CA1108159A - Substituted 4-(((2-thienyl)methyl)amino) benzoic acids and a method for treating hypolipidemia - Google Patents
Substituted 4-(((2-thienyl)methyl)amino) benzoic acids and a method for treating hypolipidemiaInfo
- Publication number
- CA1108159A CA1108159A CA300,577A CA300577A CA1108159A CA 1108159 A CA1108159 A CA 1108159A CA 300577 A CA300577 A CA 300577A CA 1108159 A CA1108159 A CA 1108159A
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- benzoic acid
- compounds
- amino
- preparing
- 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
- 238000000034 method Methods 0.000 title claims description 16
- SHTQXYWTNXSOLW-UHFFFAOYSA-N 4-(thiophen-2-ylmethylamino)benzoic acid Chemical class C1=CC(C(=O)O)=CC=C1NCC1=CC=CS1 SHTQXYWTNXSOLW-UHFFFAOYSA-N 0.000 title abstract description 4
- 206010021024 Hypolipidaemia Diseases 0.000 title 1
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N aniline-p-carboxylic acid Natural products NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 19
- 239000002262 Schiff base Substances 0.000 claims description 11
- 150000004753 Schiff bases Chemical class 0.000 claims description 11
- -1 4-(2-thienylmethyl-amino)benzoic acid compound Chemical class 0.000 claims description 9
- 229960004050 aminobenzoic acid Drugs 0.000 claims description 8
- VWYFITBWBRVBSW-UHFFFAOYSA-N 5-chlorothiophene-2-carbaldehyde Chemical compound ClC1=CC=C(C=O)S1 VWYFITBWBRVBSW-UHFFFAOYSA-N 0.000 claims description 6
- PARLXHWQUIUPSZ-UHFFFAOYSA-N ethyl 4-[(5-chlorothiophen-2-yl)methylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NCC1=CC=C(Cl)S1 PARLXHWQUIUPSZ-UHFFFAOYSA-N 0.000 claims description 6
- UTIRHZZQPMLIFQ-UHFFFAOYSA-N 4,5-dichlorothiophene-2-carbaldehyde Chemical compound ClC=1C=C(C=O)SC=1Cl UTIRHZZQPMLIFQ-UHFFFAOYSA-N 0.000 claims description 5
- BNBORUHHZQDZTR-UHFFFAOYSA-N 4-[(4,5-dichlorothiophen-2-yl)methylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NCC1=CC(Cl)=C(Cl)S1 BNBORUHHZQDZTR-UHFFFAOYSA-N 0.000 claims description 5
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 claims description 3
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 claims description 3
- YYEIZVYJDLYMIH-UHFFFAOYSA-N 4-chlorothiophene-2-carbaldehyde Chemical compound ClC1=CSC(C=O)=C1 YYEIZVYJDLYMIH-UHFFFAOYSA-N 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- ASXSKEDEMPIBEU-UHFFFAOYSA-N 4-[(3,5-dichlorothiophen-2-yl)methylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NCC1=C(Cl)C=C(Cl)S1 ASXSKEDEMPIBEU-UHFFFAOYSA-N 0.000 claims 1
- GFBVUFQNHLUCPX-UHFFFAOYSA-N 5-bromothiophene-2-carbaldehyde Chemical compound BrC1=CC=C(C=O)S1 GFBVUFQNHLUCPX-UHFFFAOYSA-N 0.000 claims 1
- IWGWGFWJAMDYOQ-UHFFFAOYSA-N BrC1=CC=C(S1)N(C1=CC=C(C(=O)O)C=C1)C Chemical compound BrC1=CC=C(S1)N(C1=CC=C(C(=O)O)C=C1)C IWGWGFWJAMDYOQ-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 30
- 239000000203 mixture Substances 0.000 abstract description 22
- 210000002966 serum Anatomy 0.000 abstract description 7
- 150000003839 salts Chemical class 0.000 abstract description 6
- 150000002632 lipids Chemical class 0.000 abstract description 5
- 241000124008 Mammalia Species 0.000 abstract description 4
- 230000000055 hyoplipidemic effect Effects 0.000 abstract description 4
- 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 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 230000000875 corresponding effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- ALSNEOBUYJFMCQ-UHFFFAOYSA-N 4-[(4-chlorothiophen-2-yl)methylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NCC1=CC(Cl)=CS1 ALSNEOBUYJFMCQ-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 150000003626 triacylglycerols Chemical class 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000460 chlorine Chemical group 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
- 230000037213 diet Effects 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229940063656 aluminum chloride Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
- 239000001095 magnesium carbonate Substances 0.000 description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000000050 nutritive effect Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000013589 supplement Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- DKFYWJTYSGADHK-UHFFFAOYSA-N 2-(bromomethyl)-3,5-dichlorothiophene Chemical compound ClC1=CC(Cl)=C(CBr)S1 DKFYWJTYSGADHK-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical group NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- OWGFXJXHVGPRTO-UHFFFAOYSA-N 4-[(5-bromothiophen-2-yl)methylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NCC1=CC=C(Br)S1 OWGFXJXHVGPRTO-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
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- 229920002261 Corn starch Polymers 0.000 description 1
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- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- AUEBUHLSRCZJPY-UHFFFAOYSA-N S1C(=CC=C1)N(C1=CC=C(C(=O)O)C=C1)C Chemical class S1C(=CC=C1)N(C1=CC=C(C(=O)O)C=C1)C AUEBUHLSRCZJPY-UHFFFAOYSA-N 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
