US3706799A - Naphthyloxysalicylanilides - Google Patents
Naphthyloxysalicylanilides Download PDFInfo
- Publication number
- US3706799A US3706799A US881869A US3706799DA US3706799A US 3706799 A US3706799 A US 3706799A US 881869 A US881869 A US 881869A US 3706799D A US3706799D A US 3706799DA US 3706799 A US3706799 A US 3706799A
- Authority
- US
- United States
- Prior art keywords
- gms
- naphthyloxy
- mole
- naphthylether
- substituted
- 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.)
- Expired - Lifetime
Links
- 150000003931 anilides Chemical class 0.000 abstract description 21
- 230000002070 germicidal effect Effects 0.000 abstract description 10
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 150000002367 halogens Chemical group 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 229950000975 salicylanilide Drugs 0.000 description 15
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- -1 naphthyloxy salicylanilide Chemical compound 0.000 description 8
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 8
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 3
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 3
- NKBASRXWGAGQDP-UHFFFAOYSA-N 5-chlorosalicylic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1O NKBASRXWGAGQDP-UHFFFAOYSA-N 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000002026 chloroform extract Substances 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
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- CLHFZBNPEGAHET-UHFFFAOYSA-N 2-hydroxy-n-(2-naphthalen-2-yloxyphenyl)benzamide Chemical class OC1=CC=CC=C1C(=O)NC1=CC=CC=C1OC1=CC=C(C=CC=C2)C2=C1 CLHFZBNPEGAHET-UHFFFAOYSA-N 0.000 description 2
- MFUVCHZWGSJKEQ-UHFFFAOYSA-N 3,4-dichlorphenylisocyanate Chemical compound ClC1=CC=C(N=C=O)C=C1Cl MFUVCHZWGSJKEQ-UHFFFAOYSA-N 0.000 description 2
- CNJGWCQEGROXEE-UHFFFAOYSA-N 3,5-Dichlorosalicylicacid Chemical compound OC(=O)C1=CC(Cl)=CC(Cl)=C1O CNJGWCQEGROXEE-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- RZKKOBGFCAHLCZ-UHFFFAOYSA-N 1,4-dichloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1Cl RZKKOBGFCAHLCZ-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- ZBXSCCRCUICGEX-UHFFFAOYSA-N 3,4-dibromo-n-(4-bromophenyl)-2-hydroxybenzamide Chemical compound OC1=C(Br)C(Br)=CC=C1C(=O)NC1=CC=C(Br)C=C1 ZBXSCCRCUICGEX-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- RUVFRGLMZQWVBG-UHFFFAOYSA-N 5-chloro-2-hydroxy-n-(2-naphthalen-2-yloxyphenyl)benzamide Chemical compound OC1=CC=C(Cl)C=C1C(=O)NC1=CC=CC=C1OC1=CC=C(C=CC=C2)C2=C1 RUVFRGLMZQWVBG-UHFFFAOYSA-N 0.000 description 1
- DFGKGUXTPFWHIX-UHFFFAOYSA-N 6-[2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]acetyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)C1=CC2=C(NC(O2)=O)C=C1 DFGKGUXTPFWHIX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 229940124536 anticoccidial agent Drugs 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003224 coccidiostatic agent Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- ICUTUKXCWQYESQ-UHFFFAOYSA-N triclocarban Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 ICUTUKXCWQYESQ-UHFFFAOYSA-N 0.000 description 1
- KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
Definitions
- the present invention relates to a new class of biologically active compounds.
- an anilide contains a naphthyloxy substituent said anilide is a surprisingly effective biocidal agent.
- presence of the weighty naphthyloxy group instead of the comparatively light phenoxy group gives comparable biocidal activity and in some instances more favourable activity.
- said anilide is selected from the class of salicylanilides and carbanilides. It has been found that such naphthyloxy-substituted anilides show surprising germicidal activity. Also, they can be used advantageously in conjunction with detergents.
- the scope of the invention includes a naphthyloxy-substituted anilide in which said anilide is selected from the class consisting of salicylanilides and carbanilides.
