# US 8,541,362 B2 · Cyclopropyl compounds and compositions for delivering active agents

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- Number: US 8,541,362 B2
- Document ID: US8541362B2
- Status: Granted
- Kind: B2
- Application number: 12/064,155
- Filed: 2006-08-21
- Published: 2009-09-03
- Granted: 2013-09-24
- Earliest claimed: 2005-08-19
- Assignees: Emisphere Technologies, Inc.
- Applicants: Pingwah Tang; Steven Dinh; Jongbin Lee; Puchun Liu; Gabriela Mustata
- Inventors: Pingwah Tang; Steven Dinh; Jongbin Lee; Puchun Liu; Gabriela Mustata
- Web page: https://patentgrep.com/patent/US8541362B2

## CPC

- C07C 233/05: having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07C 53/134: monocyclic
- C07C 57/26: containing rings other than six-membered aromatic rings
- C07C 59/13: containing rings
- C07C 233/06: having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C 233/09: with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
- C07C 233/58: having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C 233/65: having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C 235/14: having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C 323/60: with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
- C07C 2601/02: with a three-membered ring
- C07C 2601/14: The ring being saturated
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds and compositions for the delivery of active agents are provided. Methods of administration and preparation are provided as well.

## Claims

### Claim 1

A compound selected from:
and pharmaceutically acceptable salts thereof.

### Claim 2

A composition comprising:
(A) a biologically active agent; and
(B) at least one compound selected from
and pharmaceutically acceptable salts thereof.

### Claim 3 (depends on 2)

The composition of claim 2, wherein the biologically active agent comprises at least one protein, polypeptide, peptide, hormone, polysaccharide, mucopolysaccharide, carbohydrate, or lipid.

### Claim 4 (depends on 2)

The composition of claim 2, wherein the biologically active agent is selected from the group consisting of: BIBN-4096BS, growth hormones, human growth hormones recombinant human growth hormones (rhGH), bovine growth hormones, porcine growth hormones, growth hormone releasing hormones, growth hormone releasing factor, glucagon, interferons, α-interferon, β-interferon, γ-interferon, interleukin-1, interleukin-2, insulin, porcine insulin, bovine insulin, human insulin, human recombinant insulin, insulin-like growth factor (IGF), IGF-1, heparin, unfractionated heparin, heparinoids, dermatans, chondroitins, low molecular weight heparin, very low molecular weight heparin, ultra low molecular weight heparin, calcitonin, salmon calcitonin, eel calcitonin, human calcitonin; erythropoietin (EPO), atrial naturetic factor, antigens, monoclonal antibodies, somatostatin, protease inhibitors, adrenocorticotropin, gonadotropin releasing hormone, oxytocin, leutinizing-hormone-releasing-hormone, follicle stimulating hormone, glucocerebrosidase, thrombopoeitin, filgrastim, postaglandins, cyclosporin, vasopressin, cromolyn sodium, sodium chromoglycate, disodium chromoglycate, vancomycin, desferrioxamine (DFO), parathyroid hormone (PTH), fragments of PTH, glucagon-like peptide 1 (GLP-1), antimicrobials, anti-fungal agents, vitamins; and polyethylene glycol (PEG)-modified derivatives of these compounds; and any combination thereof.

### Claim 5 (depends on 2)

The composition of claim 2, wherein the biologically active agent comprises insulin, Leutenizing-hormone releasing hormone, GLP-1, heparin, Recombinant Human Growth Hormone, glucagon, Argatraban, and polyethylene glycol (PEG)-modified derivatives of these compounds; and any combination thereof.

### Claim 6 (depends on 2)

The composition of claim 2, wherein the biologically active agent comprises insulin.

### Claim 7 (depends on 2)

A dosage unit form comprising:
(A) the composition of claim 2; and
(B) (a) an excipient,
(b) a diluent,
(c) a disintegrant,
(d) a lubricant,
(e) a plasticizer,
(f) a colorant,
(g) a dosing vehicle, or
(h) any combination thereof.

### Claim 8 (depends on 7)

The dosage unit form of claim 7, wherein the biologically active agent comprises at least one protein, polypeptide, peptide, hormone, polysaccharide, mucopolysaccharide, carbohydrate, or lipid.

### Claim 9 (depends on 7)

The dosage unit form of claim 7, wherein the biologically active agent is selected from the group consisting of: Argatraban, BIBN-4096BS, growth hormones, human growth hormones (hGH), recombinant human growth hormones (rhGH), bovine growth hormones, porcine growth hormones, growth hormone releasing hormones, growth hormone releasing factor, interferons, glucagon, α-interferon, β-interferon, γ-interferon, interleukin-1, interleukin-2, insulin, porcine insulin, bovine insulin, human insulin, human recombinant insulin, insulin-like growth factor, insulin-like growth factor-1, heparin, unfractionated heparin, heparinoids, dermatans, chondroitins, low molecular weight heparin, very low molecular weight heparin, ultra low molecular weight heparin, calcitonin, salmon calcitonin, eel calcitonin, human calcitonin; erythropoietin, atrial naturetic factor, antigens, monoclonal antibodies, somatostatin, protease inhibitors, adrenocorticotropin, gonadotropin releasing hormone, oxytocin, leutinizing-hormone-releasing-hormone, follicle stimulating hormone, glucocerebrosidase, thrombopoeitin, filgrastim. postaglandins, cyclosporin, vasopressin, cromolyn sodium, sodium chromoglycate, disodium chromoglycate, vancomycin, desferrioxamine, parathyroid hormone, fragments of PTH, glucagon-like peptide 1 (GLP-1), antimicrobials, anti-fungal agents, vitamins; and polyethylene glycol-modified derivatives of these compounds; and any combination thereof.

### Claim 10 (depends on 7)

The dosage unit form of claim 7, wherein the biologically active agent comprises insulin, argatraban, LHRH, BIBN-4096BS, calcitonin, parathyroid hormone, erythropoietin, human growth hormones, glucagon or combinations thereof.

### Claim 11 (depends on 7)

The dosage unit form of claim 7, wherein the active agent comprises insulin.

### Claim 12 (depends on 7)

The dosage unit form of claim 7, wherein the active agent comprises glucagon.

### Claim 13 (depends on 7)

The dosage unit form of claim 7, wherein the dosage unit form comprises a dosing vehicle comprising a tablet, a capsule, a powder, or a liquid.

### Claim 14 (depends on 13)

The dosage unit form of claim 13, wherein the dosing vehicle is a liquid selected from the group consisting of water, 1,2-propane diol, ethanol, and any combination thereof.

### Claim 15 (depends on 2)

A method for administering a biologically-active agent to an animal in need of the agent, the method comprising administering orally to the animal a composition of claim 2.

### Claim 16

A method for preparing a composition comprising mixing:
(A) at least one biologically active agent;
(B) at least one compound selected from
and pharmaceutically acceptable salts thereof; and
(C) optionally, a dosing vehicle.

### Claim 17

A compound selected from
and pharmaceutically acceptable salts thereof.

### Claim 18

A composition comprising:
(A) a biologically active agent; and
(B) at least one compound selected from
and pharmaceutically acceptable salts thereof.