NO783690L - Fremgangsmaate ved fremstilling av nye farmakologisk aktive estere av 4-acetamidofenol - Google Patents

Fremgangsmaate ved fremstilling av nye farmakologisk aktive estere av 4-acetamidofenol

Info

Publication number: NO783690L
Authority: NO; Norway
Prior art keywords: phenoxyphenyl; propionate; acetamidophenyl; reacted; compound
Prior art date: 1977-11-03

Application number

NO783690A

Other languages

English (en)

Norwegian (no)

Inventor

George Margetts

Roderic Stafford Andrews

David Allan Matkin

Khalili Varasteh Houchang

Original Assignee

Sterwin Ag

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.)

1977-11-03

Filing date

1978-11-02

Publication date

1979-05-04

1978-11-02 Application filed by Sterwin Ag filed Critical Sterwin Ag

1979-05-04 Publication of NO783690L publication Critical patent/NO783690L/no

Links

238000000034 method Methods 0.000 title claims description 28
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 title claims description 15
238000002360 preparation method Methods 0.000 title description 18
230000000144 pharmacologic effect Effects 0.000 title description 2
-1 4-acetamidophenyl Chemical group 0.000 claims description 62
238000006243 chemical reaction Methods 0.000 claims description 24
RDJGLLICXDHJDY-UHFFFAOYSA-N fenoprofen Chemical compound OC(=O)C(C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-UHFFFAOYSA-N 0.000 claims description 20
150000008064 anhydrides Chemical class 0.000 claims description 14
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
239000004480 active ingredient Substances 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 8
239000007858 starting material Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
150000003512 tertiary amines Chemical class 0.000 claims description 6
RRVXBQXXJGDPNT-UHFFFAOYSA-N 2-(3-phenoxyphenyl)propanoyl chloride Chemical compound ClC(=O)C(C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RRVXBQXXJGDPNT-UHFFFAOYSA-N 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
GRDMQWRBLJZFML-UHFFFAOYSA-N bis(4-nitrophenyl) sulfite Chemical compound C1=CC([N+](=O)[O-])=CC=C1OS(=O)OC1=CC=C([N+]([O-])=O)C=C1 GRDMQWRBLJZFML-UHFFFAOYSA-N 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
ZHCAAFJSYLFLPX-UHFFFAOYSA-N nitrocyclohexatriene Chemical group [O-][N+](=O)C1=CC=C=C[CH]1 ZHCAAFJSYLFLPX-UHFFFAOYSA-N 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
239000012345 acetylating agent Substances 0.000 claims description 3
125000002877 alkyl aryl group Chemical group 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 2
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
WLWIFEZNLNMMRO-UHFFFAOYSA-N (3-phenoxyphenyl) propanoate Chemical compound CCC(=O)OC1=CC=CC(OC=2C=CC=CC=2)=C1 WLWIFEZNLNMMRO-UHFFFAOYSA-N 0.000 claims 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
229910021653 sulphate ion Inorganic materials 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 48
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
241000700159 Rattus Species 0.000 description 31
239000000203 mixture Substances 0.000 description 30
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 24
238000012360 testing method Methods 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
230000003110 anti-inflammatory effect Effects 0.000 description 14
229960001701 chloroform Drugs 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
150000002148 esters Chemical class 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
230000000202 analgesic effect Effects 0.000 description 11
230000000694 effects Effects 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
239000002253 acid Substances 0.000 description 9
239000002775 capsule Substances 0.000 description 9
230000002496 gastric effect Effects 0.000 description 9
206010003246 arthritis Diseases 0.000 description 8
239000012530 fluid Substances 0.000 description 8
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
206010061298 Mucosal haemorrhage Diseases 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
239000003826 tablet Substances 0.000 description 6
208000000114 Pain Threshold Diseases 0.000 description 5
239000003814 drug Substances 0.000 description 5
210000000548 hind-foot Anatomy 0.000 description 5
230000003902 lesion Effects 0.000 description 5
230000037040 pain threshold Effects 0.000 description 5
239000000725 suspension Substances 0.000 description 5
231100001274 therapeutic index Toxicity 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
239000003981 vehicle Substances 0.000 description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
239000000730 antalgic agent Substances 0.000 description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
230000037396 body weight Effects 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
230000002354 daily effect Effects 0.000 description 4
229940079593 drug Drugs 0.000 description 4
238000009472 formulation Methods 0.000 description 4
210000001035 gastrointestinal tract Anatomy 0.000 description 4
230000000968 intestinal effect Effects 0.000 description 4
210000002784 stomach Anatomy 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
240000004808 Saccharomyces cerevisiae Species 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
208000025865 Ulcer Diseases 0.000 description 3
206010000059 abdominal discomfort Diseases 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
229940035676 analgesics Drugs 0.000 description 3
230000001760 anti-analgesic effect Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000002245 particle Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
238000003756 stirring Methods 0.000 description 3
231100000397 ulcer Toxicity 0.000 description 3
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
241000416162 Astragalus gummifer Species 0.000 description 2
208000017667 Chronic Disease Diseases 0.000 description 2
208000032843 Hemorrhage Diseases 0.000 description 2
206010020565 Hyperaemia Diseases 0.000 description 2
208000002193 Pain Diseases 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229920001615 Tragacanth Polymers 0.000 description 2
239000011149 active material Substances 0.000 description 2
229940124599 anti-inflammatory drug Drugs 0.000 description 2
239000003849 aromatic solvent Substances 0.000 description 2
230000000740 bleeding effect Effects 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
230000001747 exhibiting effect Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000004615 ingredient Substances 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
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000003921 oil Substances 0.000 description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
230000036407 pain Effects 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000010183 spectrum analysis Methods 0.000 description 2
239000000829 suppository Substances 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-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
206010053155 Epigastric discomfort Diseases 0.000 description 1
241000400611 Eucalyptus deanei Species 0.000 description 1
244000166102 Eucalyptus leucoxylon Species 0.000 description 1
235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
206010020843 Hyperthermia Diseases 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 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
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
206010052428 Wound Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000036592 analgesia Effects 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
239000002221 antipyretic Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
238000004166 bioassay Methods 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
230000036760 body temperature Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000003203 everyday effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000036031 hyperthermia Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000007794 irritation Effects 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
229940111688 monobasic potassium phosphate Drugs 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
210000004877 mucosa Anatomy 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000006072 paste Substances 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940023488 pill Drugs 0.000 description 1
239000006187 pill Substances 0.000 description 1
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000008213 purified water Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000003307 slaughter Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000012798 spherical particle Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
229940098466 sublingual tablet Drugs 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000010998 test method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100000816 toxic dose Toxicity 0.000 description 1
238000005406 washing Methods 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

NO783690A 1977-11-03 1978-11-02 Fremgangsmaate ved fremstilling av nye farmakologisk aktive estere av 4-acetamidofenol NO783690L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB45700/77A GB1594226A (en)	1977-11-03	1977-11-03	Pharmacologically-active esters processes for their preparation and pharmaceutical compositions incorporating the pharmacologically-active esters

Publications (1)

Publication Number	Publication Date
NO783690L true NO783690L (no)	1979-05-04

Family

ID=10438213

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO783690A NO783690L (no)	1977-11-03	1978-11-02	Fremgangsmaate ved fremstilling av nye farmakologisk aktive estere av 4-acetamidofenol

Country Status (11)

Country	Link
AT (1)	AT363068B (de)
BE (1)	BE871757A (de)
DE (1)	DE2847063A1 (de)
DK (1)	DK488978A (de)
FI (1)	FI783332A7 (de)
FR (1)	FR2407913A1 (de)
GB (1)	GB1594226A (de)
LU (1)	LU80448A1 (de)
NL (1)	NL7810912A (de)
NO (1)	NO783690L (de)
SE (1)	SE7811381L (de)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT243263B (de) *	1963-05-13	1965-11-10	Lannacher Heilmittel	Verfahren zur Herstellung von neuen Estern des p-Acetaminophenols
GB1428803A (en) *	1973-05-29	1976-03-17	Gallardo Antonio Sa	4-acetamidophenyl esters of aryl-alkane carboxylic acids and a process for their preparation
IT1045533B (it) *	1974-05-15	1980-05-10	Acraf	P.isobutil idratropato di 4 acetamido fenile e procedimento per la sua prefarazione

1977
- 1977-11-03 GB GB45700/77A patent/GB1594226A/en not_active Expired
1978
- 1978-10-28 DE DE19782847063 patent/DE2847063A1/de not_active Withdrawn
- 1978-10-31 LU LU80448A patent/LU80448A1/de unknown
- 1978-11-01 FI FI783332A patent/FI783332A7/fi unknown
- 1978-11-02 NO NO783690A patent/NO783690L/no unknown
- 1978-11-02 FR FR7831092A patent/FR2407913A1/fr active Granted
- 1978-11-02 NL NL7810912A patent/NL7810912A/xx not_active Application Discontinuation
- 1978-11-02 DK DK488978A patent/DK488978A/da not_active Application Discontinuation
- 1978-11-02 AT AT0782778A patent/AT363068B/de not_active IP Right Cessation
- 1978-11-02 SE SE7811381A patent/SE7811381L/xx unknown
- 1978-11-03 BE BE191530A patent/BE871757A/xx unknown

Also Published As

Publication number	Publication date
FR2407913B1 (de)	1980-10-10
ATA782778A (de)	1980-12-15
NL7810912A (nl)	1979-05-07
BE871757A (fr)	1979-03-01
FR2407913A1 (fr)	1979-06-01
DK488978A (da)	1979-05-04
LU80448A1 (de)	1979-03-19
SE7811381L (sv)	1979-05-04
GB1594226A (en)	1981-07-30
FI783332A7 (fi)	1979-05-04
AT363068B (de)	1981-07-10
DE2847063A1 (de)	1979-05-10

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WO1989005799A1 (en)	1989-06-29	Novel tetrahydropyridine derivatives, pharmaceutical compositions containing them and process for preparing same
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