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Ramipril
Tier C — Watch / tradeRamipril
Pfizer Inc.
Originator
1991
First approval
-
Expiry (public)
$0.52B ▲
Peak sales
Small molecule
Type
Targets：ACE
Brand：Ramace, Triatec, Carasel, Unipril, Delix, Tritace, Altac
Indications (approved)：Hypertension, Nephropathy, Myocardial infarction, Heart failure, Stroke
Regional status
US
Phase II
2000-06-01
EU
Discontinued
2006-10-01
China
Approved
2000-12-15
Japan
-
Synthetic routes & intermediates15 routes
Originator routes × 0Optimised (non-patent) × 12Process routes × 3
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.
OptimisedRoute 2Steps 4 · Total yield /
Ramipril-00387269-85-0Ramipril-00887269-87-2Ramipril-0101375192-85-0Ramipril-011811420-40-3Ramipril-0121375193-05-7Ramipril-013—Ramipril-0141375193-06-8API · Ramipril
| Code | CAS No. | Intermediate |
|---|---|---|
| Ramipril-003 | 87269-85-0 | (Methyl 2-(acetylamino)-3-(2-oxocyclopentyl)propanoate) |
| Ramipril-008 | 87269-87-2 | Benzyl (2S,3aS,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride |
| Ramipril-010 | 1375192-85-0 | N-Acetyl-3-(2-oxocyclopentyl)-L-alanine |
| Ramipril-011 | 811420-40-3 | (2S)-2,3,3a,4,5,6-Hexahydrocyclopenta[b]pyrrole-2-carboxylic acid hydrochloride |
| Ramipril-012 | 1375193-05-7 | (2S)-2,3,3a,4,5,6-Hexahydrocyclopenta[b]pyrrole-2-carboxylic acid 4-methylbenzenesulfonate |
| Ramipril-013 | - | (2S,3aR,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylic acid hydrochloride |
| Ramipril-014 | 1375193-06-8 | (2S,3aS,6aS)-Octahydrocyclopenta[b]pyrrole-2-carboxylic acid 4-methylbenzenesulfonate |
OptimisedRoute 3Steps 8 · Total yield 65g(Ramipril-010)
Ramipril-00487269-86-1Ramipril-015—Ramipril-016—Ramipril-0172231630-58-1Ramipril-018—Ramipril-019—Ramipril-020—Ramipril-021495-69-2Ramipril-022—Ramipril-023—Ramipril-024—Ramipril-025—Ramipril-026—Ramipril-027—Ramipril-028—Ramipril-029—API · Ramipril
| Code | CAS No. | Intermediate |
|---|---|---|
| Ramipril-004 | 87269-86-1 | (2S,3aS,6aS)-Octahydrocyclopenta[b]pyrrole-2-carboxylic acid hydrochloride |
| Ramipril-015 | - | 2-Acetamidoacetic acid |
| Ramipril-016 | - | Formyldimethylamine |
| Ramipril-017 | 2231630-58-1 | 4-[(Dimethylamino)methylidene]-2-methyl-1,3-oxazol-5(4H)-one |
| Ramipril-018 | - | Sodium (2-methyl-5-oxo-1,3-oxazol-4(5H)-ylidene)methanolate |
| Ramipril-019 | - | (2-Methyl-5-oxo-1,3-oxazol-4(5H)-ylidene)methyl acetate |
| Ramipril-020 | - | 4-(Ethoxymethylidene)-2-phenyl-1,3-oxazol-5(4H)-one |
| Ramipril-021 | 495-69-2 | 2-(Phenylformamido)Acetic Acid |
| Ramipril-022 | - | (Diethoxymethoxy)ethane |
| Ramipril-023 | - | 1-Morpholinocyclopentene |
| Ramipril-024 | - | 2-Methyl-4-[[2-(morpholin-4-yl)cyclopent-1-en-1-yl]methylidene]-1,3-oxazol-5(4H)-one |
| Ramipril-025 | - | 4-[[2-(Morpholin-4-yl)cyclopent-1-en-1-yl]methylidene]-2-phenyl-1,3-oxazol-5(4H)-one |
| Ramipril-026 | - | Methyl 2-benzamido-3-[2-(morpholin-4-yl)cyclopent-1-en-1-yl]prop-2-enoate |
