CA1058224A - Halogenated methylcyclopropyl ethers - Google Patents
Halogenated methylcyclopropyl ethersInfo
- Publication number
- CA1058224A CA1058224A CA220,577A CA220577A CA1058224A CA 1058224 A CA1058224 A CA 1058224A CA 220577 A CA220577 A CA 220577A CA 1058224 A CA1058224 A CA 1058224A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- methoxy
- process according
- trifluoro
- trihalomethane
- 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
- ZUVAACFIEPYYOP-UHFFFAOYSA-N methoxycyclopropane Chemical class COC1CC1 ZUVAACFIEPYYOP-UHFFFAOYSA-N 0.000 title claims abstract description 5
- JMBNAADSRZEXLG-UHFFFAOYSA-N 1,2-dichloro-1,2,3-trifluoro-3-methoxycyclopropane Chemical compound COC1(F)C(F)(Cl)C1(F)Cl JMBNAADSRZEXLG-UHFFFAOYSA-N 0.000 claims abstract description 7
- LZKANMYVPJZLEW-UHFFFAOYSA-N aliflurane Chemical compound COC1(F)C(F)(F)C1(F)Cl LZKANMYVPJZLEW-UHFFFAOYSA-N 0.000 claims abstract description 6
- VECRNUHCKZZHBB-UHFFFAOYSA-N 1,1-dichloro-2,2,3-trifluoro-3-methoxycyclopropane Chemical compound COC1(F)C(F)(F)C1(Cl)Cl VECRNUHCKZZHBB-UHFFFAOYSA-N 0.000 claims abstract description 5
- WBDZKEYNLZEPKR-UHFFFAOYSA-N 1-bromo-1,2,2,3-tetrafluoro-3-methoxycyclopropane Chemical compound COC1(F)C(F)(F)C1(F)Br WBDZKEYNLZEPKR-UHFFFAOYSA-N 0.000 claims abstract 4
- 238000000034 method Methods 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 18
- -1 difluorocarbene Chemical class 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 3
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 claims description 3
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 claims description 3
- 229940099364 dichlorofluoromethane Drugs 0.000 claims description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- PFBUKDPBVNJDEW-UHFFFAOYSA-N dichlorocarbene Chemical class Cl[C]Cl PFBUKDPBVNJDEW-UHFFFAOYSA-N 0.000 claims description 2
- LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 claims description 2
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical group FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 5
- ZUNSDEVCBWMHMO-UHFFFAOYSA-N 1,1,2-trifluoro-2-methoxyethene Chemical compound COC(F)=C(F)F ZUNSDEVCBWMHMO-UHFFFAOYSA-N 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 229960001701 chloroform Drugs 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000003983 inhalation anesthetic agent Substances 0.000 abstract description 5
- 230000003444 anaesthetic effect Effects 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 239000003193 general anesthetic agent Substances 0.000 description 5
- BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 description 5
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 206010002091 Anaesthesia Diseases 0.000 description 4
- 230000037005 anaesthesia Effects 0.000 description 4
- 229940035674 anesthetics Drugs 0.000 description 4
- 229960003132 halothane Drugs 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- RFKMCNOHBTXSMU-UHFFFAOYSA-N methoxyflurane Chemical compound COC(F)(F)C(Cl)Cl RFKMCNOHBTXSMU-UHFFFAOYSA-N 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 150000001942 cyclopropanes Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229940005494 general anesthetics Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 229960002455 methoxyflurane Drugs 0.000 description 1
- VNXBKJFUJUWOCW-UHFFFAOYSA-N methylcyclopropane Chemical class CC1CC1 VNXBKJFUJUWOCW-UHFFFAOYSA-N 0.000 description 1
- XSGHLZBESSREDT-UHFFFAOYSA-N methylenecyclopropane Chemical class C=C1CC1 XSGHLZBESSREDT-UHFFFAOYSA-N 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000008560 physiological behavior Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000000063 preceeding effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000028527 righting reflex Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US451677A US3906111A (en) | 1974-03-15 | 1974-03-15 | Halogenated methylcyclopropyl ethers for inducing a state of anesthesia |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1058224A true CA1058224A (en) | 1979-07-10 |
Family
ID=23793246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA220,577A Expired CA1058224A (en) | 1974-03-15 | 1975-03-14 | Halogenated methylcyclopropyl ethers |
Country Status (9)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3995062A (en) * | 1974-12-26 | 1976-11-30 | W. R. Grace & Co. | Halocyclopropyl halomethyl ethers |
| US4570018A (en) * | 1983-05-31 | 1986-02-11 | Shionogi & Co., Ltd. | Fluorocyclopropanes |
| JP5504898B2 (ja) * | 2010-01-08 | 2014-05-28 | セントラル硝子株式会社 | ジフルオロシクロプロパン化合物の製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3557294A (en) * | 1967-10-12 | 1971-01-19 | Allied Chem | Fluorinated ethers as inhalation convulsants |
-
1974
- 1974-03-15 US US451677A patent/US3906111A/en not_active Expired - Lifetime
-
1975
- 1975-03-08 DE DE19752510157 patent/DE2510157A1/de active Pending
- 1975-03-13 DE DE19752510869 patent/DE2510869A1/de not_active Withdrawn
- 1975-03-14 GB GB10860/75A patent/GB1484421A/en not_active Expired
- 1975-03-14 CH CH327175A patent/CH615657A5/de not_active IP Right Cessation
- 1975-03-14 FR FR7508125A patent/FR2263755B1/fr not_active Expired
- 1975-03-14 JP JP50030283A patent/JPS50126642A/ja active Pending
- 1975-03-14 CA CA220,577A patent/CA1058224A/en not_active Expired
- 1975-03-14 ZA ZA00751612A patent/ZA751612B/xx unknown
- 1975-03-17 PH PH16922A patent/PH10783A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU7911375A (en) | 1976-09-16 |
| US3906111A (en) | 1975-09-16 |
| FR2263755A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-10-10 |
| JPS50126642A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-10-04 |
| GB1484421A (en) | 1977-09-01 |
| CH615657A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-02-15 |
| FR2263755B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-02-22 |
| DE2510157A1 (de) | 1975-09-18 |
| ZA751612B (en) | 1976-02-25 |
| PH10783A (en) | 1977-09-06 |
| DE2510869A1 (de) | 1975-09-18 |
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