DE1470258C - - Google Patents
Info
- Publication number
- DE1470258C DE1470258C DE1470258C DE 1470258 C DE1470258 C DE 1470258C DE 1470258 C DE1470258 C DE 1470258C
- Authority
- DE
- Germany
- Prior art keywords
- hydrochloride
- isoxazole
- phenyl
- phenylisoxazole
- general formula
- 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.)
- Active
Links
- -1 haloalkyl compound Chemical class 0.000 claims description 17
- 150000002545 isoxazoles Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000011780 sodium chloride Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- IYABWNGZIDDRAK-UHFFFAOYSA-N Propadiene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
- 239000012530 fluid Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-K 2qpq Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 7
- KKUDUDGVXMDUAH-UHFFFAOYSA-N 5-phenyl-1,2-oxazole;hydrochloride Chemical compound Cl.O1N=CC=C1C1=CC=CC=C1 KKUDUDGVXMDUAH-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000000202 analgesic Effects 0.000 description 4
- 230000003110 anti-inflammatory Effects 0.000 description 4
- 230000001754 anti-pyretic Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 206010011224 Cough Diseases 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 210000001772 Blood Platelets Anatomy 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N Isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
- WTGOJGJYRSBYQN-UHFFFAOYSA-N N,N-dimethyl-1-(3-phenyl-1,2-oxazol-5-yl)methanamine Chemical compound O1C(CN(C)C)=CC(C=2C=CC=CC=2)=N1 WTGOJGJYRSBYQN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- IDCHQQSVJAAUQQ-UHFFFAOYSA-N Oxolamine Chemical compound O1C(CCN(CC)CC)=NC(C=2C=CC=CC=2)=N1 IDCHQQSVJAAUQQ-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 230000000954 anitussive Effects 0.000 description 2
- 239000002221 antipyretic Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000005712 crystallization Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 229960003625 oxolamine Drugs 0.000 description 2
- 239000001184 potassium carbonate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-Methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- HAARZQOXENAXOY-UHFFFAOYSA-N 3-phenyl-5-(2-piperidin-1-ylethyl)-1,2-oxazole Chemical compound C1CCCCN1CCC(ON=1)=CC=1C1=CC=CC=C1 HAARZQOXENAXOY-UHFFFAOYSA-N 0.000 description 1
- IVDLMJVLIPZPJC-UHFFFAOYSA-N 3-phenyl-5-(2-pyrrolidin-1-ylethyl)-1,2-oxazole Chemical compound C1CCCN1CCC(ON=1)=CC=1C1=CC=CC=C1 IVDLMJVLIPZPJC-UHFFFAOYSA-N 0.000 description 1
- IDNKMEIJFTWUEG-UHFFFAOYSA-N 3-phenyl-5-(piperidin-1-ylmethyl)-1,2-oxazole Chemical compound C=1C(C=2C=CC=CC=2)=NOC=1CN1CCCCC1 IDNKMEIJFTWUEG-UHFFFAOYSA-N 0.000 description 1
- IEFFAOXMKNLERG-UHFFFAOYSA-N 3-phenyl-5-(pyrrolidin-1-ylmethyl)-1,2-oxazole Chemical compound C=1C(C=2C=CC=CC=2)=NOC=1CN1CCCC1 IEFFAOXMKNLERG-UHFFFAOYSA-N 0.000 description 1
- AYTLPTRYSGTHNV-UHFFFAOYSA-N 3-propyl-1,2-oxazole Chemical compound CCCC=1C=CON=1 AYTLPTRYSGTHNV-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 description 1
- WFNHAQXQKOMQJD-UHFFFAOYSA-N 5-(2-piperidin-1-ylethyl)-3-pyridin-2-yl-1,2-oxazole Chemical compound C1CCCCN1CCC(ON=1)=CC=1C1=CC=CC=N1 WFNHAQXQKOMQJD-UHFFFAOYSA-N 0.000 description 1
- WKLODVHSLLFKMY-UHFFFAOYSA-N 5-(chloromethyl)-3-phenyl-1,2-oxazole Chemical compound O1C(CCl)=CC(C=2C=CC=CC=2)=N1 WKLODVHSLLFKMY-UHFFFAOYSA-N 0.000 description 1
- BXQDLEHCXQQSCH-UHFFFAOYSA-N 5-phenyl-1,2-oxazole Chemical compound O1N=CC=C1C1=CC=CC=C1 BXQDLEHCXQQSCH-UHFFFAOYSA-N 0.000 description 1
- FMKRVPJPFOGYQU-UHFFFAOYSA-N 5-phenyl-3-(2-piperidin-1-ylethyl)-1,2-oxazole Chemical compound C1CCCCN1CCC(=NO1)C=C1C1=CC=CC=C1 FMKRVPJPFOGYQU-UHFFFAOYSA-N 0.000 description 1
- 229960003563 Calcium Carbonate Drugs 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- NSVPXSQGKZPPQO-UHFFFAOYSA-N Cl.NCCC1=NOC(=C1)C1=CC=CC=C1 Chemical compound Cl.NCCC1=NOC(=C1)C1=CC=CC=C1 NSVPXSQGKZPPQO-UHFFFAOYSA-N 0.000 description 1
- FXBAOPOSLKKSMZ-UHFFFAOYSA-N ClCCC1=NOC(=C1)C1=CC=CC=C1 Chemical compound ClCCC1=NOC(=C1)C1=CC=CC=C1 FXBAOPOSLKKSMZ-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N Diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001072332 Monia Species 0.000 description 1
- TZURGBMKPQSCEX-UHFFFAOYSA-N N,N-diethyl-2-(1,2-oxazol-3-yl)ethanamine Chemical compound CCN(CC)CCC=1C=CON=1 TZURGBMKPQSCEX-UHFFFAOYSA-N 0.000 description 1
- DQMAMIHHNSPITN-UHFFFAOYSA-N N,N-diethyl-2-(3-pyridin-2-yl-1,2-oxazol-5-yl)ethanamine Chemical compound O1C(CCN(CC)CC)=CC(C=2N=CC=CC=2)=N1 DQMAMIHHNSPITN-UHFFFAOYSA-N 0.000 description 1
- CRRDAMTVJKZOCP-UHFFFAOYSA-N N,N-dimethyl-1-(3-phenyl-1,2-oxazol-5-yl)ethanamine Chemical compound O1C(C(N(C)C)C)=CC(C=2C=CC=CC=2)=N1 CRRDAMTVJKZOCP-UHFFFAOYSA-N 0.000 description 1
- UWMXSCVXWHUWDH-UHFFFAOYSA-N N,N-dimethyl-1-(5-phenyl-1,2-oxazol-3-yl)methanamine Chemical compound O1N=C(CN(C)C)C=C1C1=CC=CC=C1 UWMXSCVXWHUWDH-UHFFFAOYSA-N 0.000 description 1
- IWFDFAVUKYJQTM-UHFFFAOYSA-N O1CCN(CC1)CCC1=NOC(=C1)C1=CC=CC=C1 Chemical compound O1CCN(CC1)CCC1=NOC(=C1)C1=CC=CC=C1 IWFDFAVUKYJQTM-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M Potassium bicarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000003000 nontoxic Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-L oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229940094025 potassium bicarbonate Drugs 0.000 description 1
- 230000003389 potentiating Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Family
ID=
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