TW201319063A - 以四氫噻唑衍生物或其鹽為有效成分之醫藥品 - Google Patents

以四氫噻唑衍生物或其鹽為有效成分之醫藥品 Download PDF

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Publication number: TW201319063A
Authority: TW; Taiwan
Prior art keywords: methylene; phenyl; tetrahydrothiazole; dione; methyl
Prior art date: 2011-10-04

Application number

TW101136757A

Other languages

English (en)

Chinese (zh)

Inventor

Atsuhiro Abe

Ryuta Yamazaki

Toshio Sasai

Takashi Yaegashi

Masato Nagaoka

Akimitsu Takagi

Takeshi Matsuzaki

Masayuki Mae

Takuya Sugimoto

Tsuneyuki Kobayashi

Hiroyuki Nishiyama

Yuichi Sawaguchi

Yukiko Nishiyama

Original Assignee

Yakult Honsha Kk

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2011-10-04

Filing date

2012-10-04

Publication date

2013-05-16

2012-10-04 Application filed by Yakult Honsha Kk filed Critical Yakult Honsha Kk

2013-05-16 Publication of TW201319063A publication Critical patent/TW201319063A/zh

Links

150000003839 salts Chemical class 0.000 title claims abstract description 35
150000003548 thiazolidines Chemical class 0.000 title abstract 2
239000004480 active ingredient Substances 0.000 title 1
-1 mono-substituted amino group Chemical group 0.000 claims abstract description 149
125000001424 substituent group Chemical group 0.000 claims abstract description 74
125000000217 alkyl group Chemical group 0.000 claims abstract description 51
125000003277 amino group Chemical group 0.000 claims abstract description 45
229910052760 oxygen Inorganic materials 0.000 claims abstract description 33
229910052717 sulfur Inorganic materials 0.000 claims abstract description 33
125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 31
125000001931 aliphatic group Chemical group 0.000 claims abstract description 30
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 27
125000005843 halogen group Chemical group 0.000 claims abstract description 26
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 20
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 14
125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 4
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 402
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 307
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 201
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 201
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 152
125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 65
125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 49
ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 46
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical class C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 25
UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 25
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 22
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
125000003118 aryl group Chemical group 0.000 claims description 21
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 16
125000002950 monocyclic group Chemical group 0.000 claims description 16
125000005605 benzo group Chemical group 0.000 claims description 14
125000005842 heteroatom Chemical group 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 13
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
241000009298 Trigla lyra Species 0.000 claims description 11
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 10
125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 10
CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 10
125000002619 bicyclic group Chemical group 0.000 claims description 9
239000003112 inhibitor Substances 0.000 claims description 9
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical compound C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 claims description 9
229960002195 perazine Drugs 0.000 claims description 9
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
238000006467 substitution reaction Methods 0.000 claims description 8
239000002246 antineoplastic agent Substances 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 7
125000005309 thioalkoxy group Chemical group 0.000 claims description 7
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 6
NOLHRFLIXVQPSZ-UHFFFAOYSA-N 1,3-thiazolidin-4-one Chemical compound O=C1CSCN1 NOLHRFLIXVQPSZ-UHFFFAOYSA-N 0.000 claims description 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 3
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 3
125000004001 thioalkyl group Chemical group 0.000 claims description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000004494 ethyl ester group Chemical group 0.000 claims description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 110
150000002576 ketones Chemical class 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 632
230000000694 effects Effects 0.000 abstract description 8
239000003795 chemical substances by application Substances 0.000 abstract description 4
230000005764 inhibitory process Effects 0.000 abstract description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 273
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 226
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 216
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 208
238000005160 1H NMR spectroscopy Methods 0.000 description 205
238000006243 chemical reaction Methods 0.000 description 182
150000001299 aldehydes Chemical class 0.000 description 179
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 162
239000000243 solution Substances 0.000 description 129
235000019439 ethyl acetate Nutrition 0.000 description 104
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 103
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 99
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 94
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 88
230000015572 biosynthetic process Effects 0.000 description 87
239000007787 solid Substances 0.000 description 87
238000003786 synthesis reaction Methods 0.000 description 85
238000000034 method Methods 0.000 description 82
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
230000002829 reductive effect Effects 0.000 description 71
229920006395 saturated elastomer Polymers 0.000 description 68
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 66
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 66
239000012044 organic layer Substances 0.000 description 65
238000010898 silica gel chromatography Methods 0.000 description 60
239000002904 solvent Substances 0.000 description 58
239000013078 crystal Substances 0.000 description 56
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 50
229910052786 argon Inorganic materials 0.000 description 48
239000007864 aqueous solution Substances 0.000 description 47
235000017557 sodium bicarbonate Nutrition 0.000 description 47
229910000030 sodium bicarbonate Inorganic materials 0.000 description 47
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 44
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 44
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 42
239000000203 mixture Substances 0.000 description 42
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 40
239000011541 reaction mixture Substances 0.000 description 40
238000010992 reflux Methods 0.000 description 39
238000003756 stirring Methods 0.000 description 37
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 35
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 34
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 32
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 30
239000002585 base Substances 0.000 description 29
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 27
229910052727 yttrium Inorganic materials 0.000 description 26
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 24
235000011054 acetic acid Nutrition 0.000 description 22
239000004327 boric acid Substances 0.000 description 22
239000012267 brine Substances 0.000 description 22
238000010438 heat treatment Methods 0.000 description 22
VDWYLKPRUHCLAW-UHFFFAOYSA-N imidazo[1,2-a]pyridine-6-carbaldehyde Chemical compound C1=C(C=O)C=CC2=NC=CN21 VDWYLKPRUHCLAW-UHFFFAOYSA-N 0.000 description 22
239000010410 layer Substances 0.000 description 22
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 21
KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 21
125000000524 functional group Chemical group 0.000 description 21
239000003921 oil Substances 0.000 description 21
235000019198 oils Nutrition 0.000 description 21
KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 21
125000002947 alkylene group Chemical group 0.000 description 20
229910052763 palladium Inorganic materials 0.000 description 19
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
206010028980 Neoplasm Diseases 0.000 description 17
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 17
239000012043 crude product Substances 0.000 description 17
125000002768 hydroxyalkyl group Chemical group 0.000 description 17
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
201000011510 cancer Diseases 0.000 description 16
230000002401 inhibitory effect Effects 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 15
229910000024 caesium carbonate Inorganic materials 0.000 description 15
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 15
235000019345 sodium thiosulphate Nutrition 0.000 description 15
MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 14
229910052739 hydrogen Inorganic materials 0.000 description 14
238000007363 ring formation reaction Methods 0.000 description 14
HSCCKBPILZXRSV-UHFFFAOYSA-N 3-fluoro-n-methoxy-n-methyl-4-nitrobenzamide Chemical compound CON(C)C(=O)C1=CC=C([N+]([O-])=O)C(F)=C1 HSCCKBPILZXRSV-UHFFFAOYSA-N 0.000 description 13
239000003054 catalyst Substances 0.000 description 13
OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 13
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
235000019270 ammonium chloride Nutrition 0.000 description 12
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 12
239000001257 hydrogen Substances 0.000 description 12
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 12
238000010792 warming Methods 0.000 description 12
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 11
125000005358 mercaptoalkyl group Chemical group 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
238000010511 deprotection reaction Methods 0.000 description 10
238000000605 extraction Methods 0.000 description 10
FNXIQNQUVJJKAK-UHFFFAOYSA-N methyl 3-(4-bromophenyl)benzimidazole-5-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2N=CN1C1=CC=C(Br)C=C1 FNXIQNQUVJJKAK-UHFFFAOYSA-N 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 9
125000000753 cycloalkyl group Chemical group 0.000 description 9
235000013305 food Nutrition 0.000 description 9
239000012280 lithium aluminium hydride Substances 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
101001001642 Xenopus laevis Serine/threonine-protein kinase pim-3 Proteins 0.000 description 8
229910001873 dinitrogen Inorganic materials 0.000 description 8
238000001035 drying Methods 0.000 description 8
239000011777 magnesium Substances 0.000 description 8
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 8
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
239000003377 acid catalyst Substances 0.000 description 7
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
238000001914 filtration Methods 0.000 description 7
239000007788 liquid Substances 0.000 description 7
125000003386 piperidinyl group Chemical group 0.000 description 7
LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 7
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 7
239000001476 sodium potassium tartrate Substances 0.000 description 7
235000011006 sodium potassium tartrate Nutrition 0.000 description 7
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 7
CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 6
VADGFPDSVWQCHR-UHFFFAOYSA-N 6-bromo-3-iodoimidazo[1,2-a]pyridine Chemical compound C1=C(Br)C=CC2=NC=C(I)N21 VADGFPDSVWQCHR-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
230000009702 cancer cell proliferation Effects 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 6
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 5
125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 5
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 5
VISNFIPNFWTYAZ-UHFFFAOYSA-N 3-(3-bromophenyl)-n-methoxy-n-methylbenzimidazole-5-carboxamide Chemical compound C12=CC(C(=O)N(C)OC)=CC=C2N=CN1C1=CC=CC(Br)=C1 VISNFIPNFWTYAZ-UHFFFAOYSA-N 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered

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Nitrogen Condensed Heterocyclic Rings (AREA)
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TW101136757A 2011-10-04 2012-10-04 以四氫噻唑衍生物或其鹽為有效成分之醫藥品 TW201319063A (zh)

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JP (1)	JP6057907B2 (fr)
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WO (1)	WO2013051672A1 (fr)

Cited By (2)

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CN106170480A (zh) *	2014-05-09	2016-11-30	上海科胜药物研发有限公司	新的沃替西汀中间体及其合成方法
CN107188901A (zh) *	2017-05-27	2017-09-22	无锡捷化医药科技有限公司	一种(3‑(3‑(二甲氨基)丙氧基)苯基)硼酸的制备方法

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JP6023630B2 (ja) *	2013-04-03	2016-11-09	株式会社ヤクルト本社	チアゾロン誘導体
US9828348B2 (en)	2013-11-08	2017-11-28	Purdue Pharma L.P.	Benzimidazole derivatives and use thereof
GB201321740D0 (en) *	2013-12-09	2014-01-22	Ucb Pharma Sa	Therapeutic agents
CA3063723A1 (fr)	2017-05-18	2018-11-22	Modernatx, Inc.	Polynucleotides codant pour des polypeptides d'interleukine-12 (il12) ancres et leurs utilisations
CN113717100B (zh) *	2021-10-11	2023-03-17	郑州工业应用技术学院	一种培氟沙星醛缩4-芳基氨基硫脲类衍生物的制备方法
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MX2009004700A (es) *	2006-11-06	2009-05-15	Supergen Inc	Derivados de imidazo[1,2-b]piridazin y pirazolo[1,5-a] pirimidina y su uso como inhibidores de proteina cinasa.
TWI461423B (zh) *	2008-07-02	2014-11-21	Astrazeneca Ab	用於治療Pim激酶相關病狀及疾病之噻唑啶二酮化合物
JP5472642B2 (ja) *	2008-09-26	2014-04-16	日本電気株式会社	信号処理方法、信号処理装置、および信号処理プログラム
NZ596571A (en) *	2009-05-20	2013-03-28	Cylene Pharmaceuticals Inc	Pyrazolopyrimidines and related heterocycles as kinase inhibitors
SG179083A1 (en) *	2009-09-11	2012-04-27	Cylene Pharmaceuticals Inc	Pharmaceutically useful heterocycle-substituted lactams

2012
- 2012-10-04 WO PCT/JP2012/075857 patent/WO2013051672A1/fr not_active Ceased
- 2012-10-04 TW TW101136757A patent/TW201319063A/zh unknown
- 2012-10-04 JP JP2013537559A patent/JP6057907B2/ja not_active Expired - Fee Related

Cited By (2)

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CN106170480A (zh) *	2014-05-09	2016-11-30	上海科胜药物研发有限公司	新的沃替西汀中间体及其合成方法
CN107188901A (zh) *	2017-05-27	2017-09-22	无锡捷化医药科技有限公司	一种(3‑(3‑(二甲氨基)丙氧基)苯基)硼酸的制备方法

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WO2013051672A1 (fr)	2013-04-11
JPWO2013051672A1 (ja)	2015-03-30
JP6057907B2 (ja)	2017-01-11

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TW201319063A - 以四氫噻唑衍生物或其鹽為有效成分之醫藥品 - Google Patents

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