IL31105A - The legogenesis of salicylanilides - Google Patents
The legogenesis of salicylanilidesInfo
- Publication number
- IL31105A IL31105A IL31105A IL3110568A IL31105A IL 31105 A IL31105 A IL 31105A IL 31105 A IL31105 A IL 31105A IL 3110568 A IL3110568 A IL 3110568A IL 31105 A IL31105 A IL 31105A
- Authority
- IL
- Israel
- Prior art keywords
- salicylanilide
- chloro
- iodine
- chlorophenoxy
- grams
- Prior art date
Links
- 230000026030 halogenation Effects 0.000 title description 2
- 238000005658 halogenation reaction Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 27
- 229950000975 salicylanilide Drugs 0.000 claims description 27
- -1 4 '- (m-trifluoromethyl-phenoxy) -salicylanilide Chemical compound 0.000 claims description 25
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical group ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 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 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 239000012336 iodinating agent Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 description 13
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 229910052740 iodine Inorganic materials 0.000 description 9
- 239000011630 iodine Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound 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
- 229960000583 acetic acid Drugs 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 239000011541 reaction mixture 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
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 241000242711 Fasciola hepatica Species 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 230000026045 iodination Effects 0.000 description 4
- 238000006192 iodination reaction Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 238000001816 cooling Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
- 239000003208 petroleum Substances 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
- 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
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 238000005660 chlorination reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 208000006275 fascioliasis Diseases 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
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002496 iodine 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
- 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 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-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
- JKIFPWHZEZQCQA-UHFFFAOYSA-N 2-nitrobenzenethiol Chemical compound [O-][N+](=O)C1=CC=CC=C1S JKIFPWHZEZQCQA-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
- WTPFYPUXUHYGIP-UHFFFAOYSA-N 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline Chemical compound ClC1=CC(N)=CC=C1OC1=CC=CC(C(F)(F)F)=C1 WTPFYPUXUHYGIP-UHFFFAOYSA-N 0.000 description 1
- PMYJFDMQUGPXGM-UHFFFAOYSA-N 4-(4-bromophenoxy)-3-chloroaniline Chemical compound ClC1=CC(N)=CC=C1OC1=CC=C(Br)C=C1 PMYJFDMQUGPXGM-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
- 241000283690 Bos taurus Species 0.000 description 1
- PMLSTCYISWIHAC-UHFFFAOYSA-N ClC=1C=C(NC(C=2C(O)=CC=CC2)=O)C=CC1OC1=CC=C(C=C1)OC Chemical compound ClC=1C=C(NC(C=2C(O)=CC=CC2)=O)C=CC1OC1=CC=C(C=C1)OC PMLSTCYISWIHAC-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 208000025011 Distomatosis Diseases 0.000 description 1
- 241000204939 Fasciola gigantica Species 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
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 208000000291 Nematode infections Diseases 0.000 description 1
- 241000935974 Paralichthys dentatus Species 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 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
- 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
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000727 fraction Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- CBEQRNSPHCCXSH-UHFFFAOYSA-N iodine monobromide Chemical compound IBr CBEQRNSPHCCXSH-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- ZEMAAAKSMFAZIM-UHFFFAOYSA-N n-phenylsulfanylaniline Chemical compound C=1C=CC=CC=1NSC1=CC=CC=C1 ZEMAAAKSMFAZIM-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 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
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 239000002002 slurry Substances 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
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 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 (2)
| Publication Number | Publication Date |
|---|---|
| IL31105A0 IL31105A0 (en) | 1969-01-29 |
| IL31105A true IL31105A (en) | 1972-08-30 |
Family
ID=24759178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL31105A IL31105A (en) | 1967-12-01 | 1968-11-19 | The legogenesis of salicylanilides |
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 |
| NO122313B (enrdf_load_stackoverflow) | 1971-06-14 |
| 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 |
| ES360542A1 (es) | 1970-10-16 |
| SE368394B (enrdf_load_stackoverflow) | 1974-07-01 |
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