DE2141925A1 - Neue 4-(4-biphenylyl)-4-oxo-buttersaeureamide - Google Patents
Neue 4-(4-biphenylyl)-4-oxo-buttersaeureamideInfo
- Publication number
- DE2141925A1 DE2141925A1 DE2141925A DE2141925A DE2141925A1 DE 2141925 A1 DE2141925 A1 DE 2141925A1 DE 2141925 A DE2141925 A DE 2141925A DE 2141925 A DE2141925 A DE 2141925A DE 2141925 A1 DE2141925 A1 DE 2141925A1
- Authority
- DE
- Germany
- Prior art keywords
- biphenylyl
- general formula
- oxo
- butyric acid
- fluoro
- 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
- CJDZICQLZGXQJF-UHFFFAOYSA-N 4-oxo-4-(4-phenylphenyl)butanamide Chemical class C1=CC(C(=O)CCC(=O)N)=CC=C1C1=CC=CC=C1 CJDZICQLZGXQJF-UHFFFAOYSA-N 0.000 title claims description 6
- 230000001741 anti-phlogistic effect Effects 0.000 title abstract 2
- -1 pyrrolidino, piperidino, morpholino Chemical group 0.000 claims abstract description 103
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- NABGULCRNBRRDQ-UHFFFAOYSA-N 5-(4-phenylphenyl)-3h-furan-2-one Chemical compound O1C(=O)CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 NABGULCRNBRRDQ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 9
- 239000004305 biphenyl Substances 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 150000004820 halides Chemical class 0.000 claims abstract description 4
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 229960002317 succinimide Drugs 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000002904 solvent Substances 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- IDWFXUSABXKHKN-UHFFFAOYSA-N FC1=C(C=CC=C1)C1=CC=C(C=C1)C(CCC(=O)N)=O Chemical compound FC1=C(C=CC=C1)C1=CC=C(C=C1)C(CCC(=O)N)=O IDWFXUSABXKHKN-UHFFFAOYSA-N 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 150000003254 radicals Chemical class 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 11
- UFACTWDSFYNOFG-UHFFFAOYSA-N C(CC)NC(CCC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)F)=O Chemical compound C(CC)NC(CCC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)F)=O UFACTWDSFYNOFG-UHFFFAOYSA-N 0.000 claims description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- APTHNDOPFRDPBL-UHFFFAOYSA-N C(C)NC(CCC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)F)=O Chemical compound C(C)NC(CCC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)F)=O APTHNDOPFRDPBL-UHFFFAOYSA-N 0.000 claims description 5
- ZPAKPRAICRBAOD-UHFFFAOYSA-N fenbufen Chemical group C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1 ZPAKPRAICRBAOD-UHFFFAOYSA-N 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 230000001681 protective effect Effects 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 239000002841 Lewis acid Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 229910015900 BF3 Inorganic materials 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 claims description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug 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 claims 1
- 239000002253 acid Substances 0.000 abstract description 9
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract description 2
- 150000008064 anhydrides Chemical class 0.000 abstract description 2
- 150000002825 nitriles Chemical class 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- QNMNMNZGJJDCSG-UHFFFAOYSA-N 3-(4-phenylphenyl)prop-2-enamide Chemical compound C1=CC(C=CC(=O)N)=CC=C1C1=CC=CC=C1 QNMNMNZGJJDCSG-UHFFFAOYSA-N 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 238000003756 stirring Methods 0.000 description 24
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 19
- 239000002244 precipitate Substances 0.000 description 19
- RXCXXXIESIJGNB-UHFFFAOYSA-N O=C1OC(C(C=C2)=CC=C2C(C=CC=C2)=C2F)=CC1 Chemical compound O=C1OC(C(C=C2)=CC=C2C(C=CC=C2)=C2F)=CC1 RXCXXXIESIJGNB-UHFFFAOYSA-N 0.000 description 16
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 16
- 229910021529 ammonia Inorganic materials 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 10
- 239000013543 active substance Substances 0.000 description 10
- 239000000829 suppository Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 229920002261 Corn starch Polymers 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 9
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 9
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 9
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
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- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
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- 238000001816 cooling Methods 0.000 description 6
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- 229910002012 Aerosil® Inorganic materials 0.000 description 5
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- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
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- 229960000583 acetic acid Drugs 0.000 description 4
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- 239000008298 dragée Substances 0.000 description 4
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- 239000000454 talc Substances 0.000 description 4
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- YRTUFFFNUSJOBZ-UHFFFAOYSA-N 4-[4-(2-fluorophenyl)phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1F YRTUFFFNUSJOBZ-UHFFFAOYSA-N 0.000 description 3
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- KLECYOQFQXJYBC-UHFFFAOYSA-N 1-fluoro-2-phenylbenzene Chemical group FC1=CC=CC=C1C1=CC=CC=C1 KLECYOQFQXJYBC-UHFFFAOYSA-N 0.000 description 2
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- 238000001556 precipitation Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (25)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE787782D BE787782A (fr) | 1971-08-20 | Nouveaux 4-(4-biphenylyl)-butyramides | |
| DE2141925A DE2141925A1 (de) | 1971-08-20 | 1971-08-20 | Neue 4-(4-biphenylyl)-4-oxo-buttersaeureamide |
| AT690473A AT323722B (de) | 1971-08-20 | 1972-08-10 | Verfahren zur herstellung neuer 4-(4-biphenylyl)-4-oxo-buttersäureamide |
| AT690573A AT323723B (de) | 1971-08-20 | 1972-08-10 | Verfahren zur herstellung neuer 4-(4-biphenylyl)-4-oxo-buttersäureamide |
| AT690373A AT323721B (de) | 1971-08-20 | 1972-08-10 | Verfahren zur herstellung neuer 4-(4-biphenylyl)-4-oxo-buttersäureamide |
| AT690673A AT323724B (de) | 1971-08-20 | 1972-08-10 | Verfahren zur herstellung neuer 4-(4-biphenylyl)-4-oxo-buttersäureamide |
| AT690572A AT318583B (de) | 1971-08-20 | 1972-08-10 | Verfahren zur Herstellung von neuen 4-(4-Biphenylyl)-4-oxo-buttersäureamiden |
| DD165129A DD99990A5 (OSRAM) | 1971-08-20 | 1972-08-18 | |
| AU45752/72A AU4575272A (en) | 1971-08-20 | 1972-08-18 | Chemical compounds |
| ZA725709A ZA725709B (en) | 1971-08-20 | 1972-08-18 | Improvements relating to 4-(4-biphenylyl)-butyric acid amides |
| GB3871272A GB1396748A (en) | 1971-08-20 | 1972-08-18 | 4-4-biphenylyl - butyramides |
| IL40161A IL40161A0 (en) | 1971-08-20 | 1972-08-18 | 4-(4-biphenylyl)-butyric acid amides,their preparation and pharmaceutical compositions containing them |
| FR7229733A FR2150809B1 (OSRAM) | 1971-08-20 | 1972-08-18 | |
| RO71986A RO59404A (OSRAM) | 1971-08-20 | 1972-08-18 | |
| NL7211363A NL7211363A (OSRAM) | 1971-08-20 | 1972-08-18 | |
| HUTO883A HU163806B (OSRAM) | 1971-08-20 | 1972-08-18 | |
| PL1972157362A PL83431B1 (OSRAM) | 1971-08-20 | 1972-08-19 | |
| JP47083254A JPS4829749A (OSRAM) | 1971-08-20 | 1972-08-19 | |
| US282363A US3882174A (en) | 1971-08-20 | 1972-08-21 | Amides of 4-(4{40 -biphenylyl)-butyric acid and its 4-hydroxy and 4-oxo derivatives |
| ES410836A ES410836A1 (es) | 1971-08-20 | 1973-01-20 | Procedimiento para la preparacion de nuevas amidas de acido4 - (4-bifenilil)-4-oxo-butirico. |
| ES410835A ES410835A1 (es) | 1971-08-20 | 1973-01-20 | Procedimiento para la preparacion de nuevas amidas de acido4 - (4-bifenilil)-4-oxo-butirico. |
| ES410837A ES410837A1 (es) | 1971-08-20 | 1973-01-20 | Procedimiento para la preparacion de nuevas amidas de acido4-(4-bifenilil)-4-oxo-butirico. |
| ES410832A ES410832A1 (es) | 1971-08-20 | 1973-01-20 | Procedimiento para la preparacion de nuevas amidas de acido4-(4-bifenilil)-4-oxo-butirico. |
| ES410834A ES410834A1 (es) | 1971-08-20 | 1973-01-20 | Procedimiento para la preparacion de nuevas amidas de acido4 - (4-bifenilil)-4-oxo-butirico. |
| ES410833A ES410833A1 (es) | 1971-08-20 | 1973-01-20 | Procedimiento para la preparacion de nuevas amidas de acido4-(4-bifenilil)-4-oxo-butirico. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2141925A DE2141925A1 (de) | 1971-08-20 | 1971-08-20 | Neue 4-(4-biphenylyl)-4-oxo-buttersaeureamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2141925A1 true DE2141925A1 (de) | 1973-03-08 |
Family
ID=5817371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2141925A Pending DE2141925A1 (de) | 1971-08-20 | 1971-08-20 | Neue 4-(4-biphenylyl)-4-oxo-buttersaeureamide |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS4829749A (OSRAM) |
| AT (5) | AT323722B (OSRAM) |
| AU (1) | AU4575272A (OSRAM) |
| DD (1) | DD99990A5 (OSRAM) |
| DE (1) | DE2141925A1 (OSRAM) |
| ES (6) | ES410835A1 (OSRAM) |
| HU (1) | HU163806B (OSRAM) |
| PL (1) | PL83431B1 (OSRAM) |
| RO (1) | RO59404A (OSRAM) |
| ZA (1) | ZA725709B (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51119170A (en) * | 1975-04-10 | 1976-10-19 | Shimakura Kogyosho:Kk | Process and apparatus for producing a toothbrush |
-
1971
- 1971-08-20 DE DE2141925A patent/DE2141925A1/de active Pending
-
1972
- 1972-08-10 AT AT690473A patent/AT323722B/de not_active IP Right Cessation
- 1972-08-10 AT AT690573A patent/AT323723B/de not_active IP Right Cessation
- 1972-08-10 AT AT690572A patent/AT318583B/de not_active IP Right Cessation
- 1972-08-10 AT AT690373A patent/AT323721B/de not_active IP Right Cessation
- 1972-08-10 AT AT690673A patent/AT323724B/de not_active IP Right Cessation
- 1972-08-18 ZA ZA725709A patent/ZA725709B/xx unknown
- 1972-08-18 AU AU45752/72A patent/AU4575272A/en not_active Expired
- 1972-08-18 HU HUTO883A patent/HU163806B/hu unknown
- 1972-08-18 DD DD165129A patent/DD99990A5/xx unknown
- 1972-08-18 RO RO71986A patent/RO59404A/ro unknown
- 1972-08-19 PL PL1972157362A patent/PL83431B1/pl unknown
- 1972-08-19 JP JP47083254A patent/JPS4829749A/ja active Pending
-
1973
- 1973-01-20 ES ES410835A patent/ES410835A1/es not_active Expired
- 1973-01-20 ES ES410836A patent/ES410836A1/es not_active Expired
- 1973-01-20 ES ES410834A patent/ES410834A1/es not_active Expired
- 1973-01-20 ES ES410833A patent/ES410833A1/es not_active Expired
- 1973-01-20 ES ES410832A patent/ES410832A1/es not_active Expired
- 1973-01-20 ES ES410837A patent/ES410837A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES410834A1 (es) | 1975-12-16 |
| ES410836A1 (es) | 1975-12-16 |
| JPS4829749A (OSRAM) | 1973-04-19 |
| AT318583B (de) | 1974-10-25 |
| DD99990A5 (OSRAM) | 1973-09-05 |
| AT323724B (de) | 1975-07-25 |
| PL83431B1 (OSRAM) | 1975-12-31 |
| ES410833A1 (es) | 1975-12-01 |
| ES410832A1 (es) | 1975-12-01 |
| AU4575272A (en) | 1974-02-21 |
| ES410837A1 (es) | 1975-12-01 |
| AT323721B (de) | 1975-07-25 |
| ES410835A1 (es) | 1975-12-16 |
| HU163806B (OSRAM) | 1973-10-27 |
| RO59404A (OSRAM) | 1976-06-15 |
| AT323722B (de) | 1975-07-25 |
| AT323723B (de) | 1975-07-25 |
| ZA725709B (en) | 1974-04-24 |
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