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芦比前列酮
Tier C — Watch / tradeLubiprostone
Sucampo
Originator
2006
First approval
-
Expiry (public)
$0.48B ▲
Peak sales
化学药
Type
Targets：CLCN2
Brand：Amitiza
Indications (approved)：便秘、阿片类药物引起的便秘、慢性特发性便秘
Regional status
US
批准上市
2006-01-31
EU
无进展
2010-12-01
China
批准上市
2023-06-27
Japan
批准上市
2012-06-29
Synthetic routes & intermediates5 routes
Originator routes × 1Optimised (non-patent) × 4Process 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 12 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| LUBI-001 | 118408-95-0 | (3aR,4S,5R,6aS)-5-((tetrahydro-2H-pyran-2-yl)oxy)-4-(((trimethylsilyl)oxy)methyl)hexahydro-2H-cyclopenta[b]furan-2-one |
| LUBI-002 | 69222-61-3 | (3aR,4S,5R,6aS)-4-(hydroxymethyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one |
| LUBI-003 | 32233-41-3 | (3aR,4R,5R,6aS)-2-oxo-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-4-carbaldehyde |
| LUBI-004 | 50889-46-8 | dimethyl (3,3-difluoro-2-oxoheptyl)phosphonate |
| LUBI-005 | 136790-72-2 | (3aR,4R,5R,6aS)-4-((E)-4,4-difluoro-3-oxooct-1-en-1-yl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one |
| LUBI-006 | 136790-73-3 | (3aR,4R,5R,6aS)-4-(4,4-difluoro-3-oxooctyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one |
| LUBI-007 | 201226-21-3 | (3aR,4R,5R,6aS)-4-(4,4-difluoro-3-hydroxyoctyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one |
| LUBI-008 | 201341-41-5 | (3aR,4R,5R,6aS)-4-(4,4-difluoro-3-hydroxyoctyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol |
| LUBI-009 | 50889-29-7 | (5-carboxypentyl)triphenylphosphonium bromide |
| LUBI-010 | 136790-75-5 | (Z)-7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoic acid |
| LUBI-011 | 136790-77-7 | benzyl (Z)-7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate |
| LUBI-012 | 136790-78-8 | benzyl (Z)-7-((1R,2R,3R)-2-(4,4-difluoro-3-oxooctyl)-5-oxo-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate |
| LUBI-013 | 136790-79-9 | benzyl (Z)-7-((1R,2R,3R)-2-(4,4-difluoro-3-oxooctyl)-3-hydroxy-5-oxocyclopentyl)hept-5-enoate |
| LUBI-014 | 136790-76-6 | 7-((1R,2R,3R)-2-(4,4-difluoro-3-oxooctyl)-3-hydroxy-5-oxocyclopentyl)heptanoic acid |
OptimisedRoute 2Steps 11 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| LUBI-004 | 50889-46-8 | dimethyl (3,3-difluoro-2-oxoheptyl)phosphonate |
| LUBI-010 | 136790-75-5 | (Z)-7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoic acid |
| LUBI-015 | - | (3aR,4S,5R,6aS)-2-oxo-4-(((trimethylsilyl)oxy)methyl)hexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate |
| LUBI-016 | 31752-99-5 | (3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate |
| LUBI-017 | 38754-71-1 | (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate |
| LUBI-018 | - | (3aR,4R,5R,6aS)-4-((E)-4,4-difluoro-3-oxooct-1-en-1-yl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate |
| LUBI-019 | - | (3aR,4R,5R,6aS)-4-(4,4-difluoro-3-oxooctyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate |
| LUBI-020 | - | (3aR,4R,5R,6aS)-4-(4,4-difluoro-3-hydroxyoctyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate |
| LUBI-021 | - | (3aR,4R,5R,6aS)-4-(3-((tert-butyldimethylsilyl)oxy)-4,4-difluorooctyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate |
| LUBI-022 | 201226-28-0 | (3aR,4R,5R,6aS)-4-(3-((tert-butyldimethylsilyl)oxy)-4,4-difluorooctyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one |
| LUBI-023 | 201341-43-7 | (3aR,4R,5R,6aS)-4-(3-((tert-butyldimethylsilyl)oxy)-4,4-difluorooctyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol |
| LUBI-024 | 148999-69-3 | (6-methoxy-6-oxohexyl)triphenylphosphonium bromide |
| LUBI-025 | 118583-11-2 | methyl (Z)-7-((1R,2R,3R,5S)-2-(3-((tert-butyldimethylsilyl)oxy)-4,4-difluorooctyl)-5-hydroxy-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate |
| LUBI-026 | 118583-12-3 | methyl (Z)-7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate |
OptimisedRoute 3Steps 11 · Total yield 0.32 g
| Code | CAS No. | Intermediate |
|---|---|---|
| LUBI-027 | 667-27-6 | ethyl 2-bromo-2,2-difluoroacetate |
| LUBI-028 | 123-72-8 | butyraldehyde |
| LUBI-029 | 181825-79-6 | ethyl 2,2-difluoro-3-hydroxyhexanoate |
| LUBI-030 | 1346523-54-3 | ethyl (E)-2,2-difluorohex-3-enoate |
| LUBI-031 | 1372609-18-1 | (E)-4,4-difluoro-1-(trimethylsilyl)oct-5-en-1-yn-3-one |
| LUBI-032 | 1372609-19-2 | (E)-4,4-difluorooct-5-en-1-yn-3-ol |
| LUBI-033 | 1372609-22-7 | (1E,5E)-4,4-difluoro-1-(tributylstannyl)octa-1,5-dien-3-ol |
| LUBI-034 | 1372609-23-8 | tributyl((1E,5E)-4,4-difluoro-3-((4-methoxybenzyl)oxy)octa-1,5-dien-1-yl)stannane |
| LUBI-035 | 474944-36-0 | isopropyl (R,Z)-7-(3-((tert-butyldimethylsilyl)oxy)-5-oxocyclopent-1-en-1-yl)hept-5-enoate |
| LUBI-036 | 1372609-25-0 | isopropyl (Z)-7-((1R,2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2-((1E,5E)-4,4-difluoro-3-((4-methoxybenzyl)oxy)octa-1,5-dien-1-yl)-5-oxocyclopentyl)hept-5-enoate |
| LUBI-037 | 1372609-14-7 | isopropyl 7-((1R,2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2-(4,4-difluoro-3-hydroxyoctyl)-5-oxocyclopentyl)heptanoate |
| LUBI-038 | 1372609-15-8 | isopropyl 7-((1R,2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2-(4,4-difluoro-3-oxooctyl)-5-oxocyclopentyl)heptanoate |
| LUBI-039 | 1372609-16-9 | 7-((1R,2R,3R)-3-((tert-butyldimethylsilyl)oxy)-2-(4,4-difluoro-3-oxooctyl)-5-oxocyclopentyl)heptanoic acid |
OptimisedRoute 4Steps 9 · Total yield /
| Code | CAS No. | Intermediate |
|---|---|---|
| LUBI-004 | 50889-46-8 | dimethyl (3,3-difluoro-2-oxoheptyl)phosphonate |
| LUBI-009 | 50889-29-7 | (5-carboxypentyl)triphenylphosphonium bromide |
| LUBI-040 | 32233-40-2 | (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one |
| LUBI-041 | 65025-94-7 | (3aR,4S,5R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one |
| LUBI-042 | 1384885-37-3 | (3aR,4S,5R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-5-((4-methoxybenzyl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one |
