# US 2023/0057084 A1 · PROCESSES FOR THE PREPARATION OF (3S,4R)-3-ETHYL-4-(3H-IMIDAZO[1,2-a]PYRROLO[2,3-e]-PYRAZIN-8-YL)-N-(2,2,2-TRIFLUOROETHYL)PYRROLIDINE-1-CARBOXAMIDE AND SOLID STATE FORMS THEREOF

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- Number: US 2023/0057084 A1
- Document ID: US20230057084A1
- Status: Published application
- Kind: A1
- Application number: 17/951,332
- Filed: 2022-09-23
- Published: 2023-02-23
- Earliest claimed: 2015-10-16
- Assignees: AbbVie Inc.
- Applicants: AbbVie Inc.
- Inventors: Ayman Allian; Jayanthy Jayanth; Mohamed-Eslam F. Mohamed; Mathew M. Mulhern; Fredrik Lars Nordstrom; Ahmed A. Othman; Michael J. Rozema; Lakshmi Bhagavatula; Patrick J. Marroum; Peter T. Mayer; Ahmad Y. Sheikh; Thomas B. Borchardt; Ben Klünder
- Web page: https://patentgrep.com/patent/US20230057084A1

## CPC

- C07D 487/14: Ortho-condensed systems
- A61K 9/0053: {Mouth and digestive tract, i.e. intraoral and peroral administration}
- A61K 31/4985: Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
- A61K 47/02: Inorganic compounds
- A61K 47/12: Carboxylic acids; Salts or anhydrides thereof
- A61K 47/38: Cellulose; Derivatives thereof
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 7/00: Drugs for disorders of the blood or the extracellular fluid
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/06: Antipsoriatics
- A61P 17/14: for baldness or alopecia
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 35/00: Antineoplastic agents
- A61P 37/02: Immunomodulators
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C04B 35/62873: {Carbon}
- C04B 35/62886: {by wet chemical techniques}
- C04B 35/64: Burning or sintering processes (C04B33/32 takes precedence {; powder metallurgy B22F})
- C04B 35/657: for manufacturing refractories (C04B35/05, C04B35/107, C04B35/484 take precedence)
- C04B 35/83: Carbon fibres in a carbon matrix
- C07D 487/04: Ortho-condensed systems
- C04B 2235/422: Carbon
- C04B 2235/48: Organic compounds becoming part of a ceramic after heat treatment, e.g. carbonising phenol resins
- C04B 2235/5248: Carbon, e.g. graphite
- C04B 2235/5256: Two-dimensional, e.g. woven structures
- C04B 2235/616: Liquid infiltration of green bodies or pre-forms
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C04B: LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE {(roofing granules E04D7/005)}; CERAMICS (devitrified glass-ceramics C03C10/00); REFRACTORIES; TREATMENT OF NATURAL STONE
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The present disclosure relates to processes for preparing (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide, solid state forms thereof, and corresponding pharmaceutical compositions, methods of treatment (including treatment of rheumatoid arthritis), kits, methods of synthesis, and products-by-process.

## Claims

### Claim at position 1

1-116. (canceled)

### Claim 117

Crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide.

### Claim 118 (depends on 117)

The crystalline freebase of claim 117, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is an anhydrate.

### Claim 119 (depends on 117)

The crystalline freebase of claim 117, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is a hydrate.

### Claim 120 (depends on 119)

The crystalline freebase of claim 119, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is a hemihydrate.

### Claim 121 (depends on 117)

The crystalline freebase of claim 117, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is a solvate.

### Claim 122

A pharmaceutical composition comprising crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and a pharmaceutically acceptable carrier.

### Claim 123 (depends on 122)

The pharmaceutical composition of claim 122, wherein the pharmaceutical composition is a solid dosage form.

### Claim 124 (depends on 123)

The pharmaceutical composition of claim 123, wherein the solid dosage form is a tablet.

### Claim 125 (depends on 122)

The pharmaceutical composition of claim 122, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is an anhydrate.

### Claim 126 (depends on 125)

The pharmaceutical composition of claim 125, wherein the pharmaceutical composition is a solid dosage form.

### Claim 127 (depends on 122)

The pharmaceutical composition of claim 122, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is a hydrate.

### Claim 128 (depends on 127)

The pharmaceutical composition of claim 127, wherein the pharmaceutical composition is a solid dosage form.

### Claim 129 (depends on 122)

The pharmaceutical composition of claim 122, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is a hemihydrate.

### Claim 130 (depends on 129)

The pharmaceutical composition of claim 129, wherein the pharmaceutical composition is a solid dosage form.

### Claim 131 (depends on 122)

The pharmaceutical composition of claim 122, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is a solvate.

### Claim 132 (depends on 131)

The pharmaceutical composition of claim 131, wherein the pharmaceutical composition is a solid dosage form.

### Claim 133

A process for preparing a pharmaceutical composition comprising crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and a pharmaceutically acceptable carrier, the process comprising combining crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and a pharmaceutically acceptable carrier.

### Claim 134 (depends on 133)

The process of claim 133, wherein the pharmaceutical composition is a solid dosage form.

### Claim 135 (depends on 134)

The process of claim 134, wherein the solid dosage form is a tablet.

### Claim 136 (depends on 133)

The process of claim 133, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is an anhydrate.

### Claim 137 (depends on 136)

The process of claim 136, wherein the pharmaceutical composition is a solid dosage form.

### Claim 138 (depends on 133)

The process of claim 133, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is a hydrate.

### Claim 139 (depends on 138)

The process of claim 138, wherein the pharmaceutical composition is a solid dosage form.

### Claim 140 (depends on 133)

The process of claim 133, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is a hemihydrate.

### Claim 141 (depends on 140)

The process of claim 140, wherein the pharmaceutical composition is a solid dosage form.

### Claim 142 (depends on 133)

The process of claim 133, wherein the crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide is a solvate.

### Claim 143 (depends on 142)

The process of claim 142, wherein the pharmaceutical composition is a solid dosage form.

### Claim 144 (depends on 133)

A pharmaceutical composition comprising crystalline freebase (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and a pharmaceutically acceptable carrier, prepared by the process of claim 133.

### Claim 145 (depends on 144)

The pharmaceutical composition of claim 144, wherein the pharmaceutical composition is a solid dosage form.

### Claim 146 (depends on 144)

The pharmaceutical composition of claim 144, wherein the solid dosage form is a tablet.