UY25524A1 - METHOD FOR PREPARING SUBSTITUTED 4-PHENYL4-CIANOCICLOHEXANOIC ACIDS - Google Patents
METHOD FOR PREPARING SUBSTITUTED 4-PHENYL4-CIANOCICLOHEXANOIC ACIDSInfo
- Publication number
- UY25524A1 UY25524A1 UY25524A UY25524A UY25524A1 UY 25524 A1 UY25524 A1 UY 25524A1 UY 25524 A UY25524 A UY 25524A UY 25524 A UY25524 A UY 25524A UY 25524 A1 UY25524 A1 UY 25524A1
- Authority
- UY
- Uruguay
- Prior art keywords
- hydrogen
- precipitate
- acid
- acids
- cyclopentyloxy
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Método para sintetizar compuestos de fórmula (I) representada en la figura 1, dond: R' y R'' son independientemente hidrógeno o -C(O)OX, siendo X hidrógeno o un catión metálico o amonio; R3 es hidrógeno, halógeno, alquilo, CH2NHC(O)C(O)NH2, ciclopropilo; X2 es O o NR8, siendo R8 hidrógeno o alquilo C1-C4 opcionalmente sustituid con uno a tres átomos de flúor; el método comprende combinar un haluro de un alcalino o alcalinotérreo con un disolvente aprótico dipolar, básicamente amídico, agua y uno de los compuestos representados en la figura 2 (particularmente el cis-6-[3-(ciclopentiloxi)-4-metoxifenil)]-1-oxaespiro[2,5]octano-2,6-dicarbonitrilo), y calentar la combinación a una temperatura de al menos aproximadamente 60s durante varias horas, opcionalmente en una atmósfera inerte, precipitar un compuesto de fórmula (I) por adición de una base fuerte a dicha combinación, luego retirar el disolvente básicamente amídico y el agua de dicho precipitado, y opcionalmente purificar aún más el precipitado, o acidular el precipitado para obtener el ácido libre. En especial se incluyen compuestos intermedios y a una ruta sintética para obtener ácido 4-ciano-4-(3-ciclopentiloxi-4-metoxifenil)ciclohexanoico y sus análogos. Este ácido y sus análogos nombrados son selectivos inhibidores del sitio catalítico en la isoenzima fosfodiesterasa denominada IV ("PDE IV") y por ello los ácidos son útiles en el tratamiento de ciertas enfermedades que se pueden aliviar afectando a la enzima PDE IV y sus subtipos.Method for synthesizing compounds of formula (I) represented in figure 1, where: R 'and R' 'are independently hydrogen or -C (O) OX, where X is hydrogen or a metal or ammonium cation; R3 is hydrogen, halogen, alkyl, CH2NHC (O) C (O) NH2, cyclopropyl; X2 is O or NR8, with R8 being hydrogen or C1-C4 alkyl optionally substituted with one to three fluorine atoms; the method comprises combining a halide of an alkaline or alkaline earth with a dipolar aprotic solvent, basically amidic, water and one of the compounds represented in figure 2 (particularly cis-6- [3- (cyclopentyloxy) -4-methoxyphenyl)] -1-oxaspiro [2,5] octano-2,6-dicarbonitrile), and heating the combination to a temperature of at least about 60s for several hours, optionally in an inert atmosphere, precipitating a compound of formula (I) by addition from a strong base to said combination, then remove basically amidic solvent and water from said precipitate, and optionally further purify the precipitate, or acidify the precipitate to obtain the free acid. In particular, intermediate compounds and a synthetic route to obtain 4-cyano-4- (3-cyclopentyloxy-4-methoxyphenyl) cyclohexanoic acid and its analogs are included. This acid and its named analogues are selective inhibitors of the catalytic site in the isoenzyme phosphodiesterase called IV ("PDE IV") and therefore the acids are useful in the treatment of certain diseases that can be alleviated by affecting the enzyme PDE IV and its subtypes .
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6161397P | 1997-10-10 | 1997-10-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UY25524A1 true UY25524A1 (en) | 2000-02-23 |
Family
ID=22036929
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UY25201A UY25201A1 (en) | 1997-10-10 | 1998-10-07 | METHOD FOR TREATING SUBSTITUTED 4-PHENYL-4-CYANOCICLOHEXANOIC ACID |
| UY25524A UY25524A1 (en) | 1997-10-10 | 1999-05-25 | METHOD FOR PREPARING SUBSTITUTED 4-PHENYL4-CIANOCICLOHEXANOIC ACIDS |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UY25201A UY25201A1 (en) | 1997-10-10 | 1998-10-07 | METHOD FOR TREATING SUBSTITUTED 4-PHENYL-4-CYANOCICLOHEXANOIC ACID |
Country Status (30)
| Country | Link |
|---|---|
| EP (1) | EP1043930A4 (en) |
| JP (1) | JP2001519363A (en) |
| KR (1) | KR100560038B1 (en) |
| CN (1) | CN1192025C (en) |
| AP (1) | AP1335A (en) |
| AR (1) | AR015952A1 (en) |
| AU (1) | AU741832B2 (en) |
| BG (1) | BG104302A (en) |
| BR (1) | BR9814064A (en) |
| CA (1) | CA2305614A1 (en) |
| DZ (1) | DZ2619A1 (en) |
| EA (1) | EA003609B1 (en) |
| HU (1) | HUP0003905A3 (en) |
| ID (1) | ID25536A (en) |
| IL (1) | IL135434A (en) |
| MA (1) | MA24670A1 (en) |
| MY (1) | MY122105A (en) |
| NO (1) | NO20001777L (en) |
| NZ (1) | NZ503759A (en) |
| OA (1) | OA11347A (en) |
| PE (1) | PE121599A1 (en) |
| PL (1) | PL191974B1 (en) |
| SA (1) | SA99191000A (en) |
| SK (1) | SK4902000A3 (en) |
| TR (1) | TR200000945T2 (en) |
| TW (1) | TW440557B (en) |
| UA (1) | UA67753C2 (en) |
| UY (2) | UY25201A1 (en) |
| WO (1) | WO1999018793A1 (en) |
| ZA (1) | ZA989228B (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9920152D0 (en) * | 1999-08-25 | 1999-10-27 | Smithkline Beecham Plc | Novel process |
| EP1237851A4 (en) * | 1999-12-15 | 2004-06-23 | Smithkline Beecham | SALTS OF i Cis /i -4-CYANO-4- 3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]CYCLOHEXANE-1-CARBOXYLIC ACID |
| SK10942002A3 (en) * | 2000-01-26 | 2002-11-06 | Smithkline Beecham Corporation | Monohydrate of cis-lithium-cyano-4-[3-(cyclopentyloxy)-4- methoxyphenyl]cyclohexanecarboxylate |
| EP2258689A1 (en) | 2000-03-16 | 2010-12-08 | Biolipox AB | Benzylated PDE4 inhibitors |
| HUP0302891A2 (en) | 2001-01-31 | 2003-12-29 | Pfizer Products Inc. | Ether derivatives useful as inhibitors of pde4 isozymes, their use and pharmaceutical compositions containing them |
| US7250518B2 (en) | 2001-01-31 | 2007-07-31 | Pfizer Inc. | Nicotinamide acids, amides, and their mimetics active as inhibitors of PDE4 isozymes |
| EA200300621A1 (en) | 2001-01-31 | 2003-12-25 | Пфайзер Продактс Инк. | BIARRYLIC DERIVATIVES OF NICOTINAMIDE, USEFUL AS AN INHIBITORS OF PDE4 ISOERMINENTS |
| CN1489588A (en) | 2001-01-31 | 2004-04-14 | �Ʒ� | Thiazolyl-oxazolyl-pyrrolyl-and imidazolyl-acid amide derivatives useful as inbibitors of PDE 4 isozymes |
| CN102491959B (en) * | 2011-12-19 | 2015-03-25 | 江苏澄扬作物科技有限公司 | Preparation method of oxirane derivative |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4021478A (en) * | 1972-07-13 | 1977-05-03 | The Upjohn Company | Preparation of carboxylic acids from glycidonitriles with ionic lewis acids |
