CA2352597C - Compositions de fluoroether et procedes d'inhibition de leur degradation en presence d'un acide de lewis - Google Patents
Compositions de fluoroether et procedes d'inhibition de leur degradation en presence d'un acide de lewis Download PDFInfo
- Publication number
- CA2352597C CA2352597C CA002352597A CA2352597A CA2352597C CA 2352597 C CA2352597 C CA 2352597C CA 002352597 A CA002352597 A CA 002352597A CA 2352597 A CA2352597 A CA 2352597A CA 2352597 C CA2352597 C CA 2352597C
- Authority
- CA
- Canada
- Prior art keywords
- sevoflurane
- lewis acid
- water
- degradation
- container
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000002841 Lewis acid Substances 0.000 title claims abstract description 77
- 150000007517 lewis acids Chemical class 0.000 title claims abstract description 77
- 238000006731 degradation reaction Methods 0.000 title claims abstract description 43
- 230000015556 catabolic process Effects 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims description 22
- 229920001774 Perfluoroether Polymers 0.000 title description 53
- 239000000203 mixture Substances 0.000 title description 29
- 230000002401 inhibitory effect Effects 0.000 title description 4
- DFEYYRMXOJXZRJ-UHFFFAOYSA-N sevoflurane Chemical compound FCOC(C(F)(F)F)C(F)(F)F DFEYYRMXOJXZRJ-UHFFFAOYSA-N 0.000 claims abstract description 88
- 229960002078 sevoflurane Drugs 0.000 claims abstract description 87
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 68
- 239000003112 inhibitor Substances 0.000 claims abstract description 48
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims abstract description 12
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims abstract description 12
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000005844 Thymol Substances 0.000 claims abstract description 5
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims abstract description 5
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 claims abstract description 5
- 229960002216 methylparaben Drugs 0.000 claims abstract description 5
- OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 claims abstract description 5
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims abstract description 5
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 claims abstract description 5
- 229960003415 propylparaben Drugs 0.000 claims abstract description 5
- 229960000790 thymol Drugs 0.000 claims abstract description 5
- 239000004322 Butylated hydroxytoluene Substances 0.000 claims abstract description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims abstract description 4
- 229940095259 butylated hydroxytoluene Drugs 0.000 claims abstract description 4
- 229960004134 propofol Drugs 0.000 claims abstract description 4
- 239000003708 ampul Substances 0.000 claims description 27
- 239000011521 glass Substances 0.000 claims description 26
- 238000005406 washing Methods 0.000 claims description 4
- 238000007789 sealing Methods 0.000 claims description 3
- 229910000831 Steel Inorganic materials 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 239000010959 steel Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 34
- LFIIIPMEVREURN-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-[2-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)ethoxy]propane Chemical compound FC(F)(F)C(C(F)(F)F)OCCOC(C(F)(F)F)C(F)(F)F LFIIIPMEVREURN-UHFFFAOYSA-N 0.000 description 12
- 239000008380 degradant Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- 230000003444 anaesthetic effect Effects 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000007857 degradation product Substances 0.000 description 5
- 230000000087 stabilizing effect Effects 0.000 description 5
- SYYPKTWNTILAMR-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-(fluoromethoxymethoxy)propane Chemical compound FCOCOC(C(F)(F)F)C(F)(F)F SYYPKTWNTILAMR-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 description 4
- OHHWIUWMPLFBMA-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-(1,1,1,3,3,3-hexafluoropropan-2-yloxymethoxy)propane Chemical compound FC(F)(F)C(C(F)(F)F)OCOC(C(F)(F)F)C(F)(F)F OHHWIUWMPLFBMA-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 235000019256 formaldehyde Nutrition 0.000 description 3
- 239000003193 general anesthetic agent Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229960002725 isoflurane Drugs 0.000 description 3
- RFKMCNOHBTXSMU-UHFFFAOYSA-N methoxyflurane Chemical compound COC(F)(F)C(Cl)Cl RFKMCNOHBTXSMU-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- -1 amino, methoxy, difluoromethyl Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 231100000481 chemical toxicant Toxicity 0.000 description 2
- DPYMFVXJLLWWEU-UHFFFAOYSA-N desflurane Chemical compound FC(F)OC(F)C(F)(F)F DPYMFVXJLLWWEU-UHFFFAOYSA-N 0.000 description 2
- 229960003537 desflurane Drugs 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229960002455 methoxyflurane Drugs 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- QZFIQARJCSJGEG-UHFFFAOYSA-N 1,1,1,2-tetrafluoro-2-(1,2,2,2-tetrafluoroethoxy)ethane Chemical compound FC(F)(F)C(F)OC(F)C(F)(F)F QZFIQARJCSJGEG-UHFFFAOYSA-N 0.000 description 1
- PBLGJMMEOGUSID-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-(fluoromethyl)-2-[1,1,1,3,3,3-hexafluoro-2-(fluoromethyl)propan-2-yl]oxypropane Chemical compound FCC(C(F)(F)F)(C(F)(F)F)OC(CF)(C(F)(F)F)C(F)(F)F PBLGJMMEOGUSID-UHFFFAOYSA-N 0.000 description 1
- RNQKTBRQJCQNFK-UHFFFAOYSA-N CC(C)(C)C1(CC=C(C=C1C(C)(C)C)C)O.OCC1=CC=CC=C1 Chemical class CC(C)(C)C1(CC=C(C=C1C(C)(C)C)C)O.OCC1=CC=CC=C1 RNQKTBRQJCQNFK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910004014 SiF4 Inorganic materials 0.000 description 1
- 229910008284 Si—F Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
- 230000003413 degradative effect Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- JPGQOUSTVILISH-UHFFFAOYSA-N enflurane Chemical compound FC(F)OC(F)(F)C(F)Cl JPGQOUSTVILISH-UHFFFAOYSA-N 0.000 description 1
- 229960000305 enflurane Drugs 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000004890 malting Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- ABTOQLMXBSRXSM-UHFFFAOYSA-N silicon tetrafluoride Chemical compound F[Si](F)(F)F ABTOQLMXBSRXSM-UHFFFAOYSA-N 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000011124 type III (regular soda lime glass) Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002437603A CA2437603C (fr) | 1997-01-27 | 1998-01-23 | Compositions de fluoroether et procedes d'inhibition de leur degradation en presence d'un acide de lewis |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/789,679 | 1997-01-27 | ||
| US08/789,679 US5990176A (en) | 1997-01-27 | 1997-01-27 | Fluoroether compositions and methods for inhibiting their degradation in the presence of a Lewis acid |
| CA002278133A CA2278133C (fr) | 1997-01-27 | 1998-01-23 | Compositions de fluoroether et procedes d'inhibition de leur degradation en presence d'un acide de lewis |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002278133A Division CA2278133C (fr) | 1997-01-27 | 1998-01-23 | Compositions de fluoroether et procedes d'inhibition de leur degradation en presence d'un acide de lewis |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002437603A Division CA2437603C (fr) | 1997-01-27 | 1998-01-23 | Compositions de fluoroether et procedes d'inhibition de leur degradation en presence d'un acide de lewis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2352597A1 CA2352597A1 (fr) | 1998-07-30 |
| CA2352597C true CA2352597C (fr) | 2004-05-11 |
Family
ID=25681071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002352597A Expired - Lifetime CA2352597C (fr) | 1997-01-27 | 1998-01-23 | Compositions de fluoroether et procedes d'inhibition de leur degradation en presence d'un acide de lewis |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2352597C (fr) |
-
1998
- 1998-01-23 CA CA002352597A patent/CA2352597C/fr not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2352597A1 (fr) | 1998-07-30 |
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|---|---|---|
| CA2278133C (fr) | Compositions de fluoroether et procedes d'inhibition de leur degradation en presence d'un acide de lewis | |
| CA2352597C (fr) | Compositions de fluoroether et procedes d'inhibition de leur degradation en presence d'un acide de lewis | |
| US7816409B2 (en) | Stable pharmaceutical composition of fluoroether compound for anesthetic use method for stabilizing a fluoroether compound, use of stabilizer agent for precluding the degradation of a fluoroether compound | |
| CA2437603C (fr) | Compositions de fluoroether et procedes d'inhibition de leur degradation en presence d'un acide de lewis | |
| MXPA99006919A (en) | Fluoroether compositions and methods for inhibiting their degradation in the presence of a lewis acid | |
| HK1074434B (en) | Fluoroether compositions and methods for inhibiting their degradation in the presence of a lewis acid | |
| HK1108633B (en) | Stable pharmaceutical composition of fluoroether compound for anesthetic use, method for stabilizing a fluoroether compound, use of stabilizer agent for precluding the degradation of a fluoroether compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20180123 |