← Back to patent-cliff list
Ibrutinib
Tier A — Act nowIbrutinib · all drugs expiring in 2027 →
Pharmacyclics Llc
Originator
2013
First approval
2027
Expiry (public)
$9.78B ▲
Peak sales
Small molecule
Type
Targets：BTK
Brand：Imbruvica
Indications (approved)：Waldenström macroglobulinaemia, Chronic lymphocytic leukaemia, Mantle cell lymphoma, Graft-versus-host disease
Regional status
US
Approved
2013-11-13
EU
Approved
2014-10-21
China
Approved
2017-08-24
Japan
Approved
2016-03-28
Factories producing this API1
Factories registered as producing this API in our sourcing network (RFQ records + product master), sorted by RFQ activity; the snapshot carries no cost or customer data.
1 producing factories on file — sign in to view the named list (factory details are not shown to guests).
Sign in to view factories →Synthetic routes & intermediates33 routes
Originator routes × 1Optimised (non-patent) × 32Process routes × 0
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 8 · Total yield 22 mg
| Code | CAS No. | Intermediate |
|---|---|---|
| IBRT-001 | 2215-77-2Available | 4-phenoxybenzoic acid |
| IBRT-002 | 330792-68-2 | 2-(hydroxy(4-phenoxyphenyl)methylene)malononitrile |
| IBRT-003 | 330792-69-3 | 2-(methoxy(4-phenoxyphenyl)methylene)malononitrile |
| IBRT-004 | 330792-70-6Available | 5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile |
| IBRT-005 | 330786-24-8Available | 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| IBRT-006 | 143900-44-1Available | (S)-tert-butyl 3-hydroxypiperidine-1-carboxylate |
| IBRT-007 | 1022150-11-3 | (R)-tert-butyl 3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate |
| IBRT-008 | 814-68-6Available | acryloyl chloride |
| IBRT-009 | 2380-63-4 | 1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| IBRT-010 | 151266-23-8Available | 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| IBRT-011 | 51067-38-0 | tert-butyl 4-(((6-amino-5-chloropyrimidin-4-yl)amino)methyl)piperidine-1-carboxylate |
OptimisedRoute 2Steps 3 · Total yield 3.2 g
| Code | CAS No. | Intermediate |
|---|---|---|
| IBRT-003 | 330792-69-3 | 2-(methoxy(4-phenoxyphenyl)methylene)malononitrile |
| IBRT-012 | 1623-95-6 | 4-phenoxybenzoyl chloride |
| IBRT-013 | 1574506-73-2 | (R)-1-(3-hydrazinylpiperidin-1-yl)prop-2-en-1-one |
| IBRT-014 | 1574506-72-1 | (R)-1-(1-acryloylpiperidin-3-yl)-5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile |
OptimisedRoute 3Steps 4 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-2-a | 83255-86-1 | 3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (II)461018-2-a | 51067-38-0 | (4-Phenoxyphenyl)boranediol |
| (III)461018-2-a | 330786-24-8Available | 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (IV)461018-2-a | - | N-Boc-3(S)-Hydroxypiperidine |
| (IX)461018-2-a | 814-68-6Available | 2-Propenoyl chloride |
| (V)461018-2-a | 1022150-11-3 | (3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester |
| (VI)461018-2-a | 354-32-5 | Perfluoroacetyl chloride |
| (VII)461018-2-a | 1441076-08-9 | tert-Butyl (3R)-3-[3-(4-phenoxyphenyl)-4-[(trifluoroacetyl)amino]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate |
| (VIII)461018-2-a | 1441076-09-0 | 2,2,2-Trifluoro-N-[3-(4-phenoxyphenyl)-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-yl]acetamide |
| (X)461018-2-a | 1441076-10-3 | N-[1-[(3R)-1-Acryloylpiperidin-3-yl]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-2,2,2-trifluoroacetamide |
OptimisedRoute 4Steps 4 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-3-a | 1623-95-6 | 4-Phenoxybenzoyl chloride |
| (II)461018-3-a | 109-77-3Available | 1,1-Dicyanomethane |
| (III)461018-3-a | 330792-68-2 | (4-Phenoxybenzoyl)malononitrile |
| (IV)461018-3-a | 330792-69-3 | 1,1-Dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene |
| (V)461018-3-a | 1574506-73-2 | 1-[(3R)-3-Hydrazinopiperidin-1-yl]prop-2-en-1-one |
| (VI)461018-3-a | 1574506-72-1 | 1-[(3R)-1-Acryloylpiperidin-3-yl]-5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile |
| (VII)461018-3-a | 4637-24-5Available | (Dimethylamino)formaldehyde dimethyl acetal |
OptimisedRoute 5Steps 5 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-4-a | 2215-77-2Available | 4-(Phenyloxy)benzoic acid |
| (II)461018-4-a | 541-41-3 | Carbonochloridic acid ethyl ester |
| (III)461018-4-a | 1652601-99-4 | Ethyl 4-phenoxybenzoyl carbonate |
| (IV)461018-4-a | 109-77-3Available | 1,1-Dicyanomethane |
| (IX)461018-4-a | 330786-24-8Available | 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (V)461018-4-a | 330792-68-2 | (4-Phenoxybenzoyl)malononitrile |
| (VI)461018-4-a | 1824684-85-6 | [Chloro(4-phenoxyphenyl)methylene]malononitrile |
| (VII)461018-4-a | 330792-70-6Available | 3-Amino-4-cyano-5-(4-phenoxyphenyl)pyrazole |
| (VIII)461018-4-a | 3473-63-0 | Formamidine acetate |
| (Xa)461018-4-a | 637338-78-4 | 3-Chloro-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (Xb)461018-4-a | 83255-86-1 | 3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (Xc)461018-4-a | 151266-23-8Available | 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (Xd)461018-4-a | 2395781-95-8 | 4-Amino-1H-pyrazolo[3,4-d]pyrimidin-3-ylmethanesulfonate |
OptimisedRoute 6Steps 5 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-5-a | 21461-84-7 | (2S)-5-oxooxolane-2-carboxylic acid |
| (II)461018-5-a | 1798323-71-3 | (2S)-5-(Benzylamino)-2-hydroxy-5-oxopentanoic acid |
| (IIIa)461018-5-a | 1798323-73-5 | (3S)-1-Benzyl-2,6-dioxopiperidin-3-yl acetate |
| (IIIb)461018-5-a | 1798323-79-1 | (3S)-1-Benzyl-2,6-dioxopiperidin-3-yl chloroacetate |
| (IIIc)461018-5-a | 1798323-81-5 | (3S)-1-Benzyl-2,6-dioxopiperidin-3-yl trifluoroacetate |
| (IV)461018-5-a | 91599-79-0 | (3S)-1-Benzylpiperidin-3-ol |
| (V)461018-5-a | 1798323-76-8 | (3S)-Piperidin-3-ol acetate |
| (VI)461018-5-a | 143900-44-1Available | (3S)-1-(tert-Butoxycarbonyl)-3-hydroxypiperidine |
OptimisedRoute 7Steps 4 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-6-a | 143900-44-1Available | (3S)-1-(tert-Butoxycarbonyl)-3-hydroxypiperidine |
| (IIa)461018-6-a | 191092-08-7 | (S)-1-tert-Butoxycarbonyl-3-(p-toluenesulfonyloxymethyl)piperidine |
| (IIb)461018-6-a | 2315115-22-9 | tert-Butyl (3S)-3-[[tert-butyl(dimethyl)silyl]oxy]piperidine-1-carboxylate |
| (IIIa)461018-6-a | 1816998-80-7 | (3S)-Piperidin-3-yl 4-methylbenzenesulfonate |
| (IIIb)461018-6-a | 1374144-82-7 | (3S)-3-[[tert-Butyl(dimethyl)silyl]oxy]piperidine |
| (IV)461018-6-a | 814-68-6Available | 2-Propenoyl chloride |
| (V)461018-6-a | 79-10-7 | 2-Propenoic acid |
| (VIa)461018-6-a | 1816998-81-8 | (3S)-1-Acryloylpiperidin-3-yl 4-methylbenzenesulfonate |
| (VIb)461018-6-a | 1816998-83-0 | 1-[(3S)-3-[[tert-Butyl(dimethyl)silyl]oxy]piperidin-1-yl]prop-2-en-1-one |
| (VII)461018-6-a | 1816998-82-9 | (3S)-1-Acryloylpiperidin-3-yl 4-nitrobenzenesulfonate |
| (VIII)461018-6-a | 330786-24-8Available | 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
OptimisedRoute 8Steps 4 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (Ia)461018-7-a | 101-55-3 | 1-Bromo-4-phenoxybenzene |
| (Ib)461018-7-a | - | 1,1'-Oxydibenzene |
| (II)461018-7-a | 5305-40-8 | 4,6-Dichloropyrimidine-5-carbaldehyde |
| (III)461018-7-a | 1850315-20-6 | (4,6-Dichloropyrimidin-5-yl)(4-phenoxyphenyl)methanol |
| (IV)461018-7-a | 1807637-54-2 | (4,6-Dichloropyrimidin-5-yl)(4-phenoxyphenyl)methanone |
| (V)461018-7-a | 1850315-21-7 | 4-Chloro-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine |
| (VI)461018-7-a | 330786-24-8Available | 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
OptimisedRoute 9Steps 6 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-8-a | 16617-46-2 | 3-Amino-1H-pyrazole-4-carbonitrile |
| (II)461018-8-a,(II)461018-8-b | 75-12-7 | Amide c1 |
| (III)461018-8-a | 2380-63-4 | 1H-Pyrazolo[3,4-d]pyrimidin-4-amine |
| (IVa)461018-8-a | 151266-23-8Available | 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (IVb)461018-8-a | 83255-86-1 | 3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (IX)461018-8-a | 814-68-6Available | 2-Propenoyl chloride |
| (V)461018-8-a | 143900-44-1Available | (3S)-1-(tert-Butoxycarbonyl)-3-hydroxypiperidine |
| (VI)461018-8-a | 940890-90-4 | (S)-1-(tert-Butoxycarbonyl)piperidin-3-yl methanesulfonate |
| (VIIa)461018-8-a | 1276110-38-3 | tert-Butyl (3R)-3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate |
| (VIIb)461018-8-a,(VIIb)461018-8-b | 1419223-01-0 | tert-Butyl (3R)-3-(4-amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate |
| (VIIIa)461018-8-a | 1928705-12-7 | 3-Iodo-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine hydrogen chloride |
| (VIIIb)461018-8-a | 1928705-14-9 | 3-Bromo-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (VIIIc)461018-8-a | 1989746-21-5 | 3-Iodo-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine--hydrogen chloride (1 |
| (VIIId)461018-8-a | 1638522-98-1 | 3-Iodo-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (X)461018-8-a | 79-10-7 | 2-Propenoic acid |
| (XIa)461018-8-a | 1873339-79-7 | 1-[(3R)-3-(4-Amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl]prop-2-en-1-one |
| (XIb)461018-8-a | 1928705-13-8 | 1-[(3R)-3-(4-Amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl]prop-2-en-1-one |
| (XII)461018-8-a | 51067-38-0 | (4-Phenoxyphenyl)boranediol |
| (XIIIa)461018-8-a | 625-36-5Available | (Chloromethyl)acetyl chloride |
| (XIIIb)461018-8-a | 7623-16-7 | 3-Bromopropanoyl bromide |
| (XIVa)461018-8-a | 1985609-75-3 | 1-[(3R)-3-(4-Amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl]-3-chloropropan-1-one |
| (XIVb)461018-8-a | 1985609-76-4 | 1-[(3R)-3-(4-Amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl]-3-bromopropan-1-one |
OptimisedRoute 10Steps 6 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-9-a | 42839-04-3 | Pyrimidine-4-carbonitrile |
| (II)461018-9-a | 939986-65-9 | 6-Chloropyrimidine-4-carbonitrile |
| (III)461018-9-a | 870-46-2 | (tert-Butoxycarbonyl)hydrazine |
| (IV)461018-9-a | 2408965-53-5 | 6-Hydrazinylpyrimidine-4-carbonitrile hydrogen chloride |
| (IXa)461018-9-a | 625-36-5Available | (Chloromethyl)acetyl chloride |
| (IXb)461018-9-a | 15486-96-1Available | 3-Bromopropanoyl chloride |
| (IXc)461018-9-a | 7623-16-7 | 3-Bromopropanoyl bromide |
| (V)461018-9-a | 67-36-7 | 4-Phenoxybenzaldehyde |
| (VI)461018-9-a | 330786-24-8Available | 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (VII)461018-9-a | 1354010-30-2 | N-Boc-3(S)-chloropiperidine |
| (VIII)461018-9-a | 1022150-12-4Available | (R)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (Xa)461018-9-a | 1288338-96-4 | 1-[(3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-3-chloropropan-1-one |
| (Xb)461018-9-a | 1899029-09-4 | 1-[(3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-3-bromopropan-1-one |
OptimisedRoute 11Steps 4 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-10-a | 1193-24-4 | 4,6-Dihydroxypyrimidine |
| (II)461018-10-a | 5305-40-8 | 4,6-Dichloropyrimidine-5-carbaldehyde |
| (III)461018-10-a | 101-55-3 | 1-Bromo-4-phenoxybenzene |
| (IV)461018-10-a | 1850315-20-6 | (4,6-Dichloropyrimidin-5-yl)(4-phenoxyphenyl)methanol |
| (IX)461018-10-a | 1022150-11-3 | (3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester |
| (V)461018-10-a | 1807637-54-2 | (4,6-Dichloropyrimidin-5-yl)(4-phenoxyphenyl)methanone |
