# US 9,040,532 B2 · Alpha adrenergic receptor modulators

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- Number: US 9,040,532 B2
- Document ID: US9040532B2
- Status: Granted
- Kind: B2
- Application number: 13/500,501
- Filed: 2010-10-06
- Published: 2012-08-16
- Granted: 2015-05-26
- Earliest claimed: 2009-10-06
- Assignees: Allergan, Inc.
- Applicants: Ken Chow; Liming Wang; Wenkui K. Fang; Evelyn G. Corpuz; Santosh C. Sinha; Daniel W. Gil; Mohammad I. Dibas; John E. Donello
- Inventors: Ken Chow; Liming Wang; Wenkui K. Fang; Evelyn G. Corpuz; Santosh C. Sinha; Daniel W. Gil; Mohammad I. Dibas; John E. Donello
- Web page: https://patentgrep.com/patent/US9040532B2

## CPC

- A61K 31/498: Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
- A61K 31/40: having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K 31/4025: not condensed and containing further heterocyclic rings, e.g. cromakalim
- A61K 31/404: Indoles, e.g. pindolol
- A61K 31/4184: condensed with carbocyclic rings, e.g. benzimidazoles
- A61K 31/435: having six-membered rings with one nitrogen as the only ring hetero atom
- A61K 31/437: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A61K 31/4375: the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
- A61K 31/4709: Non-condensed quinolines and containing further heterocyclic rings
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/06: Antipsoriatics
- A61P 17/10: Anti-acne agents
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 27/02: Ophthalmic agents
- A61P 27/06: Antiglaucoma agents or miotics
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C07D 207/22: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D 417/12: linked by a chain containing hetero atoms as chain links
- C07D 471/04: Ortho-condensed systems
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Compounds are described herein useful for treating diseases and conditions by modulation of one or more alpha adrenergic receptor. The compounds can include a naphthalene, a quinoline, a benzoimidazole or an isoquinoline as a core structure. Methods of making, using and formulating these compounds are described.

## Claims

### Claim 1

A compound having formula I, its enantiomers, diastereoisomers, tautomers or a pharmaceutically acceptable salt thereof
wherein:
n is 0 or 1;
A is an aromatic or non-aromatic ring;
X is N, N—R1, CH—R1, C—R1;
R1 is H, C1-6 alkyl or halogen;
R2 is N, N—R3, CH—R3, C—R3, O or S;
R3 is H, halogen, or C1-6 alkyl;
R4 is halogen, H, C1-6 alkyl or part of a ring as a S, O, N or as a C;
R5 is a S, N or is a C and is always part of a ring;
R6 is H, C1-6 alkyl, halogen or is part of a ring as a S, O, N or as a C;
R4 and R5 can form a 5 or 6 membered carbo- or heterocyclic ring, aromatic or non-aromatic, optionally substituted with 1 to 2 C1-6 alkyl or with 1 to 2 halogen and is directly attached to the rest of the molecule; or
R5 and R6 can form a 5 or 6 membered carbo- or heterocyclic ring, aromatic or non-aromatic, optionally substituted with 1 to 2 C1-6 alkyl or 1 to 2 halogen and is directly attached to the rest of the molecule;
except (+/−) 3,4-dihydro-N-(1,2,3,4-tetrahydro-1-naphthalenyl)-2H-pyrrol-5-amine.

### Claim 2 (depends on 1)

A compound according to claim 1 of formula II
wherein:
n is 1;
A is an aromatic ring;
X is C—R1;
R1 is H;
R2 is N or C—R3;
R3 is H, halogen, or C1-6 alkyl;
R4 is part of a ring as a S, O, N or as a C;
R5 is a N or is a C and is always part of a ring;
R6 is H, C1-6 alkyl or halogen; and
R4 and R5 form a 5 or 6 membered carbo- or heterocyclic ring, aromatic or non-aromatic, optionally substituted with 1 to 2 C1-6 alkyl or 1 to 2 halogen and is directly attached to the rest of the molecule.

### Claim 3 (depends on 1)

A compound according to claim 1 of formula III
wherein:
n is 1;
A is an aromatic ring;
X is C—R1;
R1 is H, C1-3 alkyl
R2 is N or C—R3,
R3 is H, halogen, or C1-6 alkyl;
R4 is halogen or H;
R5 is a N or C and is always part of a ring;
R6 is part of a ring as a N or as a C;
R5 and R6 form a 5 or 6 membered carbo- or heterocyclic ring, aromatic or non-aromatic, optionally substituted with 1 to 2 C1-6 alkyl or 1 to 2 halogen and is directly attached to the rest of the molecule.