- said naphthyloxy-substituent is in the aromatic ring of an aniline group in said anilide, particularly in the 2, Le. ortho, position of said aromatic ring.
- Particularly preferred compounds of the invention are naphthyloxy-substituted anilides in which said anilide is selected from the class consisting of halogen-substituted salicylanilides and carbanilides. Other substituents can be present.
- the halogen is chlorine or bromine and preferably the anilide contains from 1 to 3 halogen atoms.
- An aspect of the invention is a germicidal composition containing a naphthyloxy-substituted anilide according to the invention.
- a preferred aspect of the invention is a germicidal detergent composition containing a naphthyloxy-substituted anilide according to the invention.
- the detergent composition can be in any convenient form such as liquid, paste or hard-surface cleaner but preferably should be in the form of a toilet bar. Suitable formulations for germicidal detergent compositions are given in standard textbooks, for example in Schwartz and Perry, Surface -Active Agents.
- a naphthyloxy-substituted anilide according to the invention can be used in conjunction with other germicides, such as 3,4,4'-trichlorocarbanilide, 3,4,4'-tribromosalicylanilide, 2,2-dihydroxy-3,5,6,3',5',6'-hexachlorodiphenylmethane and 4,2,4'-trichloro-Z-hydroxy-diphenylether.
- germicides such as 3,4,4'-trichlorocarbanilide, 3,4,4'-tribromosalicylanilide, 2,2-dihydroxy-3,5,6,3',5',6'-hexachlorodiphenylmethane and 4,2,4'-trichloro-Z-hydroxy-diphenylether.
- a further aspect of the invention is a pharmaceutical or veterinary composition containing a naphthyloxy-substituted anilide according to the invention together with a pharmaceutically acceptable or veterinarily acceptable carrier.
- the anilides according to the invention can be prepared by a variety of methods.
- one method is the condensation of a naphthylamino-phenylether with a salicyclic acid, the ether and the salicylic acid being prepared by standard methods. A salicylanilide is thereby obtained.
- a halogenated salicylanilide according to the invention is required, a halogenated naphthylamino-phenylether and/or a halogenated salicylic acid can be used.
- An alternative method is the direct halogenation of a naphthyloxy salicylanilide.
- Another example of a method of preparing an anilide according to the invention is by reaction of a naphthylamino-phenylether with an aryl isocyanate, the ether and the isocyanate being prepared by standard methods. A carbanilide is thereby obtained.
- halogenated compounds can be made by appropriate condensation or by halogenation of a naphthyloxy carbanilide.
- EXAMPLE 2 2'-fi-naphthyloxysalicylanilide 1.0 gms. of 2-aminophenyl-jS-naphthylether, 0.58 gm. (0.0042 mole) of salicylic acid and 0.25 ml. of phosphorus trichloride in 20 mls. of chlorobenzene were refluxed for three hours.
- Working up the reaction product as described in Example 1 gave 0.5 gm. (32%) of 2'19- naphthyloxysalicylanilide, M.P. 1l8-120 C. from an alcohol-water mixture.
- EXAMPLE 6 3 ,5 ,3 -trichloro-2'-fl-naphthyloxysalicylanilide A solution of 1.5 gms. (0.005 mole) of 4-chloro-2- amino-,S-naphthylether, 1.03 gms. (0.005 mole) 3,5-di- *Minimum Inhibitory Concentration against Staph. aureus in parts per million.
- EXAMPLE 7 -chloro-2'-a-naphthyloxysalicylanilide A solution of 2.0 gms. (0.0084 mole) of Z-aminophenyl-a-naphthylether 1.45 gms. (0.0084 mole) of 5- chlorosalicylic acid and 0.5 ml. of phosphorus trichloride in mls. of chlorobenzene was refluxed for three hours. Working up the reaction product as described in Example 5 gave 0.85 gm. (25.6%) of 5-chloro-2'-a-naphthyloxysalicylanilide, M.P. 184-6 C. from an alcohol-water mixture.
- EXAM PLE 8 3,4-dichloro-2'-,8-naphthyloxycarbanilide
- 2 gms. (0.0084 mole) of 2- aminophenyl-a-naphthylether in 20 mls. chloroform was added 1.58 gms. (0.0084 mole) of 3,4-dichlorophenylisocyanate, and the mixture stirred for 3 /2 hours.
- the chloroform was removed under reduced pressure, and the crude product washed twice with 60-80 petroleum ether. Recrystallisation of this solid from an alcohol-water mixture gave 1.948 gms. (54.4%) of 3,4-dichloro-2-u-naphthyloxy-carbanilide, M.P. 18l-3 C.
- MIC l-2 By way of comparison, the MIC of salicylanilide is 50.
- a naphthyloxy-substituted salicylanilide selected from the group consisting of 2-(alphaenaphthyloxy)-.salicylanilides and 2'-(beta naphthyloxy) salicylanilides and wherein from 0 to 3 of the 3, 4, 5, 6, 3, 4, 5' and 6 positions of the salicylanilide may have attached thereto a chlorine atom instead of a hydrogen atom.
- a naphthyloxy-substituted salicylanilide according to claim 1 which is 2'-(alpha-naphthyloxy)-salicylanilide.
- a naphthyloxy-substituted salicylanilide according to claim 1 which is 2'-(beta-naphthyloxy)-salicylanilide.
- a naphthyloxy-substituted salicylanilide according to claim 1 which is substituted with 1 to 3 chlorine atoms.
- a naphthyloxy-substituted salicylanilide according to claim 4 which is 5-chloro-2'-(beta-naphthyloxy)-salicylanilide.
- a naphthyloxy-substituted salicylanilide according to claim 4 which is 3,5-dichloro-2'-(alpha naphthyloxy)- salicylanilide.
- a naphthyloxy-substituted salicylanilide according to claim 4 which is 3,5-dichloro-2'-('beta-naphthyloxy)-salicylanilide.
- a naphthyloxy-substituted salicylanilide according to claim 4 which is 3,5-3-trichl0ro-2'-(beta naphthyloxy)- salicylanilide.
- a naphthyloxy-substituted salicylanilide according to claim 4 which is 5-chloro-2-(alpha-naphthyloxy)-salicylanilide.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5742968 | 1968-12-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3706799A true US3706799A (en) | 1972-12-19 |
Family
ID=10479173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US881869A Expired - Lifetime US3706799A (en) | 1968-12-03 | 1969-12-03 | Naphthyloxysalicylanilides |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3706799A (enrdf_load_stackoverflow) |
| GB (1) | GB1226438A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050187300A1 (en) * | 2002-07-15 | 2005-08-25 | Myriad Genetics, Incorporated | Compounds, compositions, and methods employing same |
| WO2006060580A1 (en) * | 2004-11-30 | 2006-06-08 | Myriad Genetics, Inc. | Therapeutic formulations |
| US20080045595A1 (en) * | 2004-12-27 | 2008-02-21 | Myriad Genetics, Incorporated | Method of treating cancer |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54117445A (en) * | 1977-12-13 | 1979-09-12 | Sumitomo Chem Co Ltd | Substituted phenylurea derivative, its preparation, and herbicide containing the same |
| CN112888673B (zh) | 2018-04-25 | 2022-07-29 | 查尔斯德鲁医药科学大学 | 新颖mct4抑制剂及其用途 |
-
1968
- 1968-12-03 GB GB5742968A patent/GB1226438A/en not_active Expired
-
1969
- 1969-12-03 US US881869A patent/US3706799A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050187300A1 (en) * | 2002-07-15 | 2005-08-25 | Myriad Genetics, Incorporated | Compounds, compositions, and methods employing same |
| US7547804B2 (en) | 2002-07-15 | 2009-06-16 | Myriad Genetics, Inc. | Compounds, compositions, and methods employing same |
| WO2006060580A1 (en) * | 2004-11-30 | 2006-06-08 | Myriad Genetics, Inc. | Therapeutic formulations |
| US20080045595A1 (en) * | 2004-12-27 | 2008-02-21 | Myriad Genetics, Incorporated | Method of treating cancer |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1226438A (enrdf_load_stackoverflow) | 1971-03-31 |
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