c909L30.iiIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII
`
`PROISB/05 (04-05)
`.
`Approved for use through 07/31/2006. OMB 0651-0032
`U.S. Patent and Trademark Office; U.S. DEPARTMENT OF COMMERCE
`_
`he-fiaenrvork Reduction Act of 1995, no ersons are reuired to respond to a collection of information unless it displa s a valid OMB control number
`
`L
`
`PATENT APPLICATION
`TRANSMITTAL
`(Only for new nonprovlsional applications under 37 CFR 1.53(b))
`
`Attomey Docket No.
`
`Firstlnventor
`
`Express Mail Label No.
`
`APPLICATION ELEMENTS
`See MPEP chapter 600 concerning utility patent application contents.
`
`'
`ADDRESS TO‘
`
`64507-5014-US
`
`BAKER. stenen J.
`BORON-CONTAINING SMALL ” I
`MOLECULES
`C")
`Ev553729231us
`Commissioner for Patents
`.
`.
`14
`P O Box
`50
`Alexandria VA 22313-1450
`
`:
`
`1. E Fee Transmittal Form (e.g., PTOISBI17)
`(Submit an original and a duplicate for fee processing)
`2. 8 Applicant claims small entity status.
`See 37 CFR127.
`111
`3. E Specification
`[Total Pages
`Both the claims and abstract must start on a new page
`(For information on the preferred arrangement, see MPEP 608. 01(a))
`4. IZDrawing(s) (35 U. S. 113)
`[Total Sheets
`12
`|
`
`ACCOMPANYING APPLICATION PARTS
`
`9. U Assignment Papers (cover sheet 8. document(s))
`
`Name of Assignee
`
`[Total SheetsLi 1o_ [1 37 cm 313(5) statement
`5. Doath or Declaration
`a. E] Newly executed (original or copy)
`(When there /5 3" 355i9"59)
`.
`.
`b. E] A copy from a prior application (37 CFR 1.63(d)
`.
`.
`(for continuation/divisional with Box 18 completed)
`11' D Enghsh Transmlon Document (If apphcame)
`i. U DELETION OF INVENTORIS)
`12. D information Disclosure Statement (PT0lSBl08 or PTO-1449)
`Signed statement attached deleting inventor(s) name
`C] Copies of citations attached
`in the prior application, see 37 CFR 1.63(d)(2) and
`1.33(b).
`6. EApplication Data Sheet. See 37 CFR 1.76
`
`E] Power of
`Attorney
`
`7. DCD-ROM or CD-R in duplicate, large table or
`Computer Program (Appendix)
`El Landscape Table on CD
`8. CI Nucleotide andlor Amino Acid Sequence Submission
`(if applicable, items a. — c. are required)
`a. C] Computer Readable Form CRF)
`b.
`Specification Sequence Listing on:
`
`i. CI CD-ROM or COR (2 copies); or
`ii.I'_‘l Paper
`Statements verifying identity of above copies
`
`13. D Preliminary Amendment
`14.
`IX] Return Receipt Postcard (MPEP 503)
`(Should be specifically itemized)
`
`15. El Certified Copy of Priority Document(s)
`(if foreign priority is claimed)
`16. El Nonpubllcatlon Request under 35 U.S.C. 122(b)(2)(B)(i)
`Applicant must attach form PTOISBI35 or equivalent.
`
`.
`
`17. D Omen
`
`18. [I if a CONTINUING APPLICATION, check appropriate box, and supply the requisite information below and in the first sentence of the specification following their title, or
`in an Application Sheet under 37'CFR 1.76:
`
`CI Continuation
`Prior application information:
`
`CI Divisional
`Examiner
`
`E] Continuation-in-part(C|P)
`
`Of Pfiof application N0. ................................... ..
`Art Unit:
`
`19. CORRESPONDENCE ADDRESS
`
`‘
`
`E The address associated with Customer Number.
`
`OR El Correspondence address below
`
`Ia
`
`Todd Esker
`
`Registration No.
`Attorne IA ent
`This ¢°”9¢1i°n 07 inlomlaiion is required DY 37 CFR 1-53(b). The inlonnation is required to obtain or retain a benefit by the public which is to file (and by the USPTO to process) an application. Confidentiality is
`governed by 35 USC. 122 and 37 CFR 1.11 and 1.14. This collection is estimated to take 12 minutes to complete, including gathering, preparing. and submitting the completed application form to the USPTO.
`Time will vary depending upon the individual case. Any comments on the amount oi time you require to complete this tonn andlor suggestions for reducing this burden, should be sent to the chiral information
`Olficer, US. Patent and Trademark Office, U.S. Department of Commerce, PO. Box 1450, Alexandria, VA 22313-1450. DO NOT SEND FEES OR COMPLETED FORMS TO THIS ADDRESS. SEND TO:
`Commissioner tor Patents. P.O. Box 1450, Alexandria. VA 22313-1450.
`1-SF/7343079.1
`
`t-
`
`7
`
`CFAD v. Anacor, IPR2015-01776, CFAD EXHIBIT 1070 - Page 1 of 558
`
`

`
`iiiiiiiiiiiiiiiiiiiiiiiiiiii
`
`PTOISB/17 (12-04)
`Approved for use through 07/31/2006. OMB 0651-0032
`US. Patent and Trademark Office; U.S. DEPARTMENT OF COMMERCE
`Underlhe Paenivork Reduction Act of 1995 no - -
`uired to res - nd to a collemion of inlormation unless it dis la s a valid OMB control number
`.
`Com . Iete if Known
`Effective on 12/08/2004.
`. Fees pursuant to the Consolidated Appropriations Act, 2005 (HR. 4818). A . “cation Number
`Not Yet Assi. ned
`FEE '|"RANS|V||TTA|_
`Filin Date
`Februa
`16,2006
`First Named Investor
`Baker, Stehen J.
`~oweiAssineu
`Not Yet Assi ned
`64507-5014-US
`
`For FY 2005
`A E A Iicant claims small enti
`status. See 37 CFR 1.27
`Total Amount of Pa ment
`($) 1100.00
`
`Art Unit
`Attorne Docket No.
`
`-
`
`METHOD OF PAYMENT (check all that apply)
`D Check E] Credit Card I:IMoney Order CI None D Other (plem identify):
`El Deposit Account Deposit Account Number 50-0310
`Deposit Account Name: Morgan, Lewis 8. Bockius LLP
`For the above-identified deposit account, the Director is hereby authorized to: (check all that apply)
`
`[I Charge fee(s) indicated below, except for the filing fee
`IE Charge fee(s) indicated below
`E Charge any additional fee(s) or underpayments of E Credit any overpayments
`fee(s) under 37 CFR 1.16 and 1.17
`WARNING: Information on this form may become public. Credit card information should not be included on this form. Provide credit card
`information and authorization on PTO-2038.
`FEE CALCULATION
`1. BASIC FILING, SEARCH. AND EXAMINATION FEES
`FILING FEES
`SEARCH FEES
`Small Entity
`Small Entig
`Fee (§1
`Fee (§)
`150
`250
`100
`50
`100
`150
`150
`250
`100
`0
`
`Agplication Type Fee (§)
`Utility
`300
`Design
`200
`Plant
`200
`Reissue
`300
`Provisional
`200
`
`Fee (5)
`500
`100
`300
`500
`0
`
`EXAMINATION FEES
`Small Entig
`Fee l§1
`100
`65
`80
`300
`0
`
`Fee ifl
`200
`130
`160
`600
`0
`
`2. EXCESS CLAIM FEES
`Fee Description
`Each claim over 20 or, for Reissues, each claim over 20 and more than in the original patent
`Each independent claim over 3 or. for Reissues, each independent claim more than in the original patent
`Multiple dependent claims
`Extra Claims
`Total Claims
`_39j - 20 or HP = _19j x
`HP = highest number of total claims paid for, if greater than 20
`lndeg. Claims
`Extra Claims
`x
`- 3 or HP =
`3
`HP = highest number of total claims paid for, if greater than 3
`3. APPLICATION SIZE FEE
`If the specification and drawings exceed 100 sheets of paper, the application size fee due is $250 ($125 for small entity) for each
`additional 50 sheets or fraction thereof. See 35 U.S.C. 41(a)(1)(G) and 37 CFR 1.16(s).
`Total Sheets
`Extra Sheets
`Number of each additional 50 or fraction thereof Fee(§)
`123
`23
`/ 50 =
`(round up to a whole number)
`x
`
`- 100 =
`
`Fee Paid Q)
`125
`
`4. OTHER FEE(S)
`Non-English Specification, $130 fee (no small entity discount)
`Other:
`
`Fees Paid (§[
`
`/"
`
`Registration No. 46,690
`’
` Amme /A em
`?
`Todd Esker
`
`Telephone (415) 442-1304
`Date February 16, 2006
`This collection of intonnation is required by 37 CFR 1.136, The intonnation is required to obtain or retain a benefit by the public which is to file (and by
`the USPTO to process) an application. Confidentiality is governed by 35 U.S.C. 122 and 37 CFR 114. This collection is estimated to take 30 minutes
`to complete. including gathering. preparing. and submitting the completed application form to the USPTO. Time will vary depending upon the individual
`case, Any comments on the amount of time you require to complete this form andlor suggestions for reducing this burden, should be sent to the Chief
`information Oificer, US. Patent and Trademark Office, U.S. Department of Commerce, PO. Box 1450, Alexandria, VA 22313-1450. DO NOT SEND
`FEES OR COMPLETED FORMS TO THIS ADDRESS. SEND TO: Commissioner for Patents, P.O. Box 1450, Alexandria, VA 22313-1450.
