DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Status of the Claims
Claims 99-118 are pending. Claims 103-104 and 117-118 are withdrawn. Claims 99-102 and 105-116 are rejected.
Election/Restrictions
Applicant's election of Group I (claims 99-116) and of the elected species Compound 15b
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without traverse in the reply filed on 08/04/2025 is acknowledged. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)).
Claims 99-102, 105-112 and 115-116 read on Applicant’s species election of Compound 15b. Examination of the elected invention was conducted in accordance with the MPEP 803.02.
The elected species is free of the prior art; therefore, examination of the Markush-type claim has been extended to the scope of the structural formula of claim 99 wherein:
the
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moiety is
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;
R1a and R1b are each hydrogen, unsubstituted C1-4 alkyl or halogenated C1-4 alkyl;
R2 is hydrogen or C1 alkyl;
R3 is C1-C5 alkyl;
R4 is -(C0 alkyl)-heteroaryl or -(C0 alkyl)-heterocycloalkyl; and
R5 is hydrogen.
Since art was found on nonelected species, subject matter not embraced by the above-identified non-elected species is therefore withdrawn from further consideration. Claims 103 and 104 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Incidental to the search of the nonelected species additional prior art was discovered that is related to:
1) nonelected species of perfluoro-tert-butanol;
2) species wherein the
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ring moiety is
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;
3) species wherein R4 is -(C1 alkyl)-heteroaryl or -(C1 alkyl)-heterocycloalkyl; and
4) species wherein R5 is -C(O)(C1 alkyl). In the interest of compact prosecution, one or more rejections over above-identified nonelected species are presented below.
Applicant is reminded that upon the cancellation of claims to a non-elected invention, the inventorship must be amended in compliance with 37 CFR 1.48(b) if one or more of the currently named inventors is no longer an inventor of at least one claim remaining in the application. Any amendment of inventorship must be accompanied by a request under 37 CFR 1.48(b) and by the fee required under 37 CFR 1.17(i).
Priority
This application is a 371 of PCT/CA2020/050965 filed 07/10/2020 which claims benefit of PRO 62/873,697 filed 07/12/2019.
Information Disclosure Statement
The information disclosure statements (IDS) dated 08/25/2023, 10/25/2023 and 09/24/2024 have been considered.
Specification
The disclosure is objected to because of the following informalities:
Example 7 on page 68 appears to be misnamed and is missing “6,6,9-” at the beginning of the name.
Claim Rejections - 35 USC § 112
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.
Claim 115 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 115 is rejected because the name of the compound “1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-2-yl)-1,3,4-oxadiazol-2(3H)-one” does not properly define a structure. It appears as though the correct name should be “5-(1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-2-yl)-1,3,4-oxadiazol-2(3H)-one” given the name of compound 4b on page 77 of the specification.
Applicant may amend the claim to include the proper chemical name.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
(1 of 3) Claims 99-102, 105-113 and 116 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Zehavi, U. et al. “O- and C-D-glucosyluronic acid derivatives of Δ1-tetrahydrocannabinol: Synthesis and differential behavior to β-glucoronidase” Carbohydrate Research, 1981, pp. 143-147, Vol. 98, as cited in the IDS dated 08/25/2023.
Zehavi et al. teach compound 6 on page 144:
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. Compound 6 reads on the structural formula of claims 99,
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, and 111,
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, wherein:
the
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moiety is
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(see instant claim 100);
R1a and R1b are each C1 alkyl (see instant claims 101-102);
R2 is C1 alkyl (see instant claims 105-106);
R3 is C5 alkyl (see instant claim 107);
R4 is -(C0 alkyl)-heterocycloalkyl (see instant claim 112);
R5 is hydrogen (see instant claims 108-110); and
the heterocycloalkyl is substituted with 4 R7 groups which are either -CO2RA or -ORA wherein RA is hydrogen in each instance (see instant claim 113). Compound 6 therefore anticipates instant claims 99-102 and 105-113.
Regarding instant claim 116 drawn to a pharmaceutical composition comprising the compound of claim 99 and a pharmaceutically acceptable excipient, diluent, or carrier, Zehavi et al. also describe a solution of β-D-glucoronidase and a saturated solution of Compound 6 (1:8 by volume) in 4:1 (v/v) sodium acetate-acetic acid buffer and 1,3-propanediol. See paragraph bridging pages 146 and 147. Thus, instant claim 116 is anticipated.
Zehavi also teaches compound 2 on page 144:
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. Compound 2 reads on the structural formula of claim 99,
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, wherein:
the
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moiety is
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;
R1a and R1b are each C1 alkyl (see instant claims 101-102);
R2 is C1 alkyl (see instant claims 105-106);
R3 is C5 alkyl (see instant claim 107);
R4 is -(C0 alkyl)-heterocycloalkyl (see instant claim 112);
R5 is hydrogen (see instant claims 108-110); and
the heterocycloalkyl is substituted with 4 R7 groups which are either -CO2RA or -ORA wherein one RA is C1 alkyl and the remaining three are each C2 alkyl substituted with one oxo group (see instant claims 99 and 113). Compound 2 therefore anticipates instant claims 99, 101-102, 105-110, and 112-113.
Regarding instant claim 116 drawn to a pharmaceutical composition comprising the compound of claim 99 and a pharmaceutically acceptable excipient, diluent, or carrier, Zehavi et al. also describe a solution of Compound 2 in dichloromethane wherein concentrated sodium chloride was added. See third paragraph of page 145. A person having ordinary skill in the art would expect that the concentrated sodium chloride solution is comprised of water as solvent. Thus, claim 116 is anticipated by the reference.
Zehavi also teaches compound 5 on page 144:
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. Compound 5 reads on the structural formula of claim 99,
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, wherein:
the
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moiety is
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(see instant claim 100);
R1a and R1b are each C1 alkyl (see instant claims 101-102);
R2 is C1 alkyl (see instant claims 105-106);
R3 is C5 alkyl (see instant claim 107);
R4 is -(C0 alkyl)-heterocycloalkyl (see instant claim 112);
R5 is -C(O)(C1 alkyl) (see instant claim 108); and
the heterocycloalkyl is substituted with 4 R7 groups which are either -CO2RA or -ORA wherein one RA is C1 alkyl and the remaining three are each C2 alkyl substituted with one oxo group (see instant claims 99 and 113). Compound 5 therefore anticipates instant claims 99-102, 105-108, and 112-113.
Regarding instant claim 116 drawn to a pharmaceutical composition comprising the compound of claim 99 and a pharmaceutically acceptable excipient, diluent, or carrier, Zehavi et al. also describe a solution of Compound 5 in ethanol. See third paragraph of page 146. Thus, claim 116 is anticipated by the reference.
(2 of 3) Claims 99-102, 105-112, 114 and 116 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Aizikovich in US 2021/0087159, which claims benefit to provisional application 62/680,110 filed 06/04/2018.
Aizikovich teaches THCA and CBDA derivatives such as compound Ia19 on page 7:
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. Compound Ia19 reads on the structural formula of claims 99,
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, and 111,
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, wherein:
the
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moiety is
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(see instant claim 100);
R1a and R1b are each C1 alkyl (see instant claims 101-102);
R2 is C1 alkyl (see instant claims 105-106);
R3 is C5 alkyl (see instant claim 107);
R4 is -(C1 alkyl)-heterocycloalkyl (see instant claim 112) wherein the alkyl is substituted with one oxo group; and
R5 is hydrogen (see instant claims 108-110).
Compound Ia19 therefore anticipates instant claims 99-102 and 105-112.
Aizikovich teaches THCA and CBDA derivatives such as compound Ia20 on page 7:
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. Compound Ia20 reads on the structural formula of claims 99,
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, and 111,
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, wherein:
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moiety is
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(see instant claim 100);
R1a and R1b are each C1 alkyl (see instant claims 101-102);
R2 is C1 alkyl (see instant claims 105-106);
R3 is C5 alkyl (see instant claim 107);
R4 is -(C1 alkyl)-heteroaryl (see instant claim 112) wherein the alkyl is substituted with one oxo group; and
R5 is hydrogen (see instant claims 108-110).
Compound Ia20 therefore anticipates instant claims 99-102 and 105-112.
Aizikovich teaches THCA and CBDA derivatives such as compound Ia23 on page 7:
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. Compound Ia23 reads on the structural formula of claims 99,
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, and 111,
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, wherein:
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moiety is
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(see instant claim 100);
R1a and R1b are each C1 alkyl (see instant claims 101-102);
R2 is C1 alkyl (see instant claims 105-106);
R3 is C5 alkyl (see instant claim 107);
R4 is -(C0 alkyl)-heterocycloalkyl (see instant claim 112); and
R5 is hydrogen (see instant claims 108-110).
Compound Ia23 therefore anticipates instant claims 99-102 and 105-112.
Aizikovich teaches THCA and CBDA derivatives such as compound Ia24 on page 7:
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. Compound Ia24 reads on the structural formula of claims 99,
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, and 111,
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, wherein:
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(see instant claim 100);
R1a and R1b are each C1 alkyl (see instant claims 101-102);
R2 is C1 alkyl (see instant claims 105-106);
R3 is C5 alkyl (see instant claim 107);
R4 is -(C0 alkyl)-heteroaryl (see instant claim 112);
R5 is hydrogen (see instant claims 108-110); and
the heteroaryl is substituted with one R8 group which is an unsubstituted C1 alkyl (see instant claim 114).
Compound Ia24 therefore anticipates instant claims 99-102, 105-112 and 114.
Regarding instant claim 116 drawn to a pharmaceutical composition comprising the compound of claim 99 and a pharmaceutically acceptable excipient, diluent, or carrier, Aizikovich also describes pharmaceutical compositions of the claimed compounds comprising one or more pharmaceutically acceptable excipients. See paragraph [0070] on page 10. Thus, instant claim 116 is anticipated.
(3 of 3) Claims 99-102, 105-110, 112 and 116 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Pavlik and Toren, “Perfluoro-t-butyl Alcohol and Its Esters” J. Org. Chem., Vol. 35, No. 6, 1970, pp. 2054-2056.
Pavlik and Toren teach the compound (CF3)3COH (see page 2055, left column, second paragraph), which is a hydrolyzed metabolite of the compound
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of structural formula of claim 99,
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, wherein:
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(see instant claim 100);
R1a is methyl (see instant claims 101-102);
R1b is C(O)OC(CF3)3 (see instant claims 101-102);
R2 is methyl (see instant claims 105-106);
R3 is C5 alkyl (see instant claim 107);
R4 is -(C0 alkyl)-heterocycloalkyl (see instant claim 112); and
R5 is hydrogen (see instant claims 108-110).
Regarding instant claim 116 drawn to a pharmaceutical composition comprising the compound of claim 99 and a pharmaceutically acceptable excipient, diluent, or carrier, Pavlik and Toren describe a hydrolysis reaction of (CF3)3COOCCH3 and (CF3)3COOCCF3 esters in 50 mL of 1:1 acetone-water solution. See section “Hydrolysis Data” bridging pages 2055 and 2056. They note the decrease in pH as the acid is produced by hydrolysis of the ester. See page 2056, left column, lines 8-9. A person having ordinary skill in the art would be able to determine that the hydrolysis products of both (CF3)3COOCCH3 and (CF3)3COOCCF3 include the alcohol (CF3)3COH in addition to acetic acid and trifluoroacetic acid, respectively. Since the hydrolysis takes place with water as a solvent, the reference anticipates claim 116.
Thus, the disclosed compound anticipates instant claims 99-102, 105-110, 112 and 116.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the claims at issue are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); and In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on a nonstatutory double patenting ground provided the reference application or patent either is shown to be commonly owned with this application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The USPTO internet Web site contains terminal disclaimer forms which may be used. Please visit http://www.uspto.gov/forms/. The filing date of the application will determine what form should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to http://www.uspto.gov/patents/process/file/efs/guidance/eTD-info-I.jsp.
Claims 99-102, 105-114 and 116 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 125-133, 135 and 138-142 of copending Application No. 17/765,853 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because the copending claims recite several species of compounds that anticipate the instant claims.
Reference claim 125 is drawn to a compound having structural formula:
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and claim 140 recites several compounds that are embraced by instant formula of the closely related structural formula of claim 99:
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. Specifically, claim 140 of copending application ‘853 recites compounds 34b-49b, as defined on pages 99-101 of the specification, that are embraced by the instant formula within the confines of the expanded search described in the Elections/Restrictions section above. The second to last compound on page 18 recited in claim 140, 1-(1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-2-carbonyl)pyrrolidine-3-one, for example, (as identified as compound 42b on page 100 of the specification:
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) reads on the structural formula of claims 99,
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, and 111,
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, wherein:
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(see instant claim 100);
R1a and R1b are each C1 alkyl (see instant claims 101-102);
R2 is C1 alkyl (see instant claims 105-106);
R3 is C5 alkyl (see instant claim 107);
R4 is -(C1 alkyl)-heterocycloalkyl (see instant claim 112) wherein the alkyl is substituted with an oxo group;
R5 is hydrogen (see instant claims 108-110); and
the heterocycloalkyl is substituted with one R7 group which is an oxo (see instant claim 113).
Compound 42b therefore anticipates instant claims 99-102, 105-113.
As another example, the first compound on page 19 recited in claim 140, (1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-2-yl)(1H-indol-1-yl)methanone, for example, (as identified as compound 44b on page 100 of the specification:
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) reads on the structural formula of claims 99,
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, and 111,
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, wherein:
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(see instant claim 100);
R1a and R1b are each C1 alkyl (see instant claims 101-102);
R2 is C1 alkyl (see instant claims 105-106);
R3 is C5 alkyl (see instant claim 107);
R4 is -(C1 alkyl)-heteroaryl (see instant claim 112) wherein the alkyl is substituted with an oxo group; and
R5 is hydrogen (see instant claims 108-110).
Compound 42b therefore anticipates instant claims 99-102, 105-112.
Regarding instant claim 114, which is drawn to the compound of claim 99 wherein R8 is:
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, the copending claim 139 recites a similar list of limitations for R8:
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. Per instant claim 99 and copending claim 125, R8 is the optional substituent on aryl and/or heteroaryl ring, such as one at position R4. Compound 42b of the copending case described above has an unsubstituted heteroaryl at position R4, but it would have been obvious to a person having ordinary skill in the art to arrive at an analog of compound 42b that incorporates one of the recited limitations of copending claim 139 given the structure of compound 46b for instance, which has a methyl-substituted aziridinyl ring, i.e. R8 is C1 alkyl. Compound 46b can be found on page 100 of the reference specification and is (1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-2-yl)((S)-2-methylaziridin-1-yl)methanone, which is the third item on page 19 of claim 140.
Regarding instant claim 116 drawn to a pharmaceutical composition comprising the compound of claim 99 and a pharmaceutically acceptable excipient, diluent, or carrier, copending claim 142 of ‘853 also describes a pharmaceutical composition of the claimed compounds comprising pharmaceutically acceptable excipient, diluent, or carrier. Thus, instant claim 116 is anticipated.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jalisa H. Ferguson whose telephone number is (703)756-1489. The examiner can normally be reached Monday - Friday 9:00am - 5:00pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Joseph McKane can be reached at (571) 272-0699. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/J.H.F./Examiner, Art Unit 1626
/JOSEPH K MCKANE/Supervisory Patent Examiner, Art Unit 1626