IP Library Granted Patent US 10,259,812
Granted Patent B2
US 10,259,812 · App. 15/708,424 · Granted Apr 16, 2019

CGRP receptor antagonists

Inventors: John Andrew Christopher (Welwyn Garden, GB); Miles Stuart Congreve (Welwyn Garden, GB); Sarah Joanne Bucknell (Welwyn Garden, GB); Francesca Deflorian (Welwyn Garden, GB); Mark Pickworth (Welwyn Garden, GB); Jonathan Stephen Mason (Welwyn Garden, GB)
Assignee: Heptares Therapeutics Limited
C07D471/10
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Quick Facts
Patent No.
US 10,259,812
App. No.
15/708,424
Granted
Apr 16, 2019
Kind
B2
Abstract

The disclosures herein relate to novel compounds of formula wherein R 1 , R 2 and R 3 are as defined herein, and their use in treating, preventing, ameliorating, controlling or reducing cerebrovascular or vascular disorders associated with CGRP receptor function.

Claims (31)

1. A method for treating a cerebrovascular or vascular disorder in a subject comprising administering to the subject a compound of formula (I)

or a salt thereof, wherein R 1 is

R 2 is H or forms a spirocyclic heterocyclic ring with R 3 ;

R 3 forms a spirocyclic heterocyclic ring with R 2 or is a heterocyclic ring if R 2 is H,

wherein the cerebrovascular or vascular disorder is migraine without aura, chronic migraine, pure menstrual migraine, menstrually-related migraine, migraine with aura, familial hemiplegic migraine, sporadic hemiplegic migraine, basilar-type migraine, cyclical vomiting, abdominal migraine, benign paroxysmal vertigo of childhood, retinal migraine, status migrainosus, cluster headache, dialysis headache, paroxysmal hemicrania, osteoarthritis, hot flashes associated with menopause or medically induced menopause due to surgery or drug treatment, hemicrania continua, cyclic vomiting syndrome, rosacea or joint pain associated with osteoarthritis and rheumatoid arthritis.

2. The method of claim 1 , wherein the compound is administered via a non-oral route.

3. The method of claim 2 , wherein the non-oral route of administration is an intranasal route, a sub-cutaneous route or an intravenous route.

4. The method of claim 1 , wherein R 1 is

5. The method of claim 1 , wherein R 2 is H and R 3 is

6. The method of claim 5 , wherein R 3 is

7. The method of claim 1 , wherein R 2 forms a spirocyclic heterocyclic ring with R 3 to form

8. The method of claim 1 , wherein the compound of formula (I) is selected from the group consisting of:

N-{(2R)-3-(7-methyl-1H-indazol-5-yl)-1-oxo-1-[8-(piperidin-4-yl)-2,8-diazaspiro[4.5]dec-2-yl]propan-2-yl}-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide;

N-[(2R)-1-[8-(N-methyl-D-alanyl)-2,8-diazaspiro[4.5]dec-2-yl]-3-(7-methyl-1H-indazol-5-yl)-1-oxopropan-2-yl]-4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxamide;

N-[(2R)-1-[8-(N-methyl-D-alanyl)-2,8-diazaspiro[4.5]dec-2-yl]-3-(7-methyl-1H-indazol-5-yl)-1-oxopropan-2-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide;

N-{(2R)-3-(7-methyl-1H-indazol-5-yl)-1-oxo-1-[8-(piperidin-4-yl)-2,8-diazaspiro[4.5]dec-2-yl]propan-2-yl}-4-(2-oxo-1,4-dihydroquinazolin-3(2H)-yl)piperidine-1-carboxamide;

N-[(2R)-1-[8-(N-methyl-D-alanyl)-2,8-diazaspiro[4.5]dec-2-yl]-3-(7-methyl-1H-indazol-5-yl)-1-oxopropan-2-yl]-2′-oxo-1′,2′-dihydro-1H-spiro[piperidine-4,4′-pyrido[2,3-d][1,3]oxazine]-1-carboxamide;

N-[(2R)-1-[8-(N-methyl-D-alanyl)-2,8-diazaspiro[4.5]dec-2-yl]-3-(7-methyl-1H-indazol-5-yl)-1-oxopropan-2-yl]-4-(2-oxo-1,4-dihydroquinazolin-3(2H)-yl)piperidine-1-carboxamide; and

N-{(2R)-3-(7-methyl-1H-indazol-5-yl)-1-oxo-1-[8-(pyridin-4-yl)-2,8-diazaspiro[4.5]dec-2-yl]propan-2-yl}-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide;

or a salt thereof.

9. The method of claim 1 , wherein the compound of formula (I) is selected from the group consisting of:

N-{(2R)-3-(7-methyl-1H-indazol-5-yl)-1-oxo-1-[8-(piperidin-4-yl)-2,8-diazaspiro[4.5]dec-2-yl]propan-2-yl}-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide;

N-[(2R)-1-[8-(N-methyl-D-alanyl)-2,8-diazaspiro[4.5]dec-2-yl]-3-(7-methyl-1H-indazol-5-yl)-1-oxopropan-2-yl]-4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxamide;

N-[(2R)-1-[8-(N-methyl-D-alanyl)-2,8-diazaspiro[4.5]dec-2-yl]-3-(7-methyl-1H-indazol-5-yl)-1-oxopropan-2-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide;

N-{(2R)-3-(7-methyl-1H-indazol-5-yl)-1-oxo-1-[8-(piperidin-4-yl)-2,8-diazaspiro[4.5]dec-2-yl]propan-2-yl}-4-(2-oxo-1,4-dihydroquinazolin-3(2H)-yl)piperidine-1-carboxamide;

N-[(2R)-1-[8-(N-methyl-D-alanyl)-2,8-diazaspiro[4.5]dec-2-yl]-3-(7-methyl-1H-indazol-5-yl)-1-oxopropan-2-yl]-2′-oxo-1′,2′-dihydro-1H-spiro[piperidine-4,4′-pyrido[2,3-d][1,3]oxazine]-1-carboxamide;

N-[(2R)-1-[8-(N-methyl-D-alanyl)-2,8-diazaspiro[4.5]dec-2-yl]-3-(7-methyl-1H-indazol-5-yl)-1-oxopropan-2-yl]-4-(2-oxo-1,4-dihydroquinazolin-3(2H)-yl)piperidine-1-carboxamide; and

N-{(2R)-3-(7-methyl-1H-indazol-5-yl)-1-oxo-1-[8-(pyridin-4-yl)-2,8-diazaspiro[4.5]dec-2-yl]propan-2-yl}-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide.

10. The method of claim 1 , wherein the compound of formula (I) is

11. The method of claim 1 , wherein the compound of formula (I) is

or a salt thereof.

Assignments (3)
CHANGE OF NAME Recorded Sep 27, 2024
From: HEPTARES THERAPEUTICS LIMITED
To: NXERA PHARMA UK LIMITED
Reel/Frame 068728/0899 →
CHANGE OF ADDRESS Recorded Mar 21, 2019
From: HEPTARES THERAPEUTICS LIMITED
To: HEPTARES THERAPEUTICS LIMITED
Reel/Frame 048661/0096 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 29, 2018
From: CHRISTOPHER, JOHN ANDREW; CONGREVE, MILES STUART; BUCKNELL, SARAH JOANNE; DEFLORIAN, FRANCESCA; PICKWORTH, MARK; MASON, JONATHAN STEPHEN
To: HEPTARES THERAPEUTICS LIMITED
Reel/Frame 046737/0111 →
Priority Claims (1)
GB 1519195.0 · Oct 30, 2015 · national
Continuity (2)
Division 15336880 · Oct 28, 2016
Related Publication 20180009808A1 · Jan 11, 2018