### Claim 4 (depends on 1)

A compound according to claim 1 of formula IV
wherein:
n is 0;
A is a non-aromatic ring;
R2 is CH—R3;
R3 is H;
R4 is H;
R5 is C and is always part of a ring;
R6 is part of a ring as a C; and
R5 and R6 form a 6 membered aromatic carbocyclic ring directly attached to the rest of the molecule.

### Claim 5 (depends on 1)

A compound according to claim 1 of formula V
wherein
n is 1;
A is a non-aromatic ring;
X is CH—R1;
R1 is H;
R2 is CH—R3;
R3 is H;
R4 is H;
R5 is C and is always part of a ring;
R6 is part of a ring as a C; and
R5 and R6 form a 6 membered aromatic carbocyclic ring, optionally substituted with C1-6 alkyl or halogen and is directly attached to the rest of the molecule;
except (+/−) 3,4-dihydro-N-(1,2,3,4-tetrahydro-1-naphthalenyl)-2H-pyrrol-5-amine.

### Claim 6 (depends on 1)

A compound according to claim 1 selected from the group consisting of:
N-1-Naphthyl-3,4-dihydro-2H-pyrrol-5-amine;
N-(2-Methyl-1-naphthyl)-3,4-dihydro-2H-pyrrol-5-amine;
N-(4-Bromo-1-naphthyl)-3,4-dihydro-2H-pyrrol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-1H-benzimidazol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-6,7-dihydro-5H-cyclopenta[b]pyridin-3-amine;
4-Chloro-N-[(2E)-pyrrolidin-2-ylidene]-1,5-naphthyridin-3-amine;
N-(4-Chloro-1-naphthyl)-3,4-dihydro-2H-pyrrol-5-amine fumarate;
N-(4-Chloro-1-naphthyl)-3,4-dihydro-2H-pyrrol-5-amine;
5-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)quinoxalin-6-amine fumarate;
5-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)quinoxalin-6-amine;
8-Chloro-N-(3,4-dihydro-2H-pyrrol-5-yl)quinolin-7-amine;
4-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)-1H-benzimidazol-5-amine;
4-Chloro-N-(3,4-dihydro-2H-pyrrol-5-yl)-1H-benzimidazol-5-amine;
N-(3,4-dihydro-2H-pyrrol-5-yl)-4-methyl-1H-benzimidazol-5-amine;
7-Chloro-N-(3,4-dihydro-2H-pyrrol-5-yl)-1H-benzimidazol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)quinoxalin-6-amine;
N-(5,6,7,8-Tetrahydronaphthalen-2-yl)-3,4-dihydro-2H-pyrrol-5-amine;
N-(2,3-Dihydro-1H-inden-4-yl)-3,4-dihydro-2H-pyrrol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-1H-indol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-4-methyl-1H-indol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-7-methyl-1H-indol-5-amine;
7-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)-1H-indol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-1H-indol-6-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-1H-indol-7-amine;
N-1-Benzothien-5-yl-3,4-dihydro-2H-pyrrol-5-amine;
N-1-Benzofuran-5-yl-3,4-dihydro-2H-pyrrol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-1H-indol-4-amine;
N-[(2E)-Pyrrolidin-2-ylidene]-1H-pyrrolo[2,3-b]pyridin-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-5-methylquinoxalin-6-amine fumarate;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-5-methylquinoxalin-6-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)quinolin-7-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-8-methylquinolin-7-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-8-methylquinolin-7-amine fumarate;
N-(3,4-dihydro-2H-pyrrol-5-yl)quinolin-8-amine;
4-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)-1,3-benzothiazol-5-amine fumarate;
4-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)-1,3-benzothiazol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)isoquinolin-8-amine fumarate;
N-(3,4-Dihydro-2H-pyrrol-5-yl)isoquinolin-8-amine;
N-[(1S)-2,3-Dihydro-1H-inden-1-yl]-3,4-dihydro-2H-pyrrol-5-amine;
N-[(1S)-1,2,3,4-Tetrahydronaphthalen-1-yl]-3,4-dihydro-2H-pyrrol-5-amine;
N-(7-Fluoro-2,3-dihydro-1H-inden-1-yl)-3,4-dihydro-2H-pyrrol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-5-methyl-3,4-dihydro-2H-1,4-benzoxazin-6-amine;
N-[(1S)-4-Methyl-2,3-dihydro-1H-inden-1-yl]-3,4-dihydro-2H-pyrrol-5-amine;
4-Methyl-N-[(2E)-pyrrolidin-2-ylidene]-1H-pyrrolo[2,3-b]pyridin-5-amine.

### Claim 7 (depends on 1)

A compound according to claim 1 selected from the group consisting of:
N-1-Naphthyl-3,4-dihydro-2H-pyrrol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-1H-benzimidazol-5-amine;
4-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)-1H-benzimidazol-5-amine;
N-(5,6,7,8-Tetrahydronaphthalen-2-yl)-3,4-dihydro-2H-pyrrol-5-amine;
N-(2,3-Dihydro-1H-inden-4-yl)-3,4-dihydro-2H-pyrrol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-1H-indol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-4-methyl-1H-indol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-7-methyl-1H-indol-5-amine;
7-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)-1H-indol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-1H-indol-6-amine;
N-1-Benzothien-5-yl-3,4-dihydro-2H-pyrrol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-1H-indol-4-amine;
N-[(2E)-Pyrrolidin-2-ylidene]-1H-pyrrolo[2,3-b]pyridin-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-5-methylquinoxalin-6-amine fumarate;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-5-methylquinoxalin-6-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)quinolin-7-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-8-methylquinolin-7-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-8-methylquinolin-7-amine fumarate;
4-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)-1,3-benzothiazol-5-amine fumarate;
4-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)-1,3-benzothiazol-5-amine;
N-[(1S)-2,3-Dihydro-1H-inden-1-yl]-3,4-dihydro-2H-pyrrol-5-amine;
N-[(1S)-1,2,3,4-Tetrahydronaphthalen-1-yl]-3,4-dihydro-2H-pyrrol-5-amine.

### Claim 8 (depends on 1)

A compound according to claim 1 selected from the group consisting of:
4-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)-1H-benzimidazol-5-amine;
N-(5,6,7,8-Tetrahydronaphthalen-2-yl)-3,4-dihydro-2H-pyrrol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-1H-indol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-4-methyl-1H-indol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-7-methyl-1H-indol-5-amine;
7-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)-1H-indol-5-amine;
N-1-Benzothien-5-yl-3,4-dihydro-2H-pyrrol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-8-methylquinolin-7-amine fumarate;
4-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)-1,3-benzothiazol-5-amine fumarate;
4-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)-1,3-benzothiazol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-8-methylquinolin-7-amine.

### Claim 9

A pharmaceutical composition comprising at least one compound of having formula I:
wherein:
n is 0 or 1;
A is an aromatic or non-aromatic ring;
X is N, N—R1, CH—R1, C—R1;
R1 is H, C1-6 alkyl or halogen;
R2 is N, N—R3, CH—R3, C—R3, O or S;
R3 is H, halogen, or C1-6 alkyl;
R4 is halogen, H, C1-6 alkyl or part of a ring as a S, O, N or as a C;
R5 is a S, N or is a C and is always part of a ring;
R6 is H, C1-6 alkyl, halogen or is part of a ring as a S, O, N or as a C;
R4 and R5 can form a 5 or 6 membered carbo- or heterocyclic ring, aromatic or non-aromatic, optionally substituted with 1 to 2 C1-6 alkyl or with 1 to 2 halogen and is directly attached to the rest of the molecule; or
R5 and R6 can form a 5 or 6 membered carbo- or heterocyclic ring, aromatic or non-aromatic, optionally substituted with 1 to 2 C1-6 alkyl or 1 to 2 halogen and is directly attached to the rest of the molecule;
except (+/−) 3,4-dihydro-N-(1,2,3,4-tetrahydro-1-naphthalenyl)-2H-pyrrol-5-amine;
and a pharmaceutically acceptable carrier.

### Claim 10 (depends on 9)

The pharmaceutical composition of claim 9, comprising at least one compound of formula II:
wherein:
n is 1;
A is an aromatic ring;
X is C—R1;
R1 is H;
R2 is N or C—R3;
R3 is H, halogen, or C1-6 alkyl;
R4 is part of a ring as a S, O, N or as a C;
R5 is a N or is a C and is always part of a ring;
R6 is H, C1-6 alkyl or halogen; and
R4 and R5 form a 5 or 6 membered carbo- or heterocyclic ring, aromatic or non-aromatic, optionally substituted with 1 to 2 C1-6 alkyl or 1 to 2 halogen and is directly attached to the rest of the molecule.

### Claim 11 (depends on 9)

The pharmaceutical composition of claim 9, comprising at least one compound of formula III:
wherein:
n is 1;
A is an aromatic ring;
X is C—R1;
R1 is H, C1-3 alkyl;
R2 is N or C—R3, R3 is H, halogen, or C1-6 alkyl;
R4 is halogen or H;
R5 is a N or C and is always part of a ring;
R6 is part of a ring as a N or as a C;
R5 and R6 form a 5 or 6 membered carbo- or heterocyclic ring, aromatic or non-aromatic, optionally substituted with 1 to 2 C1-6 alkyl or 1 to 2 halogen and is directly attached to the rest of the molecule.

### Claim 12 (depends on 9)

The pharmaceutical composition of claim 9, comprising at least one compound of formula IV:
wherein:
n is 0;
A is a non-aromatic ring;
R2 is CH—R3;
R3 is H;
R4 is H;
R5 is C and is always part of a ring;
R6 is part of a ring as a C; and
R5 and R6 form a 6 membered aromatic carbocyclic ring directly attached to the rest of the molecule.

### Claim 13 (depends on 9)

The pharmaceutical composition of claim 9, comprising at least one compound of formula V:
wherein
n is 1;
A is a non-aromatic ring;
X is CH—R1;
R1 is H;
R2 is CH—R3;
R3 is H;
R4 is H;
R5 is C and is always part of a ring;
R6 is part of a ring as a C; and
R5 and R6 form a 6 membered aromatic carbocyclic ring, optionally substituted with C1-6 alkyl or halogen and is directly attached to the rest of the molecule;
except (+/−) 3,4-dihydro-N-(1,2,3,4-tetrahydro-1-naphthalenyl)-2H-pyrrol-5-amine.

### Claim 14 (depends on 9)

The pharmaceutical composition of claim 9, comprising at least one compound selected from the group consisting of:
N-1-Naphthyl-3,4-dihydro-2H-pyrrol-5-amine;
N-(2-Methyl-1-naphthyl)-3,4-dihydro-2H-pyrrol-5-amine;
N-(4-Bromo-1-naphthyl)-3,4-dihydro-2H-pyrrol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-1H-benzimidazol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-6,7-dihydro-5H-cyclopenta[b]pyridin-3-amine;
4-Chloro-N-[(2E)-pyrrolidin-2-ylidene]-1,5-naphthyridin-3-amine;
N-(4-Chloro-1-naphthyl)-3,4-dihydro-2H-pyrrol-5-amine fumarate;
N-(4-Chloro-1-naphthyl)-3,4-dihydro-2H-pyrrol-5-amine;
5-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)quinoxalin-6-amine fumarate;
5-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)quinoxalin-6-amine;
8-Chloro-N-(3,4-dihydro-2H-pyrrol-5-yl)quinolin-7-amine;
4-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)-1H-benzimidazol-5-amine;
4-Chloro-N-(3,4-dihydro-2H-pyrrol-5-yl)-1H-benzimidazol-5-amine;
N-(3,4-dihydro-2H-pyrrol-5-yl)-4-methyl-1H-benzimidazol-5-amine;
7-Chloro-N-(3,4-dihydro-2H-pyrrol-5-yl)-1H-benzimidazol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)quinoxalin-6-amine;
N-(5,6,7,8-Tetrahydronaphthalen-2-yl)-3,4-dihydro-2H-pyrrol-5-amine;
N-(2,3-Dihydro-1H-inden-4-yl)-3,4-dihydro-2H-pyrrol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-1H-indol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-4-methyl-1H-indol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-7-methyl-1H-indol-5-amine;
7-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)-1H-indol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-1H-indol-6-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-1H-indol-7-amine;
N-1-Benzothien-5-yl-3,4-dihydro-2H-pyrrol-5-amine;
N-1-Benzofuran-5-yl-3,4-dihydro-2H-pyrrol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-1H-indol-4-amine;
N-[(2E)-Pyrrolidin-2-ylidene]-1H-pyrrolo[2,3-b]pyridin-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-5-methylquinoxalin-6-amine fumarate;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-5-methylquinoxalin-6-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)quinolin-7-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-8-methylquinolin-7-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-8-methylquinolin-7-amine fumarate;
N-(3,4-dihydro-2H-pyrrol-5-yl)quinolin-8-amine;
4-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)-1,3-benzothiazol-5-amine fumarate;
4-Bromo-N-(3,4-dihydro-2H-pyrrol-5-yl)-1,3-benzothiazol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)isoquinolin-8-amine fumarate;
N-(3,4-Dihydro-2H-pyrrol-5-yl)isoquinolin-8-amine;
N-[(1S)-2,3-Dihydro-1H-inden-1-yl]-3,4-dihydro-2H-pyrrol-5-amine;
N-[(1S)-1,2,3,4-Tetrahydronaphthalen-1-yl]-3,4-dihydro-2H-pyrrol-5-amine;
N-(7-Fluoro-2,3-dihydro-1H-inden-1-yl)-3,4-dihydro-2H-pyrrol-5-amine;
N-(3,4-Dihydro-2H-pyrrol-5-yl)-5-methyl-3,4-dihydro-2H-1,4-benzoxazin-6-amine;
N-[(1S)-4-Methyl-2,3-dihydro-1H-inden-1-yl]-3,4-dihydro-2H-pyrrol-5-amine;
4-Methyl-N-[(2E)-pyrrolidin-2-ylidene]-1H-pyrrolo[2,3-b]pyridin-5-amine.