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Patent US7662835 - Methods of treating allergic reactions using an anhydrous form of ... - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inPatentsThe present invention is related to novel processes for preparing anhydrous and hydrated forms of piperidine derivatives, polymorphs and pseudomorphs thereof of the formulas which are useful as antihistamines, antiallergic agents and bronchodilators....http://www.google.com/patents/US7662835?utm_source=gb-gplus-sharePatent US7662835 - Methods of treating allergic reactions using an anhydrous form of antihistaminic piperidine derivativesAdvanced Patent SearchTry the new Google Patents, with machine-classified Google Scholar results, and Japanese and South Korean patents.Publication numberUS7662835 B2Publication typeGrantApplication numberUS 11/534,839Publication dateFeb 16, 2010Filing dateSep 25, 2006Priority dateMay 18, 1994Fee statusPaidAlso published asCA2189007A1, CA2189007C, CA2449419A1, CA2449419C, CA2585705A1, CA2585705C, CN1148849A, CN1623985A, CN1907967A, CN1907967B, DE69527429D1, DE69527429T2, EP0766668A1, EP0766668B1, EP1178041A1, EP2354125A1, US7135571, US7138524, US7666881, US20010012896, US20010014741, US20010025106, US20020193600, US20020193601, US20020193603, US20030045721, US20040014976, US20070021461, US20070021462, US20080167469, US20080167471, WO1995031437A1Publication number11534839, 534839, US 7662835 B2, US 7662835B2, US-B2-7662835, US7662835 B2, US7662835B2InventorsFrederick J. McCarty, Albert A. CarrOriginal AssigneeAventis Holdings, Inc.Export CitationBiBTeX, EndNote, RefManPatent Citations (40), Non-Patent Citations (189), Referenced by (1), Classifications (16), Legal Events (6) External Links: USPTO, USPTO Assignment, EspacenetMethods of treating allergic reactions using an anhydrous form of antihistaminic piperidine derivatives
US 7662835 B2Abstract
Preparation of Form II 4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylbenzeneacetic acid hydrochloride
Preparation of Form IV 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylbenzeneacetic acid hydrochloride (Form IV)
Conversion of Form II to Form I 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]- , -dimethylbenzeneacetic acid hydrochloride (Form I)
Conversion of Form II to Form I 4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylbenzeneacetic acid hydrochloride
Conversion of Form I to Form II 4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-, -dimethylbenzeneacetic acid hydrochloride hydrate
Conversion of Form II into Form III 4-[4-[4-Hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylbenzeneacetic acid hydrochloride (Form III)
Conversion of Form III into Form I 4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]1-hydroxybutyl]-α,α-dimethylbenzeneacetic acid hydrochloride (Form I)
Conversion of Form IV into Form I 4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-α,α-dimethylbenzeneacetic acid hydrochloride (Form I)
Patent CitationsCited PatentFiling datePublication dateApplicantTitleUS3448152Nov 3, 1966Jun 3, 1969Jefferson Chem Co IncAmine recoveryUS3862173Jan 28, 1972Jan 21, 1975Richardson Merrell IncOlefinic 4-substituted piperidino derivativesUS3878217Jul 12, 1973Apr 15, 1975Richardson Merrell IncAlpha-aryl-4-substituted piperidinoalkanol derivativesUS3965257Jan 28, 1974Jun 22, 1976Richardson-Merrell Inc.Compositions and methods for the treatment of the symptoms of histamine induced allergic reactionsUS4254129 *Apr 10, 1979Mar 3, 1981Richardson-Merrell Inc.Piperidine derivativesUS4254130Apr 10, 1979Mar 3, 1981Richardson-Merrell Inc.Piperidine derivativesUS4285957Oct 14, 1980Aug 25, 1981Richardson-Merrell Inc.1-Piperidine-alkanol derivatives, pharmaceutical compositions thereof, and method of use thereofUS4285958Oct 14, 1980Aug 25, 1981Richardson-Merrell Inc.1-Piperidine-alkylene ketones, pharmaceutical compositions thereof and method of use thereofUS4672133Mar 18, 1985Jun 9, 1987Glaxo Group LimitedProcess for forming Form 2 ranitidine hydrochlorideUS4742175Jun 30, 1987May 3, 1988Merrell Dow Pharmaceuticals Inc.Preparation of polymorphically pure terfenadineUS5204249Oct 25, 1991Apr 20, 1993Merck Patent Gesellschaft Mit Beschrankter HaftungProcess for the preparation of carebastine and similar materialsUS5308840Apr 6, 1992May 3, 1994Green Cross CorporationSubstituted or unsubstituted benzhydryl heteroalkyl-substituted aminophenol compounds and pharmaceutical compositions thereofUS5375693Feb 2, 1994Dec 27, 1994Sepracor, Inc.Methods and compositions for treating allergic disorders and other disorders metabolic derivatives of terfenadineUS5574045 *Jun 6, 1995Nov 12, 1996Hoechst Marion Roussel, Inc.Oral pharmaceutical composition of piperidinoalkanol compounds in solution formUS5576610Jul 5, 1994Nov 19, 1996Motorola, Inc.Method and apparatus for determining battery characteristicsUS5581011May 31, 1995Dec 3, 1996Albany Molecular Research, Inc.Aromatic ketones and processes for their preparationUS5631375Jan 6, 1995May 20, 1997Merrell Pharmaceuticals, Inc.Process for piperidine derivativesUS5738872 *Nov 1, 1996Apr 14, 1998Hoechst Marion Roussel, Inc.Pharmaceutical composition for piperidinoalkanol compoundsUS5750703Feb 2, 1995May 12, 1998Albany Molecular Research, Inc.Piperidine derivatives and process for their productionUS5855912Oct 3, 1997Jan 5, 1999Hoechst Marion Roussel, Inc.Pharmaceutical compositions for piperidinalkanol compoundsUS5932247Oct 9, 1997Aug 3, 1999Hoechst Marion Roussel, Inc.Pharmaceutical composition for piperidinoalkanol compoundsUS6037353Mar 2, 1995Mar 14, 2000Hoechst Marion Roussel, Inc.Method of providing an antihistaminic effect in a hepatically impaired patientUS6039974Jul 31, 1998Mar 21, 2000Hoechst Marion Roussel, Inc.Pharmaceutical composition for combination of piperidinoalkanol-decongestantUS6113942Sep 21, 1998Sep 5, 2000Aventis Pharmaceuticals Inc.Pharmaceutical composition for piperidinoalkanol compoundsUS6147216Jun 2, 1995Nov 14, 2000Merrell Pharmaceuticals Inc.Intermediates useful for the preparation of antihistaminic piperidine derivativesUS6187791Jan 12, 2000Feb 13, 2001Merrell Pharmaceuticals Inc.Method of providing an antihistaminic effect in a hepatically impaired patientUS6242606Jul 14, 1994Jun 5, 2001Merrell Pharmaceuticals Inc.Intermediates useful for the preparation of antihistaminic piperidine derivativesUS6399632 *Sep 15, 2000Jun 4, 2002Merrell Pharmaceuticals Inc.Method of providing an antihistaminic effect in a hepatically impaired patientUS6613906Jun 6, 2000Sep 2, 2003Geneva Pharmaceuticals, Inc.Crystal modificationUS20020177608Apr 8, 2002Nov 28, 2002Ben-Zion DolitzkyPolymorphs of fexofenadine hydrochlorideUS20040077683Jul 31, 2001Apr 22, 2004Reddy M. SatyanarayanaNovel crystalline forms of 4-[4-[4-(hydroxydiphenylmethyl)-1- piperidinyl]-1-hydroxybutyl]-$g(a)-dimethylbenzene acetic acid and its hydrochlorideCA1123438AJan 18, 1980May 11, 1982Joseph E. DolfiniPiperidine derivativesCA1123439AJan 18, 1980May 11, 1982Albert A. CarrPiperidine derivativesCA2117892A1Mar 10, 1993Oct 28, 1993Chi-Hsin R. King4-diphenylmethyl piperidine derivatives and process for their preparationCA2181089A1Jun 21, 1994Dec 25, 1994Thomas E. D'ambraPiperidine Derivatives and Process for Their ProductionWO1993021156A1Mar 10, 1993Oct 28, 1993Merrell Dow Pharmaceuticals Inc.4-diphenylmethyl piperidine derivatives and process for their preparationWO1994003170A1Aug 3, 1993Feb 17, 1994Sepracor Inc.Terfenadine metabolites and their optically pure isomers for treating allergic disordersWO1994009008A1Sep 29, 1993Apr 28, 1994Nycomed Dak A/SProcess for preparing pure podophyllotoxinWO1995000480A1May 26, 1994Jan 5, 1995Merrell Pharmaceuticals Inc.Novel intermediates for the preparation of antihistaminic 4-diphenylmethyl/diphenylmethoxy piperidine derivativesWO1996026726A1Jan 26, 1996Sep 6, 1996Hoechst Marion Roussel, Inc.Pharmaceutical composition for piperidinoalkanol compounds* Cited by examinerNon-Patent CitationsReference1Advisory Action dated Sep. 24, 2003, in U.S. Appl. No. 10/160,883.2Affidavit of Lilach Goldman, dated Jul. 10, 2006.3Akaishi et al. "Synthesis of diamond using nonmetallic catalysts." Chemical Abstracts 116:73144 (1992).4Amon, U. et al.; Anti-allergic effects of H1-receptor antagonists on histamin-containing cells; 178(8) Dematologische Monatsschrift 327-33 (1992).5Apperley, D. C. et al. "Quantitative Nuclear Magnetic Resonance Analysis of Solid Formoterol Fumarate and Its Dihydrate," J. Pharm. Sci. (2003) 92(12):2487-2494.6Argentine Search Report, dated Sep. 9, 1999.7Bailey, D.G. et al.; Effect of Grapefruit Juice and Naringin on Nisoldipine Pharmacokinetics; 54 Clinical Pharmacology & Therapeutics 589-94 (1993).8Bailey, D.G. et al.; Grapefruit Juice and Drugs: How Significant is the Interaction; 26(2) Clinical Pharmacokinetics 91-98 (1994).9Bailey, D.G. et al.; Grapefruit Juice-Felodipine Interaction: Mechanism, Predictability, and Effect of Naringin; 53 Clinical Pharmacology & Therapeutics 637-42 (1993).10Bailey, D.G. et al.; Grapefruit Juice—Felodipine Interaction: Mechanism, Predictability, and Effect of Naringin; 53 Clinical Pharmacology & Therapeutics 637-42 (1993).11Bailey, D.G. et al.; Grapefruit Juice-Felodipine Interaction: Reproducibility and Characterization with the Extended Release Drug Formulation; 40 Br. J. Clinical Pharmacology 135-40 (1995).12Bailey, D.G. et al.; Grapefruit Juice—Felodipine Interaction: Reproducibility and Characterization with the Extended Release Drug Formulation; 40 Br. J. Clinical Pharmacology 135-40 (1995).13Bandyopadhyay, R. et al. "Application of Powder X-Ray Diffraction in Studying the Compaction Behavior of Bulk Pharmaceutical Powders," J. Pharm. Sci. (2005) 94(11):2520-2530.14Baroody, F. et al.: The Effects of H1 antihistamines on the Early Allergic Response; 63 Annals of Allergy 551-55 (1989).15Bennett et al.; Concise Chemical and Technical Dictionary 553 (Chemical Publishing Co. 1974).16Bevington, P. R. "Chapter 10: Goodness of Fit" in Data Reduction and Error Analysis for the Physical Sciences (1969) pp. 187-203.17Brittain, Polymorphism in Pharmaceutical Solids, p. 2, 185 (Marcel Dekker Inc. 1999).18Bugay, D. E. "Characterization of the solid-state: spectroscopic techniques," Advanced Drug Delivery Rev. (2001) 48:43-65.19Burlage, H.M. et al.; Fundamental Principles and Processes of Pharmacy 464-67 (McGraw-Hill 2nd ed. 1949).20Canadian Office Action, with references cited therein, dated Nov. 6, 1998.21Cantilena, L. et al.; Effect of Cimetidine and Ranitidine on the Pharmacokinetics and ECG Pharmacodynamics of Terfenadine; 53(2) Clinical Pharmacology & Therapeutics 161 (1993).22Chan, K.Y. et al.; Direct Enantiomeric Separation of Terfenadine and its Major Acid Metabolite by High-Performance Liquid Chromatography, and the Lack of Stereoselective Terfenadine Enantiomer Biotransformation in Man; 571 J. Chromatography 291-97 (1991).23Chan, K.Y. et at.; Direct Enantiomeric Separation of Terfenadine and Its Major Acid Metabolite by High-Performance Liquid Chromatography, and the Lack of Stereoselective Terfenadine Enantiomer Biotransformation in Man; CA 116:50726(1992).24Charlesworth, E.N. et al.; Cutaneous Late-Phase Response in Food-Allergic Children and Adolescents with Atopic Dermatitis; 23 Clinical and Experimental Allergy 391-98 (1993).25Chen, T.-M. et al.; Determination of the Metabolites of Terfenadine in Human Urine by Thermospray Liquid Chromatography-Mass Spectrometry; 9(10-12) J. Pharmaceutical and Biomedical Analysis 929-33(1991).26Chen, T.-M. et al.; Determination of the Metabolites of Terfenadine in Human Urine by Thermospray Liquid Chromatography—Mass Spectrometry; 9(10-12) J. Pharmaceutical and Biomedical Analysis 929-33(1991).27Cheronis, N. D. Semimicro Experimental Organic Chemistry, A Laboratory Manual 4, 8 (J de Graft 1958).28Cheronis, N.D.; Semimicro Experimental Organic Chemistry, A Laboratory Manual 31-42 (J de Graft 1958).29Cheronis, ND.; Semimicro Experimental Organic Chemistry. A Laboratory Manual 16-17 (J de Graff 1958).30Copending claims as of Oct. 26, 2006, for related U.S. Appl. No. 11/553,751.31Copending claims as of Oct. 30, 2007, for related U.S. Appl. No. 11/534,828.32Copending claims as of Oct. 30, 2007, for related U.S. Appl. No. 11/978,669.33Copending claims as of Oct. 30, 2007, for related U.S. Appl. No. 11/978,670.34 *copies in parent case.35Coutant, J.E. et al.; Determination of Terfenadine and Terfenadine Acid Metabolite in Plasma Using Solid-Phase Extraction and High-Performance Liquid Chromatography with Flourescence Detection; 570 J. Chromatography 136-48 (1991).36Crumb, W.J. et al.; Blockade of Multiple Human Cardiac Potassium Currents by the Antihistamine Terfenadine: Possible Mechanism for Terfenadine-Associated Cardiotoxicity; 47 Molecular Pharmacology 181-90(1995).37David, W. I. F. "Powder Diffraction: Least-Squares and Beyond," J. Research of the National Inst. of Standards and Tech. (2004) 109(1):107-123.38Dean, J.A., Analytical Chemistry Handbook, 10.2-10.26 (McGraw-hill inc. 1955).39Declaration of Dr. Alan P. Kozikowsky, signed Jul. 7, 2006, and submitted in Israel litigation docket No. C.F. 1088/06, with exhibits A-M.40Declaration of Dr. Arthur H. Kibbe, signed Sep. 18, 2006, submitted in Israeli litigation docket No. C.F. 1088/06.41Declaration of Dr. David E. Bugay (5th Declaration) submitted in Israeli litigation docket No. C.F. 1088/06 on Aug. 15, 2007, with Exhibits.42Declaration of Dr. Marcus F. Brackeen, signed Jul. 7, 2006, and submitted in Israeli litigation docket No. C.F. 1088/0, with exhibits A-F.43Declaration of Dr. Mark D. Hollingsworth, signed Jul. 6, 2006, and submitted in Israeli litigation docket No. C.F. 1088/06, with exhibits A-E.44Declaration of Dr. Patrick Stahly, signed on Sep. 19, 2006, and submitted in Israeli litigation docket No. c.F. 1088/06.45Declaration of Dr. Shmuel Cohen, signed on Sep. 20, 2006, and submitted in Israeli litigation docket No. C.F. 1088/06.46Declaration of Dr. Simon Bates (2nd Declaration), submitted in Israeli litigation docket No. C.F. 1088/06 on Aug. 15, 2007, with Figures.47Declaration of Dr. William E. Mayo, signed Aug. 25, 2006, and submitted is Israeli litigation docket No. C.F. 1088/06.48Declaration of Dr. William E. Mayo, signed Jul. 7, 2006, and submitted in Israel litigation docket No. C.F. 1088/0, with exhibits A-M.49Declaration of Mr. Thomas L. Irving, signed Sep. 19, 2006, and submitted in Israeli litigation docket No. C.F. 1088/06.50Declaration of Prof. Abraham Rubinstein, signed Jul. 7, 2006, and submitted in Israel litigation docket No. c.F. 1088/06, with exhibits A-C, including English-language Translation of Appendix B.51Declaration of Prof. Ann E. McDermott, signed Sep. 20, 2006, and submitted in Israeli litigation docket No. C.F. 1088/06, with Exhibits.52Declaration of Prof. Anthony Michael Glazer, signed Aug. 5, 2007, and submitted in Israeli litigation docket No. C.F. 1088/06.53Declaration of Prof. Anthony Michael Glazer, signed Jul. 7, 2006, and submitted in Israeli litigation docket No. C.F. 1088/0, with exhibits A-F.54Declaration of Prof. Anthony Michael Glazer, signed Sep. 20, 2006, and submitted in Israeli litigation docket No. C.F. 1088/06.55Declaration of Prof. Clare Grey, signed Jul. 7, 2006, and submitted in Israeli litigation docket No. C.F. 1088/06, with exhibits A-F.56Declaration of Prof. Jerry L. Atwood, signed on Aug. 8, 2007, and submitted in Israeli litigation docket No. C.F. 1088/06, with Exhibits.57Declaration of Prof. Joel Bernstein (5th Delcaration), submitted in Israeli litigation docket No. C.F. 1088/06 on Aug. 15, 2007, with Figures.58Declaration of Prof. Peter W. Stephens, signed Jul. 7, 2006, and submitted in Israel litigation docket No. C.F. 1088/06.59Declaration of Prof. Peter W. Stephens, signed on Aug. 3, 2007, and submitted in Israeli litigation docket No. C.F. 1088/06, with Figures and Exhibits.60Declaration of Prof. Peter W. Stephens, signed on Sep. 19, 2006, and submitted in Israeli litigation docket No. C.F. 1088/06, with Figures and Exhibits.61Derome, A. E. Modem NMR Techniques for Chemistry Research (1987) pp. 22-26.62Distinction between Crystalline and Amorphous Solids, Encyclopedia Britannica Online (2004).63 *Doelker et al. "Crystalline modification . . . " CA 138:209993 (2002).64Doelker et al. "Crystalline modification and polymorphism changes during drug manufacturing." 63-Pharmaceuticals. Chemical Abstracts 138:209993 (2003).65Doelker et al. "Physicochemical behavior of active substances, Consequences for the feasibility and stability of pharmaceutical forms." 