.000 description 2
BXJNXSCXGBOMSP-UHFFFAOYSA-N 4-(4-methylpyridin-3-yl)-2-pyridin-2-yl-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2N=CC=CC=2)=N1 BXJNXSCXGBOMSP-UHFFFAOYSA-N 0.000 description 2
HOPAEPDXFOSQMZ-UHFFFAOYSA-N 4-(trifluoromethyl)pyridine-3-carbothioamide Chemical compound NC(=S)C1=CN=CC=C1C(F)(F)F HOPAEPDXFOSQMZ-UHFFFAOYSA-N 0.000 description 2
OTLWCKDJXGCTET-UHFFFAOYSA-N 4-[2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]benzamide Chemical compound CC1=CC=NC=C1C1=NC(C=2C=CC(=CC=2)C(N)=O)=CS1 OTLWCKDJXGCTET-UHFFFAOYSA-N 0.000 description 2
YVPNAIUIZFPOMS-UHFFFAOYSA-N 4-[2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazol-4-yl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CSC(C=2C(=CC=NC=2)C(F)(F)F)=N1 YVPNAIUIZFPOMS-UHFFFAOYSA-N 0.000 description 2
WPIVHEAXQBSFKW-UHFFFAOYSA-N 4-[2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazol-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=CSC(C=2C(=CC=NC=2)C(F)(F)F)=N1 WPIVHEAXQBSFKW-UHFFFAOYSA-N 0.000 description 2
IUMWUMQYWOYDHW-UHFFFAOYSA-N 4-[3-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]pyridin-4-yl]morpholine Chemical compound C1=CC(Cl)=CC=C1C1=CSC(C=2C(=CC=NC=2)N2CCOCC2)=N1 IUMWUMQYWOYDHW-UHFFFAOYSA-N 0.000 description 2
UNLUBONVCRJJNA-UHFFFAOYSA-N 4-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]-2,3-dihydroisoindol-1-one Chemical compound CC1=CC=NC=C1C1=CSC(C=2C=3CNC(=O)C=3C=CC=2)=N1 UNLUBONVCRJJNA-UHFFFAOYSA-N 0.000 description 2
VBZPQGUCYLDFNX-UHFFFAOYSA-N 4-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]benzamide Chemical compound CC1=CC=NC=C1C1=CSC(C=2C=CC(=CC=2)C(N)=O)=N1 VBZPQGUCYLDFNX-UHFFFAOYSA-N 0.000 description 2
ITQCLMBQTMJPFA-UHFFFAOYSA-N 4-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=CC=NC=C1C1=CSC(C=2C=CC(=CC=2)S(N)(=O)=O)=N1 ITQCLMBQTMJPFA-UHFFFAOYSA-N 0.000 description 2
PVMNPAUTCMBOMO-UHFFFAOYSA-N 4-chloropyridine Chemical compound ClC1=CC=NC=C1 PVMNPAUTCMBOMO-UHFFFAOYSA-N 0.000 description 2
LCASNSXTYOAJJP-UHFFFAOYSA-N 4-fluoro-n-methyl-3-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]benzamide Chemical compound CNC(=O)C1=CC=C(F)C(C=2SC=C(N=2)C=2C(=CC=NC=2)C)=C1 LCASNSXTYOAJJP-UHFFFAOYSA-N 0.000 description 2
IPVKCSWBEAVSRO-UHFFFAOYSA-N 4-propan-2-ylpyridine-3-carbonitrile Chemical compound CC(C)C1=CC=NC=C1C#N IPVKCSWBEAVSRO-UHFFFAOYSA-N 0.000 description 2
HELROTSKXOWDJY-UHFFFAOYSA-N 4-sulfamoylbenzenecarbothioamide Chemical compound NC(=S)C1=CC=C(S(N)(=O)=O)C=C1 HELROTSKXOWDJY-UHFFFAOYSA-N 0.000 description 2
UEHAHARCXMOIRL-UHFFFAOYSA-N 5-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-2-ethylpyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(CC)=NC=C1C1=NC(C=2C=CC(Cl)=CC=2)=CS1 UEHAHARCXMOIRL-UHFFFAOYSA-N 0.000 description 2
IKSMGTYGGQKDKD-UHFFFAOYSA-N 5-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]-1H-pyridin-2-one Chemical compound CC1=CC=NC=C1C1=CSC(C2=CNC(=O)C=C2)=N1 IKSMGTYGGQKDKD-UHFFFAOYSA-N 0.000 description 2
KWFUGHGRTCMSCP-UHFFFAOYSA-N 5-chloro-4-(4-chlorophenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=CC(Cl)=CC=2)=C(Cl)S1 KWFUGHGRTCMSCP-UHFFFAOYSA-N 0.000 description 2
GKSVAEZBWORXFB-UHFFFAOYSA-N 5-cyano-n-ethylpyridine-3-carboxamide Chemical compound CCNC(=O)C1=CN=CC(C#N)=C1 GKSVAEZBWORXFB-UHFFFAOYSA-N 0.000 description 2
FSUIAQRATUPVKE-UHFFFAOYSA-N 5-fluoro-4-(4-methylphenyl)-2-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound C1=CC(C)=CC=C1C1=C(F)SC(C=2C(=CC=NC=2)C)=N1 FSUIAQRATUPVKE-UHFFFAOYSA-N 0.000 description 2
BQRIHOKZPGJPDC-UHFFFAOYSA-N 6-[(2-methylpropan-2-yl)oxy]pyridine-3-carbonitrile Chemical compound CC(C)(C)OC1=CC=C(C#N)C=N1 BQRIHOKZPGJPDC-UHFFFAOYSA-N 0.000 description 2
BGJQWEULVOLEIN-UHFFFAOYSA-N 6-[(2-methylpropan-2-yl)oxy]pyridine-3-carbothioamide Chemical compound CC(C)(C)OC1=CC=C(C(N)=S)C=N1 BGJQWEULVOLEIN-UHFFFAOYSA-N 0.000 description 2
WLSMWRGZOZRSOI-UHFFFAOYSA-N 6-cyano-n-methylpyridine-3-carboxamide Chemical compound CNC(=O)C1=CC=C(C#N)N=C1 WLSMWRGZOZRSOI-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical class CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-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
206010006187 Breast cancer Diseases 0.000 description 2
208000026310 Breast neoplasm Diseases 0.000 description 2
108010037003 Buserelin Proteins 0.000 description 2
PYMDEDHDQYLBRT-DRIHCAFSSA-N Buserelin acetate Chemical compound CC(O)=O.CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](COC(C)(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 PYMDEDHDQYLBRT-DRIHCAFSSA-N 0.000 description 2
ZYUZLEUJKZZXNN-UHFFFAOYSA-N C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 Chemical group C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 ZYUZLEUJKZZXNN-UHFFFAOYSA-N 0.000 description 2
125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 description 2
HROIOYANRWEQRN-UHFFFAOYSA-N CC1=C(C=NC=C1)C(=O)C(C(C)C)Br.Br Chemical compound CC1=C(C=NC=C1)C(=O)C(C(C)C)Br.Br HROIOYANRWEQRN-UHFFFAOYSA-N 0.000 description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
102000007644 Colony-Stimulating Factors Human genes 0.000 description 2
108010071942 Colony-Stimulating Factors Proteins 0.000 description 2
UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 2
108010081668 Cytochrome P-450 CYP3A Proteins 0.000 description 2
102100039205 Cytochrome P450 3A4 Human genes 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
102000003972 Fibroblast growth factor 7 Human genes 0.000 description 2
108090000385 Fibroblast growth factor 7 Proteins 0.000 description 2
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
108010069236 Goserelin Proteins 0.000 description 2
102000003745 Hepatocyte Growth Factor Human genes 0.000 description 2
108090000100 Hepatocyte Growth Factor Proteins 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
102000004877 Insulin Human genes 0.000 description 2
108090001061 Insulin Proteins 0.000 description 2
102100020873 Interleukin-2 Human genes 0.000 description 2
108010002350 Interleukin-2 Proteins 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
206010027476 Metastases Diseases 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 2
JBFWAXPKTNPQKJ-UHFFFAOYSA-N N-[3-[2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazol-4-yl]phenyl]methanesulfonamide hydrochloride Chemical compound CS(=O)(=O)NC1=CC=CC(=C1)C2=CSC(=N2)C3=C(C=CN=C3)C(F)(F)F.Cl JBFWAXPKTNPQKJ-UHFFFAOYSA-N 0.000 description 2
108010025020 Nerve Growth Factor Proteins 0.000 description 2
102000015336 Nerve Growth Factor Human genes 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
108010038512 Platelet-Derived Growth Factor Proteins 0.000 description 2
102000010780 Platelet-Derived Growth Factor Human genes 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
229920002125 Sokalan® Polymers 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
102000004887 Transforming Growth Factor beta Human genes 0.000 description 2
108090001012 Transforming Growth Factor beta Proteins 0.000 description 2
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
208000002495 Uterine Neoplasms Diseases 0.000 description 2
108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 2
102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 2
108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 2
AIWRTTMUVOZGPW-HSPKUQOVSA-N abarelix Chemical compound C([C@@H](C(=O)N[C@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)N(C)C(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 AIWRTTMUVOZGPW-HSPKUQOVSA-N 0.000 description 2
229960002184 abarelix Drugs 0.000 description 2
108010023617 abarelix Proteins 0.000 description 2
150000001242 acetic acid derivatives Chemical class 0.000 description 2
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 2
RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
230000002411 adverse Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
229930013930 alkaloid Natural products 0.000 description 2
150000003797 alkaloid derivatives Chemical class 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
206010068168 androgenetic alopecia Diseases 0.000 description 2
229940094957 androgens and estrogen Drugs 0.000 description 2
AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 description 2
229960005471 androstenedione Drugs 0.000 description 2
AEMFNILZOJDQLW-UHFFFAOYSA-N androstenedione Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 AEMFNILZOJDQLW-UHFFFAOYSA-N 0.000 description 2
