Process for producing carbostyril derivatives

Details Process for producing carbostyril derivatives Process for producing carbostyril derivatives

2008-07-15

2008-07-15

Seaman, D. Margaret (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S157000

Reexamination Certificate

active

10208738

ABSTRACT:
The present invention provides a process for producing carbostyril derivatives (I) which are known to be useful as medical drug such as antithrombotic agent, cerebral circulation improver, anti-inflammatory agent, antiulcer agent, etc. in a high yield and a high purity. The carbostyril derivatives (I) can be produced by reacting a carbostyril derivative (II) with a tetrazole derivative (III) in the presence of a phase transfer catalyst.

REFERENCES:
patent: 4277429 (1981-07-01), Okita
patent: 4277479 (1981-07-01), Nishi et al.
patent: 5202323 (1993-04-01), Tanikawa et al.
patent: 6388080 (2002-05-01), Stowell et al.
patent: 6515128 (2003-02-01), Mendelovici et al.
patent: 6525201 (2003-02-01), Mendelovici et al.
patent: 6630590 (2003-10-01), Aki et al.
patent: 6657061 (2003-12-01), Stowell et al.
patent: 6740758 (2004-05-01), Mendelovici et al.
patent: 7026486 (2006-04-01), Yamamoto et al.
patent: 7060833 (2006-06-01), Mendelovici et al.
patent: 2002/0099213 (2002-07-01), Mendelovichi et al.
patent: 2005/0065343 (2005-03-01), Mendelovici et al.
patent: 2005/0101631 (2005-05-01), Aki et al.
patent: 2005/0222202 (2005-10-01), Naddaka et al.
patent: 2006/0100437 (2006-05-01), Aki et al.
patent: 8702401 (1987-03-01), None
patent: 56045414 (1981-04-01), None
patent: 56046810 (1981-04-01), None
patent: 56-49378 (1981-05-01), None
patent: 56049378 (1981-05-01), None
patent: 58059980 (1983-04-01), None
patent: 58077880 (1983-05-01), None
patent: 1265051 (1989-10-01), None
patent: 6100487 (1994-04-01), None
patent: 11152243 (1999-06-01), None
patent: 2000229953 (2000-08-01), None
patent: 01/03803 (2001-05-01), None
patent: WO 00/57881 (2000-10-01), None
patent: WO 02/14283 (2002-02-01), None
patent: WO 2/14283 (2002-02-01), None
Nishi, CA 99:98806, 1983.
Nishi, CA 103:141893, 1985.
U.S. Appl. No. 11/833,592, filed Aug. 2007, Akie et al.
Chin-Hsien et al., “The Use of Phase-Transfer Catalysis For The Synthesis of Phenyl and 8-Quinolinyl Ethers,” Synthesis, pp. 858-861 (1982).
G. Bram et al., “Solid-Liquid Phase Transfer Catalysis Without Solvent: A Mild And Efficient Preparation Of Mono And Di-Ethers Derived From 8-Hydroxyquinoline,” Synthetic Communications, 14(9), pp. 889-898 (1984).
Japanese Pharmaceutical Codex, p. 836-839 (1997) (Partial English translation is attached thereto).
The Merck Index, p. 382 (1996).
A.P. Bashall et al., “A Convenient, High-Yielding Method For The Methylenation of Catechols,” Tetrahedron Letters, No. 40, pp. 3489-3490 (1975).
U.S. Appl. No. 60/225,362, “Novel synthesis for preparing cilostazol”, Mendelovichi, M. et al., Aug. 14, 2002.
U.S. Appl. No. 10/208,740, “Process for producing carbostyril derivatives”, Aki, S. et al., Aug. 1, 2002.
Starks; Liotta;Phase Transfer Catalysis, Academic Press: NY, 1978, pp. 128-138.
Weber; Gokel;Phase Transfer Catalysis in Organic Synthesis, Springer: NY, 1977, pp. 73-84.
A. Mckillop; J.C. Fiaud; R.P. Hug,Tetrahedron, vol. 30, p. 1379-1382 (1974).
P.M. Quan; S.R. Kron,C.A.vol. 86, 189 480 (1977).
J.D. Reinheimer, J.P. Douglass, H. Leister, M.B. Voelkel,J. Org. Chem., vol. 22, p. 1743-1745 (1957).
B.R. Baker, F.J. McEvoy,J. Org. Chem., vol. 20, p. 136-142 (1955).
A. Cohen, J.W. Haworth, E.H. Hughes,J. Chem. Soc., p. 4374-4383 (1952).
J. Ugelstad, T. Ellingsen, A. Berge,Acta Chem. Scand. vol. 20, p. 1593-1598 (1966).
R.L. Merker, M.J. Scott,J. Org. Chem. vol. 26, p. 5180-5182 (1961).
J. March,Advanced Organic Chemistry, Fourth Edition, John Wiley & Sons: NY, 1992, pp. 362-365, pp. 386-387.
T. Nishi et al., “Studies on 2-oxoquinoline Derivatives as Blood Platelet Aggregation Inhibitors. I. alkyl 4-(2-Oxo-1, 2, 3, 4-tetrahydro-6-quinolyloxy)butyrates and related compounds”, Chem. Pharm. Bull., vol. 31, No. 3, pp. 798-810, (1983).
