JP2004535444A5 - - Google Patents
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- Publication number
- JP2004535444A5 JP2004535444A5 JP2003508683A JP2003508683A JP2004535444A5 JP 2004535444 A5 JP2004535444 A5 JP 2004535444A5 JP 2003508683 A JP2003508683 A JP 2003508683A JP 2003508683 A JP2003508683 A JP 2003508683A JP 2004535444 A5 JP2004535444 A5 JP 2004535444A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- process according
- thioamide
- halogen
- conversion
- 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
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- 238000000034 method Methods 0.000 claims 36
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 13
- 238000006243 chemical reaction Methods 0.000 claims 10
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- 239000003054 catalyst Substances 0.000 claims 6
- 125000005059 halophenyl group Chemical group 0.000 claims 6
- 229910052763 palladium Inorganic materials 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 239000003153 chemical reaction reagent Substances 0.000 claims 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 4
- 230000003647 oxidation Effects 0.000 claims 4
- 238000007254 oxidation reaction Methods 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- 229910052751 metal Inorganic materials 0.000 claims 3
- 239000002184 metal Substances 0.000 claims 3
- 229910052725 zinc Inorganic materials 0.000 claims 3
- 239000011701 zinc Substances 0.000 claims 3
- CSIFGMFVGDBOQC-UHFFFAOYSA-N 3-iminobutanenitrile Chemical compound CC(=N)CC#N CSIFGMFVGDBOQC-UHFFFAOYSA-N 0.000 claims 2
- LJANCPRIUMHGJE-UHFFFAOYSA-N 4-(2-bromoacetyl)benzonitrile Chemical compound BrCC(=O)C1=CC=C(C#N)C=C1 LJANCPRIUMHGJE-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 2
- 150000002825 nitriles Chemical class 0.000 claims 2
- 125000002524 organometallic group Chemical group 0.000 claims 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 2
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- DQXKOHDUMJLXKH-PHEQNACWSA-N (e)-n-[2-[2-[[(e)-oct-2-enoyl]amino]ethyldisulfanyl]ethyl]oct-2-enamide Chemical compound CCCCC\C=C\C(=O)NCCSSCCNC(=O)\C=C\CCCCC DQXKOHDUMJLXKH-PHEQNACWSA-N 0.000 claims 1
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims 1
- 150000008046 alkali metal hydrides Chemical class 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- -1 alkali metal periodate Chemical class 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000001345 alkine derivatives Chemical class 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 claims 1
- 125000003180 beta-lactone group Chemical group 0.000 claims 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- IRDLUHRVLVEUHA-UHFFFAOYSA-N diethyl dithiophosphate Chemical compound CCOP(S)(=S)OCC IRDLUHRVLVEUHA-UHFFFAOYSA-N 0.000 claims 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 claims 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 239000012454 non-polar solvent Substances 0.000 claims 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 claims 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical group Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical group [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052718 tin Inorganic materials 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01115355 | 2001-06-26 | ||
| PCT/EP2002/006644 WO2003002498A1 (en) | 2001-06-26 | 2002-06-17 | Intermediate halophenyl derivatives and their use in a process for preparing azole derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004535444A JP2004535444A (ja) | 2004-11-25 |
| JP2004535444A5 true JP2004535444A5 (enExample) | 2005-11-17 |
| JP4125672B2 JP4125672B2 (ja) | 2008-07-30 |