230000000340 anti-metabolite Effects 0.000 description 2
229940100197 antimetabolite Drugs 0.000 description 2
239000002256 antimetabolite Substances 0.000 description 2
239000003972 antineoplastic antibiotic Substances 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
235000006708 antioxidants Nutrition 0.000 description 2
125000004657 aryl sulfonyl amino group Chemical group 0.000 description 2
125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 description 2
159000000009 barium salts Chemical class 0.000 description 2
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
239000000872 buffer Substances 0.000 description 2
229960005064 buserelin acetate Drugs 0.000 description 2
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
KVUAALJSMIVURS-ZEDZUCNESA-L calcium folinate Chemical compound [Ca+2].C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC([O-])=O)C([O-])=O)C=C1 KVUAALJSMIVURS-ZEDZUCNESA-L 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
239000002775 capsule Substances 0.000 description 2
229910002091 carbon monoxide Inorganic materials 0.000 description 2
238000003763 carbonization Methods 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
229940105329 carboxymethylcellulose Drugs 0.000 description 2
229940084030 carboxymethylcellulose calcium Drugs 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
SBNPWPIBESPSIF-MHWMIDJBSA-N cetrorelix Chemical compound C([C@@H](C(=O)N[C@H](CCCNC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 SBNPWPIBESPSIF-MHWMIDJBSA-N 0.000 description 2
108700008462 cetrorelix Proteins 0.000 description 2
229960003230 cetrorelix Drugs 0.000 description 2
238000002512 chemotherapy Methods 0.000 description 2
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
235000012000 cholesterol Nutrition 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
229940125773 compound 10 Drugs 0.000 description 2
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
235000005687 corn oil Nutrition 0.000 description 2
239000002285 corn oil Substances 0.000 description 2
235000012343 cottonseed oil Nutrition 0.000 description 2
239000002385 cottonseed oil Substances 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
125000006638 cyclopentyl carbonyl group Chemical group 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 description 2
229960000684 cytarabine Drugs 0.000 description 2
PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
229940043279 diisopropylamine Drugs 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
OZWSHPFNEYQJSN-UHFFFAOYSA-N ethyl 3-(2-bromoacetyl)benzoate Chemical compound CCOC(=O)C1=CC=CC(C(=O)CBr)=C1 OZWSHPFNEYQJSN-UHFFFAOYSA-N 0.000 description 2
KHTGDCLCPJJWEY-UHFFFAOYSA-N ethyl 3-acetylbenzoate Chemical compound CCOC(=O)C1=CC=CC(C(C)=O)=C1 KHTGDCLCPJJWEY-UHFFFAOYSA-N 0.000 description 2
230000005713 exacerbation Effects 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
IAWCIZWLKMTPLL-UHFFFAOYSA-N fluoroethyne Chemical compound FC#C IAWCIZWLKMTPLL-UHFFFAOYSA-N 0.000 description 2
229960002949 fluorouracil Drugs 0.000 description 2
238000004508 fractional distillation Methods 0.000 description 2
GJNXBNATEDXMAK-PFLSVRRQSA-N ganirelix Chemical compound C([C@@H](C(=O)N[C@H](CCCCN=C(NCC)NCC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN=C(NCC)NCC)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 GJNXBNATEDXMAK-PFLSVRRQSA-N 0.000 description 2
108700032141 ganirelix Proteins 0.000 description 2
229960003794 ganirelix Drugs 0.000 description 2
210000004211 gastric acid Anatomy 0.000 description 2
229960003690 goserelin acetate Drugs 0.000 description 2
239000008187 granular material Substances 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
230000026030 halogenation Effects 0.000 description 2
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
239000001863 hydroxypropyl cellulose Substances 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
229940125396 insulin Drugs 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
229940011051 isopropyl acetate Drugs 0.000 description 2
HLWSLJSWUSSKDL-UHFFFAOYSA-N isoquinoline-1-carbothioamide Chemical compound C1=CC=C2C(C(=S)N)=NC=CC2=C1 HLWSLJSWUSSKDL-UHFFFAOYSA-N 0.000 description 2
YBAUGXZHOUTHEM-UHFFFAOYSA-N isoquinoline-3-carbothioamide Chemical compound C1=CC=C2C=NC(C(=S)N)=CC2=C1 YBAUGXZHOUTHEM-UHFFFAOYSA-N 0.000 description 2
GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 2
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
150000002576 ketones Chemical group 0.000 description 2
GFIJNRVAKGFPGQ-LIJARHBVSA-N leuprolide Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 GFIJNRVAKGFPGQ-LIJARHBVSA-N 0.000 description 2
229960004338 leuprorelin Drugs 0.000 description 2
239000007788 liquid Substances 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
159000000003 magnesium salts Chemical class 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
229960004961 mechlorethamine Drugs 0.000 description 2
HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical class ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
230000009401 metastasis Effects 0.000 description 2
JHHMSRLTZAUMOJ-UHFFFAOYSA-N methanamine;oxolane Chemical compound NC.C1CCOC1 JHHMSRLTZAUMOJ-UHFFFAOYSA-N 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 2
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 2
PUQAQLOALYNWTJ-UHFFFAOYSA-N n,4-dimethyl-3-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]benzamide Chemical compound CNC(=O)C1=CC=C(C)C(C=2SC=C(N=2)C=2C(=CC=NC=2)C)=C1 PUQAQLOALYNWTJ-UHFFFAOYSA-N 0.000 description 2
HTTFZXCFHHAPTC-UHFFFAOYSA-N n,n,4-trimethyl-3-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]benzamide Chemical compound CN(C)C(=O)C1=CC=C(C)C(C=2SC=C(N=2)C=2C(=CC=NC=2)C)=C1 HTTFZXCFHHAPTC-UHFFFAOYSA-N 0.000 description 2
GMHGUBWLFHZQSQ-UHFFFAOYSA-N n,n-dimethyl-3-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]benzamide Chemical compound CN(C)C(=O)C1=CC=CC(C=2SC=C(N=2)C=2C(=CC=NC=2)C)=C1 GMHGUBWLFHZQSQ-UHFFFAOYSA-N 0.000 description 2
UFKRTEWFEYWIHD-UHFFFAOYSA-N n-(4-cyanophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C#N)C=C1 UFKRTEWFEYWIHD-UHFFFAOYSA-N 0.000 description 2
BLCLNMBMMGCOAS-UHFFFAOYSA-N n-[1-[[1-[[1-[[1-[[1-[[1-[[1-[2-[(carbamoylamino)carbamoyl]pyrrolidin-1-yl]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amin Chemical compound C1CCC(C(=O)NNC(N)=O)N1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)C(COC(C)(C)C)NC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 BLCLNMBMMGCOAS-UHFFFAOYSA-N 0.000 description 2
HLYCSCJDWZNHTK-UHFFFAOYSA-N n-[3-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2SC=C(N=2)C=2C(=CC=NC=2)C)=C1 HLYCSCJDWZNHTK-UHFFFAOYSA-N 0.000 description 2
JBTIDVMWWZPFPP-UHFFFAOYSA-N n-[4-[2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazol-4-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CSC(C=2C(=CC=NC=2)C(F)(F)F)=N1 JBTIDVMWWZPFPP-UHFFFAOYSA-N 0.000 description 2
FBNQNOUYNNPGMW-UHFFFAOYSA-N n-[4-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=NC(C=2C(=CC=NC=2)C)=CS1 FBNQNOUYNNPGMW-UHFFFAOYSA-N 0.000 description 2
JWWGSFXKOLFWNB-UHFFFAOYSA-N n-methyl-3-[2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]benzamide Chemical compound CNC(=O)C1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C)=C1 JWWGSFXKOLFWNB-UHFFFAOYSA-N 0.000 description 2
UEZMWIDXCLEGMQ-UHFFFAOYSA-N n-methyl-3-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]benzamide Chemical compound CNC(=O)C1=CC=CC(C=2SC=C(N=2)C=2C(=CC=NC=2)C)=C1 UEZMWIDXCLEGMQ-UHFFFAOYSA-N 0.000 description 2
JYTSWYCUTBJYRG-UHFFFAOYSA-N n-methyl-4-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]benzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=NC(C=2C(=CC=NC=2)C)=CS1 JYTSWYCUTBJYRG-UHFFFAOYSA-N 0.000 description 2
XZZPJUAXYPMOOG-UHFFFAOYSA-N n-methyl-6-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]pyridine-2-carboxamide Chemical compound CNC(=O)C1=CC=CC(C=2SC=C(N=2)C=2C(=CC=NC=2)C)=N1 XZZPJUAXYPMOOG-UHFFFAOYSA-N 0.000 description 2
229920001206 natural gum Polymers 0.000 description 2
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
229940053128 nerve growth factor Drugs 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
125000006678 phenoxycarbonyl group Chemical group 0.000 description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
230000004962 physiological condition Effects 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
108010001062 polysaccharide-K Proteins 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
230000002335 preservative effect Effects 0.000 description 2
108090000765 processed proteins & peptides Proteins 0.000 description 2
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
238000000746 purification Methods 0.000 description 2
HYKQYVSNFPWGKQ-UHFFFAOYSA-N pyridine-2-carbothioamide Chemical compound NC(=S)C1=CC=CC=N1 HYKQYVSNFPWGKQ-UHFFFAOYSA-N 0.000 description 2
229940044601 receptor agonist Drugs 0.000 description 2
239000000018 receptor agonist Substances 0.000 description 2
229940044551 receptor antagonist Drugs 0.000 description 2
239000002464 receptor antagonist Substances 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
KUJFKFWQVGCSAR-UHFFFAOYSA-M sodium;ethyl acetate;hydrogen carbonate Chemical compound [Na+].OC([O-])=O.CCOC(C)=O KUJFKFWQVGCSAR-UHFFFAOYSA-M 0.000 description 2
238000000638 solvent extraction Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
229950009390 symclosene Drugs 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
210000001550 testis Anatomy 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 2
239000002562 thickening agent Substances 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
238000012546 transfer Methods 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 description 2
206010046766 uterine cancer Diseases 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
GNLJBJNONOOOQC-UHFFFAOYSA-N $l^{3}-carbane;magnesium Chemical compound [Mg]C GNLJBJNONOOOQC-UHFFFAOYSA-N 0.000 description 1
ILFPCMXTASDZKM-YFKPBYRVSA-N (1s)-2-methylidene-3-oxocyclopentane-1-carboxylic acid Chemical compound OC(=O)[C@H]1CCC(=O)C1=C ILFPCMXTASDZKM-YFKPBYRVSA-N 0.000 description 1
WDQLRUYAYXDIFW-RWKIJVEZSA-N (2r,3r,4s,5r,6r)-4-[(2s,3r,4s,5r,6r)-3,5-dihydroxy-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol Chemical compound O[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1 WDQLRUYAYXDIFW-RWKIJVEZSA-N 0.000 description 1
NAALWFYYHHJEFQ-ZASNTINBSA-N (2s,5r,6r)-6-[[(2r)-2-[[6-[4-[bis(2-hydroxyethyl)sulfamoyl]phenyl]-2-oxo-1h-pyridine-3-carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@@H](C(=O)N[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C=1C=CC(O)=CC=1)C(=O)C(C(N1)=O)=CC=C1C1=CC=C(S(=O)(=O)N(CCO)CCO)C=C1 NAALWFYYHHJEFQ-ZASNTINBSA-N 0.000 description 1
ZPHYPKKFSHAVOE-YZIXBPQXSA-N (7s,9s)-7-[(2r,4s,5s,6s)-4-amino-6-methyl-5-[(2r)-oxan-2-yl]oxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride Chemical compound Cl.O([C@H]1[C@@H](N)C[C@@H](O[C@H]1C)O[C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@@H]1CCCCO1 ZPHYPKKFSHAVOE-YZIXBPQXSA-N 0.000 description 1
FPVKHBSQESCIEP-UHFFFAOYSA-N (8S)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol Natural products C1C(O)C(CO)OC1N1C(NC=NCC2O)=C2N=C1 FPVKHBSQESCIEP-UHFFFAOYSA-N 0.000 description 1
FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 description 1
LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical class C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 1
IUOVOJHLRFQQNS-UHFFFAOYSA-N 1-(2-chloroethyl)-3-(2-methylsulfonylethyl)-1-nitrosourea Chemical compound CS(=O)(=O)CCNC(=O)N(N=O)CCCl IUOVOJHLRFQQNS-UHFFFAOYSA-N 0.000 description 1
SZDWTGAORQQQGY-UHFFFAOYSA-N 1-(3-bromo-4-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(F)C(Br)=C1 SZDWTGAORQQQGY-UHFFFAOYSA-N 0.000 description 1
JYAQYXOVOHJRCS-UHFFFAOYSA-N 1-(3-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(Br)=C1 JYAQYXOVOHJRCS-UHFFFAOYSA-N 0.000 description 1
KJQMDQDQXJDXJR-UHFFFAOYSA-N 1-(4-pentoxyphenyl)ethanone Chemical compound CCCCCOC1=CC=C(C(C)=O)C=C1 KJQMDQDQXJDXJR-UHFFFAOYSA-N 0.000 description 1
FGNXOQIMDXTCQJ-UHFFFAOYSA-N 1-(4-propan-2-ylpyridin-3-yl)ethanone Chemical compound CC(C)C1=CC=NC=C1C(C)=O FGNXOQIMDXTCQJ-UHFFFAOYSA-N 0.000 description 1
102100025573 1-alkyl-2-acetylglycerophosphocholine esterase Human genes 0.000 description 1
125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 1
BEUNOHDSYZHSFZ-UHFFFAOYSA-N 1-oxo-2,3-dihydroisoindole-4-carbonitrile Chemical compound C1=CC=C(C#N)C2=C1C(=O)NC2 BEUNOHDSYZHSFZ-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
DBPWSSGDRRHUNT-UHFFFAOYSA-N 17alpha-hydroxy progesterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(=O)C)(O)C1(C)CC2 DBPWSSGDRRHUNT-UHFFFAOYSA-N 0.000 description 1
DBPWSSGDRRHUNT-CEGNMAFCSA-N 17α-hydroxyprogesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)C)(O)[C@@]1(C)CC2 DBPWSSGDRRHUNT-CEGNMAFCSA-N 0.000 description 1
HYZJCKYKOHLVJF-SFIIULIVSA-N 1H-benzimidazole Chemical class C1=CC=C2N[11CH]=NC2=C1 HYZJCKYKOHLVJF-SFIIULIVSA-N 0.000 description 1
MUECGDALHJLKPK-UHFFFAOYSA-N 2,4-bis(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C(=CC=NC=2)C)=N1 MUECGDALHJLKPK-UHFFFAOYSA-N 0.000 description 1
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
LSPMHHJCDSFAAY-UHFFFAOYSA-N 2,6-dichloro-4-methylpyridine-3-carbonitrile Chemical compound CC1=CC(Cl)=NC(Cl)=C1C#N LSPMHHJCDSFAAY-UHFFFAOYSA-N 0.000 description 1
ZZIZZTHXZRDOFM-UHFFFAOYSA-N 2-(2-ethoxyphenoxy)ethyl-[1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl]azanium;chloride Chemical compound Cl.CCOC1=CC=CC=C1OCCNC(C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 ZZIZZTHXZRDOFM-UHFFFAOYSA-N 0.000 description 1
CUAQQLFEQMUZHF-UHFFFAOYSA-N 2-(4-chlorophenyl)acetyl bromide Chemical compound ClC1=CC=C(CC(Br)=O)C=C1 CUAQQLFEQMUZHF-UHFFFAOYSA-N 0.000 description 1
KHWCCUNYDRVVCI-UHFFFAOYSA-N 2-(4-methylpyridin-3-yl)-4-pyridin-4-yl-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=NC(C=2C=CN=CC=2)=CS1 KHWCCUNYDRVVCI-UHFFFAOYSA-N 0.000 description 1
YGZFYDFBHIDIBH-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]icosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCC(CO)N(CCO)CCO YGZFYDFBHIDIBH-UHFFFAOYSA-N 0.000 description 1
QCXJFISCRQIYID-IAEPZHFASA-N 2-amino-1-n-[(3s,6s,7r,10s,16s)-3-[(2s)-butan-2-yl]-7,11,14-trimethyl-2,5,9,12,15-pentaoxo-10-propan-2-yl-8-oxa-1,4,11,14-tetrazabicyclo[14.3.0]nonadecan-6-yl]-4,6-dimethyl-3-oxo-9-n-[(3s,6s,7r,10s,16s)-7,11,14-trimethyl-2,5,9,12,15-pentaoxo-3,10-di(propa Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N=C2C(C(=O)N[C@@H]3C(=O)N[C@H](C(N4CCC[C@H]4C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]3C)=O)[C@@H](C)CC)=C(N)C(=O)C(C)=C2O2)C2=C(C)C=C1 QCXJFISCRQIYID-IAEPZHFASA-N 0.000 description 1
RGALBQILADNMKA-UHFFFAOYSA-N 2-bromo-1-pyridin-4-ylethanone;hydron;bromide Chemical compound Br.BrCC(=O)C1=CC=NC=C1 RGALBQILADNMKA-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 1
LQIGDRSXHXULND-UHFFFAOYSA-N 2-fluoro-5-[2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazol-4-yl]benzamide Chemical compound C1=C(F)C(C(=O)N)=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C(F)(F)F)=C1 LQIGDRSXHXULND-UHFFFAOYSA-N 0.000 description 1
MGCFPFIUDMCYFV-UHFFFAOYSA-N 2-fluoro-n,n-dimethyl-5-[2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazol-4-yl]benzamide Chemical compound C1=C(F)C(C(=O)N(C)C)=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C(F)(F)F)=C1 MGCFPFIUDMCYFV-UHFFFAOYSA-N 0.000 description 1
HNDNAIHVGGBJAZ-UHFFFAOYSA-N 2-fluoro-n-methyl-5-[2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazol-4-yl]benzamide Chemical compound C1=C(F)C(C(=O)NC)=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C(F)(F)F)=C1 HNDNAIHVGGBJAZ-UHFFFAOYSA-N 0.000 description 1
ZKPSAKATYCTKLC-UHFFFAOYSA-N 2-isoquinolin-1-yl-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2C3=CC=CC=C3C=CN=2)=N1 ZKPSAKATYCTKLC-UHFFFAOYSA-N 0.000 description 1
PAJJRJRONSSRTF-UHFFFAOYSA-N 2-isoquinolin-3-yl-4-(4-methylpyridin-3-yl)-1,3-thiazole Chemical compound CC1=CC=NC=C1C1=CSC(C=2N=CC3=CC=CC=C3C=2)=N1 PAJJRJRONSSRTF-UHFFFAOYSA-N 0.000 description 1
YGJCEJBWMDPCQY-UHFFFAOYSA-N 2-methyl-1-oxo-3h-isoindole-4-carbonitrile Chemical compound O=C1N(C)CC2=C1C=CC=C2C#N YGJCEJBWMDPCQY-UHFFFAOYSA-N 0.000 description 1
IQRJWXUKGVQAQC-UHFFFAOYSA-N 2-methyl-1-oxo-3h-isoindole-4-carbothioamide Chemical compound O=C1N(C)CC2=C1C=CC=C2C(N)=S IQRJWXUKGVQAQC-UHFFFAOYSA-N 0.000 description 1
125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
JHMBTUMIVBSJFS-UHFFFAOYSA-N 2-methyl-3h-isoindol-1-one Chemical compound C1=CC=C2C(=O)N(C)CC2=C1 JHMBTUMIVBSJFS-UHFFFAOYSA-N 0.000 description 1
YCRIMTYMYABPSX-UHFFFAOYSA-N 2-methyl-5-(pyrrolidine-1-carbonyl)benzonitrile Chemical compound C1=C(C#N)C(C)=CC=C1C(=O)N1CCCC1 YCRIMTYMYABPSX-UHFFFAOYSA-N 0.000 description 1
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
XOSDYLFXPMFRGF-UHFFFAOYSA-N 2-methyl-5-nitrobenzonitrile Chemical compound CC1=CC=C([N+]([O-])=O)C=C1C#N XOSDYLFXPMFRGF-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
AEDQNOLIADXSBB-UHFFFAOYSA-N 3-(dodecylazaniumyl)propanoate Chemical compound CCCCCCCCCCCCNCCC(O)=O AEDQNOLIADXSBB-UHFFFAOYSA-N 0.000 description 1
VYMIHYJMVWZJSV-UHFFFAOYSA-N 3-[2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]benzamide Chemical compound CC1=CC=NC=C1C1=NC(C=2C=C(C=CC=2)C(N)=O)=CS1 VYMIHYJMVWZJSV-UHFFFAOYSA-N 0.000 description 1
ZBIZAJBLEXMIHY-UHFFFAOYSA-N 3-[2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazol-4-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C(F)(F)F)=C1 ZBIZAJBLEXMIHY-UHFFFAOYSA-N 0.000 description 1
LVARJLNDAXWYQB-UHFFFAOYSA-N 3-[4-(4-ethylpyridin-3-yl)-1,3-thiazol-2-yl]-n,n-dimethylbenzamide Chemical compound CCC1=CC=NC=C1C1=CSC(C=2C=C(C=CC=2)C(=O)N(C)C)=N1 LVARJLNDAXWYQB-UHFFFAOYSA-N 0.000 description 1
PFJPSYKABQZSAV-UHFFFAOYSA-N 3-[4-(4-ethylpyridin-3-yl)-1,3-thiazol-2-yl]-n-methylbenzamide Chemical compound CCC1=CC=NC=C1C1=CSC(C=2C=C(C=CC=2)C(=O)NC)=N1 PFJPSYKABQZSAV-UHFFFAOYSA-N 0.000 description 1
CSEBHYBYCHDCOU-UHFFFAOYSA-N 3-[4-(4-ethylpyridin-3-yl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CCC1=CC=NC=C1C1=CSC(C=2C=C(C=CC=2)S(N)(=O)=O)=N1 CSEBHYBYCHDCOU-UHFFFAOYSA-N 0.000 description 1
UVEFYGYGTOWTLO-UHFFFAOYSA-N 3-[5-methyl-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC=1SC(C=2C=C(C=CC=2)S(N)(=O)=O)=NC=1C1=CN=CC=C1C UVEFYGYGTOWTLO-UHFFFAOYSA-N 0.000 description 1
WUIABRMSWOKTOF-OYALTWQYSA-N 3-[[2-[2-[2-[[(2s,3r)-2-[[(2s,3s,4r)-4-[[(2s,3r)-2-[[6-amino-2-[(1s)-3-amino-1-[[(2s)-2,3-diamino-3-oxopropyl]amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[(2r,3s,4s,5s,6s)-3-[(2r,3s,4s,5r,6r)-4-carbamoyloxy-3,5-dihydroxy-6-(hydroxymethyl)ox Chemical compound OS([O-])(=O)=O.N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1NC=NC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C WUIABRMSWOKTOF-OYALTWQYSA-N 0.000 description 1
HBTQVYZUOGVMQM-UHFFFAOYSA-N 3-acetylbenzonitrile;3-(2-bromoacetyl)benzonitrile Chemical compound CC(=O)C1=CC=CC(C#N)=C1.BrCC(=O)C1=CC=CC(C#N)=C1 HBTQVYZUOGVMQM-UHFFFAOYSA-N 0.000 description 1
XYFHGDQQIOYGME-UHFFFAOYSA-N 3-bromo-4-fluoro-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(F)C(Br)=C1 XYFHGDQQIOYGME-UHFFFAOYSA-N 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
KASZJRKMQMEDTD-UHFFFAOYSA-N 3-cyano-n,n,4-trimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=C(C)C(C#N)=C1 KASZJRKMQMEDTD-UHFFFAOYSA-N 0.000 description 1
CQUOVARNSKZJGM-UHFFFAOYSA-N 3-cyano-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC(C#N)=C1 CQUOVARNSKZJGM-UHFFFAOYSA-N 0.000 description 1
PAQVSWFCADWSLB-UHFFFAOYSA-N 3-cyanobenzamide Chemical compound NC(=O)C1=CC=CC(C#N)=C1 PAQVSWFCADWSLB-UHFFFAOYSA-N 0.000 description 1
XSDODZGLROXONP-UHFFFAOYSA-N 3-iodo-n,4-dimethylbenzamide Chemical compound CNC(=O)C1=CC=C(C)C(I)=C1 XSDODZGLROXONP-UHFFFAOYSA-N 0.000 description 1
QWBGSUFBFBZHGY-UHFFFAOYSA-N 3-iodo-n,4-dimethylbenzamide;3-iodo-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1I.CNC(=O)C1=CC=C(C)C(I)=C1 QWBGSUFBFBZHGY-UHFFFAOYSA-N 0.000 description 1
GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical class N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 1
LKQDFQLSEHWIRK-UKBVDAKRSA-N 3alpha,17alpha-Dihydroxy-5beta-pregnan-20-one Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@@](C(=O)C)(O)[C@@]2(C)CC1 LKQDFQLSEHWIRK-UKBVDAKRSA-N 0.000 description 1
AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 1
CLPFFLWZZBQMAO-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1N2C=NC=C2CCC1 CLPFFLWZZBQMAO-UHFFFAOYSA-N 0.000 description 1
FUTSYYIXHRXELM-UHFFFAOYSA-N 4-[4-(4-ethylpyridin-3-yl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CCC1=CC=NC=C1C1=CSC(C=2C=CC(=CC=2)S(N)(=O)=O)=N1 FUTSYYIXHRXELM-UHFFFAOYSA-N 0.000 description 1
ZHSKUOZOLHMKEA-UHFFFAOYSA-N 4-[5-[bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]butanoic acid;hydron;chloride Chemical compound Cl.ClCCN(CCCl)C1=CC=C2N(C)C(CCCC(O)=O)=NC2=C1 ZHSKUOZOLHMKEA-UHFFFAOYSA-N 0.000 description 1
PILHRVCMIQYQON-UHFFFAOYSA-N 4-[5-methyl-4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC=1SC(C=2C=CC(=CC=2)S(N)(=O)=O)=NC=1C1=CN=CC=C1C PILHRVCMIQYQON-UHFFFAOYSA-N 0.000 description 1
LFMCXLYALCONQB-UHFFFAOYSA-N 4-acetyl-n,n-dibenzylbenzenesulfonamide Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 LFMCXLYALCONQB-UHFFFAOYSA-N 0.000 description 1
ACPXHHDRVABPNY-UHFFFAOYSA-N 4-acetylbenzenesulfonic acid Chemical compound CC(=O)C1=CC=C(S(O)(=O)=O)C=C1 ACPXHHDRVABPNY-UHFFFAOYSA-N 0.000 description 1
YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 1
TVZGACDUOSZQKY-LBPRGKRZSA-N 4-aminofolic acid Chemical compound C1=NC2=NC(N)=NC(N)=C2N=C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 TVZGACDUOSZQKY-LBPRGKRZSA-N 0.000 description 1
UGGZWKXUBBYXLT-UHFFFAOYSA-N 4-cyano-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(C#N)C=C1 UGGZWKXUBBYXLT-UHFFFAOYSA-N 0.000 description 1
FUKWTMJZHKZKFA-UHFFFAOYSA-N 4-cyanobenzamide Chemical compound NC(=O)C1=CC=C(C#N)C=C1 FUKWTMJZHKZKFA-UHFFFAOYSA-N 0.000 description 1
USEDMAWWQDFMFY-UHFFFAOYSA-N 4-cyanobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(C#N)C=C1 USEDMAWWQDFMFY-UHFFFAOYSA-N 0.000 description 1
239000002677 5-alpha reductase inhibitor Substances 0.000 description 1
QEZIMQMMEGPYTR-UHFFFAOYSA-N 5-bromo-2,4-dimethoxypyrimidine Chemical compound COC1=NC=C(Br)C(OC)=N1 QEZIMQMMEGPYTR-UHFFFAOYSA-N 0.000 description 1
JKYTZJSGPWNIRB-UHFFFAOYSA-N 5-bromo-2-chloro-n-methylbenzamide Chemical compound CNC(=O)C1=CC(Br)=CC=C1Cl JKYTZJSGPWNIRB-UHFFFAOYSA-N 0.000 description 1
LBNZQARQDQMTGO-UHFFFAOYSA-N 5-bromo-n-ethylpyridine-3-carboxamide Chemical compound CCNC(=O)C1=CN=CC(Br)=C1 LBNZQARQDQMTGO-UHFFFAOYSA-N 0.000 description 1
PCIALXZKUYAGLF-UHFFFAOYSA-N 5-bromopyridine-3-carboxamide 5-cyanopyridine-3-carboxamide Chemical compound BrC=1C=NC=C(C(=O)N)C1.C(#N)C=1C=NC=C(C(=O)N)C1 PCIALXZKUYAGLF-UHFFFAOYSA-N 0.000 description 1
XKTFHJIMJMIYLT-UHFFFAOYSA-N 5-cyano-n-methylpyridine-3-carboxamide Chemical compound CNC(=O)C1=CN=CC(C#N)=C1 XKTFHJIMJMIYLT-UHFFFAOYSA-N 0.000 description 1
XYXYWYBIPHEICF-UHFFFAOYSA-N 5-cyanopyridine-3-carboxamide Chemical compound NC(=O)C1=CN=CC(C#N)=C1 XYXYWYBIPHEICF-UHFFFAOYSA-N 0.000 description 1
WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 description 1
XHYGUDGTUJPSNX-UHFFFAOYSA-N 6-bromopyridine-3-carbonitrile Chemical compound BrC1=CC=C(C#N)C=N1 XHYGUDGTUJPSNX-UHFFFAOYSA-N 0.000 description 1
DEYOMDZKXMQLCF-UHFFFAOYSA-N 6-chloro-n-methylpyridine-3-carboxamide Chemical compound CNC(=O)C1=CC=C(Cl)N=C1 DEYOMDZKXMQLCF-UHFFFAOYSA-N 0.000 description 1
LWYGNKQBQWLYNW-UHFFFAOYSA-N 6-cyano-n-methylpyridine-2-carboxamide Chemical compound CNC(=O)C1=CC=CC(C#N)=N1 LWYGNKQBQWLYNW-UHFFFAOYSA-N 0.000 description 1
KAEVHZSIYLATMK-UHFFFAOYSA-N 6-n-[bis(aziridin-1-yl)phosphoryl]-2-n,2-n,7-trimethylpurine-2,6-diamine Chemical compound C=12N(C)C=NC2=NC(N(C)C)=NC=1NP(=O)(N1CC1)N1CC1 KAEVHZSIYLATMK-UHFFFAOYSA-N 0.000 description 1
NKGPJODWTZCHGF-KQYNXXCUSA-N 6-thioinosinic acid Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(S)=C2N=C1 NKGPJODWTZCHGF-KQYNXXCUSA-N 0.000 description 1
KABRXLINDSPGDF-UHFFFAOYSA-N 7-bromoisoquinoline Chemical compound C1=CN=CC2=CC(Br)=CC=C21 KABRXLINDSPGDF-UHFFFAOYSA-N 0.000 description 1
NKGPJODWTZCHGF-UHFFFAOYSA-N 9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound OC1C(O)C(CO)OC1N1C(NC=NC2=S)=C2N=C1 NKGPJODWTZCHGF-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
208000005641 Adenomyosis Diseases 0.000 description 1
ATXHVCQZZJYMCF-XUDSTZEESA-N Allylestrenol Chemical compound C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)CC=C)[C@@H]4[C@@H]3CCC2=C1 ATXHVCQZZJYMCF-XUDSTZEESA-N 0.000 description 1
229940127512 Androgen Synthesis Inhibitors Drugs 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 description 1
229940122815 Aromatase inhibitor Drugs 0.000 description 1
108010024976 Asparaginase Proteins 0.000 description 1
VGGGPCQERPFHOB-MCIONIFRSA-N Bestatin Chemical compound CC(C)C[C@H](C(O)=O)NC(=O)[C@@H](O)[C@H](N)CC1=CC=CC=C1 VGGGPCQERPFHOB-MCIONIFRSA-N 0.000 description 1
108010006654 Bleomycin Proteins 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
RODIJDDGTYJYDP-UHFFFAOYSA-N BrC=1C=NC=C(C(=O)O)C1.BrC=1C=NC=C(C(=O)N)C1 Chemical compound BrC=1C=NC=C(C(=O)O)C1.BrC=1C=NC=C(C(=O)N)C1 RODIJDDGTYJYDP-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
SFHXCWBUSGCHPP-UHFFFAOYSA-N C(#N)C=1C=C(C(=O)O)C=CC1.C(#N)C=1C=C(C(=O)N(C)C)C=CC1 Chemical compound C(#N)C=1C=C(C(=O)O)C=CC1.C(#N)C=1C=C(C(=O)N(C)C)C=CC1 SFHXCWBUSGCHPP-UHFFFAOYSA-N 0.000 description 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
UJKPHYRXOLRVJJ-MLSVHJFASA-N CC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4C(C)O)/C(CCC(O)=O)=C3C Chemical compound CC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4C(C)O)/C(CCC(O)=O)=C3C UJKPHYRXOLRVJJ-MLSVHJFASA-N 0.000 description 1
KSFOVUSSGSKXFI-GAQDCDSVSA-N CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O Chemical compound CC1=C/2NC(\C=C3/N=C(/C=C4\N\C(=C/C5=N/C(=C\2)/C(C=C)=C5C)C(C=C)=C4C)C(C)=C3CCC(O)=O)=C1CCC(O)=O KSFOVUSSGSKXFI-GAQDCDSVSA-N 0.000 description 1
206010006895 Cachexia Diseases 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 1
102000053642 Catalytic RNA Human genes 0.000 description 1
108090000994 Catalytic RNA Proteins 0.000 description 1
241000282693 Cercopithecidae Species 0.000 description 1
JWBOIMRXGHLCPP-UHFFFAOYSA-N Chloditan Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)Cl)C1=CC=C(Cl)C=C1 JWBOIMRXGHLCPP-UHFFFAOYSA-N 0.000 description 1
QMBJSIBWORFWQT-DFXBJWIESA-N Chlormadinone acetate Chemical compound C1=C(Cl)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 QMBJSIBWORFWQT-DFXBJWIESA-N 0.000 description 1
RURLVUZRUFHCJO-UHFFFAOYSA-N Chromomycin A3 Natural products COC(C1Cc2cc3cc(OC4CC(OC(=O)C)C(OC5CC(O)C(OC)C(C)O5)C(C)O4)c(C)c(O)c3c(O)c2C(=O)C1OC6CC(OC7CC(C)(O)C(OC(=O)C)C(C)O7)C(O)C(C)O6)C(=O)C(O)C(C)O RURLVUZRUFHCJO-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 description 1
101000904177 Clupea pallasii Gonadoliberin-1 Proteins 0.000 description 1
241000595586 Coryne Species 0.000 description 1
229920002785 Croscarmellose sodium Polymers 0.000 description 1
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
229940123780 DNA topoisomerase I inhibitor Drugs 0.000 description 1
229940124087 DNA topoisomerase II inhibitor Drugs 0.000 description 1
108010092160 Dactinomycin Proteins 0.000 description 1
239000004287 Dehydroacetic acid Substances 0.000 description 1
FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
MWWSFMDVAYGXBV-RUELKSSGSA-N Doxorubicin hydrochloride Chemical compound Cl.O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 MWWSFMDVAYGXBV-RUELKSSGSA-N 0.000 description 1
HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 description 1
OBMLHUPNRURLOK-XGRAFVIBSA-N Epitiostanol Chemical compound C1[C@@H]2S[C@@H]2C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 OBMLHUPNRURLOK-XGRAFVIBSA-N 0.000 description 1
VAPSMQAHNAZRKC-PQWRYPMOSA-N Epristeride Chemical compound C1C=C2C=C(C(O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)NC(C)(C)C)[C@@]1(C)CC2 VAPSMQAHNAZRKC-PQWRYPMOSA-N 0.000 description 1
241000283086 Equidae Species 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
108091008794 FGF receptors Proteins 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
102000044168 Fibroblast Growth Factor Receptor Human genes 0.000 description 1
108090001047 Fibroblast growth factor 10 Proteins 0.000 description 1
102100028412 Fibroblast growth factor 10 Human genes 0.000 description 1
BJJXHLWLUDYTGC-ANULTFPQSA-N Gestrinone Chemical compound C1CC(=O)C=C2CC[C@@H]([C@H]3[C@@](CC)([C@](CC3)(O)C#C)C=C3)C3=C21 BJJXHLWLUDYTGC-ANULTFPQSA-N 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
239000000579 Gonadotropin-Releasing Hormone Substances 0.000 description 1
102000004269 Granulocyte Colony-Stimulating Factor Human genes 0.000 description 1
108010017080 Granulocyte Colony-Stimulating Factor Proteins 0.000 description 1
102000009465 Growth Factor Receptors Human genes 0.000 description 1
108010009202 Growth Factor Receptors Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
241000282412 Homo Species 0.000 description 1
101000904173 Homo sapiens Progonadoliberin-1 Proteins 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 1
206010020843 Hyperthermia Diseases 0.000 description 1
XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 description 1
108010001127 Insulin Receptor Proteins 0.000 description 1
102100036721 Insulin receptor Human genes 0.000 description 1
102000048143 Insulin-Like Growth Factor II Human genes 0.000 description 1
108090001117 Insulin-Like Growth Factor II Proteins 0.000 description 1
102000014150 Interferons Human genes 0.000 description 1
108010050904 Interferons Proteins 0.000 description 1
102000015696 Interleukins Human genes 0.000 description 1
108010063738 Interleukins Proteins 0.000 description 1
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
239000005411 L01XE02 - Gefitinib Substances 0.000 description 1
229920001491 Lentinan Polymers 0.000 description 1
HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 1
102000004083 Lymphotoxin-alpha Human genes 0.000 description 1
108090000542 Lymphotoxin-alpha Proteins 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
102000007651 Macrophage Colony-Stimulating Factor Human genes 0.000 description 1
108010046938 Macrophage Colony-Stimulating Factor Proteins 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
206010033128 Ovarian cancer Diseases 0.000 description 1
206010061535 Ovarian neoplasm Diseases 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
229930012538 Paclitaxel Natural products 0.000 description 1
108010057150 Peplomycin Proteins 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
HFVNWDWLWUCIHC-GUPDPFMOSA-N Prednimustine Chemical compound O=C([C@@]1(O)CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)[C@@H](O)C[C@@]21C)COC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 HFVNWDWLWUCIHC-GUPDPFMOSA-N 0.000 description 1
102100024028 Progonadoliberin-1 Human genes 0.000 description 1
AHHFEZNOXOZZQA-ZEBDFXRSSA-N Ranimustine Chemical compound CO[C@H]1O[C@H](CNC(=O)N(CCCl)N=O)[C@@H](O)[C@H](O)[C@H]1O AHHFEZNOXOZZQA-ZEBDFXRSSA-N 0.000 description 1
229920002305 Schizophyllan Polymers 0.000 description 1
OCOKWVBYZHBHLU-UHFFFAOYSA-N Sobuzoxane Chemical compound C1C(=O)N(COC(=O)OCC(C)C)C(=O)CN1CCN1CC(=O)N(COC(=O)OCC(C)C)C(=O)C1 OCOKWVBYZHBHLU-UHFFFAOYSA-N 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
101000857870 Squalus acanthias Gonadoliberin Proteins 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
101000996723 Sus scrofa Gonadotropin-releasing hormone receptor Proteins 0.000 description 1
WFWLQNSHRPWKFK-UHFFFAOYSA-N Tegafur Chemical compound O=C1NC(=O)C(F)=CN1C1OCCC1 WFWLQNSHRPWKFK-UHFFFAOYSA-N 0.000 description 1
BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 description 1
244000299461 Theobroma cacao Species 0.000 description 1
235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 description 1
FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 description 1
239000000365 Topoisomerase I Inhibitor Substances 0.000 description 1
239000000317 Topoisomerase II Inhibitor Substances 0.000 description 1
IWEQQRMGNVVKQW-OQKDUQJOSA-N Toremifene citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 IWEQQRMGNVVKQW-OQKDUQJOSA-N 0.000 description 1
UMILHIMHKXVDGH-UHFFFAOYSA-N Triethylene glycol diglycidyl ether Chemical compound C1OC1COCCOCCOCCOCC1CO1 UMILHIMHKXVDGH-UHFFFAOYSA-N 0.000 description 1
JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 1
ZQMFXCKDNCYRSZ-UHFFFAOYSA-N [4-methyl-3-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]phenyl]-pyrrolidin-1-ylmethanone Chemical compound CC1=CC=NC=C1C1=CSC(C=2C(=CC=C(C=2)C(=O)N2CCCC2)C)=N1 ZQMFXCKDNCYRSZ-UHFFFAOYSA-N 0.000 description 1
HMOINYWJVRRUOK-UHFFFAOYSA-N [Mg].C(C)C1=C(C=NC=C1)C(C)=O Chemical compound [Mg].C(C)C1=C(C=NC=C1)C(C)=O HMOINYWJVRRUOK-UHFFFAOYSA-N 0.000 description 1
XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 1
GZOSMCIZMLWJML-VJLLXTKPSA-N abiraterone Chemical compound C([C@H]1[C@H]2[C@@H]([C@]3(CC[C@H](O)CC3=CC2)C)CC[C@@]11C)C=C1C1=CC=CN=C1 GZOSMCIZMLWJML-VJLLXTKPSA-N 0.000 description 1
229960000853 abiraterone Drugs 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
