RU2006133455A - Химический способ - Google Patents
Химический способ Download PDFInfo
- Publication number
- RU2006133455A RU2006133455A RU2006133455/04A RU2006133455A RU2006133455A RU 2006133455 A RU2006133455 A RU 2006133455A RU 2006133455/04 A RU2006133455/04 A RU 2006133455/04A RU 2006133455 A RU2006133455 A RU 2006133455A RU 2006133455 A RU2006133455 A RU 2006133455A
- Authority
- RU
- Russia
- Prior art keywords
- butyl
- lithium
- formula
- phenyl
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 24
- 150000001875 compounds Chemical class 0.000 claims abstract 10
- -1 substituted aryl lithium Chemical compound 0.000 claims abstract 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract 8
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims abstract 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract 6
- WXOMKINBRCKWNI-UHFFFAOYSA-N [4-(1,3,4-oxadiazol-2-yl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=NN=CO1 WXOMKINBRCKWNI-UHFFFAOYSA-N 0.000 claims abstract 6
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 claims abstract 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 5
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims abstract 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims abstract 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims abstract 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims abstract 4
- 229910052744 lithium Inorganic materials 0.000 claims abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims abstract 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract 4
- 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 abstract 4
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 claims abstract 2
- 101150003085 Pdcl gene Proteins 0.000 claims abstract 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000007983 Tris buffer Substances 0.000 claims abstract 2
- FYOQEFGAZKEPGG-UHFFFAOYSA-N [Li]C1=CC=C(C)C=C1 Chemical group [Li]C1=CC=C(C)C=C1 FYOQEFGAZKEPGG-UHFFFAOYSA-N 0.000 claims abstract 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims abstract 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims abstract 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000003446 ligand Substances 0.000 claims abstract 2
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052763 palladium Inorganic materials 0.000 claims abstract 2
- 235000011056 potassium acetate Nutrition 0.000 claims abstract 2
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical group CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 claims abstract 2
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 claims abstract 2
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 claims 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 1
- 239000011698 potassium fluoride Substances 0.000 claims 1
- 235000003270 potassium fluoride Nutrition 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Abstract
1. Способ получения соединения формулы Iв которойXвыбирают из О, NRили S, иХвыбирают из СН или N,где Rпредставляет собой азот-защитную группу,который включаетпоследовательное взаимодействие соединения формулы IIс(i) метил- или необязательно замещенным арил-литием; и после этого(ii) н-бутил-, втор-бутил-, трет-бутил- или н-гексил-литием; и затем(iii) сложным боратным эфиром.2. Способ по п.1, в котором Xпредставляет собой О.3. Способ по п.1, в котором Хпредставляет собой N.4. Способ по п.1, в котором указанный метил- или необязательно замещенный арил-литий представляет собой 4-метилфениллитий или метиллитий.5. Способ по п.1, в котором указанный н-бутил-, втор-бутил-, трет-бутил- или н-гексил-литий представляет собой н-гексиллитий или н-бутиллитий.6. Способ по п.1, в котором указанный сложный боратный эфир представляет собой триизопропилборат.7. [4-(1,3,4-Оксадиазол-2-ил)фенил]бороновая кислота, полученная способом по любому из пп.1-6.8. Способ получения соединений формулы IVкоторый включает сочетание [4-(1,3,4-оксадиазол-2-ил)фенил]бороновой кислоты с соединением формулы IIIв которой Р представляет собой азот-защитную группу.9. Способ по п.8, который осуществляют в присутствии:(i) источника палладия (0), выбранного из PdCl, Pd(PhР)или Pd(OAc);(ii) подходящего лиганда, выбранного из трифенилфосфина или тринатриевой соли 3,3',3''-фосфинидина трис(бензолсульфоновой кислоты);(iii) основания, выбранного из триэтиламина, бензилдиметиламина, N-метилморфолина, N-метилпиперидина, триэтаноламина, этилдиэтаноламина, диизопропилэтиламина, ацетата калия, фторида цезия или фторида калия.10. Способ по п.8, в котором указанную [4-(1,3,4-оксадиазол-2-ил)фенил]бороновую кислоту получают способом
Claims (13)
1. Способ получения соединения формулы I
в которой
X1 выбирают из О, NR1 или S, и
Х2 выбирают из СН или N,
где R1 представляет собой азот-защитную группу,
который включает
последовательное взаимодействие соединения формулы II
с
(i) метил- или необязательно замещенным арил-литием; и после этого
(ii) н-бутил-, втор-бутил-, трет-бутил- или н-гексил-литием; и затем
(iii) сложным боратным эфиром.
2. Способ по п.1, в котором X1 представляет собой О.
3. Способ по п.1, в котором Х2 представляет собой N.
4. Способ по п.1, в котором указанный метил- или необязательно замещенный арил-литий представляет собой 4-метилфениллитий или метиллитий.
5. Способ по п.1, в котором указанный н-бутил-, втор-бутил-, трет-бутил- или н-гексил-литий представляет собой н-гексиллитий или н-бутиллитий.
