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 Table
- 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 Table
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
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.
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.
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 |
---|---|---|---|
GB0403744.6 | 2004-02-20 | ||
GBGB0403744.6A GB0403744D0 (en) | 2004-02-20 | 2004-02-20 | Chemical process |
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) | KR101196111B1 (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) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
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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 |
PE20091838A1 (es) * | 2008-04-09 | 2009-12-18 | Infinity Pharmaceuticals Inc | Inhibidores de amida hidrolasa de acido graso |
JP2012523425A (ja) | 2009-04-07 | 2012-10-04 | インフイニトイ プハルマセウトイカルス インコーポレイテッド | 脂肪酸アミドヒドロラーゼの阻害薬 |
CA2757679A1 (en) | 2009-04-07 | 2010-10-14 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
RU2569061C2 (ru) | 2010-02-03 | 2015-11-20 | Инфинити Фармасьютикалз, Инк. | Ингибиторы амид-гидролазы жирных кислот |
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 |
CN108368543B (zh) | 2015-10-12 | 2023-06-13 | 领先细胞医疗诊断有限公司 | 高噪声样品中原位检测核苷酸变体及相关的组合物和方法 |
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