DE2139398C3 - Difluormethyllv2^33-pentafluorpropyläther, Verfahren zu seiner Herstellung und diesen enthaltendes Anaesthetikum - Google Patents
Difluormethyllv2^33-pentafluorpropyläther, Verfahren zu seiner Herstellung und diesen enthaltendes AnaesthetikumInfo
- Publication number
- DE2139398C3 DE2139398C3 DE2139398A DE2139398A DE2139398C3 DE 2139398 C3 DE2139398 C3 DE 2139398C3 DE 2139398 A DE2139398 A DE 2139398A DE 2139398 A DE2139398 A DE 2139398A DE 2139398 C3 DE2139398 C3 DE 2139398C3
- Authority
- DE
- Germany
- Prior art keywords
- chf
- ether
- difluoromethyl
- compound
- anesthetic
- 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
Links
- 230000003444 anaesthetic effect Effects 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- FQFKTKUFHWNTBN-UHFFFAOYSA-N trifluoro-$l^{3}-bromane Chemical compound FBr(F)F FQFKTKUFHWNTBN-UHFFFAOYSA-N 0.000 claims description 7
- 241000699670 Mus sp. Species 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- PCTQNZRJAGLDPD-UHFFFAOYSA-N 3-(difluoromethoxy)-1,1,2,2-tetrafluoropropane Chemical compound FC(F)OCC(F)(F)C(F)F PCTQNZRJAGLDPD-UHFFFAOYSA-N 0.000 claims description 3
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 3
- VGZTVHRJEVWFIA-UHFFFAOYSA-N synthane Chemical compound FC(F)OC(F)C(F)(F)C(F)F VGZTVHRJEVWFIA-UHFFFAOYSA-N 0.000 claims description 3
- GGCYTJDMGHFLIX-UHFFFAOYSA-N 1-chloro-1-(difluoromethoxy)-2,2,3,3-tetrafluoropropane Chemical compound FC(F)OC(C(C(F)F)(F)F)Cl GGCYTJDMGHFLIX-UHFFFAOYSA-N 0.000 claims description 2
- NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003179 convulsant agent Substances 0.000 claims 3
- 241001465754 Metazoa Species 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 239000003193 general anesthetic agent Substances 0.000 claims 1
- 231100000518 lethal Toxicity 0.000 claims 1
- 230000001665 lethal effect Effects 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 125000001153 fluoro group Chemical group F* 0.000 description 10
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 8
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 8
- 238000001030 gas--liquid chromatography Methods 0.000 description 8
- 206010002091 Anaesthesia Diseases 0.000 description 7
- 230000037005 anaesthesia Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 4
- IOCGMLSHRBHNCM-UHFFFAOYSA-N difluoromethoxy(difluoro)methane Chemical compound FC(F)OC(F)F IOCGMLSHRBHNCM-UHFFFAOYSA-N 0.000 description 4
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 4
- 238000004508 fractional distillation Methods 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229910014263 BrF3 Inorganic materials 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
- -1 lithium aluminum hydride Chemical compound 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000029058 respiratory gaseous exchange Effects 0.000 description 2
- HUAUNKAZQWMVFY-UHFFFAOYSA-M sodium;oxocalcium;hydroxide Chemical compound [OH-].[Na+].[Ca]=O HUAUNKAZQWMVFY-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PTFZMXAQQHCHMG-RJYAGPCLSA-N (2S)-2-amino-N-(1-diphenoxyphosphorylethyl)-3-methylpentanamide Chemical compound C=1C=CC=CC=1OP(=O)(C(C)NC(=O)[C@@H](N)C(C)CC)OC1=CC=CC=C1 PTFZMXAQQHCHMG-RJYAGPCLSA-N 0.000 description 1
- TXOZSRCVHASUCW-UHFFFAOYSA-N 1,3,3,3-tetrafluoropropan-1-ol Chemical compound OC(F)CC(F)(F)F TXOZSRCVHASUCW-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
- C07C43/123—Saturated ethers containing halogen both carbon chains are substituted by halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6267970A | 1970-08-10 | 1970-08-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2139398A1 DE2139398A1 (de) | 1972-02-17 |
| DE2139398B2 DE2139398B2 (de) | 1980-03-13 |
| DE2139398C3 true DE2139398C3 (de) | 1980-11-06 |
Family
ID=22044106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2139398A Expired DE2139398C3 (de) | 1970-08-10 | 1971-08-06 | Difluormethyllv2^33-pentafluorpropyläther, Verfahren zu seiner Herstellung und diesen enthaltendes Anaesthetikum |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3689459A (enExample) |
| JP (3) | JPS551248B1 (enExample) |
| AU (1) | AU449736B2 (enExample) |
| BE (1) | BE770840A (enExample) |
| CA (1) | CA951743A (enExample) |
| CH (1) | CH557790A (enExample) |
| DE (1) | DE2139398C3 (enExample) |
| DK (1) | DK130209B (enExample) |
| ES (1) | ES394041A1 (enExample) |
| FR (1) | FR2102150B1 (enExample) |
| GB (3) | GB1325275A (enExample) |
| IL (1) | IL37335A (enExample) |
| IT (1) | IT1053683B (enExample) |
| NL (1) | NL7110768A (enExample) |
| SE (2) | SE383733B (enExample) |
| ZA (1) | ZA714805B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3896177A (en) * | 1971-10-07 | 1975-07-22 | Airco Inc | 1-chloro-1-hydroperfluoropropyl difluoromethyl ether |
| US3943256A (en) * | 1973-06-25 | 1976-03-09 | Baxter Laboratories, Inc. | Antipsychotic agents |
| US3976788A (en) * | 1973-06-25 | 1976-08-24 | Baxter Laboratories, Inc. | Antipsychotic agents |
| CA1129892A (en) * | 1979-03-12 | 1982-08-17 | Ross C. Terrell | Process for adjusting the halogen content of halogenated aliphatic ethers |
| CA1130322A (en) * | 1979-04-25 | 1982-08-24 | Airco, Inc. | Method for the dehalogenation of ethers |
| GB8321569D0 (en) * | 1983-08-10 | 1983-09-14 | Ici Plc | Heat pumps |
| JPS6094671U (ja) * | 1983-12-05 | 1985-06-27 | コニカ株式会社 | 現像装置 |
| US5015781A (en) * | 1988-05-06 | 1991-05-14 | Boc, Inc. | Anesthetic compound and method of preparing |
| US4874901A (en) * | 1988-05-06 | 1989-10-17 | Boc, Inc. | Process for the production of polyfluorinated ethers |
| US6316017B1 (en) * | 1990-02-02 | 2001-11-13 | The United States Of America As Represented By The Secretary Of Agriculture | Composition and apparatus useful for attracting and controlling insect pests |
| US5185474A (en) * | 1990-10-02 | 1993-02-09 | W. R. Grace & Co.-Conn. | Synthesis of fluorinated dimethyl ethers |
| US5278342A (en) * | 1992-03-25 | 1994-01-11 | Hampshire Chemical Corp. | Vapor phase chlorination of difluoromethyl methyl ether |
| US5446211A (en) * | 1994-04-01 | 1995-08-29 | Hampshire Chemical Corp. | Chlorination of difluoromethyl methyl ether |
| US5543055A (en) * | 1995-06-06 | 1996-08-06 | Hampshire Chemical Corp. | Purifications of flourinated dimethyl ethers |
| KR20000018974A (ko) * | 1998-09-07 | 2000-04-06 | 김형모 | 내부버팀링지지 관로 보수공법 및 보수재 |
-
1970
- 1970-08-10 US US62679A patent/US3689459A/en not_active Expired - Lifetime
-
1971
- 1971-07-14 CA CA118,210,A patent/CA951743A/en not_active Expired
- 1971-07-19 IL IL37335A patent/IL37335A/xx unknown
- 1971-07-20 ZA ZA714805A patent/ZA714805B/xx unknown
- 1971-08-02 BE BE770840A patent/BE770840A/xx unknown
- 1971-08-04 JP JP5839871A patent/JPS551248B1/ja active Pending
- 1971-08-04 GB GB6016172A patent/GB1325275A/en not_active Expired
- 1971-08-04 GB GB3662471A patent/GB1325274A/en not_active Expired
- 1971-08-04 GB GB6016272A patent/GB1325276A/en not_active Expired
- 1971-08-04 NL NL7110768A patent/NL7110768A/xx not_active Application Discontinuation
- 1971-08-06 AU AU32067/71A patent/AU449736B2/en not_active Expired
- 1971-08-06 DE DE2139398A patent/DE2139398C3/de not_active Expired
- 1971-08-09 ES ES394041A patent/ES394041A1/es not_active Expired
- 1971-08-09 FR FR7129037A patent/FR2102150B1/fr not_active Expired
- 1971-08-10 DK DK388571AA patent/DK130209B/da not_active IP Right Cessation
- 1971-08-10 SE SE7110210A patent/SE383733B/xx unknown
- 1971-08-10 IT IT27388/71A patent/IT1053683B/it active
- 1971-08-10 CH CH1173571A patent/CH557790A/xx not_active IP Right Cessation
- 1971-11-09 JP JP8877871A patent/JPS551249B1/ja active Pending
- 1971-11-09 JP JP8877971A patent/JPS551250B1/ja active Pending
-
1974
- 1974-09-12 SE SE7411522A patent/SE396592B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1325276A (en) | 1973-08-01 |
| NL7110768A (enExample) | 1972-02-14 |
| GB1325275A (en) | 1973-08-01 |
| ZA714805B (en) | 1972-04-26 |
| SE7411522L (enExample) | 1974-09-12 |
| CH557790A (de) | 1975-01-15 |
| FR2102150A1 (enExample) | 1972-04-07 |
| US3689459A (en) | 1972-09-05 |
| JPS551250B1 (enExample) | 1980-01-12 |
| JPS551248B1 (enExample) | 1980-01-12 |
| JPS551249B1 (enExample) | 1980-01-12 |
| FR2102150B1 (enExample) | 1974-09-06 |
| DK130209B (da) | 1975-01-20 |
| GB1325274A (en) | 1973-08-01 |
| BE770840A (fr) | 1971-12-16 |
| CA951743A (en) | 1974-07-23 |
| DK130209C (enExample) | 1975-08-11 |
| DE2139398A1 (de) | 1972-02-17 |
| AU449736B2 (en) | 1974-06-20 |
| ES394041A1 (es) | 1973-12-16 |
| IT1053683B (it) | 1981-10-10 |
| IL37335A (en) | 1973-11-28 |
| IL37335A0 (en) | 1971-10-20 |
| SE396592B (sv) | 1977-09-26 |
| SE383733B (sv) | 1976-03-29 |
| AU3206771A (en) | 1973-02-08 |
| DE2139398B2 (de) | 1980-03-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |