CA1077957A - Hypolipidemic 4-(monoalkylamino) benzoic acid derivatives - Google Patents

Hypolipidemic 4-(monoalkylamino) benzoic acid derivatives

Info

Publication number: CA1077957A
Authority: CA; Canada
Prior art keywords: compound; formula; benzoic acid; ethyl; hydrogen
Prior art date: 1973-10-01
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

Application number

CA210,303A

Other languages

English (en)

French (fr)

Other versions

CA210303S (en

Inventor

Jay D. Albright

Stephen J. Riggi

Robert G. Shepherd

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid Co

Priority date (The priority date 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 date listed.)

1973-10-01

Filing date

1974-09-30

Publication date

1980-05-20

1974-09-30 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1980-05-20 Application granted granted Critical

1980-05-20 Publication of CA1077957A publication Critical patent/CA1077957A/en

Status Expired legal-status Critical Current

Links

230000000055 hyoplipidemic effect Effects 0.000 title description 11
150000001558 benzoic acid derivatives Chemical class 0.000 title description 7
150000003839 salts Chemical class 0.000 claims abstract description 24
235000010233 benzoic acid Nutrition 0.000 claims abstract description 10
150000001875 compounds Chemical class 0.000 claims description 60
BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 claims description 42
-1 aryl sulfonate ester Chemical group 0.000 claims description 34
125000000217 alkyl group Chemical group 0.000 claims description 33
239000000047 product Substances 0.000 claims description 31
238000000034 method Methods 0.000 claims description 30
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 29
239000002253 acid Substances 0.000 claims description 26
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 17
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
QXWKHSSBFQDQPR-UHFFFAOYSA-N 4-(hexadecylamino)benzoic acid Chemical compound CCCCCCCCCCCCCCCCNC1=CC=C(C(O)=O)C=C1 QXWKHSSBFQDQPR-UHFFFAOYSA-N 0.000 claims description 15
150000007513 acids Chemical class 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 12
230000007062 hydrolysis Effects 0.000 claims description 12
238000006460 hydrolysis reaction Methods 0.000 claims description 12
239000002585 base Substances 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
229910052783 alkali metal Inorganic materials 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 8
239000005711 Benzoic acid Substances 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
239000003513 alkali Substances 0.000 claims description 6
150000002367 halogens Chemical group 0.000 claims description 6
150000002431 hydrogen Chemical group 0.000 claims description 6
OCHHYNXJGSPCKN-UHFFFAOYSA-N 4-(pentadecylamino)benzoic acid Chemical compound CCCCCCCCCCCCCCCNC1=CC=C(C(O)=O)C=C1 OCHHYNXJGSPCKN-UHFFFAOYSA-N 0.000 claims description 5
150000008052 alkyl sulfonates Chemical group 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
230000009467 reduction Effects 0.000 claims description 5
238000006722 reduction reaction Methods 0.000 claims description 5
HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 claims description 4
NPFIXBKVMRANIW-UHFFFAOYSA-N 4-(heptadecylamino)benzoic acid Chemical compound CCCCCCCCCCCCCCCCCNC1=CC=C(C(O)=O)C=C1 NPFIXBKVMRANIW-UHFFFAOYSA-N 0.000 claims description 4
230000001476 alcoholic effect Effects 0.000 claims description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 4
NIOYUNMRJMEDGI-UHFFFAOYSA-N hexadecanal Chemical compound CCCCCCCCCCCCCCCC=O NIOYUNMRJMEDGI-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
JERBHTIKPOTHFN-UHFFFAOYSA-N 4-(tetradecylamino)benzoic acid Chemical compound CCCCCCCCCCCCCCNC1=CC=C(C(O)=O)C=C1 JERBHTIKPOTHFN-UHFFFAOYSA-N 0.000 claims description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 3
159000000000 sodium salts Chemical class 0.000 claims description 3
229910000564 Raney nickel Inorganic materials 0.000 claims description 2
125000004442 acylamino group Chemical group 0.000 claims description 2
239000000460 chlorine Chemical group 0.000 claims description 2
125000000524 functional group Chemical group 0.000 claims description 2
230000003647 oxidation Effects 0.000 claims description 2
238000007254 oxidation reaction Methods 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 7
IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims 5
125000004093 cyano group Chemical group *C#N 0.000 claims 3
230000003301 hydrolyzing effect Effects 0.000 claims 3
125000002252 acyl group Chemical group 0.000 claims 2
239000003638 chemical reducing agent Substances 0.000 claims 2
HHSDZLLPIXMEIU-UHFFFAOYSA-N 1-bromoheptadecane Chemical compound CCCCCCCCCCCCCCCCCBr HHSDZLLPIXMEIU-UHFFFAOYSA-N 0.000 claims 1
JKOTZBXSNOGCIF-UHFFFAOYSA-N 1-bromopentadecane Chemical compound CCCCCCCCCCCCCCCBr JKOTZBXSNOGCIF-UHFFFAOYSA-N 0.000 claims 1
KOFZTCSTGIWCQG-UHFFFAOYSA-N 1-bromotetradecane Chemical compound CCCCCCCCCCCCCCBr KOFZTCSTGIWCQG-UHFFFAOYSA-N 0.000 claims 1
YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 claims 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
125000003282 alkyl amino group Chemical group 0.000 claims 1
125000005228 aryl sulfonate group Chemical group 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Chemical group 0.000 claims 1
238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
238000006555 catalytic reaction Methods 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
229910052731 fluorine Inorganic materials 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 claims 1
239000011780 sodium chloride Substances 0.000 claims 1
150000002148 esters Chemical class 0.000 abstract description 19
210000002966 serum Anatomy 0.000 abstract description 15
150000002632 lipids Chemical class 0.000 abstract description 9
150000001559 benzoic acids Chemical class 0.000 abstract description 5
241000124008 Mammalia Species 0.000 abstract description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 110
239000000203 mixture Substances 0.000 description 64