MNZMECMQTYGSOI-UHFFFAOYSA-N acetic acid;hydron;bromide Chemical compound Br.CC(O)=O MNZMECMQTYGSOI-UHFFFAOYSA-N 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
USZYSDMBJDPRIF-SVEJIMAYSA-N aclacinomycin A Chemical compound O([C@H]1[C@@H](O)C[C@@H](O[C@H]1C)O[C@H]1[C@H](C[C@@H](O[C@H]1C)O[C@H]1C[C@]([C@@H](C2=CC=3C(=O)C4=CC=CC(O)=C4C(=O)C=3C(O)=C21)C(=O)OC)(O)CC)N(C)C)[C@H]1CCC(=O)[C@H](C)O1 USZYSDMBJDPRIF-SVEJIMAYSA-N 0.000 description 1
229960004176 aclarubicin Drugs 0.000 description 1
RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
BYRVKDUQDLJUBX-JJCDCTGGSA-N adozelesin Chemical compound C1=CC=C2OC(C(=O)NC=3C=C4C=C(NC4=CC=3)C(=O)N3C[C@H]4C[C@]44C5=C(C(C=C43)=O)NC=C5C)=CC2=C1 BYRVKDUQDLJUBX-JJCDCTGGSA-N 0.000 description 1
229950004955 adozelesin Drugs 0.000 description 1
125000001980 alanyl group Chemical group 0.000 description 1
150000001340 alkali metals Chemical group 0.000 description 1
125000005115 alkyl carbamoyl group Chemical group 0.000 description 1
125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
229960002692 allylestrenol Drugs 0.000 description 1
239000002160 alpha blocker Substances 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
229940124308 alpha-adrenoreceptor antagonist Drugs 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229960000473 altretamine Drugs 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
ROBVIMPUHSLWNV-UHFFFAOYSA-N aminoglutethimide Chemical compound C=1C=C(N)C=CC=1C1(CC)CCC(=O)NC1=O ROBVIMPUHSLWNV-UHFFFAOYSA-N 0.000 description 1
229960003437 aminoglutethimide Drugs 0.000 description 1
229960003896 aminopterin Drugs 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
229960002932 anastrozole Drugs 0.000 description 1
YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 description 1
KZOWNALBTMILAP-JBMRGDGGSA-N ancitabine hydrochloride Chemical compound Cl.N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 KZOWNALBTMILAP-JBMRGDGGSA-N 0.000 description 1
229940121369 angiogenesis inhibitor Drugs 0.000 description 1
239000004037 angiogenesis inhibitor Substances 0.000 description 1
230000002280 anti-androgenic effect Effects 0.000 description 1
229940046836 anti-estrogen Drugs 0.000 description 1
230000001833 anti-estrogenic effect Effects 0.000 description 1
239000000051 antiandrogen Substances 0.000 description 1
229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
239000003886 aromatase inhibitor Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
JUCVMCNRABNRJD-UHFFFAOYSA-N azane;ethyl acetate Chemical compound N.CCOC(C)=O JUCVMCNRABNRJD-UHFFFAOYSA-N 0.000 description 1
KLNFSAOEKUDMFA-UHFFFAOYSA-N azanide;2-hydroxyacetic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OCC(O)=O KLNFSAOEKUDMFA-UHFFFAOYSA-N 0.000 description 1
VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
HGQULGDOROIPJN-UHFFFAOYSA-N azetidin-1-ium;chloride Chemical compound Cl.C1CNC1 HGQULGDOROIPJN-UHFFFAOYSA-N 0.000 description 1
SYCKNGJQFXKETE-UHFFFAOYSA-N azetidin-1-yl-[3-[2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]phenyl]methanone Chemical compound CC1=CC=NC=C1C1=NC(C=2C=C(C=CC=2)C(=O)N2CCC2)=CS1 SYCKNGJQFXKETE-UHFFFAOYSA-N 0.000 description 1
150000007980 azole derivatives Chemical class 0.000 description 1
229960000190 bacillus calmette–guérin vaccine Drugs 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
229960000686 benzalkonium chloride Drugs 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
229960001950 benzethonium chloride Drugs 0.000 description 1
150000008359 benzonitriles Chemical class 0.000 description 1
MMIMIFULGMZVPO-UHFFFAOYSA-N benzyl 3-bromo-2,6-dinitro-5-phenylmethoxybenzoate Chemical compound [O-][N+](=O)C1=C(C(=O)OCC=2C=CC=CC=2)C([N+](=O)[O-])=C(Br)C=C1OCC1=CC=CC=C1 MMIMIFULGMZVPO-UHFFFAOYSA-N 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
229960002903 benzyl benzoate Drugs 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
229960002537 betamethasone Drugs 0.000 description 1
UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 1
229960000997 bicalutamide Drugs 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 1
229960004395 bleomycin sulfate Drugs 0.000 description 1
ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
229960002092 busulfan Drugs 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
125000006251 butylcarbonyl group Chemical group 0.000 description 1
235000001046 cacaotero Nutrition 0.000 description 1
108700002839 cactinomycin Proteins 0.000 description 1
235000008207 calcium folinate Nutrition 0.000 description 1
239000011687 calcium folinate Substances 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
KVUAALJSMIVURS-QNTKWALQSA-L calcium;(2s)-2-[[4-[[(6s)-2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl]methylamino]benzoyl]amino]pentanedioate Chemical compound [Ca+2].C([C@@H]1N(C=O)C=2C(=O)N=C(NC=2NC1)N)NC1=CC=C(C(=O)N[C@@H](CCC([O-])=O)C([O-])=O)C=C1 KVUAALJSMIVURS-QNTKWALQSA-L 0.000 description 1
125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
229960004562 carboplatin Drugs 0.000 description 1
229960005243 carmustine Drugs 0.000 description 1
230000024245 cell differentiation Effects 0.000 description 1
230000004663 cell proliferation Effects 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
229960005395 cetuximab Drugs 0.000 description 1
229960001616 chlormadinone acetate Drugs 0.000 description 1
229960004926 chlorobutanol Drugs 0.000 description 1
ZYVSOIYQKUDENJ-WKSBCEQHSA-N chromomycin A3 Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@@H]1OC(C)=O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@@H](O)[C@H](O[C@@H]3O[C@@H](C)[C@H](OC(C)=O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@@H]1C[C@@H](O)[C@@H](OC)[C@@H](C)O1 ZYVSOIYQKUDENJ-WKSBCEQHSA-N 0.000 description 1
229960004316 cisplatin Drugs 0.000 description 1
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
229960002436 cladribine Drugs 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
150000004700 cobalt complex Chemical class 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
238000013329 compounding Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
229960001334 corticosteroids Drugs 0.000 description 1
229960001681 croscarmellose sodium Drugs 0.000 description 1
235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
229960004397 cyclophosphamide Drugs 0.000 description 1
UWFYSQMTEOIJJG-FDTZYFLXSA-N cyproterone acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 UWFYSQMTEOIJJG-FDTZYFLXSA-N 0.000 description 1
229960000978 cyproterone acetate Drugs 0.000 description 1
229960003901 dacarbazine Drugs 0.000 description 1
229960000640 dactinomycin Drugs 0.000 description 1
POZRVZJJTULAOH-LHZXLZLDSA-N danazol Chemical compound C1[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=CC2=C1C=NO2 POZRVZJJTULAOH-LHZXLZLDSA-N 0.000 description 1
229960000766 danazol Drugs 0.000 description 1
229960003109 daunorubicin hydrochloride Drugs 0.000 description 1
235000019258 dehydroacetic acid Nutrition 0.000 description 1
229940061632 dehydroacetic acid Drugs 0.000 description 1
FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 description 1
230000001934 delay Effects 0.000 description 1
239000003405 delayed action preparation Substances 0.000 description 1
CFCUWKMKBJTWLW-UHFFFAOYSA-N deoliosyl-3C-alpha-L-digitoxosyl-MTM Natural products CC=1C(O)=C2C(O)=C3C(=O)C(OC4OC(C)C(O)C(OC5OC(C)C(O)C(OC6OC(C)C(O)C(C)(O)C6)C5)C4)C(C(OC)C(=O)C(O)C(C)O)CC3=CC2=CC=1OC(OC(C)C1O)CC1OC1CC(O)C(O)C(C)O1 CFCUWKMKBJTWLW-UHFFFAOYSA-N 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
238000013461 design Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
229960003957 dexamethasone Drugs 0.000 description 1
UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 description 1
229960000452 diethylstilbestrol Drugs 0.000 description 1
230000004069 differentiation Effects 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229960002918 doxorubicin hydrochloride Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000009509 drug development Methods 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
210000004696 endometrium Anatomy 0.000 description 1
229960001904 epirubicin Drugs 0.000 description 1
229950002973 epitiostanol Drugs 0.000 description 1
229950009537 epristeride Drugs 0.000 description 1
229960001766 estramustine phosphate sodium Drugs 0.000 description 1