| LUBI-043 | 1384885-25-9 | (3aR,4S,5R,6aS)-4-(((tert-butyldimethylsilyl)oxy)methyl)-5-((4-methoxybenzyl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol |
| LUBI-044 | 1384885-27-1 | (Z)-7-((1R,2S,3R,5S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxy-3-((4-methoxybenzyl)oxy)cyclopentyl)hept-5-enoic acid |
| LUBI-045 | 1431770-99-8 | benzyl (Z)-7-((1R,2S,3R,5S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxy-3-((4-methoxybenzyl)oxy)cyclopentyl)hept-5-enoate |
| LUBI-046 | 1210039-39-6 | benzyl (Z)-7-((1R,2S,3R,5S)-5-hydroxy-2-(hydroxymethyl)-3-((4-methoxybenzyl)oxy)cyclopentyl)hept-5-enoate |
| LUBI-047 | - | benzyl (Z)-7-((1R,2R,3R,5S)-2-formyl-5-hydroxy-3-((4-methoxybenzyl)oxy)cyclopentyl)hept-5-enoate |
| LUBI-048 | 1210039-41-0 | benzyl (Z)-7-((1R,2R,3R)-2-((E)-4,4-difluoro-3-oxooct-1-en-1-yl)-3-((4-methoxybenzyl)oxy)-5-oxocyclopentyl)hept-5-enoate |
OptimisedRoute 5Steps 8 · Total yield 4.1 g
| Code | CAS No. | Intermediate |
|---|---|---|
| LUBI-004 | 50889-46-8 | dimethyl (3,3-difluoro-2-oxoheptyl)phosphonate |
| LUBI-009 | 50889-29-7 | (5-carboxypentyl)triphenylphosphonium bromide |
| LUBI-040 | 32233-40-2 | (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one |
| LUBI-046 | 1210039-39-6 | benzyl (Z)-7-((1R,2S,3R,5S)-5-hydroxy-2-(hydroxymethyl)-3-((4-methoxybenzyl)oxy)cyclopentyl)hept-5-enoate |
| LUBI-048 | 1210039-41-0 | benzyl (Z)-7-((1R,2R,3R)-2-((E)-4,4-difluoro-3-oxooct-1-en-1-yl)-3-((4-methoxybenzyl)oxy)-5-oxocyclopentyl)hept-5-enoate |
| LUBI-049 | 39746-00-4 | (3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate |
| LUBI-050 | 2186-92-7 | 1-(dimethoxymethyl)-4-methoxybenzene |
| LUBI-051 | 1210039-33-0 | (4aS,4bR,7aS,8aR)-2-(4-methoxyphenyl)hexahydrofuro[3',2':3,4]cyclopenta[1,2-d][1,3]dioxin-6(4H)-one |
| LUBI-052 | 1210039-35-2 | (3aR,4S,5R,6aS)-4-(hydroxymethyl)-5-((4-methoxybenzyl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol |
| LUBI-053 | 1210039-37-4 | (Z)-7-((1R,2S,3R,5S)-5-hydroxy-2-(hydroxymethyl)-3-((4-methoxybenzyl)oxy)cyclopentyl)hept-5-enoic acid |
| LUBI-054 | 1210039-40-9 | benzyl (Z)-7-((1R,2R,3R)-2-formyl-3-((4-methoxybenzyl)oxy)-5-oxocyclopentyl)hept-5-enoate |
Frequently asked questions
What are the approved indications of Lubiprostone?
Approved indications include: 便秘, 阿片类药物引起的便秘, 慢性特发性便秘.
When does the Lubiprostone patent expire?
No public expiry year is available for Lubiprostone yet; this page updates once verified.
How many synthesis routes are recorded for Lubiprostone?
5 synthesis routes are recorded; the shortest is 8 steps with 4.1 g total yield. Intermediates in each route carry codes and CAS numbers.
Where can I buy Lubiprostone intermediates?
All intermediates in Lubiprostone routes have CAS profiles — you can submit an RFQ per CAS and it enters the Unibest matching pool.
How do I get a quote for Lubiprostone 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) · 2026-09-24