DE2045050A1 - 5-(2-amino-alkoxy-phenoxy-methyl)-3-alkyl-isoxazoles - useful as hypotensives and sedatives - Google Patents
5-(2-amino-alkoxy-phenoxy-methyl)-3-alkyl-isoxazoles - useful as hypotensives and sedativesInfo
- Publication number
- DE2045050A1 DE2045050A1 DE19702045050 DE2045050A DE2045050A1 DE 2045050 A1 DE2045050 A1 DE 2045050A1 DE 19702045050 DE19702045050 DE 19702045050 DE 2045050 A DE2045050 A DE 2045050A DE 2045050 A1 DE2045050 A1 DE 2045050A1
- Authority
- DE
- Germany
- Prior art keywords
- methylisoxazole
- general formula
- acid addition
- methyl
- ethoxyphenoxymethyl
- 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.)
- Pending
Links
- 208000001953 Hypotension Diseases 0.000 title 1
- 208000021822 hypotensive Diseases 0.000 title 1
- 230000001077 hypotensive effect Effects 0.000 title 1
- 229940125723 sedative agent Drugs 0.000 title 1
- 239000000932 sedative agent Substances 0.000 title 1
- -1 R2 = H Chemical group 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- CUMCMYMKECWGHO-UHFFFAOYSA-N 3-methyl-1,2-oxazole Chemical compound CC=1C=CON=1 CUMCMYMKECWGHO-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- VREKKXKBOVVTRA-UHFFFAOYSA-N CCC(C)NCCOC(C1=CC(C)=NO1)OC1=CC=CC=C1 Chemical compound CCC(C)NCCOC(C1=CC(C)=NO1)OC1=CC=CC=C1 VREKKXKBOVVTRA-UHFFFAOYSA-N 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000000375 suspending agent Substances 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 114
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 49
- 238000002844 melting Methods 0.000 description 36
- 230000008018 melting Effects 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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- 239000000203 mixture Substances 0.000 description 9
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
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- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 7
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
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- 238000009835 boiling Methods 0.000 description 4
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- 235000019359 magnesium stearate Nutrition 0.000 description 4
- YUKUDJRCHPSDGC-UHFFFAOYSA-N 1,2-oxazole;hydrochloride Chemical compound Cl.C=1C=NOC=1 YUKUDJRCHPSDGC-UHFFFAOYSA-N 0.000 description 3
- DMUJLHLWCUMHRT-UHFFFAOYSA-N 5-(bromomethyl)-3-methyl-1,2-oxazole Chemical compound CC=1C=C(CBr)ON=1 DMUJLHLWCUMHRT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 230000003276 anti-hypertensive effect Effects 0.000 description 3
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- 239000000047 product Substances 0.000 description 3
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 2
- WMLBUOOGTKXAGU-UHFFFAOYSA-N 2-[(3-ethyl-1,2-oxazol-5-yl)methoxy]phenol Chemical compound C(C)C1=NOC(=C1)COC1=C(C=CC=C1)O WMLBUOOGTKXAGU-UHFFFAOYSA-N 0.000 description 2
- ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 description 2
- YCZVNYPFSNGXGJ-UHFFFAOYSA-N 5-(bromomethyl)-3-ethyl-1,2-oxazole Chemical compound CCC=1C=C(CBr)ON=1 YCZVNYPFSNGXGJ-UHFFFAOYSA-N 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
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- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702045050 DE2045050A1 (en) | 1970-09-11 | 1970-09-11 | 5-(2-amino-alkoxy-phenoxy-methyl)-3-alkyl-isoxazoles - useful as hypotensives and sedatives |
| SE11463/71A SE366993B (enrdf_load_stackoverflow) | 1970-09-11 | 1971-09-09 | |
| AU33308/71A AU3330871A (enrdf_load_stackoverflow) | 1970-09-11 | 1971-09-09 | |
| DK443671AA DK129164B (da) | 1970-09-11 | 1971-09-09 | Analogifremgangsmåde til fremstilling af 3-alkyl-5-aryloxymethylisoxazoler eller syreadditionssalte deraf. |
| CH199275A CH563377A5 (enrdf_load_stackoverflow) | 1970-09-11 | 1971-09-09 | |
| CH1324771A CH562230A5 (enrdf_load_stackoverflow) | 1970-09-11 | 1971-09-09 | |
| ES394971A ES394971A1 (es) | 1970-09-11 | 1971-09-10 | Un procedimiento para la preparacion de nuevos 3-alcohil-5 -ariloximetilisoxazoles. |
| US00179522A US3838162A (en) | 1970-09-11 | 1971-09-10 | 3-lower alkyl-5-(o-(omega-amino-alkoxy)-phenoxymethyl)-isoxazoles and salts thereof |
| ES394967A ES394967A1 (es) | 1970-09-11 | 1971-09-10 | Procedimiento para la preparacion de 3-alcohil-5-ariloxime-tilisoxazoles. |
| GB4240371A GB1345214A (en) | 1970-09-11 | 1971-09-10 | Isoxazoles |
| BE772490A BE772490A (fr) | 1970-09-11 | 1971-09-10 | Nouveaux 3-alcoyl-5-aryloxymethyl-isoxazols et procedes pour les fabriquer |
| ES394968A ES394968A1 (es) | 1970-09-11 | 1971-09-10 | Un procedimiento para la preparacion de nuevos 3-alcohil-5-ariloximetilisoxazoles. |
| FR7132790A FR2106456B1 (enrdf_load_stackoverflow) | 1970-09-11 | 1971-09-10 | |
| NL7112465A NL7112465A (enrdf_load_stackoverflow) | 1970-09-11 | 1971-09-10 | |
| AT790271A AT309422B (de) | 1970-09-11 | 1971-09-10 | Verfahren zur Herstellung neuer 3-Alkyl-5-aryloxymethylisoxazole und ihrer Salze |
| AT830672A AT309423B (de) | 1970-09-11 | 1971-09-10 | Verfahren zur Herstellung neuer 3-Alkyl-5-aryloxymethyl-isoxazole und ihrer Salze |
| ES394970A ES394970A1 (es) | 1970-09-11 | 1971-09-10 | Un procedimiento para la preparacion de nuevos 3-alcohil-5-ariloximetilisoxazoles. |
| ES394972A ES394972A1 (es) | 1970-09-11 | 1971-09-10 | Procedimiento para la preparacion de nuevos 3 - alcohil - ariloximetilisoxazoles. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702045050 DE2045050A1 (en) | 1970-09-11 | 1970-09-11 | 5-(2-amino-alkoxy-phenoxy-methyl)-3-alkyl-isoxazoles - useful as hypotensives and sedatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2045050A1 true DE2045050A1 (en) | 1972-03-23 |
Family
ID=5782214
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702045050 Pending DE2045050A1 (en) | 1970-09-11 | 1970-09-11 | 5-(2-amino-alkoxy-phenoxy-methyl)-3-alkyl-isoxazoles - useful as hypotensives and sedatives |
Country Status (5)
| Country | Link |
|---|---|
| AT (2) | AT309423B (enrdf_load_stackoverflow) |
| AU (1) | AU3330871A (enrdf_load_stackoverflow) |
| CH (2) | CH563377A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2045050A1 (enrdf_load_stackoverflow) |
| ES (1) | ES394968A1 (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994022842A1 (en) | 1993-03-29 | 1994-10-13 | Basf Aktiengesellschaft | 1-amino-3-phenoxy propane derivatives as modulators of multi-drug resistance |
| WO2012152741A1 (de) | 2011-05-10 | 2012-11-15 | Bayer Intellectual Property Gmbh | Bicyclische (thio)carbonylamidine |
-
1970
- 1970-09-11 DE DE19702045050 patent/DE2045050A1/de active Pending
-
1971
- 1971-09-09 CH CH199275A patent/CH563377A5/xx not_active IP Right Cessation
- 1971-09-09 CH CH1324771A patent/CH562230A5/xx not_active IP Right Cessation
- 1971-09-09 AU AU33308/71A patent/AU3330871A/en not_active Expired
- 1971-09-10 AT AT830672A patent/AT309423B/de not_active IP Right Cessation
- 1971-09-10 AT AT790271A patent/AT309422B/de not_active IP Right Cessation
- 1971-09-10 ES ES394968A patent/ES394968A1/es not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994022842A1 (en) | 1993-03-29 | 1994-10-13 | Basf Aktiengesellschaft | 1-amino-3-phenoxy propane derivatives as modulators of multi-drug resistance |
| WO2012152741A1 (de) | 2011-05-10 | 2012-11-15 | Bayer Intellectual Property Gmbh | Bicyclische (thio)carbonylamidine |
Also Published As
| Publication number | Publication date |
|---|---|
| AU3330871A (enrdf_load_stackoverflow) | 1973-03-15 |
| CH563377A5 (enrdf_load_stackoverflow) | 1975-06-30 |
| ES394968A1 (es) | 1974-12-01 |
| AT309422B (de) | 1973-08-27 |
| AT309423B (de) | 1973-08-27 |
| CH562230A5 (enrdf_load_stackoverflow) | 1975-05-30 |
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