RU2012119550A - Способы синтеза спиро-оксиндольных соединений - Google Patents
Способы синтеза спиро-оксиндольных соединений Download PDFInfo
- Publication number
- RU2012119550A RU2012119550A RU2012119550/04A RU2012119550A RU2012119550A RU 2012119550 A RU2012119550 A RU 2012119550A RU 2012119550/04 A RU2012119550/04 A RU 2012119550/04A RU 2012119550 A RU2012119550 A RU 2012119550A RU 2012119550 A RU2012119550 A RU 2012119550A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- compound
- pharmaceutically acceptable
- acceptable salt
- under suitable
- Prior art date
Links
- BHVMWYAFPVJCTG-UHFFFAOYSA-N COc1ccc2OCCOc2c1 Chemical compound COc1ccc2OCCOc2c1 BHVMWYAFPVJCTG-UHFFFAOYSA-N 0.000 description 1
- XGYVWWLZOMQVRF-UHFFFAOYSA-N O=C1N(Cc2c(C(F)(F)F)cccn2)c2ccccc2C1(COc1c2)c1cc1c2OCCO1 Chemical compound O=C1N(Cc2c(C(F)(F)F)cccn2)c2ccccc2C1(COc1c2)c1cc1c2OCCO1 XGYVWWLZOMQVRF-UHFFFAOYSA-N 0.000 description 1
- NEBUOXBYNAHKFV-NRFANRHFSA-N O=C1N(Cc2ccc(C(F)(F)F)[o]2)c2ccccc2[C@@]11c(cc2OCOc2c2)c2OC1 Chemical compound O=C1N(Cc2ccc(C(F)(F)F)[o]2)c2ccccc2[C@@]11c(cc2OCOc2c2)c2OC1 NEBUOXBYNAHKFV-NRFANRHFSA-N 0.000 description 1
Classifications
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- 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
- C07D491/12—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 three hetero rings
- C07D491/20—Spiro-condensed systems
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Abstract
1. Способ получения соединения формулы (I):или его фармацевтически приемлемой соли в виде отдельного стереоизомера или энантиомера, или их смеси;включающий обработку соединения формулы (8):или его фармацевтически приемлемой соли соединением формулы (9):или его фармацевтически приемлемой солью в подходящих условиях с получением соединения формулы (I) или его фармацевтически приемлемой соли в виде отдельного стереоизомера или энантиомера, или их смеси.2. Способ по п.1, дополнительно включающий получение соединения формулы (8), где способ включает обработку соединения формулы (7):или его фармацевтически приемлемой соли основанием в подходящих условиях с образованием соединения формулы (8) или его фармацевтически приемлемой соли.3. Способ по п.2, дополнительно включающий получение соединения формулы (7), где способ включает обработку соединения формулы (6):или его фармацевтически приемлемой соли основанием в стандартных условиях реакции Мицунобу с образованием соединения формулы (7) или его фармацевтически приемлемой соли.4. Способ по п.3, дополнительно включающий получение соединения формулы (6), где способ включает обработку соединения формулы (5):или его фармацевтически приемлемой соли альдегидом в подходящих условиях с образованием соединения формулы (6) или его фармацевтически приемлемой соли.5. Способ по п.4, дополнительно включающий получение соединения формулы (5), где способ включает обработку соединения формулы (4):или его фармацевтически приемлемой соли основанием в подходящих условиях с образованием соединения формулы (5) или его фармацевтически приемлемой соли.6. Способ по п.5, дополнительно включающий получен�
Claims (14)
1. Способ получения соединения формулы (I):
или его фармацевтически приемлемой соли в виде отдельного стереоизомера или энантиомера, или их смеси;
включающий обработку соединения формулы (8):
или его фармацевтически приемлемой соли соединением формулы (9):
или его фармацевтически приемлемой солью в подходящих условиях с получением соединения формулы (I) или его фармацевтически приемлемой соли в виде отдельного стереоизомера или энантиомера, или их смеси.
3. Способ по п.2, дополнительно включающий получение соединения формулы (7), где способ включает обработку соединения формулы (6):
или его фармацевтически приемлемой соли основанием в стандартных условиях реакции Мицунобу с образованием соединения формулы (7) или его фармацевтически приемлемой соли.
6. Способ по п.5, дополнительно включающий получение соединения формулы (4), где способ включает:
a) взаимодействие соединения формулы (2):
или его фармацевтически приемлемой соли c реактивом Гриньяра формулы (3):
в подходящих условиях с образованием промежуточного продукта; и
b) взаимодействие промежуточного продукта по a) с соединением формулы (1):
или его фармацевтически приемлемой солью в подходящих условиях с образованием соединения формулы (4) или его фармацевтически приемлемой соли.