| (VI)461018-10-a | 1807637-55-3 | (4-Amino-6-chloropyrimidin-5-yl)(4-phenoxyphenyl)methanone |
| (VII)461018-10-a | 330786-24-8Available | 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (VIII)461018-10-a | 1354010-30-2 | N-Boc-3(S)-chloropiperidine |
| (Xa)461018-10-a | 1022150-12-4Available | (R)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (Xb)461018-10-a | 1553977-42-6 | 3-(4-Phenoxyphenyl)-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine hydrogen chloride |
| (XI)461018-10-a | 814-68-6Available | 2-Propenoyl chloride |
| (XII)461018-10-a | 625-36-5Available | (Chloromethyl)acetyl chloride |
OptimisedRoute 12Steps 5 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-11-a | 2380-63-4 | 1H-Pyrazolo[3,4-d]pyrimidin-4-amine |
| (II)461018-11-a | 83255-86-1 | 3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (IIIa)461018-11-a | 143900-44-1Available | (3S)-1-(tert-Butoxycarbonyl)-3-hydroxypiperidine |
| (IIIb)461018-11-a | 940890-90-4 | (S)-1-(tert-Butoxycarbonyl)piperidin-3-yl methanesulfonate |
| (IVa)461018-11-a | 1419223-01-0 | tert-Butyl (3R)-3-(4-amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate |
| (IVb)461018-11-a | 1276110-38-3 | tert-Butyl (3R)-3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate |
| (V)461018-11-a | 151266-23-8Available | 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (VIa)461018-11-a | 1985609-74-2 | 3-Bromo-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine hydrogen chloride (1/2) |
| (VIb)461018-11-a | 1989746-21-5 | 3-Iodo-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine--hydrogen chloride (1/2) |
| (VIc)(IX)461018-11-a | 1553977-42-6 | 3-(4-Phenoxyphenyl)-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine hydrogen chloride |
| (VII)461018-11-a | 51067-38-0 | (4-Phenoxyphenyl)boranediol |
| (VIII)461018-11-a | 1022150-12-4Available | (R)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (X)461018-11-a | 814-68-6Available | 2-Propenoyl chloride |
OptimisedRoute 13Steps 3 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-12-a | 143900-44-1Available | (3S)-1-(tert-Butoxycarbonyl)-3-hydroxypiperidine |
| (II)461018-12-a | 191092-08-7 | (S)-1-tert-Butoxycarbonyl-3-(p-toluenesulfonyloxymethyl)piperidine |
| (IIIa)461018-12-a | 83255-86-1 | 3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (IIIb)461018-12-a | 151266-23-8Available | 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (IVa)461018-12-a | 1419223-01-0 | tert-Butyl (3R)-3-(4-amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate |
| (IVb)461018-12-a | 1276110-38-3 | tert-Butyl (3R)-3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate |
| (Va)461018-12-a | 1928705-14-9 | 3-Bromo-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (Vb)461018-12-a | 1638522-98-1 | 3-Iodo-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (VI)461018-12-a | 330786-24-8Available | 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (VII)461018-12-a | 1022150-11-3 | (3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester |
| (VIII)461018-12-a | 1022150-12-4Available | (R)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
OptimisedRoute 14Steps 2 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-13-a | 1022150-12-4Available | (R)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (IIa)461018-13-a | 7623-09-8 | 1,2 Dichloro-1-propanone |
| (IIb)461018-13-a | 563-76-8 | 2-Bromopropanoyl bromide |
| (IIIa)461018-13-a | 1906970-58-8 | 1-[(3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-2-chloropropan-1-one |
| (IIIb)461018-13-a | 1906970-57-7 | 1-[(3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-2-bromopropan-1-one |
OptimisedRoute 15Steps 2 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (Ia)461018-14-a | 2380-63-4 | 1H-Pyrazolo[3,4-d]pyrimidin-4-amine |
| (Ib)461018-14-a | 83255-86-1 | 3-Bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (IIa)461018-14-a | 2974-94-9 | 1-Iodo-4-phenoxybenzene |
| (IIb)461018-14-a | 51067-38-0 | (4-Phenoxyphenyl)boranediol |
| (III)461018-14-a | 330786-24-8Available | 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (IV)461018-14-a | 1642601-01-1 | 1-[(3S)-3-Hydroxypiperidin-1-yl]prop-2-en-1-one |
| (V)461018-14-a | 475058-41-4 | (3S)-Piperidin-3-ol--hydrogen chloride (1 |
| (VI)461018-14-a | 79-10-7 | 2-Propenoic acid |
OptimisedRoute 16Steps 4 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-15-a | 87600-98-4 | 4,6-Dichloropyrimidine-5-carboxylic acid |
| (II)461018-15-a | 87600-97-3 | 4,6-Dichloropyrimidine-5-carbonyl chloride |
| (III)461018-15-a | - | 1,1'-Oxydibenzene |
| (IV)461018-15-a | 1807637-54-2 | (4,6-Dichloropyrimidin-5-yl)(4-phenoxyphenyl)methanone |
| (V)461018-15-a | 1807637-55-3 | (4-Amino-6-chloropyrimidin-5-yl)(4-phenoxyphenyl)methanone |
| (VIa)461018-15-a | 302-01-2Available | Diamine |
| (VIb)461018-15-a | 30929-57-8 | Cyclohexylhydrazine hydrogen chloride |
| (VIIa)461018-15-a | 330786-24-8Available | 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (VIIb)461018-15-a | 1914997-73-1 | 1-Cyclohexyl-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
OptimisedRoute 17Steps 4 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-17-a | 475058-41-4 | (3S)-Piperidin-3-ol--hydrogen chloride (1 |
| (II)461018-17-a | 1126736-20-6 | 2,2,2-Trifluoro-1-[(3S)-3-hydroxypiperidin-1-yl]ethan-1-one |
| (III)461018-17-a | 330786-24-8Available | 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (IV)461018-17-a | 1906970-30-6 | 1-[(3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-2,2,2-trifluoroethan-1-one |
| (V)461018-17-a | 2095781-68-1 | 2,2,2-Trifluoro-1-[(3R)-3-[3-(4-phenoxyphenyl)-4-[(triphenyl-lambda5-phosphanylidene)amino]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]ethan-1-one |
| (VI)461018-17-a | 1022150-12-4Available | (R)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (VII)461018-17-a | 814-68-6Available | 2-Propenoyl chloride |
OptimisedRoute 18Steps 2 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (Ia)461018-18-a | 2088495-73-0 | Benzyl (3R)-3-(4-[[(benzyloxy)carbonyl]amino]-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate |
| (Ib)461018-18-a | 2088495-74-1 | tert-Butyl (3R)-3-[4-[(tert-butoxycarbonyl)amino]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate |
| (II)461018-18-a | 101-55-3 | 1-Bromo-4-phenoxybenzene |
| (IIIa)461018-18-a | 2088495-71-8 | Benzyl (3R)-3-[4-[[(benzyloxy)carbonyl]amino]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate |
| (IIIb)461018-18-a | 2088495-72-9 | tert-Butyl (3R)-3-[4-[(tert-butoxycarbonyl)amino]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate |
| (IV)461018-18-a | 1022150-12-4Available | (R)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
OptimisedRoute 19Steps 1 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-19-a | 1846596-88-0 | tert-Butyl (3R)-3-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate |
| (II)461018-19-a | 101-55-3 | 1-Bromo-4-phenoxybenzene |
| (III)461018-19-a | 1022150-11-3 | (3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylic acid 1,1-dimethylethyl ester |
OptimisedRoute 20Steps 6 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-20-a | 143900-44-1Available | (3S)-1-(tert-Butoxycarbonyl)-3-hydroxypiperidine |
| (II)461018-20-a | 475058-41-4 | (3S)-Piperidin-3-ol--hydrogen chloride (1 |
| (III)461018-20-a | 91599-79-0 | (3S)-1-Benzylpiperidin-3-ol |
| (IV)461018-20-a | 2121460-13-5 | (3S)-1-Benzylpiperidin-3-yl methanesulfonate |