6. Способ по п.1, в котором указанный сложный боратный эфир представляет собой триизопропилборат.
7. [4-(1,3,4-Оксадиазол-2-ил)фенил]бороновая кислота, полученная способом по любому из пп.1-6.
8. Способ получения соединений формулы IV
который включает сочетание [4-(1,3,4-оксадиазол-2-ил)фенил]бороновой кислоты с соединением формулы III
в которой Р представляет собой азот-защитную группу.
9. Способ по п.8, который осуществляют в присутствии:
(i) источника палладия (0), выбранного из PdCl2, Pd(Ph3Р)4 или Pd(OAc)2;
(ii) подходящего лиганда, выбранного из трифенилфосфина или тринатриевой соли 3,3',3''-фосфинидина трис(бензолсульфоновой кислоты);
(iii) основания, выбранного из триэтиламина, бензилдиметиламина, N-метилморфолина, N-метилпиперидина, триэтаноламина, этилдиэтаноламина, диизопропилэтиламина, ацетата калия, фторида цезия или фторида калия.
10. Способ по п.8, в котором указанную [4-(1,3,4-оксадиазол-2-ил)фенил]бороновую кислоту получают способом по любому из пп.1-6.
11. Способ по п.8, в котором Р представляет собой изобутоксикарбонил.
12. Соединение формулы IV
в которой Р представляет собой азот-защитную группу.
13. Соединение формулы IV по п.12, которое представляет собой N-(изобутоксикарбонил)-N-(3-метокси-5-метилпиразин-2-ил)-2-(4-[1,3,4-оксадиазол-2-ил]фенил)пиридин-3-сульфонамид.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0403744.6A GB0403744D0 (en) | 2004-02-20 | 2004-02-20 | Chemical process |
| GB0403744.6 | 2004-02-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2006133455A true RU2006133455A (ru) | 2008-03-27 |
| RU2386636C2 RU2386636C2 (ru) | 2010-04-20 |
Family
ID=32040047
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2006133455/04A RU2386636C2 (ru) | 2004-02-20 | 2005-02-17 | Химический способ |
Country Status (32)
| Country | Link |
|---|---|
| US (2) | US7626020B2 (ru) |
| EP (3) | EP1718655A2 (ru) |
| JP (2) | JP2007523906A (ru) |
| KR (2) | KR20120036998A (ru) |
| CN (1) | CN1922193B (ru) |
| AR (1) | AR047810A1 (ru) |
| AT (1) | ATE535532T1 (ru) |
| AU (1) | AU2005214138B2 (ru) |
| BR (1) | BRPI0507847A (ru) |
| CA (1) | CA2555554A1 (ru) |
| CL (1) | CL2011003138A1 (ru) |
| CY (1) | CY1112555T1 (ru) |
| DK (1) | DK2135873T3 (ru) |
| ES (1) | ES2375201T3 (ru) |
| GB (1) | GB0403744D0 (ru) |
| HK (1) | HK1139689A1 (ru) |
| HR (1) | HRP20120031T1 (ru) |
| IL (2) | IL177505A (ru) |
| MY (1) | MY142268A (ru) |
| NO (1) | NO20064012L (ru) |
| PL (1) | PL2135873T3 (ru) |
| PT (1) | PT2135873E (ru) |
| RS (1) | RS52300B (ru) |
| RU (1) | RU2386636C2 (ru) |
| SA (1) | SA05260017B1 (ru) |
| SG (1) | SG153856A1 (ru) |
| SI (1) | SI2135873T1 (ru) |
| TW (1) | TWI347947B (ru) |
| UA (1) | UA83418C2 (ru) |
| UY (1) | UY28754A1 (ru) |
| WO (1) | WO2005080403A2 (ru) |
| ZA (1) | ZA200606579B (ru) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0219660D0 (en) | 2002-08-23 | 2002-10-02 | Astrazeneca Ab | Therapeutic use |
| JO3598B1 (ar) | 2006-10-10 | 2020-07-05 | Infinity Discovery Inc | الاحماض والاسترات البورونية كمثبطات اميد هيدروليز الحامض الدهني |
| CA2667545A1 (en) * | 2006-10-25 | 2008-05-02 | Neurosearch A/S | Oxadiazole and thiadiazole compounds and their use as nicotinic acetylcholine receptor modulators |
| TW201000107A (en) * | 2008-04-09 | 2010-01-01 | Infinity Pharmaceuticals Inc | Inhibitors of fatty acid amide hydrolase |
| WO2010118155A1 (en) | 2009-04-07 | 2010-10-14 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| WO2010118159A1 (en) | 2009-04-07 | 2010-10-14 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| CN102834401B (zh) | 2010-02-03 | 2016-08-24 | 无限药品股份有限公司 | 脂肪酸酰胺水解酶抑制剂 |
| CN102491973A (zh) * | 2011-12-15 | 2012-06-13 | 南京友杰医药科技有限公司 | Zd-4054的合成方法 |
| US11078528B2 (en) | 2015-10-12 | 2021-08-03 | Advanced Cell Diagnostics, Inc. | In situ detection of nucleotide variants in high noise samples, and compositions and methods related thereto |
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