# US 10,369,136 B2 · Polymorphic forms and process

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- Number: US 10,369,136 B2
- Document ID: US10369136B2
- Status: Granted
- Kind: B2
- Application number: 16/062,206
- Filed: 2016-12-16
- Published: 2018-12-27
- Granted: 2019-08-06
- Earliest claimed: 2015-12-18
- Assignees: Galecto Biotech AB
- Applicants: Galecto Biotech AB
- Inventors: Lise Gravelle; Anders Pedersen
- Web page: https://patentgrep.com/patent/US10369136B2

## CPC

- A61K 31/4192: 1,2,3-Triazoles
- A61K 9/0073: {Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy; (nasal sprays A61K9/0043; inhalation of vapours of volatile or heated drugs, e.g. essential oils or nicotine, A61K9/007; devices A61M)}
- A61K 31/35: having six-membered rings with one oxygen as the only ring hetero atom
- A61K 31/70: Carbohydrates; Sugars; Derivatives thereof (sorbitol A61K31/047)
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 11/00: Drugs for disorders of the respiratory system
- C07H 1/00: Processes for the preparation of sugar derivatives
- C07H 19/056: Triazole or tetrazole radicals
- 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
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

The present invention relates to a polymorph of a compound of formula (I) This polymorph is particularly suitable in treating IPF by pulmonary administration.

## Claims

### Claim 1

A polymorph of a compound of formula (I)
wherein the polymorph is 3,3′-Dideoxy-3,3′-bis-[4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl]-1,1′-sulfanediyl-di-β-D-galactopyranoside and wherein:
the polymorph has a polymorphic form selected from the group consisting of a polymorphic form 2 as identified in the XRPD diffractogram in FIG. 3, a polymorphic form 3 as identified in the XRPD diffractogram in FIG. 4, a polymorphic form 4 as identified in the XRPD diffractogram in FIG. 5, a polymorphic form 5 as identified in the XRPD diffractogram in FIG. 6, and a polymorphic form 6 as identified in the XRPD diffractogram in FIG. 7.

### Claim 2 (depends on 1)

The polymorph of claim 1 wherein the compound of formula (I) is 3,3′-Dideoxy-3,3′-bis-[4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl]-1,1′-sulfanediyl-di-β-D-galactopyranoside as a hydrate and the polymorphic form is selected from the group consisting of polymorphic form 2, polymorphic form 5, and polymorphic form 6.

### Claim 3 (depends on 2)

The polymorph of claim 2 wherein the 3,3′-Dideoxy-3,3′-bis-[4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl]-1,1′-sulfanediyl-di-β-D-galactopyranoside hydrate contains 3-5% water (weight %).

### Claim 4 (depends on 1)

The polymorph of claim 1 wherein the polymorph is micronized.

### Claim 5 (depends on 4)

The polymorph of claim 4 wherein the polymorph is micronized to a size that can reach the bronchioles and/or the alveoli of the human.

### Claim 6 (depends on 1)

A pharmaceutical composition comprising the polymorph of claim 1, and optionally a pharmaceutically acceptable additive.

### Claim 7 (depends on 1)

A process of making a polymorph of claim 1 comprising the steps of suspending or dissolving 3,3′-Dideoxy-3,3′-bis-[4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl]-1,1′-sulfanediyl-di-β-D-galactopyranoside in an organic solvent and then making the polymorph by temperature cycling, crash cooling, anti-solvent addition, evaporation, or a combination thereof.

### Claim 8 (depends on 1)

A method for treatment of pulmonary fibrosis in a human comprising administering to the lung tissue of the human an amount of the polymorph of claim 1 effective to treat said pulmonary fibrosis.

### Claim 9 (depends on 1)

The method of claim 1 wherein the administration is carried out by a dry powder inhaler.

### Claim 10 (depends on 9)

The method of claim 9 wherein the administration is carried out by a monodose dry powder inhaler.

### Claim 11 (depends on 8)

The method of claim 8 wherein the polymorph is administered to the bronchioles and/or the alveoli of the human.

### Claim 12 (depends on 8)

The method of claim 8 wherein the amount is a once daily amount from 0.15 mg to 50 mg.

### Claim 13 (depends on 12)

The method of claim 12, wherein the amount is a once daily amount selected from the group consisting of: 0.15 mg to 0.50 mg, 0.50 mg to 0.75 mg, 0.75 mg to 1.25 mg, 1.25 mg to 1.5 mg, 1.5 mg to 1.75 mg, 1.75 mg to 2 mg, 2 mg to 2.25 mg, 2.25 mg to 2.5 mg, 2.5 mg to 2.75 mg, 2.75 mg to 3 mg, 3 mg to 5 mg, 5 mg to 7 mg, 7 mg to 8 mg, 8 mg to 10 mg, 10 mg to 20 mg and 20 mg to 50 mg.

### Claim 14 (depends on 2)

A method for treatment of pulmonary fibrosis in a human comprising administering to the lung tissue of the human an amount of the polymorph of claim 2 effective to treat said pulmonary fibrosis.

### Claim 15 (depends on 3)

A method for treatment of pulmonary fibrosis in a human comprising administering to the lung tissue of the human an amount of the polymorph of claim 3 effective to treat said pulmonary fibrosis.

### Claim 16 (depends on 4)

A method for treatment of pulmonary fibrosis in a human comprising administering to the lung tissue of the human an amount of the polymorph of claim 4 effective to treat said pulmonary fibrosis.