GB1116432A - Biphenylyl aliphatic acids and their salts and esters - Google Patents
Biphenylyl aliphatic acids and their salts and estersInfo
- Publication number
- GB1116432A GB1116432A GB38168/65A GB3816865A GB1116432A GB 1116432 A GB1116432 A GB 1116432A GB 38168/65 A GB38168/65 A GB 38168/65A GB 3816865 A GB3816865 A GB 3816865A GB 1116432 A GB1116432 A GB 1116432A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- radical
- phenyl
- halogen atom
- sulphamoyl
- 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.)
- Expired
Links
- 150000002148 esters Chemical class 0.000 title abstract 4
- 150000003839 salts Chemical class 0.000 title abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 38
- -1 alkynyl radical Chemical class 0.000 abstract 18
- 239000002253 acid Substances 0.000 abstract 11
- 125000005843 halogen group Chemical group 0.000 abstract 11
- 238000000034 method Methods 0.000 abstract 9
- 150000007513 acids Chemical class 0.000 abstract 8
- 125000004953 trihalomethyl group Chemical group 0.000 abstract 8
- 238000006243 chemical reaction Methods 0.000 abstract 7
- 125000003545 alkoxy group Chemical group 0.000 abstract 6
- 125000004414 alkyl thio group Chemical group 0.000 abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 239000012442 inert solvent Substances 0.000 abstract 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 3
- 230000003301 hydrolyzing effect Effects 0.000 abstract 3
- 239000003513 alkali Substances 0.000 abstract 2
- 229910001515 alkali metal fluoride Inorganic materials 0.000 abstract 2
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 2
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 abstract 1
- LYINHPAEAYJDIR-UHFFFAOYSA-N 92-89-7 Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C([N+]([O-])=O)C=C1 LYINHPAEAYJDIR-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 1
- 238000003747 Grignard reaction Methods 0.000 abstract 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 1
- 229910005948 SO2Cl Inorganic materials 0.000 abstract 1
- 229910006024 SO2Cl2 Inorganic materials 0.000 abstract 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 238000000297 Sandmeyer reaction Methods 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 125000001118 alkylidene group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- QRZAKQDHEVVFRX-UHFFFAOYSA-N biphenyl-4-ylacetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C1=CC=CC=C1 QRZAKQDHEVVFRX-UHFFFAOYSA-N 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 239000012954 diazonium Substances 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 229960000192 felbinac Drugs 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 229920001021 polysulfide Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229910001923 silver oxide Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000012991 xanthate Substances 0.000 abstract 1
Classifications
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- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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- C07C303/16—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by oxidation of thiols, sulfides, hydropolysulfides, or polysulfides with formation of sulfo or halosulfonyl groups
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- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Abstract
Compounds, mostly novel, of the general formulae <FORM:1116432/C2/1> <FORM:1116432/C2/2> <FORM:1116432/C2/3> <FORM:1116432/C2/4> (wherein R1 is H and R2 is a C1- 5 alkyl or haloalkyl or C2- 5 alkenyl or alkynyl radical, or R1 and R2 together form a methylene, C2- 5 alkylidene or ethylene group, R11 is H and R1 is a halogen atom or a C1- 5 alkoxy group or R1 and R11 are both C1- 5 alkyl groups, R3 and R4 each represent a halogen atom or a C1- 5 alkyl, alkylthio or alkylsulphonyl, di-(C1- 5 alkyl)-sulphamoyl, trihalomethyl, benzylthio, SH, NH2, di-(C1- 5 alkyl)-amino, CN, NO2, CONH2, di-(C1- 5 - alkyl) - carbamoyl, C1- 6 alkanoylamino or phenyl radical, each of n and m is 0, 1 or 2 provided n + m is 1, 2 or 3, or may be zero in Formula IV, and Ra represents H or a C1- 5 alkyl, C3- 5 alkynyl, C3- 6 cycloalkyl, mono- or poly - (C1- 5 alkoxy) - C3- 6 cycloalkyl, aralkyl, phenyl, (C1- 6 alkanoyl)-aminophenyl, carboxyphenyl, carbamoyphenyl, mono- or poly-(C1- 5 alkoxy)-C1- 5 alkyl, C1- 5 polyhydroxyalkyl, di - (C1- 5 alkyl) - amino - C1- 5 alkyl o amino-(C3- 6 cycloalkyl)-methyl radical, with the proviso that if the C atom alpha to the carboxyl group carries two H atoms (I), an alkyl or alkenyl group (II) or two alkyl groups (III) and if also m = 0 and/or R3 is halogen, alkyl or dialkylamino, then n is not 0 and R4 is not alkyl or phenyl) are prepared by the following processes: (I) for free acids I: (A) heating a compound of the general formula <FORM:1116432/C2/5> (wherein R5 and R6 each represent a halogen atom or a C1- 5 alkyl, alkylthio or alkylsulphonyl, di - (C1- 5 alkyl) - sulphamoyl, trihalomethyl, benzylthio, SH, di-(C1- 5 alkyl)-amino, CONH2, di-(C1- 5 alkyl)- carbamoyl, C1- 6 alkanoylamino or phenyl radical) with ammonium polysulphide in a reaction-inert organic solvent or with sulphur in an organic amine, hydrolysing the product with an alkali or alkaline-earth metal base and acidifying, and, if desired, when n + m = 1 or 2, nitrating the product and, if desired, reducing the NO2 group(s) to NH2, and, if desired, replacing NH2 by CN by the Sandmeyer reaction; (B) reacting a compound of the general formula <FORM:1116432/C2/6> (wherein R7 and R8 each represent a halogen atom or a di-(C1- 5 alkyl)-sulphamoyl, NO2, di-(C1- 5 alkyl)-carbamoyl, trihalomethyl, phenyl or C1- 5 alkyl radical) with an alkali or alkaline -earth metal hypohalite in a reaction-inert solvent, consuming the excess of hypohalite with a reducing agent and acidifying the reaction mixture with a mineral acid to form a 4-phenylbenzoic acid of the general formula <FORM:1116432/C2/7> reacting this with an inorganic acid halide in a reaction-inert solvent, reacting the resulting acid halide with diazomethane in a reactioninert solvent at room temperature to form a 4-phenyldiazoacetophenone, and treating this, in the presence of a silver oxide, copper or platinum catalyst, with water to form the desired acid or with a C1- 5 alkanol to form the correspondin ester, which may then be saponified, and then in either case, if desired, reducing NO2 to NH2 and, if desired, dialkylating or acylating the latter or replacing it by SH or CN by diazotization and reaction of the diazonium salt with a C1- 5 alkyl xanthate or cuprous cyanide, and further, if desired, alkylating the SH group or subjecting it to the process-SH--> -SO3H ---> -SO2Cl ---> -SO2N(C1- 5 alkyl)2, or converting -CN to -CONH2 by alkaline hydrolysis; (C) carrying out process (A) with a starting material in which n + m = 0 and mono-, di- or tri-nitrating the resulting 4-biphenylylacetic acid, followed, if desired, by conversion of the NO2 group(s) as in (A); (II) for free acids II: (A) carrying out the following process <FORM:1116432/C2/8> (wherein R0 represents a C1- 5 alkyl radical, R00 represents CH2 or a C2- 5 alkylidene radical, and each of R9 and R10 represents a halogen atom or a C1- 5 alkyl, alkylthio or alkylsulphonyl, di-(C1- 5 alkyl)-sulphamoyl, trihalomethyl, benzylthio, SH, NH2, di-(C1- 5 alkyl)-amino, CN, di-(C1- 5 alkyl)-carbamoyl or phenyl radical, any groups containing active H being benzylated at step 7 and subsequently liberated), followed by hydrolysis of the product of step 8, and, if desired, introducing and converting nitro groups as in (I); (B) carrying out the following process <FORM:1116432/C2/9> (wherein R11 and R12 each represent a halogen atom or a C1- 5 alkyl, alkylthio or alkylsulphonyl, di-(C1- 5 alkyl)-sulphamoyl, NO2, trihalomethyl phenyl-substituted C1- 5 alkyl or di-(C1- 5 alkyl)-carbamoyl radical, R13 represents an alkyl radical, and R* represents an aralkyl or C1- 5 alkyl radical), step 1 being effected with an R13 oxalate in the presence of a strong base derived from an alkali metal, step 2 with an R2 halide and step 3 with an alkali metal alkoxide followed by acidification, the process being followed, if desired, by conversion of NO2 as in (I); (III) for free acids III: (A) (when R11 is H and R1 is halogen or C1- 5 alkoxy) treating a compound of the general formula <FORM:1116432/C2/10> (wherein R14 and R15 each represent a halogen atom or a C1- 5 alkyl, CN, NO2, trihalomethyl, di-(C1- 5 alkyl)-sulphamoyl or di-(C1- 5 alkyl)-carbamoyl radical) with SO2Cl2 and, if desired, reacting the resulting a -chloro compound with Na and a C1- 5 alkanol to replace Cl by C1- 5 alkoxy, or with an alkali metal fluoride to replace Cl by F, or hydrolysing it to replace Cl by OH, converting this to its tosyl ester and reacting the latter with an alkali metal fluoride to form an a -fluoro compound, any of these processes being followed, if desired, by conversion of NO2 as in (I), or also oxidizing -S-(C1- 5 alkyl) to -SO2-(C1- 5 alkyl (when R1 and R11 each represent a C1- 5 alkyl radical) reacting an amide of the general formula <FORM:1116432/C2/11> (wherein R16 and R17 each represent a halogen atom or a C1- 5 alkyl, phenyl, trihalomethyl, di-(C1- 5 alkyl)-sulphamoyl, NO2, CONH2 or di-(C1- 5 alkyl)-carbamoyl radical) with a dehydrating agent to produce the corresponding nitrile, reacting this with a C1- 5 alkyl halide in an inert solvent in the presence of an alkali metal amide or hydride and hydrolysing the resulting a ,a -di-C1- 5 alkyl) -4-biphenylylacetonitrile compound, followed, if desired, by conversion of NO2 as in (I); (IV) for free acids IV: carrying out the following process: <FORM:1116432/C2/12> (wherein R3 and R4 each represent a halogen atom or a trihalomethyl, C1- 5 alkyl or alkylthio, benzylthio, phenyl or di-(C1- 5 alkyl)-sulphamoyl radical and #j represents phenyl), step 1 being effected by reaction with a (C1- 5 alkoxy) carbonylmethylene triphenylphosphorane in an inert solvent, step 3 by a Grignard reaction and step 5 by oxidation, and the process being followed, if desired, by introduction and conversion of NO2 as in (I) and (III); (V) for the esters, omitting the hydrolysis steps in certain of the foregoing processes, or esterifying the free acids. Some of the products may be resolved into optically active enantiomorphs. The free acids may also be converted into their salts. The preparation of the following starting materials and intermediates is described: 31-chloro - 41 - phenylacetophenone, 41 - (p - biphenylyl) -acetophenone, 21 - and 31 - methyl-41 - phenylacetophenone, 21 - chloro - 4 - biphenylyl methyl ketone, 4-(p-nitrophenyl)-benzoic acid, 41-(p-nitrophenyl)-diazoacetophenone, ethyl 41-benzyloxycarbonyl-4-biphenylyl-acetate, ethyl 41 - carboxy - 4 - biphenylylacetate, and 41-fluoro-4-biphenylylacetamide. Pharmaceutical compositions.