PATENT
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`IN THE UNITED STATES PATENT AND TRADEMARK OFFICE
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`Applicants
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`Application No.
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`Filed
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`For
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`Sung Hwan Moon et a1.
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`12/553,858
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`September 3, 2009
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`REVERSE—TURN MIMETICS AND METHOD RELATING
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`THERETO
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`Examiner
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`Art Unit
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`Docket No.
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`Date
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`Kahsay Habte
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`1624
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`200146.402C9
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`November 16, 2010
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`Mail Stop Amendment
`Commissioner for Patents
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`PO. Box 1450
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`Alexandria, VA 22313—1450
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`Commissioner for Patents:
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`AMENDMENT
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`In response to the Office Action dated September 9, 2010, please amend the
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`above—identified application as follows:
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`Amendments to the Claims are reflected in the listing of claims which begins on
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`page 2 of this paper.
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`Amendments to the Abstract begin on page 14 of this paper.
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`Remarks begin on page 15 of this paper.
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`
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`
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`IN THE UNITED STATES PATENT AND TRADEMARK OFFICE
`
`Applicants
`
`Application No.
`
`Filed
`
`For
`
`:
`
`:
`
`:
`
`:
`
`Sung Hwan Moon et a1.
`
`12/553,858
`
`September 3, 2009
`
`REVERSE—TURN MIMETICS AND METHOD RELATING
`
`THERETO
`
`Examiner
`
`Art Unit
`
`Docket No.
`
`Date
`
`:
`
`:
`
`:
`
`:
`
`Kahsay Habte
`
`1624
`
`200146.402C9
`
`November 16, 2010
`
`Mail Stop Amendment
`Commissioner for Patents
`
`PO. Box 1450
`
`Alexandria, VA 22313—1450
`
`Commissioner for Patents:
`
`AMENDMENT
`
`In response to the Office Action dated September 9, 2010, please amend the
`
`above—identified application as follows:
`
`Amendments to the Claims are reflected in the listing of claims which begins on
`
`page 2 of this paper.
`
`Amendments to the Abstract begin on page 14 of this paper.
`
`Remarks begin on page 15 of this paper.
`
`
`
`
`
`Application No. 12/553,858
`Response to Office Action dated September 9, 2010
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`Amendments to the Claims:
`
`This listing of claims will replace all prior versions, and listings, of claims in the
`
`application:
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`Listing of Claims:
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`1. — 42.
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`(Canceled)
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`43.
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`(Previously Presented) A compound of formula (VI):
`
`N
`
`0
`
`as an isolated stereoisomer or a mixture of stereoisomers or as a pharrnaceutically
`
`*3
`
`(VI)
`
`acceptable salt, wherein,
`
`Ra is a bicyclic aryl group having 8 to 11 ring members, which may have 1 to 3
`
`heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur;
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`Rb is a monocyclic aryl group having 5 to 7 ring members, which may have 1 to 2
`
`heteroatoms selected from nitrogen, oxygen or sulfur, and aryl ring in the compound may have
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`one or more substituents selected from a group consisting of halide, hydroxy, cyano, lower alkyl,
`
`and lower alkoxy groups;
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`Rc is a saturated or unsaturated C1_6alkyl, C1_6alkoxy, perfluoro C1_6alkyl group;
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`and
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`X1, X2, and X3 may be the same or different and independently selected from
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`hydrogen, hydroxyl, and halide.
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`
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`Application No. 12/553,858
`Response to Office Action dated September 9, 2010
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`44.
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`(Previously Presented) The compound of claim 43, wherein the bicyclic
`
`aryl group is not substituted.
`
`45.
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`(Previously Presented) The compound of claim 43, wherein the bicyclic
`
`aryl group is substituted.
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`46.
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`(Previously Presented) The compound of claim 45, wherein the bicyclic
`
`aryl group is substituted indazolyl.
`
`47.
