WO1995026325B1 - Enhancement of the efficacy of drugs by deuteration - Google Patents
Enhancement of the efficacy of drugs by deuterationInfo
- Publication number
- WO1995026325B1 WO1995026325B1 PCT/CA1995/000154 CA9500154W WO9526325B1 WO 1995026325 B1 WO1995026325 B1 WO 1995026325B1 CA 9500154 W CA9500154 W CA 9500154W WO 9526325 B1 WO9526325 B1 WO 9526325B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- nifedipine
- solution
- dihydropyridine
- deuterated
- compound
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims abstract 4
- 229940079593 drugs Drugs 0.000 title abstract 3
- HYIMSNHJOBLJNT-UHFFFAOYSA-N Nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 claims abstract 16
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims abstract 9
- 229960001597 Nifedipine Drugs 0.000 claims abstract 7
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims abstract 7
- 238000001346 gas chromatography-isotope ratio mass spectrometry Methods 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims 13
- YNGDWRXWKFWCJY-UHFFFAOYSA-N dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims 7
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N Trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims 6
- 229910052805 deuterium Inorganic materials 0.000 claims 6
- 125000004431 deuterium atoms Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- XLYOFNOQVPJJNP-ZSJDYOACSA-N water-d2 Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 claims 6
- HEDRZPFGACZZDS-MICDWDOJSA-N cdcl3 Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims 3
- 238000007710 freezing Methods 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 238000007789 sealing Methods 0.000 claims 3
- 230000000155 isotopic Effects 0.000 claims 2
- HTIQEAQVCYTUBX-UHFFFAOYSA-N Amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 claims 1
- 229960003580 Felodipine Drugs 0.000 claims 1
- RZTAMFZIAATZDJ-UHFFFAOYSA-N Felodipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-UHFFFAOYSA-N 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 229960001783 Nicardipine Drugs 0.000 claims 1
- ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 claims 1
- 229950000109 Niludipine Drugs 0.000 claims 1
- VZWXXKDFACOXNT-UHFFFAOYSA-N Niludipine Chemical compound CCCOCCOC(=O)C1=C(C)NC(C)=C(C(=O)OCCOCCC)C1C1=CC=CC([N+]([O-])=O)=C1 VZWXXKDFACOXNT-UHFFFAOYSA-N 0.000 claims 1
- 229960000715 Nimodipine Drugs 0.000 claims 1
- UIAGMCDKSXEBJQ-UHFFFAOYSA-N Nimodipine Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 UIAGMCDKSXEBJQ-UHFFFAOYSA-N 0.000 claims 1
- 229960000227 Nisoldipine Drugs 0.000 claims 1
- 229960005425 Nitrendipine Drugs 0.000 claims 1
- PVHUJELLJLJGLN-UHFFFAOYSA-N Nitrendipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC([N+]([O-])=O)=C1 PVHUJELLJLJGLN-UHFFFAOYSA-N 0.000 claims 1
- 229960000528 amlodipine Drugs 0.000 claims 1
- 230000003276 anti-hypertensive Effects 0.000 claims 1
- 239000002220 antihypertensive agent Substances 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 238000001514 detection method Methods 0.000 claims 1
- VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 claims 1
- 239000002547 new drug Substances 0.000 abstract 2
- 230000002708 enhancing Effects 0.000 abstract 1
- 230000001077 hypotensive Effects 0.000 abstract 1
Abstract
A method of enhancing the efficiency and increasing the duration of action of drugs (e.g. dihydropyridines) and particularly of nifedipine wherein one or more hydrogen atoms are deuterated and wherein the deuterated nifedipine has unexpectedly improved hypotensive properties when used in much lower concentrations than nifedipine per se. A method for determining the identity and bioequivalency of a new drug is also disclosed wherein the molecular and isotope structure of a new drug is determined by gas chromatography-isotope ratio mass spectrometry and compared with the molecular and isotope structure of a known human drug.
Claims
1. A compound wherein at least one of the hydrogen atoms is replaced with a deuterium atom, wherein said compound is a dihydropyridine.
2. The compound according to claim 1, wherein said dihydropyridine is deuterated nifedipine having the formula
wherein at least one of the hydrogen atoms is a deuterium atom.
3. The compound according to claim 2, wherein at least one of the methyl groups of said deuterated nifedipine is CD3.
4. The compound according to claim 1, wherein methyl groups are attached to positions 2 and 6 of the dihydropyridine ring, and at least one of them is substituted with CD3.
5. The compound according to claim 4, wherein said deuterated dihydropyridine is deuterated nifedipine having the formula
6. The compound according to claim 1, wherein said dihydropyridine is nifedipine, nicardipine, nimodipine, niludipine, nisoldipine, nitrendipine, felodipine, ifradipine or amlodipine.
36
7. A method for making a deuterated dihydropyridine wherein at least one of the H atoms is replaced with a deuterium atom, said method comprising: dissolving a dihydropyridine in a mixture of deuterochloroform and deuterium oxide to form a solution, adding trifluoroacetic anhydride and deuteroacetone to said solution, freezing and sealing said solution within a vessel, heating said solution at a temperature and for a period of time sufficient to deuterate all of the hydrogen atoms at the 2 and 6 position on said dihydropyridine, and recovering said deuterized dihydropyridine.
8. The method according to claim 7, wherein said deuterized dihydropyridine is deuterated nifedipine and said method comprises: dissolving nifedipine in a mixture of deuterochloroform and deuterium oxide to form a solution, adding trifluoroacetic anhydride and deuteroacetone to said solution, freezing and sealing said solution within a vessel, heating said solution at a temperature and for a period of time sufficient to deuterate all of the hydrogen atoms on the methyl groups at the 2 and 6 position on said nifedipine, and recovering said deuterized nifedipine.
