NO751753L - - Google Patents
Info
- Publication number
- NO751753L NO751753L NO751753A NO751753A NO751753L NO 751753 L NO751753 L NO 751753L NO 751753 A NO751753 A NO 751753A NO 751753 A NO751753 A NO 751753A NO 751753 L NO751753 L NO 751753L
- Authority
- NO
- Norway
- Prior art keywords
- methylstyrene
- propanol
- butylphenyl
- analysis
- found
- Prior art date
Links
- -1 aralkyl hydrocarbons Chemical class 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 3
- 229960004592 isopropanol Drugs 0.000 claims 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- UXMYYKOIANVGEH-UHFFFAOYSA-N 1-butan-2-yl-4-prop-1-en-2-ylbenzene Chemical compound CCC(C)C1=CC=C(C(C)=C)C=C1 UXMYYKOIANVGEH-UHFFFAOYSA-N 0.000 description 2
- NZGHJIGCMVGJTF-UHFFFAOYSA-N 1-cyclohexyl-4-prop-1-en-2-ylbenzene Chemical compound C1=CC(C(=C)C)=CC=C1C1CCCCC1 NZGHJIGCMVGJTF-UHFFFAOYSA-N 0.000 description 2
- GPDATMGCLOLJBJ-UHFFFAOYSA-N 1-fluoro-4-(4-prop-1-en-2-ylphenyl)benzene Chemical compound CC(=C)C1=CC=C(C=C1)C1=CC=C(F)C=C1 GPDATMGCLOLJBJ-UHFFFAOYSA-N 0.000 description 2
- KWSHGRJUSUJPQD-UHFFFAOYSA-N 1-phenyl-4-propan-2-ylbenzene Chemical group C1=CC(C(C)C)=CC=C1C1=CC=CC=C1 KWSHGRJUSUJPQD-UHFFFAOYSA-N 0.000 description 2
- PAMLTMDKARKMOU-UHFFFAOYSA-N 2-(3-methoxy-4-phenoxyphenyl)propan-2-ol Chemical compound COC=1C=C(C=CC1OC1=CC=CC=C1)C(C)(C)O PAMLTMDKARKMOU-UHFFFAOYSA-N 0.000 description 2
- QGTWZWNRBIVNML-UHFFFAOYSA-N 2-(3-phenylsulfanylphenyl)propan-2-ol Chemical compound C1(=CC=CC=C1)SC=1C=C(C=CC1)C(C)(C)O QGTWZWNRBIVNML-UHFFFAOYSA-N 0.000 description 2
- UQAXVZHQNKDTRP-UHFFFAOYSA-N 2-(4-butan-2-ylphenyl)propan-2-ol Chemical compound CCC(C)C1=CC=C(C(C)(C)O)C=C1 UQAXVZHQNKDTRP-UHFFFAOYSA-N 0.000 description 2
- JDYOGRRUTFRBDL-UHFFFAOYSA-N 2-(4-cyclohexylphenyl)propan-2-ol Chemical compound C1=CC(C(C)(O)C)=CC=C1C1CCCCC1 JDYOGRRUTFRBDL-UHFFFAOYSA-N 0.000 description 2
- GOKGIYHIVSGXDM-UHFFFAOYSA-N 2-(4-phenylphenyl)propan-2-ol Chemical compound C1=CC(C(C)(O)C)=CC=C1C1=CC=CC=C1 GOKGIYHIVSGXDM-UHFFFAOYSA-N 0.000 description 2
- SNGCLGKSXXZQGH-UHFFFAOYSA-N 2-(4-phenylsulfanylphenyl)propan-2-ol Chemical compound C1(=CC=CC=C1)SC1=CC=C(C=C1)C(C)(C)O SNGCLGKSXXZQGH-UHFFFAOYSA-N 0.000 description 2
- OHITVHATOPWRRY-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]propan-2-ol Chemical compound CC(C)CC1=CC=C(C(C)(C)O)C=C1 OHITVHATOPWRRY-UHFFFAOYSA-N 0.000 description 2
- SFJJGLUATPUIGV-UHFFFAOYSA-N 2-methoxy-1-phenoxy-4-prop-1-en-2-ylbenzene Chemical compound COC1=C(OC2=CC=CC=C2)C=CC(=C1)C(C)=C SFJJGLUATPUIGV-UHFFFAOYSA-N 0.000 description 2
- OSJLDCQZKGVESM-UHFFFAOYSA-N 2-methyl-1-phenoxy-4-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC(C)=C(OC2=CC=CC=C2)C=C1 OSJLDCQZKGVESM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MSDQNIRGPBARGC-UHFFFAOYSA-N 1-(4-cyclohexylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1CCCCC1 MSDQNIRGPBARGC-UHFFFAOYSA-N 0.000 description 1
- QCZZSANNLWPGEA-UHFFFAOYSA-N 1-(4-phenylphenyl)ethanone Chemical group C1=CC(C(=O)C)=CC=C1C1=CC=CC=C1 QCZZSANNLWPGEA-UHFFFAOYSA-N 0.000 description 1
- XUDYHODVSUXRPW-UHFFFAOYSA-N 1-(4-phenylsulfanylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1SC1=CC=CC=C1 XUDYHODVSUXRPW-UHFFFAOYSA-N 0.000 description 1
- KEAGRYYGYWZVPC-UHFFFAOYSA-N 1-[4-(2-methylpropyl)phenyl]ethanone Chemical compound CC(C)CC1=CC=C(C(C)=O)C=C1 KEAGRYYGYWZVPC-UHFFFAOYSA-N 0.000 description 1
- LGJJGWHKUXUJNR-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)phenyl]ethanone Chemical group C1=CC(C(=O)C)=CC=C1C1=CC=C(F)C=C1 LGJJGWHKUXUJNR-UHFFFAOYSA-N 0.000 description 1
- RUYZJEIKQYLEGZ-UHFFFAOYSA-N 1-fluoro-4-phenylbenzene Chemical group C1=CC(F)=CC=C1C1=CC=CC=C1 RUYZJEIKQYLEGZ-UHFFFAOYSA-N 0.000 description 1
- GAWAUDBMPDYIKL-UHFFFAOYSA-N 1-phenoxy-3-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC(OC=2C=CC=CC=2)=C1 GAWAUDBMPDYIKL-UHFFFAOYSA-N 0.000 description 1
- FXQJDGUGOZWQNL-UHFFFAOYSA-N 1-phenylsulfanyl-3-prop-1-en-2-ylbenzene Chemical compound C1(=CC=CC=C1)SC=1C=C(C=CC1)C(=C)C FXQJDGUGOZWQNL-UHFFFAOYSA-N 0.000 description 1
- YNEGVEGBQYYYNY-UHFFFAOYSA-N 1-phenylsulfanyl-4-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=C(SC2=CC=CC=C2)C=C1 YNEGVEGBQYYYNY-UHFFFAOYSA-N 0.000 description 1
- IXTMMFLDAGYLLL-UHFFFAOYSA-N 2-(3-phenoxyphenyl)propan-2-ol Chemical compound CC(C)(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 IXTMMFLDAGYLLL-UHFFFAOYSA-N 0.000 description 1
- YQEYLXLAWZVDQO-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)phenyl]propan-2-ol Chemical compound FC1=CC=C(C=C1)C1=C(C=CC=C1)C(C)(C)O YQEYLXLAWZVDQO-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical class CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO751753A NO751753L (enExample) | 1970-11-20 | 1975-05-16 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9155970A | 1970-11-20 | 1970-11-20 | |
| US12923771A | 1971-03-29 | 1971-03-29 | |
| NO243371A NO132724C (enExample) | 1970-11-20 | 1971-06-25 | |
| NO751753A NO751753L (enExample) | 1970-11-20 | 1975-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO751753L true NO751753L (enExample) | 1972-05-24 |
Family
ID=27484001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO751753A NO751753L (enExample) | 1970-11-20 | 1975-05-16 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO751753L (enExample) |
-
1975
- 1975-05-16 NO NO751753A patent/NO751753L/no unknown
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