I 1111111111111111 11111 1111111111 11111 1111111111 1111111111 111111111111111111
`US0099015 85B2
`
`c12) United States Patent
`Lulla et al.
`
`(IO) Patent No.:
`(45) Date of Patent:
`
`US 9,901,585 B2
`*Feb.27,2018
`
`(54)
`
`COMBINATION OF AZELASTINE AND
`FLUTICASONE FOR NASAL
`ADMINISTRATION
`
`(71)
`
`Applicant: Cipla Limited, Mumbai (IN)
`
`(72)
`
`Inventors: Amar Lulla, Mumbai (IN); Geena
`Malhotra, Mumbai (IN)
`
`(73)
`
`Assignee: Cipla Limited, Mumbai (IN)
`
`( *)
`
`Notice:
`
`Subject to any disclaimer, the term ofthis
`patent is extended or adjusted under 35
`U.S.C. 154(b) by O days.
`
`This patent is subject to a terminal dis-
`claimer.
`
`(21)
`
`Appl. No.: 15/070,839
`
`(22)
`
`Filed:
`
`Mar. 15, 2016
`
`(65)
`
`Prior Publication Data
`
`US 2017/0035780 Al
`
`Feb. 9, 2017
`
`Related U.S. Application Data
`
`(60) Continuation of application No. 14/661,700, filed on
`Mar. 18, 2015, now abandoned, which
`is a
`continuation of application No. 14/539,646, filed on
`Nov. 12, 2014, now abandoned, which
`is a
`continuation of application No. 13/644,127, filed on
`Oct. 3, 2012, now Pat. No. 8,937,057, which is a
`continuation of application No. 12/508,388, filed on
`Jul. 23, 2009, now Pat. No. 8,318,709, which is a
`division of application No. 10/518,016, filed as
`application No. PCT/GB03/02557 on Jun. 13, 2003,
`now Pat. No. 8,168,620.
`
`(30)
`
`Foreign Application Priority Data
`
`Jun. 14, 2002
`
`(GB) ................................... 0213739.6
`
`(51)
`
`(2006.01)
`(2006.01)
`(2006.01)
`(2017.01)
`(2017.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`
`Int. Cl.
`A61K 31156
`A61K 9/10
`A61K 47126
`A61K 47118
`A61K 47110
`A61K 47138
`A61K 9/00
`A61K 31155
`A61K 31158
`A61K 311573
`(52) U.S. Cl.
`CPC ............ A61K 31156 (2013.01); A61K 9/0043
`(2013.01); A61K 9/10 (2013.01); A61K 31155
`(2013.01); A61K 311573 (2013.01); A61K
`31158 (2013.01); A61K 47110 (2013.01); A61K
`471183 (2013.01); A61K 471186 (2013.01);
`A61K 47126 (2013.01); A61K 47138 (2013.01)
`( 58) Field of Classification Search
`None
`See application file for complete search history.
`
`(56)
`
`References Cited
`
`U.S. PATENT DOCUMENTS
`
`2,837,464 A
`3,067,197 A
`3,312,590 A
`3,506,694 A
`3,557,162 A
`3,639,434 A
`3,755,302 A
`3,813,384 A
`3,828,080 A
`3,856,828 A
`3,891,631 A
`3,981,894 A
`3,989,686 A
`4,093,721 A
`4,113,680 A
`4,187,301 A
`4,188,385 A
`4,198,403 A
`4,221,787 A
`4,261,984 A
`4,263,289 A
`4,267,173 A
`4,285,937 A
`4,310,466 A
`
`6/1958 Nobile
`l 2/ 1962 Agnello et al.
`4/ 1967 Elks et al.
`4/1970 Oxley
`1/1971 Lens et al.
`2/1972 Oxley et al.
`8/1973 Ercoli et al.
`5/1974 Vogelsang et al.
`8/1974 Phillipps et al.
`12/1974 Phillipps et al.
`6/ 197 5 Phillipps et al.
`9/1976 Phillipps et al.
`11/1976 Phillips et al.
`6/ 1978 Phillipps et al.
`9/1978 Kamano et al.
`2/1980 Edwards
`2/1980 Edwards
`4/1980 Alvarez
`9/1980 Bodor et al.
`4/1981 Alvarez
`4/1981 Edwards
`5/1981 Draper
`8/1981 Kalvoda
`1/1982 Edwards
`(Continued)
`
`FOREIGN PATENT DOCUMENTS
`
`AU
`BE
`
`12/2003
`2003244799 B2
`889563 Al
`11/1981
`(Continued)
`
`OTHER PUBLICATIONS
`
`ABPI Compendium of Data Sheets and Summaries of Product
`Characteristics, 1999-2000, cover page, p. 43 and index p. 1882,
`Datapharm Publications Limited, London.
`ABPI Data Sheet Compendium, 1995-96, cover page plus pp.
`38-39, Datapharm Publications Limited, London.
`Aigbirhio, Franklin I., et al., "Automated radiosynthesis of no(cid:173)
`carrier-added [S-fluoromethyl-18F]Fluticasone propionate as a
`radiotracer for lung deposition studies with PET," Journal of
`Labelled Compounds and Radiopharmaceuticals, vol. 39, No. 7,
`1997, pp. 569-584, John Wiley & Sons, Ltd.
`Akerlund, Anders, et al., "Clinical trial design, nasal allergen
`challenge models, and considerations of relevance to pediatrics,
`nasal polyposis, and different classes of medication," J. Allergy Clin
`Immunol, Mar. 2005, vol. ll5, No. 3, pp. S460-S482.
`(Continued)
`
`Primary Examiner - Robert A Wax
`Assistant Examiner - Thor Nielsen
`(74) Attorney, Agent, or Firm - Conley Rose, P.C.;
`Rodney B. Carroll
`
`ABSTRACT
`(57)
`A pharmaceutical product or formulation, which comprises
`azelastine or a pharmaceutically acceptable salt, solvate or
`physiologically functional derivative thereof, and a steroid,
`or a pharmaceutical acceptable salt, solvate or physiologi(cid:173)
`cally functional derivative thereof, preferably the product or
`formulation being in a form suitable for nasal or ocular
`administration.
`
`30 Claims, No Drawings
`
`

`

`(56)
`
`References Cited
`
`U.S. PATENT DOCUMENTS
`
`4,335,121 A
`4,377,575 A
`4,472,393 A
`4,607,028 A
`4,710,495 A
`4,782,047 A
`4,861,765 A
`4,992,474 A
`4,994,439 A
`4,996,335 A
`5,063,222 A
`5,081,113 A
`5,086,050 A
`5,164,194 A
`5,202,316 A
`5,232,919 A
`5,271,946 A
`5,362,721 A
`5,420,120 A
`5,536,444 A
`5,608,093 A
`5,658,549 A
`5,658,919 A
`5,707,984 A
`5,716,966 A
`5,830,490 A
`5,837,699 A
`5,849,265 A
`5,854,269 A
`5,889,015 A
`5,897,858 A
`5,914,122 A
`5,972,327 A
`5,972,920 A
`5,976,573 A
`5,981,517 A
`5,993,781 A
`6,017,963 A *
`
`6/1982 Phillipps et al.
`3/1983 Stache et al.
`9/1984 Shapiro
`8/1986 Schmidlin
`12/1987 Bodor
`11/1988 Benjamin et al.
`8/1989 Mitsukuchi et al.
`2/1991 Skidmore et al.
`2/1991 Longenecker et al.
`2/1991 Bodor
`11/1991 Komoto et al.
`1/1992 Claussner et al.
`2/1992 Hettche et al.
`11/1992 Hettche
`4/1993 Claussner et al.
`8/1993 Scheffler et al.
`12/1993 Hettche
`11/1994 Stache et al.
`5/1995 Boltralik
`7/1996 Hettche et al.
`3/1997 Stache et al.
`8/1997 Akehurst et al.
`8/1997 Ratnaraj et al.
`1/1998 Tjoeng et al.
`2/1998 Cupps et al.
`11/1998 Weinstein et al.
`11/1998 Sequeira et al.
`12/1998 Li-Bovet et al.
`12/1998 Haslwanter et al.
`3/1999 Sequeira et al.
`4/1999 Haslwanter et al.
`6/1999 Otterbeck et al.
`10/1999 Lin et al.
`10/1999 Seidel
`11/1999 Kim
`11/1999 Bodor
`11/1999 Snell et al.
`1/2000 Alfonso
`
`6,057,307 A
`6,127,353 A
`6,136,294 A
`6,143,329 A
`6,197,761 Bl
`6,241,969 Bl
`6,253,762 Bl
`6,261,539 Bl
`6,294,153 Bl*
`
`5/2000 Sequeira et al.
`10/2000 Yuen et al.
`10/2000 Adjei et al.
`11/2000 Kim
`3/2001 Biggadike et al.
`6/2001 Saidi et al.
`7/2001 Britto
`7/2001 Adjei et al.
`9/2001 Modi
`
`11/2001 Haslwanter et al.
`11/2001 Dobrozsi
`12/2001 Herve et al.
`4/2002 Doi
`5/2002 Malmqvist-Granlund
`A61K 9/0043
`424/434
`
`6,316,483 Bl
`6,319,513 Bl
`6,330,938 Bl
`6,368,616 Bl
`6,391,340 Bl*
`
`6,395,300 Bl
`6,416,743 Bl
`6,436,924 B2
`6,537,983 Bl
`6,565,832 Bl
`6,583,180 B2
`6,750,210 B2
`6,759,398 B2
`6,777,399 B2
`6,777,400 B2
`6,787,532 B2
`6,835,724 B2
`6,858,593 B2
`6,858,596 B2
`6,878,698 B2
`6,881,423 B2
`6,921,757 B2
`7,101,866 B2
`7,125,985 B2
`
`5/2002 Straub et al.
`7/2002 Fass berg et al.
`8/2002 Poppe et al.
`3/2003 Biggadike et al.
`5/2003 Haslwanter et al.
`6/2003 Link et al.
`6/2004 Biggadike
`7/2004 Biggadike
`8/2004 Biggadike et al.
`8/2004 Biggadike et al.
`9/2004 Biggadike et al.
`12/2004 Stache et al.
`2/2005 Biggadike et al.
`2/2005 Biggadike et al.
`4/2005 Biggadike et al.
`4/2005 Dohi et al.
`7/2005 Cuenoud et al.
`9/2006 Biggadike et al.
`10/2006 Biggadike et al.
`
`US 9,901,585 B2
`Page 2
`
`7,132,532 B2
`7,144,845 B2
`7,214,672 B2
`7,244,742 B2
`7,288,536 B2
`7,291,608 B2
`7,291,609 B2
`7,405,206 B2
`7,498,321 B2
`7,524,970 B2
`7,531,528 B2
`7,541,350 B2
`7,579,335 B2
`7,592,329 B2
`7,629,335 B2
`7,638,508 B2
`7,776,315 B2
`8,071,073 B2
`8,163,723 B2
`8,168,620 B2
`8,304,405 B2
`8,318,709 B2
`8,933,060 B2
`8,937,057 B2
`9,259,428 B2
`2001/0025040 Al
`2002/0037297 Al
`2002/0061281 Al
`2002/0076382 Al
`2002/0081266 Al
`2002/0132803 Al
`2003/0018019 Al
`2004/0136918 Al
`2004/0204399 Al
`2004/0235807 Al
`2004/0242638 Al
`2005/0163724 Al
`2005/0192261 Al
`2006/0002861 Al
`2006/0228306 Al
`2007 /0020330 Al
`2009/0124585 Al
`2009/0156567 Al
`2009/0286762 Al
`2010/0152147 Al
`2010/0311706 Al
`2012/0065177 Al
`2015/0072010 Al
`
`11/2006 Biggadike et al.
`12/2006 Biggadike et al.
`5/2007 Komoto et al.
`7/2007 Pieper et al.
`10/2007 Biggadike et al.
`11/2007 Biggadike et al.
`11/2007 Biggadike et al.
`7/2008 Biggadike et al.
`3/2009 Biggadike et al.
`4/2009 John
`5/2009 Biggadike et al.
`6/2009 Biggadike et al.
`8/2009 Biggadike et al.
`9/2009 Biggadike et al.
`12/2009 Biggadike et al.
`12/2009 Biggadike et al.
`8/2010 Pair et et al.
`12/2011 Dang et al.
`4/2012 Lulla et al.
`5/2012 Lulla et al.
`11/2012 Lulla et al.
`11/2012 Lulla et al.
`1/2015 Lulla et al.
`1/2015 Lulla et al.
`2/2016 Lulla et al.
`9/2001 Poppe et al.
`3/2002 Crespo et al.
`5/2002 Osbakken et al.
`6/2002 Kaplan et al.
`6/2002 Woolfe et al.
`9/2002 Dedhiya et al.
`1/2003 Meade et al.
`7/2004 Garrett et al.
`10/2004 Osbakken et al.
`11/2004 Weinrich et al.
`12/2004 Yanni et al.
`7/2005 Miyadai et al.
`9/2005 Jost-Price et al.
`1/2006 Biggadike
`10/2006 Lane
`1/2007 Dang et al.
`5/2009 Cross et al.
`6/2009 Biggadike
`11/2009 Myles et al.
`6/2010 Fuge et al.
`12/2010 Biggadike et al.
`3/2012 Myles et al.
`3/2015 Lulla et al.
`
`FOREIGN PATENT DOCUMENTS
`
`............. A61K 31/57
`
`DE
`DE
`DE
`DE
`DE
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`GB
`GB
`GB
`GB
`GB
`GB
`GB
`GB
`GB
`IL
`JP
`JP
`JP
`JP
`
`6/1959
`1059906 B
`7 /1972
`2164058 Al
`5/1989
`3836579 Al
`19947234 Al
`4/2001
`5/2002
`10152369 Al
`10/1979
`0004773 A2
`0057401 Al
`8/1982
`4/1986
`0179583 Al
`10/1990
`0393658 Bl
`3/1991
`0416951 Al
`0780127 Al * 6/1997
`4/2009
`1519731 Bl
`2072051 Al
`6/2009
`2075000 Al
`7/2009
`1191965
`5/1970
`1296458
`11/1972
`1384372
`2/1975
`1438940
`6/1976
`1517278
`7 /1978
`2079755 A
`1/1982
`2088877 A
`6/1982
`2140800 A
`12/1984
`2389530 A
`12/2003
`109656 A
`2/1998
`4208267 A
`7 /1992
`8291072 A
`11/1996
`8291073 A
`11/1996
`200253485 A
`2/2002
`
`A61K 9/0043
`514/646
`
`A61K 9/006
`424/130.1
`
`

`

`(56)
`
`References Cited
`
`FOREIGN PATENT DOCUMENTS
`
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`
`8504589 Al
`8903390 Al
`9015816 Al
`9104252 Al
`9214472 Al
`9408551 A2
`9531964 Al
`9619199 Al
`9619969 Al
`9632151 Al
`9701337 Al
`9705136 Al
`9715298 Al
`9721721 Al
`9721724 Al
`9724365 Al
`9731626 Al
`9740836 Al
`9746243 Al
`9817676 Al
`9824450 Al
`9834596 A2
`9848839 Al
`9901467 A2
`9925359 Al
`9932089 Al
`0016814 Al
`0027373 Al
`0033892 Al
`0038811 Al
`0041816 Al
`0048587 Al
`0049993 A2
`0066522 Al
`0104118 A2
`01020331 Al
`0122955 A2
`0154481 A2
`0154664 Al
`0157025 Al
`0162722 A2
`0178736 Al
`0178739 Al
`0178741 Al
`0178745 Al
`0200199 Al
`0200679 A2
`0202565 A2
`0207767 A2
`0208243 Al
`0211711 A2
`0212265 Al
`0212266 Al
`0213868 Al
`0226723 Al
`0236106 A2
`02051422 Al
`02053186 A2
`02066422 Al
`02070490 Al
`02076933 Al
`02085296 A2
`02088167 Al
`02100879 Al
`03000241 A2
`03013427 A2
`03033000 Al
`03035668 A2
`03040691 A2
`03042229 Al
`03042230 Al
`03048181 Al
`03062259 A2
`03064445 Al
`03066033 Al
`
`10/1985
`4/1989
`12/1990
`4/1991
`9/1992
`4/1994
`11/1995
`6/1996
`7 /1996
`10/1996
`1/1997
`2/1997
`5/1997
`6/1997
`6/1997
`7 /1997
`9/1997
`11/1997
`12/1997
`4/1998
`6/1998
`8/1998
`11/1998
`1/1999
`5/1999
`7 /1999
`3/2000
`5/2000
`6/2000
`7/2000
`7/2000
`8/2000
`8/2000
`11/2000
`1/2001
`3/2001
`4/2001
`8/2001
`8/2001
`8/2001
`8/2001
`10/2001
`10/2001
`10/2001
`10/2001
`1/2002
`1/2002
`1/2002
`1/2002
`1/2002
`2/2002
`2/2002
`2/2002
`2/2002
`4/2002
`5/2002
`7/2002
`7/2002
`8/2002
`9/2002
`10/2002
`10/2002
`11/2002
`12/2002
`1/2003
`2/2003
`4/2003
`5/2003
`5/2003
`5/2003
`5/2003
`6/2003
`7/2003
`8/2003
`8/2003
`
`US 9,901,585 B2
`Page 3
`
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`ZA
`
`03066036 Al
`03066656 Al
`03072592 Al
`03086399 Al
`03105856 Al
`2004013156 Al
`2004019955 Al
`2005005451 Al
`2005005452 Al
`2006058022 Al
`2007061454 Al
`2008012338 A2
`2008012338 A3
`872389
`
`8/2003
`8/2003
`9/2003
`10/2003
`12/2003
`2/2004
`3/2004
`1/2005
`1/2005
`6/2006
`5/2007
`1/2008
`1/2008
`4/1987
`
`OTHER PUBLICATIONS
`Applicant response to foreign communication European Patent
`1519731, dated Aug. 11, 2011, 252 pages.
`Applicants' response dated Feb. 24, (2010) 2011 (8 pages) in U.S.
`Appl. No. 12/374,523, filed Jan. 21, 2009.
`Applicants' response dated Jun. 22, 2011 (9 pages) in U.S. Appl.
`No. 12/374,523, filed Jan. 21, 2009.
`Applicants' response dated Oct. 6, 2010 (8 pages) in U.S. Appl. No.
`12/374,523, filed Jan. 21, 2009.
`Applicants' response dated Sep. 6, 2011 (8 pages) in U.S. Appl. No.
`12/374,523, filed Jan. 21, 2009.
`Applicant response to foreign communication----CA 2489427, dated
`Dec. 20, 2010, 10 pages.
`Applicant response to foreign communication-EP 03738280.1 (EP
`Patent 1519731), dated Sep. 6, 2010, 15 pages.
`Applicant response to foreign communication-EP 03738280.1,
`dated Jan. 18, 2008, 14 pages.
`Applicant response to foreign communication-EP 03738280.1,
`dated May 22, 2006, 36 pages.
`Applicant response to foreign communication-KR 10-2004-
`7020819, dated Dec. 27, 2010, 18 pages.
`Astelin® (azelastine hydrochloride) Nasal Spray, Physicians' Desk
`Reference, 2002, pp. 3339-3340 plus one page Product Information,
`Wallace Laboratories.
`Astelin (azelastine hydrochloride) Nasal Spray, 2006, U.S. Physi(cid:173)
`cians Desk Reference, pp. 1876-1877 plus cover page, MedPointe
`Pharmaceuticals.
`Astepro (azelastine HCI) Nasal Spray 0.15%, Meda Pharmaceuti(cid:173)
`cals Inc., Sep. 2, 2009, Press Release, pp. 1-4.
`Aurora, Jack, "Nasal Delivery; Development of Nasal Delivery
`Systems: A Review," Drug Delivery Technology, vol. 2, No. 7, Oct.
`2002, 8 pages, http://www.drugdeliverytech.com/ME2/Segments/
`Publications:Article
`&id~9EB 19EB2F29F462089CE08 l 4 73F 5F3CA.
`Austin, R.J.H., et al., "Mometasone furoate is a less specific
`glucocorticoid than fluticasone propionate," European Respiratory
`Journal, 2002, vol. 20, pp. 1386-1392.
`and
`Cellulose
`Avicel®
`RC/CL,
`Microcrystalline
`Carboxymethylcellulose Sodium, NF Dispersible Cellulose, BP,
`Specifications and Analytical Methods, RC-16 Updated Oct. 1995
`(Feb. 1999), 6 pages, FMC Corporation.
`Azelastine, STN Registry No. 58581-89-8, STN Registry File,
`Retrieved Nov. 23, 2010, 1 page.
`Baena-Cagnani, Carlos E., "Safety and Tolerability of Treatments
`for Allergic Rhinitis in Children," Drug Safety, 2004, vol. 27, No.
`12, pp. 883-898, ADIS Data Information BV.
`Banov, Charles H., et al., "Once daily intranasal fluticasone
`propionate is effective for perennial allergic rhinitis," Annals of
`Allergy, Sep. 1994, vol. 73, pp. 240-246.
`Barnes, M. L., et al., "Effects of levocetirizine as add-on therapy to
`fluticasone in seasonal allergic rhinitis," Clinical and Experimental
`Allergy, 2006, vol. 36, pp. 676-684, Blackwell Publishing Ltd.