Family
ID=8177821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003508683A Expired - Lifetime JP4125672B2 (ja) | 2001-06-26 | 2002-06-17 | アゾール誘導体製造方法における中間体ハロフェニル誘導体およびそれらの使用 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7115643B2 (enExample) |
| EP (1) | EP1399402B1 (enExample) |
| JP (1) | JP4125672B2 (enExample) |
| KR (1) | KR100898887B1 (enExample) |
| CN (1) | CN1223564C (enExample) |
| AT (1) | ATE482920T1 (enExample) |
| AU (1) | AU2002321068B2 (enExample) |
| BR (1) | BR0210701A (enExample) |
| CA (1) | CA2449800C (enExample) |
| CY (1) | CY1111510T1 (enExample) |
| DE (1) | DE60237817D1 (enExample) |
| DK (1) | DK1399402T3 (enExample) |
| ES (1) | ES2349918T3 (enExample) |
| MX (1) | MXPA03010914A (enExample) |
| PT (1) | PT1399402E (enExample) |
| WO (1) | WO2003002498A1 (enExample) |
| ZA (1) | ZA200309101B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8207352B2 (en) * | 2009-10-08 | 2012-06-26 | Drug Process Licensing Associates LLC | Process for the manufacture of enantiomerically pure antifungal azoles as ravuconazole and isavuconazole |
| HUE031679T2 (en) | 2012-08-07 | 2017-07-28 | Basilea Pharmaceutica Ag | Process for the preparation of isavuconazole or ravuconazole |
| US20140371179A1 (en) * | 2013-06-13 | 2014-12-18 | Professional Compounding Centers Of America | Methods and Compositions for Treating Esophageal Diseases |
| CN105801500B (zh) * | 2014-12-31 | 2018-08-24 | 四川科伦药物研究院有限公司 | 拆分艾沙康唑中间化合物消旋体的方法 |
| CN115611822B (zh) * | 2022-10-12 | 2023-09-19 | 四川澄华生物科技有限公司 | 艾沙康唑中间体的制备方法 |
| CN116478103B (zh) * | 2023-03-24 | 2025-07-25 | 四川澄华生物科技有限公司 | 一种拆分艾沙康唑中间体4的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5395942A (en) * | 1980-06-02 | 1995-03-07 | Zeneca Limited | Heterocyclic compounds |
| DE3942790A1 (de) * | 1989-12-23 | 1991-06-27 | Hoechst Ag | Verfahren zur herstellung von 2-(4-chlorphenyl)-3-methylbuttersaeure |
| GB9107055D0 (en) * | 1991-04-04 | 1991-05-22 | Pfizer Ltd | Triazole antifungal agents |
| JP3471831B2 (ja) * | 1991-12-09 | 2003-12-02 | 富山化学工業株式会社 | 新規なトリアゾール誘導体およびその塩 |
| ES2062941B1 (es) * | 1993-03-15 | 1995-10-01 | Uriach & Cia Sa J | Nuevos derivados de azol activos por via oral. |
| NZ270418A (en) | 1994-02-07 | 1997-09-22 | Eisai Co Ltd | Polycyclic triazole & imidazole derivatives, antifungal compositions |
-
2002
- 2002-06-17 AU AU2002321068A patent/AU2002321068B2/en not_active Ceased
- 2002-06-17 EP EP02754691A patent/EP1399402B1/en not_active Expired - Lifetime
- 2002-06-17 CN CNB028126416A patent/CN1223564C/zh not_active Expired - Lifetime
- 2002-06-17 PT PT02754691T patent/PT1399402E/pt unknown
- 2002-06-17 MX MXPA03010914A patent/MXPA03010914A/es active IP Right Grant
- 2002-06-17 WO PCT/EP2002/006644 patent/WO2003002498A1/en not_active Ceased
- 2002-06-17 DE DE60237817T patent/DE60237817D1/de not_active Expired - Lifetime
- 2002-06-17 CA CA002449800A patent/CA2449800C/en not_active Expired - Fee Related
- 2002-06-17 AT AT02754691T patent/ATE482920T1/de active
- 2002-06-17 KR KR1020037016987A patent/KR100898887B1/ko not_active Expired - Fee Related
- 2002-06-17 BR BR0210701-5A patent/BR0210701A/pt not_active IP Right Cessation
- 2002-06-17 ES ES02754691T patent/ES2349918T3/es not_active Expired - Lifetime
- 2002-06-17 DK DK02754691.0T patent/DK1399402T3/da active
- 2002-06-17 US US10/481,654 patent/US7115643B2/en not_active Expired - Lifetime
- 2002-06-17 JP JP2003508683A patent/JP4125672B2/ja not_active Expired - Lifetime
-
2003
- 2003-11-21 ZA ZA2003/09101A patent/ZA200309101B/en unknown
-
2010
- 2010-12-20 CY CY20101101172T patent/CY1111510T1/el unknown
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