PATENT CLAIM ANALYSIS

Application Number: 16166893
Application Type: Utility
Filing Date: 2018-10
Publication Date: 2019-02
Patent Classification: ["540", "529000"]

Abstract:
This invention provides efficient and scalable enantioselective methods that yield 2-alkyl-2-allylcycloalkyanone compounds with quaternary stereogenic centers. Methods include the method for the preparation of a compound of formula (I): comprising treating a compound of formula (II) or (III): with a palladium (II) catalyst under alkylation conditions.

Claim (Index 42):
A method of preparing a pharmaceutical agent, comprising preparing a compound of formula (I): the preparing comprising treating, with a Pd(II) catalyst in an organic solvent,\n (i) a compound of formula (II) or (III) or a salt thereof: \n or\n (ii) a compound of formula (IV) or (V) or a salt thereof: \n and a compound of formula (X): wherein the Pd(II) catalyst is used in an amount from about 0.01 mol % to about 3 mol % relative to the compound of formula (II), (III), (IV), or (V), wherein, as valence and stability permit, R 1  represents hydrogen or substituted or unsubstituted alkyl, alkenyl, alkynyl, aralkyl, aryl, (5- to 10-membered heteroaryl)alkyl, 5- to 10-membered heteroaryl, (cycloalkyl)alkyl, cycloalkyl, (3- to 10-membered heterocyclyl)alkyl, 3- to 10-membered heterocyclyl, alkoxy, amino, or halo; R 2 , R 3 , R 4 , R 5 , R 12 , R 13 , R 14 , and R 15  are independently selected for each occurrence from hydrogen, hydroxyl, halo, nitro, alkyl, alkenyl, alkynyl, cyano, carboxyl, sulfate group, amino, alkoxy, alkylamino, alkylthio, hydroxyalkyl, alkoxyalkyl, aminoalkyl, mercaptoalkyl, ether group, thioether group, ester group, amide, thioester group, carbonate group, carbamate group, urea group, sulfonate group, sulfone group, sulfoxide group, sulfonamide group, acyl, acyloxy, acylamino, aryl, (5- to 10-membered heteroaryl)alkyl, cycloalkyl, 3- to 10-membered heterocyclyl, aralkyl, arylalkoxy, (5- to 10-membered heteroaryl)alkyl, (cycloalkyl)alkyl, and (3- to 10-membered heterocyclyl)alkyl; W represents, as valence permits, \u2014O\u2014, \u2014S\u2014, \u2014NR 6 \u2014, \u2014CR 7 R 8 \u2014, \u2014C(O)\u2014, \u2014CR 7 \u2550, or \u2014N\u2550; R 6  represents hydrogen or optionally substituted alkyl, cycloalkyl, (cycloalkyl)alkyl, aryl, aralkyl, 5- to 10-membered heteroaryl, (5- to 10-membered heteroaryl)alkyl, alkenyl, alkynyl, \u2014C(O)alkyl, \u2014C(O)aryl, \u2014C(O)aralkyl, \u2014C(O) (5- to 10-membered heteroaryl), \u2014C(O)-(5- to 10-membered heteroaryl)alkyl, \u2014C(O)O(alkyl), \u2014C(O)O(aryl), \u2014C(O)O(aralkyl), \u2014C(O)O(5- to 10-membered heteroaryl), \u2014C(O)O-(5- to 10-membered heteroaryl)alkyl, \u2014S(O) 2 (aryl), \u2014S(O) 2 (alkyl), \u2014S(O) 2 (haloalkyl), \u2014OR 10 , \u2014SR 10 , or \u2014NR 10 R 11 ; R 7  and R 8  each independently represent hydrogen, hydroxyl, halo, nitro, alkyl, cycloalkyl, (cycloalkyl)alkyl, aryl, aralkyl, 5- to 10-membered heteroaryl, (5- to 10-membered heteroaryl)alkyl, (5- to 10-membered heterocyclyl)alkyl, 5- to 10-membered heterocyclyl, alkenyl, alkynyl, cyano, carboxyl, sulfate, amino, alkoxy, aryloxy, arylalkoxy, alkylamino, alkylthio, hydroxyalkyl, alkoxyalkyl, aminoalkyl, mercaptoalkyl, haloalkyl, ether group, thioether group, ester group, amido, thioester group, carbonate group, carbamate group, urea group, sulfonate group, sulfone group, sulfoxide group, sulfonamide group, acyl, acyloxy, or acylamino; or R 6 , R 7 , and R 8  taken together with a substituent on ring A and the intervening atoms, form an optionally substituted aryl, 5- to 10-membered heteroaryl, cycloalkyl, cycloalkenyl, 5- to 10-membered heterocyclyl, or (5- to 10-membered heterocyclyl)alkenyl; R 10  and R 11  are independently selected for each occurrence from hydrogen or substituted or unsubstituted alkyl, aralkyl, aryl, (5- to 10-membered heteroaryl)alkyl, 5- to 10-membered heteroaryl, (cycloalkyl)alkyl, cycloalkyl, (5- to 10-membered heterocyclyl)alkyl, 5- to 10-membered heterocyclyl, alkenyl, and alkynyl; and ring A represents an optionally substituted cycloalkyl, 5- to 10-membered heterocyclyl, cycloalkenyl, or (5- to 10-membered heterocyclyl)alkenyl, wherein each heteroaryl or heterocyclyl comprises 1 to 4 heteroatoms selected from N, O, and S; and wherein substituents on the alkyl, haloalkyl, alkenyl, alkynyl, aralkyl, aryl, (5- to 10-membered heteroaryl)alkyl, 5- to 10-membered heteroaryl, (cycloalkyl)alkyl, cycloalkyl, cycloalkenyl, (5- to 10-membered heterocyclyl)alkyl, 5- to 10-membered heterocyclyl, alkoxy, or amino are selected from halo, hydroxyl, carboxyl, alkoxycarbonyl, formyl, acyl, thioester group, thioacetate group, thioformate group, alkoxy, phosphate group, phosphonate group, phosphinate, amino, amido, amidine group, imine group, cyano, nitro, azido, sulfhydryl, mercaptoalkyl, sulfate group, sulfonate group, sulfamoyl, sulfonamido, sulfonyl, 5- to 10-membered heterocyclyl, aralkyl, aromatic group, and 5- to 10-membered heteroaromatic group.

Metadata:
- Claim Count in Document: 62.0
- Percentile: 97.0
- Lexical Diversity: 1.41463
- Patent Class: 540.0
- Transitional Phrase Type: open
- Component Type: 1
- Foreign Priority: False
- Related Applications: ['15081157', '14972475', '14514001', '16049434', '15366590']

Analysis Scores:
- 35 USC 101 Eligibility (BERT): 0.7184501386921772
- 35 USC 102 Novelty (BERT): 0.5847584501707004
- Combined Prediction Score: 0.7050809698400295
- Mean Citation Score: 435.802444
- Max Citation Score: 525.8457
- Similarity Product: 389.4983640842557

Labels:
- Claim Label 101: 1
- Claim Label 102: 1
- Claim Label 103: 1
- Claim Label 112: 0
- Combined Label: 1
- Label 101 Adjusted: 1

Dataset: test