DETAILED ACTION
1. The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
2. This application is a 371 of App. No. PCT/EP2021/081982, filed on 11/17/2021. The preliminary amendment filed on 05/17/2024 is entered and acknowledged by the Examiner.
3. Claims 1-15 are pending. Claims 1-15 are under examination on the merits.
Information Disclosure Statement
4. The information disclosure statements submitted on 06/18/2024, and 07/02/2026 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the examiner has considered the information disclosure statements.
Priority
5. Acknowledgment is made of applicant's claim for foreign priority based on EP application filed 11/17/2021. However, applicant has not filed a certified copy of the EP application PCT/EP2021/081982 as required by 35 U.S.C. 119(b).
Claim Objections
6. Claim 1 is objected to because of the following informalities: It is suggested that claim uses the transitional phrases such that “A fragrance according to formula (Ia) and/or (Ib)” be deleted and "A fragrance comprising formula (Ia) and/or (Ib)" be inserted in its stead so as to engender claim language clarity. Appropriate correction is required.
7. Claim 2 is objected to because of the following informalities: It is suggested that “The fragrance of Claim 1 containing” be deleted and "The fragrance according to claim 1, wherein" be inserted in its stead so as to engender claim language clarity. Appropriate correction is required.
8. Claim 3 is objected to because of the following informalities: It is suggested that “wherein R1 and R2” be deleted and "wherein R1 and R2" be inserted in its stead so as to engender claim language clarity. Appropriate correction is required.
9. Claims 4-6 are objected to because of the following informalities: It is suggested that “The mixture of Claim 3,” be deleted and "The fragrance mixture according to claim 3," be inserted in its stead so as to engender claim language clarity. Appropriate correction is required.
10. Claims 4, 6 are objected to because of the following informalities: It is suggested that “The mixture of Claim 3, comprising” be deleted and "The fragrance mixture according to claim 3, wherein" be inserted in its stead so as to engender claim language clarity. Appropriate correction is required.
11. Claims 8-10 are objected to because of the following informalities: It is suggested that “The process of Claim 7, wherein” be deleted and "The process according to claim 7, wherein" be inserted in its stead so as to engender claim language clarity. Appropriate correction is required.
12. Claims 11-15 are objected to because of the following informalities: It is suggested that “the fragrance of Claim x” be deleted and "The fragrance according to claim x" be inserted in its stead so as to engender claim language clarity. It is noted that claims 11-15 should depend only on claim 1 to avoid the claim renumbering during allowance. It is further suggested that the Applicant rewrite claims 11-15 as new claims 16-20 to depend on claim 3. Appropriate correction is required.
13. Claim 12 is objected to because of the following informalities: It is suggested that “b.w.” be deleted and "by wt. or by weight" be inserted in its stead so as to engender claim language clarity. Appropriate correction is required.
Claim Rejections - 35 USC § 112
14. The following is a quotation of 35 U.S.C. 112(b):
(B) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
15. Claim 4 is rejected under 35 U.S.C. 112, second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which applicant regards as the invention. Claim 4 recites the term “components (a) and (b)” in line 1. There are insufficient antecedent basis for this limitation in the claim.
For the purpose of examination against the prior art, claim 4 is construed to recite “The components (a) and (b)”.
16. Claim 6 is rejected under 35 U.S.C. 112, second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which applicant regards as the invention. Claim 6 recites the term “components (a+b) and (c)” in line 1. There are insufficient antecedent basis for this limitation in the claim.
For the purpose of examination against the prior art, claim 6 is construed to recite “The components (a+b) and (c)”.
17. Claim 15 is rejected under 35 U.S.C. 112, second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which applicant regards as the invention. Claim 15 provides for the use of the fragrance of claim 1, the fragrance mixture of claim 3 or the perfume composition of claim 11, but, since the claim does not set forth any steps involved in the method/process, it is unclear what method/process applicant is intending to encompass. A claim is indefinite where it merely recites a use without any active, positive steps delimiting how this use is actually practiced.
Claim 15 is also rejected under 35 U.S.C. 101 because the claimed recitation of a use, without setting forth any steps involved in the process, results in an improper definition of a process, i.e., results in a claim which is not a proper process claim under 35 U.S.C. 101. See for example Ex parte Dunki, 153 USPQ 678 (Bd.App. 1967) and Clinical Products, Ltd. v. Brenner, 255 F. Supp. 131, 149 USPQ 475 (D.D.C. 1966).
Claim Rejections - 35 USC § 103
18. The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
19. Claims 7-10 are rejected under 35 U.S.C. 103(a)(1) as being unpatentable over Mancini et al. (synthesis of (S)-(+)-cryptone, Gazzetta chimica ltaliana, 1988, vol. 118, pages 447-449, hereinafter “Mancini”, see IDS dated 06/18/2024 ) in view of Kolomeyer et al. (US Pub. No. 2017/0035079 A1, hereinafter “Kolomeyer”) or Thomas et al.(US Pat. No. 3,993,604, hereinafter “Thomas”).
Regarding claim 7: Mancini teaches the production of (5-isopropyl-2-methylene-cyclohexyl) acetate from 5-isopropyl-2-methylene-cyclohexanol by reaction with acetyl chloride in pyridine (=alkaline source and organic solvent) at room temperature (Page 447, right Col., reaction step 1, Compound 2). The method according to the present claim 7 differs therefrom in that acetyl acetate used as reactant and reaction takes place at a temperature ranging from 110°C to 130°C. No evidence of a surprising effect linked to the different temperature
and acetylating compound has been provided by the present application. The objective problem solved over Mancini is thus regarded as the provision of an alternative process.
However, a skilled person is looking for alternative methods to produce (5-isopropyl-2-methylene-cyclohexyl) acetate would have considered the state of the art dealing with similar acetylation reactions. Such state of the art is provided by Kolomeyer (Page 4, [0029]) and/or Thomas (Col. 7, lines 10-35, synthesis steps). Both Kolomeyer or Thomas teaches acetylation of structurally closely related cyclohexanols (isocarveol, carveol) by reaction with various acetylating agents, including acetic anhydride (=acetyl acetate) under conditions including a base catalyst and at a temperature ranging from 20°c to 180°C. In the light thereof, a skilled person would consider the conditions defined in the present claim 7 when looking for
alternative ways of preparing (5-isopropyl-2-methylene-cyclohexyl) acetate. Hence, no inventive contribution can be seen starting from Mancini in combination with Kolomeyer and/or Thomas.
Therefore, the subject matter as a whole would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention was made, since it is held to be a prima facie case of obviousness since a person of ordinary skill in the art would have recognized the interchangeability of the element (i.e. functional group) shown in the prior art for the corresponding element disclosed in the specification wherein the side chains syntheses merely done by routine experimentation. Caterpillar Inc. v. Deere & Co., 224 F.3d 1374, 56 USPQ2d 1305 (Fed. Cir. 2000).
Regarding claims 8-10: The disclosure of Mancini in view of Kolomeyer and/or Thomas is adequately set forth in paragraph above and is incorporated herein by reference. Kolomeyer teaches the 5-isopropyl-2-methylene-cyclohexanol and the acetyl acetate are reacted in a molar ratio of about 1:1.2 (Page 6, [0040]). Toluene as organic solvent and sodium carbonate as alkaline source are well-known and commonly applied solvent and alkaline agent and as such represent further straightforward alternatives readily available to one skilled in the art.
20. Claims 7-10 are rejected under 35 U.S.C. 103(a)(1) as being unpatentable over Schenck et al. (Zur chemischen und sterischen Selektivitat der photosensibilisierten O2-Ubertragung auf ( + )Limonen und (+)-Carvomenthen, JUSTUS LIEBIGS ANNALEN DER CHEMIE, vol. 67 4, no. 1, 9 July 1964, pages 93-117, hereinafter “Schenck”, see IDS dated 06/18/2024 ) in view of Kolomeyer et al. (US Pub. No. 2017/0035079 A1, hereinafter “Kolomeyer”) or Thomas et al.(US Pat. No. 3,993,604, hereinafter “Thomas”).
Regarding claim 7: Schenck teaches the production of (5-isopropyl-2-methylene-cyclohexyl) acetate from (5-isopropyl-2-methylene-cyclohexyl)acetate (Page 113, Compound VIIb). The method according to the present claim 7 differs therefrom in that acetyl acetate used as reactant and reaction takes place at a temperature ranging from 110°C to 130°C. No evidence of a surprising effect linked to the different temperature and acetylating compound has been provided by the present application. The objective problem solved over Schenck is thus regarded as the provision of an alternative process.
However, a skilled person is looking for alternative methods to produce (5-isopropyl-2-methylene-cyclohexyl) acetate would have considered the state of the art dealing with similar acetylation reactions. Such state of the art is provided by Kolomeyer (Page 4, [0029]) and/or Thomas (Col. 7, lines 10-35, synthesis steps). Both Kolomeyer or Thomas teaches acetylation of structurally closely related cyclohexanols (isocarveol, carveol) by reaction with various acetylating agents, including acetic anhydride (=acetyl acetate) under conditions including a base catalyst and at a temperature ranging from 20°c to 180°C. In the light thereof, a skilled person would consider the conditions defined in the present claim 7 when looking for
alternative ways of preparing (5-isopropyl-2-methylene-cyclohexyl) acetate. Hence, no inventive contribution can be seen starting from Schenck in combination with Kolomeyer and/or Thomas.
Therefore, the subject matter as a whole would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention was made, since it is held to be a prima facie case of obviousness since a person of ordinary skill in the art would have recognized the interchangeability of the element (i.e. functional group) shown in the prior art for the corresponding element disclosed in the specification wherein the side chains syntheses merely done by routine experimentation. Caterpillar Inc. v. Deere & Co., 224 F.3d 1374, 56 USPQ2d 1305 (Fed. Cir. 2000).
Regarding claims 8-10: The disclosure of Schenck in view of Kolomeyer and/or Thomas is adequately set forth in paragraph above and is incorporated herein by reference. Kolomeyer teaches the 5-isopropyl-2-methylene-cyclohexanol and the acetyl acetate are reacted in a molar ratio of about 1:1.2 (Page 6, [0040]). Toluene as organic solvent and sodium carbonate as alkaline source are well-known and commonly applied solvent and alkaline agent and as such represent further straightforward alternatives readily available to one skilled in the art.
Allowable Subject Matter
21. Claims 1-6, 11-15 would be allowable if rewritten or amended to overcome the objection(s) and the rejection(s) under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), 2nd
paragraph, set forth in this Office action.
22. The following is an examiner’s statement of reasons for allowance:
The most pertinent prior art known by the Examiner is in the attached form PTO-892.
Mancini or Schenck teaches (5-isopropyl-2-methylene-cyclohexyl) acetate, but different enantiomers thereof, namely the (1 R,5R)- and (1 S,5R)-enantiomers, whereas the presently
claimed formula (la) and (lb) represent the (1 R,5S)- and (1 S,5S)-enantiomers, respectively.
Kolomeyer or Thomas does not teach a (5-isopropyl-2-methylene-cyclohexyl) acetate,
but structurally related acetates, such as isocarvyl acetate, carvyl acetate and dihydrocarvyl acetate.
Prior art of record, taken alone or in combination, do not teach or fairly suggest the claimed (5-isopropyl-2-methylenecyclohexyl) acetate compound having the specific enantiomeric configuration represented by the formula (la) and/or (lb) defined in claims 1-2, or a mixture thereof with at least one of compounds of formula (Ila) and (llb) as defined in claims 3-6. Therefore, the instant claims are distinguished over the prior art.
Examiner Information
23. Any inquiry concerning this communication or earlier communications from the examiner should be directed to Bijan Ahvazi, Ph.D. whose telephone number is (571) 270-3449. The examiner can normally be reached on Mon-Fri 9.00 A.M. -7 P.M..
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Joseph Del Sole can be reached on 571-272-1130. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://pair-direct.uspto.gov. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative or access to the automated information system, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/Bijan Ahvazi/
Primary Examiner, Art Unit 1763
07/16/2026
bijan.ahvazi@uspto.gov
Prosecution Insights