DE2303761A1 - Neue n,n'-disubstituierte thioharnstoffe, deren herstellung sowie verwendung als antimikrobielle substanzen - Google Patents
Neue n,n'-disubstituierte thioharnstoffe, deren herstellung sowie verwendung als antimikrobielle substanzenInfo
- Publication number
- DE2303761A1 DE2303761A1 DE2303761A DE2303761A DE2303761A1 DE 2303761 A1 DE2303761 A1 DE 2303761A1 DE 2303761 A DE2303761 A DE 2303761A DE 2303761 A DE2303761 A DE 2303761A DE 2303761 A1 DE2303761 A1 DE 2303761A1
- Authority
- DE
- Germany
- Prior art keywords
- disubstituted
- acetone
- disubstituted thioureas
- radical
- lower alkyl
- 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.)
- Pending
Links
- 229910052757 nitrogen Inorganic materials 0.000 title claims description 21
- 239000000126 substance Substances 0.000 title description 16
- 230000000845 anti-microbial effect Effects 0.000 title description 10
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000003585 thioureas Chemical class 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- -1 alkyl radical Chemical class 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 239000008164 mustard oil Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 3
- 241000192125 Firmicutes Species 0.000 claims description 3
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical class ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004599 antimicrobial Substances 0.000 claims description 2
- 239000002537 cosmetic Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- YGSFNCRAZOCNDJ-UHFFFAOYSA-N propan-2-one Chemical compound CC(C)=O.CC(C)=O YGSFNCRAZOCNDJ-UHFFFAOYSA-N 0.000 description 7
- 244000052616 bacterial pathogen Species 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000000344 soap Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 235000013162 Cocos nucifera Nutrition 0.000 description 4
- 244000060011 Cocos nucifera Species 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- RYPVUNGPPCYIDC-UHFFFAOYSA-N 1,4-dioxane;propan-2-one Chemical compound CC(C)=O.C1COCCO1 RYPVUNGPPCYIDC-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000002781 deodorant agent Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- UFJVEBNHBZBPHG-UHFFFAOYSA-N 1,1-dichloroethane;1,4-dioxane Chemical compound CC(Cl)Cl.C1COCCO1 UFJVEBNHBZBPHG-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- IKMJGHPYOYVETB-UHFFFAOYSA-N 1,4-dioxane;ethyl acetate Chemical compound CCOC(C)=O.C1COCCO1 IKMJGHPYOYVETB-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical class OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 235000010919 Copernicia prunifera Nutrition 0.000 description 1
- 244000180278 Copernicia prunifera Species 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 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
- OTGQIQQTPXJQRG-UHFFFAOYSA-N N-(octadecanoyl)ethanolamine Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCO OTGQIQQTPXJQRG-UHFFFAOYSA-N 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 241000191963 Staphylococcus epidermidis Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- CXADQLLYLMBGTG-UHFFFAOYSA-N acetonitrile;1,4-dioxane Chemical compound CC#N.C1COCCO1 CXADQLLYLMBGTG-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical class C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- SMVRDGHCVNAOIN-UHFFFAOYSA-L disodium;1-dodecoxydodecane;sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC SMVRDGHCVNAOIN-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/18—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/24—Derivatives of thiourea containing any of the groups, X being a hetero atom, Y being any atom
- C07C335/26—Y being a hydrogen or a carbon atom, e.g. benzoylthioureas
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/40—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of thiourea or isothiourea groups further bound to other hetero atoms
- C07C335/42—Sulfonylthioureas; Sulfonylisothioureas
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2303761A DE2303761A1 (de) | 1973-01-26 | 1973-01-26 | Neue n,n'-disubstituierte thioharnstoffe, deren herstellung sowie verwendung als antimikrobielle substanzen |
| US05/425,800 US3966968A (en) | 1973-01-26 | 1973-12-18 | N,N'-disubstituted thioureas, their process of production and use as antimicrobial agents |
| NL7317791A NL7317791A (https=) | 1973-01-26 | 1973-12-28 | |
| IT19644/74A IT1053752B (it) | 1973-01-26 | 1974-01-21 | Tiourea n . n bisostituita utile come sostanza antimicrobica e sua produzione |
| GB350974A GB1397234A (en) | 1973-01-26 | 1974-01-25 | N,n-disubstituted thioureas their preparation and their use as antimicrobial substances |
| FR7402599A FR2215228B1 (https=) | 1973-01-26 | 1974-01-25 | |
| BE140163A BE810147A (fr) | 1973-01-26 | 1974-01-25 | Thiourees n |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2303761A DE2303761A1 (de) | 1973-01-26 | 1973-01-26 | Neue n,n'-disubstituierte thioharnstoffe, deren herstellung sowie verwendung als antimikrobielle substanzen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2303761A1 true DE2303761A1 (de) | 1974-08-01 |
Family
ID=5870017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2303761A Pending DE2303761A1 (de) | 1973-01-26 | 1973-01-26 | Neue n,n'-disubstituierte thioharnstoffe, deren herstellung sowie verwendung als antimikrobielle substanzen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3966968A (https=) |
| BE (1) | BE810147A (https=) |
| DE (1) | DE2303761A1 (https=) |
| FR (1) | FR2215228B1 (https=) |
| GB (1) | GB1397234A (https=) |
| IT (1) | IT1053752B (https=) |
| NL (1) | NL7317791A (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010031657A3 (de) * | 2008-09-17 | 2011-03-17 | Henkel Ag & Co. Kgaa | Verwendung von harnstoff-derivaten und phenacylthiazolium-salzen zur behandlung von körpergeruch |
| WO2011029688A3 (de) * | 2009-09-11 | 2011-05-26 | Henkel Ag & Co. Kgaa | Inhibierung von körpergerüchen |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6271261B1 (en) * | 1996-06-27 | 2001-08-07 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| CZ425598A3 (cs) * | 1996-06-27 | 1999-08-11 | Smithkline Beecham Corporation | Antagonista IL-8 receptoru |
| AU2002322720B2 (en) | 2001-07-25 | 2008-11-13 | Raptor Pharmaceutical Inc. | Compositions and methods for modulating blood-brain barrier transport |
| TW200418812A (en) * | 2002-10-29 | 2004-10-01 | Smithkline Beecham Corp | IL-8 receptor antagonists |
| KR20050111306A (ko) | 2002-11-19 | 2005-11-24 | 아칠리온 파르마세우티칼스 인코포레이티드 | 바이러스 복제 억제제로서의 치환된 아릴 티오우레아 및관련 화합물 |
| TW200600492A (en) * | 2004-05-18 | 2006-01-01 | Achillion Pharmaceuticals Inc | Substituted aryl acylthioureas and related compounds; inhibitors of viral replication |
| CA2789262C (en) | 2005-04-28 | 2016-10-04 | Proteus Digital Health, Inc. | Pharma-informatics system |
| US8097626B2 (en) * | 2006-04-21 | 2012-01-17 | Glaxosmithkline Llc | IL-8 receptor antagonists |
| PL2009992T3 (pl) * | 2006-04-21 | 2012-11-30 | Glaxosmithkline Llc | Antagoniści receptora IL-8 |
| CL2007001829A1 (es) * | 2006-06-23 | 2008-01-25 | Smithkline Beecham Corp | P-toluensulfonato de n-[4-cloro-2-hidroxi-3-(piperazina-1-sulfonil)fenil]-n-(2-cloro-3-fluorofenil)urea;procedimiento de preparacion;composicion farmaceutica;combinacion farmaceutica;y uso en el tratamiento de una enfermedad mediada por la quiimioquina il-8, tales como asma y epoc. |
| EP2063905B1 (en) | 2006-09-18 | 2014-07-30 | Raptor Pharmaceutical Inc | Treatment of liver disorders by administration of receptor-associated protein (rap)-conjugates |
| US8028844B2 (en) * | 2008-11-20 | 2011-10-04 | Costa Charles A | Sliding closet rack |
| TR201908314T4 (tr) | 2009-02-20 | 2019-06-21 | 2 Bbb Medicines B V | Glutatyon bazlı ilaç dağıtım sistemi. |
| KR101909711B1 (ko) | 2009-05-06 | 2018-12-19 | 라보라토리 스킨 케어, 인크. | 활성제-칼슘 포스페이트 입자 복합체를 포함하는 피부 전달 조성물 및 이들을 이용하는 방법 |
| US8628961B2 (en) * | 2010-05-18 | 2014-01-14 | Tufts University | Small molecule antagonists of phosphatidylinositol-3,4,5-triphosphate (PIP3) and uses thereof |
| US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL193403A (https=) * | 1953-12-22 | 1924-02-17 | ||
| US3686418A (en) * | 1969-10-23 | 1972-08-22 | Armour & Co | N-acyl-n{40 -(halogenated aryl ureas as antibacterial agents) |
| SU517587A1 (ru) * | 1971-08-23 | 1976-06-15 | Медицинска Академие (Инопредприятие) | Способ получени производных 2оксфенилмочевины |
-
1973
- 1973-01-26 DE DE2303761A patent/DE2303761A1/de active Pending
- 1973-12-18 US US05/425,800 patent/US3966968A/en not_active Expired - Lifetime
- 1973-12-28 NL NL7317791A patent/NL7317791A/xx unknown
-
1974
- 1974-01-21 IT IT19644/74A patent/IT1053752B/it active
- 1974-01-25 FR FR7402599A patent/FR2215228B1/fr not_active Expired
- 1974-01-25 BE BE140163A patent/BE810147A/xx unknown
- 1974-01-25 GB GB350974A patent/GB1397234A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010031657A3 (de) * | 2008-09-17 | 2011-03-17 | Henkel Ag & Co. Kgaa | Verwendung von harnstoff-derivaten und phenacylthiazolium-salzen zur behandlung von körpergeruch |
| WO2011029688A3 (de) * | 2009-09-11 | 2011-05-26 | Henkel Ag & Co. Kgaa | Inhibierung von körpergerüchen |
| US9217222B2 (en) | 2009-09-11 | 2015-12-22 | Henkel Ag & Co. Kgaa | Prevention of body odour |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1397234A (en) | 1975-06-11 |
| US3966968A (en) | 1976-06-29 |
| BE810147A (fr) | 1974-07-25 |
| FR2215228A1 (https=) | 1974-08-23 |
| IT1053752B (it) | 1981-10-10 |
| NL7317791A (https=) | 1974-07-30 |
| FR2215228B1 (https=) | 1977-09-09 |
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