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- 239000004147 Sorbitan trioleate Substances 0.000 description 1
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
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- 150000004781 alginic acids Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- JGDITNMASUZKPW-UHFFFAOYSA-K aluminium trichloride hexahydrate Chemical compound O.O.O.O.O.O.Cl[Al](Cl)Cl JGDITNMASUZKPW-UHFFFAOYSA-K 0.000 description 1
- 229940009861 aluminum chloride hexahydrate Drugs 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
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- 235000014121 butter Nutrition 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
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- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
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- QHYQXLZAPVFNKW-UHFFFAOYSA-N ethyl 4-[(2,2,2-trifluoroacetyl)amino]benzoate Chemical compound CCOC(=O)C1=CC=C(NC(=O)C(F)(F)F)C=C1 QHYQXLZAPVFNKW-UHFFFAOYSA-N 0.000 description 1
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- 150000003141 primary amines Chemical class 0.000 description 1
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- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
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- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/28—Halogen atoms
-
- 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
- A61P3/06—Antihyperlipidemics
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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78546777A | 1977-04-07 | 1977-04-07 | |
| US785,467 | 1991-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1108159A true CA1108159A (en) | 1981-09-01 |
Family
ID=25135597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA300,577A Expired CA1108159A (en) | 1977-04-07 | 1978-04-06 | Substituted 4-(((2-thienyl)methyl)amino) benzoic acids and a method for treating hypolipidemia |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS53149968A (en, 2012) |
| BE (1) | BE865809A (en, 2012) |
| CA (1) | CA1108159A (en, 2012) |
| CH (1) | CH629796A5 (en, 2012) |
| DE (1) | DE2814798A1 (en, 2012) |
| DK (1) | DK153403C (en, 2012) |
| FR (1) | FR2386542A1 (en, 2012) |
| GB (1) | GB1565936A (en, 2012) |
| IE (1) | IE46713B1 (en, 2012) |
| IT (1) | IT1094318B (en, 2012) |
| NL (1) | NL7803669A (en, 2012) |
| NO (1) | NO149241C (en, 2012) |
| NZ (1) | NZ186886A (en, 2012) |
| SE (1) | SE446734B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4143151A (en) * | 1978-07-03 | 1979-03-06 | The Dow Chemical Company | Method for treating hyperglycemia in mammals using arylamino benzoic acids |
| JPS6421196A (en) * | 1987-07-15 | 1989-01-24 | Nippon Concrete Ind Co Ltd | Auger screw |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2983729A (en) * | 1958-04-30 | 1961-05-09 | Monsanto Chemicals | Preparation of 5-halothienyl amines |
| US3859440A (en) * | 1971-10-08 | 1975-01-07 | Ici Australia Ltd | Certain thienyl compounds used to control acarina |
| US4185115A (en) * | 1975-03-12 | 1980-01-22 | American Cyanamid Company | Antilipidemic para-[aryl(alkyl or alkenyl)amino]-benzoic acid derivatives |
-
1978
- 1978-04-03 CH CH355178A patent/CH629796A5/fr not_active IP Right Cessation
- 1978-04-04 IT IT21941/78A patent/IT1094318B/it active
- 1978-04-05 NZ NZ186886A patent/NZ186886A/xx unknown
- 1978-04-05 DE DE19782814798 patent/DE2814798A1/de active Granted
- 1978-04-05 IE IE678/78A patent/IE46713B1/en not_active IP Right Cessation
- 1978-04-05 FR FR7810111A patent/FR2386542A1/fr active Granted
- 1978-04-06 GB GB13449/78A patent/GB1565936A/en not_active Expired
- 1978-04-06 SE SE7803910A patent/SE446734B/sv not_active IP Right Cessation
- 1978-04-06 CA CA300,577A patent/CA1108159A/en not_active Expired
- 1978-04-06 NL NL7803669A patent/NL7803669A/xx not_active Application Discontinuation
- 1978-04-06 NO NO781214A patent/NO149241C/no unknown
- 1978-04-06 DK DK153178A patent/DK153403C/da not_active IP Right Cessation
- 1978-04-06 JP JP4075978A patent/JPS53149968A/ja active Granted
- 1978-04-07 BE BE186657A patent/BE865809A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IE46713B1 (en) | 1983-09-07 |
| NL7803669A (nl) | 1978-10-10 |
| NO149241B (no) | 1983-12-05 |
| NZ186886A (en) | 1980-02-21 |
| IE780678L (en) | 1978-10-07 |
| FR2386542B1 (en, 2012) | 1981-07-10 |
| SE7803910L (sv) | 1978-10-08 |
| NO149241C (no) | 1984-03-14 |
| DK153403B (da) | 1988-07-11 |
| DK153403C (da) | 1988-11-28 |
| IT1094318B (it) | 1985-07-26 |
| NO781214L (no) | 1978-10-10 |
| DE2814798A1 (de) | 1978-10-19 |
| IT7821941A0 (it) | 1978-04-04 |
| JPS53149968A (en) | 1978-12-27 |
| DK153178A (da) | 1978-10-08 |
| SE446734B (sv) | 1986-10-06 |
| CH629796A5 (en) | 1982-05-14 |
| FR2386542A1 (fr) | 1978-11-03 |
| BE865809A (fr) | 1978-10-09 |
| JPS6126790B2 (en, 2012) | 1986-06-21 |
| DE2814798C2 (en, 2012) | 1988-05-26 |
| GB1565936A (en) | 1980-04-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |