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 .
DETAILED ACTION
1. Claims 16, 17, 19-25 are pending in the current application.
2. This application is a DIV of 17/408,864 08/23/2021.
Response to Amendments
3. Rejections of canceled claims are withdrawn. The rejection of claims 12, 14-18 under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement is withdrawn based upon the amendments. The rejection of claim(s) 12, 14-15, 18 under 35 U.S.C. 102(a)(1) as being anticipated by Li GB 2495458 A is withdrawn based upon the amendments. The rejection of claim(s) 16-17, under 35 U.S.C. 103 as being unpatentable over Li GB 2495458 A is withdrawn based upon the amendments. New grounds of rejection appear below.
Claim Rejections - 35 USC § 103
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.
4. Claim(s) 16-17, 19-25 are rejected under 35 U.S.C. 103 as being unpatentable over Li GB 2495458 A in view of Andreeta “Crystallization - Science and Technology” 2012, page 192. Li on page 7 discloses the following process:
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The last section 200 ml to 100 ml of acetonitrile to 1 g of carboprost. The temperature range is 0oC -100oC which includes the claimed range. Acetonitrile is the first selection and in Example 2 on page 11, it is the crystallization solvent. With regard to the water content of acetonitrile in claim 17, this a commercial grade available and appears to be what Li used. The only difference may be the use of anhydrous acetonitrile, although this is unclear since typically anhydrous solvents are used. The acetonitrile of Li just appears to be a commercial grade with minimal water since no water is mentioned. The process is also written with the leading phrase “comprising”, which does not exclude additional steps. Since the compound was known to be recrystallized from acetonitrile, any method that places the compound in acetonitrile, by solution addition or direct dissolution would be expected to give the same or similar result.
The instant claims are drawn to two recrystallizations. Melting point is depressed by contamination, and increased purity results in a higher melting range. Often contaminated solids are purified by multiple recrystallizations. It would be obvious to conduct the recrystallization in acetonitrile multiple times. Regarding the use of anhydrous acetonitrile, Andreeta on page 192 under “2.1.6 Moisture and humidity” explains:
When recrystallizing from hygroscopic organic solvents, care should be taken to use only properly dried solvents (Table 3) or newly opened containers from reputable suppliers. If a crystallization process generates a metastable intermediary form, it can absorb water when exposed to moisture and change into a hydrate. Water molecules, because of their small size and multidirectional hydrogen bonding capabilities, are particularly suited to fill structural voids (Manek & Kolling, 2004).
Li describes the so formed crystalline carboprost tromethamine at page 6 lines 3-15, where a maximum peak in the DSC of the claim 20, “106.4 ± 1oC”, which is the range 105.4 to 107.4 oC described by Li on line 14 as “103.97 ± 5oC”, which is the range 98.97 – 108.97oC. The peaks at the 2θ angles of the instant claim 21 are recited in lines 5-6, “6.6 ± 0.2o, 9.9 ± 0.2o, 18.5 ± 0.2o,” giving the ranges for each peak of 6.4-6.8o, 9.7-10.1o, 18.3-18.7o, respectively, which are equivalent to the first three claimed peaks. With respect to the last peak in claim 21 recited at 21.86 to 21.90, Figure 1 on page 2 of Li has this peak in the diffractogram as peak 15 giving a peak height of maximum 17.7 % of peak 1. Figure 11 is shown below on the left with instant Figure 1 on the right:
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These are the same polymorph. Looking at the Li region from 15-25 degrees θ comparing to in the instant diffractogram of figure 1 in the same region they are the same:
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Regarding the amounts of impurities in claims 23-25, since it is a crystalline solid that does not show evidence of the other isomers in the diffractogram this is an inherent feature of the pure material. The melting point is sharp and the IR in Li does not show peaks for the trans isomers, which will appear.
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.
8. Claim 16, 17, 19-25 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 16-17 of copending Application No. 17/408,864 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because while the instant claims embrace an additional recrystallization, contaminated solids are purified by multiple recrystallizations. Melting point is depressed by contamination, and increased purity results in a higher melting range. It would be obvious to conduct the recrystallization in acetonitrile multiple times. The materials have all the properties of claims 20-25.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
9. Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DAVID K O'DELL whose telephone number is (571)272-9071. The examiner can normally be reached on Monday - Friday 9:30 - 7:00 PM.
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/DAVID K O'DELL/Primary Examiner, Art Unit 1621
1 This figure is also available in Li’s Canadian filing, CA 2805959, and the Chinese PCT filing, WO20120100089 which have clearer images.