8. Способ получения соединения формулы (II):
или его фармацевтически приемлемой соли в виде отдельного стереоизомера или энантиомера, или их смеси;
включающий обработку соединения формулы (15):
или его фармацевтически приемлемой соли соединением формулы (16):
или его фармацевтически приемлемой солью в подходящих условиях с получением соединения формулы (II) или его фармацевтически приемлемой соли в виде отдельного стереоизомера или энантиомера, или их смеси.
9. Способ по п.8, дополнительно включающий получение соединения формулы (15) или его фармацевтически приемлемой соли, где способ включает обработку соединения формулы (14):
или его фармацевтически приемлемой соли алкилирующим агентом в подходящих условиях с образованием соединения формулы (15) или его фармацевтически приемлемой соли.
10. Способ по п.9, дополнительно включающий получение соединения формулы (14) или его фармацевтически приемлемой соли, где способ включает обработку соединения формулы (13):
или его фармацевтически приемлемой соли в подходящих условиях с образованием соединения формулы (14) или его фармацевтически приемлемой соли.
11. Способ по п.10, дополнительно включающий получение соединения формулы (13) или его фармацевтически приемлемой соли, где способ включает:
a) взаимодействие соединения формулы (12):
c реактивом Гриньяра формулы (3):
в подходящих условиях с образованием промежуточного продукта; и
b) взаимодействие промежуточного продукта по a) с соединением формулы (1):
или его фармацевтически приемлемой солью в подходящих условиях с образованием соединения формулы (13) или его фармацевтически приемлемой соли.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US25133509P | 2009-10-14 | 2009-10-14 | |
US61/251,335 | 2009-10-14 | ||
PCT/US2010/052704 WO2011047174A1 (en) | 2009-10-14 | 2010-10-14 | Synthetic methods for spiro-oxindole compounds |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU2015103694/04A Division RU2015103694A (ru) | 2009-10-14 | 2010-10-14 | Способы синтеза спиро-оксиндольных соединений |
Publications (2)
Publication Number | Publication Date |
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RU2012119550A true RU2012119550A (ru) | 2013-11-20 |
RU2544852C2 RU2544852C2 (ru) | 2015-03-20 |
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Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
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RU2015103694/04A RU2015103694A (ru) | 2009-10-14 | 2010-10-14 | Способы синтеза спиро-оксиндольных соединений |
RU2012119550/04A RU2544852C2 (ru) | 2009-10-14 | 2010-10-14 | Способы синтеза спиро-оксиндольных соединений |
Family Applications Before (1)
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RU2015103694/04A RU2015103694A (ru) | 2009-10-14 | 2010-10-14 | Способы синтеза спиро-оксиндольных соединений |
Country Status (23)
Country | Link |
---|---|
US (4) | US8445696B2 (ru) |
EP (2) | EP2488531B1 (ru) |
JP (3) | JP5752136B2 (ru) |
KR (1) | KR20120099429A (ru) |
CN (1) | CN102753556B (ru) |
AU (2) | AU2010306768B2 (ru) |
BR (1) | BR112012008993A2 (ru) |
CA (1) | CA2777543A1 (ru) |
CL (3) | CL2012000953A1 (ru) |
CO (1) | CO6531444A2 (ru) |
EC (1) | ECSP12011815A (ru) |
ES (1) | ES2467166T3 (ru) |
HK (2) | HK1174908A1 (ru) |
HR (2) | HRP20120368A2 (ru) |
MA (1) | MA33730B1 (ru) |
MX (1) | MX2012004373A (ru) |
MY (2) | MY179342A (ru) |
NZ (3) | NZ599334A (ru) |
PE (2) | PE20121350A1 (ru) |
RU (2) | RU2015103694A (ru) |
TN (1) | TN2012000171A1 (ru) |
WO (1) | WO2011047174A1 (ru) |
ZA (1) | ZA201202703B (ru) |
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BRPI0719210A2 (pt) | 2006-10-12 | 2015-05-05 | Xenon Pharmaceuticals Inc | Uso de compostos espiro-oxindol como agentes terapêuticos |
CA2666143A1 (en) * | 2006-10-12 | 2008-04-17 | Xenon Pharmaceuticals Inc. | Spiro (furo [3, 2-c] pyridine-3-3 ' -indol) -2' (1'h)-one derivatives and related compounds for the treatment of sodium-channel mediated diseases, such as pain |
CN102256983B (zh) | 2008-10-17 | 2017-04-05 | 泽农医药公司 | 螺羟吲哚化合物及其作为治疗剂的用途 |
CA2741024A1 (en) * | 2008-10-17 | 2010-04-22 | Xenon Pharmaceuticals Inc. | Spiro-oxindole compounds and their use as therapeutic agents |
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