| (IX)461018-20-a | 79-10-7 | 2-Propenoic acid |
| (V)461018-20-a | 2760218-96-8 | (3S)-Piperidin-3-yl methanesulfonate |
| (VI)461018-20-a | 330786-24-8Available | 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (VII)461018-20-a | 2012523-61-2 | 1-[(3R)-1-Benzylpiperidin-3-yl]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (VIII)461018-20-a | 1022150-12-4Available | (R)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (X)461018-20-a | 814-68-6Available | 2-Propenoyl chloride |
| (XI)461018-20-a | 1642601-01-1 | 1-[(3S)-3-Hydroxypiperidin-1-yl]prop-2-en-1-one |
| (XII)461018-20-a | 1820971-88-7 | (3S)-1-(Prop-2-enoyl)piperidin-3-yl methanesulfonate |
OptimisedRoute 21Steps 4 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-21-a | 143900-44-1Available | (3S)-1-(tert-Butoxycarbonyl)-3-hydroxypiperidine |
| (II)461018-21-a | - | (3S)-1-(3,3-Dimethylbutanoyl)piperidin-3-yl 4-methylbenzene-1-sulfonate |
| (III)461018-21-a | 1816998-80-7 | (3S)-Piperidin-3-yl 4-methylbenzenesulfonate |
| (IV)461018-21-a | 814-68-6Available | 2-Propenoyl chloride |
| (IX)461018-21-a | 51067-38-0 | (4-Phenoxyphenyl)boranediol |
| (V)461018-21-a | 1816998-81-8 | (3S)-1-Acryloylpiperidin-3-yl 4-methylbenzenesulfonate |
| (VI)461018-21-a | 330786-24-8Available | 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (VII)461018-21-a | 2380-63-4 | 1H-Pyrazolo[3,4-d]pyrimidin-4-amine |
| (VIII)461018-21-a | 151266-23-8Available | 3-Iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
OptimisedRoute 22Steps 4 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-22-a | 67-36-7 | 4-Phenoxybenzaldehyde |
| (II)461018-22-a | 109-77-3Available | 1,1-Dicyanomethane |
| (III)461018-22-a | 64781-22-2 | [(4-Phenoxyphenyl)methylidene]propanedinitrile |
| (IV)461018-22-a | 10217-52-4,7803-57-8 | Hydrazine hydrate |
| (IX)461018-22-a | 1576-35-8 | 4-Methylbenzenesulfonhydrazide |
| (V)461018-22-a | 2097595-50-9 | 5-Amino-3-(4-phenoxyphenyl)-2,3-dihydro-1H-pyrazole-4-carbonitrile |
| (VI)461018-22-a | 2097595-51-0 | 3-(4-Phenoxyphenyl)-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (VII)461018-22-a | 330786-24-8Available | 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (VIII)461018-22-a | 330792-70-6Available | 3-Amino-4-cyano-5-(4-phenoxyphenyl)pyrazole |
| (X)461018-22-a | - | 4-Methyl-N'-[(4-phenoxyphenyl)methyl]benzene-1-sulfonohydrazide |
| (XI)461018-22-a | 75-12-7 | Amide c1 |
OptimisedRoute 23Steps 1 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-23-a | 79-10-7 | 2-Propenoic acid |
| (II)461018-23-a | 1022150-12-4Available | (R)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
OptimisedRoute 24Steps 1 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-24-a | 85275-45-2 | 1-Boc-3-hydroxypiperidine |
| (II)461018-24-a | 2222128-84-7 | N-Boc-3(S)-Piperidinyl butyrate |
OptimisedRoute 25Steps 6 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-25-a | 188111-79-7 | (3R)-3-Amino-1-piperidinecarboxylic acid 1,1-dimethylethyl ester |
| (II)461018-25-a,(II)461018-25-b | 2138465-88-8 | tert-Butyl (3R)-3-[(tert-butoxycarbonyl)(nitroso)amino]piperidine-1-carboxylate |
| (III)461018-25-a | 2138465-89-9 | tert-Butyl (3R)-3-[1-(tert-butoxycarbonyl)hydrazinyl]piperidine-1-carboxylate |
| (IV)461018-25-a | 1914997-74-2 | (3R)-3-Hydrazinylpiperidine |
| (IX)461018-25-a | 75-12-7 | Amide c1 |
| (V)461018-25-a | 330792-69-3 | 1,1-Dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene |
| (VI)461018-25-a | 1623-95-6 | 4-Phenoxybenzoyl chloride |
| (VII)461018-25-a | 109-77-3Available | 1,1-Dicyanomethane |
| (VIII)461018-25-a | 2138465-90-2 | 5-Amino-3-(4-phenoxyphenyl)-1-[(3R)-piperidin-3-yl]-1H-pyrazole-4-carbonitrile |
| (X)461018-25-a | 1628179-43-0 | (3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbaldehyde |
| (XI)461018-25-a | 814-68-6Available | 2-Propenoyl chloride |
| (XII)461018-25-b | 54012-73-6Available | 3-Aminopiperidine |
| (XIII)461018-25-b | 2161366-04-5 | 5-Oxo-D-proline (3R)-piperidin-3-amine |
| (XIV)461018-25-b | 1263078-12-1 | tert-Butyl (3R)-3-[(tert-butoxycarbonyl)amino]piperidine-1-carboxylate |
OptimisedRoute 26Steps 4 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-26-a | 110-86-1 | Azabenzene |
| (II)461018-26-a | 636-73-7Available | 3-Pyridylsulfonic acid |
| (III)461018-26-a | 109-00-2 | 3-Hydroxypyridine |
| (IV)461018-26-a | 6859-99-0 | 3-Hydroxypiperidine |
| (IX)461018-26-a | 167112-94-9 | (2S,3S)-4-[(4-Chlorophenyl)amino]-2,3-dihydroxy-4-oxobutanoic acid (3S)-piperidin-3-ol |
| (V)461018-26-a | 14813-01-5 | 1-(Phenylmethyl)-3-piperidinol |
| (VI)461018-26-a | 46834-56-4 | (2S,3S)-4-((4-Chlorophenyl)amino)-2,3-dihydroxy-4-oxobutanoic acid |
| (VII)461018-26-a | 147-71-7Available | (2S,3S)-(-)-Tartaric acid |
| (VIII)461018-26-a | 106-47-8 | 1-Amino-4-chlorobenzene |
| (X)461018-26-a | 143900-44-1Available | (3S)-1-(tert-Butoxycarbonyl)-3-hydroxypiperidine |
OptimisedRoute 27Steps 6 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-27-a | 109-77-3Available | 1,1-Dicyanomethane |
| (II)461018-27-a | 122-51-0Available | (Diethoxymethoxy)ethane |
| (III)461018-27-a | 123-06-8 | (Ethoxymethylene)malononitrile |
| (IV)461018-27-a | 2161366-06-7 | N-Boc-3(R)-hydrazinylpiperidine |
| (IX)461018-27-a | 51067-38-0 | (4-Phenoxyphenyl)boranediol |
| (V)461018-27-a | 2685868-56-6 | tert-Butyl (3R)-3-(5-amino-4-cyano-1H-pyrazol-1-yl)piperidine-1-carboxylate |
| (VI)461018-27-a | 75-12-7 | Amide c1 |
| (VII)461018-27-a | 1846596-88-0 | tert-Butyl (3R)-3-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate |
| (VIII)461018-27-a | 1419223-01-0 | tert-Butyl (3R)-3-(4-amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate |
| (X)461018-27-a | 1022150-12-4Available | (R)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (XI)461018-27-a | 40736-25-2 | 1-(1H-Imidazol-1-yl)prop-2-en-1-one |
| (XII)461018-27-a | 2183504-50-7 | 5-Chloro-1-[(prop-2-enoyl)oxy]-1H-benzotriazole |
OptimisedRoute 28Steps 7 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-28-a | 1276110-38-3 | tert-Butyl (3R)-3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate |
| (II)461018-28-a | 146631-00-7 | 1-Benzyloxy-4-boronic acid |
| (III)461018-28-a | 2096372-44-8 | tert-Butyl (3R)-3-[4-amino-3-[4-(benzyloxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate |
| (IV)461018-28-a | 2396827-24-8 | tert-Butyl (3R)-3-[3-[4-(benzyloxy)phenyl]-4-[bis(tert-butoxycarbonyl)amino]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate |
| (IX)461018-28-a | 1044519-48-3 | ([13C]-1,2,3,4,5,6)Phenylboronic acid |
| (V)461018-28-a | 2396827-25-9 | tert-Butyl (3R)-3-[4-[bis(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate |
| (VI)461018-28-a | 2719735-93-8 | tert-Butyl (3R)-3-[4-[bis(tert-butoxycarbonyl)amino]-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate |
| (VII)461018-28-a | 71597-85-8 | (4-Hydroxyphenyl)boronic acid |
| (VIII)461018-28-a | 112630-77-0 | 1-Bromo(13C6)benzene |
| (X)461018-28-a | - | tert-Butyl (3R)-3-(4-[bis(tert-butoxycarbonyl)amino]-3-[4-[([13C]-1,2,3,4,5,6)phenyloxy]phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate |
| (XI)461018-28-a | - | 3-[4-[([13C]-1,2,3,4,5,6)Phenyloxy]phenyl]-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (XII)461018-28-a | 814-68-6Available | 2-Propenoyl chloride |
| (XIII)461018-28-a | 2719735-92-7 | 1-[(3R)-3-(4-Amino-3-[4-[([13C]-1,2,3,4,5,6)phenyloxy]phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl]prop-2-en-1-one |
OptimisedRoute 29Steps 2 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-29-a | 330792-70-6Available | 3-Amino-4-cyano-5-(4-phenoxyphenyl)pyrazole |
| (II)461018-29-a | 1642601-01-1 | 1-[(3S)-3-Hydroxypiperidin-1-yl]prop-2-en-1-one |
| (III)461018-29-a | 1574506-72-1 | 1-[(3R)-1-Acryloylpiperidin-3-yl]-5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile |
| (IV)461018-29-a | 75-12-7 | Amide c1 |
OptimisedRoute 30Steps 5 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-31-a | 17180-93-7 | 4-Chloropyrimidine |
| (II)461018-31-a | 2759281-34-8 | tert-Butyl (3R)-3-[2-(tert-butoxycarbonyl)hydrazinyl]piperidine-1-carboxylate |
| (III)461018-31-a | 2759281-35-9 | tert-Butyl (3R)-3-[2-(tert-butoxycarbonyl)-1-(pyrimidin-4-yl)hydrazinyl]piperidine-1-carboxylate |
| (IV)461018-31-a | 2759281-36-0 | 4-Bromo-6-[1-[(3R)-piperidin-3-yl]hydrazinyl]pyrimidine |
| (V)461018-31-a | 67-36-7 | 4-Phenoxybenzaldehyde |
| (VI)461018-31-a | 2759281-37-1 | 4-Bromo-3-(4-phenoxyphenyl)-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidine |
| (VII)461018-31-a | 1022150-12-4Available | (R)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (VIII)461018-31-a | 814-68-6Available | 2-Propenoyl chloride |
OptimisedRoute 31Steps 5 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-32-a | 143900-44-1Available | (3S)-1-(tert-Butoxycarbonyl)-3-hydroxypiperidine |
| (II)461018-32-a | 191092-08-7 | (S)-1-tert-Butoxycarbonyl-3-(p-toluenesulfonyloxymethyl)piperidine |
| (III)461018-32-a | 1816998-80-7 | (3S)-Piperidin-3-yl 4-methylbenzenesulfonate |
| (IV)461018-32-a | 625-36-5Available | (Chloromethyl)acetyl chloride |
| (V)461018-32-a | - | (3S)-1-(3-Chloropropanoyl)piperidin-3-yl 4-methylbenzene-1-sulfonate |
| (VI)461018-32-a | 330786-24-8Available | 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (VII)461018-32-a | 1288338-96-4 | 1-[(3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]-3-chloropropan-1-one |
OptimisedRoute 32Steps 2 · Total yield /
OptimisedRoute 33Steps 5 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| (I)461018-34-a | 330786-24-8Available | 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine |
| (II)461018-34-a | - | Di-tert-butyl [3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-2-imidodicarbonate |
| (III)461018-34-a | 91599-79-0 | (3S)-1-Benzylpiperidin-3-ol |
| (IV)461018-34-a | - | Di-tert-butyl [1-[(3R)-1-benzylpiperidin-3-yl]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-2-imidodicarbonate |
| (IX)461018-34-a | 13618-91-2 | 4,5,6,7-Tetrahydro-1H-indole |
| (V)461018-34-a | - | Di-tert-butyl [3-(4-phenoxyphenyl)-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-2-imidodicarbonate |
| (VI)461018-34-a | 814-68-6Available | 2-Propenoyl chloride |
| (VII)461018-34-a | - | Di-tert-butyl [3-(4-phenoxyphenyl)-1-[(3R)-1-(prop-2-enoyl)piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-2-imidodicarbonate |
| (VIII)461018-34-a | 16466-61-8 | Di-tert-butyl hydrazine-1,2-dicarboxylate |
| (X)461018-34-a | - | N'-(4,5,6,7-Tetrahydro-1H-indole-1-carbonyl)-4,5,6,7-tetrahydro-1H-indole-1-carbohydrazide |
Frequently asked questions
What are the approved indications of Ibrutinib?
Approved indications include: Waldenström macroglobulinaemia, Chronic lymphocytic leukaemia, Mantle cell lymphoma, Graft-versus-host disease.
When does the Ibrutinib patent expire?
Based on public sources, the Ibrutinib patent expires in 2027.
How many synthesis routes are recorded for Ibrutinib?
33 synthesis routes are recorded; the shortest is 1 steps with / total yield. Intermediates in each route carry codes and CAS numbers.
Where can I buy Ibrutinib intermediates?
18 intermediate CAS of Ibrutinib 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 Ibrutinib 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