| NZ251092A (en) * | 1992-04-02 | 1996-12-20 | Smithkline Beecham Corp | 4-cyano-cyclohexane derivatives; medicaments; used in treating asthma |
| US5524438A (en) * | 1994-12-15 | 1996-06-11 | United Technologies Corporation | Segmented bulkhead liner for a gas turbine combustor |
| MY118813A (en) * | 1997-02-12 | 2005-01-31 | Smithkline Beecham Corp | Compounds and method for preparing substituted 4-phenyl-4-cyanocyclohexanoic acids |
| US6452022B1 (en) * | 1997-10-10 | 2002-09-17 | Smithkline Beecham Corporation | Method for preparing substituted 4-phenyl-4-cyanocyclohexanoic acids |
-
1998
- 1998-07-10 UA UA2000041944A patent/UA67753C2/en unknown
- 1998-10-02 MA MA25278A patent/MA24670A1/en unknown
- 1998-10-07 CA CA002305614A patent/CA2305614A1/en not_active Abandoned
- 1998-10-07 HU HU0003905A patent/HUP0003905A3/en not_active Application Discontinuation
- 1998-10-07 CN CNB988100304A patent/CN1192025C/en not_active Expired - Fee Related
- 1998-10-07 SK SK490-2000A patent/SK4902000A3/en unknown
- 1998-10-07 BR BR9814064-7A patent/BR9814064A/en not_active IP Right Cessation
- 1998-10-07 EA EA200000406A patent/EA003609B1/en not_active IP Right Cessation
- 1998-10-07 TR TR2000/00945T patent/TR200000945T2/en unknown
- 1998-10-07 AU AU96874/98A patent/AU741832B2/en not_active Ceased
- 1998-10-07 PL PL339759A patent/PL191974B1/en not_active IP Right Cessation
- 1998-10-07 ID IDW20000614A patent/ID25536A/en unknown
- 1998-10-07 EP EP98950965A patent/EP1043930A4/en not_active Withdrawn
- 1998-10-07 AR ARP980105002A patent/AR015952A1/en unknown
- 1998-10-07 UY UY25201A patent/UY25201A1/en not_active IP Right Cessation
- 1998-10-07 KR KR1020007003742A patent/KR100560038B1/en not_active IP Right Cessation
- 1998-10-07 IL IL13543498A patent/IL135434A/en not_active IP Right Cessation
- 1998-10-07 JP JP2000515437A patent/JP2001519363A/en active Pending
- 1998-10-07 DZ DZ980229A patent/DZ2619A1/en active
- 1998-10-07 WO PCT/US1998/021061 patent/WO1999018793A1/en not_active Application Discontinuation
- 1998-10-07 AP APAP/P/2000/001782A patent/AP1335A/en active
- 1998-10-07 NZ NZ503759A patent/NZ503759A/en unknown
- 1998-10-08 MY MYPI98004606A patent/MY122105A/en unknown
- 1998-10-09 PE PE1998000955A patent/PE121599A1/en not_active Application Discontinuation
- 1998-10-09 ZA ZA989228A patent/ZA989228B/en unknown
- 1998-12-01 TW TW087116680A patent/TW440557B/en not_active IP Right Cessation
-
1999
- 1999-01-26 SA SA99191000A patent/SA99191000A/en unknown
- 1999-05-25 UY UY25524A patent/UY25524A1/en not_active Application Discontinuation
-
2000
- 2000-04-05 BG BG104302A patent/BG104302A/en unknown
- 2000-04-06 NO NO20001777A patent/NO20001777L/en not_active Application Discontinuation
- 2000-04-07 OA OA1200000100A patent/OA11347A/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 109 | Application deemed to be withdrawn |
Effective date: 20110817 |