JP2004091486A5 - - Google Patents
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- Publication number
- JP2004091486A5 JP2004091486A5 JP2003291584A JP2003291584A JP2004091486A5 JP 2004091486 A5 JP2004091486 A5 JP 2004091486A5 JP 2003291584 A JP2003291584 A JP 2003291584A JP 2003291584 A JP2003291584 A JP 2003291584A JP 2004091486 A5 JP2004091486 A5 JP 2004091486A5
- Authority
- JP
- Japan
- Prior art keywords
- ddd
- stirred
- mixture
- ethyl
- water
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- XQSGYYNFKIQWAC-UHFFFAOYSA-N 4-fluoronaphthalene-1-carbonitrile Chemical compound C1=CC=C2C(F)=CC=C(C#N)C2=C1 XQSGYYNFKIQWAC-UHFFFAOYSA-N 0.000 description 2
- XASOHFCUIQARJT-UHFFFAOYSA-N 8-methoxy-6-[7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C(N1C(=O)C2=C(OC)C=C(C=3N4C(=NC=3)C=C(C=C4)OCCN3CCOCC3)C=C2CC1)C(F)(F)F XASOHFCUIQARJT-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- WNEAVWWWUXXJPC-UHFFFAOYSA-N 1-benzyl-5-hydroxy-5-methylpiperidin-2-one Chemical compound C1C(C)(O)CCC(=O)N1CC1=CC=CC=C1 WNEAVWWWUXXJPC-UHFFFAOYSA-N 0.000 description 1
- QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 description 1
- XGWBJUGIINIZDT-UHFFFAOYSA-N 4-[4-(3-hydroxypropyl)piperidin-1-yl]naphthalene-1-carbonitrile Chemical compound C1CC(CCCO)CCN1C1=CC=C(C#N)C2=CC=CC=C12 XGWBJUGIINIZDT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- -1 Lithium aluminum hydride Chemical compound 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003291584A JP4426792B2 (ja) | 2002-08-12 | 2003-08-11 | 縮合ベンゼン誘導体および用途 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002235275 | 2002-08-12 | ||
| JP2003291584A JP4426792B2 (ja) | 2002-08-12 | 2003-08-11 | 縮合ベンゼン誘導体および用途 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004091486A JP2004091486A (ja) | 2004-03-25 |
| JP2004091486A5 true JP2004091486A5 (enExample) | 2006-09-21 |
| JP4426792B2 JP4426792B2 (ja) | 2010-03-03 |
Family
ID=32072391
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003291584A Expired - Fee Related JP4426792B2 (ja) | 2002-08-12 | 2003-08-11 | 縮合ベンゼン誘導体および用途 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4426792B2 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008531503A (ja) * | 2005-02-23 | 2008-08-14 | スミスクライン ビーチャム コーポレーション | グルココルチコイド受容体のモジュレーターとしてのナフタレン誘導体 |
| US8592452B2 (en) * | 2005-08-01 | 2013-11-26 | Takeda Pharmaceutical Company Limited | Cyclic amine compound |
| MY176727A (en) * | 2012-12-03 | 2020-08-20 | Pfizer | Selective androgen receptor modulators |
| ES2864079T3 (es) * | 2014-05-30 | 2021-10-13 | Pfizer | Derivados de carbonitrilo como moduladores selectivos del receptor de andrógenos |
| CN115475158A (zh) * | 2022-09-27 | 2022-12-16 | 广西科技大学 | 一种萘腈类衍生物在制备抗肿瘤药物组合物中的应用 |
-
2003
- 2003-08-11 JP JP2003291584A patent/JP4426792B2/ja not_active Expired - Fee Related
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