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 51
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
239000007787 solid Substances 0.000 description 23
239000013078 crystal Substances 0.000 description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
229940050390 benzoate Drugs 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
229960000443 hydrochloric acid Drugs 0.000 description 12
235000011167 hydrochloric acid Nutrition 0.000 description 12
229910000027 potassium carbonate Inorganic materials 0.000 description 12
229940093956 potassium carbonate Drugs 0.000 description 12
235000011181 potassium carbonates Nutrition 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
238000001953 recrystallisation Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 9
239000003826 tablet Substances 0.000 description 9
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 8
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
229930182558 Sterol Natural products 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
150000003432 sterols Chemical class 0.000 description 8
235000003702 sterols Nutrition 0.000 description 8
239000002775 capsule Substances 0.000 description 7
VCFLGAOCYOZUMD-UHFFFAOYSA-N ethyl 4-(hexadecylamino)benzoate Chemical compound CCCCCCCCCCCCCCCCNC1=CC=C(C(=O)OCC)C=C1 VCFLGAOCYOZUMD-UHFFFAOYSA-N 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
150000001350 alkyl halides Chemical class 0.000 description 6
150000003904 phospholipids Chemical class 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 6
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
238000005917 acylation reaction Methods 0.000 description 5
229940076134 benzene Drugs 0.000 description 5
235000005911 diet Nutrition 0.000 description 5
230000037213 diet Effects 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
238000009472 formulation Methods 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
XJPFHIYOQHZAOW-UHFFFAOYSA-N 4-(dodecylamino)benzoic acid Chemical compound CCCCCCCCCCCCNC1=CC=C(C(O)=O)C=C1 XJPFHIYOQHZAOW-UHFFFAOYSA-N 0.000 description 4
229920002261 Corn starch Polymers 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
230000010933 acylation Effects 0.000 description 4
229940100198 alkylating agent Drugs 0.000 description 4
239000002168 alkylating agent Substances 0.000 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 4
239000008120 corn starch Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
239000000463 material Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241000699694 Gerbillinae Species 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
239000012346 acetyl chloride Substances 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
WVHBHPATSLQXGC-UHFFFAOYSA-N benzene;ethanol Chemical compound CCO.C1=CC=CC=C1 WVHBHPATSLQXGC-UHFFFAOYSA-N 0.000 description 3
CMDKPGRTAQVGFQ-RMKNXTFCSA-N cinoxate Chemical compound CCOCCOC(=O)\C=C\C1=CC=C(OC)C=C1 CMDKPGRTAQVGFQ-RMKNXTFCSA-N 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
VGCWDPSEZSPOQV-UHFFFAOYSA-N ethyl 3-(hexadecylamino)benzoate Chemical compound CCCCCCCCCCCCCCCCNC1=CC=CC(C(=O)OCC)=C1 VGCWDPSEZSPOQV-UHFFFAOYSA-N 0.000 description 3
FRUOAAOGFLFXMB-UHFFFAOYSA-N ethyl 4-(heptadecylamino)benzoate Chemical compound CCCCCCCCCCCCCCCCCNC1=CC=C(C(=O)OCC)C=C1 FRUOAAOGFLFXMB-UHFFFAOYSA-N 0.000 description 3
DGGGBDLOUZPPQJ-UHFFFAOYSA-N ethyl 4-(tetradecylamino)benzoate Chemical compound CCCCCCCCCCCCCCNC1=CC=C(C(=O)OCC)C=C1 DGGGBDLOUZPPQJ-UHFFFAOYSA-N 0.000 description 3
MPKWKBNGMMLYKV-UHFFFAOYSA-N ethyl 4-(tridecylamino)benzoate Chemical compound CCCCCCCCCCCCCNC1=CC=C(C(=O)OCC)C=C1 MPKWKBNGMMLYKV-UHFFFAOYSA-N 0.000 description 3
125000004494 ethyl ester group Chemical group 0.000 description 3
238000001914 filtration Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 2
FDIAQFIWISNAQO-UHFFFAOYSA-N 4-(nonadecylamino)benzoic acid Chemical compound CCCCCCCCCCCCCCCCCCCNC1=CC=C(C(O)=O)C=C1 FDIAQFIWISNAQO-UHFFFAOYSA-N 0.000 description 2
GEISIMATOLPHFV-UHFFFAOYSA-N 4-(octadecylamino)benzoic acid Chemical compound CCCCCCCCCCCCCCCCCCNC1=CC=C(C(O)=O)C=C1 GEISIMATOLPHFV-UHFFFAOYSA-N 0.000 description 2
UOPFJBGJNMUVAW-UHFFFAOYSA-N 4-(octylamino)benzoic acid Chemical compound CCCCCCCCNC1=CC=C(C(O)=O)C=C1 UOPFJBGJNMUVAW-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
229940086681 4-aminobenzoate Drugs 0.000 description 2
201000001320 Atherosclerosis Diseases 0.000 description 2
241000167854 Bourreria succulenta Species 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
125000003047 N-acetyl group Chemical group 0.000 description 2
241000700159 Rattus Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
229960004050 aminobenzoic acid Drugs 0.000 description 2
230000003444 anaesthetic effect Effects 0.000 description 2
239000003524 antilipemic agent Substances 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
230000036765 blood level Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
235000019693 cherries Nutrition 0.000 description 2
239000007958 cherry flavor Substances 0.000 description 2
235000012000 cholesterol Nutrition 0.000 description 2
229940107161 cholesterol Drugs 0.000 description 2
KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 2
229960001214 clofibrate Drugs 0.000 description 2
238000001816 cooling Methods 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
229940008406 diethyl sulfate Drugs 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
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125000005490 tosylate group Chemical group 0.000 description 1
ZMCBYSBVJIMENC-UHFFFAOYSA-N tricaine Chemical compound CCOC(=O)C1=CC=CC(N)=C1 ZMCBYSBVJIMENC-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
QDNCLIPKBNMUPP-UHFFFAOYSA-N trimethyloxidanium Chemical compound C[O+](C)C QDNCLIPKBNMUPP-UHFFFAOYSA-N 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229940074411 xylene Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/60—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in meta- or para- positions
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- 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