Nishi et al.; “Studies on 2-Oxoquinoline Derivatives as Blood Platelet Aggregation Inhibitors. II. 6-[3-(1-Cyclohexyl-5-Tetrazolyl)Propoxy]-1,2-Dihydro-2-Oxoquinoline and Related Compounds”; Chem. Pharm. Bull., vol. 31, No. 4, pp. 1151-1157, (1983).
Freedman et al.; “An Improved Williamson Ether Synthesis Using Phase Transfer Catalysis”; Tetrahedron Letters No. 38, pp. 3251-3254, 1975.
Office Action dated Mar. 30, 2007, in co-pending U.S. Appl. No. 11/017,495.
Office Action dated Apr. 3, 2007, in co-pending U.S. Appl. No. 11/318,104.
Freedman et al., An Improved Williamson Ether Synthesis Using Phase Transfer Catalysis,Tetrahedron Letters, No. 38, pp. 3251-3254, 1975.
Nishi et al., Studies on 2-Oxoquinoline Derivatives as Blood Platelet Aggregation Inhibitors. II. 6-[3(1-Cyclohexyl-5-Tetrazolyl) Propoxy]-1,2-Dihydro-2-Oxyoquinoline and Related Compounds,Chem. Pharm. Bull., vol. 31, No. 4, pp. 1151-1157, 1982.
Office Action dated Dec. 18, 2002, in abandoned U.S. Appl. No. 09/869,264.
Office Action dated Mar. 10, 2003, in granted U.S. Appl. No. 10/208,740.
Notice of Allowance dated Jun. 26, 2003, in granted U.S. Appl. No. 10/208,740.
Office Action dated Jun. 21, 2004, in abandoned U.S. Appl. No. 10/670,599.
U.S. Appl. No. 11/833,592, “Process for producing carbostyril derivatives”, Aki et al., Aug. 3, 2007.
H.H. Freedman et al., “An Improved Williamson Ether Synthesis Using Phase Transfer Catalysis,” Tetrahedron Letters No. 38, pp. 3251-3254, 1975.
T. Nishi et al., “Studies on 2-Oxoquinoline Derivatives as Blood Platelet Aggregation Inhibitors. II. 6-[3(1-Cyclohexyl-5-tetrazolyl) Propoxy]-1,2-Dihydro-2-Oxoquinoline and Related Compounds”, Chem. Pharm. Bull., vol. 31, No. 4, pp. 1151-1157, (1982).
The Summary of the 29thSymposium on the Chemistry of Natural Products, pp. 41-43 (1994) (English translation of the Certificate and partial English translation are attached thereto.).
Chin-Hsien et al., “The Use of Phase-Transfer Catalysis For The Synthesis of Phenyl and 8-Quinolinyl Ethers,” Synthesis, pp. 858-861 (1982).
G. Bram et al., “Solid-Liquid Phase Transfer Catalysis Without Solvent: A Mild And Efficient Preparation Of Mono and Di-Ethers Derived From 8-Hydroxyquinoline,” Synthetic Communications, 14(9), pp. 889-898 (1984).
Japanese Pharmaceutical Codex, pp. 836-839 (1997) (Partial English translation is attached thereto.).
The Merck Index, p. 382 (1996).
A.P. Bashall et al., “A Convenient, High-Yielding Method For The Methylenation of Catechols,” Tetrahedron Letters, No. 40, pp. 3489-3490 (1975).
U.S. Appl. No. 60/225,362, “Novel synthesis for preparing cilostazol”, Mendelovichi, M. et al., Aug. 14, 2002.
U.S. Appl. No. 10/208,740, “Process for producing carbostyril derivatives”, Aki, S. et al., Aug. 1, 2002.
The Summary of the 29thSymposium on the Chemistry of Natural Products, pp. 41-43 (1994) (full English translation).
Japanese Pharmaceutical Codex, p. 836839 (1997) (full English translation).
Nishi, CA 103:141893, abstract of Chem&Pharm Bull, 1985, 33(3), pp. 1140-1147.
Nishi, CA 99:98806, abstract of Chem&Pharm Bull, 1983, 31(4), pp. 1151-1157.
The Summary of the 29thSymposium on the Chemistry of Natural Products, pp. 41-43 (1994) (English translation of the Certificate and partial English translation).
The Summary of the 29thSymposium on the Chemistry of Natural Products, pp. 41-43 (1994) (full English translation).
Japanese Pharmaceutical Codex 1997, pp. 836-838 (1997) (full English translation).
Nishi et al., CA 103:141893, abstract ofChem. Pharm. Bull., 33(3):1140-1147 (1985).

Affiliated with

Also associated with

Rating

Process for producing carbostyril derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for producing carbostyril derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for producing carbostyril derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3945824