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Apixaban

Tier A — Act now

Apixaban · all drugs expiring in 2028 →

Bristol Myers Squibb
Originator
2011
First approval
2028
Expiry (public)
$22.4B ▲
Peak sales
Small molecule
Type

Targets：F10

Brand：Eliquis

Indications (approved)：Pulmonary embolism, Venous thrombosis, Paget-Schroetter syndrome, Venous thromboembolism, Thrombosis, Embolism, Stroke, Ischaemic stroke

Regional status

US
Approved
2012-12-28
EU
Approved
2011-05-18
China
Approved
2013-01-22
Japan
Approved
2012-12-25

Synthetic routes & intermediates7 routes

Originator routes × 1Optimised (non-patent) × 5Process routes × 1

Routes are ordered originator first, then optimised / process (non-patent) routes; each lists steps, overall yield and the intermediate table (code / CAS / name) — ready for supplier sourcing and RFQ. Rendered by this site from structured data; no third-party route graphics used.

OriginatorRoute 1Steps 6 · Total yield 3.5 g
Synthetic routes & intermediates Route 1
CodeCAS No.Intermediate
APIX-001540-37-4Available4-iodoaniline
APIX-0024509-90-4Available5-bromopentanoyl chloride
APIX-003385425-15-0Available1-(4-iodophenyl)piperidin-2-one
APIX-004545445-10-1Available3,3-dichloro-1-(4-iodophenyl)piperidin-2-one
APIX-005473927-69-4Available1-(4-iodophenyl)-3-morpholino-5,6-dihydropyridin-2(1H)-one
APIX-00627143-07-3Availableethyl (Z)-2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate
APIX-007473927-64-9Availableethyl 6-(4-iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate
APIX-008675-20-7Availablepiperidin-2-one
APIX-009503614-91-3Availableethyl 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate
OptimisedRoute 2Steps 6 · Total yield 1.06 g
Synthetic routes & intermediates Route 2
CodeCAS No.Intermediate
APIX-003385425-15-0Available1-(4-iodophenyl)piperidin-2-one
APIX-00627143-07-3Availableethyl (Z)-2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate
APIX-008675-20-7Availablepiperidin-2-one
APIX-01041419-12-9Available3,3-dichloropiperidin-2-one
APIX-011207976-92-9Available3-chloro-5,6-dihydropyridin-2(1H)-one
APIX-012110-91-8Availablemorpholine
APIX-013545445-40-7Available3-morpholino-5,6-dihydropyridin-2(1H)-one
APIX-014503614-56-0Availableethyl 1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate
APIX-015503614-92-4Available1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid
OptimisedRoute 3Steps 8 · Total yield 60.19 g
Synthetic routes & intermediates Route 3
CodeCAS No.Intermediate
APIX-001540-37-4Available4-iodoaniline
APIX-003385425-15-0Available1-(4-iodophenyl)piperidin-2-one
APIX-004545445-10-1Available3,3-dichloro-1-(4-iodophenyl)piperidin-2-one
APIX-005473927-69-4Available1-(4-iodophenyl)-3-morpholino-5,6-dihydropyridin-2(1H)-one
APIX-00627143-07-3Availableethyl (Z)-2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate
APIX-008675-20-7Availablepiperidin-2-one
APIX-009503614-91-3Availableethyl 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate
APIX-012110-91-8Availablemorpholine
APIX-0162067-33-6Available5-bromopentanoic acid
APIX-0171539292-18-6Available5-bromo-N-(4-iodophenyl)pentanamide
APIX-0181619934-74-5Available3-chloro-1-(4-iodophenyl)-5,6-dihydropyridin-2(1H)-one
APIX-019545445-44-1Available3-morpholino-1-(4-(2-oxopiperidin-1-yl)phenyl)-5,6-dihydropyridin-2(1H)-one
OptimisedRoute 5Steps 6 · Total yield 2.07 g
Synthetic routes & intermediates Route 5
CodeCAS No.Intermediate
APIX-00627143-07-3Availableethyl (Z)-2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate
APIX-009503614-91-3Availableethyl 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate
APIX-019545445-44-1Available3-morpholino-1-(4-(2-oxopiperidin-1-yl)phenyl)-5,6-dihydropyridin-2(1H)-one
APIX-020100-01-6Available4-nitroaniline
APIX-02238560-30-4Available1-(4-nitrophenyl)piperidin-2-one
APIX-0281575-61-7Available5-chloropentanoyl chloride
APIX-029503615-03-0Available3-morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one
APIX-0301267610-26-3Available1-(4-aminophenyl)-3-morpholino-5,6-dihydropyridin-2(1H)-one
OptimisedRoute 6Steps 4 · Total yield 12.6 g
Synthetic routes & intermediates Route 6
CodeCAS No.Intermediate
APIX-00627143-07-3Availableethyl (Z)-2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate
APIX-007473927-64-9Availableethyl 6-(4-iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate
APIX-008675-20-7Availablepiperidin-2-one
APIX-009503614-91-3Availableethyl 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate
APIX-0311415831-82-1Available1-(4-iodophenyl)piperidine-2,3-dione
APIX-032a-1-(4-iodophenyl)-3-((trimethylsilyl)oxy)-5,6-dihydropyridin-2(1H)-one
APIX-032b-1-(4-iodophenyl)-2-oxo-1,2,5,6-tetrahydropyridin-3-yl 4-methylbenzenesulfonate
OptimisedRoute 7Steps 6 · Total yield 270 mg
Synthetic routes & intermediates Route 7
CodeCAS No.Intermediate
APIX-013545445-40-7Available3-morpholino-5,6-dihydropyridin-2(1H)-one
APIX-0211575-61-7Available-
APIX-033-N-(4-chlorophenyl)benzamide
APIX-034-N-(4-(5-morpholino-6-oxo-3,6-dihydropyridin-1(2H)-yl)phenyl)benzamide
APIX-035-methyl (Z)-2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate
APIX-036-methyl 6-(4-benzamidophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate
APIX-037-methyl 6-(4-aminophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate
APIX-0381423803-24-0Available6-(4-aminophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide
APIX-039-6-(4-(5-chloropentanamido)phenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide
ProcessRoute 4Steps 8 · Total yield 8.9 kg
Synthetic routes & intermediates Route 4
CodeCAS No.Intermediate
APIX-00627143-07-3Availableethyl (Z)-2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate
APIX-009503614-91-3Availableethyl 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate
APIX-020100-01-6Available4-nitroaniline
APIX-021a1575-61-7Available5-chloropentanoyl chloride
APIX-021b4509-90-4Available5-bromopentanoyl chloride
APIX-02238560-30-4Available1-(4-nitrophenyl)piperidin-2-one
APIX-023881386-01-2Available3,3-dichloro-1-(4-nitrophenyl)piperidin-2-one
APIX-024536760-29-9Available3-chloro-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one
APIX-025536759-91-8Availableethyl 1-(4-methoxyphenyl)-6-(4-nitrophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate
APIX-026503615-07-4Availableethyl 6-(4-aminophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate
APIX-027a-ethyl 6-(4-(5-chloropentanamido)phenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate
APIX-027b-ethyl 6-(4-(5-bromopentanamido)phenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate

Frequently asked questions

What are the approved indications of Apixaban?

Approved indications include: Pulmonary embolism, Venous thrombosis, Paget-Schroetter syndrome, Venous thromboembolism, Thrombosis, Embolism, Stroke, Ischaemic stroke.

When does the Apixaban patent expire?

Based on public sources, the Apixaban patent expires in 2028.

How many synthesis routes are recorded for Apixaban?

7 synthesis routes are recorded; the shortest is 4 steps with 12.6 g total yield. Intermediates in each route carry codes and CAS numbers.

Where can I buy Apixaban intermediates?

30 intermediate CAS of Apixaban are available through the Unibest supply network — see the route tables on this page and request a quote per CAS.

How do I get a quote for Apixaban intermediates?

Open the CAS profile of the target intermediate from this page, or submit an RFQ directly — the CAS enters the matching flow automatically and the supply network responds with quotes.

Source: cross-verified data (structured fields only) · 2026-09-29