CH577480A5 - Alpha-aminophenyl aliphatic carboxylic acids - useful as anti-inflammatory agents, analgesics and anti-mycotics - Google Patents
Alpha-aminophenyl aliphatic carboxylic acids - useful as anti-inflammatory agents, analgesics and anti-mycoticsInfo
- Publication number
- CH577480A5 CH577480A5 CH1383169A CH1383169A CH577480A5 CH 577480 A5 CH577480 A5 CH 577480A5 CH 1383169 A CH1383169 A CH 1383169A CH 1383169 A CH1383169 A CH 1383169A CH 577480 A5 CH577480 A5 CH 577480A5
- Authority
- CH
- Switzerland
- Prior art keywords
- lower alkyl
- group
- phenyl
- formula
- hydrogen
- Prior art date
Links
- 230000001857 anti-mycotic effect Effects 0.000 title abstract 2
- 239000002260 anti-inflammatory agent Substances 0.000 title description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 title description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 title 1
- 229940035676 analgesics Drugs 0.000 title 1
- 239000002543 antimycotic Substances 0.000 title 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 73
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 23
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 15
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
- -1 1 -oxo-2-isoindolinyl Chemical group 0.000 claims description 111
- 150000001875 compounds Chemical class 0.000 claims description 68
- 150000003839 salts Chemical class 0.000 claims description 54
- 239000002253 acid Substances 0.000 claims description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 32
- 150000003254 radicals Chemical class 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 23
- 239000007858 starting material Substances 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000005907 alkyl ester group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 13
- 238000001953 recrystallisation Methods 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- 230000001419 dependent effect Effects 0.000 claims description 11
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 231100000252 nontoxic Toxicity 0.000 claims description 10
- 230000003000 nontoxic effect Effects 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 claims description 3
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 3
- 125000005237 alkyleneamino group Chemical group 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004494 ethyl ester group Chemical group 0.000 claims description 3
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- UTUVIKZNQWNGIM-UHFFFAOYSA-N ethyl 2-phenylpropanoate Chemical compound CCOC(=O)C(C)C1=CC=CC=C1 UTUVIKZNQWNGIM-UHFFFAOYSA-N 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 8
- 125000001302 tertiary amino group Chemical group 0.000 abstract description 3
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 abstract 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 150000004820 halides Chemical class 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 229910052751 metal Chemical class 0.000 description 4
- 239000002184 metal Chemical class 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 150000003556 thioamides Chemical class 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 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 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 210000000548 hind-foot Anatomy 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 235000015424 sodium Nutrition 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 2
- QQULFDKOSHUTTM-UHFFFAOYSA-N 2-phenyl-1,3-dihydroisoindole Chemical compound C1C2=CC=CC=C2CN1C1=CC=CC=C1 QQULFDKOSHUTTM-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 230000002917 arthritic effect Effects 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000005505 thiomorpholino group Chemical group 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- RIGLANWUDCRGIC-UHFFFAOYSA-N 2-[3-chloro-4-(1,3-dihydroisoindol-2-yl)phenyl]propanoic acid Chemical compound C1N(CC2=CC=CC=C12)C1=C(C=C(C=C1)C(C(=O)O)C)Cl RIGLANWUDCRGIC-UHFFFAOYSA-N 0.000 description 1
- GEAREAVHQHOXRA-UHFFFAOYSA-N 2-[4-(1,3-dihydroisoindol-2-yl)phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1N1CC2=CC=CC=C2C1 GEAREAVHQHOXRA-UHFFFAOYSA-N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- 125000005274 4-hydroxybenzoic acid group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 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
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
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- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
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- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- UJTRRNALUYKHQE-UHFFFAOYSA-N sodium;diphenylmethylbenzene Chemical compound [Na+].C1=CC=CC=C1[C-](C=1C=CC=CC=1)C1=CC=CC=C1 UJTRRNALUYKHQE-UHFFFAOYSA-N 0.000 description 1
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- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
-
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C—CHEMISTRY; METALLURGY
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
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- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/02—Preparation by ring-closure or hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (78)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL7009387A NL170852C (nl) | 1968-03-27 | 1970-06-25 | Werkwijze ter bereiding van farmaceutische preparaten en werkwijze ter bereiding van anti-inflammatoir werkzaam p-isoindolinylfenylazijnzuur en van derivaten hiervan. |
IL34873A IL34873A (en) | 1969-03-20 | 1970-07-08 | (bicyclic alkenylenimino)phenylaliphatic carboxylic acids and their functional derivatives,their preparation and pharmaceutical compositions containing them |
GB3337570A GB1316312A (en) | 1968-03-27 | 1970-07-09 | Tertiary aminoacids process for their manufacture and compositions containing them |
CY811A CY811A (en) | 1969-07-18 | 1970-07-09 | Tertiary aminoacids, process for their manufacture and compositions containing them |
IE899/70A IE34380B1 (en) | 1969-07-18 | 1970-07-10 | Tertiary aminoacids,process for their manufacture and compositions containing them |
DE19702034240 DE2034240C2 (de) | 1968-03-27 | 1970-07-10 | Isoindolinderivate, Verfahren zur Herstellung dieser Verbindungen und deren Verwendung |
CA087,966A CA990299A (en) | 1969-07-18 | 1970-07-13 | Tertiary aminoacids, process for their manufacture and compositions containing them |
PL18795570A PL102674B1 (pl) | 1969-07-18 | 1970-07-16 | Sposob wytwarzania nowych pochodnych alfa-/aminofenylo/-alifatycznych kwasow karboksylowych |
SU1846641A SU471715A3 (ru) | 1969-07-18 | 1970-07-16 | Способ получени -(аминофенил)алифатических карбоновых кислот или их солей |
FR7026096A FR2059527B2 (en, 2012) | 1968-03-27 | 1970-07-16 | |
BG021225A BG19588A3 (bg) | 1969-07-18 | 1970-07-16 | Метод за получаване на терциерни амино-киселини |
SU1774420A SU479283A3 (ru) | 1969-07-18 | 1970-07-16 | Способ получени -(аминофенил)алифатических карбоновых кислот или их производных,или их солей |
BG019461A BG20099A3 (bg) | 1969-07-18 | 1970-07-16 | Метод за получаване на терциерни аминокиселини |
PL20307370A PL103088B1 (pl) | 1969-07-18 | 1970-07-16 | Sposob wytwarzania nowych pochodnych alfa-(aminofenylo)-alifatycznych kwasow karboksylowych |
BG015202A BG20781A3 (bg) | 1969-07-18 | 1970-07-16 | Метод за получаване на терциерни аминокиселини |
PL20307970A PL106429B1 (pl) | 1969-07-18 | 1970-07-16 | Sposob wytwarzania nowych pochodnych 2-/aminofenylo/-alifatycznych kwasow karboksylowych |
SU1774416A SU471714A4 (ru) | 1969-07-18 | 1970-07-16 | Способ получени -(аминофенил)-алифатических карбоновых кислот или их производных,или их солей |
PL20307270A PL103087B1 (pl) | 1969-07-18 | 1970-07-16 | Sposob wytwarzania nowych pochodnych alfa-(aminofenylo)alifatycznych kwasow karboksylowych |
PL20307670A PL104401B1 (pl) | 1969-07-18 | 1970-07-16 | Sposob wytwarzania nowych pochodnych alfa-/aminofenylo/-alifatycznych kwasow karboksylowych |
SU1774418A SU455529A3 (ru) | 1969-07-18 | 1970-07-16 | Способ получени -(аминофенил)-алифатических карбоновых кислот или их производных или их солей |
SU1462497A SU458978A3 (ru) | 1969-09-12 | 1970-07-16 | Способ получени -(аминофенил)алифатических карбоновых кислот |
PL20307870A PL106915B1 (pl) | 1969-07-18 | 1970-07-16 | Sposob wytwarzania nowych pochodnych alfa-/aminofenylo/-alifatycznych kwasow karboksylowych |
SU1774417A SU473357A3 (ru) | 1969-07-18 | 1970-07-16 | Способ получени -(аминофенил)алифатических карбоновых кислот или их производных,или их солей |
PL20307470A PL103089B1 (pl) | 1969-07-18 | 1970-07-16 | Sposob wytwarzania nowych pochodnych alfa-/aminofenylo/-alifatycznych kwasow karboksylowych |
SU1768848A SU472499A3 (ru) | 1969-07-18 | 1970-07-16 | Способ получени -(аминофенил)-алифатических карбоновых кислот или их производных или солей |
PL20307770A PL104897B1 (pl) | 1969-07-18 | 1970-07-16 | Sposob wytwarzania nowych pochodnych alfa-/aminofenylo/-alifatycznych kwasow karboksylowych |
SU1774421A SU460618A3 (ru) | 1969-07-18 | 1970-07-16 | Способ получени (аминофенил) -алифатеических карбоновых кислот или их производных, или их солей |
BG019462A BG20563A3 (bg) | 1969-07-18 | 1970-07-16 | Метод за получаване на терциерни амино-киселини |
PL20307570A PL103092B1 (pl) | 1969-07-18 | 1970-07-16 | Sposob wytwarzania nowych pochodnych alfa-(aminofenylo)-alifatycznych kwasow karboksylowych |
AT130072A AT308093B (de) | 1969-07-18 | 1970-07-17 | Verfahren zur herstellung neuer heterocyclischer verbindungen und ihrer salze |
HUCI1014A HU167239B (en, 2012) | 1969-07-18 | 1970-07-17 | |
AT133972A AT308095B (de) | 1969-07-18 | 1970-07-17 | Verfahren zur herstellung neuer heterocyclischer verbindungen und ihrer salze |
AT134172A AT308743B (de) | 1968-03-27 | 1970-07-17 | Verfahren zur Herstellung neuer heterocyclischer Verbindungen und ihrer Salze |
AT134372A AT308096B (de) | 1969-07-18 | 1970-07-17 | Verfahren zur herstellung neuer heterocyclischer verbindungen und ihrer salze |
OA53986A OA149E (en, 2012) | 1969-07-18 | 1970-07-17 | |
AT129772A AT309413B (de) | 1969-07-18 | 1970-07-17 | Verfahren zur Herstellung neuer heterocyclischer Verbindungen und ihrer Salze |
AT688072A AT315163B (de) | 1969-07-18 | 1970-07-17 | Verfahren zur Herstellung neuer heterocyclischer Verbindungen und ihrer Salze |
AT133872A AT308741B (de) | 1969-07-18 | 1970-07-17 | Verfahren zur Herstellung neuer heterocyclischer Verbindungen und ihrer Salze |
AT129872A AT308091B (de) | 1969-07-18 | 1970-07-17 | Verfahren zur herstellung neuer heterocyclischer verbindungen und ihrer salze |
AT134072A AT308742B (de) | 1968-03-27 | 1970-07-17 | Verfahren zur Herstellung neuer heterocyclischer Verbindungen oder Salze davon |
AT134272A AT308744B (de) | 1969-07-18 | 1970-07-17 | Verfahren zur Herstellung neuer heterocyclischer Verbindungen und ihrer Salze |
AT133772A AT308740B (de) | 1969-07-18 | 1970-07-17 | Verfahren zur Herstellung neuer heterocyclischer Verbindungen und ihrer Salze |
AT129972A AT308092B (de) | 1969-07-18 | 1970-07-17 | Verfahren zur herstellung neuer heterocyclischer verbindungen und ihrer salze |
AT653570A AT309410B (de) | 1969-07-18 | 1970-07-17 | Verfahren zur Herstellung neuer heterocyclischer Verbindungen und ihrer Salze |
AT129672A AT308739B (de) | 1969-09-12 | 1970-07-17 | Verfahren zur Herstellung neuer heterocyclischer Verbindungen und ihrer Salze |
AT129572A AT308738B (de) | 1969-07-18 | 1970-07-17 | Verfahren zur Herstellung neuer heterocyclischer Verbindungen und ihrer Salze |
BE753600A BE753600R (fr) | 1968-03-27 | 1970-07-17 | Amino-acides |
AT129472A AT308737B (de) | 1969-07-18 | 1970-07-17 | Verfahren zur Herstellung neuer heterocyclischer Verbindungen und ihrer Salze |
AT133672A AT308094B (de) | 1969-07-18 | 1970-07-17 | Verfahren zur herstellung neuer heterocyclischer verbindungen und ihrer salze |
RO7000073290A RO62856A (fr) | 1969-07-18 | 1970-07-18 | Procede pour la preparation des aminoacides tertiaires |
JP45062579A JPS5035076B1 (en, 2012) | 1969-07-18 | 1970-07-18 | |
AR245379A AR199095A1 (es) | 1969-07-18 | 1972-11-29 | Procedimiento para la elaboracion de compuestos de acidos carboxilicos alfa-(amino-fenil)-alifaticos |
AR245378A AR194630A1 (es) | 1969-07-18 | 1972-11-29 | Procedimiento para obtener compuestos de acidos carboxilicos alfa(amino-fenil)alifaticos |
AR245380A AR198962A1 (es) | 1969-07-18 | 1972-11-29 | Procedimiento para la elaboracion de compuestos de acidos carboxilicos alpha - (amino-fenil)-alifaticos |
AR245538A AR206495A1 (es) | 1969-07-18 | 1972-12-07 | Procedimiento para la elaboracion de nuevos acidos carboxilicos alpha-(2-isoindolinil-o 1,2,3,4-tetrahidro-2-isoquinolil-fenil)-alifaticos |
AR245536A AR201655A1 (es) | 1969-07-18 | 1972-12-07 | Procedimiento para la elaboracion de compuestos de acidos carboxilicos alfa-(amino-fenli)-alifaticos |
AR245537A AR200992A1 (es) | 1969-07-18 | 1972-12-07 | Procedimiento para la elaboracion de compuestos de alpha-(aminofenil-alifaticos del acidocarboxilico, o sus sales |
AR247668A AR199480A1 (es) | 1969-07-18 | 1973-04-24 | Procedimiento para la elaboracion de nuevos acidos carboxilicos alfa-(amino-fenil)-alifaticos y sus derivados funcionales |
JP13418474A JPS5422976B1 (en, 2012) | 1969-07-18 | 1974-11-21 | |
JP13418874A JPS556628B1 (en, 2012) | 1969-07-18 | 1974-11-21 | |
JP13419674A JPS5344468B1 (en, 2012) | 1969-07-18 | 1974-11-21 | |
JP13419374A JPS5432779B1 (en, 2012) | 1969-07-18 | 1974-11-21 | |
JP13419574A JPS556629B1 (en, 2012) | 1969-07-18 | 1974-11-21 | |
JP13419474A JPS5427333B1 (en, 2012) | 1969-07-18 | 1974-11-21 | |
JP13419774A JPS557425B1 (en, 2012) | 1969-07-18 | 1974-11-21 | |
JP13418674A JPS5426536B1 (en, 2012) | 1969-07-18 | 1974-11-21 | |
JP13419974A JPS5427334B1 (en, 2012) | 1969-07-18 | 1974-11-21 | |
JP13418774A JPS556627B1 (en, 2012) | 1969-07-18 | 1974-11-21 | |
JP13419874A JPS5344469B1 (en, 2012) | 1969-07-18 | 1974-11-21 | |
JP13418574A JPS5425021B1 (en, 2012) | 1969-07-18 | 1974-11-21 | |
JP13419274A JPS5432778B1 (en, 2012) | 1969-07-18 | 1974-11-21 | |
JP13418974A JPS5432777B1 (en, 2012) | 1969-07-18 | 1974-11-21 | |
JP13419174A JPS5422971B1 (en, 2012) | 1969-07-18 | 1974-11-21 | |
JP13419074A JPS5422970B1 (en, 2012) | 1969-07-18 | 1974-11-21 | |
KE2544*UA KE2544A (en) | 1969-07-18 | 1975-07-10 | Tertiary aminoacids, process for their manufacture and compositions containing them |
MY150/75A MY7500150A (en) | 1969-07-18 | 1975-12-30 | Tertiary aminoacids, process for their manufacture and compositions containing them |
JP4791478A JPS5536660B1 (en, 2012) | 1969-07-18 | 1978-04-24 | |
JP53101940A JPS5745429B1 (en, 2012) | 1969-07-18 | 1978-08-23 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US84324469A | 1969-07-18 | 1969-07-18 |
Publications (1)
Publication Number | Publication Date |
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CH577480A5 true CH577480A5 (en) | 1976-07-15 |
Family
ID=25289436
Family Applications (13)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1383169A CH577480A5 (en) | 1968-03-27 | 1969-09-12 | Alpha-aminophenyl aliphatic carboxylic acids - useful as anti-inflammatory agents, analgesics and anti-mycotics |
CH935375A CH577482A5 (en, 2012) | 1969-07-18 | 1969-09-12 | |
CH935275A CH577481A5 (en, 2012) | 1969-07-18 | 1969-09-12 | |
CH935475A CH605792A5 (en, 2012) | 1969-07-18 | 1975-07-16 | |
CH1383169A CH579548A5 (en, 2012) | 1969-07-18 | 1975-07-16 | |
CH1383169A CH585722A5 (en, 2012) | 1969-07-18 | 1975-07-16 | |
CH1383169A CH585724A5 (en, 2012) | 1969-07-18 | 1975-07-16 | |
CH1383169A CH585727A5 (en, 2012) | 1969-07-18 | 1975-07-16 | |
CH1383169A CH585723A5 (en, 2012) | 1969-07-18 | 1975-07-16 | |
CH1383169A CH579541A5 (en, 2012) | 1969-07-18 | 1975-07-16 | |
CH1383169A CH585726A5 (en, 2012) | 1969-07-18 | 1975-07-16 | |
CH1383169A CH584690A5 (en, 2012) | 1969-07-18 | 1975-07-16 | |
CH1383169A CH585725A5 (en, 2012) | 1969-07-18 | 1975-07-16 |
Family Applications After (12)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH935375A CH577482A5 (en, 2012) | 1969-07-18 | 1969-09-12 | |
CH935275A CH577481A5 (en, 2012) | 1969-07-18 | 1969-09-12 | |
CH935475A CH605792A5 (en, 2012) | 1969-07-18 | 1975-07-16 | |
CH1383169A CH579548A5 (en, 2012) | 1969-07-18 | 1975-07-16 | |
CH1383169A CH585722A5 (en, 2012) | 1969-07-18 | 1975-07-16 | |
CH1383169A CH585724A5 (en, 2012) | 1969-07-18 | 1975-07-16 | |
CH1383169A CH585727A5 (en, 2012) | 1969-07-18 | 1975-07-16 | |
CH1383169A CH585723A5 (en, 2012) | 1969-07-18 | 1975-07-16 | |
CH1383169A CH579541A5 (en, 2012) | 1969-07-18 | 1975-07-16 | |
CH1383169A CH585726A5 (en, 2012) | 1969-07-18 | 1975-07-16 | |
CH1383169A CH584690A5 (en, 2012) | 1969-07-18 | 1975-07-16 | |
CH1383169A CH585725A5 (en, 2012) | 1969-07-18 | 1975-07-16 |
Country Status (8)
Country | Link |
---|---|
CH (13) | CH577480A5 (en, 2012) |
ES (1) | ES381910A2 (en, 2012) |
FI (1) | FI54106C (en, 2012) |
NO (1) | NO135938C (en, 2012) |
PL (6) | PL116578B1 (en, 2012) |
SE (1) | SE394670B (en, 2012) |
SU (1) | SU520040A3 (en, 2012) |
ZA (1) | ZA704666B (en, 2012) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US12195552B2 (en) | 2018-12-17 | 2025-01-14 | Remegen Co., Ltd. | Linker for antibody-drug conjugates and its use |
-
1969
- 1969-09-12 CH CH1383169A patent/CH577480A5/de not_active IP Right Cessation
- 1969-09-12 CH CH935375A patent/CH577482A5/xx not_active IP Right Cessation
- 1969-09-12 CH CH935275A patent/CH577481A5/xx not_active IP Right Cessation
- 1969-09-17 SE SE6912776A patent/SE394670B/xx unknown
- 1969-09-19 NO NO3751/69A patent/NO135938C/no unknown
- 1969-09-25 FI FI2750/69A patent/FI54106C/fi active
-
1970
- 1970-03-16 PL PL1970219921A patent/PL116578B1/pl unknown
- 1970-03-16 PL PL1970139442A patent/PL97082B3/pl unknown
- 1970-03-16 PL PL1970219916A patent/PL116504B1/pl unknown
- 1970-03-16 PL PL1970219917A patent/PL116729B1/pl unknown
- 1970-07-07 ZA ZA704666A patent/ZA704666B/xx unknown
- 1970-07-16 ES ES381910A patent/ES381910A2/es not_active Expired
- 1970-07-16 PL PL1970187953A patent/PL99354B1/pl unknown
- 1970-07-16 PL PL1970187954A patent/PL99355B1/pl unknown
-
1974
- 1974-05-28 SU SU2027897A patent/SU520040A3/ru active
-
1975
- 1975-07-16 CH CH935475A patent/CH605792A5/xx not_active IP Right Cessation
- 1975-07-16 CH CH1383169A patent/CH579548A5/xx not_active IP Right Cessation
- 1975-07-16 CH CH1383169A patent/CH585722A5/xx not_active IP Right Cessation
- 1975-07-16 CH CH1383169A patent/CH585724A5/xx not_active IP Right Cessation
- 1975-07-16 CH CH1383169A patent/CH585727A5/xx not_active IP Right Cessation
- 1975-07-16 CH CH1383169A patent/CH585723A5/xx not_active IP Right Cessation
- 1975-07-16 CH CH1383169A patent/CH579541A5/xx not_active IP Right Cessation
- 1975-07-16 CH CH1383169A patent/CH585726A5/xx not_active IP Right Cessation
- 1975-07-16 CH CH1383169A patent/CH584690A5/xx not_active IP Right Cessation
- 1975-07-16 CH CH1383169A patent/CH585725A5/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
SU520040A3 (ru) | 1976-06-30 |
FI54106B (fi) | 1978-06-30 |
NO135938B (en, 2012) | 1977-03-21 |
PL99355B1 (pl) | 1978-07-31 |
CH584690A5 (en, 2012) | 1977-02-15 |
CH577482A5 (en, 2012) | 1976-07-15 |
CH585725A5 (en, 2012) | 1977-03-15 |
CH577481A5 (en, 2012) | 1976-07-15 |
CH579541A5 (en, 2012) | 1976-09-15 |
FI54106C (fi) | 1978-10-10 |
CH605792A5 (en, 2012) | 1978-10-13 |
PL116578B1 (en) | 1981-06-30 |
SE394670B (sv) | 1977-07-04 |
PL116729B1 (en) | 1981-06-30 |
PL97082B3 (en) | 1978-02-28 |
NO135938C (en, 2012) | 1977-06-29 |
PL116504B1 (en) | 1981-06-30 |
ZA704666B (en) | 1971-03-31 |
CH585722A5 (en, 2012) | 1977-03-15 |
CH585727A5 (en, 2012) | 1977-03-15 |
CH579548A5 (en, 2012) | 1976-09-15 |
CH585724A5 (en, 2012) | 1977-03-15 |
CH585726A5 (en, 2012) | 1977-03-15 |
CH585723A5 (en, 2012) | 1977-03-15 |
ES381910A2 (es) | 1973-01-16 |
PL99354B1 (pl) | 1978-07-31 |
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Legal Events
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PL | Patent ceased | ||
PL | Patent ceased |