Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2005-05-31
2005-05-31
McKenzie, Thomas C. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C544S293000
Reexamination Certificate
active
06900221
ABSTRACT:
The present invention relates to a stable crystalline form of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine hydrochloride designated the B polymorph, its production in essentially pure form, and its use. The invention also relates to the pharmaceutical compositions containing the stable polymorph B form of N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine as hydrochloride, as well other forms of the compound, and to methods of treating hyperproliferative disorders, such as cancer, by administering the compound.
REFERENCES:
patent: 3800039 (1974-03-01), Marquis et al.
patent: 4139561 (1979-02-01), Onopchenko et al.
patent: 4216341 (1980-08-01), Onopchenko et al.
patent: 4219679 (1980-08-01), Onopchenko et al.
patent: 4255313 (1981-03-01), Antonoplos et al.
patent: 4281127 (1981-07-01), LeMahieu et al.
patent: 4305751 (1981-12-01), Sabourin et al.
patent: 4322420 (1982-03-01), Kobayashi et al.
patent: 4943533 (1990-07-01), Mendelsohn et al.
patent: 5089499 (1992-02-01), Barker et al.
patent: 5214144 (1993-05-01), Tai et al.
patent: 5256781 (1993-10-01), Primeau et al.
patent: 5457105 (1995-10-01), Barker
patent: 5475001 (1995-12-01), Barker
patent: 5580870 (1996-12-01), Barker
patent: 5616582 (1997-04-01), Barker
patent: 5639881 (1997-06-01), Skibo et al.
patent: 5654307 (1997-08-01), Bridges et al.
patent: 5686458 (1997-11-01), Lee et al.
patent: 5707992 (1998-01-01), Webber et al.
patent: 5710145 (1998-01-01), Engel et al.
patent: 5747498 (1998-05-01), Schnur et al.
patent: 5770195 (1998-06-01), Hudziak et al.
patent: 5817674 (1998-10-01), Clemence et al.
patent: 5821246 (1998-10-01), Brown et al.
patent: 5948784 (1999-09-01), Fujiwara et al.
patent: 6004967 (1999-12-01), McMahon et al.
patent: 6004979 (1999-12-01), Clemence et al.
patent: 6130218 (2000-10-01), Morsdorf et al.
patent: 6169091 (2001-01-01), Cockerill et al.
patent: 6476040 (2002-11-01), Norris et al.
patent: 6706721 (2004-03-01), Allen et al.
patent: 2002/0061304 (2002-05-01), Miller et al.
patent: 1842292 (1992-06-01), None
patent: 3101093 (1993-01-01), None
patent: 3813095 (1995-11-01), None
patent: 2086968 (1992-11-01), None
patent: 20003974 (2001-05-01), None
patent: 2936705 (1979-09-01), None
patent: 0498723 (1992-02-01), None
patent: 0520722 (1992-12-01), None
patent: 0566226 (1993-01-01), None
patent: 0579496 (1994-01-01), None
patent: 0602851 (1994-06-01), None
patent: 0635498 (1995-01-01), None
patent: 0635507 (1995-01-01), None
patent: 0667165 (1995-08-01), None
patent: 0787722 (1997-08-01), None
patent: 0837063 (1998-04-01), None
patent: 1044969 (2000-10-01), None
patent: 6205969 (1985-07-01), None
patent: 1048048 (1989-02-01), None
patent: 5208911 (1992-06-01), None
patent: 7309873 (1992-11-01), None
patent: 6192235 (1993-07-01), None
patent: 8099962 (1993-07-01), None
patent: 7101941 (1993-09-01), None
patent: 6336481 (1993-12-01), None
patent: 7118266 (1994-01-01), None
patent: 0673025 (1994-03-01), None
patent: 7126255 (1994-09-01), None
patent: 8151377 (1994-11-01), None
patent: 7188244 (1995-07-01), None
patent: 9165385 (1995-08-01), None
patent: 9221478 (1997-02-01), None
patent: 10036325 (1998-02-01), None
patent: 10036326 (1998-02-01), None
patent: 0245662 (1993-01-01), None
patent: 2127263 (1993-01-01), None
patent: WO9220642 (1992-11-01), None
patent: WO9503283 (1995-02-01), None
patent: WO9515758 (1995-06-01), None
patent: WO9609294 (1996-03-01), None
patent: WO9615118 (1996-05-01), None
patent: WO9625422 (1996-08-01), None
patent: 9628430 (1996-09-01), None
patent: WO9630347 (1996-10-01), None
patent: WO9640210 (1996-12-01), None
patent: WO9703069 (1997-01-01), None
patent: WO9730035 (1997-08-01), None
patent: WO9732856 (1997-09-01), None
patent: WO9738983 (1997-10-01), None
patent: WO9741896 (1997-11-01), None
patent: WO9813354 (1998-04-01), None
patent: WO9903803 (1999-01-01), None
patent: WO9955683 (1999-11-01), None
patent: WO9960023 (1999-11-01), None
patent: WO0031048 (2000-02-01), None
patent: WO134574 (2001-05-01), None
patent: WO0170255 (2001-09-01), None
Agharkar, S., et al., “Enhancement of Solubility of Drug Salts by Hydrophilic Counterions: Properties of Organic Salts of an Antimalarial Drug,”Journal of Pharmaceutical Sciences1976, vol. 65, No. 5, p.p. 747-749 (Exhibit 73).
Berge, S., et al., “Pharmaceutical Salts,”Journal of Pharmaceutical Sciences1977, vol. 66, No. 1, p.p. 1-19 (Exhibit 74).
Bleicher, L., et al., “Aryl- and Hetero-Alkyne Coupling Reactions Catalyzed by Palladium on Carbon and CuI inan Aqueous Medium,”Synlett1995, Nov., p.p. 1115-1116 (Exhibit 75).
Bleicher, L., et al., “A Practical and Efficient Synthesis of the Selective Neuronal Acetylcholine-Gated Ion Agonist (S)-(-)-5-Ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine Maleate (SIB-1508Y),”Journal of Organic Chemistry1998, vol. 63, No. 4, p.p. 1109-1118 (Exhibit 76).
Botros, S., et al., “Synthesis of Certain Nitro-quinazoline Derivatives Structurally Related to Some Chemotherapeutic Agents,”Egypt. J. Pharm. Sci.1972, vol. 13, No. 1, p.p. 11-21 (Exhibit 77).
Cerny, A., “Solvolysis of Some 1-(8a-ergolyinyl)-3,3-Diethylureas and Their Salts,”Collection-Czechoslovak Chem. Commun.1987, vol. 52, p.p. 1331-1339 (Exhibit 78).
Smaill, J., et al., “Tyrosine Kinase Inhibitors. 17. Irreversible Inhibitors of the Epidermal Growth Factor Receptor: 4-(Phenylamino)quinazoline- and 4-(Phenylamino)pyrido[3,2-d]pyrimidine-6-acrylamides Bearing Additional Solubilizing Functions,”J. Med. Chem.2000, vol. 43, p.p. 1380-1397 (Exhibit 85).
Spurlock, C., “Increasing Solubility of Enoxacin and Norfloxacin by Means Salt Formation,”Journal of Parenteral Science and Technology1986, vol. 40, No. 2, p.p. 70-72 (Exhibit 86).
Takalo, H., et al., “Synthesis of Some Substituted Dimethyl and Diethyl 4-(Phenylethynyl)-2,6-pyridine- dicarboxylates,”Acta Chemica Scandinavica, vol. B42, p.p. 448-454 (Exhibit 87).
Pollack, V., et al., “Inhibition of Epidermal Growth Factor Receptor-Associated Tyrosine Phosphorylation in Human Carcinomas with CP-358,774: Dynamics of Receptor Inhibition In Situ and Antitumor Effects in Athymic Mice,”Journal of Pharmacology and Experimental Therapeutics, 1999, vol. 291, No. 2, p.p. 739-748 (Exhibit 83).
Rosenberg, S., et al., “Studies Directed toward the Design of Orally Active Renin Inhibitors. 2. Development of the Efficacious, Bioavailable Renin Inhibitor (2S)-2-Benzyl-3-[[(1-methylpiperazin-4-yl)sulfonyl]propionyl]-3-thiazol-4-yl-L-alanine Amide of (2S, 3R, 4S)-2-Amino-1-cyclohexyl-3,4-dihydorxy-6-methylheptane (A-72517),”J. Med. Chem.1993, vol. 36, p.p. 460-467 (Exhibit 84).
Hussain, M., et al., “Parenteral Formulation of the Kappa Agonist Analgesic, DuP 747, via Micellar Solubilization,”Pharmaceutical Research1992, vol. 9, No. 6, p.p. 750-752 (Exhibit 79).
Moyer, J., et al., “Induction of Apoptosis and Cell Cycle Arrest by CP-358,774, an Inhibitor of Epidermal Growth Factor Receptor Tyrosine Kinase,”Cancer Research1997, vol. 57, p.p. 4838-4848 (Exhibit 80).
Norris, T., et al., “Discovery of a New Stable Polymorph of 4-(3-ethynylphenylamino)-6,7-bis(2-methoxy-ethoxy)quinazolinium Methanesulfonate Using Near-Infrared Spectroscopy to Monitor Form Change Kinetics,”J. Chem. Soc., Perkin Trans.2000, vol. 2, p.p. 1233-1236 (Exhibit 81).
Onopchenko, et al., “Selective Catalytic Hydrogenation of Aromatic Nitro Groups in the Presence of Acetylenes. Synthesis of (3-Aminophenyl)acetylene via Hydrogenation of Dimethylcarbinol Substituted (3-Nitrophenyl) acetylene over Heterogeneous Metallic Ruthenium Catallyst,”Journal of Organic Chemistry1979, vol. 44, No. 8, p.p. 1233-1236 (Exhibit 82).
Melissaris, A.P. et al., “A Simple and Economical Synthetic Route top-Ethynylaniline and Ethynyl-Terminated Substrates” (1994)J. Org. Chem.59:5818-5821 (Exhibit 16).
Montalbetti, C. et al., “A Convergent Synthesis of Functionalized B-seco Taxane Skeletons” (1995)Tetrahedron Lette
Connell Richard D.
Ferrante Karen J.
Foster Barbara A.
Kajiji Shama M.
Morin Michael J.
Cooper & Dunham LLP
McKenzie Thomas C.
OSI Pharmaceuticals, Inc.
White John P.
LandOfFree
Stable polymorph on N-(3-ethynylphenyl)-6, 7-bis... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Stable polymorph on N-(3-ethynylphenyl)-6, 7-bis..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Stable polymorph on N-(3-ethynylphenyl)-6, 7-bis... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3454349