IT1229853B - Mono:phosphorylated l-dopa ester(s) with high bio:availability - Google Patents
Mono:phosphorylated l-dopa ester(s) with high bio:availabilityInfo
- Publication number
- IT1229853B IT1229853B IT8920209A IT2020989A IT1229853B IT 1229853 B IT1229853 B IT 1229853B IT 8920209 A IT8920209 A IT 8920209A IT 2020989 A IT2020989 A IT 2020989A IT 1229853 B IT1229853 B IT 1229853B
- Authority
- IT
- Italy
- Prior art keywords
- solvent
- alkyl
- ester
- optionally substituted
- formula
- Prior art date
Links
- -1 Mono:phosphorylated l-dopa ester Chemical class 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 230000000865 phosphorylative effect Effects 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000004471 Glycine Substances 0.000 abstract 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 abstract 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 abstract 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 abstract 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 abstract 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 abstract 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 abstract 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 235000004279 alanine Nutrition 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 abstract 1
- 235000008206 alpha-amino acids Nutrition 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical group OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 1
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical class OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 150000008282 halocarbons Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229960000310 isoleucine Drugs 0.000 abstract 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 229920000137 polyphosphoric acid Polymers 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 102220223237 rs766143485 Human genes 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 1
- 239000004474 valine Substances 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Compound of formula (I) and its pharmaceutically acceptable acid or base salts is new. In (I) the assymetric C atom marked with an asterisk has 5 configuration; either R or R1 is H or R40P(O)(OH)-(where R4 is H, phenyl, alkylphenyl or (1-6C) alkyl optionally substituted); R2 is straight or branched (1-4C) alkyl, (3-6) cycloalkyl or a phenylalkyl with (1-4C) in the alkyl portion optionally substituted. R3 is H or an acyl group of a natural alpha-aminoacid, e.g. glycine, alanine, valine, leucine, isoleucine, etc. (I) is prepared by phosphorylating an L-dopa ester of formula (I) where R and R1 are H, optionally protected at one hydroxy phenol group and, when R3 is H, at the amino group, in a solvent at a temperature of -80 to +100 deg.C, then removing the protecting groups, if any. The solvent can be the phosphorylating agent or an inert organic solvent, e.g. hydrocarbon, halocarbon, ether, ester, amide, etc. The phosphorylating agent is e.g. orthophosphoric acid, polyphosphoric acid, phosphorous pentoxide, chlorophosphoric acids, etc. (I) may be administered as a solid, e.g. tablet, granules, or as a liquid, e.g. syrup, emulsion. The preferred administration is orally. The doses are 100 mg to 5 g per day.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8920209A IT1229853B (en) | 1989-04-20 | 1989-04-20 | Mono:phosphorylated l-dopa ester(s) with high bio:availability |
| AT90200937T ATE118216T1 (en) | 1989-04-20 | 1990-04-17 | DOPAMINE MEDICINE PRECURSOR. |
| EP90200937A EP0393781B1 (en) | 1989-04-20 | 1990-04-17 | Dopamine pro-drug |
| ES90200937T ES2070994T3 (en) | 1989-04-20 | 1990-04-17 | DOPAMINE PROFARMACO. |
| DE69016688T DE69016688T2 (en) | 1989-04-20 | 1990-04-17 | Dopamine drug precursor. |
| US07/512,211 US5073547A (en) | 1989-04-20 | 1990-04-20 | Dopamine pro-drug |
| JP2103274A JPH02292290A (en) | 1989-04-20 | 1990-04-20 | Dopamine prodrug |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT8920209A IT1229853B (en) | 1989-04-20 | 1989-04-20 | Mono:phosphorylated l-dopa ester(s) with high bio:availability |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IT8920209A0 IT8920209A0 (en) | 1989-04-20 |
| IT1229853B true IT1229853B (en) | 1991-09-13 |
Family
ID=11164783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT8920209A IT1229853B (en) | 1989-04-20 | 1989-04-20 | Mono:phosphorylated l-dopa ester(s) with high bio:availability |
Country Status (1)
| Country | Link |
|---|---|
| IT (1) | IT1229853B (en) |
-
1989
- 1989-04-20 IT IT8920209A patent/IT1229853B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| IT8920209A0 (en) | 1989-04-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TA | Fee payment date (situation as of event date), data collected since 19931001 |
Effective date: 19950313 |