IIUMCNJTGSMNRO-VVSKJQCTSA-L estramustine sodium phosphate Chemical compound [Na+].[Na+].ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)OP([O-])([O-])=O)[C@@H]4[C@@H]3CCC2=C1 IIUMCNJTGSMNRO-VVSKJQCTSA-L 0.000 description 1
239000000328 estrogen antagonist Substances 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
KPEUDULLQDHKAZ-VROINQGHSA-N ethinylestradiol sulfonate Chemical compound C1C[C@]2(C)[C@@](C#C)(O)CC[C@H]2[C@@H]2CCC3=CC(OS(=O)(=O)C(C)C)=CC=C3[C@H]21 KPEUDULLQDHKAZ-VROINQGHSA-N 0.000 description 1
229950001118 ethinylestradiol sulfonate Drugs 0.000 description 1
RPYGUXNZPKNPNX-UHFFFAOYSA-N ethyl 3-[2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]benzoate Chemical compound CCOC(=O)C1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C)=C1 RPYGUXNZPKNPNX-UHFFFAOYSA-N 0.000 description 1
PCPIANOJERKFJI-UHFFFAOYSA-N ethyl 5-bromopyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=CC(Br)=C1 PCPIANOJERKFJI-UHFFFAOYSA-N 0.000 description 1
WHQLQYRFIHPMNA-UHFFFAOYSA-N ethyl acetate;oxolane Chemical compound C1CCOC1.CCOC(C)=O WHQLQYRFIHPMNA-UHFFFAOYSA-N 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
229960005237 etoglucid Drugs 0.000 description 1
VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 1
229960005420 etoposide Drugs 0.000 description 1
LIQODXNTTZAGID-OCBXBXKTSA-N etoposide phosphate Chemical compound COC1=C(OP(O)(O)=O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 LIQODXNTTZAGID-OCBXBXKTSA-N 0.000 description 1
229960000752 etoposide phosphate Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
229960000255 exemestane Drugs 0.000 description 1
229950011548 fadrozole Drugs 0.000 description 1
DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical compound N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 description 1
229960004039 finasteride Drugs 0.000 description 1
229960000390 fludarabine Drugs 0.000 description 1
GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 description 1
229960002074 flutamide Drugs 0.000 description 1
MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
229960004421 formestane Drugs 0.000 description 1
OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
229960005277 gemcitabine Drugs 0.000 description 1
SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 1
229960004761 gestrinone Drugs 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
XLXSAKCOAKORKW-UHFFFAOYSA-N gonadorelin Chemical compound C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 XLXSAKCOAKORKW-UHFFFAOYSA-N 0.000 description 1
XLXSAKCOAKORKW-AQJXLSMYSA-N gonadorelin Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 XLXSAKCOAKORKW-AQJXLSMYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229960003569 hematoporphyrin Drugs 0.000 description 1
229940022353 herceptin Drugs 0.000 description 1
UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 description 1
MOTRZVVGCFFABN-UHFFFAOYSA-N hexane;2-propan-2-yloxypropane Chemical compound CCCCCC.CC(C)OC(C)C MOTRZVVGCFFABN-UHFFFAOYSA-N 0.000 description 1
229940125697 hormonal agent Drugs 0.000 description 1
229960000890 hydrocortisone Drugs 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229920001477 hydrophilic polymer Polymers 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
229960001330 hydroxycarbamide Drugs 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
229950000801 hydroxyprogesterone caproate Drugs 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
229940071676 hydroxypropylcellulose Drugs 0.000 description 1
230000036031 hyperthermia Effects 0.000 description 1
238000009217 hyperthermia therapy Methods 0.000 description 1
229960001176 idarubicin hydrochloride Drugs 0.000 description 1
229960001101 ifosfamide Drugs 0.000 description 1
HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000002955 immunomodulating agent Substances 0.000 description 1
238000009169 immunotherapy Methods 0.000 description 1
229950008097 improsulfan Drugs 0.000 description 1
DBIGHPPNXATHOF-UHFFFAOYSA-N improsulfan Chemical compound CS(=O)(=O)OCCCNCCCOS(C)(=O)=O DBIGHPPNXATHOF-UHFFFAOYSA-N 0.000 description 1
239000000411 inducer Substances 0.000 description 1
238000001802 infusion Methods 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
229940079322 interferon Drugs 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
229940084651 iressa Drugs 0.000 description 1
UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 description 1
229960004768 irinotecan Drugs 0.000 description 1
238000002955 isolation Methods 0.000 description 1
HJHXYSBRTVFEDD-UHFFFAOYSA-N isoquinoline-1-carbonitrile Chemical compound C1=CC=C2C(C#N)=NC=CC2=C1 HJHXYSBRTVFEDD-UHFFFAOYSA-N 0.000 description 1
GXXBVBVNGMCFIU-UHFFFAOYSA-N isoquinoline-3-carbonitrile Chemical compound C1=CC=C2C=NC(C#N)=CC2=C1 GXXBVBVNGMCFIU-UHFFFAOYSA-N 0.000 description 1
125000005956 isoquinolyl group Chemical group 0.000 description 1
239000007951 isotonicity adjuster Substances 0.000 description 1
229940043355 kinase inhibitor Drugs 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
229940115286 lentinan Drugs 0.000 description 1
229960003881 letrozole Drugs 0.000 description 1
HPJKCIUCZWXJDR-UHFFFAOYSA-N letrozole Chemical compound C1=CC(C#N)=CC=C1C(N1N=CN=C1)C1=CC=C(C#N)C=C1 HPJKCIUCZWXJDR-UHFFFAOYSA-N 0.000 description 1
229960002293 leucovorin calcium Drugs 0.000 description 1
229960001614 levamisole Drugs 0.000 description 1
229950002728 levormeloxifene Drugs 0.000 description 1
XZEUAXYWNKYKPL-WDYNHAJCSA-N levormeloxifene Chemical compound C1([C@H]2[C@@H](C3=CC=C(C=C3OC2(C)C)OC)C=2C=CC(OCCN3CCCC3)=CC=2)=CC=CC=C1 XZEUAXYWNKYKPL-WDYNHAJCSA-N 0.000 description 1
239000003446 ligand Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229960002247 lomustine Drugs 0.000 description 1
229960003511 macrogol Drugs 0.000 description 1
DQDWATOXYCARFV-UHFFFAOYSA-M magnesium;2-methanidylpropane;bromide Chemical compound [Mg+2].[Br-].CC(C)[CH2-] DQDWATOXYCARFV-UHFFFAOYSA-M 0.000 description 1
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
230000000873 masking effect Effects 0.000 description 1
238000005259 measurement Methods 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
229960002985 medroxyprogesterone 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
229960004296 megestrol acetate Drugs 0.000 description 1
229960001924 melphalan Drugs 0.000 description 1
SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 1
GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 1
229960001428 mercaptopurine Drugs 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
WVJKHCGMRZGIJH-UHFFFAOYSA-N methanetriamine Chemical compound NC(N)N WVJKHCGMRZGIJH-UHFFFAOYSA-N 0.000 description 1
229960000485 methotrexate Drugs 0.000 description 1
238000006063 methoxycarbonylation reaction Methods 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
229960002900 methylcellulose Drugs 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
229950002777 miboplatin Drugs 0.000 description 1
190000032366 miboplatin Chemical compound 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
230000003228 microsomal effect Effects 0.000 description 1
210000001589 microsome Anatomy 0.000 description 1
229960004857 mitomycin Drugs 0.000 description 1
229960000350 mitotane Drugs 0.000 description 1
ZAHQPTJLOCWVPG-UHFFFAOYSA-N mitoxantrone dihydrochloride Chemical compound Cl.Cl.O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO ZAHQPTJLOCWVPG-UHFFFAOYSA-N 0.000 description 1
229960004169 mitoxantrone hydrochloride Drugs 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
238000000465 moulding Methods 0.000 description 1
ATNFZBRIBVITOK-UHFFFAOYSA-N n,4-dimethyl-3-[4-(4-propan-2-ylpyridin-3-yl)-1,3-thiazol-2-yl]benzamide Chemical compound CNC(=O)C1=CC=C(C)C(C=2SC=C(N=2)C=2C(=CC=NC=2)C(C)C)=C1 ATNFZBRIBVITOK-UHFFFAOYSA-N 0.000 description 1
PCIWDXDOXNNNOB-UHFFFAOYSA-N n,n-dimethyl-3-[2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]benzamide Chemical compound CN(C)C(=O)C1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C)=C1 PCIWDXDOXNNNOB-UHFFFAOYSA-N 0.000 description 1
KQBDNRGECQPXCN-UHFFFAOYSA-N n,n-dimethyl-3-[4-(4-propan-2-ylpyridin-3-yl)-1,3-thiazol-2-yl]benzamide Chemical compound CC(C)C1=CC=NC=C1C1=CSC(C=2C=C(C=CC=2)C(=O)N(C)C)=N1 KQBDNRGECQPXCN-UHFFFAOYSA-N 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
KXBIARKNAZXRGC-UHFFFAOYSA-N n-(3-cyanophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(C#N)=C1 KXBIARKNAZXRGC-UHFFFAOYSA-N 0.000 description 1
NKFHKYQGZDAKMX-PPRKPIOESA-N n-[(e)-1-[(2s,4s)-4-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracen-2-yl]ethylideneamino]benzamide;hydrochloride Chemical compound Cl.O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(\C)=N\NC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 NKFHKYQGZDAKMX-PPRKPIOESA-N 0.000 description 1
MHLRSHDXIMQEBQ-UHFFFAOYSA-N n-[3-[2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazol-4-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C(F)(F)F)=C1 MHLRSHDXIMQEBQ-UHFFFAOYSA-N 0.000 description 1
WVADYXNHZGIYSD-UHFFFAOYSA-N n-[4-[2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazol-4-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=CSC(C=2C(=CC=NC=2)C(F)(F)F)=N1 WVADYXNHZGIYSD-UHFFFAOYSA-N 0.000 description 1
YZOHYOBIAMFXCU-UHFFFAOYSA-N n-[4-methyl-3-[4-(4-methylpyridin-3-yl)-1,3-thiazol-2-yl]phenyl]formamide Chemical compound CC1=CC=NC=C1C1=CSC(C=2C(=CC=C(NC=O)C=2)C)=N1 YZOHYOBIAMFXCU-UHFFFAOYSA-N 0.000 description 1
LTFZUVJKGYGNPS-UHFFFAOYSA-N n-ethyl-2-fluoro-5-[2-[4-(trifluoromethyl)pyridin-3-yl]-1,3-thiazol-4-yl]benzamide Chemical compound C1=C(F)C(C(=O)NCC)=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C(F)(F)F)=C1 LTFZUVJKGYGNPS-UHFFFAOYSA-N 0.000 description 1
WZLTUPAXEMTARS-UHFFFAOYSA-N n-ethyl-3-[2-(4-methylpyridin-3-yl)-1,3-thiazol-4-yl]benzamide Chemical compound CCNC(=O)C1=CC=CC(C=2N=C(SC=2)C=2C(=CC=NC=2)C)=C1 WZLTUPAXEMTARS-UHFFFAOYSA-N 0.000 description 1
229950007221 nedaplatin Drugs 0.000 description 1
QZGIWPZCWHMVQL-UIYAJPBUSA-N neocarzinostatin chromophore Chemical compound O1[C@H](C)[C@H](O)[C@H](O)[C@@H](NC)[C@H]1O[C@@H]1C/2=C/C#C[C@H]3O[C@@]3([C@@H]3OC(=O)OC3)C#CC\2=C[C@H]1OC(=O)C1=C(O)C=CC2=C(C)C=C(OC)C=C12 QZGIWPZCWHMVQL-UIYAJPBUSA-N 0.000 description 1
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
229960002653 nilutamide Drugs 0.000 description 1
XWXYUMMDTVBTOU-UHFFFAOYSA-N nilutamide Chemical compound O=C1C(C)(C)NC(=O)N1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 XWXYUMMDTVBTOU-UHFFFAOYSA-N 0.000 description 1
229960001420 nimustine Drugs 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
229940127084 other anti-cancer agent Drugs 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229960001756 oxaliplatin Drugs 0.000 description 1
DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000012856 packing Methods 0.000 description 1
229960001592 paclitaxel Drugs 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
238000005192 partition Methods 0.000 description 1
229960002340 pentostatin Drugs 0.000 description 1
FPVKHBSQESCIEP-JQCXWYLXSA-N pentostatin Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(N=CNC[C@H]2O)=C2N=C1 FPVKHBSQESCIEP-JQCXWYLXSA-N 0.000 description 1
QIMGFXOHTOXMQP-GFAGFCTOSA-N peplomycin Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCCN[C@@H](C)C=1C=CC=CC=1)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1NC=NC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C QIMGFXOHTOXMQP-GFAGFCTOSA-N 0.000 description 1
229950003180 peplomycin Drugs 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000004526 pharmaceutical effect Effects 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
229940067157 phenylhydrazine Drugs 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000003757 phosphotransferase inhibitor Substances 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229940034049 polysaccharide-k Drugs 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
229960002847 prasterone Drugs 0.000 description 1
229960004694 prednimustine Drugs 0.000 description 1
229960005205 prednisolone Drugs 0.000 description 1
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
230000002265 prevention Effects 0.000 description 1
229960001586 procarbazine hydrochloride Drugs 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
238000003672 processing method Methods 0.000 description 1
XYWJNTOURDMTPI-UHFFFAOYSA-N procodazole Chemical compound C1=CC=C2NC(CCC(=O)O)=NC2=C1 XYWJNTOURDMTPI-UHFFFAOYSA-N 0.000 description 1
229950000989 procodazole Drugs 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
201000004240 prostatic hypertrophy Diseases 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
229950003776 protoporphyrin Drugs 0.000 description 1
229950007401 pumitepa Drugs 0.000 description 1
XQWBMZWDJAZPPX-UHFFFAOYSA-N pyridine-3-carbothioamide Chemical compound NC(=S)C1=CC=CN=C1 XQWBMZWDJAZPPX-UHFFFAOYSA-N 0.000 description 1
KPIIGXWUNXGGCP-UHFFFAOYSA-N pyridine-4-carbothioamide Chemical compound NC(=S)C1=CC=NC=C1 KPIIGXWUNXGGCP-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
238000011002 quantification Methods 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
238000001959 radiotherapy Methods 0.000 description 1
229960004622 raloxifene Drugs 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
229960002185 ranimustine Drugs 0.000 description 1
238000011160 research Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
108091092562 ribozyme Proteins 0.000 description 1
ILFPCMXTASDZKM-UHFFFAOYSA-N sarkomycin Natural products OC(=O)C1CCC(=O)C1=C ILFPCMXTASDZKM-UHFFFAOYSA-N 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229950010372 sobuzoxane Drugs 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
AIELVIGKOSMFMP-UHFFFAOYSA-M sodium ethyl acetate hydrogen carbonate methanol Chemical compound [Na+].OC.OC([O-])=O.CCOC(C)=O AIELVIGKOSMFMP-UHFFFAOYSA-M 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
229940032147 starch Drugs 0.000 description 1
229960001052 streptozocin Drugs 0.000 description 1
ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940095374 tabloid Drugs 0.000 description 1
FQZYTYWMLGAPFJ-OQKDUQJOSA-N tamoxifen citrate Chemical compound [H+].[H+].[H+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 FQZYTYWMLGAPFJ-OQKDUQJOSA-N 0.000 description 1
229960003454 tamoxifen citrate Drugs 0.000 description 1
229960003198 tamsulosin hydrochloride Drugs 0.000 description 1
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
229960001674 tegafur Drugs 0.000 description 1
WFWLQNSHRPWKFK-ZCFIWIBFSA-N tegafur Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1OCCC1 WFWLQNSHRPWKFK-ZCFIWIBFSA-N 0.000 description 1
229960004964 temozolomide Drugs 0.000 description 1
NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
229960001278 teniposide Drugs 0.000 description 1
229960003604 testosterone Drugs 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical class CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
229960001196 thiotepa Drugs 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
239000012929 tonicity agent Substances 0.000 description 1
UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
229960000303 topotecan Drugs 0.000 description 1
229960004167 toremifene citrate Drugs 0.000 description 1
229950001353 tretamine Drugs 0.000 description 1
IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 1
229960005294 triamcinolone Drugs 0.000 description 1
GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
229960000875 trofosfamide Drugs 0.000 description 1
UMKFEPPTGMDVMI-UHFFFAOYSA-N trofosfamide Chemical compound ClCCN(CCCl)P1(=O)OCCCN1CCCl UMKFEPPTGMDVMI-UHFFFAOYSA-N 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
229950009811 ubenimex Drugs 0.000 description 1
208000010579 uterine corpus leiomyoma Diseases 0.000 description 1
201000007954 uterine fibroid Diseases 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
KDQAABAKXDWYSZ-PNYVAJAMSA-N vinblastine sulfate Chemical compound OS(O)(=O)=O.C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 KDQAABAKXDWYSZ-PNYVAJAMSA-N 0.000 description 1
229960004982 vinblastine sulfate Drugs 0.000 description 1
AQTQHPDCURKLKT-JKDPCDLQSA-N vincristine sulfate Chemical compound OS(O)(=O)=O.C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C=O)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 AQTQHPDCURKLKT-JKDPCDLQSA-N 0.000 description 1
229960002110 vincristine sulfate Drugs 0.000 description 1
229960005212 vindesine sulfate Drugs 0.000 description 1
GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
229960002066 vinorelbine Drugs 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
229950009268 zinostatin Drugs 0.000 description 1