IN THE UNITED STATES PATENT AND TRADEMARK OFFICE
`
`In re Application of
`
`AUSTIN ET AL
`
`serial No.
`
`08/750,081
`
`Filed: December 9, 1996
`
`\ For:
`\
`
`Group Art
`
`Examiner:
`
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`
`(\ .-. "F.".
`
`I'e,
`
`AMENDMENT
`
`Honorable Commissioner of
`Patents and-Trademarks
`.Washington, D.C. 20231
`
`iSir:
`
`July 7, 1998
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`In response to the Office Action dated April 7, 1998, please amend
`
`the above application as follows:
`
`" ,", c~'"',L , (/nLL,.
`
`1.
`
`(Amended) A method for the protection of a medium susceptible to microbial
`treatment of the medium with an effective amount of an oxaborole of
`
`attack by the
`\~ formula (1)
`
`(.
`
`or a salt thereof:
`wherein
`
`A~X"
`I 0
`o Bf
`I
`OR
`
`(1 )
`
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`

`
`AUSTIN ET AL
`Serial No. 08/750,081
`
`A and D together with the carbon atoms to which they are attached form a 5, 6, or
`7 -membered fused ring which may be substituted by C"6-alkyl, C,.6-alkoxy, hydroxy,
`halogen, nitro, nitrile, amino, amino substituted by one or more C,..-alkyl groups,
`[(optionally substituted by one or more C,.s-alkyl groups)], carboxy, acyl, aryloxy,
`carbonamido, carbonamido substituted by C'.6-alkyl [carbonomido (optionally substituted
`by C'.6-alkyl)], sulphonamido or trifluoromethyl or the fused ring may link two oxaborole
`rings;
`
`X is a group -CR'R' wherein R' and R' are each, independently, hydrogen,
`C,..-alkyl, nitrile, nitro, aryl, aralkyl or R' and R2 together with the carbon atom to which
`they are attached form an alicyclic ring; and
`R is hydrogen, C"'8-alkyl, ([optionally] C"'8-alkyl substituted by C'.6-alkoxy,
`C'.6-alkylthio, hydroxy, amino, amino substituted by C"'8-alkyl, [(optionally substituted by
`C"'8-alkyl)], carboxy, aryl, aryloxy, carbon ami do, ([optionally substituted by C,.6-alkyl, aryl
`or aralkyl] carbonamido substituted by C'.6-alkyl. aryl or aralkyl), aralkyl, aryl, heteroaryl,
`substituted by phenYl, C,.6-alkoxy,
`[(optionally
`cycloalkyl, C"'8-alkyleneamino,
`C'.6-alkylthio)] C,.,,-alkyleneamino substituted by phenyl, C,.6-alkoxy or C"6-alkylthio,
`carbonyl alkyleneamino or a radical of formula (2)
`
`'
`
`/
`
`~x'
`/',-
`
`A~X~ I 0
`D B/
`I
`wherein A, D and X are as defined hereinbefore except for boronophthalide,
`
`(2)
`
`i
`
`, '
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`!
`
`(Amended) A method as claimed in either claim 1 or claim 2 wherein [the
`3.
`sUbstituent in] the fused ring [is halogen] is substituted by halogen.
`
`(Amended) A method as claimed in claim 1 wherein the heteroaryl substituent
`5,
`represented by R is quinolinyl.
`
`6.
`
`(Amended) A method as claimed in claim 1 wherein the oxaborole is a compound
`
`J
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`.\'''' ____ :f formula 3
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`(3)
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`3
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`4
`R
`
`A~X~
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`I 0
`
`- /
`D """B,)_N+R
`
`r-p
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`' - y
`
`./
`
`'-'
`
`5/
`
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`
`AUSTIN ET AL
`Serial No. 08/750,081
`
`wherein
`A. D and X are as defined in claim 1;
`Y is a divalent alkylene linking group containing up to 18 carbon atoms [optionally]
`or a divalent alkylene linking group containing up to 18 carbon atoms which is substituted
`by phenyl, C,.6alkoxy, C,.6-alkylthio; carbonyl alkylene amino; [or] and
`R3 and R4 are each, independently, hydrogen, C"1B-alkyl or phenyl or R3 together
`with Y or part of Y forms a 5-, 6- or 7-membered ring containing the nitrogen atom.
`
`Reconsideration is requested.
`
`REMARKS
`
`The claims have been amended to deal with objections raised by the
`
`Examiner under Section 112.
`
`In particular, the references to ~optionally
`
`substituted H have been suitably replaced and antecedent basis has been
`
`provided in claims 3 and 5.
`
`The applicants do not understand the basis for the Examiner's
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`antecedency objection against claims 6-8. In claim 6, the method ::refers to
`
`a speci f ic oxaborole which clearly has antecedency in independent c'laim 1.
`
`The group Y of claim 6 is clearly alkyleneamino or carbonylalkyleneamino
`
`and both terms have clear antecedents in the definition of R in claim 1. A
`
`similar explanation is true of claim 7. Claim 8 further defines the medium
`
`which also has its antecedent in claim 1. Reconsideration of this aspect
`
`of the Examiner'S Section 112 rejection is requested.
`
`The Examiner's objection to "heterocyclyl/l has been noted. However,
`
`this term does not appear in the claims.
`
`If the Examiner intends to refer
`
`to "heteroaryl", it is submitted that this term is clear and definite.
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`The reference to "boronophthalide" is, in fact, correct.
`
`Regarding claims 2 and ~1, the Examiner alleges that the point of
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`fusion of the phenyl ring is indefinite. The applicants disagree since, in
`
`both claims, the ring is defined as formed by A and D together with both
`
`the carbon atoms to which A and D are attached. Hence, the point of fusion
`
`with the oxaborole ring is clearly defined as the -C=C- bond to which the
`
`~.-~
`
`(~L-----
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`AUSTIN ET AL
`Serial No. 08/750,081
`
`groups A and D are attached. The oxaborole wherein A and D complete a
`
`fused phenyl ring can be described as a I-hydroxy-3H-l,2-benzoxaborole (or
`
`derivative thereof)as described in FR 2,195,401 but is usually referred to
`
`as a boronophthalide (or derivative thereof) as described, for example, in
`
`.J. Org. Chern., li(6) :1669 (1969). Both terms are synonymous.
`
`In both
`
`cases, the point of fusion is clearly defined and understood by the person
`
`skilled in the art. Since the points of fusion of the phenyl ring are
`
`defined, there remain only four positions in the fused phenyl ring which
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`are available for substitution. Hence, the positions of possible
`
`substitution are also clearly defined and this would again be readily
`
`understood by the skilled addressee.
`
`In view of the foregoing comments and amendments, reconsideration of
`
`the Section 112 rejection is requested.
`
`Reconsideration of the Section 102(b) rejection of claims 9 and 11 as
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`anticipated by French patent 7,329,370 is also requested. The subject
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`matter of claims 9 and 11 is not disclosed by the French reference.
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`More specifically, the reference discloses 1-hydroxy-3H-1,2-
`
`benzoxaborole. As noted earlier herein, this compound is alternatively
`
`referred to as boronophthalide. This compound has been specifically
`
`disclaimed from claim 9 and, hence, also from dependent claim 11.
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`Accordingly, it is submitted that claims 9 and 11 define subject matter
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`which is novel over the French reference.
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`Reconsideration of the Section l03(a) rejection of claims 1-4, 8, 9,
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`11, 15 and 16 as unpatentable over the French patent is also requested.
`
`To start with, the French~reference does not disclose the presently
`
`claimed oxaboroles as alleged by the Examiner.FR 2,195,401 discloses only
`
`boronophthalide itself and the use of this single compound as an
`
`antimicrobial agent.
`
`J~
`
`1"'-------
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`AUSTIN ET AL
`Serial No. 08/750,081
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`The Examiner further alleges that it would be obvious to utilize the
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`compounds of Emrick et aI, Andress, Jr. et al and Nauta as antimicrobial
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`agents. The applicants do not understand this rationale. The oxaborole
`
`ring as defined by formula 1 of claim 1 contains a 5-membered ring
`
`containing 3 carbon atoms, an oxygen atom and a boron atom. The compounds
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`disclosed by Nauta are glyceryl ethers of diphenylmethane and do not
`
`contain an oxaborole ring. Whi+e the compounds disclosed by Andress, Jr.
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`contain a 5-membered ring containing a boron atom, the ring also contains
`
`two oxygen atoms. This is not an oxaborole ring (note definition of X in
`
`claim 1). The ring system disclosed by Emrick is similar to Andress, Jr.
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`and again contains boron with two oxygen atoms. Consequently, the skilled
`
`person has no reason to combine any of Nauta I Andress or Emrick with FR
`
`2,195,401 either individually or collectively. Accordingly, the applicants
`
`submit that the present claims are clearly inventive over these citations.
`
`The Examiner indicates that claims 5-7, 10-14 and 17-23 would be
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`allowable if presented in independent form with the Section 112 issues
`
`addressed. The dependency of these claims has been retained as all of the
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`applicants' claims are thought to be allowable for the reasons stated.
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`Favorable action is requested.
`
`Respectfully submitted,
`
`PILLSBURY MADISON & SUTRO LLP
`
`a~v~(~
`
`.
`
`By
`
`Paul N. Kokulis
`Reg. No. 16773
`
`PNK:mh
`1100 New York Avenue, N.W.
`9 th Floor, East Tower
`Washington, D.C. 20005-3918
`Phone:
`(202) 861-3503
`
`5
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