CA2351693A1 - Synthesis of intermediates useful in preparing tricyclic compounds - Google Patents
Synthesis of intermediates useful in preparing tricyclic compounds Download PDFInfo
- Publication number
- CA2351693A1 CA2351693A1 CA002351693A CA2351693A CA2351693A1 CA 2351693 A1 CA2351693 A1 CA 2351693A1 CA 002351693 A CA002351693 A CA 002351693A CA 2351693 A CA2351693 A CA 2351693A CA 2351693 A1 CA2351693 A1 CA 2351693A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- preparing
- heteroaryl
- alkoxy
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
Abstract
Disclosed is a process for preparing a com-pound having formula (I): wherein R, R1, R2, R3, and R4 are independently selected from the group con-sisting of H, Br, Cl, F, alkyl, or alkoxy, by (A) reacting a compound having formula (II), wherein R A, R B, R C, R D, and R E are independently se-lected from the group consisting of H, halo, alkyl, or alkoxy, and R5 is aryl or heteroaryl, with a de-hydrating agent to produce an imine having for-mula (IIa); and (B) hydrolyzing the imine produced in step (A) to produce the compound having for-mula (I). Also disclosed are novel intermediates hav-ing a formula (IIb), wherein R A, R B, R C, R D, and R E are independently selected from the group con-sisting of H, halo, alkyl, or alkoxy, and R5 is aryl or heteroaryl. Also disclosed is a process for preparing a compound having formula (III), com-prising: reacting a compound having formula (IV) with NH2R5 in the presence of a palladium cata-lyst, carbon monoxide, a base, and an ether selected from the group consisting of: CH3OCH2CH2OCH3;
CH3OCH2CH2OCH2CH2OCH3; and CH3OCH2CH2OCH2CH2OCH2CH2OCH3, wherein X is H, Br, Cl, or F, and R5 is aryl or heteroaryl.
The compounds made by these processes are useful intermediates for preparing compounds that are antihistamines or inhibitors of farnesyl protein transferase.
CH3OCH2CH2OCH2CH2OCH3; and CH3OCH2CH2OCH2CH2OCH2CH2OCH3, wherein X is H, Br, Cl, or F, and R5 is aryl or heteroaryl.
The compounds made by these processes are useful intermediates for preparing compounds that are antihistamines or inhibitors of farnesyl protein transferase.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19700398A | 1998-11-20 | 1998-11-20 | |
| US09/197,003 | 1998-11-20 | ||
| PCT/US1999/026010 WO2000030589A2 (en) | 1998-11-20 | 1999-11-18 | Synthesis of intermediates useful in preparing tricyclic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2351693A1 true CA2351693A1 (en) | 2000-06-02 |
| CA2351693C CA2351693C (en) | 2009-01-20 |
Family
ID=22727622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002351693A Expired - Lifetime CA2351693C (en) | 1998-11-20 | 1999-11-18 | Synthesis of intermediates useful in preparing tricyclic compounds |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1131296A2 (en) |
| JP (2) | JP4663122B2 (en) |
| CN (1) | CN1162404C (en) |
| AR (1) | AR028138A1 (en) |
| AU (1) | AU3790200A (en) |
| CA (1) | CA2351693C (en) |
| CO (1) | CO5150169A1 (en) |
| HK (1) | HK1038698A1 (en) |
| MY (1) | MY121795A (en) |
| PE (1) | PE20001243A1 (en) |
| TW (1) | TW509680B (en) |
| WO (1) | WO2000030589A2 (en) |
| ZA (1) | ZA200103246B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004501081A (en) | 2000-04-18 | 2004-01-15 | シェーリング コーポレイション | Synthesis of intermediates useful in the preparation of tricyclic compounds |
| WO2004058719A1 (en) * | 2002-12-26 | 2004-07-15 | Cadila Healthcare Limited | A process for preparing benzocyclohetapyridin-11-ones |
| CN108218773A (en) * | 2018-02-28 | 2018-06-29 | 朱路英 | A kind of method for preparing resisting allergic rhinitis drug loratadine intermedite |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4282233B1 (en) | 1980-06-19 | 2000-09-05 | Schering Corp | Antihistaminic 11-(4-piperidylidene)-5h-benzoÄ5,6Ü-cyclohepta-Ä1,2Ü-pyridines |
| US4731447A (en) * | 1985-05-13 | 1988-03-15 | Schering Corporation | Process for preparing piperidylidene dihydro-dibenzo(a,d)-cycloheptenes or aza-derivatives thereof |
| EP0208855B1 (en) * | 1985-05-13 | 1991-03-06 | Schering Corporation | process for preparing piperidylidene dihydrodibenzo(a,d)cycloheptenes and aza derivatives thereof, compounds obtained by such process and the use of such compounds for preparing useful pharmaceutical compositions |
| US5089496A (en) | 1986-10-31 | 1992-02-18 | Schering Corporation | Benzo[5,6]cycloheptapyridine compounds, compositions and method of treating allergies |
| CA2245055C (en) * | 1989-02-28 | 2003-03-25 | F. Hoffmann-La Roche Ag | Amidation of pyridines |
| US5672750A (en) * | 1994-12-16 | 1997-09-30 | Eastman Chemical Company | Preparation of aromatic amides from carbon monoxide, an amine and an aromatic chloride |
| IL117798A (en) * | 1995-04-07 | 2001-11-25 | Schering Plough Corp | Tricyclic compounds useful for inhibition of g-protein function and for treatment of proliferative diseases and pharmaceutical compositions comprising them |
| CN1326847C (en) | 1995-12-22 | 2007-07-18 | 先灵公司 | Tricyclic amides useful for inhibition of G-protein function and for treatment of proliferative diseases |
| ATE189815T1 (en) * | 1996-05-09 | 2000-03-15 | Lonza Ag | METHOD FOR PRODUCING ARYLAMIDES OF HETEROAROMATIC CARBOXYLIC ACIDS |
| US5958890A (en) * | 1996-09-13 | 1999-09-28 | Schering Corporation | Tricyclic compounds useful for inhibition of G-protein function and for treatment of proliferative diseases |
| DE69819316T2 (en) * | 1997-03-25 | 2004-07-22 | Schering Corp. | SYNTHESIS OF INTERMEDIATE PRODUCTS APPLICABLE IN THE PRODUCTION OF TRICYCLIC COMPOUNDS |
-
1999
- 1999-11-18 AU AU37902/00A patent/AU3790200A/en not_active Abandoned
- 1999-11-18 WO PCT/US1999/026010 patent/WO2000030589A2/en active Application Filing
- 1999-11-18 JP JP2000583474A patent/JP4663122B2/en not_active Expired - Lifetime
- 1999-11-18 CA CA002351693A patent/CA2351693C/en not_active Expired - Lifetime
- 1999-11-18 CO CO99072692A patent/CO5150169A1/en unknown
- 1999-11-18 EP EP99972525A patent/EP1131296A2/en not_active Withdrawn
- 1999-11-18 CN CNB998135151A patent/CN1162404C/en not_active Expired - Lifetime
- 1999-11-18 AR ARP990105868A patent/AR028138A1/en active IP Right Grant
- 1999-11-18 TW TW088120161A patent/TW509680B/en not_active IP Right Cessation
- 1999-11-19 PE PE1999001170A patent/PE20001243A1/en not_active Application Discontinuation
- 1999-11-19 MY MYPI99005048A patent/MY121795A/en unknown
-
2001
- 2001-04-20 ZA ZA200103246A patent/ZA200103246B/en unknown
-
2002
- 2002-01-14 HK HK02100248.8A patent/HK1038698A1/en unknown
-
2010
- 2010-03-01 JP JP2010044749A patent/JP2010132701A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010132701A (en) | 2010-06-17 |
| JP2002530307A (en) | 2002-09-17 |
| CN1162404C (en) | 2004-08-18 |
| AR028138A1 (en) | 2003-04-30 |
| CA2351693C (en) | 2009-01-20 |
| CO5150169A1 (en) | 2002-04-29 |
| AU3790200A (en) | 2000-06-13 |
| TW509680B (en) | 2002-11-11 |
| CN1326444A (en) | 2001-12-12 |
| MY121795A (en) | 2006-02-28 |
| WO2000030589A3 (en) | 2001-01-04 |
| EP1131296A2 (en) | 2001-09-12 |
| ZA200103246B (en) | 2002-07-22 |
| JP4663122B2 (en) | 2011-03-30 |
| HK1038698A1 (en) | 2002-03-28 |
| WO2000030589A2 (en) | 2000-06-02 |
| PE20001243A1 (en) | 2000-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20191118 |