PE20001243A1 - SYNTHESIS OF USEFUL INTERMEDIARIES TO PREPARE TRICYCLIC COMPOUNDS - Google Patents
SYNTHESIS OF USEFUL INTERMEDIARIES TO PREPARE TRICYCLIC COMPOUNDSInfo
- Publication number
- PE20001243A1 PE20001243A1 PE1999001170A PE00117099A PE20001243A1 PE 20001243 A1 PE20001243 A1 PE 20001243A1 PE 1999001170 A PE1999001170 A PE 1999001170A PE 00117099 A PE00117099 A PE 00117099A PE 20001243 A1 PE20001243 A1 PE 20001243A1
- Authority
- PE
- Peru
- Prior art keywords
- compound
- prepare
- imine
- synthesis
- tricyclic compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 6
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000002466 imines Chemical class 0.000 abstract 3
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 abstract 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 229910004149 HFSO3 Inorganic materials 0.000 abstract 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 1
- 229910020667 PBr3 Inorganic materials 0.000 abstract 1
- 229910020656 PBr5 Inorganic materials 0.000 abstract 1
- 229910019213 POCl3 Inorganic materials 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 229910006121 SOBr2 Inorganic materials 0.000 abstract 1
- 229910006124 SOCl2 Inorganic materials 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical class C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 abstract 1
- 229910003074 TiCl4 Inorganic materials 0.000 abstract 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 abstract 1
- 102000004357 Transferases Human genes 0.000 abstract 1
- 108090000992 Transferases Proteins 0.000 abstract 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 abstract 1
- 229950008696 farnesil Drugs 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 abstract 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 abstract 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 abstract 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 abstract 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
SE REFIERE A UN PROCESO PARA PREPARAR UN COMPUESTO TRICICLICO DE FORMULA I, DONDE: R, R1, R2, R3 Y R4 SON H, Br, Cl, F, ALQUILO, ALCOXI; QUE COMPRENDE A)REACCIONAR UN COMPUESTO II, DONDE RA, RB, RC, RD Y RE SON H, HALO, ALQUILO, ALCOXI; R5 ES ARILO, HETEROARILO; CON UN DESHIDRATANTE PARA PRODUCIR UNA IMINA DE FORMULA III; LA MEZCLA DE REACCION SE PONE EN CONTACTO CON UN AGENTE ADICIONAL; B)HIDROLIZAR LA IMINA PARA PRODUCIR EL COMPUESTO I; EL DESHIDRATANTE PUEDE SER P2O5, P2O3, P2O3Cl4, POCl3, PCl3, PCl5, C6H6P(O)Cl2, PBr3, PBr5, SOCl2, SOBr2, COCl2 Y H2SO4; EL AGENTE ADICIONAL PUEDE SER AlCl3, FeCl3, ZnCl2, AlBr3, ZnBr2, TiCl4, SnCl4, CF3SO3H, HFSO3, HF/BF3, ENTRE OTROS. TAMBIEN SE REFIERE A COMPUESTOS INTERMEDIOS Y A LA IMINA DE FORMULA III. EL COMPUESTO I PUEDE SER UTIL COMO INTERMEDIARIO PARA PREPARAR COMPUESTOS ANTIHISTAMINICOS O INHIBIDORES DE FARNESIL TRANSFERASAIT REFERS TO A PROCESS TO PREPARE A TRICYCLE COMPOUND OF FORMULA I, WHERE: R, R1, R2, R3 AND R4 ARE H, Br, Cl, F, ALKYL, ALCOXY; WHICH INCLUDES A) REACTING A COMPOUND II, WHERE RA, RB, RC, RD AND RE ARE H, HALO, ALKYL, ALCOXI; R5 IS ARYL, HETEROARYL; WITH A DEHYDRATOR TO PRODUCE AN IMINE OF FORMULA