-Tablets and capsules, having anti-inflammatory activity, contain acids or esters of general Formulae I, II, III, and IV, or non-toxic pharmaceutically acceptable salts of the acids, as active ingredients.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US39555364A | 1964-09-10 | 1964-09-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1116432A true GB1116432A (en) | 1968-06-06 |
Family
ID=23563534
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB38600/67A Expired GB1116433A (en) | 1964-09-10 | 1965-09-07 | Amides of biphenylyl aliphatic acids |
GB38168/65A Expired GB1116432A (en) | 1964-09-10 | 1965-09-07 | Biphenylyl aliphatic acids and their salts and esters |
GB38711/67A Expired GB1116434A (en) | 1964-09-10 | 1965-09-07 | Biphenylyl-substituted aliphatic aldehydes and their acetals |
GB38712/67A Expired GB1116435A (en) | 1964-09-10 | 1965-09-07 | Biphenylyl-substituted aliphatic alcohols and their ethers |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB38600/67A Expired GB1116433A (en) | 1964-09-10 | 1965-09-07 | Amides of biphenylyl aliphatic acids |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB38711/67A Expired GB1116434A (en) | 1964-09-10 | 1965-09-07 | Biphenylyl-substituted aliphatic aldehydes and their acetals |
GB38712/67A Expired GB1116435A (en) | 1964-09-10 | 1965-09-07 | Biphenylyl-substituted aliphatic alcohols and their ethers |
Country Status (9)
Country | Link |
---|---|
US (1) | US3624142A (en) |
BE (1) | BE669347A (en) |
BR (1) | BR6572746D0 (en) |
CH (1) | CH490309A (en) |
ES (1) | ES317635A1 (en) |
FR (5) | FR1460659A (en) |
GB (4) | GB1116433A (en) |
IL (1) | IL24046A (en) |
NL (1) | NL6511845A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5033052B1 (en) * | 1968-10-25 | 1975-10-27 | ||
JPS5034556B1 (en) * | 1970-07-13 | 1975-11-10 | ||
US4163788A (en) | 1968-03-27 | 1979-08-07 | Ciba-Geigy Corporation | Tertiary aminoacids |
US4316850A (en) | 1968-03-27 | 1982-02-23 | Ciba-Geigy Corporation | Tertiary aminoacids |
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US4053639A (en) * | 1964-01-24 | 1977-10-11 | The Boots Company Limited | Therapeutically active phenylalkane derivatives |
US3674832A (en) * | 1968-08-22 | 1972-07-04 | Schering Corp | Cyclopropane carboxylic acid derivatives |
GB1268008A (en) * | 1969-07-09 | 1972-03-22 | Bdh Pharmaceuticals Ltd | ESTERS OF p-BYPHENYLYLACETIC ACID |
GB1275927A (en) * | 1969-07-16 | 1972-06-01 | Bdh Pharmaceuticals Ltd | ESTERS OF p-BIPHENYLYLACETIC ACID |
US3981905A (en) * | 1970-03-16 | 1976-09-21 | Boots Pure Drug Company Limited | 2-(Substituted phenyl) propionic acids |
US4192890A (en) * | 1970-04-15 | 1980-03-11 | Roussel Uclaf | Novel benzoylphenylacetic acid esters |
US3864384A (en) * | 1970-05-05 | 1975-02-04 | Rorer Inc William H | Substituted phenylacetic acid compounds |
US3941821A (en) * | 1970-05-05 | 1976-03-02 | William H. Rorer, Inc. | 2-Thiosulfo biphenylylacetic acids |
GB1359987A (en) * | 1970-10-12 | 1974-07-17 | Boots Co Ltd | 2-substituted biphenylyl propionic acids |
US4052514A (en) * | 1971-03-26 | 1977-10-04 | The Boots Company Limited | Trihalosubstituted biphenylyl propionic acids |
GB1437783A (en) * | 1972-09-22 | 1976-06-03 | Boots Co Ltd | 2-substituted biphenylyl acetic acids and derivatives thereof |
US3857880A (en) * | 1971-07-20 | 1974-12-31 | Schering Corp | Cyclopropane carboxylic acid derivatives |
BE787782A (en) * | 1971-08-20 | 1973-02-19 | Thomae Gmbh Dr K | NEW 4- (4-BIPHENYLYL) -BUTYRAMIDES |
DE2205732A1 (en) * | 1972-02-08 | 1973-08-16 | Thomae Gmbh Dr K | NEW 4- (4-BIPHENYLYL) -BUTIC ACID DERIVATIVES |
US4048332A (en) * | 1972-06-15 | 1977-09-13 | The Boots Company Limited | Phenylalkanoic acids |
GB1396726A (en) * | 1972-06-15 | 1975-06-04 | Boots Co Ltd | Phenylalkanoic acids |
US3987197A (en) * | 1972-08-17 | 1976-10-19 | Boehringer Ingelheim Gmbh | 3-(2'-fluoro-4-biphenylyl)-butyric acid and salts thereof |
DE2341506A1 (en) * | 1973-08-16 | 1975-02-27 | Thomae Gmbh Dr K | NEW BIPHENYL DERIVATIVES AND THE PROCESS FOR THEIR PRODUCTION |
US3957861A (en) * | 1973-11-07 | 1976-05-18 | The Upjohn Company | Biphenylylpropionic acids and esters |
GB1497044A (en) * | 1974-03-07 | 1978-01-05 | Prodotti Antibiotici Spa | Salts of phenyl-alkanoic acids |
US4035509A (en) * | 1974-04-22 | 1977-07-12 | Syntex (U.S.A.) Inc. | Methods and compositions for the use of 2-carboxy-5-oxo-5H-dibenzo[a,d]cycloheptenes, salts and esters thereof |
US4020094A (en) * | 1974-04-22 | 1977-04-26 | Syntex (U.S.A.) Inc. | 2-Substituted-5-oxo-5H-dibenzo[a,d]cycloheptenes, the salts and esters thereof, having pharmaceutical activity |
ES446581A1 (en) * | 1975-04-04 | 1977-06-16 | Boots Co Ltd | Biphenylhydroxypropionic acid derivatives |
US4333951A (en) * | 1977-11-15 | 1982-06-08 | A. H. Robins Company, Inc. | 2-Amino-6-biphenylacetic acids |
US4324904A (en) * | 1979-12-19 | 1982-04-13 | The Upjohn Company | Processes for the preparation of hydratropic acids and esters |
FR2498449A1 (en) * | 1981-01-23 | 1982-07-30 | Fabre Sa Pierre | Medicaments contg. halo-bi:phenyl carboxylic acid(s) - useful as hypolipaemic and hypocholesterolaemic agents |
US4731484A (en) * | 1985-01-18 | 1988-03-15 | The Dow Chemical Company | Haloacetyl derivatives of aromatic compounds |
FR2584403B1 (en) * | 1985-07-08 | 1987-10-23 | Pf Medicament | HALOGENO BIPHENYL PRIMARY ALCOHOL DERIVATIVES USEFUL IN THERAPEUTICS IN THE TREATMENT OF ATHEROSCLEROSIS |
IT1197289B (en) * | 1986-09-26 | 1988-11-30 | S I F I Societa Ind Farmaceuti | LYSINE SALT OF 4-BIPHENYLACETIC ACID AND ITS OPHTHALMIC COMPOSITIONS |
US5663416A (en) * | 1990-05-22 | 1997-09-02 | Cortech Inc. | Oxidant sensitive and insensitive aromatic esters as inhibitors of human neutrophil elastase |
TW348175B (en) * | 1993-01-06 | 1998-12-21 | Hoechst Ag | Process for the preparation of biphenyl derivatives |
US5691376A (en) * | 1994-02-17 | 1997-11-25 | American Home Products Corporation | Substituted biphenyl derivatives |
CA2182792A1 (en) * | 1994-02-17 | 1995-08-24 | Thomas J. Caggiano | Substituted biphenyl derivatives as phosphodiesterase inhibitors |
US5593994A (en) * | 1994-09-29 | 1997-01-14 | The Dupont Merck Pharmaceutical Company | Prostaglandin synthase inhibitors |
IL115995A0 (en) * | 1994-11-15 | 1996-01-31 | Bayer Ag | Substituted 4-biarylbutyric or 5-biarylpentanoic acids and derivatives as matrix metalloprotease inhibitors |
US5789434A (en) * | 1994-11-15 | 1998-08-04 | Bayer Corporation | Derivatives of substituted 4-biarylbutyric acid as matrix metalloprotease inhibitors |
DK0933346T3 (en) | 1996-07-31 | 2004-03-29 | Shionogi & Co | New p-terphenyl compounds |