`Ifyou need assistance in completing the fonn, call 1-800-PTO-9199 and select option 2.
`
`SUBMITTED BY
`
`Name (Print/Type)
`
`1-SFI73430B7.1
`
`Small Entity
`Fee 1§)
`Fee ($1
`25
`50
`100
`200
`180
`360
`Multigle Degendent Claims
`Fee ($1)
`Fee Paid ($1)
`
`Fee (§)
`25
`
`Fee (§)
`
`Fee Paid (5)
`475___
`
`Fee Paid Q)
`
`CFAD v. Anacor, IPR2015-01776, CFAD EXHIBIT 1070 - Page 2 of 558
`
`

`
`c909L30.iiIIIIIIIIIIIIIIIIIIIIIIIIIIIIIII
`
`PROISB/05 (04-05)
`.
`Approved for use through 07/31/2006. OMB 0651-0032
`U.S. Patent and Trademark Office; U.S. DEPARTMENT OF COMMERCE
`_
`he-fiaenrvork Reduction Act of 1995, no ersons are reuired to respond to a collection of information unless it displa s a valid OMB control number
`
`L
`
`PATENT APPLICATION
`TRANSMITTAL
`(Only for new nonprovlsional applications under 37 CFR 1.53(b))
`
`Attomey Docket No.
`
`Firstlnventor
`
`Express Mail Label No.
`
`APPLICATION ELEMENTS
`See MPEP chapter 600 concerning utility patent application contents.
`
`'
`ADDRESS TO‘
`
`64507-5014-US
`
`BAKER. stenen J.
`BORON-CONTAINING SMALL ” I
`MOLECULES
`C")
`Ev553729231us
`Commissioner for Patents
`.
`.
`14
`P O Box
`50
`Alexandria VA 22313-1450
`
`:
`
`1. E Fee Transmittal Form (e.g., PTOISBI17)
`(Submit an original and a duplicate for fee processing)
`2. 8 Applicant claims small entity status.
`See 37 CFR127.
`111
`3. E Specification
`[Total Pages
`Both the claims and abstract must start on a new page
`(For information on the preferred arrangement, see MPEP 608. 01(a))
`4. IZDrawing(s) (35 U. S. 113)
`[Total Sheets
`12
`|
`
`ACCOMPANYING APPLICATION PARTS
`
`9. U Assignment Papers (cover sheet 8. document(s))
`
`Name of Assignee
`
`[Total SheetsLi 1o_ [1 37 cm 313(5) statement
`5. Doath or Declaration
`a. E] Newly executed (original or copy)
`(When there /5 3" 355i9"59)
`.
`.
`b. E] A copy from a prior application (37 CFR 1.63(d)
`.
`.
`(for continuation/divisional with Box 18 completed)
`11' D Enghsh Transmlon Document (If apphcame)
`i. U DELETION OF INVENTORIS)
`12. D information Disclosure Statement (PT0lSBl08 or PTO-1449)
`Signed statement attached deleting inventor(s) name
`C] Copies of citations attached
`in the prior application, see 37 CFR 1.63(d)(2) and
`1.33(b).
`6. EApplication Data Sheet. See 37 CFR 1.76
`
`E] Power of
`Attorney
`
`7. DCD-ROM or CD-R in duplicate, large table or
`Computer Program (Appendix)
`El Landscape Table on CD
`8. CI Nucleotide andlor Amino Acid Sequence Submission
`(if applicable, items a. — c. are required)
`a. C] Computer Readable Form CRF)
`b.
`Specification Sequence Listing on:
`
`i. CI CD-ROM or COR (2 copies); or
`ii.I'_‘l Paper
`Statements verifying identity of above copies
`
`13. D Preliminary Amendment
`14.
`IX] Return Receipt Postcard (MPEP 503)
`(Should be specifically itemized)
`
`15. El Certified Copy of Priority Document(s)
`(if foreign priority is claimed)
`16. El Nonpubllcatlon Request under 35 U.S.C. 122(b)(2)(B)(i)
`Applicant must attach form PTOISBI35 or equivalent.
`
`.
`
`17. D Omen
`
`18. [I if a CONTINUING APPLICATION, check appropriate box, and supply the requisite information below and in the first sentence of the specification following their title, or
`in an Application Sheet under 37'CFR 1.76:
`
`CI Continuation
`Prior application information:
`
`CI Divisional
`Examiner
`
`E] Continuation-in-part(C|P)
`
`Of Pfiof application N0. ................................... ..
`Art Unit:
`
`19. CORRESPONDENCE ADDRESS
`
`‘
`
`E The address associated with Customer Number.
`
`OR El Correspondence address below
`
`Ia
`
`Todd Esker
`
`Registration No.
`Attorne IA ent
`This ¢°”9¢1i°n 07 inlomlaiion is required DY 37 CFR 1-53(b). The inlonnation is required to obtain or retain a benefit by the public which is to file (and by the USPTO to process) an application. Confidentiality is
`governed by 35 USC. 122 and 37 CFR 1.11 and 1.14. This collection is estimated to take 12 minutes to complete, including gathering, preparing. and submitting the completed application form to the USPTO.
`Time will vary depending upon the individual case. Any comments on the amount oi time you require to complete this tonn andlor suggestions for reducing this burden, should be sent to the chiral information
`Olficer, US. Patent and Trademark Office, U.S. Department of Commerce, PO. Box 1450, Alexandria, VA 22313-1450. DO NOT SEND FEES OR COMPLETED FORMS TO THIS ADDRESS. SEND TO:
`Commissioner tor Patents. P.O. Box 1450, Alexandria. VA 22313-1450.
`1-SF/7343079.1
`
`t-
`
`7
`
`CFAD v. Anacor, IPR2015-01776, CFAD EXHIBIT 1070 - Page 3 of 558
`
`

`
`iiiiiiiiiiiiiiiiiiiiiiiiiiii
`
`PTOISB/17 (12-04)
`Approved for use through 07/31/2006. OMB 0651-0032
`US. Patent and Trademark Office; U.S. DEPARTMENT OF COMMERCE
`Underlhe Paenivork Reduction Act of 1995 no - -
`uired to res - nd to a collemion of inlormation unless it dis la s a valid OMB control number
`.
`Com . Iete if Known
`Effective on 12/08/2004.
`. Fees pursuant to the Consolidated Appropriations Act, 2005 (HR. 4818). A . “cation Number
`Not Yet Assi. ned
`FEE '|"RANS|V||TTA|_
`Filin Date
`Februa
`16,2006
`First Named Investor
`Baker, Stehen J.
`~oweiAssineu
`Not Yet Assi ned
`64507-5014-US
`
`For FY 2005
`A E A Iicant claims small enti
`status. See 37 CFR 1.27
`Total Amount of Pa ment
`($) 1100.00
`
`Art Unit
`Attorne Docket No.
`
`-
`
`METHOD OF PAYMENT (check all that apply)
`D Check E] Credit Card I:IMoney Order CI None D Other (plem identify):
`El Deposit Account Deposit Account Number 50-0310
`Deposit Account Name: Morgan, Lewis 8. Bockius LLP
`For the above-identified deposit account, the Director is hereby authorized to: (check all that apply)
`
`[I Charge fee(s) indicated below, except for the filing fee
`IE Charge fee(s) indicated below
`E Charge any additional fee(s) or underpayments of E Credit any overpayments
`fee(s) under 37 CFR 1.16 and 1.17
`WARNING: Information on this form may become public. Credit card information should not be included on this form. Provide credit card
`information and authorization on PTO-2038.
`FEE CALCULATION
`1. BASIC FILING, SEARCH. AND EXAMINATION FEES
`FILING FEES
`SEARCH FEES
`Small Entity
`Small Entig
`Fee (§1
`Fee (§)
`150
`250
`100
`50
`100
`150
`150
`250
`100
`0
`
`Agplication Type Fee (§)
`Utility
`300
`Design
`200
`Plant
`200
`Reissue
`300
`Provisional
`200
`
`Fee (5)
`500
`100
`300
`500
`0
`
`EXAMINATION FEES
`Small Entig
`Fee l§1
`100
`65
`80
`300
`0
`
`Fee ifl
`200
`130
`160
`600
`0
`
`2. EXCESS CLAIM FEES
`Fee Description
`Each claim over 20 or, for Reissues, each claim over 20 and more than in the original patent
`Each independent claim over 3 or. for Reissues, each independent claim more than in the original patent
`Multiple dependent claims
`Extra Claims
`Total Claims
`_39j - 20 or HP = _19j x
`HP = highest number of total claims paid for, if greater than 20
`lndeg. Claims
`Extra Claims
`x
`- 3 or HP =
`3
`HP = highest number of total claims paid for, if greater than 3
`3. APPLICATION SIZE FEE
`If the specification and drawings exceed 100 sheets of paper, the application size fee due is $250 ($125 for small entity) for each
`additional 50 sheets or fraction thereof. See 35 U.S.C. 41(a)(1)(G) and 37 CFR 1.16(s).
`Total Sheets
`Extra Sheets
`Number of each additional 50 or fraction thereof Fee(§)
`123
`23
`/ 50 =
`(round up to a whole number)
`x
`
`- 100 =
`
`Fee Paid Q)
`125
`
`4. OTHER FEE(S)
`Non-English Specification, $130 fee (no small entity discount)
`Other:
`
`Fees Paid (§[
`
`/"
`
`Registration No. 46,690
`’
` Amme /A em
`?
`Todd Esker
`
`Telephone (415) 442-1304
`Date February 16, 2006
`This collection of intonnation is required by 37 CFR 1.136, The intonnation is required to obtain or retain a benefit by the public which is to file (and by
`the USPTO to process) an application. Confidentiality is governed by 35 U.S.C. 122 and 37 CFR 114. This collection is estimated to take 30 minutes
`to complete. including gathering. preparing. and submitting the completed application form to the USPTO. Time will vary depending upon the individual
`case, Any comments on the amount of time you require to complete this form andlor suggestions for reducing this burden, should be sent to the Chief
`information Oificer, US. Patent and Trademark Office, U.S. Department of Commerce, PO. Box 1450, Alexandria, VA 22313-1450. DO NOT SEND
`FEES OR COMPLETED FORMS TO THIS ADDRESS. SEND TO: Commissioner for Patents, P.O. Box 1450, Alexandria, VA 22313-1450.
`Ifyou need assistance in completing the fonn, call 1-800-PTO-9199 and select option 2.
`
`SUBMITTED BY
`
`Name (Print/Type)
`
`1-SFI73430B7.1
`
`Small Entity
`Fee 1§)
`Fee ($1
`25
`50
`100
`200
`180
`360
`Multigle Degendent Claims
`Fee ($1)
`Fee Paid ($1)
`
`Fee (§)
`25
`
`Fee (§)
`
`Fee Paid (5)
`475___
`
`Fee Paid Q)
`
`CFAD v. Anacor, IPR2015-01776, CFAD EXHIBIT 1070 - Page 4 of 558
`
`

`
`Attorney Docket No.: 064507-5014 US
`
`PATENT APPLICATION
`
`BORON—CONTAINING SMALL MOLECULES
`
`Inventor(s):
`
`Stephen J. Baker, a citizen of the United Kingdom, residing at
`1568 Begen Avenue, Mountain View, CA 94040
`
`Tsutomu Akama, a citizen of Japan, residing at
`832 Azure St, Sunnyvale, CA 94087
`
`Carolyn Bellinger-Kawahara, a citizen of the USA, residing at
`15 Landa Lane, Redwood City, CA 94061
`
`Vincent S. Hernandez, a citizen of the USA, residing at
`287 Gilchrist Ln, Watsonville, CA 95076
`
`Karin M. Hold, a citizen of the USA, residing at
`1908 Valdez Ave, Belmont, CA 94002
`
`James J Leyden, a citizen of the USA, residing at
`319 Applebrook Drive, Malvem, PA 19355
`
`Kirk Maples, a citizen of the USA, residing at
`1195 San Moritz Drive, San Jose, CA 95132
`
`Jacob Plattner, a citizen of the USA, residing at
`1016 Amito Ave., Berkeley, CA 94705
`
`Virginia Sanders, a citizen of the USA, residing at
`2895 Harrison St, Apt 4, San Francisco, CA 941 10
`
`Yong—Kang Zhang, a citizen of the United States, residing at
`5151 Westmont Avenue, San Jose, CA 95130
`
`Assignee:
`
`Anacor Pharmaceuticals
`1060 East Meadow Circle
`
`Palo Alto, CA 94303-4230
`
`Entity:
`
`Small
`
`Todd Esker
`Reg. No. 46,690
`
`MORGAN
`LEWIS AND
`
`BOCKIUS
`LLP
`
`Correspondence
`Address:
`
`One Market
`Spear Street Tower
`San Francisco
`California 94105
`Tel 415 442-1000
`Fax 415 442-1001
`
`~
`
`AS FILED WITH THE USPTO ON FEBRUARY 16, 2006
`
`CFAD v. Anacor, IPR2015-01776, CFAD EXHIBIT 1070 - Page 5 of 558
`
`

`
`Attorney Docket No.: 064507-50l4US
`
`PATENT
`
`BORON-CONTAINING SMALL MOLECULES
`
`CROSS-REFERENCE TO RELATED APPLICATIONS
`
`[0001] ' The present application is related to U.S. Provisional Patent Application
`
`60/654,060 filed February 16, 2005, which is incorporated by reference in its entirety
`
`for all purposes.
`
`BACKGROUND FOR THE INVENTION
`
`[0002]
`
`Infections of the nail and hoof, known as ungual and/or periungual
`
`infections, pose serious problems in dermatology. These ungual and/or periungual
`
`can be caused by sources such as fungi, viruses, yeast, bacteria and parasites.
`
`Onychomycosis is an example of these serious ungual and/or periungual infections
`
`and is caused by at least one fungus. Current treatment for ungual and/or periungual
`
`infections generally falls into three categories: systemic administration of medicine;
`
`surgical removal of all or part of the nail or hoof followed by topical treatment of the
`
`exposed tissue; or topical application of conventional creams, lotions, gels or
`
`solutions, frequently including the use of bandages to keep these dosage forms in
`
`place on the nail or hoof. All of these approaches have major drawbacks. The
`
`following discussion is particularly directed to drawbacks associated with current
`
`treatment of ungual and/or periungual antifungal infections.
`
`[0003]
`
`Long term systemic (oral) administration of an antifungal agent for the
`
`treatment of onychomycosis is often required to produce a therapeutic effect in the
`
`nail bed. For example, oral treatment with the antifungal compound ketoconozole
`
`typically requires administration of 200 to 400 mg/day for 6 months before any
`
`significant therapeutic benefit is realized. Such long term, high dose systemic therapy
`
`can have significant adverse effects. For example, ketoconozole has been reported to
`
`have liver toxicity effects and reduces testosterone levels in blood due to adverse
`
`effects on the testes. Patient compliance is a problem with such long term therapies
`
`especially those which involve serious adverse effects. Moreover, this type of long
`
`term oral therapy is inconvenient in the treatment of a horse or other ruminants
`
`afflicted with fungal infections of the hoof. Accordingly, the risks associated with
`
`CFAD v. Anacor, IPR2015-01776, CFAD EXHIBIT 1070 - Page 6 of 558
`
`

`
`parenteral treatments generate significant disincentive against their use and
`
`considerable patient non-compliance.
`
`[0004]
`
`Surgical removal of all or part of the nail followed by topical treatment
`
`also has severe drawbacks. The pain and discomfort associated with the surgery and
`
`the undesirable cosmetic appearance of the nail or nail bed represent significant
`
`problems, particularly for female patients or those more sensitive to physical
`
`appearance. Generally, this type of treatment is not realistic for ruminants such as
`
`horses.
`
`[0005]
`
`Topical therapy has significant problems too. Topical dosage forms such
`
`as creams, lotions, gels etc., can not keep the drug in intimate contact with the
`
`infected area for therapeutically effective periods of time. Bandages have been used
`
`to hold drug reservoirs in place in an attempt to enhance absorption of the
`
`pharmaceutical agent. However the bandages are thick, awkward, troublesome and
`
`generally lead to poor patient compliance.
`
`[0006]
`
`Hydrophilic and hydrophobic film forming topical antiftmgal solutions
`
`have also been developed. These dosage forms provide improved contact between the
`
`drug and the nail, but the films are not occlusive. Topical formulations for fungal
`
`infection treatment have largely tried to deliver the drug to the target site (an infected
`
`nail bed) by diffusion across or through the nail.
`
`[0007]
`
`Nail is more like hair than stratum comeum with respect to chemical
`
`composition and permeability. Nitrogen is the major component of the nail attesting
`
`to the nail's proteinaceous nature. The total lipid content of mature nail is 0.1-1.0%,
`
`while the stratum comeum lipid is about 10% w/w. The nail is 100-200 times thicker
`
`than the stratum comeum and has a very high affinity and capacity for binding and
`
`retaining antifungal drugs. Consequently little if any drug penetrates through the nail
`
`to reach the target site. Because of these reasons topical therapy for fungal infections
`
`have generally been ineffective.
`
`[0008]
`
`Compounds known as penetration or permeation enhancers are well
`
`known in the art to produce an increase in the permeability of skin or other body
`
`membranes to a pharmacologically active agent. The increased permeability allows an
`
`increase in the rate at which the drug permeates through the skin and enters the blood
`
`stream. Penetration enhancers have been successful in overcoming the
`
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`

`
`impermeability of pharmaceutical agents through the skin. However, the thin stratum
`
`comeum layer of the skin, which is about 10 to 15 cells thick and is formed naturally
`
`by cells migrating toward the skin surface from the basal layer, has been easier to
`
`penetrate than nails. Moreover, known penetration enhancers have not proven to be
`
`useful in facilitating drug migration through the nail tissue.
`
`[0009]
`
`Antimicrobial compositions for controlling bacterial and fungal infections
`
`comprising a metal chelate of 8-hydroxyquinoline and an alkyl benzene sulfonic acid
`
`have been shown to be efficacious due to the increased ability of the oleophilic group
`
`to penetrate the lipoid layers of micro-cells. The compounds however, do not
`
`effectively increase the ability to carry the pharmaceutically active antifungal through
`
`the comified layer or stratum comeum of the skin. U.S. Pat. No. 4,602,011, West et
`
`al., Jul. 22, 1986; U.S. Pat. No. 4,766,113, West et al., Aug. 23, 1988.
`
`[0010]
`
`Therefore, there is a need in the art for compounds which can effectively
`
`penetrate the nail. There is also need in the art for compounds which can effectively
`
`treat ungual and/or periungual infections. These and other needs are addressed by the
`
`current invention.
`
`SUMMARY OF THE INVENTION
`
`[0011]
`
`In a first aspect, the invention provides a compound having a structure
`
`according to Formula 1:
`
`wherein B is boron. R” is a member selected from a negative charge, a salt
`
`counterion, H, substituted or unsubstituted alkyl, substituted or unsubstituted
`
`heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted
`
`heterocycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted
`
`heteroaryl. M1 is a member selected from oxygen, sulfur and NR2“. R2“ is a member
`
`selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted
`
`heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted
`
`CFAD v. Anacor, IPR2015-01776, CFAD EXHIBIT 1070 - Page 8 of 558
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`

`
`heterocycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted
`
`heteroaryl. J 1 is a member selected from (CR3aR4a),,1 and CR5“. R33, R43, and R5“ are
`
`members independently selected from H, OH, NH2, SH, substituted or unsubstituted
`
`alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl,
`
`substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, and
`
`substituted or unsubstituted heteroaryl. The index n1 is an integer selected from O to
`
`2. W1 is a member selected from C=O (carbonyl), (CR6aR7")m1 and CR“. R6“, R7‘‘,
`
`and R8‘’ are members independently selected from H, OH, NH2, SH, substituted or
`
`unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or
`
`unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or
`
`unsubstituted aryl, and substituted or unsubstituted heteroaryl. The index ml is an
`
`integer selected from 0 and 1. A1 is a member selected from CR9“ and N. D1 is a
`
`member selected from CR’°" and N. E1 is a member selected from CR1” and N. G1
`
`is a member selected from CR'2“ and N. R9“, R10“, R‘ 1“ and R12“ are members
`
`independently selected from H, OH, NH2, SH, substituted or unsubstituted alkyl,
`
`substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl,
`
`substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, and
`
`substituted or unsubstituted heteroaryl. The combination of nitrogens (A1 + D1 + E1
`
`+ G1) is an integer selected from O to 3. A member selected from R”, R4“ and R5“
`
`and a member selected from R6”, R7” and Rsa, together with the atoms to which they
`
`are attached, are optionally joined to form a 4 to 7 membered ring. R33 and R4“,
`
`together with the atoms to which they are attached, are optionally joined to form a 4
`
`to 7 membered ring. R6“ and R7“, together with the atoms to which they are attached,
`
`are optionally joined to form a 4 to 7 membered ring. R93 and R10“, together with the
`
`atoms to which they are attached, are optionally joined to form a 4 to 7 membered
`
`ring. R103 and R1”, together with the atoms to which they are attached, are optionally
`
`joined to form a 4 to 7 membered ring. R1” and RH“, together with the atoms to
`
`which they are attached, are optionally joined to form a 4 to 7 membered ring. The
`
`aspect has the proviso that when M1 is oxygen, W1 is a member selected from
`
`(CR3aR4a)nl, wherein n1 is 0, J1 is a member selected from (CR6“R7a),,,1, wherein ml is
`
`1, A1 is CR9“, D1 is cR‘°*‘, E1 is CR1”, G1 is cR”“, then R9“ is not halogen, methyl,
`
`ethyl, or optionally joined with Rm“ to a form phenyl ring; R103 is not unsubstituted
`
`phenoxy, C(CH3)3, halogen, CF3, methoxy, ethoxy, or optionally joined with R9“ to
`
`form a phenyl ring; R1 1“ is not halogen or optionally joined with Rm“ to form a phenyl
`
`CFAD v. Anacor, IPR2015-01776, CFAD EXHIBIT 1070 - Page 9 of 558
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`

`
`ring; and R12“ is not halogen. The aspect has the further proviso that when M1 is
`
`oxygen, W1 is a member selected from (CR3aR4a)n1, wherein n1 is 0, J 1 is a member
`
`selected from (CR'5“R7“‘)m1, wherein ml is 1, A1 is CR9“, D1 is CR‘°"‘, E1 is cR““, G1
`
`is CRH“, then neither R6“ nor R7“ are halophenyl. The aspect has the further proviso
`
`that when M1 is oxygen, W1 is a member selected from (CR3aR4a "1, wherein n1 is 0,
`
`J 1 is a member selected from (CR6“R7")m1, wherein ml is 1, A1 is CR9“, D1 is CR'°“,
`
`E1 is CR'“‘, G1 is cR‘2“, and R9‘: Rm“ and R““ are H, then R6“, R7“ and Rm are not
`
`H. The aspect has the further proviso that when M] is oxygen wherein n1 is 1, J1 is a
`
`member selected from (cR°*‘R7*'),,,., wherein ml is 0, A1 is CR9“, D1 is CR'°", E1 is
`CR“, G1 is cR”“, R9“ is H, R‘°"‘ is H, R1” is H, R6” is H, R“ is H, R12“ is H, then w1
`
`is not C=O (carbonyl). The aspect has the further proviso that when M1 is oxygen,
`
`W1 is CR5“, J1 is CR3“, A1 is CR9“, D1 is cR‘°‘*, E1 is cR“a, G1 is cR"“, R5“, R7“,
`
`R9“, R10“, R1 1“ and Rm are H, then R5“ and R8“, together with the atoms to which they
`
`are attached, do not form a phenyl ring.
`
`[0012]
`
`In a second aspect, the invention provides a pharmaceutical formulation
`
`comprising (a) a pharmaceutically acceptable excipient; and (b) a compound having a
`
`structure according to Formula 11:
`
`wherein B is boron. R“’ is a member selected from a negative charge, a salt
`
`counterion, H, substituted or unsubstituted alkyl, substituted or unsubstituted
`
`heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted
`
`heterocycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted
`
`heteroaryl. M2 is a member selected from oxygen, sulfur and NR2”. R2” is a member
`
`selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted
`
`heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted
`
`heterocycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted
`
`heteroaryl. J2 is a member selected from (CR3bR4b),,2 and CR5”. R3b, RM’, and Rsb are
`
`members independently selected from H, OH, NH2, SH, substituted or unsubstituted
`
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`

`
`alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl,
`
`substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, and
`
`substituted or unsubstituted heteroaryl. The index n2 is an integer selected from O to
`
`2. W2 is a member selected from c=o (carbonyl), (CR6”R”’)m2 and CR8’. R6’, R7”,
`
`and R3’ are members independently selected from H, OH, NH;_, SH, substituted or
`
`unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or
`
`unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or
`
`unsubstituted aryl, and substituted or unsubstituted heteroaryl. The index m2 is an
`
`integer selected from 0 and 1. A2 is a member selected from CR9’ and N. D2 is a
`
`member selected from CR’°” and N. E2 is a member selected from CR’ ”’ and N. G2
`
`is a member selected from CR’’‘’’ and N. R9”, R10’, Rm’ and RD" are members
`
`independently selected from H, OH, NH2, SH, substituted or unsubstituted alkyl,
`
`substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl,
`
`substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, and
`
`substituted or unsubstituted heteroaryl. The combination of nitrogens (A2 + D2 + E2
`
`+ G2) is an integer selected from O to 3. A member selected from R3’, R4’ and R5’
`
`and a member selected from R6’, R7” and R8’, together with the atoms to which they
`
`are attached, are optionally joined to form a 4 to 7 membered ring. R3’ and R4’,
`
`together with the atoms to which they are attached, are optionally joined to form a 4
`
`to 7 membered ring. R6’ and R7”, together with the atoms to which they are attached,
`
`are optionallyjoined to form a 4 to 7 membered ring. R9’ and R10’, together with the
`
`atoms to which they are attached, are optionally joined to form a 4 to 7 membered
`
`ring. Rm” and R’ ”’, together with the atoms to which they are attached, are optionally
`
`joined to form a 4 to 7 membered ring. R’ ”’ and R12’, together with the atoms to
`
`which they are attached, are optionally joined to form a 4 to 7 membered ring.
`
`[0013]
`
`In another aspect, the invention provides a method of killing a
`
`microorganism, comprising contacting the microorganism with a therpeutically
`
`effective amount of a compound of the invention.
`
`[0014]
`
`In another aspect, the invention provides a method of inhibiting
`
`microorganism growth, comprising contacting the microorganism with a
`
`therpeutically effective amount of a compound of the invention.
`
`CFAD v. Anacor, IPR2015-01776, CFAD EXHIBIT 1070 - Page 11 of 558
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`

`
`[0015]
`
`In another aspect, the invention provides a method of treating an infection
`
`in an animal, comprising administering to the animal a therpeutically effective amount
`
`of a compound of the invention.
`
`[0016]
`
`In another aspect, the invention provides a method of preventing an
`
`infection in an animal, comprising administering to the animal a therpeutically
`
`effective amount of a compound of the invention.
`
`[0017]
`
`In another aspect, the invention provides a method of treating