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CAS 57-13-6
ureaCarbamideUreaIsourea
Codes: AVAN-035, Tenofovir disoproxil phosphate-043, ROSU-047, OLMU-002, Ambroxol- 035
Application context (from source-drug indications)
Erectile dysfunctionAvanafilHIV infectionLamivudine/Tenofovir Disoproxil FumarateChronic hepatitis BLamivudine/Tenofovir Disoproxil FumarateHIV infectionEfavirenz/Lamivudine/Tenofovir Disoproxil FumarateHypertensionFimasartan potassium trihydrate/Rosuvastatin calciumDyslipidaemiaFimasartan potassium trihydrate/Rosuvastatin calciumNon-small cell lung cancerOlmutinibHypertensionRosuvastatin Calcium/TelmisartanHyperlipidaemiaRosuvastatin Calcium/TelmisartanHIV infectionEmtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateChronic bronchitisRoxithromycin/Ambroxol HydrochlorideBronchitisRoxithromycin/Ambroxol HydrochlorideRespiratory tract infectionRoxithromycin/Ambroxol HydrochloridePneumoniaRoxithromycin/Ambroxol HydrochlorideTracheitisRoxithromycin/Ambroxol HydrochlorideBacterial infectionRoxithromycin/Ambroxol HydrochlorideHepatitis BTenofovir disoproxil phosphateHomozygous familial hypercholesterolaemiaRosuvastatin CalciumHeterozygous familial hypercholesterolaemiaRosuvastatin CalciumHyperlipoproteinaemia type IIIRosuvastatin CalciumAtherosclerosisRosuvastatin CalciumHyperlipoproteinaemia type IIRosuvastatin CalciumHypercholesterolaemiaRosuvastatin CalciumAnaesthesiaAmbroxol HydrochloridePharyngitisAmbroxol HydrochlorideRespiratory diseaseAmbroxol HydrochlorideBronchitisAmbroxol HydrochlorideParkinson's diseaseAmbroxol HydrochlorideParkinsonismAmbroxol Hydrochloride
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Avanafil | Tier C — Watch / trade | 2028 |
| Lamivudine/Tenofovir Disoproxil Fumarate | Tier C — Watch / trade | - |
| Efavirenz/Lamivudine/Tenofovir Disoproxil Fumarate | Tier C — Watch / trade | - |
| Fimasartan potassium trihydrate/Rosuvastatin calcium | Tier C — Watch / trade | - |
| Olmutinib | Tier C — Watch / trade | - |
| Rosuvastatin Calcium/Telmisartan | Tier C — Watch / trade | - |
| Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil Fumarate | Tier B — Position early | - |
| Roxithromycin/Ambroxol Hydrochloride | Tier C — Watch / trade | - |
| Tenofovir disoproxil phosphate | Tier C — Watch / trade | - |
| Rosuvastatin Calcium | Tier B — Position early | - |
| Ambroxol Hydrochloride | Tier C — Watch / trade | - |
Position in synthesis routes (up/downstream chain)
Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.