III; THE REACTION MIXTURE IS CONTACTED WITH AN ADDITIONAL AGENT; B) HYDROLIZE THE IMINE TO PRODUCE COMPOUND I; THE DEHYDRATOR CAN BE P2O5, P2O3, P2O3Cl4, POCl3, PCl3, PCl5, C6H6P (O) Cl2, PBr3, PBr5, SOCl2, SOBr2, COCl2 AND H2SO4; THE ADDITIONAL AGENT MAY BE AlCl3, FeCl3, ZnCl2, AlBr3, ZnBr2, TiCl4, SnCl4, CF3SO3H, HFSO3, HF / BF3, AMONG OTHERS. ALSO REFERS TO INTERMEDIATE COMPOUNDS AND THE IMINE OF FORMULA III. COMPOUND I MAY BE USED AS AN INTERMEDIARY TO PREPARE ANTIHISTAMINE COMPOUNDS OR INHIBITORS OF FARNESIL TRANSFERASE
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19700398A | 1998-11-20 | 1998-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20001243A1 true PE20001243A1 (en) | 2000-11-15 |
Family
ID=22727622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE1999001170A PE20001243A1 (en) | 1998-11-20 | 1999-11-19 | SYNTHESIS OF USEFUL INTERMEDIARIES TO PREPARE 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 |
| DE3677842D1 (en) * | 1985-05-13 | 1991-04-11 | Schering Corp | METHOD FOR THE PRODUCTION OF PIPERIDYLIDES-DIHYDRODIBENZO (A, D) CYCLOHEPTENES AND THEIR AZODERIVATES, COMPOUNDS MADE THEREOF AND THEIR USE FOR THE PREPARATION OF MEDICINAL PRODUCTS. |
| 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 |
| CA2358394C (en) | 1995-12-22 | 2006-05-02 | Schering Corporation | Tricyclic amides useful for inhibition of g-protein function and for treatment of proliferative diseases |
| SI0806415T1 (en) * | 1996-05-09 | 2000-04-30 | Lonza Ag | Process for the preparation of 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 |
| EP0977739B1 (en) * | 1997-03-25 | 2003-10-29 | Schering Corporation | Synthesis of intermediates useful in preparing tricyclic compounds |
-
1999
- 1999-11-18 CA CA002351693A patent/CA2351693C/en not_active Expired - Lifetime
- 1999-11-18 AR ARP990105868A patent/AR028138A1/en active IP Right Grant
- 1999-11-18 EP EP99972525A patent/EP1131296A2/en not_active Withdrawn
- 1999-11-18 WO PCT/US1999/026010 patent/WO2000030589A2/en active Application Filing
- 1999-11-18 TW TW088120161A patent/TW509680B/en not_active IP Right Cessation
- 1999-11-18 CN CNB998135151A patent/CN1162404C/en not_active Expired - Lifetime
- 1999-11-18 CO CO99072692A patent/CO5150169A1/en unknown
- 1999-11-18 JP JP2000583474A patent/JP4663122B2/en not_active Expired - Lifetime
- 1999-11-18 AU AU37902/00A patent/AU3790200A/en not_active Abandoned
- 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 |
|---|---|
| WO2000030589A2 (en) | 2000-06-02 |
| JP2002530307A (en) | 2002-09-17 |
| JP2010132701A (en) | 2010-06-17 |
| WO2000030589A3 (en) | 2001-01-04 |
| AU3790200A (en) | 2000-06-13 |
| CN1162404C (en) | 2004-08-18 |
| HK1038698A1 (en) | 2002-03-28 |
| CO5150169A1 (en) | 2002-04-29 |
| CN1326444A (en) | 2001-12-12 |
| CA2351693A1 (en) | 2000-06-02 |
| EP1131296A2 (en) | 2001-09-12 |
| JP4663122B2 (en) | 2011-03-30 |
| AR028138A1 (en) | 2003-04-30 |
| ZA200103246B (en) | 2002-07-22 |
| TW509680B (en) | 2002-11-11 |
| CA2351693C (en) | 2009-01-20 |
| MY121795A (en) | 2006-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant, registration | ||
| FD | Application declared void or lapsed |