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pyridine Compounds (AREA)

CA210,303A 1973-10-01 1974-09-30 Hypolipidemic 4-(monoalkylamino) benzoic acid derivatives Expired CA1077957A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US402212A US3868416A (en)	1973-10-01	1973-10-01	Hypolipidemic 4-(monoalkylamino)benzoic acid derivatives

Publications (1)

Publication Number	Publication Date
CA1077957A true CA1077957A (en)	1980-05-20

Family

ID=23590998

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA210,303A Expired CA1077957A (en)	1973-10-01	1974-09-30	Hypolipidemic 4-(monoalkylamino) benzoic acid derivatives

Country Status (22)

Country	Link
US (2)	US3868416A (da)
JP (1)	JPS5747901B2 (da)
AR (1)	AR211687A1 (da)
AT (1)	AT338250B (da)
BE (1)	BE820542A (da)
CA (1)	CA1077957A (da)
CH (1)	CH609676A5 (da)
DD (1)	DD116031A5 (da)
DE (1)	DE2446010C2 (da)
DK (1)	DK141844B (da)
ES (1)	ES430574A1 (da)
FR (1)	FR2246267B1 (da)
GB (1)	GB1488674A (da)
GT (1)	GT197851174A (da)
HU (1)	HU175875B (da)
IE (1)	IE40527B1 (da)
IL (1)	IL45643A (da)
NL (1)	NL179725C (da)
SE (1)	SE410595B (da)
SU (1)	SU590311A1 (da)
YU (1)	YU262274A (da)
ZA (1)	ZA745732B (da)

Families Citing this family (45)

