Process for the synthesis of (s) 3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid
US-10836708-B2 · Nov 17, 2020 · US
Process for the synthesis of (s) 3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid
US12331006B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-12331006-B2 |
| Application number | US-202016950542-A |
| Country | US |
| Kind code | B2 |
| Filing date | Nov 17, 2020 |
| Priority date | May 25, 2018 |
| Publication date | Jun 17, 2025 |
| Grant date | Jun 17, 2025 |
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- Title
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- Abstract
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Abstract
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Provided herein are processes, compounds and compositions for making (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid. Also provided herein a pharmaceutical compositions containing (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid.
First claim
Opening claim text (preview).
What is claimed is: 1. A pharmaceutical composition comprising (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid (1), or a pharmaceutically acceptable salt thereof, and one or more of the following compounds: (1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-one (2), (1R,4S)-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]hept-5-en-3-one (3), (1R,4R,6S,7R)-7-bromo-2-(4-methoxybenzyl)-3-oxo-2-azabicyclo[2.2.1]heptan-6-yl acetate (4), (1R,4R,6S,7R)-7-bromo-6-hydroxy-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one (25), (1R,4R,7R)-7-bromo-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]heptane-3,6-dione (5), (1R,4R,7R)-7-bromo-6-(difluoromethylene)-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one (6), (1R,4R,7R)-7-bromo-6-(difluoromethylene)-2-azabicyclo[2.2.1]heptan-3-one (7), (1R,4R,7R)-7-bromo-6-(difluoromethylene)-2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]heptan-3-one (8), methyl (S)-3-((tert-butoxycarbonyl)amino)-4-(difluoromethylene)cyclopent-1-ene-1-carboxylate (9), ethyl (S)-3-((tert-butoxycarbonyl)amino)-4-(difluoromethylene)cyclopent-1-ene-1-carboxylate (15), and (S)-3-((tert-butoxycarbonyl)amino)-4-(difluoromethylene)cyclopent-1-ene-1-carboxylic acid (19), or a pharmaceutically acceptable salt of any of the preceding compounds. 2. The pharmaceutical composition of claim 1 comprising (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid (1), or a pharmaceutically acceptable B salt thereof, and from 0.0001 to 1 mg of (1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-one (2), or a pharmaceutically acceptable salt thereof. 3. The pharmaceutical composition of claim 1 comprising (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid (1), or a pharmaceutically acceptable salt thereof, and from 0.0001 to 1 mg of (1R,4S)-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]hept-5-en-3-one (3), or a pharmaceutically acceptable salt thereof. 4. The pharmaceutical composition of claim 1 comprising (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid (1), or a pharmaceutically acceptable B salt thereof, and from 0.0001 to 1 mg of (1R,4R,6S,7R)-7-bromo-2-(4-methoxybenzyl)-3-oxo-2-azabicyclo[2.2.1]heptan-6-yl acetate (4), or a pharmaceutically acceptable salt thereof. 5. The pharmaceutical composition of claim 1 comprising (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid (1), or a pharmaceutically acceptable B salt thereof, and from 0.0001 to 1 mg of (1R,4R,7R)-7-bromo-6-hydroxy-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one (25), or a pharmaceutically acceptable salt thereof. 6. The pharmaceutical composition of claim 1 comprising (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid (1), or a pharmaceutically acceptable B salt thereof, and from 0.0001 to 1 mg of (1R,4R,7R)-7-bromo-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]heptane-3,6-dione (5), or a pharmaceutically acceptable salt thereof. 7. The pharmaceutical composition of claim 1 comprising (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid (1), or a pharmaceutically acceptable B salt thereof, and from 0.0001 to 1 mg of (1R,4R,7R)-7-bromo-6-(difluoromethylene)-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]heptan-3-one (6), or a pharmaceutically acceptable salt thereof. 8. The pharmaceutical composition of claim 1 comprising (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid (1), or a pharmaceutically acceptable salt thereof, and from 0.0001 to 1 mg of (1R,4R,7R)-7-bromo-6-(difluoromethylene)-2-azabicyclo[2.2.1]heptan-3-one (7), or a pharmaceutically acceptable salt thereof. 9. The pharmaceutical composition of claim 1 comprising (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid (1), or a pharmaceutically acceptable salt thereof, and from 0.0001 to 1 mg of (1R,4R,7R)-7-bromo-6-(difluoromethylene)-2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]heptan-3-one (8), or a pharmaceutically acceptable salt thereof. 10. The pharmaceutical composition of claim 1 comprising (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid (1), or a pharmaceutically acceptable salt thereof, and from 0.0001 to 1 mg methyl of (S)-3-((tert-butoxycarbonyl)amino)-4-(difluoromethylene)cyclopent-1-ene-1-carboxylate (9), or a pharmaceutically acceptable salt thereof. 11. The pharmaceutical composition of claim 1 comprising (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid (1), or a pharmaceutically acceptable B salt thereof, and from 0.0001 to 1 mg of ethyl (S)-3-((tert-butoxycarbonyl)amino)-4-(difluoromethylene)cyclopent-1-ene-1-carboxylate (15), or a pharmaceutically acceptable salt thereof. 12. The pharmaceutical composition of claim 1 comprising (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid (1), or a pharmaceutically acceptable salt thereof, and from 0.0001 to 1 mg of (S)-3-((tert-butoxycarbonyl)amino)-4-(difluoromethylene )cyclopent-1-ene-1-carboxylic acid (19), or a pharmaceutically acceptable salt thereof.
Assignees
Inventors
Classifications
with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring · CPC title
Optical isomers · CPC title
Antineoplastic agents · CPC title
for treating abuse or dependence · CPC title
Antiepileptics; Anticonvulsants · CPC title
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Frequently asked questions
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- What does patent US12331006B2 cover?
- Provided herein are processes, compounds and compositions for making (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid. Also provided herein a pharmaceutical compositions containing (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid.
- Who is the assignee on this patent?
- Univ Northwestern
- What technology area does this patent fall under?
- Primary CPC classification C07C227/20. Mapped technology areas include Chemistry & Metallurgy.
- When was this patent published?
- Publication date Tue Jun 17 2025 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
- What related patents are in patentsdb?
- We list 4 related publications on this page (citations in our corpus or others sharing the same primary CPC).