DE2917178A1 - 1-(2',6'-dimethylphenoxy)-propanderivate, verfahren zu ihrer herstellung und solche enthaltende arzneimittel - Google Patents
1-(2',6'-dimethylphenoxy)-propanderivate, verfahren zu ihrer herstellung und solche enthaltende arzneimittelInfo
- Publication number
- DE2917178A1 DE2917178A1 DE19792917178 DE2917178A DE2917178A1 DE 2917178 A1 DE2917178 A1 DE 2917178A1 DE 19792917178 DE19792917178 DE 19792917178 DE 2917178 A DE2917178 A DE 2917178A DE 2917178 A1 DE2917178 A1 DE 2917178A1
- Authority
- DE
- Germany
- Prior art keywords
- propane
- dimethylphenoxy
- radical
- general formula
- substituted
- 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.)
- Granted
Links
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 239000001294 propane Substances 0.000 title claims abstract description 11
- 239000000932 sedative agent Substances 0.000 title abstract description 4
- 230000003288 anthiarrhythmic effect Effects 0.000 title abstract 2
- 239000003416 antiarrhythmic agent Substances 0.000 title abstract 2
- 229940125723 sedative agent Drugs 0.000 title abstract 2
- 239000000543 intermediate Substances 0.000 title description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- -1 alkali metal azide Chemical class 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 10
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 6
- 230000002829 reductive effect Effects 0.000 claims abstract description 5
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 34
- 229910052740 iodine Inorganic materials 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 26
- ORWYJYFTKGSHEU-UHFFFAOYSA-N 1,3-dimethyl-2-propoxybenzene Chemical class CCCOC1=C(C)C=CC=C1C ORWYJYFTKGSHEU-UHFFFAOYSA-N 0.000 claims description 19
- 125000003277 amino group Chemical group 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- HJFXAWKTYCNUQJ-UHFFFAOYSA-N 2-(2-azidopropoxy)-1,3-dimethylbenzene Chemical compound [N-]=[N+]=NC(C)COC1=C(C)C=CC=C1C HJFXAWKTYCNUQJ-UHFFFAOYSA-N 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- DUAJIKVIRGATIW-UHFFFAOYSA-N trinitrogen(.) Chemical compound [N]=[N+]=[N-] DUAJIKVIRGATIW-UHFFFAOYSA-N 0.000 claims description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 5
- 238000005917 acylation reaction Methods 0.000 claims description 5
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 230000009467 reduction Effects 0.000 claims description 5
- NWINJJIRFPNRDA-UHFFFAOYSA-N 1-(2,6-dimethylphenoxy)propan-2-yl methanesulfonate Chemical compound CS(=O)(=O)OC(C)COC1=C(C)C=CC=C1C NWINJJIRFPNRDA-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 230000010933 acylation Effects 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- WLAXWUTWXLCXNM-UHFFFAOYSA-N 1-(2,6-dimethylphenoxy)propan-2-yl 2,2,2-trichloroacetate Chemical compound CC1=C(OCC(C)OC(C(Cl)(Cl)Cl)=O)C(=CC=C1)C WLAXWUTWXLCXNM-UHFFFAOYSA-N 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 230000001624 sedative effect Effects 0.000 abstract description 6
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 231100000331 toxic Toxicity 0.000 abstract description 3
- 230000002588 toxic effect Effects 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 19
- VLPIATFUUWWMKC-UHFFFAOYSA-N mexiletine Chemical compound CC(N)COC1=C(C)C=CC=C1C VLPIATFUUWWMKC-UHFFFAOYSA-N 0.000 description 11
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000007858 starting material Substances 0.000 description 9
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000005660 chlorination reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- QFOWJPBDGSGFEJ-UHFFFAOYSA-N 1-(2,6-dimethylphenoxy)propan-2-ol Chemical compound CC(O)COC1=C(C)C=CC=C1C QFOWJPBDGSGFEJ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000007664 blowing Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- XLJQPXVBQNJNLW-UHFFFAOYSA-N 1-methylaziridine Chemical compound CN1CC1 XLJQPXVBQNJNLW-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 206010047281 Ventricular arrhythmia Diseases 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- VQFAIAKCILWQPZ-UHFFFAOYSA-N bromoacetone Chemical compound CC(=O)CBr VQFAIAKCILWQPZ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 208000003663 ventricular fibrillation Diseases 0.000 description 2
- REIIOHUYMPSAPS-WVLIHFOGSA-N (ne)-n-[(1-methyl-2h-pyridin-6-yl)methylidene]hydroxylamine;hydrochloride Chemical class Cl.CN1CC=CC=C1\C=N\O REIIOHUYMPSAPS-WVLIHFOGSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SCDVGDQWXWIKEA-UHFFFAOYSA-N 1-(2,6-dimethylphenoxy)propan-2-yl 4-methylbenzenesulfonate Chemical compound CC1=C(OCC(C)OS(=O)(=O)C2=CC=C(C=C2)C)C(=CC=C1)C SCDVGDQWXWIKEA-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003440 anti-fibrillation Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- NFEIBWMZVIVJLQ-UHFFFAOYSA-N mexiletine hydrochloride Chemical compound [Cl-].CC([NH3+])COC1=C(C)C=CC=C1C NFEIBWMZVIVJLQ-UHFFFAOYSA-N 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- UMSVPCYSAUKCAZ-UHFFFAOYSA-N propane;hydrochloride Chemical compound Cl.CCC UMSVPCYSAUKCAZ-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- 206010047302 ventricular tachycardia Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU78GO1401A HU176102B (en) | 1978-04-28 | 1978-04-28 | Process for preparing phenylethers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2917178A1 true DE2917178A1 (de) | 1979-11-08 |
| DE2917178C2 DE2917178C2 (enrdf_load_html_response) | 1989-01-12 |
Family
ID=10996855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792917178 Granted DE2917178A1 (de) | 1978-04-28 | 1979-04-27 | 1-(2',6'-dimethylphenoxy)-propanderivate, verfahren zu ihrer herstellung und solche enthaltende arzneimittel |
Country Status (16)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5932685A (ja) * | 1982-08-16 | 1984-02-22 | Hitachi Constr Mach Co Ltd | 可変容量ポンプの容量制御装置 |
| JPS60146713U (ja) * | 1984-03-09 | 1985-09-28 | 株式会社 名機製作所 | 作動油昇温回路を備えた射出成形機 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1205958A (en) * | 1966-09-16 | 1970-09-23 | Boehringer Sohn Ingelheim | A novel substituted 1-phenoxy-2-aminopropane |
-
1978
- 1978-04-28 HU HU78GO1401A patent/HU176102B/hu unknown
-
1979
- 1979-04-16 IN IN368/CAL/79A patent/IN150039B/en unknown
- 1979-04-16 IL IL57080A patent/IL57080A/xx unknown
- 1979-04-24 ES ES479867A patent/ES479867A1/es not_active Expired
- 1979-04-24 CS CS792855A patent/CS208498B2/cs unknown
- 1979-04-25 YU YU996/79A patent/YU41861B/xx unknown
- 1979-04-25 FI FI791340A patent/FI791340A7/fi not_active Application Discontinuation
- 1979-04-26 DD DD79212518A patent/DD143249A1/de unknown
- 1979-04-26 DK DK172679A patent/DK166820B1/da active IP Right Grant
- 1979-04-26 PL PL21518179A patent/PL215181A1/xx unknown
- 1979-04-26 PL PL1979225752A patent/PL125109B1/pl unknown
- 1979-04-26 PL PL1979225751A patent/PL126968B1/pl unknown
- 1979-04-26 AT AT0312379A patent/AT365169B/de not_active IP Right Cessation
- 1979-04-26 SU SU792760454A patent/SU980614A3/ru active
- 1979-04-27 JP JP5157979A patent/JPS5547641A/ja active Granted
- 1979-04-27 NO NO791412A patent/NO148450C/no unknown
- 1979-04-27 CA CA326,489A patent/CA1132598A/en not_active Expired
- 1979-04-27 DE DE19792917178 patent/DE2917178A1/de active Granted
-
1980
- 1980-05-23 SU SU802925097A patent/SU980616A3/ru active
- 1980-05-23 SU SU802925098A patent/SU978724A3/ru active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1205958A (en) * | 1966-09-16 | 1970-09-23 | Boehringer Sohn Ingelheim | A novel substituted 1-phenoxy-2-aminopropane |
Also Published As
| Publication number | Publication date |
|---|---|
| IN150039B (enrdf_load_html_response) | 1982-07-03 |
| HU176102B (en) | 1980-12-28 |
| YU99679A (en) | 1982-10-31 |
| IL57080A0 (en) | 1979-07-25 |
| NO791412L (no) | 1979-10-30 |
| SU980614A3 (ru) | 1982-12-07 |
| DD143249A1 (de) | 1980-08-13 |
| DK166820B1 (da) | 1993-07-19 |
| DE2917178C2 (enrdf_load_html_response) | 1989-01-12 |
| ATA312379A (de) | 1981-05-15 |
| PL125109B1 (en) | 1983-03-31 |
| JPS6338979B2 (enrdf_load_html_response) | 1988-08-03 |
| YU41861B (en) | 1988-02-29 |
| SU980616A3 (ru) | 1982-12-07 |
| AT365169B (de) | 1981-12-28 |
| CA1132598A (en) | 1982-09-28 |
| SU978724A3 (ru) | 1982-11-30 |
| NO148450B (no) | 1983-07-04 |
| ES479867A1 (es) | 1980-08-16 |
| NO148450C (no) | 1983-10-12 |
| FI791340A7 (fi) | 1981-01-01 |
| JPS5547641A (en) | 1980-04-04 |
| PL215181A1 (enrdf_load_html_response) | 1980-01-28 |
| DK172679A (da) | 1979-10-29 |
| IL57080A (en) | 1983-05-15 |
| CS208498B2 (en) | 1981-09-15 |
| PL126968B1 (en) | 1983-09-30 |
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