`Barnes, Peter J., "Chronic obstructive pulmonary disease: new
`opportunities for drug development," TiPS, vol. 19, Oct. 1998, pp.
`415-4 23, Elsevier Science Ltd.
`Barnes, Peter J., "Efficacy of inhaled corticosteroids in asthma," The
`Journal of Allergy and Clinical Immunology, vol. 102, No. 4, Part
`1, Oct. 1998, pp. 531-538, Mosby, Inc.
`
`

`

`US 9,901,585 B2
`Page 4
`
`(56)
`
`References Cited
`
`OTHER PUBLICATIONS
`
`Barnes, Peter J., "Novel approaches and targets for treatment of
`chronic obstructive pulmonary disease," American Journal of
`Respiratory and Critical Care Medicine, vol. 160, 1999, pp. S72-
`S79.
`Baumgarten, C., et al., "Initial treatment of symptomatic mild to
`moderate bronchial asthma with
`the
`salmeterol/fluticasone
`propionate (50/250 µg) combination product (SAS 40023)," Euro(cid:173)
`pean Journal of Medical Research, Jan. 29, 2002, vol. 7, pp. 1-7, I.
`Holzapfel Publishers.
`Berge, Stephen M., et al., "Pharmaceutical Salts," Journal of Phar(cid:173)
`maceutical Sciences, vol. 66, No. 1, Jan. 1977, pp. 1-19.
`Berstein, D. I., et al., "Treatment with intranasal fluticasone
`propionate significantly improves ocular symptons in patients with
`seasonal allergic rhinitis," Clinical and Experimental Allergy, 2004,
`vol. 34, pp. 952-957, Blackwell Publishing Ltd.
`Biggadike, Keith, "Fluticasone furoate/fluticasone propionate(cid:173)
`different drugs with different properties," Letter to the Editor, The
`Clinical Respiratory Journal, pp. 183-184, 2011, Blackwell Pub(cid:173)
`lishing Ltd.
`Block, John H., et al., "Inorganic Medicinal and Pharmaceutical
`Chemistry," 1986, cover, publication, and preface pages plus p. 100,
`Indian Edition, Varghese Publishing House, Bombay, India.
`Bowler, Simon, "Long acting beta agonists," Australian Family
`Physician, vol. 27, No. 12, Dec. 1998, pp. 1115, 1117-1118.
`Brooks, Carter D., et al., "Spectrum of seasonal allergic rhinitis
`symptom relief with topical corticoid and oral antihistamine given
`singly or in combination," American Journal of Rhinology, May(cid:173)
`Jun. 1996, vol. 10, No. 3, pp. 193-199.
`Bryson, Harriet M., et al., "Intranasal fluticasone propionate: a
`review of its pharmacodynamic and pharmacokinetic properties,
`and therapeutic potential in allergic rhinitis," Drugs, 1992, vol. 43,
`No. 5, pp. 760-775, Adis International Limited.
`Busse, William, et al., "Steroid-sparing effects of fluticasone
`propionate 100 µg and salmeterol 50 µg administered twice daily in
`a single product in patients previously controlled with fluticasone
`propionate 250 µg administered twice daily," J Allergy Clin
`Immunol, vol. 111, No. 1, Jan. 2003, pp. 57-65, Mosby, Inc.
`Busse, William W., et al., "Corticosteroid-sparing effect of
`azelastine in the management of bronchial asthma," XP-000604179,
`American Journal of Respiratory and Critical Care Medicine, 1996,
`pp. 122-127, vol. 153.
`CAS Registry No. 102113-40-6, 2004, 1 page, ACS on STN.
`CAS Registry No. 90566-53-3, "Fluticasone," Entered STN: Nov.
`16, 1984, 1 page, © 2008 ACS on STN.
`Chapman, Richard W., et al., "Anti-inflammatory activity of inhaled
`mometasone furoate in allergic mice," Arzneim.-Forsch./Drug Res.,
`1998, vol. 48, No. 4, pp. 384-391.
`CIPLA Annual Report Extract, 2010 (report shows that they
`launched an FF+azelastine product in 2010), 103 pages.
`Cipla Sixty-Ninth Annual Report 2004-2005, cover pages, infor(cid:173)
`mation page, plus pp. 3, 5, and 44.
`CIPLA's response to Statement of Opposition for EP1519731, 11
`pages, 2002.
`Comparative data of azelastine with steroids, 2011, 4 pages.
`Daley-Yates, Peter T., et al., "Systemic bioavailability offluticasone
`propionate administered as nasal drops and aqueous nasal spray
`formulations," Br J Clin Pharmocol., 2001, vol. 51, pp. 103-105,
`Blackwell Science Ltd.
`Declaration of Geena Malhotra for EP151973 l dated Aug. 11, 2011,
`4 pages.
`Declaration of Joachim Maus for EP1519731 dated Aug. 10, 2011,
`6 pages.
`Derby, Laura, et al., "Risk of cataract among users of intranasal
`corticosteroids," J Allergy Clin Immunol, 2000, vol. 105, No. 5, pp.
`912-916, Mosby, Inc.
`Dewester, Jeffrey, et al., "The efficacy of intranasal fluticasone
`propionate in the relief of ocular symptoms associated with seasonal
`allergic rhinitis," Allergy and Asthma Proc., Sep.-Oct. 2003, vol. 24,
`No. 5, pp. 331-337.
`
`Dictionary of Organic Compounds, definition of "fluticasone,"
`Sixth Edition, 1996, vol. 1, p. 3234 plus cover and publishing pages,
`Chapman & Hall.
`Di Lorenzo, G., et al., "Randomized placebo-controlled trial com(cid:173)
`paring fluticasone aqueous nasal spray in mono-therapy, fluticasone
`plus cetirizine, fluticasone plus montelukast and cetirizine plus
`montelukast for seasonal allergic rhinitis," Clinical and Experimen(cid:173)
`tal Allergy, 2004, vol. 34, pp. 259-267, Blackwell Publishing Ltd.
`Dolovich, Jerry, et al., "Multicenter trial of fluticasone propionate
`aqueous nasal spray in ragweed allergic rhinitis," Annals of Allergy,
`Aug. 1994, vol. 73, pp. 147-153.
`Notice of Allowance dated Nov. 18, 2015 (29 pages), U.S. Appl. No.
`14/661,720, filed Mar. 18, 2015.
`Duonase Data Sheet, "The Complete Rhinitis Control," 6 pages,
`Cipla Limited, Mumbai, India, 2002.
`Dykewicz, Mark S., et al., "Diagnosis and Management of Rhinitis:
`Complete Guidelines of the Joint Task Force on Practice Parameters
`in Allergy, Asthma and Immunology," Annals of Allergy, Asthma, &
`Immunology, vol. 81, Nov. 1998 (Part II) , pp. 478-518.
`File history of Australian Patent Application No. AU2003244799,
`38 pages.
`File history of Brazilian Patent Application No. PI 0312128-3, 27
`pages, 2002.
`File history of Canadian Patent Application No. 2,489,427, 19
`pages, 2002.
`File history of Korean Patent Application No. 10-2004-7020819, 89
`pages.
`File history of Mexican Patent Application No. PA/a/2004/01266
`(now Patent No. 265349), 86 pages.
`File history of Polish Patent Application No. P-373001, 95 pages,
`dated May 2011, 2002.
`File history of Russian Patent Application No. RU 2361593 C2, 65
`pages, dated Apr. 2009.
`File history of South African Patent Application No. 2005/0331
`(now Patent No. 2005/0331), 18 pages.
`Fluticasone Furoate, STN Registry No. 397864-44-7, Entered STN:
`Mar. 4, 2002, 1 page, © 2010 ACS on STN.
`Foreign communication from a related counterpart application(cid:173)
`Australian Application No. 2003244799, Examination Report, dated
`Nov. 20, 2007, 2 pages.
`Foreign communication from a related counterpart application(cid:173)
`Canadian Application No. 2,489,427, Examination Report, dated
`Jun. 18, 2010, 3 pages.
`Foreign communication from a related counterpart application(cid:173)
`Canadian Application No. 2,489,427, Examination Report, dated
`Mar. 24, 2011, 2 pages.
`Foreign communication from a related counterpart application(cid:173)
`Examination Report, European Application No. 03738280.1, dated
`Jul. 18, 2007, 5 pages.
`Foreign communication from a related counterpart application(cid:173)
`Examination Report, European Application No. 03738280.1, dated
`Nov. 10, 2005, 4 pages.
`Foreign communication from a related counterpart application(cid:173)
`European Application No. 03738280.1, Notice of Intent to Grant,
`dated Oct. 23, 2008, 6 pages.
`Foreign communication from a related counterpart application(cid:173)
`Examination Report, Russian Application No. 2005100781, dated
`Apr. 23, 2007, 6 pages.
`Foreign communication from a related counterpart application(cid:173)
`Examination Report, Russian Application No. 2005100781, dated
`May 23, 2008, 3 pages.
`Foreign communication from a related counterpart application(cid:173)
`Korean Application No. 10-2004-7020819, Examination Report,
`dated Aug. 26, 2010, 8 pages.
`Foreign communication from a related counterpart application(cid:173)
`Notice of Opposition, European Application No. 03738280.1, dated
`Feb. 22, 2010, 22 pages.
`Foreign communication from a related counterpart application(cid:173)
`Summons to Attend Oral Proceedings, European Application No.
`03738280.1, dated Feb. 8, 2011, 1 page.
`Foreign communication from a related counterpart application(cid:173)
`Translation of Office Action, Israeli Patent Application No. 165771,
`dated Jul. 11, 2011, 3 pages.
`
`

`

`US 9,901,585 B2
`Page 5
`
`(56)
`
`References Cited
`
`OTHER PUBLICATIONS
`
`Foreign communication from the priority application-Interna(cid:173)
`tional Preliminary Examination Report, PCT/GB03/02557, dated
`Aug. 26, 2004, 6 pages.
`Foreign communication from the priority application-Interna(cid:173)
`tional Search Report, PCT/GB03/02557, dated Sep. 17, 2003, 3
`pages.
`Foreign communication from the priority application-Search
`Report, Great Britain Application No. 0213739.6, dated Nov. 22,
`2002, 4 pages.
`Foreign communication from a related counterpart application(cid:173)
`First Examination Report, Indian Application No. 1696/MUMNP/
`2009, dated Jun. 27, 2012, 2 pages.
`Foreign communication from a related counterpart application(cid:173)
`First Examination Report, Indian Application No. 1695/MUMNP/
`2009, dated Jun. 29, 2012, 2 pages.
`Foreign communication from a related counterpart application(cid:173)
`Final Office Action, Korean Application No. 10-2011-7022532,
`dated Aug. 24, 2012, 6 pages.
`Foreign communication from a related counterpart application(cid:173)
`Final Office Action, Korean Application No. 10-2011-7022533,
`dated Aug. 24, 2012, 6 pages.
`Foreign communication from a related counterpart application(cid:173)
`Office Action, European Application No. 0907 5100 .9, dated Aug. 8,
`2012, 6 pages.
`Foreign communication from a related counterpart application(cid:173)
`EPO Communication, European Application No. 09075101. 7, dated
`Aug. 8, 2012, 5 pages.
`Fowler, Stephen J., et al., "Step-down therapy with low-dose
`fluticasone-salmeterol
`combination
`or
`medium-dose
`hydrofluoroalkane 134a-beclomethasone alone," J Allergy Clin
`Immunol, vol. 109, No. 6, Jun. 2002, pp. 929-935, Mosby, Inc.
`Galant, Stanley P., et al., "Clinical Prescribing of Allergic Rhinitis
`Medication in the Preschool and Young School-Age Child; What are
`the Options?," BioDrugs, 2001, vol. 15, No. 7, pp. 453-463, ADIS
`International Limited.
`Garner, R. C., et al., "A validation study comparing accelerator MS
`and liquid scintillation counting for analysis of 14C-labelled drugs
`in plasma, urine and faecal extracts," Journal of Pharmaceutical and
`Biomedical Analysis, vol. 24, 2000, pp. 197-209, Elsevier Science
`B.V.
`intranasal
`"Comparison of
`et al.,
`Gawchik, Sandra M.,
`triamcinolone acetonide with oral loratadine in the treatment of
`seasonal ragweed-induced allergic rhinitis," The American Journal
`of Managed Care, Jul. 1997, vol. 3, No. 7, pp. 1052-1058.
`Gennaro, Alfonso R., et al., Remington: The Science and Practice of
`Pharmacy, 2000, 20th edition, vol. 1, pp. 785, 830, 831 plus cover
`page and publication pages, Lippincott Williams & Wilkins, a
`Walters Kluwer Company.
`Gilbert, Peter, et al., "Preservation of Pharmaceutical Products,"
`Encyclopedia of Pharmaceutical Technology, 2002, 2nd edition,
`vol. 3, p. 2278 plus cover page and publication pages, Marcel
`Dekker, Inc.
`Hampel, Frank C., et al., "Double-blind, placebo-controlled study of
`azelastine and fluticasone in a single nasal spray delivery device,"
`Annals of Allergy, Asthma & Immunology, vol. 105, pp. 168-173,
`Aug. 2010, American College of Allergy, Asthma & Immunology.
`Harding, S. M., "The human pharmacology of fluticasone
`propionate," Respiratory Medicine, 1990, vol. 84, Suppl. A, pp.
`25-29, Bailliere Tindall.
`Herrero, Varnell R., "Preservatives in Ophthalmic Formulations: An
`Overview," Arch Soc Esp Oftalmol, 2007, vol. 82, pp. 531-532.
`Hodges, N. A., et al., "Preservative Efficacy Tests in Formulated
`Nasal Products: Reproducibility and Factors Affecting Preservative
`Activity," J. Pharm. Pharrnacol., 1996, vol. 48, pp. 1237-1242.
`Hodges, Norman, et al., "Antimicrobial Preservative Efficacy Test(cid:173)
`ing," Handbook of Microbiological Quality Control, Pharmaceuti(cid:173)
`cals and Medical Devices, 2000, p. 168 plus cover page and
`publication pages, Taylor & Francis and Rosamund M. Barid,
`Norman A. Hodges, and Stephen P. Denyer.
`
`Holgate, Stephen T., et al., "Difficult Asthma," 1999, cover page and
`publishing information, Martin Dunitz Ltd.
`Howarth, P.H., "A comparison of the anti-inflanunatory properties
`of intranasal corticosteroids and antihistamines in allergic rhinitis,"
`Allergy 2000, vol. 62, pp. 6-11, Munksgaard 2000.
`Howland, III, W. C., "Fluticasone propionate: topical or systemic
`effects?" Clinical and Experimental Allergy, 1996, vol. 26, Suppl. 3,
`pp. 18-22, Blackwell Science Ltd.
`Isogai, Mitsutaka, et al., "Binding affinities of mometasone furoate
`and
`related compounds
`including
`its metabolites
`for
`the
`glucocorticoid receptor of rat skin tissue," J. Steroid Biochem.
`Molec. Biol., 1993, vol. 44, No. 2, pp. 141-145, Peragom Press Ltd.
`Flonase Nasal Spray, 0.05% w/w Product Information, 8 pgs., Sep.
`1994, Allen & Hanburys, Division of Glaxo Inc.
`FLOY.ENT Prescribing Information, GlaxoSmithKline, 19 pgs,
`2002.
`FLOY.ENT Rotadisk Prescibing Information, GlaxoSmithKline, 21
`pgs, 2002.
`Foreign communication from a related counterpart application(cid:173)
`Communication of a Notice of Opposition, European Application
`No. 09075101.7, dated Nov. 5, 2014, 27 pages.
`Foreign communication from a related counterpart application(cid:173)
`Communication of Further Notices of Opposition, European Appli(cid:173)
`cation No. 09075101.7, dated Dec. 5, 2014, 95 pages.
`Giede, C., et al., "Comparison of Azelastine Eye Drops with
`Levocabastine Eye Drops in the T reatrnent of Seasonal Allergic
`Conjunctivitis," Current Medical Research and Opinion®, 2000, pp.
`153-163, vol. 16, No. 3, LibraPharm Limited.
`Lee, et al., "How to treat allergic rhinitis," Medicine Cabinent, WJM
`Western J. of Med., Jul. 1999, pp. 31-34, vol. 171.
`Mabry, R.L., "Recent advances in pharmacotherapy of allergic
`rhinitis," Current Opinion in Otolaryngology & Head and Neck
`Surgery 1999, pp. 375-378 vol. 7, No. 6.
`Office Action dated Oct. 17, 2008 (28 pages), U.S. Appl. No.
`10/518,016, filed Jul. 6, 2005.
`Astelin Nasal Spray, Sep. 29, 1997, Package Insert.
`Advair™ Diskus®, Final Printed Labeling, Center for Drug Evalu(cid:173)
`ation and Research, Aug. 2000, 42 pages, GlaxoWellcome Inc.
`Advair™ Diskus®, Printed Labeling, Revised: Apr. 2008, 62 pages,
`GlaxoSmithKline.
`Aistars, Arnis, "Optimizing Antimicrobial Preservative Selection
`for Pharmaceutical Products," Spectrum Excipients Bulletin, Dec.
`2011, 5 pages.
`Backhouse, C. I., et al., "Treatment of Seasonal Allergic Rhinitis
`with Flunisolide and Terfenadine," J. Int. Med. Res., 1986, vol. 14,
`No. 1, pp. 35-41 plus cover page.
`Banker, Gilbert S., et al., "Modern Pharmaceutics," 4th ed., 2002,
`3 pages, Marcel Dekker, Inc.
`Davies, Robert J., et al., "Once-Daily Mometasone Furoate Nasal
`Spray: Efficacy and Safety of a New Intranasal Glucocorticoid for
`Allergic Rhinitis," Clinical Therapeutics®, 1997, pp. 27-38, vol. 19,
`No. 1.
`Falser, Norbert, et al., "Comparative Efficacy and Safety of
`Azelastine and Levocabastine Nasal Sprays in Patients with Sea(cid:173)
`sonal Allergic Rhinitis," Arzneim.-Forsch./Drug Res., 2001, pp.
`387-393, vol. 51, No. 1, ECV (Editio Cantor Verlag), Germany.
`Flonase® (fluticasone proprionate) Nasal Spray, 50 mcg, Final
`Printed Labeling, Center for Drug Evaluation and Research, 1998,
`13 pages, GlaxoWellcome Inc.
`Johansson, Gunnar, et al., "Comparison of salmeterol/fluticasone
`propionate combination with budesonide in patients with mild-to(cid:173)
`moderate
`asthma,"
`http://www.medscape.com/viewarticle/
`406237_print, [Clin Drug Invest, vol. 21, No. 9, 2001, pp. 633-
`642], Adis International Limited.
`Johnson, Malcom, "Development of fluticasone propionate and
`comparison with other inhaled corticosteroids," J Allergy Clin
`Immunol, Apr. 1998, vol. 101, No. 4, Part 2, pp. S434-S439, Mosby,
`Inc.
`Juniper, E. F., et al., "Comparison ofbeclomethasone dipropionate
`aqueous nasal spray, astemizole, and the combination in the pro(cid:173)
`phylactic treatment of ragweed pollen-induced rhinoconjunctivitis,"
`Journal of Allergy and Clinical Immunology, Mar. 1989, vol. 83,
`
`

`

`US 9,901,585 B2
`Page 6
`
`(56)
`
`References Cited
`
`OTHER PUBLICATIONS
`
`No. 3, cover and publication pages, pp. 627-633, American Acad(cid:173)
`emy of Allergy and Immunology, C.V. Mosby Co.
`Juniper, Elizabeth F., et al., "Impact of inhaled salmeterol/
`fluticasone propionate combination product versus pudesonide on
`the health-related quality of life of patients with asthma," Am J
`Respir Med, vol. 1, No. 6, 2002, pp. 435-440, Adis International
`Limited.
`Kenley, Richard A., et al., "An automated, column-switching HPLC
`method for analyzing active and excipient materials in both cream
`and ointment formulations," Drug Development and Industrial
`Pharmacy, vol. 11, No. 9 & 10, 1985, pp. 1781-1796, Marcel
`Dekker, Inc.
`Kertesz, Denis J., et al., "Thiol esters from steroid 17!3-carboxylic
`acids: carboxylate activation and internal participation by 17
`a-acylates," J. Org. Chem., vol. 51, 1986, pp. 2315-2328 (14 pages).
`Knobil, K., et al., "Adding salmeterol is more effective than
`increasing the dose of fluticasone for patients with asthma who are
`symptomatic on low dose fluticasone," European Respiratory Jour(cid:173)
`nal, vol. 12, Suppl. 29, Dec. 1998, pp. 19s-20s plus 1 cover page,
`Ref. No. Pl60.
`J., et al., "The synthesis of 17-esters of
`Kooreman, H.
`corticosteroids protection of 1113-hydroxyl of the trimethylsilyl
`group," Synthetic Communications, vol. 1, No. 2, pp. 81-87, 1971,
`Marcel Dekker, Inc.
`Laforce, Craig F., et al., "Fluticasone propionate: an effective
`alternative treatment for seasonal allergic rhinitis in adults and
`adolescents," The Journal of Family Practice, 1994, vol. 38, No. 2
`(Feb), pp. 145-152, Appleton & Lange.
`capillary
`"Evaluation of a new
`Lane, S.
`J.,
`et