# US 10,307,403 B2 · Polymorphic forms and process

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 10,307,403 B2
- Document ID: US10307403B2
- Status: Granted
- Kind: B2
- Application number: 16/202,487
- Filed: 2018-11-28
- Published: 2019-04-25
- Granted: 2019-06-04
- Earliest claimed: 2015-12-18
- Assignees: Galecto Biotech AB
- Applicants: Galecto Biotech AB
- Inventors: Lise Gravelle; Anders Pedersen
- Web page: https://patentgrep.com/patent/US10307403B2

## 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 1 as identified in the following XRPD diffractogram peak list:
No.
Pos. [°2Th.]
Rel. Int. [%]
1
7.1269
77.72
2
7.5067
56
3
10.125
36.86
4
14.3791
32.28
5
15.0846
18.59
6
15.8201
35.78
7
16.7088
78.1
8
18.6001
21.29
9
19.7777
100
10
20.3353
57.04
11
21.7744
79.92
12
22.6053
35.8
13
23.4305
45.78
14
24.3658
51.03
15
25.8091
54.36
16
26.7046
25.38
17
29.028
16.19
18
30.2989
28.02
19
32.2693
14.86
20
33.5132
11.55
21
34.6078
11.54
22
35.8435
9.6
23
44.6257
22.73;
or
the polymorph has a polymorphic form 1 as identified in the XRPD diffractogram in FIG. 1.

### Claim 2 (depends on 1)

The polymorph of claim 1, wherein the polymorph is a hydrate.

### Claim 3 (depends on 2)

The polymorph of claim 2, wherein the hydrate contains 3-5% by weight water.

### 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 the polymorph of claim 1 comprising:
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 polymorphic form 1 by temperature cycling, crash cooling, 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 8)

The method of claim 8, 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.

### Claim 17 (depends on 5)

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 5 effective to treat said pulmonary fibrosis.