| Ramipril-027 | - | Methyl 2-acetamido-3-[2-(morpholin-4-yl)cyclopent-1-en-1-yl]prop-2-enoate |
| Ramipril-028 | - | Methyl N-benzoyl-3-[2-(morpholin-4-yl)cyclopent-1-en-1-yl]-L-alaninate |
| Ramipril-029 | - | Methyl N-acetyl-3-[2-(morpholin-4-yl)cyclopent-1-en-1-yl]-L-alaninate |
OptimisedRoute 4Steps 2 · Total yield /
Ramipril-030—Ramipril-00887269-87-2Ramipril-03184793-24-8Ramipril-00787269-88-3API · Ramipril
| Code | CAS No. | Intermediate |
|---|---|---|
| Ramipril-030 | - | Benzyl (2S,3aS,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylate |
| Ramipril-008 | 87269-87-2 | Benzyl (2S,3aS,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride |
| Ramipril-031 | 84793-24-8 | Ethyl (2S)-2-[(4S)-4-methyl-2,5-dioxo-1,3-oxazolidin-3-yl]-4-phenylbutanoate |
| Ramipril-007 | 87269-88-3 | (2S,3aS,6aS)-1-[N-[1(S)-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]perhydrocyclopenta[b]pyrrole-2-carboxylic acid |
OptimisedRoute 5Steps 1 · Total yield /
Ramipril-032—Ramipril-033—API · Ramipril
| Code | CAS No. | Intermediate |
|---|---|---|
| Ramipril-032 | - | (2S)-octahydrocyclopenta[b]pyrrole-2-carboxylic acid |
| Ramipril-033 | - | (2S,3aS,6aS)-Octahydrocyclopenta[b]pyrrole-2-carboxylic acid |
OptimisedRoute 6Steps 7 · Total yield 19g(Ramipril (Free))
Ramipril-034859799-38-5Ramipril-001—Ramipril-035—Ramipril-036—Ramipril-0371030838-82-4Ramipril-038812630-31-2Ramipril-033—Ramipril-039—Ramipril-040172542-27-7Ramipril-04184793-24-8Ramipril-00787269-88-3API · Ramipril
| Code | CAS No. | Intermediate |
|---|---|---|
| Ramipril-034 | 859799-38-5 | methyl 3-chloro-2-(2-phenylacetamido)propanoate |
| Ramipril-001 | - | 1-(1-Cyclopentenyl)pyrrolidine |
| Ramipril-035 | - | methyl 3-(2-oxocyclopentyl)-2-(2-phenylacetamido)propanoate |
| Ramipril-036 | - | 3-(2-oxocyclopentyl)-2-(2-phenylacetamido)propanoic acid |
| Ramipril-037 | 1030838-82-4 | 3-(2-Oxocyclopentyl)-L-alanine |
| Ramipril-038 | 812630-31-2 | (2S)-2,3,3a,4,5,6-Hexahydrocyclopenta[b]pyrrole-2-carboxylic acid |
| Ramipril-033 | - | (2S,3aS,6aS)-Octahydrocyclopenta[b]pyrrole-2-carboxylic acid |
| Ramipril-039 | - | 1-Phenylmethanol |
| Ramipril-040 | 172542-27-7 | N'-[(1E)-{6-[(2S)-2-hydroxypropyl]-2H-1,3-benzodioxol-5-yl}(4-nitrophenyl)methylidene]acetohydrazide |
| Ramipril-041 | 84793-24-8 | Ethyl (2S)-2-[(4S)-4-methyl-2,5-dioxo-1,3-oxazolidin-3-yl]-4-phenylbutanoate |
| Ramipril-007 | 87269-88-3 | (2S,3aS,6aS)-1-[N-[1(S)-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]perhydrocyclopenta[b]pyrrole-2-carboxylic acid |
OptimisedRoute 7Steps 4 · Total yield 27.3g(Ramipril (Free))
Ramipril-006—Ramipril-042—Ramipril-043957299-56-8Ramipril-04184793-24-8Ramipril-030—Ramipril-00787269-88-3API · Ramipril
| Code | CAS No. | Intermediate |
|---|---|---|
| Ramipril-006 | - | N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine |
| Ramipril-042 | - | Carbonochloridic acid ethyl ester |
| Ramipril-043 | 957299-56-8 | ethyl (2S)-2-[(ethoxycarbonyl)[(2S)-1-[(ethoxycarbonyl)oxy]-1-oxopropan-2-yl]amino]-4-phenylbutanoate |
| Ramipril-041 | 84793-24-8 | Ethyl (2S)-2-[(4S)-4-methyl-2,5-dioxo-1,3-oxazolidin-3-yl]-4-phenylbutanoate |
| Ramipril-030 | - | Benzyl (2S,3aS,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylate |
| Ramipril-007 | 87269-88-3 | (2S,3aS,6aS)-1-[N-[1(S)-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]perhydrocyclopenta[b]pyrrole-2-carboxylic acid |
OptimisedRoute 8Steps 9 · Total yield 4.56g(Ramipril (Free))
Ramipril-0441143952-13-9Ramipril-0451143952-11-7Ramipril-001—Ramipril-0461143952-17-3Ramipril-0471143952-08-2Ramipril-00387269-85-0Ramipril-0371030838-82-4Ramipril-033—Ramipril-048852546-84-0Ramipril-049114192-42-6Ramipril-006—API · Ramipril
| Code | CAS No. | Intermediate |
|---|---|---|
| Ramipril-044 | 1143952-13-9 | Propyl L-serinate hydrochloride |
| Ramipril-045 | 1143952-11-7 | N-Acetyl-3-chloro-L-alanine propyl ester |
| Ramipril-001 | - | 1-(1-Cyclopentenyl)pyrrolidine |
| Ramipril-046 | 1143952-17-3 | N-Acetyl-3-(2-oxocyclopentyl)alanine propyl ester |
| Ramipril-047 | 1143952-08-2 | N-Carbamoyl-3-(2-oxocyclopentyl)alanine |
| Ramipril-003 | 87269-85-0 | (Methyl 2-(acetylamino)-3-(2-oxocyclopentyl)propanoate) |
| Ramipril-037 | 1030838-82-4 | 3-(2-Oxocyclopentyl)-L-alanine |
| Ramipril-033 | - | (2S,3aS,6aS)-Octahydrocyclopenta[b]pyrrole-2-carboxylic acid |
| Ramipril-048 | 852546-84-0 | Benzyl (2S,3aS,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylate 4-methylbenzenesulfonate |
| Ramipril-049 | 114192-42-6 | Ethyl (2S)-2-[[(2S)-1-chloro-1-oxopropan-2-yl]amino]-4-phenylbutanoate hydrochloride |
| Ramipril-006 | - | N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine |
OptimisedRoute 9Steps 6 · Total yield 11.8g(Ramipril (Free))
Ramipril-0501030838-88-0Ramipril-0371030838-82-4Ramipril-033—Ramipril-00887269-87-2Ramipril-030—Ramipril-049114192-42-6Ramipril-006—API · Ramipril
| Code | CAS No. | Intermediate |
|---|---|---|
| Ramipril-050 | 1030838-88-0 | 5-[(2-Oxocyclopentyl)methyl]imidazolidine-2,4-dione |
| Ramipril-037 | 1030838-82-4 | 3-(2-Oxocyclopentyl)-L-alanine |
| Ramipril-033 | - | (2S,3aS,6aS)-Octahydrocyclopenta[b]pyrrole-2-carboxylic acid |
| Ramipril-008 | 87269-87-2 | Benzyl (2S,3aS,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride |
| Ramipril-030 | - | Benzyl (2S,3aS,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylate |
| Ramipril-049 | 114192-42-6 | Ethyl (2S)-2-[[(2S)-1-chloro-1-oxopropan-2-yl]amino]-4-phenylbutanoate hydrochloride |
| Ramipril-006 | - | N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine |
OptimisedRoute 10Steps 1 · Total yield /
Ramipril-0511342316-06-6Ramipril-0521342316-08-8API · Ramipril
| Code | CAS No. | Intermediate |
|---|---|---|
| Ramipril-051 | 1342316-06-6 | Methyl (2Z)-2-(benzoylamino)-3-(2-chlorocyclopent-1-en-1-yl)acrylate |
| Ramipril-052 | 1342316-08-8 | Methyl N-benzoyl-3-(2-chlorocyclopent-1-en-1-yl)-L-alaninate |