(S)-pyrrolidin-2-ylmethanol→ethyl (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylate→pyrimidin-2-ylmethanamine→ethyl 2-cyanoacetate→urea→ethyl (E)-2-cyano-3-ureidoacrylate→ethyl 6-amino-2-oxo-1,2-dihydropyrimidine-5-carboxylate→2-chloro-4-(chloromethyl)-1-methoxybenzene→ethyl 6-((3-chloro-4-methoxybenzyl)amino)-2-oxo-1,2-dihydropyrimidine-5-carboxylate
(R)-1-(6-Amino-9H-purin-9-yl)propan-2-ol→(Diethoxyphosphoryl)methyl 4-methylbenzene-1-sulfonate→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→Carbamide→Thiocarbamide→Guanidine→Ethoxy(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→(Ethylsulfanyl)(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→(Ethylamino)(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate
(R)-1-(6-Amino-9H-purin-9-yl)propan-2-ol→(Diethoxyphosphoryl)methyl 4-methylbenzene-1-sulfonate→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→Carbamide→Thiocarbamide→Guanidine→Ethoxy(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→(Ethylsulfanyl)(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→(Ethylamino)(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate
4-fluorobenzaldehyde→N-(5-((diphenylphosphoryl)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide→N-(4-(4-fluorophenyl)-5-((E)-2-((2S,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)vinyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide→methyl 4-methyl-3-oxopentanoate→urea→methyl 4-(4-fluorophenyl)-6-isopropyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate→methyl 4-(4-fluorophenyl)-2-hydroxy-6-isopropylpyrimidine-5-carboxylate→N-methylmethanesulfonamide→methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidine-5-carboxylate→N-(4-(4-fluorophenyl)-5-(hydroxymethyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide→N-(5-(bromomethyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide→tert-butyl (4S,6S)-6-formyl-2,2-dimethyl-1,3-dioxane-4-carboxylate→tert-butyl (4S,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxane-4-carboxylate
Methyl 3-aminothiophene-2-carboxylate→Urea→Thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione→2,4-dichlorothieno[3,2-d]pyrimidine→3-nitrophenol→2-chloro-4-(3-nitrophenoxy)thieno[3,2-d]pyrimidine→4-(4-methylpiperazin-1-yl)aniline→N-(4-(4-methylpiperazin-1-yl)phenyl)-4-(3-nitrophenoxy)thieno[3,2-d]pyrimidin-2-amine→4-(3-aminophenoxy)-N-(4-(4-methylpiperazin-1-yl)phenyl)thieno[3,2-d]pyrimidin-2-amine→Acryloyl chloride
4-fluorobenzaldehyde→N-(5-((diphenylphosphoryl)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide→N-(4-(4-fluorophenyl)-5-((E)-2-((2S,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)vinyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide→methyl 4-methyl-3-oxopentanoate→urea→methyl 4-(4-fluorophenyl)-6-isopropyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate→methyl 4-(4-fluorophenyl)-2-hydroxy-6-isopropylpyrimidine-5-carboxylate→N-methylmethanesulfonamide→methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidine-5-carboxylate→N-(4-(4-fluorophenyl)-5-(hydroxymethyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide→N-(5-(bromomethyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide→tert-butyl (4S,6S)-6-formyl-2,2-dimethyl-1,3-dioxane-4-carboxylate→tert-butyl (4S,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxane-4-carboxylate
Emtricitabine/Rilpivirine Hydrochloride/Tenofovir Disoproxil FumarateOptimised routesteps: 3total yield: /
(R)-1-(6-Amino-9H-purin-9-yl)propan-2-ol→(Diethoxyphosphoryl)methyl 4-methylbenzene-1-sulfonate→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→Carbamide→Thiocarbamide→Guanidine→Ethoxy(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→(Ethylsulfanyl)(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→(Ethylamino)(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate
(R)-1-(6-Amino-9H-purin-9-yl)propan-2-ol→(Diethoxyphosphoryl)methyl 4-methylbenzene-1-sulfonate→(R)-9-[2-(Diethylphosphonomethoxy)propyl] adenine→Carbamide→Thiocarbamide→Guanidine→Ethoxy(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→(Ethylsulfanyl)(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate→(Ethylamino)(imino)methanaminium ethyl ([[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy]methyl)phosphonate
4-fluorobenzaldehyde→N-(5-((diphenylphosphoryl)methyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide→N-(4-(4-fluorophenyl)-5-((E)-2-((2S,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)vinyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide→methyl 4-methyl-3-oxopentanoate→urea→methyl 4-(4-fluorophenyl)-6-isopropyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate→methyl 4-(4-fluorophenyl)-2-hydroxy-6-isopropylpyrimidine-5-carboxylate→N-methylmethanesulfonamide→methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidine-5-carboxylate→N-(4-(4-fluorophenyl)-5-(hydroxymethyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide→N-(5-(bromomethyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide→tert-butyl (4S,6S)-6-formyl-2,2-dimethyl-1,3-dioxane-4-carboxylate→tert-butyl (4S,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxane-4-carboxylate
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