NO122313B - - Google Patents
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- Publication number
- NO122313B NO122313B NO4777/68A NO477768A NO122313B NO 122313 B NO122313 B NO 122313B NO 4777/68 A NO4777/68 A NO 4777/68A NO 477768 A NO477768 A NO 477768A NO 122313 B NO122313 B NO 122313B
- Authority
- NO
- Norway
- Prior art keywords
- salicylanilide
- iodine
- chloro
- substituted
- approx
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 23
- 229950000975 salicylanilide Drugs 0.000 claims description 20
- -1 p-chlorophenoxy Chemical group 0.000 claims description 14
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical class OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 15
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 10
- 229910052740 iodine Inorganic materials 0.000 description 10
- 239000011630 iodine Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000026030 halogenation Effects 0.000 description 4
- 238000005658 halogenation reaction Methods 0.000 description 4
- 230000026045 iodination Effects 0.000 description 4
- 238000006192 iodination reaction Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- CHKZQFKTASXYIP-UHFFFAOYSA-N 2,6-dichloro-5-[4,6-dichloro-6-(4-nitrophenyl)cyclohexa-2,4-dien-1-yl]oxy-6-(4-nitrophenyl)cyclohexa-1,3-diene Chemical compound ClC1(C(C=CC(=C1)Cl)OC1C(C=C(C=C1)Cl)(Cl)C1=CC=C(C=C1)[N+](=O)[O-])C1=CC=C(C=C1)[N+](=O)[O-] CHKZQFKTASXYIP-UHFFFAOYSA-N 0.000 description 3
- 241000242711 Fasciola hepatica Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000507 anthelmentic effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002496 iodine Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- NEMNPWINWMHUMR-UHFFFAOYSA-N rafoxanide Chemical compound OC1=C(I)C=C(I)C=C1C(=O)NC(C=C1Cl)=CC=C1OC1=CC=C(Cl)C=C1 NEMNPWINWMHUMR-UHFFFAOYSA-N 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- OQOCWFFSZSSEDS-UHFFFAOYSA-N 3-chloro-4-(4-chlorophenoxy)aniline Chemical compound ClC1=CC(N)=CC=C1OC1=CC=C(Cl)C=C1 OQOCWFFSZSSEDS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DQCIJCWJTRSUKT-UHFFFAOYSA-N N-[3-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxybenzamide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC(Cl)=C(OC2=CC=C(Cl)C=C2)C=C1 DQCIJCWJTRSUKT-UHFFFAOYSA-N 0.000 description 2
- 208000030852 Parasitic disease Diseases 0.000 description 2
- 150000003931 anilides Chemical group 0.000 description 2
- 229940124339 anthelmintic agent Drugs 0.000 description 2
- 239000000921 anthelmintic agent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 2
- ZEMAAAKSMFAZIM-UHFFFAOYSA-N n-phenylsulfanylaniline Chemical compound C=1C=CC=CC=1NSC1=CC=CC=C1 ZEMAAAKSMFAZIM-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- NYWVNRRGNPHTLI-UHFFFAOYSA-N 1,2-dichloro-3,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1[N+]([O-])=O NYWVNRRGNPHTLI-UHFFFAOYSA-N 0.000 description 1
- CMVQZRLQEOAYSW-UHFFFAOYSA-N 1,2-dichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Cl CMVQZRLQEOAYSW-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZRFNUPCFDKEQTA-UHFFFAOYSA-N 2-hydroxy-3,4-diiodo-n-phenylbenzamide Chemical compound OC1=C(I)C(I)=CC=C1C(=O)NC1=CC=CC=C1 ZRFNUPCFDKEQTA-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- SBUNWTUXZOCIGZ-UHFFFAOYSA-N 3,5-dibromo-n-[3-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxybenzamide Chemical compound OC1=C(Br)C=C(Br)C=C1C(=O)NC(C=C1Cl)=CC=C1OC1=CC=C(Cl)C=C1 SBUNWTUXZOCIGZ-UHFFFAOYSA-N 0.000 description 1
- MBBBYNIMRQZPDR-UHFFFAOYSA-N 4-[2-[2-(4-amino-2-chlorophenyl)-4-chlorophenoxy]-5-chlorophenyl]-3-chloroaniline Chemical compound ClC1=CC(N)=CC=C1C1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1C1=CC=C(N)C=C1Cl MBBBYNIMRQZPDR-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- 241000415078 Anemone hepatica Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000204939 Fasciola gigantica Species 0.000 description 1
- 108010034145 Helminth Proteins Proteins 0.000 description 1
- 241001662043 Icterus Species 0.000 description 1
- 206010023126 Jaundice Diseases 0.000 description 1
- LUKVWSUSIKQSBE-UHFFFAOYSA-N N-[2-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl]-2-hydroxybenzamide Chemical compound ClC1=C(NC(C=2C(O)=CC=CC2)=O)C=CC(=C1)OC1=CC(=CC=C1)C(F)(F)F LUKVWSUSIKQSBE-UHFFFAOYSA-N 0.000 description 1
- 208000000291 Nematode infections Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 208000002474 Tinea Diseases 0.000 description 1
- 241000893966 Trichophyton verrucosum Species 0.000 description 1
- UYPAJBPYDFUMSN-UHFFFAOYSA-N [2-(phenylcarbamoyl)phenyl] hypoiodite Chemical class IOC=1C(C(=O)NC2=CC=CC=C2)=CC=CC=1 UYPAJBPYDFUMSN-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 208000006275 fascioliasis Diseases 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- CBEQRNSPHCCXSH-UHFFFAOYSA-N iodine monobromide Chemical compound IBr CBEQRNSPHCCXSH-UHFFFAOYSA-N 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 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
- 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
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04C—STRUCTURAL ELEMENTS; BUILDING MATERIALS
- E04C5/00—Reinforcing elements, e.g. for concrete; Auxiliary elements therefor
- E04C5/16—Auxiliary parts for reinforcements, e.g. connectors, spacers, stirrups
- E04C5/18—Spacers of metal or substantially of metal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US68712867A | 1967-12-01 | 1967-12-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
NO122313B true NO122313B (enrdf_load_stackoverflow) | 1971-06-14 |
Family
ID=24759178
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO4777/68A NO122313B (enrdf_load_stackoverflow) | 1967-12-01 | 1968-11-29 |
Country Status (12)
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL184257C (nl) * | 1974-06-19 | 1989-06-01 | Merck & Co Inc | Werkwijze voor het bereiden van rafoxanide preparaten. |
-
1968
- 1968-11-14 NL NL6816239A patent/NL6816239A/xx unknown
- 1968-11-19 IL IL31105A patent/IL31105A/en unknown
- 1968-11-22 ES ES360542A patent/ES360542A1/es not_active Expired
- 1968-11-25 DE DE19681810821 patent/DE1810821A1/de active Pending
- 1968-11-25 GB GB55818/68A patent/GB1212628A/en not_active Expired
- 1968-11-26 YU YU2768/68A patent/YU32305B/xx unknown
- 1968-11-27 AT AT1155268A patent/AT293363B/de not_active IP Right Cessation
- 1968-11-27 SE SE16156/68A patent/SE368394B/xx unknown
- 1968-11-29 NO NO4777/68A patent/NO122313B/no unknown
- 1968-11-29 BR BR204469/68A patent/BR6804469D0/pt unknown
- 1968-11-29 CH CH1782068A patent/CH526514A/de not_active IP Right Cessation
- 1968-12-02 CS CS688206A patent/CS149651B2/cs unknown
Also Published As
Publication number | Publication date |
---|---|
IL31105A0 (en) | 1969-01-29 |
YU32305B (en) | 1974-08-31 |
BR6804469D0 (pt) | 1973-02-22 |
AT293363B (de) | 1971-10-11 |
DE1810821A1 (de) | 1969-07-17 |
YU276868A (en) | 1974-02-28 |
CH526514A (de) | 1972-08-15 |
NL6816239A (enrdf_load_stackoverflow) | 1969-06-03 |
GB1212628A (en) | 1970-11-18 |
CS149651B2 (en) | 1973-07-25 |
IL31105A (en) | 1972-08-30 |
ES360542A1 (es) | 1970-10-16 |
SE368394B (enrdf_load_stackoverflow) | 1974-07-01 |
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