SU482039A3 - Method for preparing biphenylyl butenoic acids or their derivatives - Google Patents
Method for preparing biphenylyl butenoic acids or their derivativesInfo
- Publication number
- SU482039A3 SU482039A3 SU1958291A SU1958291A SU482039A3 SU 482039 A3 SU482039 A3 SU 482039A3 SU 1958291 A SU1958291 A SU 1958291A SU 1958291 A SU1958291 A SU 1958291A SU 482039 A3 SU482039 A3 SU 482039A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- biphenylyl
- derivatives
- preparing
- acid
- acids
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 4
- PZYFUXBLYOGPDU-UHFFFAOYSA-N 2-(2-phenylphenyl)but-2-enoic acid Chemical class CC=C(C(O)=O)C1=CC=CC=C1C1=CC=CC=C1 PZYFUXBLYOGPDU-UHFFFAOYSA-N 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- -1 zinc chloride Chemical class 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ALIQGQKAABNEKG-UHFFFAOYSA-N 3-(3-fluoro-4-phenylphenyl)but-2-enoic acid Chemical compound FC1=CC(C(=CC(O)=O)C)=CC=C1C1=CC=CC=C1 ALIQGQKAABNEKG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- HPUCAWBFVXHLDN-UHFFFAOYSA-N 1-but-1-enyl-2-phenylbenzene Chemical class CCC=CC1=CC=CC=C1C1=CC=CC=C1 HPUCAWBFVXHLDN-UHFFFAOYSA-N 0.000 description 1
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical class NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GJMMXPXHXFHBPK-UHFFFAOYSA-N [P].[Cl] Chemical compound [P].[Cl] GJMMXPXHXFHBPK-UHFFFAOYSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000003946 cyclohexylamines Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- UFWDBCSYAKTZEV-UHFFFAOYSA-N ethyl 3-(3-fluoro-4-phenylphenyl)-3-hydroxybutanoate Chemical compound FC1=CC(C(C)(O)CC(=O)OCC)=CC=C1C1=CC=CC=C1 UFWDBCSYAKTZEV-UHFFFAOYSA-N 0.000 description 1
- FGIJCCMTPRPJLS-UHFFFAOYSA-N ethyl 3-(3-fluoro-4-phenylphenyl)but-2-enoate Chemical compound FC1=CC(C(C)=CC(=O)OCC)=CC=C1C1=CC=CC=C1 FGIJCCMTPRPJLS-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
- C07C245/14—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom having diazo groups bound to acyclic carbon atoms of a carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P3/00—Drugs for disorders of the metabolism
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
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- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/208—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being MX
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
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- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
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Description
(54) СПОСОБ ПОЛУЧЕНИЯ БИФЕНИЛИЛБУТЕНОВЫХ КИСЛОТ. ИЛИ ИХ ПРОИЗВОДНЫХ(54) METHOD FOR OBTAINING BIPHENYLYLBUTENE ACIDS. OR THEIR DERIVATIVES
которые обладают более высокой биопоги ческой активностью, чем известнее соедннени того же назначени , например фе- нилбутазон.which have a higher biopogic activity than the known compounds of the same purpose, for example phenylbutazone.
Способ заключаетс в том, что Д -ок сикислоты или их производные общей формулыThe method consists in the fact that the D-hydroxy acids or their derivatives of the general formula
«1"one
(и) он (and he
где I и в имеют указанные значени ,where I and in have the indicated values,
дегидратируют с помощью водоотнимак щегос средства в среде инертного растворител , несмешивающегос с водой, при нагревании не выще температуры кипени реакционной смеси с последующим выделением целевого продукта и/или переводом его в кислоту, соль, амид или сложный эфир известными способами .dehydrated with water-withdrawing means in an inert solvent immiscible with water, when heated, not more than the boiling point of the reaction mixture, followed by isolation of the target product and / or its conversion into acid, salt, amide or ester by known methods.
В качестве водоотщепл ющего средства целесообразно примен ть соли П1фидина или алкилпиридинов с галогеноводороднымц кислотами, бисульфат кали , соли металлов такие как хлорид цинка, а также кислоты, например П--толуолсульфокислоту, фосфорную , серную кислоту, или, если В означает алкоксигруппу, то преимущественно галоидангидриды неорганических кислот, например хлорокись фосфора. В качестве инертного растворител примен ют преимущественно бензол, толуол или ксилол.Salt of P1fidine or alkylpyridines with hydrohalic acids, potassium bisulfate, metal salts such as zinc chloride, as well as acids, for example, P-toluenesulfonic acid, phosphoric, sulfuric acid, or, if B means an alkoxy group, preferably inorganic acid halides, for example phosphorus oxychloride. Preferably, benzene, toluene or xylene is used as the inert solvent.