9. The method according to claim 8, said method comprising: dissolving 80 mg of nifedipine in a mixture of about 2 ml of deuterochloroform and about 0.5 ml of deuterium oxide to form a solution, adding about 0.2 ml of trifluoroacetic anhydride and 2 ml of deuteroacetone to said solution and mixing therewith, freezing and sealing said solution within a vessel, heating said solution at a temperature of about 50° to about 65 °C for a period of time of about 150 to 180 hours, cooling said heated solution and recovering said deuterated nifedipine.
10. The method as defined in claim 9 wherein said temperature is about 55° to about 60°C.
11. The method as defined in claim 9 wherein said period of time is from about 160 to 170 hours.
37
12. The method as defined in claim 9 wherein said temperature is about 57 °C and said period of time is about 168 hours.
13. A method for the treatment of hypertension in an animal suffering therefrom comprising administering to said animal a therapeutically effective amount of a deuterated nifedipine wherein at least one of the H atoms is replaced with a deuterium atom.
14. A method as in claim 13 wherein methyl groups are attached to positions 2 and 6 of the dihydropyridine ring, and at least one of them is substituted with CD3.
15. A method of detecting whether a pharmaceutical compound is identical and/or bioequivalent to a known pharmaceutical compound comprising the steps of
(a) determining the molecular and isotopic structure of said known pharmaceutical compound by gas chromatography-isotope ratio mass spectrometry,
(b) determining the molecular and isotopic structure of said pharmaceutical compound subject to said detection by gas chromatography-isotope ratio mass spectrometry,
(c) comparing the results of said two determinations to detect any isotope variation in the molecular structure of said pharmaceutical compound over that of the known pharmaceutical compound.
16. The use of a deuterated nifedipine wherein at least one of the H atoms is replaced with a deuterium atom, as an antihypertensive drug.
17. A use as in claim 16 wherein methyl groups are attached to positions 2 and 6 of the dihydropyridine ring, and at least one of them is substituted with CD3.
18. The use of a deuterated nifedipine wherein at least one of the H atoms is replaced with a deuterium atom, for preparing an antihypertensive medicament.
19. The use as in claim 18 wherein methyl groups are attached to positions 2 and 6 of the dihydropyridine ring, and at least one of them is substituted with CD3.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BR9507200A BR9507200A (en) | 1994-03-25 | 1995-03-27 | Improved drug efficacy by deuteration |
| DE69535592T DE69535592T2 (en) | 1994-03-25 | 1995-03-27 | IMPROVING THE EFFECTIVENESS OF MEDICINES BY DEUTERIZATION |
| KR1019960705390A KR100477070B1 (en) | 1994-03-25 | 1995-03-27 | Enhancing the efficacy of pharmaceuticals by deuteration |
| EP95912109A EP0751926B1 (en) | 1994-03-25 | 1995-03-27 | Enhancement of the efficacy of drugs by deuteration |
| AU19441/95A AU707748B2 (en) | 1994-03-25 | 1995-03-27 | Enhancement of the efficacy of drugs by deuteration |
| KR10-2004-7010591A KR20040068613A (en) | 1994-03-25 | 1995-03-27 | Deuterated compound and composition for treating hypertension |
| JP52488595A JP3696884B2 (en) | 1994-03-25 | 1995-03-27 | Enhancement of drug efficacy by deuteration |
| MXPA/A/1996/004309A MXPA96004309A (en) | 1994-03-25 | 1996-09-25 | Increased drug effectiveness by deuterac |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21789794A | 1994-03-25 | 1994-03-25 | |
| US08/217,897 | 1994-03-25 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| WO1995026325A2 WO1995026325A2 (en) | 1995-10-05 |
| WO1995026325A3 WO1995026325A3 (en) | 1995-12-14 |
| WO1995026325B1 true WO1995026325B1 (en) | 1996-02-01 |
Family
ID=22812932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CA1995/000154 WO1995026325A2 (en) | 1994-03-25 | 1995-03-27 | Enhancement of the efficacy of drugs by deuteration |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5846514A (en) |
| EP (1) | EP0751926B1 (en) |
| JP (1) | JP3696884B2 (en) |
| KR (2) | KR20040068613A (en) |
| CN (1) | CN1087725C (en) |
| AT (1) | ATE372966T1 (en) |
| AU (1) | AU707748B2 (en) |
| BR (1) | BR9507200A (en) |
| CA (1) | CA2186371A1 (en) |
| DE (1) | DE69535592T2 (en) |
| ES (1) | ES2293638T3 (en) |
| WO (1) | WO1995026325A2 (en) |
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- 1995-03-27 KR KR10-2004-7010591A patent/KR20040068613A/en not_active Application Discontinuation
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- 1995-03-27 BR BR9507200A patent/BR9507200A/en not_active Application Discontinuation
- 1995-03-27 DE DE69535592T patent/DE69535592T2/en not_active Expired - Lifetime
- 1995-03-27 AU AU19441/95A patent/AU707748B2/en not_active Ceased
- 1995-03-27 CN CN95193186A patent/CN1087725C/en not_active Expired - Fee Related
- 1995-03-27 KR KR1019960705390A patent/KR100477070B1/en not_active IP Right Cessation
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- 1995-03-27 WO PCT/CA1995/000154 patent/WO1995026325A2/en active IP Right Grant
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- 1995-03-27 JP JP52488595A patent/JP3696884B2/en not_active Expired - Fee Related
- 1995-03-27 EP EP95912109A patent/EP0751926B1/en not_active Expired - Lifetime
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1996
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