NO770152L - Fremgangsm}te for fremstilling av fysiologisk aktive p-benzylaminobenzoesyre-derivater. - Google Patents

Fremgangsm}te for fremstilling av fysiologisk aktive p-benzylaminobenzoesyre-derivater.

Info

Publication number: NO770152L
Authority: NO; Norway
Prior art keywords: schiff base; acid; benzoic acid; aminobenzoic acid; compounds
Prior art date: 1976-01-19

Application number

NO770152A

Other languages

English (en)

Norwegian (no)

Inventor

Eugene Ross Wagner

Bobbie Jewel Allen

Alfred Arthur Renzi

Original Assignee

Dow Chemical 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.)

1976-01-19

Filing date

1977-01-18

Publication date

1977-07-20

1977-01-18 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1977-07-20 Publication of NO770152L publication Critical patent/NO770152L/no

Links

238000000034 method Methods 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title description 13
NYNAMTQEBMCHNG-UHFFFAOYSA-N 4-(benzylamino)benzoic acid Chemical class C1=CC(C(=O)O)=CC=C1NCC1=CC=CC=C1 NYNAMTQEBMCHNG-UHFFFAOYSA-N 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims description 29
ALYNCZNDIQEVRV-UHFFFAOYSA-N aniline-p-carboxylic acid Natural products NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 18
239000002262 Schiff base Substances 0.000 claims description 13
150000004753 Schiff bases Chemical class 0.000 claims description 13
-1 hydroxy, carboxy Chemical group 0.000 claims description 13
229960004050 aminobenzoic acid Drugs 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 5
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
BKBMPNPZYZWGSX-UHFFFAOYSA-N 4-[(3-methoxyphenyl)methylamino]benzoic acid Chemical compound COC1=CC=CC(CNC=2C=CC(=CC=2)C(O)=O)=C1 BKBMPNPZYZWGSX-UHFFFAOYSA-N 0.000 claims description 2
GABPQBSNSDBMBK-UHFFFAOYSA-N 4-[(4-fluorophenyl)methylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NCC1=CC=C(F)C=C1 GABPQBSNSDBMBK-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 claims 2
UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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 9
230000000055 hyoplipidemic effect Effects 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
210000004369 blood Anatomy 0.000 description 5
239000008280 blood Substances 0.000 description 5
150000002632 lipids Chemical class 0.000 description 5
241000700159 Rattus Species 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
239000002585 base Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
235000012000 cholesterol Nutrition 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
210000002966 serum Anatomy 0.000 description 4
FVOJFMSKOLXBAW-UHFFFAOYSA-N 4-[(4-propan-2-ylphenyl)methylamino]benzoic acid Chemical compound C1=CC(C(C)C)=CC=C1CNC1=CC=C(C(O)=O)C=C1 FVOJFMSKOLXBAW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
235000005911 diet Nutrition 0.000 description 3
230000037213 diet Effects 0.000 description 3
YPTUAQWMBNZZRN-UHFFFAOYSA-N dimethylaminoboron Chemical compound [B]N(C)C YPTUAQWMBNZZRN-UHFFFAOYSA-N 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
210000004185 liver Anatomy 0.000 description 3
239000000047 product Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000002002 slurry Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
239000003826 tablet Substances 0.000 description 3
150000003626 triacylglycerols Chemical class 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000002253 acid Substances 0.000 description 2
BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
WTWBUQJHJGUZCY-UHFFFAOYSA-N cuminaldehyde Chemical compound CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000314 lubricant 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
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000000825 pharmaceutical preparation 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
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000013589 supplement Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical group NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
IFXSWTIWFGIXQO-AOOOYVTPSA-N 2-chloro-5-[(3s,5r)-3,5-dimethylpiperidin-1-yl]sulfonylbenzoic acid Chemical group C1[C@@H](C)C[C@@H](C)CN1S(=O)(=O)C1=CC=C(Cl)C(C(O)=O)=C1 IFXSWTIWFGIXQO-AOOOYVTPSA-N 0.000 description 1
ZWUSBSHBFFPRNE-UHFFFAOYSA-N 3,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1Cl ZWUSBSHBFFPRNE-UHFFFAOYSA-N 0.000 description 1
TVKKKDGJQZTLHL-UHFFFAOYSA-N 4-[(2-fluorophenyl)methylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NCC1=CC=CC=C1F TVKKKDGJQZTLHL-UHFFFAOYSA-N 0.000 description 1
QIANQKPXNXBLNW-UHFFFAOYSA-N 4-[(4-chlorophenyl)methylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NCC1=CC=C(Cl)C=C1 QIANQKPXNXBLNW-UHFFFAOYSA-N 0.000 description 1
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
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
208000037260 Atherosclerotic Plaque Diseases 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
241000173371 Garcinia indica Species 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
208000035150 Hypercholesterolemia Diseases 0.000 description 1
208000031226 Hyperlipidaemia Diseases 0.000 description 1
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 1
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 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
235000019485 Safflower oil Nutrition 0.000 description 1
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
241000906446 Theraps Species 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
150000001335 aliphatic alkanes 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
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
229910021529 ammonia Inorganic materials 0.000 description 1
239000010775 animal oil Substances 0.000 description 1
239000003524 antilipemic agent Substances 0.000 description 1
239000000305 astragalus gummifer gum Substances 0.000 description 1
WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
150000001559 benzoic acids Chemical class 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 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
235000021240 caseins Nutrition 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
235000012716 cod liver oil Nutrition 0.000 description 1
239000003026 cod liver oil Substances 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
230000008021 deposition Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000008157 edible vegetable oil Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000003516 hyperlipidaemic effect Effects 0.000 description 1
208000006575 hypertriglyceridemia Diseases 0.000 description 1
230000000871 hypocholesterolemic effect Effects 0.000 description 1
230000000999 hypotriglyceridemic effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000002513 implantation Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
235000013310 margarine Nutrition 0.000 description 1
239000003264 margarine Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
235000005713 safflower oil Nutrition 0.000 description 1
239000003813 safflower oil Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000243 solution Substances 0.000 description 1
235000019337 sorbitan trioleate Nutrition 0.000 description 1
229960000391 sorbitan trioleate Drugs 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
229950005201 tibric acid Drugs 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO770152A 1976-01-19 1977-01-18 Fremgangsm}te for fremstilling av fysiologisk aktive p-benzylaminobenzoesyre-derivater. NO770152L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US65008876A	1976-01-19	1976-01-19
US65008976A	1976-01-19	1976-01-19

Publications (1)

Publication Number	Publication Date
NO770152L true NO770152L (no)	1977-07-20

Family

ID=27095775

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO770152A NO770152L (no)	1976-01-19	1977-01-18	Fremgangsm}te for fremstilling av fysiologisk aktive p-benzylaminobenzoesyre-derivater.

Country Status (9)

Country	Link
JP (1)	JPS5289639A (da)
AU (1)	AU510758B2 (da)
BE (1)	BE850517A (da)
DE (1)	DE2701854A1 (da)
DK (1)	DK19677A (da)
FR (1)	FR2338246A1 (da)
GB (1)	GB1560281A (da)
NO (1)	NO770152L (da)
SE (1)	SE7700489L (da)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0006452B1 (en) *	1978-06-23	1983-02-16	The Dow Chemical Company	Hypoglycemic phenylpropynylamino benzoic acids, their salts, pharmaceutical compositions containing said compounds and their application
US4143151A (en) *	1978-07-03	1979-03-06	The Dow Chemical Company	Method for treating hyperglycemia in mammals using arylamino benzoic acids
GB9514160D0 (en) *	1994-07-25	1995-09-13	Zeneca Ltd	Aromatic compounds
GB9417532D0 (en) *	1994-08-31	1994-10-19	Zeneca Ltd	Aromatic compounds
GB9420557D0 (en) *	1994-10-12	1994-11-30	Zeneca Ltd	Aromatic compounds
TW502026B (en)	1995-06-20	2002-09-11	Zeneca Ltd	Aromatic compounds useful as antagonists of e-type prostaglandins, processes for the preparation thereof, pharmaceutical compositions comprising the compounds, and intermediates
TW434240B (en) *	1995-06-20	2001-05-16	Zeneca Ltd	Aromatic compounds, preparation thereof and pharmaceutical composition comprising same
EP0752421B1 (en) *	1995-07-07	2005-10-12	AstraZeneca AB	Ortho-substituted aromatic compounds, containing three (het)aryl moieties, their preparation and their use as prostaglandin E2-(PGE2)-antagonists
JP5175866B2 (ja) *	2007-02-22	2013-04-03	アイアールエム・リミテッド・ライアビリティ・カンパニー	Ｇタンパク質共役受容体を調節するための化合物および方法
WO2008121570A1 (en) *	2007-03-29	2008-10-09	Irm Llc	Compounds and methods for modulating g protein-coupled receptors
IT201600130047A1 (it) *	2016-12-22	2018-06-22	Univ Degli Studi Di Salerno	Derivati idrossi-benzenici recanti un gruppo imminico N-aril-sostituito e loro uso nel trattamento di tumori solidi
CN107162930B (zh) *	2017-06-13	2019-11-22	黄淮学院	用于识别超氧阴离子的荧光探针及其制备方法和应用、光纤探头及其制备方法
CN119081094B (zh) *	2024-11-11	2025-02-07	东营四叶草生态投资发展有限公司	一种起泡剂及其制备方法和应用

1977
- 1977-01-14 AU AU21344/77A patent/AU510758B2/en not_active Expired
- 1977-01-18 SE SE7700489A patent/SE7700489L/xx unknown
- 1977-01-18 NO NO770152A patent/NO770152L/no unknown
- 1977-01-18 GB GB1994/77A patent/GB1560281A/en not_active Expired
- 1977-01-18 FR FR7701294A patent/FR2338246A1/fr not_active Withdrawn
- 1977-01-18 DE DE19772701854 patent/DE2701854A1/de not_active Withdrawn
- 1977-01-19 DK DK19677A patent/DK19677A/da unknown
- 1977-01-19 BE BE174189A patent/BE850517A/xx unknown
- 1977-01-19 JP JP480677A patent/JPS5289639A/ja active Pending

Also Published As

Publication number	Publication date
JPS5289639A (en)	1977-07-27
FR2338246A1 (fr)	1977-08-12
DE2701854A1 (de)	1977-07-21
GB1560281A (en)	1980-02-06
BE850517A (fr)	1977-07-19
AU510758B2 (en)	1980-07-10
AU2134477A (en)	1978-07-20
SE7700489L (sv)	1977-07-20
DK19677A (da)	1977-07-20

Publication	Publication Date	Title
JP5422545B2 (ja)	2014-02-19	リン酸カルベジロール塩および／またはその溶媒和物、対応する組成物、および／または治療方法
NO770152L (no)	1977-07-20	Fremgangsm}te for fremstilling av fysiologisk aktive p-benzylaminobenzoesyre-derivater.
EP0047536B1 (en)	1984-06-27	Substituted propylamines
US5196412A (en)	1993-03-23	Gallium compounds
WO1999002512A1 (en)	1999-01-21	Dl-2,3-diaryl-2h-1-benzopyrans
JPS5925794B2 (ja)	1984-06-21	尿素のヘテロシクリルカルボニル誘導体
US20120309990A1 (en)	2012-12-06	Processes for the Purification of Lubiprostone
US4594443A (en)	1986-06-10	Derivatives of 4-phenyl-4-oxo-buten-2-oic acid and therapeutic use thereof
DK168432B1 (da)	1994-03-28	Polyprenylforbindelser og farmaceutiske kompositioner indeholdende forbindelserne
EP0037991A1 (en)	1981-10-21	4-Alkylsubstituted-3-hydroxy-2-pyrroline-2,5-dione compounds for use in the prevention and treatment of kidney and bladder stones, process for preparing them and pharmaceutical composition containing them
US4067998A (en)	1978-01-10	2-((3,5-Di-tert-butylphenyl)thio) alkanoic acids and derivatives
FR2515175A1 (fr)	1983-04-29	Nouveaux derives de l'acide 4-phenyl 4-oxo 2-butenoique, leurs sels, leur preparation, leur application comme medicaments et les compositions les renfermant
CA1128960A (en)	1982-08-03	Hypoglycemic phenylpropynylamino benzoic acids
HU182913B (en)	1984-03-28	Process for preparing compounds of dilignol type
US3558645A (en)	1971-01-26	2-(4-(4',5-diphenyl - 2 - imidazolyl)-phenoxy) lower aliphatic monocarboxylic acids
US4103029A (en)	1978-07-25	Amino substituted arylthio-alkanoic acids having hypolipidemic activity
US4133890A (en)	1979-01-09	Hypolipidemic compositions and method employing derivatives of 4-(((1,3-benzodioxol-5-yl)methyl)amino)benzoic acid
NO145839B (no)	1982-03-01	Analogifremgangsmaate for fremstilling av hypolipidemiske p-aminobenzoesyrer
US3598860A (en)	1971-08-10	2 - (4 -(3',4' - diphenylcyclopentyl)-phenoxy) lower aliphatic monocarbocyclic acids and esters thereof
WO2020234423A1 (en)	2020-11-26	Siponimod maleic acid and fumaric acid salt
CA1106389A (en)	1981-08-04	2-(phenylalkylhydrazono)-propionic acid derivatives and the preparation thereof
US4218475A (en)	1980-08-19	Hypolipidemic benzylaminobenzene alkanoic or alkenoic acids
US4192884A (en)	1980-03-11	Substituted 4-(((thienyl)methyl)-amino)benzoic acids and a method for treating hypolipidemia
US4034045A (en)	1977-07-05	2,4-Disubstituted-4b,5,6,7,8,8a,9,10-octahydro-9-oxo-phenanthrenes
US3931409A (en)	1976-01-06	Composition and method for treatment of hyperuricemia