OptimisedRoute 11Steps 1 · Total yield 219.3g(Ramipril-055)
Ramipril-0531803175-84-9Ramipril-0521342316-08-8Ramipril-054811420-39-0Ramipril-0551342316-12-4API · Ramipril
| Code | CAS No. | Intermediate |
|---|---|---|
| Ramipril-053 | 1803175-84-9 | Methyl N-acetyl-3-(2-chlorocyclopent-1-en-1-yl)-L-alaninate |
| Ramipril-052 | 1342316-08-8 | Methyl N-benzoyl-3-(2-chlorocyclopent-1-en-1-yl)-L-alaninate |
| Ramipril-054 | 811420-39-0 | Methyl N-acetyl-3-(2-oxocyclopentyl)-L-alaninate |
| Ramipril-055 | 1342316-12-4 | Methyl N-benzoyl-3-(2-oxocyclopentyl)-L-alaninate |
OptimisedRoute 12Steps 5 · Total yield 19.67g(Ramipril-008)
Ramipril-056—Ramipril-057—Ramipril-058—Ramipril-05923115-42-6Ramipril-06038524-17-3Ramipril-023—Ramipril-001—Ramipril-061—Ramipril-0621802682-26-3Ramipril-0631802682-27-4Ramipril-00887269-87-2API · Ramipril
| Code | CAS No. | Intermediate |
|---|---|---|
| Ramipril-056 | - | 2-Oxopropionic acid ethyl ester |
| Ramipril-057 | - | Acetamide |
| Ramipril-058 | - | Benzamide |
| Ramipril-059 | 23115-42-6 | Ethyl 2-acetamidoacrylate |
| Ramipril-060 | 38524-17-3 | Ethyl 2-(benzoylamino)acrylate |
| Ramipril-023 | - | 1-Morpholinocyclopentene |
| Ramipril-001 | - | 1-(1-Cyclopentenyl)pyrrolidine |
| Ramipril-061 | - | Cyclopentanone |
| Ramipril-062 | 1802682-26-3 | Ethyl N-acetyl-3-(2-oxocyclopentyl)alaninate |
| Ramipril-063 | 1802682-27-4 | Ethyl N-benzoyl-3-(2-oxocyclopentyl)alaninate |
| Ramipril-008 | 87269-87-2 | Benzyl (2S,3aS,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride |
OptimisedRoute 13Steps 6 · Total yield 3.33g(Ramipril-074)
Ramipril-064—Ramipril-065—Ramipril-066—Ramipril-0671239450-42-0Ramipril-0681239450-42-0Ramipril-06955299-57-5Ramipril-07024153-31-9Ramipril-06038524-17-3Ramipril-071—Ramipril-023—Ramipril-061—Ramipril-0721802682-27-4Ramipril-0631802682-27-4Ramipril-00387269-85-0Ramipril-073—Ramipril-074—API · Ramipril
| Code | CAS No. | Intermediate |
|---|---|---|
| Ramipril-064 | - | (+/-)-2-Amino-3-hydroxypropionic acid |
| Ramipril-065 | - | DL-Serine methyl ester hydrochloride |
| Ramipril-066 | - | Ethyl serinate hydrogen chloride |
| Ramipril-067 | 1239450-42-0 | 2-Benzamido-3-ethoxy-3-oxopropyl benzoate |
| Ramipril-068 | 1239450-42-0 | 2-Benzamido-3-ethoxy-3-oxopropyl benzoate |
| Ramipril-069 | 55299-57-5 | Ethyl N,O-diacetylserinate |
| Ramipril-070 | 24153-31-9 | Ethyl 2-benzamidoprop-2-enoate |
| Ramipril-060 | 38524-17-3 | Ethyl 2-(benzoylamino)acrylate |
| Ramipril-071 | - | 2-Acetamido-2-propenoic acid methyl ester |
| Ramipril-023 | - | 1-Morpholinocyclopentene |
| Ramipril-061 | - | Cyclopentanone |
| Ramipril-072 | 1802682-27-4 | Ethyl N-benzoyl-3-(2-oxocyclopentyl)alaninate |
| Ramipril-063 | 1802682-27-4 | Ethyl N-benzoyl-3-(2-oxocyclopentyl)alaninate |
| Ramipril-003 | 87269-85-0 | (Methyl 2-(acetylamino)-3-(2-oxocyclopentyl)propanoate) |
| Ramipril-073 | - | Benzyl octahydrocyclopenta[b]pyrrole-2-carboxylate hydrogen chloride |
| Ramipril-074 | - | Octahydrocyclopenta[b]pyrrole-2-carboxylic acid hydrogen chloride |
ProcessRoute 1Steps 7 · Total yield 18.5kg(Ramipril (Free))
Ramipril-001—Ramipril-00287333-22-0Ramipril-00387269-85-0Ramipril-00487269-86-1Ramipril-005—Ramipril-006—Ramipril-00787269-88-3Ramipril-00887269-87-2Ramipril-009—API · Ramipril
| Code | CAS No. | Intermediate |
|---|---|---|
| Ramipril-001 | - | 1-(1-Cyclopentenyl)pyrrolidine |
| Ramipril-002 | 87333-22-0 | (+/-)-Methyl 2-(Acetylamino)-3-chloropropionate |
| Ramipril-003 | 87269-85-0 | (Methyl 2-(acetylamino)-3-(2-oxocyclopentyl)propanoate) |
| Ramipril-004 | 87269-86-1 | (2S,3aS,6aS)-Octahydrocyclopenta[b]pyrrole-2-carboxylic acid hydrochloride |
| Ramipril-005 | - | Benzyl (2S,3aR,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylic acid hydrochloride |
| Ramipril-006 | - | N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine |
| Ramipril-007 | 87269-88-3 | (2S,3aS,6aS)-1-[N-[1(S)-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]perhydrocyclopenta[b]pyrrole-2-carboxylic acid |
| Ramipril-008 | 87269-87-2 | Benzyl (2S,3aS,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride |
| Ramipril-009 | - | Benzyl (2S,3aS,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylate sulfate |
ProcessRoute 14Steps 3 · Total yield /
Ramipril-075—Ramipril-076—Ramipril-077—Ramipril-078—API · Ramipril
| Code | CAS No. | Intermediate |
|---|---|---|
| Ramipril-075 | - | (S)-2-Amino-3-hydroxypropanoic acid |
| Ramipril-076 | - | L-Serine methyl ester hydrochloride |
| Ramipril-077 | - | Methyl 3-chloro-L-alaninate hydrogen chloride |
| Ramipril-078 | - | Methyl N-acetyl-3-chloro-D-alaninate |
ProcessRoute 15Steps 3 · Total yield 723.11g(Ramipril (Free))
Ramipril-006—Ramipril-079108430-65-5Ramipril-00487269-86-1Ramipril-0802738483-63-9API · Ramipril
| Code | CAS No. | Intermediate |
|---|---|---|
| Ramipril-006 | - | N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine |
| Ramipril-079 | 108430-65-5 | N-(tert-Butoxycarbonyl)-N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanine |
| Ramipril-004 | 87269-86-1 | (2S,3aS,6aS)-Octahydrocyclopenta[b]pyrrole-2-carboxylic acid hydrochloride |
| Ramipril-080 | 2738483-63-9 | (2S,3aS,6aS)-1-[(2S)-2-[(tert-Butoxycarbonyl)[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid |
Frequently asked questions
What are the approved indications of Ramipril?
Approved indications include: Hypertension, Nephropathy, Myocardial infarction, Heart failure, Stroke.
When does the Ramipril patent expire?
No public expiry year is available for Ramipril yet; this page updates once verified.
How many synthesis routes are recorded for Ramipril?
15 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 Ramipril intermediates?
All intermediates in Ramipril 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 Ramipril 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