63-Pharmaceuticals. Chemical Abstracts 132:325872 (2000).66 *Doelker et al. "Physicochemical behavior or active . . . "CA 132:325872 (2000).67Eagleson "Concise encyclopedia chemistry" (1944) p. 872-873.68English-language Translation of Affidavit of Lilach Goldman, dated Jul. 10, 2006.69English-language translation of Supreme Court Reply Brief by the Commissioner of the Korean Intellectual Property Office in Korean Case No. 2009 Hu 2012 Final Rejection (Patent), filed with the Korean Supreme Court on Aug. 13, 2009, and received on Aug. 24, 2009.70English-language translation of Supreme Court Supplemental Brief by Aventis Pharmaceuticals, Inc. in Korean Case No. 2009 Hu 2012 Final Rejection (Patent), filed with the Supreme Court on Oct. 6, 2009.71European Search Report, dated Dec. 20, 2001.72Evans et al.; An Introduction to Crystal Chemistry 296-98, 396 (Cambridge 2nd Edition 1964).73Foks et al. "Effect of temperature and supersaturation on the crystallization of polyethylene adipate from dioxane solutions," SciSearch 02857044 (1993).74Freeman, R. A Handbook of Nuclear Magnetic Resonance (1988) pp. 101-223.75Garteiz, D.A. et al.; Pharmacokinetics and Biotransformation Studies of Terfenadine in Man; 32 Drug Research 1185-90 (1982).76Gavetter, F. J. et al. "Chapter 19: The Chi Square Statistic: Tests for Goodness of Fit and Independence" in Statistics for the Behavioral Sciences: A First Course for Students of Psychology and Education (1985) pp. 638-675.77 *Gibson et al. "Modulation of antagonisti binding . . . " Br. J. Pharmcol. v. 111 (Apr.) p. 1262-1268 (1994).78 *Glusker et al. "Crystal structure analysis a primer" p. 12 (1985).79Gramberg, L.G. et al.; Pilot Study on the Determination of Terfenadine in Human Plasma by GC/MS; A87431 Rapp Tno Hoofdgroep Voeding Voedingsmiddelen Tno 2-12 (1987).80Griffiths, P. R. et al. "Introduction to spectral deconvolution," Trends in analytical chemistry (1986) 5(8):209-215.81Guidance for Industry: Q2B Validation of Analytical Procedures: Methodology, U.S. Department of Health and Human Services, FDA (1996).82Gupta, S.K. et al.; High-Performance Liquid Chromatographic Determination of Terfenadine in Commercial Tablets; 361 J. Chromatography 403-06 (1986).83Harris, R. K. "Applications of solid-state NMR to pharmaceutical polymorphism and related matters," J. of Pharmacy and Pharmacology (2007) 59:225-239.84Henton, D. et al; Process for Preparing Anhydrous and Hydrate of Antihistaminic Piperidine Derivatives (Polymorphs and Pseudomorphs); CA 124:202030 (1996).85Hohlweg et al. "The chemistry and biology of the pure corpus luteum hormone ‘progesterone,’" Chem. Abstracts 30:50875 (1936).86Hohlweg et al. "The chemistry and biology of the pure corpus luteum hormone 'progesterone,'" Chem. Abstracts 30:50875 (1936).87Honig, P.K. et al.; Changes in the Pharmacokinetics and Electrocardiographic Pharmacodynamics of Terfenadine with Concomitant Administration of Erythromycin; 52(3) Clinical Pharmacology & Therapeutics 231-38 (1992).88Honig, P.K. et al.; Comparison of the Effect of the Macrolide Antibiotics Erythromycin, Clarithromycin and Azithromycin on Terfenadine Steady-State Pharmacokinetics and Electrocardiographic Parameters; 7(3) Drug Invest. 148-56 (1994).89Honig, P.K. et al.; Effect of Concomitant Administration of Cimetidine and Ranitidine on the Pharmacokinetics and Electrocardiographic Effects of Terfenadine; 45(1) Eur. J. Clinical Pharmacology 41-46 (1993).90Honig, P.K. et al.; Itraconazole Affects Single-Dose Terfenadine Pharmacokinetics and Cardiac Repolarization Pharmacodynamics; 33(12) J. Clinical Pharmacology 1201-06 (1993).91Honig, P.K. et al.; Population Variability in the Pharmacokinetics of Terfenadine: The Case for a Pseudo- Polymorphism with Clinical Implications; 11(2) Drug Metabolism and Drug Interactions 161-68 (1994).92Honig, P.K. et al.; Terfenadine-Ketoconazole Interaction: Pharmacokinetic and Electrocardiographic Consequences; 269(12) J. Am. Med. Assoc. 1513-18 (1993).93Honig, P.K. et al.; The Effect of Fluconazole on the Steady-State Pharmacokinetics and Electrocardiographic Pharmacodynamics of Terfenadine in Humans; 53(6) Clinical Pharmacology & Therapeutics 630-36 (1993).94Humphreys, F. & Shuster, S.; The Effect of Nedocromil on Weal Reactions in Human Skin; 24 Br. J. Clinical Pharmacology 405-08 (1987).95Internet page printouts of Hawley's Condensed Chemical Dictionary 1 (14th ed. 2002) (definitions of amorphous and conformation).96 *Jain et al. "Polymorphisom in pharmacey" Indian Drugs 23(g)315-329 (1986).97Jain et al., "Polymorphism in Pharmacy" Indian Drugs 23(g)315-329 (1986).98Jalonen et al., "The crystal growth of carbamazepine from solvents with different relative permittivity," Derwent Acc. No. 90-02014 (1989).99Jenkins, R. et al. Introduction to X-ray Powder Diffractometry (1996) p. 266.100Jurima-Romet, M. et al.; Induction of CYP3A and Associated Terfenadine N-Dealkylation in Rat Hepatocytes Cocultured with 3T3 Cells; 11 Cell Biology and Toxicology 313-27 (1995).101Jurima-Romet, M. et al.; Terfenadine Metabolism in Human Liver: In Vitro Inhibition by Macrolide Antibiotics and Azole Antifungals; 22(6) Drug Metabolism and Disposition 849-57(1994).102Kameda T. "Molecular structure of crude beeswax studied by solid-state 13C NMR," J. Insect Sci. (2004) 4(29):1-5.103Kao, H. et al. "Activation Conditions Play a Key Role in the Activity of Zeolite CaY: NMR and Product Studies of Brønsted Acidity," J. Phys. Chem. A (1998) 102:5627-5638.104Kawai S. H. et al. "A Facile Synthesis of an Oxidation Product of Terfenadine," J. Organic Chemistry (1994) 59(10):2620-22.105Kawai, S.H. et al.; A Facile Synthesis of an Oxidation Product of Terfenadine; 59(10) J. Organic Chemistry 2621-22 (1994).106Kietzmann, H. et al.; Comparison of Cetirizine and Terfenadine in the Treatment of Chronic Idiopathic Urticaria; 65 Annals of Allergy 498-500 (1990).107King et al. "4-diphenylmethyl-piperidine derivatives and process for their preparation," Chem. Abstracts 120:217287 (1994).108King et al. "Preparation of 4-(omega-piperidinoalkanoyl)phenylacetates and analogs as drugs," Chem. Abstracts 127:50544 (1997).109King et al. "Preparation of 4—(ω-piperidinoalkanoyl)phenylacetates and analogs as drugs," Chem. Abstracts 127:50544 (1997).110Krause, L. B. and Shuster, S. "The Effect of Terfenadine on Dermographic Wealing," Br. J. Dermatology (1984) 110:73-79.111Krause, L.B. & Shuster, S.; The Effect of Terfenadine on Dermographic Wealing; 110 Br. J. Dermatology 73-79 (1984).112Langford, J. I. et al. "Powder diffraction," Rep. Prog. Phys. (1996) 59:131-234.113Le Bail, A. "ESPOIR: A Program for Solving Structures by Monte Carlo from Powder Diffraction Data," 7th European Powder Diffraction Conference (2000), Barcelona, May 20-23.114Le Bail, A. et al. "A crystal structure for the souzalite/gormanite series from synchrotron powder diffraction data," Eur. J. Mineral. (2003) 15:719-723.115Lee, Y. J. et al. "6Li and 7Li Magic-Angle Spinning Nuclear Magnetic Resonance and In Situ X-Ray Diffraction Studies of the Charging and Discharging of LixMn2O2at 4 V," J. Electrochem. Soc. (2000) 147(3):803-812.116Lipicky. R.J.; A Viewpoint on Drugs that Prolong the QT Interval; 72 Am. J. Cardiology 53B-59B (1993).117Mascaselli L. "The isomerisim of erucic, brassidinic and isoerucic acids. V. Results with the eryohydric and eutectic methods," Chem. Abstracts 112:2214(1918).118Massey, W.A. & Lichtenstein, L.M.; The Effects of Antihistamines Beyond H1 Antagonism in Allergic Inflammation; 86 J. Allergy and Clinical Immunology 1019-24 (1990).119Massey, W.A. et al.; Cutaneous IgE-Mediated Inflammatory Lesion Size is Inhibited by an H Antagonist (Terfenadine) while Mediator Release is Unaffected In Vivo and In Vitro; 23 Clinical and Experimental Allergy 399-405 (1993).120Mathews, D.R. at al.; Torsades de Pointes Occurring in Association with Terfenadine Use (Letter and Reply); 266(17) J. Am. Med. Assoc. 2375-76(1991).121Maurer, H. & Pfleger K.; Identification and Differentiation of Alkylamine Antihistamines and their Metabolites in Urine by Computerized Gas Chromatography-Mass Spectrometry; 430(1) J. Chromatography 31-41 (1988).122McCauley, J.A. at al.; The Effect of Polymorphism and Metastability on the Characterization and Isolation of Two Pharmaceutical Compounds; 26 .). Phys. D.: Appl. Phys. 85-89 (1993).123Monahan, B.P. et al.; Torsades de Pointes Occurring in Association with Terfenadine Use; 264(21) J. Am. Med. Assoc. 2788-90 (1990).124Morrison, R.T. & Boyd, R.N.; Organic Chemistry 75 (1973).125 *Muzaffar et al. "Polymorphism and drug availability" J. Phar. 1(1) 59-66 (1979).126Muzaffar et al. "Polymorphism and drug availability" J. Phar. 1(1)59-66 (1979).127Naclerio, R.M. at al.; Terfenadine, an H1 Antihistamine, Inhibits Histamine Release In Vivo in the Human; 142(1) Am. Rev. Respir. Dis. 167-171 (1990).128Niggli "New mineral syntheses" CA 16:21134 (1922).129Norwegian Search Report, dated Nov. 21, 2001.130Offerdahl, T. J. "Solid-State Nuclear Magnetic Resonance Spectroscopy for Analyzing Polymorphic Drug Forms and Formulations," Pharmaceutical Technology (2006).131Offerdahl, T. J. et al. "Quantitation of Crystalline and Amorphous Forms of Anhydrous Neotame using 13C CPMAS NMR Spectroscopy," J. Pharm. Sci. (2005) 94(12):2591-2605.132Office Action dated Apr. 18, 2003, in Application No. 10/125,094.133Office Action dated Apr. 3, 2007, in copending U.S. Appl. No. 11/534,828.134Office Action dated Aug. 8, 2003, in Application No. 10/214,262.135Office Action dated Feb. 18, 2004, in U.S. Appl. No. 10/386,812.136Office Action dated Jun. 11, 2004 in U.S. Appl. No. 10/160,883.137Office Action dated Mar. 10, 2003, in Application No. 10/160,883.138Office Action dated Mar. 23, 2005, in U.S. Appl. No. 10/160,883.139Office Action dated May 17, 2004, in Application No. 10/125,094.140Office Action dated May 4, 2004, in U.S. Appl. No. 10/214,262.141Office Action dated Oct. 22, 2004, Application No. 10/386,812.142Office Action dated Sep. 18, 2007, in copending U.S. Appl. No. 11/534,828.143Okerholm, R.A. et al.; Bloavailability of Terfenadine in Man; 2 Biopharmaceutics & Drug Disposition 185-90 (1981).144Opponent's Statement of Case filed in Israeli Opposition proceeding IL 113747. (2006).145Opponent's Statement of Case filed in Israeli Opposition proceeding IL 134917. (2007).146 *Otsuka et al. "Effect of polymorphic . . . " Chem. Pharm. bull 47(6)852-856 (1999).147Otsuka et al. "Effect of Polymorphic Forms of Bulk Powders on Pharmaceutical Properties of Carbamazepine Granules." Chem. Pharm. Bull. 47(6)852-856 (1999).148PCT International Search Report, dated Aug. 10, 1995.149Physical Properties of Liquids, Encyclopedia Britannica Online (2004).150Prince, E. "Mathematical aspects of Rietveld refinement" pp. 43-101, (1993).151Prosecution File History for U.S. Application No. 10/162,011 (now U.S. Patent No. 7,138,524).152Ramachers, U. et al.; Direct Effects of Second-Generation H1-Receptor Antagonists on the Activation of Human Basophils; 41 Agent Actions Special Conference Issue C45-46 (1994).153Rampe, D. et al.; Effects of Terfenadine and Its Metabolites on a Delayed Rectifier K Channel Cloned from Human Heart; 44(6) Molecular Pharmacology 1240-45 (1993).154Rao, N. et al.; Pharmacokinetics of Terfenadine-Acid-Metabolite, MDL 16,455, in Healthy Geriatric Subjects (Abstract); 12 Pharm. Research S-386 (1995).155Rau, S.E. et al; Inhibition of Terfenadine Metabolism by Coadministration of Grapefruit Juice in Humans (Abstract); Clin. Invest. Med. B16 (1995).156Rawlins, E.A.; Bentley's Textbook of Pharmaceuticals 211-12 (8th ed. 1977).157Roberts, R. M. et al. An Introduction to Modem Experimental Organic Chemistry, Holt, Rinehart and Winston, Inc., 1969, pp. 48-51.158Rouhi et al. "The Right Stuff," Chemical and Engineering News (Feb. 24, 2003) 32-35.159 *Rowland and Tozer "Clinical pharmacokinetics concepts and application" p. 123 (1995).160Rowland et al. Clinical Pharmacokinetics: Concepts and Applications. Williams and Wilkins, p. 123 (1995).161Russell, T. et al.; A Comparison of MDL 16,455A Pharmacokinetics by Gender (Abstract); 12 Pharm. Research S-389 (1995).162Sable et al. "Effect of solvent deposition on spironolactone," Derwent Acc. No. 86-22527 (1985).163Schulze, D. G. "Correction of Mismatches in 2θ Scales During Differential X-ray Diffraction," Clays and Clay Minerals (1986) 34(6):681-685.164Shuster, S.; Antihistamines in the Treatment of Urticarial Disorders; 42(4A) Cutis 26-28 (1988).165Shuster, S.; Comparative Trial of Two Non-Sedative H1 , Antihistamines, Terfenadine and Astemizole, for Hay Fever; 41 Thorax 654-56 (1986).166Stephenson, G. A. et al. "Characterization of the solid state: quantitative issues." Advanced Drug Delivery Rev. (2001) 48:67-90.167Submission of Documents dated Sep. 6, 2008 in U.S. Appl. No. 10/162,011 and Exhibits.168Surapaneni, S. & Khalil, S.K.W.; A Preliminary Pharmacokinetic Study of the Enantiomers of the Terfenadine Acid Metabolite in Humans; 6 Chirality 479-483(1994).169Surapaneni, S. & Khalil, S.K.W.; A Sensitive HPLC Method for the Determination of Terfenadine and its Metabolite in Human Plasma; 17(11) J. Liquid Chromatography 2419-28 (1994).170Tauson et al. "Polymorphism of crystals and phase dimensional effect: graphite-diamond transformation" Chem. Abstracts 104:171677(1986).171Terao et al. "Second order nonlinear optical properties and polymorphism of benzophenone derivatives," Pascal No. 92-0591460 (1990).172Terhechte, A. & Blascke, G.; Indirect and Direct Racemate Separation of Terfenadine and its Main Metabolite MDL 16,455A (Translation); 324 Arch. Pharm. 710 (1991).173Terhechte, A. & Blascke, G.; Investigation of the Stereoselective Metabolism of the Chiral H-11-Antihistaminic Drug Terfenadine by High-Performance Liquid Chromatography; 694 J. Chromatography A 21 9-25 (1995).174Terhechte, A. & Blascke, G.; Studies of the Enantiomers of the Metabolite Terfenadine: Designation of the Main Metabolite Derived from Serum and Urine through HPLC and Solid Phase Extraction; Intemationales Chiralitatssymposium (1992).175Third Party Observation submitted in European Patent Application No. 01124314.4 on Aug. 14, 2006.176Tishmack, P. A. et al. "Solid-State Nuclear Magnetic Resonance Spectroscopy-Pharmaceutical Applications," J. Phann Sci. (2003) 92(3):441-474.177Togias, A.G. et al; In Vivo and In Vitro Effects of Antihistamines on Mast Cell Mediator Release: a Potentially Important Property in the Treatment of Allergic Disease; 63 Annals of Allergy 465-69(1989).178Ulicky, L. et al.; Comprehensive Dictionary of Physical Chemistry 21 (Prentice Hall 1992).179Urazovskii "Molecular polymorphism" CA 45:51916(1951).180US Pharmacopia #23 National Formulary #18, p. 1843-1844 (1995).181van Bavel, J. et al.; Intranasal Fluticasone Proprionate is More Effective than Terfenadine Tablets for Seasonal Allergic Rhinitis; 154 Arch. Internal Medicine 2699-2704 (1994).182Wagenmann, M. et al.; The Effect of Terfenadine on Unilateral Nasal Challenge with Allergen; 93(3) J. Allergy and Clinical Immunology 594-605 (1994).183Woodward, J.K. & Munro, N. L.; Terfenadine, the First Non-Sedating Antihistamine; 32 Drug Research 1154-56 (1982).184Yang, T. et al.; Block of a Human Cardiac K Channel by Terfenadine and its Enantiomers, but not by Terfenadine Carboxylate (Abstract); 17 Pacing Clinical Electrophysiology 777 (1994).185Yang, T. et al; Mechanism of Block of A Human Cardiac Potassium Channel by Terfenadine Racemate and Enantiomers; 115 Br. J. Pharmacology 267-74 (1995).186Young, R. A. (Ed.) "Chapter 1: Introduction to the Rietveld Method," The Rietveld Method, Oxford Univ. Press, 1993, pp. 1-42.187Yu, L. et al. "Thermochemistry and Conformational Polymorphism of a Hexamorphic Crystal System," J. Am. Chem. Soc. (2000) 122:585-591.188Yun, C. et al.; Oxidation of the Antihistaminic Drug Terfenadine in the Human Liver Microsomes; 21(3) Drug Metabolism and Disposition 403-09 (1993).189Zamani, K. et al.; Enantiomeric Analysis of Tertenadine in Rat Plasma by H PLC; 3 Chirality 467-70(1991).* Cited by examinerReferenced byCiting PatentFiling datePublication dateApplicantTitleUS20080167471 *Oct 30, 2007Jul 10, 2008Aventis Pharmaceuticals Inc.Processes for preparing anhydrous and hydrate forms of antihistaminic piperidine derivatives, polymorphs and pseudomorphs thereof* Cited by examinerClassifications U.S. Classification514/317International ClassificationA61P37/08, A61K31/451, C07D, A61P11/08, A61K, C07D211/82, A61P43/00, C07D211/32, A61K31/44, C07D211/22, A61K31/445Cooperative ClassificationC07D211/22, A61K31/445European ClassificationC07D211/22, A61K31/445Legal EventsDateCodeEventDescriptionOct 29, 2009ASAssignmentOwner name: AVENTIS PHARMACEUTICALS INC., NEW JERSEYFree format text: ASSIGNMENT OF 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