`
`(Currently Amended) The compound of claim 46 selected from the group
`
`consisting of:
`
`
`
`
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`Application No. 12/553,858
`Response to Office Action dated September 9, 2010
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`Application No. 12/553,858
`Response to Office Action dated September 9, 2010
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`Application No. 12/553,858
`Response to Office Action dated September 9, 2010
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`Application No. 12/553,858
`Response to Office Action dated September 9, 2010
`
`
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`48.
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`(Previously Presented) The compound of claim 45, wherein the bicyclic
`
`aryl group is substituted quinolinyl.
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`49.
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`(Currently Amended) The compound of claim 48 selected from the group
`
`consisting of:
`
`
`
`
`Y
`
`a
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`N W
`
`e
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`HC
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`
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`Application No. 12/553,858
`Response to Office Action dated September 9, 2010
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`50.
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`(Previously Presented) The compound of claim 45, wherein the bicyclic
`
`aryl group is substituted 3,4-dihydrobenzo[l,4]oxazinyl.
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`51.
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`(Currently Amended) The compound of claim 50 selected from the group
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`consisting of:
`
`N
`
`0
`
`Ha
`
`N
`
`HZC
`
`\
`
`EN
`
`0
`
`Y
`N
`
`H3C\N
`
`fl
`o
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`°
`HCMTF;N
`01?)
`Wwe ; wow;
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`Application No. 12/553,858
`Response to Office Action dated September 9, 2010
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`. $0 . “zcwngCEZJ
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`52.
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`(Previously Presented) The compound of claim 45, wherein the bicyclic
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`aryl group is substituted naphthyl.
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`53.
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`(Currently Amended) The compound of claim 52 being
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`
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`54.
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`(Previously Presented) The compound of claim 45, wherein the bicyclic
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`aryl group is substituted benzotriazolyl.
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`55.
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`(Currently Amended) The compound of claim 54 selected from the group
`
`consisting of:
`
`
`
`
`
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`Application No. 12/553,858
`Response to Office Action dated September 9, 2010
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`
`
`Hf'K/ko
`OOH
`
`_
`
`é
`
`OH
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`56.
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`(Previously Presented) A pharmaceutical composition comprising a
`
`compound according to claim 43 and a phannaceutically acceptable carrier.
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`57.
`
`(Previously Presented) The pharmaceutical composition of claim 56,
`
`wherein the bicyclic aryl group is not substituted.
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`58.
`
`(Previously Presented) The pharmaceutical composition of claim 56,
`
`wherein the bicyclic aryl group is substituted.
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`59.
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`(Currently Amended) A compound 0fe£—formu1a(VII):
`
`10
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`
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`Application No. 12/553,858
`Response to Office Action dated September 9, 2010
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`as an isolated stereoisomer or a mixture of stereoisomers or as a pharmaceutically
`
`(VII)
`
`acceptable salt, wherein:
`
`Ra is a phenyl group, a substituted phenyl group having one or more substituents
`
`wherein the one or more substituents are independently selected from one or more of amino,
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`amidino,
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`guanidino, hydrazino,
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`amidazonyl, C1_4alkylamino, C1_4dialkylamino, halogen,
`
`perfluoro C1_4alkyl, C1_4alkyl, C1-3alkoxy, nitro, carboxy, cyano, sulfuryl, and hydroxyl groups, or
`
`a bicyclic aryl group having 8 to 11 ring members, which may have 1 to 3 heteroatoms selected
`
`from the group consisting of nitrogen, oxygen and sulfur;
`
`Rb is a monocyclic aryl group having 5 to 7 ring members, which may have 1 to 2
`
`heteroatoms selected from nitrogen, oxygen or sulfur, and aryl ring in the compound may have
`
`one or more substituents selected from a group consisting of halide, hydroxy, cyano, lower alkyl,
`
`and lower alkoxy groups;
`
`Rc is a saturated or unsaturated C1-6alkyl, C1_6alkoxy, perfluoro C1_6alkyl group;
`
`and
`
`Rd IS-G%alkyl£flalkyl.
`
`60.