US5994379A (en) * | 1998-02-13 | 1999-11-30 | Merck Frosst Canada, Inc. | Bisaryl COX-2 inhibiting compounds, compositions and methods of use |
KR100809489B1 (en) * | 2001-10-10 | 2008-03-03 | 씨제이제일제당 (주) | 4'-Methanesulfonyl-biphenyl derivatives as a highly selective cyclooxygenase-2 inhibitor |
CN1944378A (en) * | 2006-10-23 | 2007-04-11 | 广东中科药物研究有限公司 | Biphenyl ammonia acetate butantriol salt and its preparing method |
CN106748721B (en) * | 2016-11-17 | 2019-06-21 | 山东铂源药业有限公司 | A kind of preparation method of the chloro- 5- iodo-benzoic acid of 2- |
CN114790141B (en) * | 2022-05-25 | 2023-03-07 | 大连理工大学 | Method for synthesizing chloroallyl ester without catalysis of transition metal |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2921939A (en) * | 1955-11-28 | 1960-01-19 | Metal & Thermit Corp | Process for preparing alpha-substituted acetic acids |
FR1152761A (en) * | 1956-04-07 | 1958-02-25 | Maggioni & C Spa | Process for the preparation of 4-diphenylyl-alkyl-acetic acids |
US3043746A (en) * | 1959-11-02 | 1962-07-10 | Vismara Francesco Spa | 2-(4-biphenylyl)-delta-hexenoic acid and derivatives as anticholesterinemic agents |
US3120551A (en) * | 1961-03-20 | 1964-02-04 | Warner Lambert Pharmaceutical | 5-(4-biphenylyl)-3-methylvaleric acid and functional derivatives thereof |
-
1964
- 1964-09-10 US US395553A patent/US3624142A/en not_active Expired - Lifetime
-
1965
- 1965-07-28 IL IL24046A patent/IL24046A/en unknown
- 1965-08-31 BR BR172746/65A patent/BR6572746D0/en unknown
- 1965-09-01 CH CH1222365A patent/CH490309A/en not_active IP Right Cessation
- 1965-09-07 GB GB38600/67A patent/GB1116433A/en not_active Expired
- 1965-09-07 GB GB38168/65A patent/GB1116432A/en not_active Expired
- 1965-09-07 FR FR30712A patent/FR1460659A/en not_active Expired
- 1965-09-07 GB GB38711/67A patent/GB1116434A/en not_active Expired
- 1965-09-07 GB GB38712/67A patent/GB1116435A/en not_active Expired
- 1965-09-08 BE BE669347D patent/BE669347A/xx unknown
- 1965-09-09 ES ES0317635A patent/ES317635A1/en not_active Expired
- 1965-09-10 NL NL6511845A patent/NL6511845A/xx unknown
- 1965-12-06 FR FR41105A patent/FR7047M/fr not_active Expired
-
1967
- 1967-09-21 FR FR121826A patent/FR7008M/fr not_active Expired
- 1967-09-21 FR FR121825A patent/FR7048M/fr not_active Expired
- 1967-09-21 FR FR121824A patent/FR7007M/fr not_active Expired
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4163788A (en) | 1968-03-27 | 1979-08-07 | Ciba-Geigy Corporation | Tertiary aminoacids |
US4316850A (en) | 1968-03-27 | 1982-02-23 | Ciba-Geigy Corporation | Tertiary aminoacids |
JPS5033052B1 (en) * | 1968-10-25 | 1975-10-27 | ||
JPS5111613B1 (en) * | 1968-10-25 | 1976-04-13 | ||
JPS5111615B1 (en) * | 1968-10-25 | 1976-04-13 | ||
JPS5111614B1 (en) * | 1968-10-25 | 1976-04-13 | ||
JPS5111616B1 (en) * | 1968-10-25 | 1976-04-13 | ||
JPS5034556B1 (en) * | 1970-07-13 | 1975-11-10 |
Also Published As
Publication number | Publication date |
---|---|
NL6511845A (en) | 1966-03-11 |
ES317635A1 (en) | 1966-04-01 |
BR6572746D0 (en) | 1973-08-07 |
GB1116435A (en) | 1968-06-06 |
FR7008M (en) | 1969-06-02 |
BE669347A (en) | 1966-03-08 |
US3624142A (en) | 1971-11-30 |
FR1460659A (en) | 1966-01-07 |
IL24046A (en) | 1970-03-22 |
CH490309A (en) | 1970-05-15 |
FR7048M (en) | 1969-06-16 |
GB1116434A (en) | 1968-06-06 |
GB1116433A (en) | 1968-06-06 |
FR7047M (en) | 1969-06-16 |
FR7007M (en) | 1969-06-02 |
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