# US 11,306,090 B2 · Azabicyclo and diazepine derivatives

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- Number: US 11,306,090 B2
- Document ID: US11306090B2
- Status: Granted
- Kind: B2
- Application number: 16/760,192
- Filed: 2018-11-02
- Published: 2021-06-17
- Granted: 2022-04-19
- Earliest claimed: 2017-11-03
- Assignees: Alcon Inc.
- Applicants: Alcon Inc.
- Inventors: David Ellis; Howard Allen Ketelson
- Web page: https://patentgrep.com/patent/US11306090B2

## CPC

- C07D 471/08: Bridged systems
- A61K 9/0048: {Eye, e.g. artificial tears}
- A61P 27/10: for accommodation disorders, e.g. myopia
- C07D 243/38: [b, e]- or [b, f]-condensed with six-membered rings
- C07D 451/10: acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine
- C07D 471/04: Ortho-condensed systems
- 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

## Abstract

The present invention provides in one aspect azabicyclo and diazepine derivatives useful as modulators of muscarinic receptors. In another aspect, the present invention provides pharmaceutical compositions for treating ocular diseases, the compositions comprising at least one muscarinic receptor modulator.

## Claims

### Claim 1

A compound or a pharmaceutically acceptable salt thereof, wherein the compound is presented by formula (I):
wherein
Me=CH3;
A=NR5;
X=—OH, —O—Y—Z, —S—Y—Z, or —NR5—Y—Z;
R1 and R2 are independently H, D, hydroxyl, alkoxy, nitrile, halogen atoms, C1-C20 straight, branched or cyclo alkyl groups optionally substituted with halogen atoms; or
R1 and R2 are independently phenyl or benzyl groups being optionally substituted with one or more substituents selected from C1-C20 straight, branched or cyclo alkyl groups, halo alkyl groups, hydroxyl, alkoxy, nitrile, nitro, amino, amide, ester, sulfone, sulfoxide, sulfonamide, and halogen atoms; or
R1 and R2 are independently a heterocyclic saturated, unsaturated or aromatic 5- or 6-member ring containing one or more heteroatoms selected from nitrogen, oxygen and sulfur and being optionally substituted with one or more substituents selected from C1-C20 straight, branched or cyclo alkyl, halo alkyl groups, hydroxyl, alkoxy, nitrile, nitro, amino, amide, ester, sulfone, sulfoxide or halogen atoms;
R3 and R4 are independently hydrogen, C1-C10 straight or branched or cyclo alkyl or halo alkyl groups or
R3 and R4 can combine to form 3- to 6-membered rings;
R5═H, a C1-C20 straight or branched alkyl groups, or a C1-C10 straight or branched haloalkyl groups;
Y is a bivalent radical having the following meaning:
a) Straight or branched C1-C20 alkyl, being optionally substituted with one or more of the substituents selected from the group consisting of: halogen atoms and hydroxyl;
b) —C(O)(C1-C10 alkyl)- or —C(O)(CH2)nC(O)O—(C1-C10 alkyl)- or —(C1-C10 alkyl)-;
c)
d)
e)
or
f)
wherein n is an integer from 0 to 20;
R6 and R7 are independently H or C1-C10, straight or branched alkyl groups, C1-C10 straight or branched haloalkyl groups; or
R6 and R7 can combine to form 3- to 6-membered rings; and
Z is H, —OH, C1-6 alkoxy, —COOH, —NR8R9;
R8 and R9 are independently C1-C20 alkyl, being optionally substituted with one or more substituents selected from hydroxyl, amino, ester, carboxylic acid, and halogen atoms; or
R8 and R9 can combine to form 3- to 6-membered rings containing one or more heteroatoms which are selected from the group consisting of:

### Claim 2 (depends on 1)

The compound or the pharmaceutically acceptable salt thereof according to claim 1, wherein the compound is

### Claim 3 (depends on 1)

A pharmaceutical composition comprising: (1) a compound of claim 1 and/or a pharmaceutically acceptable salt thereof; and (2) one or more pharmaceutically acceptable carriers.

### Claim 4 (depends on 3)

The composition according to claim 3, wherein said composition is a topical composition.

### Claim 5 (depends on 3)

The composition according to claim 3, wherein said composition is an ophthalmically compatible composition.

### Claim 6 (depends on 5)

The composition according to claim 5, wherein said composition is a topical composition.

### Claim 7 (depends on 5)

The composition according to claim 5, wherein said composition comprises a therapeutically effective amount of said compound, and/or said pharmaceutically acceptable salt.

### Claim 8 (depends on 7)

The composition according to claim 7, wherein said composition is a topical composition.

### Claim 9 (depends on 5)

The composition according to claim 5, wherein said composition comprises from about 0.01 to about 10.0 weight percent of said compound and/or said pharmaceutically acceptable salt.

### Claim 10 (depends on 9)

The composition according to claim 9, wherein said composition is a topical composition.

### Claim 11 (depends on 5)

The composition according to claim 5, wherein said composition comprises: from about 0.01 percent weight/volume to about 5 weight/volume percent of said compound and/or said pharmaceutically acceptable salt; or from about 0.1 to 5.0 weight percent of said compound and/or said pharmaceutically acceptable salt.

### Claim 12 (depends on 11)

The composition according to claim 11, wherein said composition is a topical composition.

### Claim 13 (depends on 1)

A combination comprising: (1) a therapeutically effective amount of a compound according to claim 1 and/or a pharmaceutically acceptable salt thereof; and (2) one or more therapeutically active agents.

### Claim 14 (depends on 1)

A method of treating a mammalian subject having or at risk of having an ocular disorder, said method comprising administering to the subject an effective amount of: (a) a compound according to claim 1 and/or (b) a pharmaceutically acceptable salt thereof.