`
`(Previously Presented) The compound of claim 59, wherein the bicyclic
`
`aryl group is not substituted.
`
`61.
`
`(Previously Presented) The compound of claim 59, wherein the bicyclic
`
`aryl group is substituted.
`
`ll
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`Application No. 12/553,858
`Response to Office Action dated September 9, 2010
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`62.
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`(Previously Presented) The compound of claim 59, wherein Rd is methyl.
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`63.
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`(Currently Amended) The compound of claim 62 selected from the group
`
`consisting of:
`
`
`
`12
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`Application No. 12/553,858
`Response to Office Action dated September 9, 2010
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`64.
`
`(Previously Presented) A pharmaceutical composition comprising a
`
`compound according to claim 59 and a pharmaceutically acceptable carrier.
`
`65.
`
`(Previously Presented) The pharmaceutical composition of claim 64,
`
`wherein the bicyclic aryl group is not substituted.
`
`66.
`
`(Previously Presented) The pharmaceutical composition of claim 64,
`
`wherein the bicyclic aryl group is substituted.
`
`13
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`
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`Application No. 12/553,858
`Response to Office Action dated September 9, 2010
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`Amendments to the Abstract:
`
`Please replace the previous Abstract with the following redlined Abstract:
`
`Conformationally constrained compounds that mimic the secondary structure of
`
`reverse-tum regions of biologically active peptides and proteins are disclosed. Such reverse—tum
`
`mimetic structures have utility ever—Héée—pange—eéfieldsrineluéing—Hse—as diagnostic and
`
`therapeuticagents.
`
`=.
`
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`
`-
`
`.
`
`.
`
`~
`
`=
`
`-
`
`=
`
`
`
`
`
`modulated by Wnt-signaling pathway, such as cancer, especially colorectal cancer, restenosis
`
`associated with angioplasty, polycystic kidney disease, aberrant angiogenesis disease, rheumatoid
`
`arthritis disease, tuberous sclerosis complex, Alzheimer’s disease, excess hair growth or loss, or
`
`ulcerative colitis.
`
`formula VI :
`
`
`
`
`
`these reverse-term mimetics have aIn one embodiment eneral structure of
`
`
`
`
`wherein RQEDLRQALLX; and X; are defined as provided herein.
`
`l4
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`
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`Application No. 12/553,858
`Response to Office Action dated September 9, 2010
`
`REMARKS
`
`Reconsideration of the present application in View of the above amendments and
`
`the following remarks is respectfully requested. Claims 43-65 are pending.
`
`Claim Amendments
`
`By way of this Amendment, Assignee1 has amended claims 47, 49, 51, 53, 55, 59
`
`and 63.
`
`Claims 47, 49, 51, 53, 55 and 63 have been amended to correct informalities of
`
`the chemical structures recited in these claims by depicting hydrogen on the nitrogen atom.
`
`Claim 59 has been amended to recite Rd as C1_7 alkyl (rather than C1_6 alkyl) and to
`
`correct typographical errors. Support for this amendment may be found in the definition of lower
`
`chain alkyl moieties at page 18, lines 18-23 of the present application.
`
`No new matter has been added Via the amendments to the claims.
`
`Objection to Abstract
`
`The abstract stands objected to as not containing the proper content, and the
`
`Examiner has recommended that it be amended to include a chemical structure of formula (VI)
`
`and the use of the compounds. Assignee has amended the abstract as recommended.
`
`Accordingly, Assignee respectfully requests that this objection be withdrawn.
`
`Double Patenting Rejections
`
`Claims 43-66 stand rejected on the ground of nonstatutory obviousness-type
`
`double patenting as unpatentable over (1) claims 1—6 of US. Patent No. 7,232,822, (2) claims 1—
`
`10 of US Patent No. 7,671,054, (3) claims 1—3 of US. Patent No. 7,566,711, and (4) claims 1-3
`
`ofU.S. Patent No. 7,576,084.