* Cited by examiner, † Cited by third party
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GB1471431A (en) *	1974-04-30	1977-04-27	Science Union & Cie	Alkanolamine derivatives processes for their preparation and pharmaceutical compositions containing them
US4185115A (en) *	1975-03-12	1980-01-22	American Cyanamid Company	Antilipidemic para-[aryl(alkyl or alkenyl)amino]-benzoic acid derivatives
US4350822A (en) *	1975-03-12	1982-09-21	American Cyanamid Company	Antilipidemicpara-[aryl(alkyl or alkenyl)amino]benzoic acid derivatives
US4058550A (en) *	1975-10-28	1977-11-15	American Cyanamid Company	Polysubstituted-alkyl esters of 4-alkylaminobenzoic acids
US4182776A (en) *	1975-12-09	1980-01-08	American Cyanamid Company	Method of treating lipidemia with aryloxyalkylaminobenzoic acids and esters
AU500881B2 (en) *	1976-01-19	1979-06-07	Dow Chemical Company, The	Hypolipidemic p-aminobenzoic acids
GB1576007A (en) *	1976-02-11	1980-10-01	Beecham Group Ltd	Hypolipidaemic compositions
US4105791A (en) *	1976-03-22	1978-08-08	The Dow Chemical Company	Hypolipidemic cycloalkylaminobenzoic acids
US4133890A (en) *	1977-01-05	1979-01-09	The Dow Chemical Company	Hypolipidemic compositions and method employing derivatives of 4-(((1,3-benzodioxol-5-yl)methyl)amino)benzoic acid
US4117158A (en) *	1977-09-27	1978-09-26	American Cyanamid Company	4-(monoalkylamino)benzonitriles useful as anti-atherosclerotic agents
US4245120A (en) *	1977-09-27	1981-01-13	American Cyanamid Company	4-(Monoalkylamino)benzene polycarboxylic acids
US4245119A (en) *	1977-09-27	1981-01-13	American Cyanamid Company	4-(Monoalkylamino) benzene polycarboxylic acids
US4348399A (en) *	1978-02-02	1982-09-07	American Cyanamid Company	Antiatherosclerotic and hypolipidemic 4-(monoalkylamino)phenyl alkane, alkene and alkyne carbinols, aldehydes, carboxylic acids and derivatives
US4154756A (en) *	1977-12-15	1979-05-15	American Cyanamid Company	2-Substituted-4'-(monoalkylamino)-acetophenones
US4136256A (en) *	1977-09-27	1979-01-23	American Cyanamid Company	4-(monoalkylamino)benzoic acid imidates
US4242273A (en) *	1977-09-27	1980-12-30	American Cyanamid Company	4-(Monoalkylamino)benzoic acid amides and imidates
US4272546A (en) *	1977-12-19	1981-06-09	American Cyanamid Company	Esters of 4-(monoalkylamino)benzoic hydroxyalkanoic acids
US4254138A (en) *	1977-12-19	1981-03-03	American Cyanamid Company	Esters of 4-(monoalkylamino)benzoic hydroxyalkanoic acids
US4230878A (en) *	1978-03-08	1980-10-28	American Cyanamid Company	Hypolipidemic and antiatherosclerotic 4-[(cyclopropyl alkyl)amino]benzoic acids and derivatives
IL56517A0 (en) *	1978-02-02	1979-03-12	American Cyanamid Co	Novel 4-(cycloalkyl or cyclalkenyl substituted) amino, alkylamino or alkenylamino benzoic acids, salts and derivatives
US4230628A (en) *	1978-04-12	1980-10-28	American Cyanamid Company	4-[(Carboxyl- and sulfamyl-substituted alkyl)-amino] benzoic acids and analogs
US4243609A (en) *	1978-02-02	1981-01-06	American Cyanamid Company	Ring-fluorinated 4-(hexadecyl-amino) N-substituted benzamide compounds
US4333940A (en) *	1978-02-02	1982-06-08	American Cyanamid Company	Ring-fluorinated 4-(monosubstituted-amino) phenyl compounds in inhibiting atherosclerotic lesion development
US4205085A (en) *	1978-03-09	1980-05-27	American Cyanamid Company	Hypolipidemic and antiatherosclerotic 4-(polyfluoroalkylamino)phenyl compounds
US4245097A (en) *	1978-02-27	1981-01-13	American Cyanamid Company	4-[(Monosubstituted-alkyl) amino] benzoic acids and analogs as hypolipidemic and antiatherosclerotic agents
US4311846A (en) *	1978-02-27	1982-01-19	American Cyanamid Company	4-[(Monosubstituted-alkyl) amino]benzoic acids and analogs as hypolipidemic and antiatherosclerotic agents
US4178385A (en) *	1978-03-03	1979-12-11	The Dow Chemical Company	Method for treating hyperlipidemia in primates using 4-((4-fluorophenylmethyl)amino)benzoic acid
US4305959A (en) *	1978-03-09	1981-12-15	American Cyanamid Company	Hypolipidemic and antiatherosclerotic 4-(polyfluoro-alkylamino)phenyl compounds
US4310545A (en) *	1978-03-09	1982-01-12	American Cyanamid Company	Hypolipidemic and antiatherosclerotic 4-(polyfluoroalkylamino) phenyl compounds
US4318914A (en) *	1978-03-09	1982-03-09	American Cyanamid Company	Hypolipidemic and antiatherosclerotic 4-(polyfluoro-alkylamino)phenyl compounds
US4307113A (en) *	1978-04-20	1981-12-22	Sandoz, Inc.	Anthranilic acid derivatives
US4181737A (en) *	1978-05-18	1980-01-01	The Dow Chemical Company	4-((3-Methoxyphenyl)amino)benzoic acid, a method for treating hyperlipidemia, and compositions thereof
US4206223A (en) *	1979-01-05	1980-06-03	The Dow Chemical Company	Method for treating hyperglycemia in mammals using 4-(((1,3-benzodioxol-5-yl)methyl)amino)benzoic acid or derivatives thereof
US4281019A (en) *	1979-02-01	1981-07-28	American Cyanamid Company	4-[(Unsaturated or cyclopropylated alkyl)amino]phenyl compounds useful as hypolipidemic and antiatherosclerotic agents
YU57979A (en) *	1979-03-09	1982-10-31	Lek Tovarna Farmacevtskih	Process for preparing 4-9n-hexadecylamino0-benzoic acid
US4263320A (en) *	1979-06-04	1981-04-21	The Dow Chemical Company	Hypoglycemic phenylpropynylamino benzoic acids
US4311694A (en) *	1979-12-31	1982-01-19	American Cyanamid Company	Amorphous coprecipitates of 4-(monoalkylamino) benzoic acid and derivatives and certain water-soluble materials
US4375478A (en) *	1982-03-02	1983-03-01	Abbott Laboratories	Aminobenzoic acid derivatives
JP2659488B2 (ja) *	1992-01-22	1997-09-30	川崎重工業株式会社	引戸装置
US6746691B2 (en)	1993-09-20	2004-06-08	Kos Pharmaceuticals, Inc.	Intermediate release nicotinic acid compositions for treating hyperlipidemia having unique biopharmaceutical characteristics
US6129930A (en) *	1993-09-20	2000-10-10	Bova; David J.	Methods and sustained release nicotinic acid compositions for treating hyperlipidemia at night
US20080045573A1 (en) *	1993-09-20	2008-02-21	Bova David J	Methods and Sustained Release Nicotinic Acid Compositions for Treating Hyperlipidemia
US6818229B1 (en)	1993-09-20	2004-11-16	Kos Pharmaceuticals, Inc.	Intermediate release nicotinic acid compositions for treating hyperlipidemia
US6080428A (en) *	1993-09-20	2000-06-27	Bova; David J.	Nicotinic acid compositions for treating hyperlipidemia and related methods therefor
US6676967B1 (en)	1993-09-20	2004-01-13	Kos Pharmaceuticals, Inc.	Methods for reducing flushing in individuals being treated with nicotinic acid for hyperlipidemia

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3758561A (en) *	1968-10-18	1973-09-11	Merck & Co Inc	2-loweralkylamino-4-amino benzoic acids, their salts and esters, and acid addition salts thereof
US3716644A (en) *	1971-07-15	1973-02-13	American Cyanamid Co	Hypolipidemic agents

1973
- 1973-10-01 US US402212A patent/US3868416A/en not_active Expired - Lifetime
1974
- 1974-09-09 ZA ZA00745732A patent/ZA745732B/xx unknown
- 1974-09-11 IL IL45643A patent/IL45643A/xx unknown
- 1974-09-17 GB GB40539/74A patent/GB1488674A/en not_active Expired
- 1974-09-23 AR AR255678A patent/AR211687A1/es active
- 1974-09-26 DE DE2446010A patent/DE2446010C2/de not_active Expired
- 1974-09-27 YU YU02622/74A patent/YU262274A/xx unknown
- 1974-09-27 IE IE2015/74A patent/IE40527B1/xx unknown
- 1974-09-30 SE SE7412307A patent/SE410595B/xx not_active IP Right Cessation
- 1974-09-30 DK DK515474AA patent/DK141844B/da not_active IP Right Cessation
- 1974-09-30 CA CA210,303A patent/CA1077957A/en not_active Expired
- 1974-09-30 FR FR7432894A patent/FR2246267B1/fr not_active Expired
- 1974-09-30 BE BE149073A patent/BE820542A/xx not_active IP Right Cessation
- 1974-10-01 DD DD181444A patent/DD116031A5/xx unknown
- 1974-10-01 AT AT788574A patent/AT338250B/de not_active IP Right Cessation
- 1974-10-01 CH CH1321774A patent/CH609676A5/xx not_active IP Right Cessation
- 1974-10-01 NL NLAANVRAGE7412956,A patent/NL179725C/xx not_active IP Right Cessation
- 1974-10-01 HU HU74AE427A patent/HU175875B/hu unknown
- 1974-10-01 SU SU742065154A patent/SU590311A1/ru active
- 1974-10-01 JP JP49113271A patent/JPS5747901B2/ja not_active Expired
- 1974-10-02 ES ES430574A patent/ES430574A1/es not_active Expired
- 1974-10-25 US US518022A patent/US3924001A/en not_active Expired - Lifetime
1978
- 1978-03-01 GT GT197851174A patent/GT197851174A/es unknown

Also Published As

Publication number	Publication date
US3868416A (en)	1975-02-25
US3924001A (en)	1975-12-02
IE40527L (en)	1975-04-01
HU175875B (en)	1980-11-28
DK515474A (da)	1975-06-09
FR2246267B1 (da)	1977-10-28
AR211687A1 (es)	1978-02-28
ES430574A1 (es)	1977-02-16
NL179725B (nl)	1986-06-02
CH609676A5 (da)	1979-03-15
DK141844C (da)	1980-11-10
BE820542A (fr)	1975-04-01
JPS5747901B2 (da)	1982-10-13
NL7412956A (nl)	1975-04-03
ZA745732B (en)	1975-09-24
SU590311A1 (ru)	1978-01-30
GB1488674A (en)	1977-10-12
IL45643A (en)	1979-09-30
DE2446010C2 (de)	1985-05-15
JPS5059347A (da)	1975-05-22
IE40527B1 (en)	1979-06-20
GT197851174A (es)	1979-08-23
DE2446010A1 (de)	1975-04-03
FR2246267A1 (da)	1975-05-02
SE7412307L (da)	1975-04-02
NL179725C (nl)	1986-11-03
SE410595B (sv)	1979-10-22
IL45643A0 (en)	1974-11-29
DK141844B (da)	1980-06-30
ATA788574A (de)	1976-12-15
DD116031A5 (da)	1975-11-05
AT338250B (de)	1977-08-10
YU262274A (en)	1982-02-25

Legal Events

Date	Code	Title	Description
1997-05-20	MKEX	Expiry

Publication	Publication Date	Title
CA1077957A (en)	1980-05-20	Hypolipidemic 4-(monoalkylamino) benzoic acid derivatives
DE69409525T2 (de)	1998-08-06	Acetamidderivate und ihre verwendung als modifizierungsmittel des verhaltens der verdauung
CA1087205A (en)	1980-10-07	2-amino-3-(5-and 6-)benzoylphenylacetic acids, esters and metal salts thereof
RU2072986C1 (ru)	1997-02-10	Способ получения амидов карбоновых или сульфоновых кислот или их физиологически совместимых солей
DE2923815C2 (da)	1989-11-23
US4632934A (en)	1986-12-30	Imidazole derivatives and pharmaceutical use thereof
PT94231A (pt)	1991-02-08	Processo para a preparacao de compostos de ureia antihiperlipidemicos e anti-ateroscleroticos
JP2002322143A (ja)	2002-11-08	アミジン誘導体、その製法、及び医薬組成物
EP0504695A1 (de)	1992-09-23	Neue Carbonsäureamide, ihre Herstellung und pharmazeutische Präparate, die diese Verbindungen enthalten
US4185115A (en)	1980-01-22	Antilipidemic para-[aryl(alkyl or alkenyl)amino]-benzoic acid derivatives
US5512595A (en)	1996-04-30	Substituted phenoxyisobutyric acids and esters
US3639477A (en)	1972-02-01	Novel propoxyguanidine compounds and means of producing the same
FI76569C (fi)	1988-11-10	Foerfarande foer framstaellning av terapeutiskt aktiva substituerade imidazolderivat.
EP0165422B1 (de)	1988-03-09	Neue substituierte Bis(4-aminophenyl)sulfone, ihre Herstellung und ihre Verwendung als Arzneimittel
UA75353C2 (en)	2006-04-17	N-[2-hydroxy-3-(1-piperidinyl)propoxy]piridine-1-oxide-3-carboxamidine and a method for transformation thereof into pharmaceutically effective compounds
US4350822A (en)	1982-09-21	Antilipidemicpara-[aryl(alkyl or alkenyl)amino]benzoic acid derivatives
DE69108408T2 (de)	1995-07-27	4,5-dihydroxy und 4,5,8-trihydroxy-9,10-dioxo-2-anthracencarbonsäure-dikohlensäureester und urethane mit therapeutischer wirkung.
US3985875A (en)	1976-10-12	ω-(N-acylamino)alkylphosphoryl ethanolamines, pharmaceutical compositions containing them, and their uses
US3989746A (en)	1976-11-02	Substituted naphthyl anthranilic acids
CA1090366A (en)	1980-11-25	N-substituted aralkylanilines having hypolipidaemic activity
JPS61218571A (ja)	1986-09-29	新規ラクタム誘導体及び新規チオラクタム誘導体並びに抗炎症剤
EP0121806B1 (en)	1989-05-31	Pyrazolo(1,5-a)pyridine derivatives and compositions containing them
EP0491263A1 (de)	1992-06-24	Phenylalkylaminoalkyl-Verbindungen sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
KR810000354B1 (ko)	1981-04-22	4-(모노알킬아미노)-벤조산 유도체의 제조방법
DE2618936A1 (de)	1976-11-04	N-acylglutamine und verfahren zu ihrer herstellung