DE2248580A1 - 3-tert.-butyl-6-methyl-5-nitrosalicylsaeureanilide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate - Google Patents
3-tert.-butyl-6-methyl-5-nitrosalicylsaeureanilide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparateInfo
- Publication number
- DE2248580A1 DE2248580A1 DE19722248580 DE2248580A DE2248580A1 DE 2248580 A1 DE2248580 A1 DE 2248580A1 DE 19722248580 DE19722248580 DE 19722248580 DE 2248580 A DE2248580 A DE 2248580A DE 2248580 A1 DE2248580 A1 DE 2248580A1
- Authority
- DE
- Germany
- Prior art keywords
- tert
- general formula
- butyl
- methyl
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 150000001875 compounds Chemical class 0.000 title claims description 36
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 6
- 229940126601 medicinal product Drugs 0.000 title description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 claims description 8
- 229950000975 salicylanilide Drugs 0.000 claims description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 229910017604 nitric acid Inorganic materials 0.000 claims description 7
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 3
- 229960004889 salicylic acid Drugs 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 1
- -1 5-tert-butyl-6 methyl-5-nitrosalicylic anilide Chemical compound 0.000 description 15
- 241001494479 Pecora Species 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 241000242711 Fasciola hepatica Species 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 208000006275 fascioliasis Diseases 0.000 description 11
- 241000699670 Mus sp. Species 0.000 description 9
- 244000045947 parasite Species 0.000 description 9
- 206010061217 Infestation Diseases 0.000 description 8
- FTCUFQRGPJZIID-UHFFFAOYSA-N [2-(phenylcarbamoyl)phenyl] nitrate Chemical compound [O-][N+](=O)OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 FTCUFQRGPJZIID-UHFFFAOYSA-N 0.000 description 7
- 241000242722 Cestoda Species 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 241000282849 Ruminantia Species 0.000 description 5
- 150000003931 anilides Chemical class 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 235000013601 eggs Nutrition 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 241000243976 Haemonchus Species 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RZGWIZIPFZROQZ-UHFFFAOYSA-N 2-methoxy-n-phenylbenzamide Chemical compound COC1=CC=CC=C1C(=O)NC1=CC=CC=C1 RZGWIZIPFZROQZ-UHFFFAOYSA-N 0.000 description 3
- JXQCUCDXLSGQNZ-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methylbenzoic acid Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1C(O)=O JXQCUCDXLSGQNZ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241001464384 Hymenolepis nana Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000244206 Nematoda Species 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- QANDJRKMSAUDCP-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-6-methyl-5-nitrobenzoic acid Chemical compound CC1=C(C(O)=O)C(O)=C(C(C)(C)C)C=C1[N+]([O-])=O QANDJRKMSAUDCP-UHFFFAOYSA-N 0.000 description 2
- 241000243974 Haemonchus contortus Species 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 241000255777 Lepidoptera Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 235000019764 Soybean Meal Nutrition 0.000 description 2
- 230000001055 chewing effect Effects 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 230000002496 gastric effect Effects 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
- RJMUSRYZPJIFPJ-UHFFFAOYSA-N niclosamide Chemical compound OC1=CC=C(Cl)C=C1C(=O)NC1=CC=C([N+]([O-])=O)C=C1Cl RJMUSRYZPJIFPJ-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 2
- 239000004455 soybean meal Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 239000010455 vermiculite Substances 0.000 description 2
- 229910052902 vermiculite Inorganic materials 0.000 description 2
- 235000019354 vermiculite Nutrition 0.000 description 2
- BZVYEQLTYLFTNH-UHFFFAOYSA-N 2-hydroxy-5-nitro-n-phenylbenzamide Chemical compound OC1=CC=C([N+]([O-])=O)C=C1C(=O)NC1=CC=CC=C1 BZVYEQLTYLFTNH-UHFFFAOYSA-N 0.000 description 1
- FXUAAFDHVMXKHO-UHFFFAOYSA-N 2-hydroxy-6-methyl-n-phenylbenzamide Chemical compound CC1=CC=CC(O)=C1C(=O)NC1=CC=CC=C1 FXUAAFDHVMXKHO-UHFFFAOYSA-N 0.000 description 1
- HUHQPZXYXMNRGW-UHFFFAOYSA-N 2-hydroxy-n-(2-methoxy-4-nitrophenyl)benzamide Chemical compound COC1=CC([N+]([O-])=O)=CC=C1NC(=O)C1=CC=CC=C1O HUHQPZXYXMNRGW-UHFFFAOYSA-N 0.000 description 1
- WCNOIIANCVJUDY-UHFFFAOYSA-N 2-hydroxy-n-[2-(trifluoromethyl)phenyl]benzamide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(F)(F)F WCNOIIANCVJUDY-UHFFFAOYSA-N 0.000 description 1
- HOTZLWVITTVZGY-UHFFFAOYSA-N 4-nitro-2-(trifluoromethyl)aniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(F)(F)F HOTZLWVITTVZGY-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000415078 Anemone hepatica Species 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000931178 Bunostomum Species 0.000 description 1
- 241000244203 Caenorhabditis elegans Species 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 241001126268 Cooperia Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 241000498255 Enterobius vermicularis Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000242689 Fasciola Species 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 206010017964 Gastrointestinal infection Diseases 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 241000545744 Hirudinea Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000243795 Ostertagia Species 0.000 description 1
- 241000283903 Ovis aries Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000468389 Pseudombrophila hepatica Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000244174 Strongyloides Species 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 241000869417 Trematodes Species 0.000 description 1
- 241000243797 Trichostrongylus Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 210000003165 abomasum Anatomy 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000003975 animal breeding Methods 0.000 description 1
- 239000003837 anticestodal agent Substances 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 210000002257 embryonic structure Anatomy 0.000 description 1
- 206010014881 enterobiasis Diseases 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- XBNNLAWQCMDISJ-UHFFFAOYSA-N n-ethyl-4-nitroaniline Chemical compound CCNC1=CC=C([N+]([O-])=O)C=C1 XBNNLAWQCMDISJ-UHFFFAOYSA-N 0.000 description 1
- 229960001920 niclosamide Drugs 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 210000004767 rumen Anatomy 0.000 description 1
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C205/60—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms in ortho-position to the carboxyl group, e.g. nitro-salicylic acids
-
- 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
- C07C233/12—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 halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fodder In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18651471A | 1971-10-04 | 1971-10-04 | |
| DE19732347615 DE2347615A1 (de) | 1971-10-04 | 1973-09-21 | 3-tert.-butyl-4'-brom-6-methyl-5nitro-2'-trifluormethylsalicylsaeureanilid, verfahren zu seiner herstellung und diese verbindung enthaltende arzneipraeparate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2248580A1 true DE2248580A1 (de) | 1973-04-12 |
Family
ID=25765838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722248580 Ceased DE2248580A1 (de) | 1971-10-04 | 1972-10-04 | 3-tert.-butyl-6-methyl-5-nitrosalicylsaeureanilide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate |
Country Status (11)
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3721737A (en) * | 1968-11-15 | 1973-03-20 | Monsanto Co | 2',5'-dihalo-3-tert.alkyl-5-nitrosalicylanilides for combatting lepidoptera chewing larvae |
-
1972
- 1972-09-06 ZA ZA726087A patent/ZA726087B/xx unknown
- 1972-09-20 BE BE789027D patent/BE789027A/xx unknown
- 1972-09-27 FR FR7234127A patent/FR2155947B1/fr not_active Expired
- 1972-09-28 AR AR244336A patent/AR197003A1/es active
- 1972-10-02 NL NL7213293A patent/NL7213293A/xx not_active Application Discontinuation
- 1972-10-02 LU LU66215A patent/LU66215A1/xx unknown
- 1972-10-03 GB GB4553672A patent/GB1356717A/en not_active Expired
- 1972-10-03 CH CH1339572A patent/CH577466A5/xx not_active IP Right Cessation
- 1972-10-03 JP JP47099364A patent/JPS4844230A/ja active Pending
- 1972-10-04 DE DE19722248580 patent/DE2248580A1/de not_active Ceased
- 1972-10-04 BR BR006892/72A patent/BR7206892D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2155947A1 (enrdf_load_stackoverflow) | 1973-05-25 |
| BR7206892D0 (pt) | 1973-12-06 |
| ZA726087B (en) | 1973-06-27 |
| AR197003A1 (es) | 1974-03-08 |
| CH577466A5 (enrdf_load_stackoverflow) | 1976-07-15 |
| BE789027A (fr) | 1973-03-20 |
| JPS4844230A (enrdf_load_stackoverflow) | 1973-06-26 |
| LU66215A1 (enrdf_load_stackoverflow) | 1973-01-23 |
| NL7213293A (enrdf_load_stackoverflow) | 1973-04-06 |
| FR2155947B1 (enrdf_load_stackoverflow) | 1976-05-21 |
| GB1356717A (en) | 1974-06-12 |
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