Следует указать, что при получении смеси соединений общей формулы , в которой А означает группу СНзIt should be noted that when preparing a mixture of compounds of the general formula, in which A represents a CH3 group
СН2 CH2
СН2-,CH2-,
эту смесь можно разделить на отдельные компоненты хроматографически или фракционной кристаллизацией.This mixture can be divided into individual components by chromatographic or fractional crystallization.
В качестве органических оснований дл получени солей кислот общей формулы используют, в частности, диэтаноламин, морфолин, циклогексиламин и пиперазин.Diethanolamine, morpholine, cyclohexylamine and piperazine are used as organic bases for the preparation of salts of acids of the general formula.
При получении соединени общей формулы I, в которой В - радикал.Upon receipt of the compound of general formula I in which B is a radical.
.Rj H-N .Rj H-N
изсложный эфир общей формулы J, в которой В - алкоксигруп а, подвергают вза4ester of general formula J, in which B is an alkoxy group, is subjected to mutual
имодействию с первичным или вторичным амщом. Взаимодействие провод т в инерт -: ном растворителе, предпочтительно в спирте , при повыщенных температуре и давле- НИИ. Амиды кислот общей формулы I можно получать также из соединений этой формулы, в которой В - атом галогена, т. е. из галогенангидрида кислоты, и соответствующего амина формулы and action with primary or secondary amschom. The reaction is carried out in an inert solvent, preferably in an alcohol, at elevated temperature and pressure. Amides of acids of general formula I can also be obtained from compounds of this formula, in which B is a halogen atom, i.e., from an acid halide, and the corresponding amine of formula
RSRS
Пример. 3-(2 -фтор-4-бифе нилил)-2-бутенова кислота. 4,5 г (0,015 мол ) этилового эфира 3-(2-фтор-4-бифенилил )-3-окси-масл ной кислоты (т, пл.Example. 3- (2-fluoro-4-bife nylyl) -2-butenoic acid. 4.5 g (0.015 mol) of 3- (2-fluoro-4-biphenylyl) -3-hydroxy-butyric acid ethyl ester (t, pl.
|71-73°С) раствор ют в 75 мл бензола и вместе с 3,5 г (0,0225 мол ) хлорркиси фосфора в течение 10 мин нагревают с обратным холодильником. Затем растворитель упаривают в вакууме, к остатку добавл ют лед ную воду, экстрагируют простым эфиром и отгон ют растворитель . Кристаллический остаток перекристал лизовывают из петролейного эфира. / Полученный этиловый эфир 3-(2 -фтор-4-бифенилил )-2-бутеновой кислоты (согласно ЯМР-спектру представл ет собой транс-форму) имеет т. пл. 53°С. Выход продукта 4,1 г (96% от теории).| 71-73 ° C) is dissolved in 75 ml of benzene and heated with reflux together with 3.5 g (0.0225 mol) of phosphorus chlorine for 10 minutes. The solvent is then evaporated in vacuo, ice water is added to the residue, it is extracted with ether and the solvent is distilled off. The crystalline residue is recrystallized from petroleum ether. The 3- (2-fluoro-4-biphenylyl) -2-butenoic acid ethyl ester obtained (according to the NMR spectrum is in the trans form) is m.p. 53 ° C. The product yield of 4.1 g (96% of theory).
Ч Раствор 4,1 г этилового эфира 3-( 2-фторбифен и лил)-2-бутеновой кислоты в 50 мл метанола с 1О мл, ЗО%-ного едкого кали нагревают с обратным холодильником в течение 2 час. Отгон ют метанол, добавл ют 200 мл воды и подкисл ют 15%-ной сол нс1 кислотой. Образовавщийс осадок экстрагируют простым эфиром. После сушки над Сульфатом натри упаривают простой эфир и остаток перекристаллизовывают из уксусного эфира. H A solution of 4.1 g of ethyl 3- (2-fluorobifen and lil) -2-butenoic acid in 50 ml of methanol with 10 ml of ZO% sodium hydroxide is heated under reflux for 2 hours. The methanol is distilled off, 200 ml of water is added and acidified with 15% hydrochloric acid. The resulting precipitate is extracted with ether. After drying over sodium sulfate, the ether is evaporated and the residue is recrystallized from ethyl acetate.
Получают 2,8 г (76% от теории) 3- (2 -фтор-4-бифенилцл)-2-бутеновой кислоты с т. пл. 177-1780С.2.8 g (76% of theory) of 3- (2-fluoro-4-biphenyl) -2-butenoic acid with m.p. 177-1780С.
Осажденна в ацетоне соль циклогексиламина имеет т. пл. 194-195°С.The cyclohexylamine salt precipitated in acetone has an mp. 194-195 ° C.
П р и м е р 2, 3-(2 -фтор-4-бифенилил )-2-бутенова кислота. 15 г (0,0547 мол )3-(2 -фтор-4-бифенилил)-3-окси-Macл ной Кислоты (т.пл. 108-ИО С) в 150м.| толуола с 1 г ft -толуолсульфокислоты при перемещивании нагревают с обратным холодильником и водоотделителем в течение часа. После охлаждени добавл йэт 1ОО мл уксусного эфира, промывают органический раствор водой и упаривают растворитель. Остаток перекристаллизовывают из уксусного эфира.PRI me R 2, 3- (2-fluoro-4-biphenylyl) -2-butenoic acid. 15 g (0.0547 mol) of 3- (2-fluoro-4-biphenylyl) -3-hydroxy-Acid Acid (mp. 108-IO C) at 150 m. | toluene with 1 g of ft-toluene sulfonic acid is heated under reflux and water separator during transfer for one hour. After cooling, it is added with 1 ml of ethyl acetate, the organic solution is washed with water and the solvent is evaporated. The residue is recrystallized from ethyl acetate.
Получают 8 г 3-(2 -фтор-4-бифенилил)-2-бутеновой кислоты с т, tin, 177-178 0.8 g of 3- (2-fluoro-4-biphenylyl) -2-butenoic acid are obtained with m, tin, 177-178 0.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2240441A DE2240441A1 (en) | 1972-08-17 | 1972-08-17 | NEW BIPHENYL DERIVATIVES AND METHOD OF MANUFACTURING |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU482039A3 true SU482039A3 (en) | 1975-08-25 |
Family
ID=5853790
Family Applications (11)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1958290A SU511846A3 (en) | 1972-08-17 | 1973-08-15 | The method of obtaining -biphenylbuttonic acids or their salts |
| SU1958291A SU482039A3 (en) | 1972-08-17 | 1973-08-15 | Method for preparing biphenylyl butenoic acids or their derivatives |
| SU1958288A SU484679A3 (en) | 1972-08-17 | 1973-08-15 | Method for preparing biphenyl derivatives |
| SU2069110A SU554810A3 (en) | 1972-08-17 | 1974-10-21 | The method of obtaining derivatives of biphenyl or their salts, or racemates, or optically active antipodes |
| SU7402069575A SU577967A3 (en) | 1972-08-17 | 1974-10-21 | Method of preparing substituted biphenylilbutyric acid or its esters,or its amides,or its salts |
| SU2069771A SU520030A3 (en) | 1972-08-17 | 1974-10-21 | Method for preparing substituted biphenylbutyric acid or its ester or its salt |
| SU2069774A SU552021A3 (en) | 1972-08-17 | 1974-10-21 | The method of obtaining derivatives of biphenyl or their salts |
| SU2069114A SU538658A3 (en) | 1972-08-17 | 1974-10-21 | The method of obtaining biphenylbutyric acids or their salts, or racemates, or optically active antipodes |
| SU2069576A SU561505A3 (en) | 1972-08-17 | 1974-10-21 | The method of obtaining 3- (4-biphenylyl) -buttonic acid or its salts |
| SU2069577A SU520907A3 (en) | 1972-08-17 | 1974-10-21 | Method for preparing substituted biphenylyl butyric acid or its salt |
| SU2069578A SU511847A3 (en) | 1972-08-17 | 1974-10-21 | Method for preparing substituted biphenylbutyric acid or its esters or salts |
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| Application Number | Title | Priority Date | Filing Date |
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| SU1958290A SU511846A3 (en) | 1972-08-17 | 1973-08-15 | The method of obtaining -biphenylbuttonic acids or their salts |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1958288A SU484679A3 (en) | 1972-08-17 | 1973-08-15 | Method for preparing biphenyl derivatives |
| SU2069110A SU554810A3 (en) | 1972-08-17 | 1974-10-21 | The method of obtaining derivatives of biphenyl or their salts, or racemates, or optically active antipodes |
| SU7402069575A SU577967A3 (en) | 1972-08-17 | 1974-10-21 | Method of preparing substituted biphenylilbutyric acid or its esters,or its amides,or its salts |
| SU2069771A SU520030A3 (en) | 1972-08-17 | 1974-10-21 | Method for preparing substituted biphenylbutyric acid or its ester or its salt |
| SU2069774A SU552021A3 (en) | 1972-08-17 | 1974-10-21 | The method of obtaining derivatives of biphenyl or their salts |
| SU2069114A SU538658A3 (en) | 1972-08-17 | 1974-10-21 | The method of obtaining biphenylbutyric acids or their salts, or racemates, or optically active antipodes |
| SU2069576A SU561505A3 (en) | 1972-08-17 | 1974-10-21 | The method of obtaining 3- (4-biphenylyl) -buttonic acid or its salts |
| SU2069577A SU520907A3 (en) | 1972-08-17 | 1974-10-21 | Method for preparing substituted biphenylyl butyric acid or its salt |
| SU2069578A SU511847A3 (en) | 1972-08-17 | 1974-10-21 | Method for preparing substituted biphenylbutyric acid or its esters or salts |
Country Status (19)
| Country | Link |
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| JP (2) | JPS49124052A (en) |
| AT (3) | AT328427B (en) |
| AU (2) | AU476340B2 (en) |
| BE (3) | BE803734A (en) |
| BG (3) | BG21844A3 (en) |
| CH (1) | CH588435A5 (en) |
| CS (3) | CS165386B2 (en) |
| DD (2) | DD108071A5 (en) |
| DE (1) | DE2240441A1 (en) |
| ES (4) | ES417883A1 (en) |
| FR (2) | FR2196167B1 (en) |
| GB (2) | GB1411495A (en) |
| HU (2) | HU166517B (en) |
| IL (2) | IL43004A0 (en) |
| NL (2) | NL7311301A (en) |
| PL (2) | PL94510B1 (en) |
| RO (2) | RO62918A (en) |
| SU (11) | SU511846A3 (en) |
| ZA (3) | ZA735629B (en) |
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| FR2457275A1 (en) * | 1979-05-21 | 1980-12-19 | Fabre Sa Pierre | P-BIPHENYL-4 METHYL-2 BUTEN-3 OIC ACIDS USEFUL IN THE TREATMENT OF RHUMATISMS |
| RU2686489C1 (en) * | 2018-12-27 | 2019-04-29 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Санкт-Петербургский государственный университет (СПбГУ)" | Method of producing α-diazocarbonyl compounds in aqueous medium |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB1382267A (en) * | 1970-05-05 | 1975-01-29 | Rorer Inc William H | Phenylalkanoic acid derivatives |
| BE776316R (en) * | 1971-03-10 | 1972-06-06 | Rorer Inc William H | Phenylacetic acid derivs - as antiinflammatory agents |
-
1972
- 1972-08-17 DE DE2240441A patent/DE2240441A1/en active Pending
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1973
- 1973-08-14 AT AT711273A patent/AT328427B/en not_active IP Right Cessation
- 1973-08-14 ES ES417883A patent/ES417883A1/en not_active Expired
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- 1973-08-14 ES ES417884A patent/ES417884A1/en not_active Expired
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- 1973-08-15 SU SU1958288A patent/SU484679A3/en active
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- 1973-08-16 JP JP48092053A patent/JPS49124052A/ja active Pending
- 1973-08-16 CS CS4903A patent/CS165386B2/cs unknown
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- 1973-08-16 AU AU59309/73A patent/AU476340B2/en not_active Expired
- 1973-08-16 AU AU59308/73A patent/AU5930873A/en not_active Expired
- 1973-08-16 JP JP48092052A patent/JPS49124051A/ja active Pending
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- 1973-08-17 FR FR7330076A patent/FR2196168B1/fr not_active Expired
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1974
- 1974-10-21 SU SU2069110A patent/SU554810A3/en active
- 1974-10-21 SU SU7402069575A patent/SU577967A3/en active
- 1974-10-21 SU SU2069771A patent/SU520030A3/en active
- 1974-10-21 SU SU2069774A patent/SU552021A3/en active
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- 1974-10-21 SU SU2069576A patent/SU561505A3/en active
- 1974-10-21 SU SU2069577A patent/SU520907A3/en active
- 1974-10-21 SU SU2069578A patent/SU511847A3/en active
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