`
`1 Assignee is the party responding to the Office Action with evidence of ownership recorded in USAN 10/803,179
`with the US Patent Office at Reel 015053, Frame 0046 on August 5, 2004. The ‘179 application is the grandparent
`application of the present application and has the same specification as the present application.
`
`15
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`
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`Application No. 12/553,858
`Response to Office Action dated September 9, 2010
`
`To facilitate allowance and without acquiescing to the rejections, Assignee
`
`submits a terminal disclaimer to obviate these rejections. Accordingly, Assignee respectfully
`
`requests that these rejections be Withdrawn.
`
`Related Applications
`
`In addition to the applications identified in the Information Disclosure Statement
`
`Transmittal (IDS) dated February 19, 2010, Assignee wishes to bring to the Examiner’s attention
`
`the following related applications and patents :
`
`USAN 09/976,470 (abandoned)
`
`USAN 10/087,443 (abandoned)
`
`USAN 10/411,877 (abandoned)
`
`USAN 11/242,653 (issued as Patent No. 7,585,862)
`
`USAN 12/756,095 (pending)
`
`USAN 11/377,898 (issued as Patent No. 7,563,825)
`
`USAN 12/616,712 (pending)
`
`USAN 11/605,202 (pending)
`
`USAN 12/759,854 (pending)
`
`USAN 12/738,066 (pending)
`
`For the Examiner’s convenience, a copy of the currently pending or issued claims of the above—
`
`listed applications and patents are submitted herewith.
`
`In addition, Assignee further encloses the pending claims of USAN 12/541,388
`
`and USAN 12/510,107, as well as the issued claims of US. Patent No. 7,531,320. These cases
`
`were previously identified in the IDS dated February 19, 2010, and Assignee wishes to ensure
`
`that the Examiner has fully considered the same in the course of prosecution of this application.
`
`Prosecution of Related Application
`
`USAN 12/541,388 (“the 388 application”) relates to the present application in that
`
`it claims prodrugs of compounds that are the same as or similar to the compounds of claims 59-
`
`63 of the present application. During prosecution of the ‘3 88 application, Assignee received an
`
`16
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`
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`Application No. 12/553,858
`Response to Office Action dated September 9, 2010
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`unsolicited Declaration from Dr. Michael Kahn, a co-inventor of the ‘388 application (and the
`
`present application), asserting that the claims of the ‘388 application are not patentable for failing
`
`to meet
`
`the enablement and written description requirements. Assignee submitted the
`
`Declaration (including W02009/148192 referenced therein)
`
`to Examiner Venkataraman
`
`Balasubramanian in the ‘3 88 application on September 30, 2010. To ensure compliance with
`
`Assignee’s duty of candor and good faith in dealing with the US. Patent Office, a copy of this
`
`Declaration is submitted herewith in a Supplemental Information Disclosure Statement, along
`
`with the Amendment filed by the Assignee in the ‘388 application addressing the same.
`
`Conclusion
`
`In View of the above amendments and remarks, Assignee submits that the claims
`
`in the present application are now allowable. Favorable consideration and a Notice of Allowance
`
`are earnestly solicited.
`
`The Director is authorized to charge any additional fees due by way of this
`
`Amendment, or credit any overpayment, to our Deposit Account No. 19-1090.
`
`Respectfully submitted,
`
`SEED Intellectual Property Law Group PLLC
`
`m—
`Qing Lin, Ph.D.
`Registration No. 53,937
`
`Enclosures:
`
`Terminal Disclaimer
`
`Pending Claims ofUSAN’s 12/756,095; 12/616,712; 11/605,202; 12/759,854;
`12/738,066; 12/541,388 and 12/510,107
`Issued Claims ofU.S. Patent Nos. 7,585,862; 7,563,825 and 7,531,320
`Supplemental Information Disclosure Statement
`
`QXL/cew
`
`701 Fifth Avenue, Suite 5400
`
`Seattle, Washington 98104
`Phone: (206) 622—4900
`Fax:
`(206) 682-6031
`1735093_1.DOCX
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`l7
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