FR2503140A1 - Acides biphenyl-4 oxo-4 methylene-3 butyriques, leur procede de preparation et leur utilisation comme medicaments - Google Patents
Acides biphenyl-4 oxo-4 methylene-3 butyriques, leur procede de preparation et leur utilisation comme medicaments Download PDFInfo
- Publication number
- FR2503140A1 FR2503140A1 FR8106590A FR8106590A FR2503140A1 FR 2503140 A1 FR2503140 A1 FR 2503140A1 FR 8106590 A FR8106590 A FR 8106590A FR 8106590 A FR8106590 A FR 8106590A FR 2503140 A1 FR2503140 A1 FR 2503140A1
- Authority
- FR
- France
- Prior art keywords
- oxo
- methylene
- butyric acid
- treatment
- atherosclerosis
- 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
- 238000011282 treatment Methods 0.000 title claims abstract description 10
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 201000001320 Atherosclerosis Diseases 0.000 title claims abstract description 6
- -1 methylene butyric acid Chemical compound 0.000 title claims description 7
- 230000002265 prevention Effects 0.000 title description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract 2
- 239000011707 mineral Substances 0.000 claims abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000002547 new drug Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 229940126601 medicinal product Drugs 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229910052740 iodine Chemical group 0.000 description 4
- 239000011630 iodine Chemical group 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 231100000111 LD50 Toxicity 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000000871 hypocholesterolemic effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 208000037260 Atherosclerotic Plaque Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JBADCUBNRWNZQE-UHFFFAOYSA-N C=C(CC(O)=O)C(c1ccc(C(CC=C2)C=C2F)cc1)=O Chemical compound C=C(CC(O)=O)C(c1ccc(C(CC=C2)C=C2F)cc1)=O JBADCUBNRWNZQE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- SEVATKUPNNZNBC-UHFFFAOYSA-N O=CCCC(=O)O.C1(=CC=CC=C1)C1=CC=CC=C1 Chemical compound O=CCCC(=O)O.C1(=CC=CC=C1)C1=CC=CC=C1 SEVATKUPNNZNBC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 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
- 150000007513 acids Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Chemical group 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/88—Unsaturated compounds containing keto groups containing halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8106590A FR2503140A1 (fr) | 1981-03-31 | 1981-03-31 | Acides biphenyl-4 oxo-4 methylene-3 butyriques, leur procede de preparation et leur utilisation comme medicaments |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8106590A FR2503140A1 (fr) | 1981-03-31 | 1981-03-31 | Acides biphenyl-4 oxo-4 methylene-3 butyriques, leur procede de preparation et leur utilisation comme medicaments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2503140A1 true FR2503140A1 (fr) | 1982-10-08 |
| FR2503140B1 FR2503140B1 (enExample) | 1984-04-13 |
Family
ID=9256904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8106590A Granted FR2503140A1 (fr) | 1981-03-31 | 1981-03-31 | Acides biphenyl-4 oxo-4 methylene-3 butyriques, leur procede de preparation et leur utilisation comme medicaments |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2503140A1 (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996015096A1 (en) * | 1994-11-15 | 1996-05-23 | Bayer Corporation | Substituted 4-biarylbutyric or 5-biarylpentanoic acids and derivatives as matrix metalloprotease inhibitiors |
| WO1997017317A1 (en) * | 1995-11-03 | 1997-05-15 | Pharmacia & Upjohn S.P.A. | 4-phenyl-4-oxo-butanoic acid derivatives with kynurenine-3-hydroxylase inhibiting activity |
| US5886022A (en) * | 1995-06-05 | 1999-03-23 | Bayer Corporation | Substituted cycloalkanecarboxylic acid derivatives as matrix metalloprotease inhibitors |
| US6166082A (en) * | 1994-11-15 | 2000-12-26 | Bayer Corporation | Substituted 5-biarylpentanoic acids and derivatives as matrix metalloprotease inhibitors |
| CN107056628A (zh) * | 2017-03-21 | 2017-08-18 | 北京师范大学 | 芬布芬葡甲胺盐及其制备方法与应用 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2047806A1 (en) * | 1970-09-29 | 1972-04-06 | Dr Karl Thomae GmbH, 7950 Biberach | 3-aroyl-acrylic acids - pharmaceutical intermediates prepd from acetophenones and glyoxylic acid derivs |
| FR2265409A1 (en) * | 1974-03-25 | 1975-10-24 | Fabre Sa Pierre | 4-Oxo-4-phenyl-2-methyl(ene)-butyric acid derivs. - analgesics, antiinflammatories and hypocholesterolemiants |
| FR2300551A2 (fr) * | 1975-02-17 | 1976-09-10 | Fabre Sa Pierre | Nouveaux |
-
1981
- 1981-03-31 FR FR8106590A patent/FR2503140A1/fr active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2047806A1 (en) * | 1970-09-29 | 1972-04-06 | Dr Karl Thomae GmbH, 7950 Biberach | 3-aroyl-acrylic acids - pharmaceutical intermediates prepd from acetophenones and glyoxylic acid derivs |
| FR2265409A1 (en) * | 1974-03-25 | 1975-10-24 | Fabre Sa Pierre | 4-Oxo-4-phenyl-2-methyl(ene)-butyric acid derivs. - analgesics, antiinflammatories and hypocholesterolemiants |
| FR2300551A2 (fr) * | 1975-02-17 | 1976-09-10 | Fabre Sa Pierre | Nouveaux |
Non-Patent Citations (1)
| Title |
|---|
| EXBK/80 * |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996015096A1 (en) * | 1994-11-15 | 1996-05-23 | Bayer Corporation | Substituted 4-biarylbutyric or 5-biarylpentanoic acids and derivatives as matrix metalloprotease inhibitiors |
| US5854277A (en) * | 1994-11-15 | 1998-12-29 | Bayer Corporation | Thiophenebutanoic acid derivatives as matrix metalloprotease inhibitors |
| US5859047A (en) * | 1994-11-15 | 1999-01-12 | Bayer Corporation | Substituted 4-biarylbutyric acid derivatives as matrix metalloprotease inhibitors |
| US5861428A (en) * | 1994-11-15 | 1999-01-19 | Bayer Corporation | Substituted 4-biarylbutyric acid derivatives as matrix metalloprotease inhibitors |
| US5861427A (en) * | 1994-11-15 | 1999-01-19 | Kluender; Harold Clinton Eugene | Substituted 4-biarylbutyric acid derivatives as matrix metalloprotease inhibitors |
| US5874473A (en) * | 1994-11-15 | 1999-02-23 | Bayer Corporation | Substituted cycloalkanecarboxylic acid derivatives as matrix metalloprotease inhibitors |
| US5886043A (en) * | 1994-11-15 | 1999-03-23 | Bayer Corporation | Substituted 4-biarylbutyric acid derivatives as matrix metalloprotease inhibitors |
| US5886024A (en) * | 1994-11-15 | 1999-03-23 | Bayer Corporation | Thiophene-containing butonic acid derivatives as matrix metalloprotease inhibitors |
| US6166082A (en) * | 1994-11-15 | 2000-12-26 | Bayer Corporation | Substituted 5-biarylpentanoic acids and derivatives as matrix metalloprotease inhibitors |
| US5886022A (en) * | 1995-06-05 | 1999-03-23 | Bayer Corporation | Substituted cycloalkanecarboxylic acid derivatives as matrix metalloprotease inhibitors |
| WO1997017317A1 (en) * | 1995-11-03 | 1997-05-15 | Pharmacia & Upjohn S.P.A. | 4-phenyl-4-oxo-butanoic acid derivatives with kynurenine-3-hydroxylase inhibiting activity |
| CN107056628A (zh) * | 2017-03-21 | 2017-08-18 | 北京师范大学 | 芬布芬葡甲胺盐及其制备方法与应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2503140B1 (enExample) | 1984-04-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |