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

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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 (enExample

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

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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
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